Use of poly alpha-1,3-glucan ethers as viscosity modifiers

USE OF POLY-ALPHA-1,3-GLUCAN ETHERS AS MODIFIERS OF

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

THE VISCOSITY

FIELD OF THE INVENTION

The present invention relates to the field of viscosity modifying agents. Specifically, this invention relates to the use of poly-alpha1,3-glucan ethers as viscosity modifiers.

BACKGROUND OF THE INVENTION

Driven by the desire to find novel structural polysaccharides by enzymatic synthesis or genetic engineering of microorganisms or plant hosts, researchers have discovered polysaccharides that are biodegradable and can be produced economically from renewable source raw materials. One of these polysaccharides is polyalpha-1,3-glucan, a glucan polymer characterized in that it has alpha-1,3-glycosidic linkages. This polymer was isolated by contacting an aqueous sucrose solution with a glycosyltransferase enzyme isolated from Streptococcus salivarius (Simpson et al., Microbiology 141:1451-1460, 1995).

US patent no. 7,000,000 described the preparation of a polysaccharide fiber comprising hexose units, where at least 50% of the units

REF: 266629

<img file="MX373205B_D0001.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY hexose within the polymer were linked via alpha-1,3-glycosidic linkages with the use of a gtfJ enzyme from S. salivarius. This enzyme uses sucrose as a substrate in a polymerization reaction to produce poly-alpha-1,3-glucan and fructose as end products (Simpson et al., 1995). The disclosed polymer formed a liquid crystalline solution when dissolved above a critical concentration in a solvent or in a mixture comprising a solvent. From this solution, continuous, strong, cotton-like fibers highly suitable for use in textiles were spun and used.

Kiho et al. (Carb. Res. 189:273-270, 1989) described the alkaline extraction and isolation of poly-alpha-1,3-glucan from the fungus, Agrocybe cylindracea, which was further derivatized to sodium carboxymethylglucan (CMG). This ether derivative showed antitumor properties against sarcoma. Similarly, Zhang et al. (International Publication No. CN1283633) described the extraction of poly-alpha-1,3-glucan from the medicinal mushroom, Ganoderma lucidum, and its derivation to CMG.

BRIEF DESCRIPTION OF THE INVENTION

In one embodiment, the present invention relates to a hydrocolloid or aqueous solution comprising a poly-alpha-1,3-glucan ether compound represented by the structure:

<img file="MX373205B_D0002.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

<img file="MX373205B_D0003.tif" />

where:

(i) n is at least 6, (ii) each R is, independently, an H or an organic group, (iii) the compound has a degree of substitution of from about 0.05 to about 3.0, and (iv) the hydrocolloid or solution aqueous has a viscosity of at least about 10 cPs.

In a second embodiment, at least one organic group is selected from the group consisting of alkyl group, hydroxyalkyl group, and carboxyalkyl group. The compound of the present embodiment may contain one kind of organic group or two or more kinds of organic groups. At least one organic group is selected, for example, from the group consisting of carboxymethyl, methyl, ethyl, hydroxypropyl, dihydroxypropyl and hydroxyethyl groups. In a third embodiment, the compound contains one type of organic group, while in a fourth embodiment, the compound contains two or more types of organic groups.

<img file="MX373205B_D0004.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

In a fifth embodiment, the degree of substitution of the poly-alpha-1,3-glucan ether compound is from about 0.2 to about 2.0.

In a sixth embodiment, the polyalpha-1,3-glucan ether compound is crosslinked.

In a seventh embodiment, the pH of the hydrocolloid or aqueous solution is from about 2.0 to about 12.0.

In an eighth embodiment, the hydrocolloid or aqueous solution has pseudoplastic behavior or dilatant behavior.

In a ninth embodiment, the hydrocolloid or aqueous solution is in the form of a personal care product, pharmaceutical product, food product, household product, or industrial product.

In a tenth embodiment, the invention relates to a method of increasing the viscosity of an aqueous composition. This method comprises contacting a poly-alpha-1,3-glucan ether compound as described herein with an aqueous composition and thereby increasing the viscosity of the aqueous composition.

In an eleventh embodiment, the contacting step of the method is carried out by mixing or dissolving the poly-alpha-1,3-glucan ether compound in the aqueous composition. In a twelfth embodiment, the aqueous composition

<img file="MX373205B_D0005.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY obtained from this mixture or solution is not filtered. In a thirteenth embodiment, the mixing or dissolution comprises a homogenization stage.

In a fourteenth embodiment, the pseudoplastic behavior or dilatant behavior of the aqueous composition is increased in the contact stage of the method.

In a fifteenth embodiment, the invention relates to a method of treating a material. This method comprises contacting a material with an aqueous composition comprising a poly-alpha-1,3-glucan ether compound as described herein. In certain embodiments of this method, the polyalpha-1,3-glucan ether compound is adsorbed onto the surface of the material.

DETAILED DESCRIPTION OF THE INVENTION

Disclosures from all patent and non-patent literature cited herein are incorporated herein by reference in their entirety.

As used in this description, the term "invention" or "disclosed invention" is not intended to be limiting, but rather applies generally to any of the inventions defined in the claims or described in this description. These terms are used interchangeably in the present description.

The terms poly alpha-1,3-glucan, alpha-1,3-glucan polymer, and glucan polymer are used interchangeably.

<img file="MX373205B_D0006.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY in this description. Poly-alpha-1,3-glucan is a polymer comprising glucose monomeric units linked together by glycosidic bonds (ie, glycosidic bonds), wherein at least about 50% of the glycosidic bonds are alpha- 1,3-glycosidics. Poly alpha-1,3-glucan is a type of polysaccharide. The structure of poly alpha-1,3-glucan can be illustrated as follows:

<img file="MX373205B_D0007.tif" />

The poly-alpha-1,3-glucan that can be used to prepare the poly-alpha-1,3-glucan ether compounds of the present disclosure can be prepared using chemical methods. Alternatively, they can be prepared by extracting them from various organisms, such as fungi, that produce polyalpha-1,3-glucan. Alternatively, poly-alpha-1,3-glucan can be produced enzymatically from sucrose with the use of one or more glycosyltransferase (gtf) enzymes (eg, gtfJ), as described in US Pat. no. 7,000,000 and in the publications of the requests

<img file="MX373205B_D0008.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY US patent no. 2013/0244288 and 2013/0244287 (both of which are incorporated herein by reference), for example.

The terms glucosyltransferase enzyme, gtf enzyme, gtf enzyme catalyst, gtf and glucanosucrase are used interchangeably in the present description. The activity of a gtf enzyme in the present disclosure catalyzes the reaction of the substrate sucrose to obtain the products poly alpha-1,3-glucan and fructose. Other products (by-products) of a gtf reaction can include glucose (resulting when glucose is hydrolyzed from the glycosyl-gtf enzyme intermediate complex), various soluble oligosaccharides (e.g., DP2-DP7), and leucrose (which results when glucose from the glycosyl-gtf enzyme intermediate complex binds to fructose). Leukrose is a disaccharide composed of glucose and fructose joined by an alpha-1.5 bond. Wild-type forms of glycosyltransferase enzymes generally contain (in the N-terminal to C-terminal direction) a signal peptide, a variable domain, a catalytic domain, and a glycan-binding domain. A gtf in the present description is classified in glycoside hydrolase family 70 (GH70) according to CAZy data (carbohydrate active enzymes (Cantarel et al., Nucleic Acids Res. 37:D233-238, 2009) .

The percentage of glycosidic bonds between units

<img file="MX373205B_D0009.tif" />

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monomeric glucose poly-alpha-1,3-glucan used to prepare the poly-alpha-1,3-glucan ether compounds of the present description that are alpha-1,3 is therefore minus about 50%, 60%, 70%, 80%, 90%, 95%, 96%, 97%, 98%, 99%, or 100% (or any integer between 50% and 100%) . Therefore, in such embodiments, a poly-alpha-1,3-glucan has less than about 50%, 40%, 30%, 20%, 10%, 5%, 4%, 3%, 2%, 1 % or 0% (or any integer value between 0% and 50%) of glycosidic linkages that are not alpha-1,3.

The poly-alpha-1,3-glucan used to produce the poly-alpha-1,3-glucan ether compounds of the present disclosure is preferably linear/unbranched. In certain embodiments, the poly-alpha-1,3-glucan has no branch points or has less than about 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2% or 1% of the branch points as a percentage of the glycosidic linkages in the polymer. Examples of branch points include alpha-1,6 branch points, such as those present in the mutant polymer.

The terms glycosidic bond and glycosidic linkage are used interchangeably in the present description and refer to the type of covalent bond that joins a carbohydrate (sugar) molecule with another group such as another carbohydrate. The term alpha-1,3-glycosidic bond, as used in the present description, refers to the type of

<img file="MX373205B_D0010.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY covalent bond that joins alpha-D-glucose molecules together through carbons 1 and 3 in adjacent alpha-D-glucose rings. This bond is illustrated in the structure of poly alpha-1,3-glucan provided above. In the present description, alpha-D-glucose will be referred to as glucose.

The terms poly-alpha-1,3-glucan ether compound, poly-alpha-1,3-glucan ether, and poly-alpha-1,3-glucan ether derivative are used interchangeably herein. A poly-alpha-1,3-glucan ether compound in the present description may be represented by the structure:

<img file="MX373205B_D0011.tif" />

With respect to the formula of this structure, n can be at least 6 and each R can be independently a hydrogen atom (H) or an organic group. A poly-alpha-1,3-glucan ether compound of the present disclosure has a degree of substitution of from about 0.05 to about 3.0. The poly-alpha-1,3-glucan ether compounds described in the application publication of

<img file="MX373205B_D0012.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY US patent no. 2014/0179913 (herein incorporated by reference), and those described in the present description, can be used to prepare the hydrocolloids or aqueous solutions of the present invention, for example.

A poly-alpha-1,3-glucan ether compound is defined as an ether in the present description by virtue of comprising the substructure -Cg-OC-, where -Cg- represents carbon 2, 4 or 6 of a unit glucose monomer of a poly-alpha-1,3-glucan ether compound, and wherein -C- is contained in the organic group.

The poly-alpha-1,3-glucan ether compounds described in the present description are man-made synthetic compounds.

An organic group, as used in the present description, refers to a chain of one or more carbons that (i) has the formula -C_nH₂n+i (ie, an alkyl group, fully saturated) or (ii) is primarily saturated, but has one or more hydrogens substituted with another atom or functional group (eg, a substituted alkyl group). Such substitution may be with one or more hydroxyl groups, oxygen atoms (to form an aldehyde or ketone group), carboxyl groups, or other alkyl groups. In other words, where R is an organic group, R can be a chain of one or more saturated carbons or a chain of carbons that

<img file="MX373205B_D0013.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY has one or more hydrogens substituted with a hydroxyl group, oxygen atom (to form an aldehyde or ketone group), carboxyl group or alkyl group. An organic group in the present disclosure may be uncharged or anionic (an example of an anionic organic group is a carboxyalkyl group).

A hydroxyalkyl group in the present description refers to a substituted alkyl group in which one or more hydrogen atoms of the alkyl group are replaced with a hydroxyl group. A carboxyalkyl group in the present description refers to a substituted alkyl group in which one or more hydrogen atoms of the alkyl group are replaced with a carboxyl group.

A halide in the present description refers to a compound comprising one or more halogen atoms (eg, fluorine, chlorine, bromine, iodine). A halide in the present description can refer to a compound comprising one or more halide groups, such as fluoride, chloride, bromide or iodide. A halide group can function as a reactive group of an etherifying agent.

The terms reaction, reaction composition, and etherification reaction are used interchangeably herein and refer to a reaction comprising at least poly-alpha-1,3-glucan and an etherification agent. These components are dissolved and/or mixed,

<img file="MX373205B_D0014.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY typically, in an aqueous alkali hydroxide. A reaction is carried out under suitable conditions (eg, time, temperature) for the etherifying agent to etherify one or more hydroxyl groups of the glucose units of poly-alpha-1,3-glucan with an organic group, and thus produce a poly-alpha-1,3-glucan ether compound.

The term alkaline conditions in the present description refers to a solution or mixture with a pH of at least 11 or 12. Alkaline conditions can be prepared by any means known in the art, such as by dissolving an alkali hydroxide in a solution or mixture.

The terms etherification agent and alkylation agent are used interchangeably in the present description. An etherifying agent in the present description refers to an agent that can be used to etherify one or more hydroxyl groups of one or more glucose units of poly-alpha-1,3-glucan with an organic group. Therefore, an etherifying agent comprises an organic group.

The term poly-alpha-1,3-glucan suspension in the present description refers to an aqueous mixture comprising the components of a glycosyltransferase enzyme reaction, such as poly-alpha-1,3-glucan, sucrose, one or plus glycosyltransferase enzymes, glucose and

<img file="MX373205B_D0015.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY fructose. This composition is a suspension since poly alpha-1,3-glucan does not dissolve in it.

The term poly-alpha-1,3-glucan wet agglomerate in the present description refers to a poly-alpha-1,3-glucan that has been separated from a suspension and washed with water or an aqueous solution. Poly-alpha-1,3-glucan does not dry completely when preparing a wet agglomerate.

The term "degree of substitution" (DoS), as used herein, refers to the average number of substituted hydroxyl groups on each monomeric (glucose) unit of a poly-alpha-1,3-glucan ether compound. Since there are three hydroxyl groups in each monomeric unit in poly-alpha-1,3-glucan, the degree of substitution in a poly-alpha-1,3-glucan ether compound of the present disclosure may be greater than 3.

The term molar substitution (MS), as used herein, refers to the moles of an organic group per monomeric unit of a poly-alpha-1,3-glucan ether compound. Alternatively, MS can refer to the average number of moles of etherifying agent used to react with each monomeric unit in poly-alpha-1,3-glucan (hence, MS can describe the degree of derivatization of an etherifying agent). etherification). It is noted that the MS value for poly-alpha-1,3-glucan may not have an upper limit. By

<img file="MX373205B_D0016.tif" />

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example, when an organic group containing a hydroxyl group (for example, hydroxyethyl or hydroxypropyl) has been etherified to obtain poly-alpha-1,3-glucan, the hydroxyl group of the organic group may undergo another reaction , and thus couple more of the organic group to the poly-alpha1,3-glucan.

The term "crosslink" in the present description refers to a chemical bond, atom or group of atoms that connects two adjacent atoms in one or more polymeric molecules. It should be understood that, in a composition comprising crosslinked poly-alpha-1,3-glucan ether, the crosslinks may be between at least two poly-alpha-1,3-glucan ether molecules (i.e., intermolecular crosslinks). ; in addition, there may be intramolecular cross-linking. A crosslinking agent, as used herein, is an atom or compound that can create crosslinks.

An aqueous composition of the present description refers to a solution or mixture in which the solvent is at least about 20% by weight of water, for example, and which comprises poly-alpha-1,3-glucan and/or a compound of poly-alpha-1,3-glucan ether. Examples of aqueous compositions of the present description are aqueous solutions and hydrocolloids.

The terms hydrocolloid and hydrogel are used

<img file="MX373205B_D0017.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY interchangeably in this description. A hydrocolloid refers to a colloidal system in which water is the dispersion medium. A colloid refers, in the present description, to a substance microscopically dispersed in any other substance. Therefore, a hydrocolloid in the present description can further refer to a dispersion, emulsion, mixture or solution of poly-alpha-1,3-glucan and/or one or more poly-alpha-1,3-glucan ether compounds. in water or aqueous solution.

The term aqueous solution in the present description refers to a solution in which the solvent is water. The poly-alpha-1,3-glucan and/or one or more poly-alpha-1,3-glucan ether compounds of the present disclosure may be dispersed, mixed and/or dissolved in an aqueous solution. An aqueous solution may be useful as the dispersion medium for a hydrocolloid of the present disclosure.

The terms dispersant and dispersing agent are used interchangeably in the present description to refer to a material that promotes the formation and stabilization of a dispersion of one substance in another. A dispersion refers, in the present description, to an aqueous composition comprising one or more particles (for example, any ingredient of a personal care product, pharmaceutical product, food product, household product or industrial product).

<img file="MX373205B_D0018.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY described in the present description) that are dispersed, or uniformly dispersed, throughout the aqueous composition. It is believed that poly-alpha-1,3-glucan and/or poly-alpha-1,3-glucan ether compounds can act as dispersants in aqueous compositions described herein.

The term viscosity, as used herein, refers to the measure of the extent to which a fluid or aqueous composition, such as a hydrocolloid, resists a force tending to make it flow. Various units of viscosity that can be used in the present description include centipoise (cps) and pascal-seconds (Pa-s). A centipoise is one hundredth of a poise; one poise is equal to 0.100 kg-m^'S^-1. Therefore, the terms viscosity modifier and viscosity modifying agent, as used in the present description, refer to any element that can alter/modify the viscosity of a fluid or aqueous composition.

The term shear thinning behavior, as used herein, refers to a decrease in the viscosity of the hydrocolloid or aqueous solution as the shear rate increases. The term dilatant behavior, as used in the present description, refers to an increase in the viscosity of the hydrocolloid or aqueous solution as the shear rate increases. Cutting speed, in the present description, refers

<img file="MX373205B_D0019.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY at the rate at which progressive shear deformation is applied to the hydrocolloid or aqueous solution. A shear strain can be applied in a rotational manner.

The term contacting, as used herein, with respect to methods of increasing the viscosity of an aqueous composition, refers to any action by which an aqueous composition is combined with poly-alpha-1,3- glucan and/or a poly-alpha-1,3-glucan ether compound. The contact can be carried out, for example, by any means known in the art, such as dissolution, mixing, stirring or homogenization.

The terms fabric, textile and cloth are used interchangeably in the present description to refer to a woven material having a network of natural and/or man-made fibers. Such fibers can be strands or threads, for example.

A fabric care composition in the present description is any composition suitable for treating fabrics in some way. Some examples of the composition include laundry detergents and fabric softeners.

The terms high performance detergent and multipurpose detergent are used interchangeably in this description to refer to a detergent useful for regular washing of white and colored fabrics at any

<img file="MX373205B_D0020.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY temperature. The terms light duty detergent or fine fabric detergent are used interchangeably in this description to refer to a detergent useful for the care of delicate fabrics, such as viscose, wool, silk, microfiber or other fabric requiring special care. Special care may include conditions of use of excess water, low agitation and/or lack of bleach, for example.

An oral care composition in the present description is any composition suitable for the treatment of a soft or hard surface in the oral cavity such as dental surfaces (teeth) and/or gum surfaces.

The term adsorption in the present description refers to the adhesion of a compound (eg, poly-alpha-1,3-glucan ether) to the surface of a material.

The molecular weight of poly-alpha-1,3-glucan and poly-alpha-1,3-glucan ether compounds in the present description can be represented as number average molecular weight (M_n) or as weight average molecular weight (M_w) . Alternatively, molecular weight can be represented as Daltons, grams/mol, DPw (weight average degree of polymerization), or DPn (number average degree of polymerization). Various means are known in the art for calculating these molecular weight measurements, such as chromatography

<img file="MX373205B_D0021.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY high pressure liquid (HPLC), size exclusion chromatography (SEC) or gel permeation chromatography (GPC).

The terms percent by volume, percent by volume, vol%, and v/v% are used interchangeably in the present description. The percent by volume of a solute in a solution can be determined by using the formula: [(volume of solute)/(volume of solution)] x 100%.

The terms weight percent, weight percent (wt%) and weight-weight percent (w/w%) are used interchangeably in the present description. Weight percent refers to the percentage of a material by mass, as composed in a composition, mixture, or solution.

The terms increased, increased and improved are used interchangeably in the present description. These terms refer to a greater amount or activity such as an amount or activity slightly greater than the original amount or activity, or an amount or activity in great excess compared to the original amount or activity, and include all amounts or activities between these. Alternatively, these terms may refer to, for example, an amount or activity that is at least 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 100%, 125%, 150%, 175%, or 200% (or any integer between 1% and 200%) greater than the amount or activity

<img file="MX373205B_D0022.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY to which the increase in quantity or activity is compared.

The development of new poly-alpha-1,3-glucan ether derivatives and methods for preparing such derivatives is desirable because of their potential utility in various applications. There is great interest in understanding the applicability of poly-alpha1,3-glucan ether derivatives as viscosity and rheology modifiers of hydrocolloids or aqueous compositions.

Embodiments of the disclosed invention relate to a hydrocolloid or aqueous solution comprising a poly-alpha-1,3-glucan ether compound represented by the structure:

<img file="MX373205B_D0023.tif" />

With respect to the formula of this structure, n can be at least 6 and each R can independently be an H or an organic group. Furthermore, the polyalpha-1,3-glucan ether compound has a degree of substitution of from about 0.05 to about 3.0. The hydrocolloid or aqueous solution comprising the poly373205 ether compound

<img file="MX373205B_D0024.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY alpha-1,3-glucan has a viscosity of at least about 10 centipoise (cps).

Significantly, a poly-alpha1,3-glucan ether compound used in the invention can modify the viscosity of an aqueous solution to which it is added. This viscosity modifying effect is often associated with a rheology modifying effect. Furthermore, when a hydrocolloid or aqueous solution of the present disclosure is brought into contact with a surface (eg, fabric surface), one or more poly-alpha-1,3-glucan ether compounds are adsorbed on the surface. .

The degree of substitution (DoS) of a poly-alpha-1,3-glucan ether compound described herein may alternatively be from about 0.2 to about 2.0. Alternatively, the DoS can be at least about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9 or 3.0. Those skilled in the art will understand that since a poly-alpha-1,3-glucan ether compound of the present disclosure has a degree of substitution of from about 0.05 to about 3.0 and by virtue of being an ether, the R groups of the compound cannot be only hydrogen.

The DoS of a poly-alpha-1,3-glucan ether compound described in the present description can affect the

<img file="MX373205B_D0025.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY Viscosity of the hydrocolloid or aqueous solution that comprises the compound. For example, a hydrocolloid or aqueous solution comprising a carboxymethyl poly-alpha-1,3-glucan (CMG) with a DoS of about 0.4 to 0.6 has higher viscosity than a hydrocolloid or aqueous solution comprising a CMG with a higher DoS. high (for example, from about 0.8 to 1.0).

The percentage of glycosidic linkages between the glucose monomeric units of poly-alpha1,3-glucan ether compounds of the present disclosure that are alpha-1,3 is at least about 50%, 60%, 70%, 80%. , 90%, 95%, 96%, 97%, 98%, 99%, or 100% (or any integer between 50% and 100%) . Therefore, in such embodiments, the compound has less than about 50%, 40%, 30%, 20%, 10%, 5%, 4%, 3%, 2%, 1%, or 0% (or any value integer between 0% and 50%) of glycosidic linkages other than alpha-1,3.

The backbone of a polyalpha-1,3-glucan ether compound of the present disclosure is preferably linear/unbranched. In certain embodiments, the compound has no branch points or has less than about 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, or 1% branch points such as a percentage of the glycosidic linkages in the polymer. Examples of branch points include alpha branch points

1,6.

The formula of a poly-alpha-1,3-glucan ether compound, in certain embodiments, can have an n value of at least 6. Alternatively, n can have a value of at least 25, 50, 75, 100, 150 , 200, 250, 300, 350, 400, 450, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500,

1600, 1700, 1800, 1900, 2000, 2100, 2200, 2300, 2400, 2500,

2600, 2700, 2800, 2900, 3000, 3100, 3200, 3300, 3400, 3500,

3600, 3700, 3800, 3900, or 4000 (or any integer between 25 and 4000), for example. In still other examples, the value of n can be in a range of 25-250, 50-250, 75-250, 100-250, 150-250, 200-250, 25-200, 50-200, 75-200, 100-200 , 150-200, 25-150, 50-150, 75-150, 100-150, 25-100, 50100, 75-100, 25-75, 50-75 or 25-50.

The molecular weight of a poly-alpha1,3-glucan ether compound of the present disclosure can be determined as number average molecular weight (M_n) or as weight average molecular weight (M_w). Alternatively, the molecular weight can be determined in daltons or grams/mole. Also, it might be useful to reference the DP_W (weighted average degree of polymerization) or DP_n (number average degree of polymerization) of the poly-alpha1,3-glucan polymeric component of the compound.

The M_n or M_w of the poly-alpha-1,3-glucan ether compounds of the present disclosure can be at least about 1000. Alternatively, the M_n or M_w can be

<img file="MX373205B_D0026.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY from at least approximately 1,000 to approximately 600,000. Alternatively, the M_n or M_w It may be, for example, at least approximately 2000, 3000, 4000, 5000, 6000, 7000, 8000, 10,000, 15,000, 20,000, 25,000, 30,000, 35,000, 40,000, 45,000, 50,000, 75,000, 100,000, 150,000, 200,000, 250,000, 300,000, 350,000, 400,000, 450,000, 500,000, 550,000, or 600,000 (or any integer between 2,000 and 600,000).

Each R group in the formula of a poly-alpha-1,3-glucan ether compound of the present disclosure will independently be an H or an organic group. An organic group can be an alkyl group, such as a methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, or decyl group, for example.

Alternatively, an organic group may be a substituted alkyl group in which there is substitution on one or more carbons of the alkyl group. The substitution(s) may be one or more hydroxyl, aldehyde, ketone and/or carboxyl groups. For example, a substituted alkyl group can be a hydroxyalkyl group, dihydroxyalkyl group, or carboxyalkyl group.

Examples of suitable hydroxyalkyl groups are hydroxymethyl (-CH2OH), hydroxyethyl (eg CH2CH2OH, -CH(OH)CH3), hydroxypropyl (eg CH2CH2CH2OH, -CH₂CH(OH)CH₃, -CH(OH) CH2CH3), hydroxybutyl and hydroxypentyl. Other examples include dihydroxy groups

<img file="MX373205B_D0027.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY alkyl (diols), such as dihydroxymethyl, dihydroxyethyl (for example, -CH(OH)CH2OH), dihydroxypropyl (for example, -CH₂CH(OH)CH₂OH, -CH(OH)CH(OH)CH₃), dihydroxybutyl and dihydroxypentyl.

Examples of suitable carboxyalkyl groups are carboxymethyl (-CH2COOH), carboxyethyl (eg CH2CH2COOH, -CH(COOH)CH₃), carboxypropyl (for example, CH2CH₂CH₂COOH, -CH₂CH(COOH)CH_3z -CH(COOH)CH₂CH₃), carboxybutyl and carboxypentyl.

Alternatively, one or more carbons of an alkyl group may have one or more substitutions with another alkyl group. Examples of such substituent alkyl groups are methyl, ethyl and propyl groups. To illustrate, an R group can be -CH(CH₃)CH2CH₃ or -CH2CH(CH₃)CH₃eg, which are propyl groups having a methyl substitution.

As should be clear from the above examples of various substituted alkyl groups, a substitution (eg, hydroxy or carboxy group) on an alkyl group can, in certain embodiments, be attached to the terminal carbon atom of the alkyl group, where the The terminal carbon group is opposite to the terminal which is in ether bond with the glucose group in the glucan ether compound (formula above). An example of this terminal substitution is at the hydroxypropyl group -CH₂CH2CH₂ooh Alternatively, a substitution may be on a carbon atom.

<img file="MX373205B_D0028.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY internal carbon of an alkyl group. An example of an internal substitution is on the hydroxypropyl group CH2CH(OH)CH3. An alkyl group may have one or more substitutions, which may be the same (eg, two hydroxyl [dihydroxy] groups) or different (eg, one hydroxyl group and one carboxyl group).

In certain embodiments, the polyalpha-1,3-glucan ether compounds described herein may contain one type of organic group. For example, one or more R groups with an ether bond to the glucose group in the above formula may be a methyl group. Therefore, the R groups, in this particular example, would independently be hydrogen and methyl groups. Certain embodiments of poly-alpha-1,3-glucan ether compounds containing only one type of organic group do not have a carboxyalkyl group (eg, carboxymethyl group) as the organic group.

Alternatively, the poly-alpha1,3-glucan ether compounds of the present disclosure may contain two or more different types of organic groups. Examples of such compounds contain (i) two different alkyl groups as R groups, (ii) an alkyl group and a hydroxyalkyl group as R groups (poly-alpha-1,3-alkyl hydroxyalkyl glucan, generically speaking), (iii ) an alkyl group and a carboxyalkyl group as R groups (poly-alpha373205

<img file="MX373205B_D0029.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

carboxyalkyl 1,3-alkyl glucan, generically speaking), (iv) a hydroxyalkyl group and a carboxyalkyl group as R groups (hydroxyalkyl carboxyalkyl poly-alpha-1,3-glucan, generically speaking), (v) two hydroxyalkyl groups different as R groups or (vi) two different carboxyalkyl groups as R groups. Specific non-limiting examples of such compounds include hydroxyethyl ethyl alpha-1,3-glucan (i.e., wherein the R groups are independently H, ethyl, or hydroxyethyl), hydroxyalkyl methyl poly-alpha-1,3-glucan ( ie, wherein the R groups are independently H, hydroxyalkyl, or methyl), hydroxyethyl carboxymethyl poly-alpha-1,3-glucan (ie, wherein the R groups are independently H, carboxymethyl or hydroxyethyl) and carboxymethyl hydroxypropyl poly-alpha-1,3-glucan (ie, wherein the R groups are independently H, carboxymethyl, or hydroxypropyl).

The poly-alpha-1,3-glucan ether compounds of the present disclosure may comprise at least one nonionic organic group and at least one anionic group, for example. As another example, the poly-alpha-1,3-glucan ether compounds of the present disclosure may comprise at least one nonionic organic group and at least one positively charged organic group.

The hydrocolloids or aqueous solutions comprising a poly-alpha-1,3-glucan ether compound described in the

<img file="MX373205B_D0030.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY present description have a viscosity of at least about 10 cPs. Alternatively, a hydrocolloid or aqueous solution of the present disclosure has a viscosity of at least about 100, 250, 500, 750, 1000, 1500, 2000, 2500, 3000, 3500, 4000, 4500, 5000, 5500, 6000, 6500, 7000, 7500, 8000, 8500, 9000, 9500, 10,000, 10,500, 11,000, 12,000, 13,000, 14,000, 15,000, 20,000, 30,000, 40,000, 50,000, 60,000, 70,000, 80,000, 90,000 or 100,000 cps (or any whole between 100 between 100 and 100,000 cPs), for example.

Viscosity can be measured with the hydrocolloid or aqueous solution at any temperature between about 3°C ​​and about 110°C (or any integer between 3 and 110°C), for example. Alternatively, the viscosity can be measured at a temperature of from about 4°C to 30°C or from about 20°C to 25°C. Viscosity can be measured at 101 kilopascals (atmospheric pressure) (approximately 760 torr) or any other higher or lower pressure.

The viscosity of a hydrocolloid or aqueous solution described herein can be measured by use of a viscometer or rheometer or by use of any other means known in the art. Those skilled in the art should understand that a rheometer can be used to measure the viscosity of hydrocolloids and aqueous solutions of the same.

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY inventions that exhibit pseudoplastic behavior or dilatant behavior (that is, liquids with viscosities that vary depending on flow conditions). The viscosity of those embodiments can be measured at a rotary shear rate of about 10 to 1000 rpm (revolutions per minute) (or any integer between 10 and 1000 rpm), for example. Alternatively, the viscosity can be measured at a rotary shear rate of about 10, 60, 150, 250, or 600 rpm.

The pH of a hydrocolloid or aqueous solution described herein can be from about 2.0 to about 12.0. Alternatively, the pH can be about 2.0, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0, 10.0, 11.0, 12.0; or between 5.0 and about 12.0; or between about 4.0 and about 8.0; or between about 3.0 and 11.0. In certain embodiments, the viscosity of the hydrocolloid or aqueous solution does not fluctuate greatly, at a pH between about 3.0 and 11.0.

An aqueous composition of the present disclosure, such as a hydrocolloid or aqueous solution, may comprise a solvent having at least about 20% by weight of water. In other embodiments, a solvent has, for example, at least about 30, 40, 50, 60, 70, 80, 90, or 100% by weight of water (or any integer value between 20 and 100% by weight).

<img file="MX373205B_D0032.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY peso).

A poly-alpha-1,3-glucan ether compound described herein may be present, for example, in a hydrocolloid or aqueous solution in a weight percent (wt%) of at least about 0.01%, 0.05 %, 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1.0%, 1.2%, 1.4%, 1.6%, 1.8%, 2.0%, 2.5%, 3.0%, 3.5%, 4.0%, 4.5%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17% , 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29% or 30%.

A hydrocolloid or aqueous solution of the present disclosure may comprise other components in addition to one or more poly-alpha-1,3-glucan ether compounds. For example, the hydrocolloid or aqueous solution may comprise one or more salts, such as sodium salts (eg NaCl, NasSO4). Other non-limiting examples of salts include those having (i) an aluminum, ammonium, barium, calcium, chromium (II or III), copper (I or II), iron (II or III), hydrogen, lead (II ), lithium, magnesium, manganese (II or III), mercury (I or II), potassium, silver, sodium, strontium, tin (II or IV), or zinc and (ii) an acetate, borate, bromate, bromide anion , carbonate, chlorate, chloride, chlorite, chromate, cyanamide, cyanide, dichromate, dihydrogen phosphate, ferricyanide, ferrocyanide, fluoride, hydrogen carbonate, hydrogen phosphate, hydrogen sulfate, hydrogen sulfide, hydrogen sulfite, hydride, hydroxide,

<img file="MX373205B_D0033.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY hypochlorite, iodate, iodide, nitrate, nitride, nitrite, oxalate, oxide, perchlorate, permanganate, peroxide, phosphate, phosphide, phosphite, silicate, stannate, stanite, sulfate, sulfide, sulfite, tartrate or thiocyanate. Therefore, any salt having a cation of (i) above and an anion of (ii) above may be in a hydrocolloid or aqueous solution, for example. A salt may be present in a hydrocolloid or aqueous solution in a weight % of from about .01% to about 10.00% (or any hundredths increment between .01% and 10.00%), for example.

Those of skill in the art will understand that in certain embodiments of the invention a poly-alpha-1,3-glucan ether compound may be in an anionic form in a hydrocolloid or aqueous solution. Examples may include those poly-alpha-1,3-glucan ether compounds having an organic group comprising an alkyl group substituted with a carboxyl group. The carboxyl groups (COOH) in a poly-alpha-1,3-glucan carboxyalkyl ether compound can be converted to carboxylate groups (COO^-) under aqueous conditions. Such anionic groups may interact with salt cations, such as any of those listed in (i) above (eg potassium, sodium or lithium cation). Thus, a poly-alpha-1,3-glucan ether compound can be, for example, a sodium carboxylalkyl poly-alpha-1,3-glucan ether (for

<img file="MX373205B_D0034.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY example, sodium carboxymethyl poly-alpha-1,3-glucan), potassium carboxyalkyl poly-alpha-1,3-glucan ether (for example, poly-alpha-1,3- potassium carboxymethyl glucan) or lithium carboxyalkyl poly-alpha-1,3-glucan ether (for example, lithium carboxymethyl poly-alpha-1,3-glucan).

In alternative embodiments, a composition comprising poly-alpha-1,3-glucan and/or a poly-alpha-1,3-glucan ether compound of the present disclosure may be non-aqueous (eg, a dry composition). . Examples of these embodiments include powders, granules, microcapsules, flakes, or any other form of particulate material. Other examples include larger compositions such as pellets, sticks, beads, microspheres, tablets, sticks, or other agglomerates. A non-aqueous or dry composition of the present disclosure typically comprises less than 3, 2, 1, 0.5 or 0.1% by weight of water.

A poly-alpha-1,3-glucan ether compound comprised in certain embodiments of the disclosed composition may be crosslinked using any means known in the art. Such crosslinks may be borate crosslinks, where, for example, the borate is from any boron-containing compound (eg, boric acid, diborates, tetraborates, pentaborates, polymeric compounds, such as Polybor®, acid polymeric compounds

<img file="MX373205B_D0035.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY boric, alkaline borates). Alternatively, crosslinks with polyvalent metals, such as titanium or zirconium, may be provided. Titanium crosslinks can be provided, for example, with the use of titanium-containing compounds IV, such as titaniumammonium lactate, titanium triethanolamine, titanium acetylacetonate, and polyhydroxylated titanium complexes. Zirconium crosslinks can be performed, for example, with zirconium-containing compounds IV such as zirconium lactate, zirconium carbonate, zirconium acetylacetonate, zirconium triethanolamine, zirconium diisopropylamine lactate, and zirconium polyhydroxy complexes. Still alternatively, crosslinks can be performed with any crosslinking agent described in US Pat. 4462917, 4464270, 4477360 and 4799550, incorporated herein by reference. A crosslinking agent (eg, borate) may be present in an aqueous composition of the present disclosure in a concentration of from about 0.2% to 20% by weight or from about 0.1, 0.2, 0.3, 0.4, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15 or 20% by weight, for example.

A poly-alpha-1,3-glucan ether compound described herein that is crosslinked typically has a higher viscosity in aqueous solution compared to its non-crosslinked counterpart. Also, a

<img file="MX373205B_D0036.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY A cross-linked poly-alpha-1,3-glucan ether compound may have greater dilatant behavior compared to its non-cross-linked counterpart. For example, a borate crosslinked hydroxyalkyl poly-alpha-1,3-glucan ether compound (eg, dihydroxypropyl glucan ether) may have greater swelling behavior compared to its uncrosslinked counterpart.

A composition of the present disclosure may optionally contain one or more active enzymes. Non-limiting examples of suitable enzymes include proteases, cellulases, hemicellulases, peroxidases, lipolytic enzymes (eg metalolipolytic enzymes), xylanases, lipases, phospholipases, esterases (eg aryl esterase, polyesterase), perhydrolases, cutinases, pectinases, pectate lyases. , mannanases, keratinases, reductases, oxidases (eg choline oxidase), phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, beta-glucanases, arabinosidases, hyaluronidases, chondroitinases, laccases, metalloproteinases, amadoriases, glucoamylases, arabinofuranosidases, phytases, isomerases, transferases, and amylases. If one or more enzymes are included, for example, the concentration of the enzyme(s) in a composition of the present disclosure is about 0.0001-0.1% by weight (eg, 0.01-0.03% by weight) of active enzyme (for

<img file="MX373205B_D0037.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY example, calculated as pure protein enzyme).

One or more cellulase enzymes may optionally be comprised in a composition described herein. A cellulase of the present disclosure may have endocellulase activity (EC 3.2.1.4), exocellulase activity (EC 3.2.1.91) or cellobiase activity (EC 3.2.1.21). A cellulase of the present disclosure is an active cellulase that has activity under conditions suitable to maintain cellulase activity; those skilled in the art will determine such suitable conditions. In addition to being capable of degrading cellulose, in certain embodiments, a cellulase can further degrade cellulose ether derivatives such as carboxymethylcellulose. Examples of cellulose ether derivatives that are not expected to be stable to cellulase are described in US Pat. 7012053, 7056880, 6579840, 7534759 and 7576048.

A cellulase of the present disclosure can be derived from any microbial source, such as a bacterium or fungus. Chemically modified cellulases or mutant cellulases developed by genetic engineering of proteins are included. Suitable cellulases include, but are not limited to, cellulases from the genera Bacillus, Pseudomonas, Streptomyces, Trichoderma, Humicola, Fusarium, Thielavia, and Acremonium. As other examples, a cellulase can be derived

<img file="MX373205B_D0038.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY of Humicola insolens, Myceliophthora thermophila or Fusarium oxysporum; these and other cellulases are described in US patent nos. 4435307, 5648263, 5691178, 5776757 and 7604974, incorporated herein by reference. Examples of cellulases from Trichoderma reesei are described in US patent nos. 4,689,297, 5,814,501, 5,324,649 and in International Patent Application Publication Nos. WO92/06221 and WO92/06165, incorporated herein by reference. Examples of cellulases from Bacillus are described in US patent no. 6562612, incorporated herein by reference. A cellulase, such as any of the foregoing, is preferably in a mature form and lacks an N-terminal signal peptide. Commercially available cellulases useful in the present disclosure include CELLUZYME® and CAREZYME® (Novozymes A/S); CLAZINASE® and PURADAX® HA (DuPont Industrial Biosciences) and KAC-500(B)® (Kao Corporation).

Alternatively, a cellulase of the present disclosure can be made by any means known in the art, such as described in US patent nos. 4435307, 5776757 and 7604974, incorporated herein by reference. For example, a cellulase can be produced recombinantly in a

<img file="MX373205B_D0039.tif" />

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY heterologous expression system, such as a microbial or fungal heterologous expression system. Examples of heterologous expression systems include bacterial (eg, E. coli, Bacillus sp.) and eukaryotic systems. Eukaryotic systems may employ yeast (eg Pichia sp., Saccharomyces sp.) or fungal (eg Trichoderma sp. such as T. reesei, Aspergillus species such as A. Niger), for example.

One or more cellulases may be added directly as an ingredient when preparing the disclosed composition. Alternatively, one or more cellulases may be provided indirectly (inadvertently) in the disclosed composition. For example, cellulase may be provided in a composition of the present disclosure by virtue of being present in a non-cellulase enzyme preparation used to prepare the composition. Cellulase in compositions in which cellulase is indirectly provided therein may be present at a concentration of about 0.1-10 ppb (eg, less than 1 ppm), for example. A benefit of the composition of the present disclosure, by virtue of employing a poly-alpha-1,3-glucan ether compound instead of a cellulose ether compound, is that non-cellulase enzyme preparations could be used without being nullified. the desired effects of the glucan ether by the

<img file="MX373205B_D0040.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY background cellulase activity.

In certain embodiments, a cellulase can be thermostable. Cellulase thermostability refers to the enzyme's ability to retain activity after exposure to elevated temperature (eg, approximately 60-70°C) for a period of time (eg, approximately 30-60 minutes). ). The thermostability of a cellulase can be measured by its half-life (tl/2) in minutes, hours or days, during which half of the cellulase activity is lost under defined conditions.

In certain embodiments, a cellulase can be stable over a wide range of pH values ​​(eg, neutral or alkaline pH, such as -7.0 to -11.0 pH). The enzymes may be stable for a predetermined period of time (eg, at least about 15 min, 30 min, or 1 hour) under such pH conditions.

At least one, two or more cellulases may be included in the composition, for example. The total amount of cellulase in a composition of the present disclosure is typically an amount adequate for the cellulase to be used in the composition (an effective amount). For example, an effective amount of cellulase in a composition intended to improve the feel and/or appearance of a cellulose-containing fabric is an amount that produces measurable improvements in the

<img file="MX373205B_D0041.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY feel of the fabric to the touch (for example, improve the uniformity and/or appearance of the fabric, remove pills and fibrils that tend to reduce the definition of the appearance of the fabric). As another example, an effective amount of cellulase in a fabric stonewashing composition of the present disclosure is that amount which will provide the desired effect (for example, to produce a faded, worn appearance in seams and on fabric panels). . The amount of cellulase in a composition of the present disclosure, for example, may further depend on the parameters of the process in which the composition is used (for example, equipment, temperature, time, and the like) and the activity of the cellulase. cellulase. One skilled in the art can readily determine the effective concentration of cellulase in an aqueous composition in which a fabric is treated. In fabric care processes, for example, cellulase may be present in an aqueous composition (eg, wash liquor), in which a fabric is treated to a minimum concentration of approximately 0.01-0.1 ppm total cellulase protein. or about 0.1-10 ppb total cellulase protein (eg, less than 1 ppm) to a maximum of about 100, 200, 500, 1000, 2000, 3000, 4000 or 5000 ppm total cellulase protein.

The poly-alpha-1,3-glucan and/or poly-alpha-1,3-glucan ethers of the present disclosure are mostly o

<img file="MX373205B_D0042.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY completely stable (resistant) to degradation by cellulase. For example, the percentage degradation of a poly-alpha-1,3-glucan and/or poly-alpha-1,3-glucan ether compound by one or more cellulases is less than 10%, 9%, 8 %, 7%, 6%, 5%, 4%, 3%, 2% or 1% or is 0%. Such percentage degradation can be determined, for example, by comparing the molecular weight of the polymer before and after treatment with a cellulase over a period of time (eg, ~24 hours).

The examples described in the present description demonstrate that the hydrocolloids and aqueous solutions of the invention can have pseudoplastic behavior or dilatant behavior. The pseudoplastic behavior is observed as a decrease in the viscosity of the hydrocolloid or aqueous solution as the shear rate increases, while the dilatant behavior is observed as an increase in the viscosity of the hydrocolloid or aqueous solution as the shear rate increases. The modification of the shear thinning behavior or swelling behavior of an aqueous solution of the present description is due to the mixing of a poly-alpha-1,3-glucan ether composition in the aqueous composition. Thus, one or more poly-alpha-1,3-glucan ether compounds of the invention may be added to an aqueous composition to modify its rheological profile (i.e.,

<img file="MX373205B_D0043.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY modify the flow properties of the aqueous liquid, solution or mixture). In addition, one or more poly-alpha-1,3-glucan ether compounds of the present invention may be added to an aqueous composition to modify its viscosity.

The rheological properties of the hydrocolloids and aqueous solutions of the invention can be observed by measuring the viscosity during increasing rotary shear rate (eg, from about 10 rpm to about 250 rpm). For example, shear thinning behavior of a hydrocolloid or aqueous solution described herein can be observed as a reduction in viscosity (cps) of at least about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or 95% (or any whole number between 5% and 95% ) as the rotary cutting speed increases from approximately 0 rpm to 60 rpm, 10 rpm to 150 rpm, 10 rpm to 250 rpm, 60 rpm to 150 rpm, 60 rpm to 250 rpm or 150 rpm to 250 rpm. As another example, the dilatant behavior of a hydrocolloid or aqueous solution described herein can be observed as an increase in viscosity (cps) of at least about 5%, 10%, 15%, 20%, 25%, 30% , 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 100%, 125%, 150%, 175 % or 200% (or any whole number between 5% and 200%) according to

<img file="MX373205B_D0044.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY increases the rotary cutting speed from approximately 0 rpm to 60 rpm, 10 rpm to 150 rpm, 10 rpm to 250 rpm, 60 rpm to 150 rpm, 60 rpm to 250 rpm, or 150 rpm to 250 rpm.

A hydrocolloid or aqueous solution described herein may be in the form of, and/or comprised of, a personal care product, pharmaceutical product, food product, household product, or industrial product. The poly-alpha-1,3-glucan and/or poly-alpha-1,3-glucan ether compounds of the present disclosure can be used as thickening agents and/or dispersing agents in each of these products. Such thickening agent may be used in combination with one or more other types of thickening agents if desired, such as those described in US patent no. 8541041, the disclosure of which is incorporated herein by reference.

The personal care products of the present disclosure are not particularly limited and include, for example, skin care compositions, cosmetic compositions, antifungal compositions, and antibacterial compositions. The personal care products of the present description can be, for example, in the form of lotions, creams, pastes, balms, ointments, salves, gels, liquids, combinations of these and the like. The personal care products described

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY in the present description may include at least one active ingredient, if desired. An active ingredient is generally recognized as an ingredient that causes a desired pharmacological effect.

In certain embodiments, a skin care product can be applied to the skin to treat skin lesions related to lack of moisture. A skin care product may additionally be used to treat the visual appearance of the skin (for example, reducing the appearance of scaly, cracked, and/or reddened skin) and/or the feel of the skin to the touch (for example, reduce the roughness and/or dryness of the skin and, at the same time, improve the smoothness and delicacy of the skin). A skin care product may typically include at least one active ingredient for the treatment or prevention of skin conditions, and to provide a cosmetic effect, or to provide a moisturizing benefit to the skin, such as rust zinc, petrolatum, white petrolatum, mineral oil, cod liver oil, lanolin, dimethicone, solid fat, vitamin A, allantoin, calamine, kaolin, glycerin, or colloidal oatmeal, and combinations of these. A skin care product may include one or more natural moisturizing factors, such as ceramides, hyaluronic acid, glycerin, squalene, amino acids, cholesterol,

<img file="MX373205B_D0046.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY fatty acids, triglycerides, phospholipids, glycosphingolipids, urea, linoleic acid, glycosaminoglycans, mucopolysaccharide, sodium lactate or sodium pyrrolidinone carboxylate, for example. Other ingredients that may be included in a skin care product include, but are not limited to, glycerides, apricot kernel oil, canola oil, squalane, squalene, coconut oil, corn oil, jojoba oil, jojoba wax, lecithin, olive oil, safflower oil, sesame oil, shea butter, soybean oil, sweet almond oil, sunflower oil, tea plant oil, shea butter, palm oil, cholesterol, cholesterol esters, wax esters, fatty acids and orange oil.

A personal care product of the present description may, for example, also be in the form of makeup, lipstick, mascara, rouge, foundation, blush, eyeliner, lip liner, lip gloss, etc. cosmetics, sunscreen, sunblock, nail polish, styling mousse, hairspray, styling gel, nail conditioner, body wash, shower gel, body wash, face wash, shampoo, hair conditioner (to apply without rinsing or to remove by rinsing), cream rinse, hair dye, product

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY for hair dye, product to add shine to hair, hair serum, anti-frizz product for hair, product to repair split ends, lip balm, skin conditioner, cold cream, moisturizer , body spray, soap, scrub cream, scrub, astringent, face and neck lotion, depilatory product, permanent waving solution, anti-dandruff formulation, antiperspirant composition, deodorant, shaving product, pre-shave product, after-shave product, cleanser, skin gel, rinse, dentifrice composition, toothpaste or mouthwash.

A pharmaceutical of the present disclosure, for example, may be in the form of an emulsion, liquid, elixir, gel, suspension, solution, cream, or ointment. In addition, a pharmaceutical product of the present description can be in the form of any of the personal care products described in the present description, such as an antibacterial or antifungal composition. A pharmaceutical product may further comprise one or more pharmaceutically acceptable carriers, diluents and/or pharmaceutically acceptable salts. A polyalpha-1,3-glucan ether compound described in the present disclosure can further be used in capsules, encapsulants, tablet coatings, and as carriers for medicaments and drugs.

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

Non-limiting examples of food products of the present description include vegetables, meat, and soy patties; reformed shellfish; reformed cheese sticks; cream soups; broths and sauces; salad dressing; Mayonnaise; onion rings; jams, jellies and syrups; cake fillings; potato products, such as French fries and extruded potato chips; batters for fried foods, pancakes/waffles and cakes; pet food; beverages; frozen desserts; frozen; cultured dairy products, such as cottage cheese, yogurt, cheeses, and sour creams; coatings and icings for cakes; whipped cream; leavened or unleavened baked goods; and the like.

The poly-alpha-1,3-glucan and/or polyalpha-1,3-glucan ether compounds, hydrocolloids, and aqueous compositions described herein may be used to provide one or more of the following physical properties to a food product (or to any personal care product, pharmaceutical product or industrial product): thickening, freeze/thaw stability, lubricity, moisture retention and release, texture, consistency, shape retention, emulsification, binding, suspension, dispersion and gelation, for example. The poly-alpha-1,3-glucan and/or poly-alpha-1,3-glucan ether compounds described herein can typically be used in a

<img file="MX373205B_D0049.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY food product at a level of about 0.01 to about 5% by weight, for example.

A poly-alpha-1,3-glucan and/or a poly-alpha-1,3-glucan ether compound described in the present description may be contained in a food product or other edible material (for example, enteral pharmaceutical preparation ) in an amount that provides the desired degree of thickening and/or dispersion. For example, the concentration or amount of a poly-alpha-1,3-glucan and/or poly-alpha-1,3-glucan ether compound in a product, on a weight basis, may be about 0.1-3 % by weight, 0.1-4% by weight, 0.1-5% by weight or 0.1-10% by weight.

A domestic and/or industrial product of the present disclosure may be in the form of drywall tape-gasket composites; mortars; grouts; cement plaster; gypsum powder; cement stucco; adhesives; pasta; wall/ceiling texturizers; binders and processing aids for tape casting, extrusion forming, injection molding and ceramics; spraying of adherents and suspension/dispersion aids for pesticides, herbicides and fertilizers; fabric care products, such as fabric softeners and laundry detergents; hard surface cleaners; environmental modifiers; polymer emulsions; gels, such as water-based gels; surfactant solutions; paintings such as

<img file="MX373205B_D0050.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY water-based paints; protective coatings; adhesives; sealants and putties; inks such as water-based ink; metalworking fluids; emulsion based metal cleaning fluids used in electroplating, phosphating, galvanizing and/or general metal cleaning operations; hydraulic fluids (for example, those used for fracturing in downhole operations); and aqueous mineral slurries, for example.

A poly-alpha-1,3-glucan and/or a poly-alpha-1,3-glucan ether compound described in the present description may be contained in a personal care product, pharmaceutical product, household product or product. industrial in an amount that provides the desired degree of thickening or dispersion, for example. Examples of a concentration or amount of a poly-alpha-1,3-glucan ether compound in a product, based on weight, may be about 0.1-3% by weight, 1-2% by weight, 1.5 -2.5 wt%, 2.0 wt%, 0.1-4 wt%, 0.1-5 wt% or 0.1-10 wt%.

The compositions described herein may be in the form of a fabric care composition. A fabric care composition of the present disclosure can be used for hand washing, machine washing, and/or other purposes such as soaking and/or pretreating fabrics, for example. A composition

<img file="MX373205B_D0051.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY for fabric care can take, for example, the form of a laundry detergent; fabric conditioner; any product that is added to the wash, rinse or dryer; unit dose; or sprinkled. Fabric care compositions in liquid form may be in the form of an aqueous composition as described herein. In other aspects, a fabric care composition can be in dry form, such as a granular detergent or fabric softener canvas that is added in the dryer. Other non-limiting examples of fabric care compositions of the present disclosure include high performance or multi-purpose powdered or granular laundry agents; multi-purpose or high-performance liquid, gel or paste washing agents; liquid or dry detergents for fine fabrics (eg delicates); cleaning aids, such as bleach additives, spot cleaner sticks, or pre-treatments; products loaded on substrates such as dry and moistened cloths, pads or sponges; sprays and atomizers.

A detergent composition of the present disclosure may be in any useful form, for example, as a powder, granule, paste, stick, unit dose or liquid. A liquid detergent may be aqueous, typically containing up to about 70 wt% water and 0 wt% to about 30 wt% organic solvent. Also,

<img file="MX373205B_D0052.tif" />

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INSTITUTO MEXICANO DE LA PROPERDAD INDUSTRIAL may be in the form of a compact gel type containing only about 30% by weight of water.

A detergent composition of the present disclosure typically comprises one or more surfactants, wherein the surfactant is selected from nonionic surfactants, anionic surfactants, cationic surfactants, ampholytic surfactants, zwitterionic surfactants, semipolar nonionic surfactants, and mixtures of these. In some embodiments, the surfactant is present at a level of from about 0.1% to about 60%, while in alternative embodiments the level is from about 1% to about 50%, while in still other embodiments the level is about 5%. to about 40%, by weight of the detergent composition. A detergent will usually contain from 0% by weight to about 50% by weight of an anionic surfactant, such as linear alkylbenzenesulfonate (LAS), alphaolefinsulfonate (AOS), alkyl sulfate (fatty alcohol sulfate) (AS), sodium ethoxysulfate, alcohol (AEOS or AES), secondary alkanesulfonates (SAS), alpha-sulfo fatty acid methyl esters, alkyl or alkenyl succinic acid or soap. In addition, a detergent composition may optionally contain from 0% by weight to about 40% by weight of a nonionic surfactant, such as alcohol ethoxylate (AEO or AE), carboxylated alcohol ethoxylates, alcohol ethoxylate

<img file="MX373205B_D0053.tif" />

' IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY nonylphenol, alkylpolyglycoside, alkyldimethylamine oxide, ethoxylated fatty acid monoethanolamide, fatty acid monoethanolamide, or polyhydroxyalkyl fatty acid amide (as described, for example, in patent no. WO92/06154, incorporated in the this description for reference).

A detergent composition of the present disclosure typically comprises one or more detergent additives or additive systems. In some embodiments that include at least one builder, the cleaning compositions comprise at least about 1%, from about 3% to about 60%, or even from about 5% to about 40% builder by weight of the composition. Builders include, but are not limited to, alkali metals, ammonium and alkanolammonium salts of polyphosphates, alkali metal silicates, alkaline earth and alkali metal carbonates, aluminosilicates, polycarboxylate compounds, ether hydroxypolycarboxylates, copolymers of maleic anhydride with ethylene or vinyl methyl ether, 1,3,5-trihydroxy benzene-2,4,6-trisulfonic acid and carboxymethyloxy succinic acid, various alkali metal salts, ammonium and substituted ammonium polyacetic acids, such as ethylenediaminetetraacetic acid and nitrilotriacetic acid, as well as polycarboxylates such as mellitic acid, succinic acid, citric acid, oxydisuccinic acid, polymaleic acid, benzene acid 1,3,5373205

<img file="MX373205B_D0054.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY tricarboxylic, carboxymethyloxysuccinic acid and soluble salts thereof. Indeed, it is contemplated that any suitable enhancer will be useful in various embodiments of the present invention. Examples of a complexing agent or detergent builder include zeolite, diphosphate, triphosphate, phosphonate, citrate, nitrilotriacetic acid (NTA), ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTMPA), alkyl or alkenyl succinic acid, soluble silicates or layered silicates (eg SKS-6 ex Hoechst). Furthermore, a detergent may contain no additives, ie it may be essentially free of detergent additive.

In some embodiments, builders form water-soluble hardness ion complexes (eg, sequestering builders), such as citrates and polyphosphates (eg, sodium tripolyphosphate and sodium tripolyphosphate hexahydrate, potassium tripolyphosphate and mixture of sodium and potassium tripolyphosphate, etc. .). Any suitable builder is contemplated to be useful in the present invention and these include those known in the art (see, for example, European Patent No. EP2100949).

In some embodiments, builders for use in the present disclosure include phosphate builders and non-phosphate builders. In some embodiments, the builder is a phosphate builder. In some modes, the

<img file="MX373205B_D0055.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY Improver is an improver without phosphate. If present, builders are used at a level of from 0.1% to 80% or from 5% to 60% or from 10% to 50%, by weight of the composition. In some embodiments, the product comprises a mixture of phosphate and non-phosphate builders. Suitable phosphate builders include oligomeric monophosphates, diphosphates, tripolyphosphates, or polyphosphates, including the alkali metal salts of these compounds, including the sodium salts. In some embodiments, a builder can be sodium tripolyphosphate (STPP). In addition, the composition may comprise carbonate and/or citrate, preferably citrate which helps to achieve a neutral pH composition. Other suitable non-phosphate builders include homopolymers and copolymers of polycarboxylic acids and their partially or fully neutralized salts, the monomeric polycarboxylic acids, and the hydroxycarboxylic acids and their salts. In some embodiments, salts of the aforementioned compounds include ammonium and/or alkali metal salts, ie lithium, sodium and potassium salts, including sodium salts. Suitable polycarboxylic acids include cyclic, alicyclic, heterocyclic, and aromatic carboxylic acids, where, in some embodiments, they may contain at least two carboxyl groups, which, in this case, are separated from each other, in some cases, by no more than two. carbon atoms.

<img file="MX373205B_D0056.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

A detergent composition of the present disclosure may comprise at least one chelating agent. Suitable chelating agents include, but are not limited to, copper, iron and/or manganese chelating agents and mixtures of these. In embodiments in which at least one chelating agent is used, the composition comprises from about 0.1% to about 15% or even from about 3.0% to about 10% chelating agent by weight of the composition.

A detergent composition of the present disclosure may comprise at least one deposition agent. Suitable deposition aids include, but are not limited to, polyethylene glycol, polypropylene glycol, polycarboxylate, soil release polymers such as polyterephthalic acid, clays such as kaolinite, montmorillonite, attapulgite, illite, bentonite, halloysite, and mixtures of these.

A detergent composition of the present disclosure may comprise one or more dye transfer inhibiting agents. Suitable polymeric dye transfer inhibiting agents include, but are not limited to, polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, polyvinyloxazolidones and polyvinylimidazoles, or mixtures of these. Transfer inhibitor agents

<img file="MX373205B_D0057.tif" />

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Additional dyestuffs include phthalocyanine, peroxidases, polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and Nvinylimidazole, polyvinyloxazolidones and polyvinylimidazoles and/or mixtures of these, examples of chelating agents including acid ethylenediaminetetraacetic acid (EDTA); diethylenetriamine pentamethylene phosphonic acid (DTPMP); hydroxyethane diphosphonic acid (HEDP); ethylenediamine-N,N' disuccinic acid (EDDS); methylglycinediacetic acid (MGDA); diethylenetriamine pentaacetic acid (DTPA); propylene diamine tetraacetic acid (PDT A); 2-hydroxypyridine-N-oxide (HPNO); or methylglycinediacetic acid (MGDA); glutamic acid-N,N-diacetic acid (N,N-dicarboxymethyl glutamic acid tetrasodium salt (GLDA); nitrilotriacetic acid (NTA); 4,5-dihydroxy-m-benzenesulfonic acid; citric acid and any salts thereof; N-hydroxyethylethylenediaminetriacetide acid (HEDTA), triethylenetetraaminehexaacetic acid (TTHA), Nhydroxyethyliminodiacetic acid (REIDA), dihydroxyethylglycine (DHEG), ethylenediaminetetrapropionic acid (EDTP), and derivatives thereof, which may be used alone or in combination with any of the foregoing. In embodiments in which at least one dye transfer inhibiting agent is used, a composition of the present disclosure may comprise from about 0.0001% to about 10%, from about 0.01% to about 5%, or even

<img file="MX373205B_D0058.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY approximately 0.1% to approximately 3%, by weight of the composition.

A detergent composition of the present disclosure may comprise silicates. In some of these embodiments, sodium silicates (eg, sodium disilicate, sodium metasilicate, and/or crystalline phyllosilicates) are used. In some embodiments, silicates are present at a level of from about 1% to about 20% by weight of the composition. In some embodiments, silicates are present at a level of from about 5% to about 15% by weight of the composition.

A detergent composition of the present disclosure may comprise dispersants. Suitable water-soluble organic materials include, but are not limited to, homo or copolymeric acids or their salts, in which the polycarboxylic acid comprises at least two carboxyl radicals separated from each other by not more than two carbon atoms.

A detergent composition of the present disclosure may further comprise one or more enzymes. Examples of enzymes include proteases, cellulases, hemicellulases, peroxidases, lipolytic enzymes (eg, metallopolytic enzymes), xylanases, lipases, phospholipases, esterases (eg, arylesterase, polyesterase), perhydrolases, cutinases, pectinases, pectate lyases,

<img file="MX373205B_D0059.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY mannanases, keratinases, reductases, oxidases (for example, choline oxidase, phenoloxidase), phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, beta-glucanases, arabinosidases, hyaluronidases, chondroitinases, laccases, metalloproteinases , amaromas, glucoamylases, alpha-amylases, beta-amylases, galactosidases, galactanases, catalases, carageenases, hyaluronidases, keratinases, lactases, ligninases, peroxidases, phosphatases, polygalacturonases, pullulanases, rhamnogalacturonases, tannases, transglutaminases, xyloglucanases, xylosidases, metalloproteinases, arabinofuranosidases, phytases, isomerases, transferases, and/or amylases in any combination.

Any cellulase described above is contemplated for use in the detergent compositions described. Suitable cellulases include, but are not limited to, cellulases from Humicola insolens (see, eg, US Pat. No. 4,435,307). Illustrative cellulases contemplated for use herein are those that have a color care benefit for a fabric. Examples of cellulases that offer a color care benefit are described in US Pat. EP0495257, EP0531372, EP531315, WO96/11262, WO96/29397, WO94/07998; patent no. WO98/12307; WO95/24471, WO98/08940 and US Pat. 5,457,046, 5,686,593, and 5,763,254, all incorporated herein by reference. The examples of

<img file="MX373205B_D0060.tif" />

IMPI

Commercially available cellulases useful in a detergent include CELLUSOFT®, CELLUCLEAN®, CELLUZYME® and CAREZYME® (Novo Nordisk A/S and Novozymes A/S); CLAZINASE®, PURADAX HA® and REVITALENZ™ (DuPont Industrial Biosciences); BIOTOUCH® (AB Enzymes); and KAC-500(B)™ (Kao Corporation). Additional cellulases are described, for example, in US patent nos. US7595182, US8569033, US7138263, US3844890, US4435307 and US4435307 and in Great Britain patent no. GB2095275.

In some embodiments of the present invention, the detergent compositions of the present invention may comprise one or more enzymes, each at a level of from about 0.00001% to about 10% by weight of the composition and the cleaning accessory materials qsp by weight. of the composition. In other embodiments of the present invention, the detergent compositions further comprise each enzyme at a level of from about 0.0001% to about 10%, from about 0.001% to about 5%, from about 0.001% to about 2%, from about 0.005 % to about 0.5% enzyme by weight of the composition.

Suitable proteases include those of animal, plant or microbial origin. In some embodiments, microbial proteases are used. In some embodiments, chemically or genetically modified mutants are included. In some

<img file="MX373205B_D0061.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY modalities, the protease is a serine protease, preferably an alkaline microbial protease or a trypsin-type protease. Examples of alkaline proteases include subtilisins, especially those derived from Bacillus (eg, subtilisin, lentus, amyloliquefaciens, subtilisin Carlsberg, subtilisin 309, subtilisin 147, and subtilisin 168). Additional examples include those mutant proteases described in US patent nos. RE34606, 5955340, 5700676, 6312936 and 6482628, all of them incorporated in the present description by reference. Examples of additional proteases include, but are not limited to, trypsin (eg, of porcine or bovine origin) and the Fusarium protease described in US Pat. WO89/06270. In some embodiments, commercially available protease enzymes include, but are not limited to, MAXATASE®, MAXACAL™, MAXAPEM™, OPTICLEAN®, OPTIMASE®, PROPERASE®, PURAFECT®, PURAFECT® OXP, PURAMAX™, EXCELLASE™, PREFERENZ proteases ™ (eg P100, P110, P280), EFFECTENZ™ proteases (eg P1000, P1050, P2000), EXCELLENZ™ proteases (eg P1000), ULTIMASE® and PURAFAST™ (Genencor); ALCALASE®, SAVINASE®, PRIMASE®, DURAZYM™, POLARZYME®, OVOZYME®, KANNASE®, LIQUANASE®, NEUTRASE®, RELASE®, and ESPERASE® (Novozymes); BLAP™ and BLAP™ variants (Henkel Kommanditgesellschaft auf Aktien, Duesseldorf, Germany) and

<img file="MX373205B_D0062.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

KAP (B. alkalophilus subtilisin; Kao Corp., Tokyo, Japan). Various proteases are described in US Pat. WO95/23221, WO92/21760, WO09/149200, WO09/149144, WO09/149145, WO11/072099, WO10/056640, WO10/056653, WO11/140364, WO12/151534 and in US Patent Publication no. 2008/0090747 and US patent nos. 5801039, 5340735, 5500364, 5855625, RE34606, 5955340, 5700676, 6312936, 6482628, 8530219, and various other patents. In some other embodiments, neutral metalloproteases are useful in the present invention, and include, but are not limited to, the neutral metalloproteases described in US Pat. WO1999014341, WO1999033960, WO1999014342, WO1999034003, WO2007044993, WO2009058303 and WO2009058661, all of them incorporated in the present description by reference. Illustrative metalloproteases include, nprE, the recombinant form of neutral metalloprotease expressed in Bacillus subtilis (see, eg, Patent No. WO07/044993), and PMN, the purified neutral metalloprotease from Bacillus amyloliquefaciens.

Suitable mannanases include, but are not limited to, those of bacterial or fungal origin. In some embodiments, chemically or genetically modified mutants are included. Various mannanases are known to be useful in the present invention (see, for example, US Pat. Nos. 6,566,114, 6,602,842, and 6,440,991, all of which are incorporated herein).

<img file="MX373205B_D0063.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY present description as reference). Commercially available mannanases useful in the present invention include, but are not limited to, MANNASTAR®, PURABRITE™ and MANNAWAY®.

Suitable lipases include those of bacterial or fungal origin. Included are modified, chemically modified, or proteolytically modified protein mutants. Examples of useful lipases include those from the genera Humicola (for example, H. lanuginosa, European Patent Nos. EP258068 and EP305216; H. insolens, Patent No. WO96/13580), Pseudomonas (for example, P. alcaligenes or P. pseudoalcaligenes, European Patent No. EP218272; P. cepacia, European Patent No. EP331376; P. stutzeri, Great Britain patent no. GB1372034; P. fluorescens and Pseudomonas sp. strain SD 705, patent nos. WO95/06720 and WO96/27002; P. wisconsinensis, patent no. WO96/12012); and Bacillus (eg, B. subtilis, Dartois et al., Biochemica et Biophysica Acta 1131:253-360; B. stearothermophilus, Japanese Patent No. JP64/744992; B. pumilus, Patent No. WO91/16422). In addition, a number of cloned lipases are useful in some embodiments of the present invention, including, but not limited to, Penicillium camembertii lipase (see, Yamaguchi et al., Gene 103:61-67 [1991]), Geotricum candidum lipase ( see, Schimada et al., J. Biochem., 106:383-388 [1989]) and the various Rhizopus lipases such as lipase R.

<img file="MX373205B_D0064.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY delemar (see, Hass et al., Gene 109:117-113 [1991]), an R. niveus lipase (Kugimiya et al., Biosci. Biotech. Biochem. 56:716-719 [1992 ]) and R. oryzae lipase. Other lipases useful in the present disclosure include, for example, those described in US Pat. WO92/05249, WO94/01541, WO95/35381, WO96/00292, WO95/30744, WO94/25578, WO95/14783, WO95/22615, WO97/04079, WO97/07202, and in European patent nos. EP407225 and EP260105. Other types of lipase polypeptide enzymes such as cutinases are also useful in some embodiments of the present invention, and include, but are not limited to, cutinase derived from Pseudomonas mendocina (see, patent no. WO88/09367) and cutinase derived from Fusarium solani pisi (see, patent no. WO90/09446). Examples of certain commercially available lipase enzymes useful in the present disclosure include MI LIPASE™, LUMA FAST™ and LIPOMAX™ (Genencor); LIPEX®, LIPOLASE® and LIPOLASE® ULTRA (Novozymes); and LIPASE P™ Amano (Amano Pharmaceutical Co. Ltd., Japan).

Suitable polyesterases include, for example, those described in US Pat. WO01/34899 and WO01/14629 and in US patent no. 6933140.

A detergent composition of the present description may further comprise 2,6-beta-D-fructan hydrolase, which is effective in removing/cleaning certain biofilms present in home and/or industrial textiles/clothes.

<img file="MX373205B_D0065.tif" />

IMPI

Suitable amylases include, but are not limited to, those of bacterial or fungal origin. In some embodiments, chemically or genetically modified mutants are included. Amylases useful in the present invention include, but are not limited to, alpha-amylase obtained from B.

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

<td colspan="3">licheniformis (see, for example, the no. GB1296839). Other amylases</td><td>britain patent suitable include the</td>

<td colspan="2">described in patents</td><td>no.</td><td>W09510603, WO9526397,</td>

<td>WO9623874,</td><td colspan="2">WO9623873, WO9741213,</td><td>WO9919467, WO0060060,</td>

<td>WO0029560,</td><td colspan="2">WO9923211, WO9946399,</td><td>WO0060058, WO0060059,</td>

<td>WO9942567,</td><td colspan="2">WO0114532, WO02092797,</td><td>WO0166712, WO0188107,</td>

<td>WO0196537,</td><td colspan="2">WO0210355, WO9402597,</td><td>WO0231124, WO9943793,</td>

<td>WO9943794,</td><td>WO2004113551,</td><td colspan="2">WO2005001064, WO2005003311,</td>

<td>WO0164852,</td><td>WO2006063594,</td><td colspan="2">WO2006066594, WO2006066596,</td>

<td>WO2006012899</td><td>, WO2008092919,</td><td colspan="2">WO2008000825, WO2005018336,</td>

<td>WO2005066338</td><td>, WO2009140504,</td><td colspan="2">WO2005019443, WO2010091221,</td>

<td>WO2010088447</td><td>, WO0134784,</td><td colspan="2">WO2006012902, WO2006031554,</td>

<td>WO2006136161</td><td>, WO2008101894,</td><td colspan="2">WO2010059413, WO2011098531,</td>

<td>WO2011080352</td><td>, WO2011080353,</td><td colspan="2">WO2011080354, WO2011082425,</td>

<td>WO2011082429</td><td>, WO2011076123,</td><td colspan="2">WO2011087836, WO2011076897,</td>

WO94183314, WO9535382, WO9909183, WO9826078, WO9902702,

WO9743424, WO9929876, WO9100353, WO9605295, WO9630481,

WO9710342, WO2008088493, WO2009149419, WO2009061381,

WO2009100102, WO2010104675, WO2010117511 and WO2010115021, all incorporated in the present description as

<img file="MX373205B_D0066.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY reference.

Suitable amylases include, for example, commercially available amylases such as STAINZYME®, STAINZYME PLUS®, NATALASE®, DURAMYL®, TERMAMYL®, TERMAMYL ULTRA®, FUNGAMYL® and BAN™ (Novo Nordisk A/S and Novozymes A/S ); RAPIDASE®, POWERASE®, PURASTAR® and PREFERENZ™ (DuPont Industrial Biosciences).

Suitable peroxidases/oxidases contemplated for use in the compositions include those of plant, bacterial or fungal origin. Chemically modified or modified protein mutants are included. Examples of peroxidases useful in the present description include those of the genus Coprinus (eg, C. cinereus, patent nos. WO93/24618, WO95/10602 and WO98/15257), in addition to those mentioned in patent nos. WO2005056782, WO2007106293, WO2008063400, WO2008106214 and WO2008106215. Commercially available peroxidases useful in the present disclosure include, for example, GUARDZYME™ (Novo Nordisk A/S and Novozymes A/S).

In some embodiments, peroxidases are used in conjunction with hydrogen peroxide or a source thereof (eg, a percarbonate, perborate, or persulfate) in the compositions of the present invention. In some alternative embodiments, oxidases are used in conjunction with oxygen. Both types of enzymes are used for solution bleaching (i.e.

<img file="MX373205B_D0067.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY say, to prevent the transfer of fabric dyes from one dyed fabric to another fabric when the fabrics are washed together in a washing liquid), preferably, together with an improving agent (see, for example, the patent nos. WO94/12621 and WO95/01426). Suitable peroxidases/oxidases include, but are not limited to, those of plant, bacterial or fungal origin. In some embodiments, chemically or genetically modified mutants are included.

Enzymes which may be comprised in a detergent composition of the present disclosure may be stabilized with the use of conventional stabilizing agents, for example, a polyol such as propylene glycol or glycerol; a sugar or sugar alcohol; lactic acid; boric acid or a derivative of boric acid (for example, an aromatic borate ester).

A detergent composition of the present disclosure may contain from about 1% by weight to about 65% by weight of a detergent builder or complexing agent such as zeolite, diphosphate, triphosphate, phosphonate, citrate, nitrilotriacetic acid (NTA), acid ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTMPA), alkyl or alkenyl succinic acid, soluble silicates or layered silicates (eg SKS-6 ex Hoechst). Furthermore, a detergent may contain no additives, i.e. it may be essentially free

<img file="MX373205B_D0068.tif" />

IMPI

MEXICAN INSTITUTE

OF THE PROPERTY

INDUSTRIAL detergent additive.

In certain embodiments, a detergent composition may comprise one or more different types of polymers in addition to a poly-alpha-1,3-glucan and/or poly-alpha-1,3-glucan ether compound. Examples of other types of polymers useful herein include carboxymethylcellulose (CMC), polyvinylpyrrolidone (PVP), polyethylene glycol (PEG), polyvinyl alcohol (PVA), polycarboxylates such as polyacrylates, maleic acid/ acrylic and lauryl methacrylate/acrylic acid copolymers.

A detergent composition of the present disclosure may contain a bleach system. For example, a bleach system may comprise a source of H2O2 such as perborate or percarbonate, which may be combined with a peracid-forming bleach activator such as tetraacetylethylenediamine (TAED) or nonanoyloxybenzenesulfonate (NOBS). Alternatively, a bleach system may comprise peroxyacids (for example, peroxyacids of the amide, imide, or sulphone type). Still alternatively, a bleach system may be an enzyme bleach system comprising perhydrolase, eg, such as the system described in US Pat. WO2005/056783.

A detergent composition of the present disclosure may further contain conventional detergent ingredients such as fabric conditioners,

<img file="MX373205B_D0069.tif" />

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY clays, foam boosters, foam reducers, anti-corrosion agents, dirt suspension agents, dirt anti-redeposition agents, dyes, bactericides, tarnish inhibitors, optical brighteners or perfumes. The pH of a detergent composition of the present disclosure (measured in aqueous solution at use concentration) is usually neutral or alkaline, eg, a pH of from about 7.0 to about 11.0).

Particular forms of detergent compositions that may be adapted for the purposes described herein are described, for example, in US Pat. US20090209445A1, US20100081598A1 and US7001878B2, European patent no. EP1504994B1, patents no. WO2001085888A2, WO2003089562A1, WO2009098659A1, WO2009098660A1, WO2009112992A1, WO2009124160A1, WO2009152031A1, WO2010059483A1, WO2010088112A1, WO2010090915A1, WO2010135238A1, WO2011094687A1, WO2011094690A1, WO2011127102A1, WO2011163428A1, WO2008000567A1, WO2006045391A1, WO2006007911A1, WO2012027404A1, EP1740690B1, WO2012059336A1, US6730646B1, WO2008087426A1, WO2010116139A1 y WO2012104613A1, all of them incorporated in the present description by reference.

The laundry detergent compositions of the present disclosure may optionally be heavy-duty (all-purpose) laundry detergent compositions.

<img file="MX373205B_D0070.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

Illustrative heavy duty laundry detergent compositions comprise a detergent surfactant (10%-40% w/w), including an anionic detergent surfactant (selected from the group of alkyl sulfates, alkyl sulfonates, alkyl alkoxylated sulfates, alkyl phosphates, alkyl phosphonates). substituted or unsubstituted straight or branched or random chain alkyl carboxylates and/or mixtures thereof) and, optionally, a nonionic surfactant (selected from the group of substituted or unsubstituted straight or branched or random chain alkyl alcohol alkoxylates, for example, C8-C18 alkyl alcohol ethoxylates and/or C6-C12 alkyl phenol alkoxylates), wherein the weight ratio of anionic detergent surfactant (with a hydrophilic index (HIc) of 6.0 to 9) to nonionic detergent surfactant is greater than 1:1. Suitable detergent surfactants further include cationic detergent surfactants (selected from the group of alkyl pyridinium compounds, alkyl quaternary ammonium compounds, alkyl quaternary phosphonium compounds, alkyl ternary sulfonium compounds, and/or mixtures thereof); zwitterionic and/or amphoteric detergent surfactants (selected from the group of alkanolamines and sulfobetaines); ampholytic surfactants; non-ionic semi-polar surfactants and mixtures of these.

A detergent of the present description such as a

<img file="MX373205B_D0071.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY High-performance laundry detergent composition may optionally include a surfactant-enhancing polymer consisting of amphiphilic alkoxylated grease-cleaning polymers (selected from the group of alkoxylated polymers having branched hydrophilic and hydrophobic properties, such as alkoxylated polyalkylenimines in the range of 0.05 wt% to 10 wt%) and/or random graft polymers (typically comprising a hydrophilic backbone comprising monomers selected from the group consisting of C1-C6 carboxylic acids unsaturated, ethers, alcohols, aldehydes, ketones, esters, sugar units, alkoxy units, maleic anhydride, saturated polyols, such as glycerol, and mixtures of these; and hydrophobic side chain(s) selected from the group consisting of: C4-C25 alkyl group, polypropylene, polybutylene, vinyl ester of a saturated C1-C6 monocarboxylic acid, C1-C6 alkyl ester of acrylic or methacrylic acid and mixtures of these.

A detergent of the present disclosure, such as a heavy duty laundry detergent composition, may optionally include additional polymers, such as soil release polymers (including anion-capped polyesters, e.g., SRP1, polymers comprising at least one monomer unit selected from

<img file="MX373205B_D0072.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY a saccharide, dicarboxylic acid, polyol and combinations of these, in a random or block configuration, polymers based on ethylene terephthalate and copolymers of these in a random or block configuration, for example, REPELO-TEX SF, SF-2 and SRP6, TEXCARE SRA100, SRA300, SRN100, SRN170, SRN240, SRN300 and SRN325, MARLOQUEST SL), anti-redeposition polymers (from 0.1 wt% to 10 wt%, including carboxylate polymers, such as polymers comprising at least one monomer selected from acrylic acid, maleic acid (or maleic anhydride), fumaric acid, itaconic acid, aconitic acid, mesaconic acid, citraconic acid, methylenemalonic acid, and any mixture of these, vinylpyrrolidone homopolymer, and/or polyethylene glycol, with a molecular weight in the range of 500 to 100,000 Da); and polymeric carboxylate (such as random maleate/acrylate copolymer or polyacrylate homopolymer).

A detergent of the present disclosure, such as a heavy duty laundry detergent composition, may optionally further include saturated or unsaturated fatty acids, preferably C12-C24 saturated or unsaturated fatty acids (from 0 to 10% by weight). % in weigh); deposition aids in addition to a poly-alpha-1,3-glucan ether compound described herein (examples of which include polysaccharides, polymers

<img file="MX373205B_D0073.tif" />

' IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY cellulosics, polydiallyl dimethylammonium halides (DADMAC) and DAD MAC copolymers with vinylpyrrolidone, acrylamides, imidazoles, imidazolinium halides and mixtures of these, in a random or block configuration, cationic guar gum, cationic starch , cationic polyacylamides and mixtures of these.

A detergent of the present disclosure, such as a heavy duty laundry detergent composition, may optionally further include dye transfer inhibiting agents, examples of which include manganese phthalocyanine, peroxidases, polyvinylpyrrolidone polymers, polymers of polyamine N-oxide, copolymers of N-vinylpyrrolidone and N-vinylimidazole, polyvinyloxazolidones and polyvinylimidazoles and/or mixtures of these; chelating agents, examples of which include ethylene diamine tetraacetic acid (EDTA), diethylene triamine pentamethylene phosphonic acid (DTPMP), hydroxy ethane diphosphonic acid (HEDP), ethylene diamine N,N'-disuccinic acid (EDDS), methyl glycine diacetic acid (MGDA), diethylenetriaminepentaacetic acid (DTPA), propylene diamine tetraacetic acid (PDTA), 2-hydroxypyridine N-oxide (HPNO) or methyl glycine diacetic acid (MGDA), glutamic acid N,N-diacetic acid (N,N-dicarboxymethyl glutamic acid tetrasodium salt (GLDA), nitrilotriacetic acid (NTA), 4,5-dihydroxy-m-benzenedisulfonic acid, citric acid and any salt

<img file="MX373205B_D0074.tif" />

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY of these, N-hydroxyethylethylenediaminetriacetic acid (HEDTA), triethylenetetraaminohexaacetic acid (TTHA), Nhydroxyethyliminodiacetic acid (HEIDA), dihydroxyethylglycine (DHEG), ethylenediaminetetrapropionic acid (EDTP), and derivatives thereof.

A detergent of the present disclosure such as a heavy duty laundry detergent composition may optionally include silicone or fatty acid based suds reducers; shading colorants, calcium and magnesium cations, visual signaling ingredients, antifoam (from 0.001 wt% to about 4.0 wt%) and/or a structuring/thickening agent (from 0.01 wt% to 5 wt%, selected from the group consisting of diglycerides and triglycerides, ethylene glycol distearate, microcrystalline cellulose, microfiber cellulose, biopolymers, xanthan gum, gellan gum, and mixtures of these). Such a structuring/thickening agent would be in addition to one or more poly-alpha-1,3-glucan compounds comprised in the detergent.

A detergent of the present disclosure may be in the form of a heavy duty dry/solid laundry detergent composition, for example. Such a detergent may include: (i) a detergent surfactant, such as any anionic detergent surfactant described herein, any non-detergent surfactant

<img file="MX373205B_D0075.tif" />

IMPI

INSTITUTO MEXICANO DE LA PROPERDAD INDUSTRIAL described in this description, any cationic detergent surfactant described in this description, any zwitterionic and/or amphoteric detergent surfactant described in this description, any ampholytic surfactant, any non-ionic semipolar surfactant, and mixtures of these; (ii) a builder, such as any non-phosphate builder (for example, zeolite builders in the range of 0wt% to less than 10wt%), any phosphate builder (for example, sodium tripolyphosphate in the range from 0% by weight to less than 10% by weight), citric acid, citrate salts and nitrilotriacetic acid, any silicate salts (for example, sodium or potassium silicate or sodium metasilicate in the range of 0% by weight to less than 10% by weight) ; any carbonate salt (eg sodium carbonate and/or sodium bicarbonate in the range of 0 wt% to less than 80 wt%) and mixtures of these; (iii) a bleaching agent, such as any photobleach (for example, sulfonated zinc phthalocyanines, sulfonated aluminum phthalocyanines, xanthene dyes, and mixtures thereof), any hydrophobic or hydrophilic bleach activator (for example, dodecanoyl oxybenzene sulfonate, decanoyl oxybenzene sulfonate, decanoyl oxybenzoic acid or salts thereof, 3,5,5-trimethyl hexanoyl oxybenzene sulfonate, tetraacetyl ethylenediamine-TAED, nonanoyloxybenenesulfonate373205

<img file="MX373205B_D0076.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

NOBS, quaternary nitrile, and mixtures thereof), any source of hydrogen peroxide (for example, inorganic perhydrate salts, examples of which include mono- or tetrahydrate sodium salt of perborate, percarbonate, persulfate, perphosphate, or persilicate), any hydrophilic peracid and/or preformed hydrophobic (eg, percarboxylic acids and salts, percarbonic acids and salts, perimidic acids and salts, peroxymonosulfuric acids and salts, and mixtures of these); and/or (iv) any other component, such as a bleach catalyst (eg, imine bleach boosters, examples of which include iminium polyions and cations, iminium zwitterions, modified amines, modified amine oxides, N-sulfonyl imines, N -phosphonyl imines, N-acyl imines, thiadiazole dioxides, perfluoroimines, cyclic sugar ketones, and mixtures of these), and a metal-containing bleach catalyst (for example, copper, iron, titanium, ruthenium, tungsten, molybdenum, or manganese cations together with an auxiliary metal cation, such as zinc or aluminum, and a sequestrant such as EDTA, ethylenediaminetetra(methylenephosphonic acid).

The compositions described herein may be in the form of a dishwashing detergent composition. Examples of dishwashing detergents include automatic dishwashing detergents (typically used in dishwashing machines) and

<img file="MX373205B_D0077.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY Detergents for manual dishwashing. A dishwashing detergent composition can be in either dry or liquid/aqueous form, as described herein, for example. Components that may be included in certain embodiments of a dishwashing detergent composition include, for example, one or more than one phosphate; oxygen or chlorine based bleaching agent; nonionic surfactant; alkali salt (eg metasilicates, alkali metal hydroxides, sodium carbonate); any active enzyme described in the present description; anti-corrosion agent (eg sodium silicate); antifoaming agent; additives to slow down the rate of removal of enamel and marks from ceramic elements; fragrance; anticaking agent (in granular detergents); starch (in tablet-based detergents); gelling agent (in liquid/gel based detergents); and/or sand (powder detergents).

Dishwashing detergents such as automatic dishwashing detergent or liquid dishwashing detergent may comprise (i) a nonionic surfactant, including any ethoxylated nonionic surfactant, alkoxylated alcohol surfactant, polyalcohol epoxy-capped (oxyalkylated) or amine oxide surfactant present in an amount of 0 to 10% by weight; (ii) an builder, in the range of about 5-60% by weight,

<img file="MX373205B_D0078.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY which includes any phosphate builder (for example, monophosphates, diphosphates, tripolyphosphates, other oligomeric polyphosphates, sodium tripolyphosphate-STPP), any non-phosphate builder (for example, amino acid-based compounds including methyl- glycine-diacetic acid [MGDA] and salts or derivatives thereof, glutamic-N,N-diacetic acid [GLDA] and salts or derivatives thereof, iminodisuccinic acid (IDS) and salts or derivatives thereof, carboxymethyl inulin and salts or derivatives thereof, nitrilotriacetic acid [NTA], diethylenetriamine pentaacetic acid [DTPA], Balaninadiacetic acid [B-ADA] and salts thereof), homopolymers and copolymers of polycarboxylic acids and partially or completely neutralized salts thereof, monomeric polycarboxylic acids and hydroxycarboxylic acids and salts thereof in the range of from 0.5 wt% to 50 wt% or carboxylated/sulfonated polymers in the range of about 0.1 wt% to about 50 wt%; (iii) a drying aid in the range of from about 0.1 wt% to about 10 wt% (eg, polyesters, especially anionic polyesters, optionally, together with additional monomers with 3 to 6 functional groups; typically acid, alcohol, or ester functional groups, leading to polycondensation; polyurethane and/or polyurea polyorganosiloxane compounds or precursor compounds thereof, particularly of the urea and cyclic carbonate type

<img file="MX373205B_D0079.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY reactive); (iv) a silicate, in the range of from about 1% by weight to about 20% by weight (eg, sodium or potassium silicates, such as sodium disilicate, sodium metasilicate, and crystalline phyllosilicates); (v) an inorganic bleach (for example, perhydrate salts such as perborate, percarbonate, perphosphate, persulfate, and persilicate salts) and/or an organic bleach (for example, organic peroxyacids, such as diacyl and tetraacyl peroxides, especially diperoxydodecanedioic acid , diperoxytetradecanedioic acid and diperoxyhexadecanedioic acid); (vi) a bleach activator (eg, organic peracid precursors in the range of from about 0.1 wt% to about 10 wt%) and/or bleach catalyst (eg, manganese triazacyclononane and related complexes; manganese bispyridylamine Co, Cü, Mn and Fe and related complexes, and cobalt(III) pentamine acetate and related complexes); (vii) a metal care agent in the range of about 0.1 wt% to 5 wt% (eg benzatriazoles, metal salts and complexes and/or silicates); and/or (viii) any active enzyme described herein in the range of from about 0.01 to 5.0 mg of active enzyme per gram of automatic dishwashing detergent composition and an enzyme stabilizing component (eg,

<img file="MX373205B_D0080.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY oligosaccharides, polysaccharides and inorganic divalent metal salts).

Various examples of detergent formulations comprising at least one poly-alpha-1,3-glucan ether compound (for example, a carboxyalkyl poly-alpha-1,3-glucan ether, such as poly-alpha-1,3 -carboxymethyl glucan [CMG]) are described below (1-19):

1) A detergent composition formulated as a granulate having a bulk density of at least 600 g/L comprising:

linear alkylbenzenesulfonate (calculated as acid), about 7-12% by weight; alcohol ethoxy sulfate (eg, C1218 alcohol, 1-2 ethylene oxide [EO]) or alkyl sulfate (eg, C16-18), about 1-4% by weight; alcohol ethoxylate (eg, C14-15 alcohol), about 5-9% by weight; sodium carbonate, about 14-20% by weight; soluble silicate (eg Na2O2SIO2), about 2-6% by weight; zeolite (for example, NaAlSiO₄), about 15-22% by weight; sodium sulfate, about 0-6% by weight; sodium citrate/citric acid, about 0-15% by weight; sodium perborate, about 11-18% by weight; TAED, about 2-6% by weight; ether

<img file="MX373205B_D0081.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

2) poly-alpha-1,3-glucan (eg, CMG) up to about 2% by weight; other polymers (eg, maleic/acrylic acid copolymer, PVP, PEG) about 0-3% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and minor ingredients (eg, suds reducers, perfumes, optical brightener, photobleach), about 0-5% by weight.

A detergent composition formulated as a granulate having a volume density of at least 600 g/L comprising: linear alkylbenzenesulfonate (calculated as acid), about 6-11% by weight; alcohol ethoxy sulfate (eg C1218 alcohol, 1-2 EO) or alkyl sulfate (eg C16-18), about 1-3% by weight; alcohol ethoxylate (eg, C14-15 alcohol), about 59% by weight; sodium carbonate, about 15-21% by weight; soluble silicate (eg NajO 2S1O2), about 1-4% by weight; zeolite (eg NaAlSiCU), about 24-34% by weight; sodium sulfate, about 4-10% by weight; sodium citrate/citric acid,

<img file="MX373205B_D0082.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY approximately 0-15% by weight; sodium perborate, about 11-18% by weight; TAED, about 2-6% by weight; poly-alpha1,3-glucan ether (eg, CMG) up to about 2% by weight; other polymers (eg, maleic/acrylic acid copolymer, PVP, PEG) about 1-6% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and minor ingredients (eg, suds reducers, perfumes, optical brightener, photobleach), about 0-5% by weight.

3) A detergent composition formulated as a granulate having a bulk density of at least 600 g/L comprising:

linear alkylbenzenesulfonate (calculated as acid), about 5-9% by weight; alcohol ethoxysulfate (eg, C12-18 alcohol, 7 EO), about 7-14% by weight; soap as fatty acid (eg C16-22 fatty acid), about 1-3% by weight; sodium carbonate, about 10-17% by weight; soluble silicate (eg Na20 2S1O2), about 3-9% by weight; zeolite (eg NaAlSiO4),

<img file="MX373205B_D0083.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY approximately 23-33% by weight; sodium sulfate, about 0-4% by weight; sodium perborate, about 8-16% by weight; TAED, about 2-8% by weight; phosphonate (eg EDTMPA), about 0-1% by weight; poly-alpha-1,3-glucan ether (eg, CMG) up to about 2% by weight; other polymers (eg, maleic/acrylic acid copolymer, PVP, PEG) about 0-3% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and minor ingredients (eg, foam reducers, perfumes, optical brightener), about 0-5% by weight.

4) A detergent composition formulated as a granulate having a bulk density of at least 600 g/L comprising:

linear alkylbenzenesulfonate (calculated as acid), about 8-12% by weight; alcohol ethoxylate (eg, C12-18 alcohol, 7 EO), about 10-25% by weight; sodium carbonate, about 14-22% by weight; soluble silicate (eg Na2O2SIO2), about 1-5% by weight; zeolite (eg NaAlSiO4),

<img file="MX373205B_D0084.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY approximately 25-35% by weight; sodium sulfate, about 0-10% by weight; sodium perborate, about 8-16% by weight; TAED, about 2-8% by weight; phosphonate (eg EDTMPA), about 0-1% by weight; poly-alpha-1,3-glucan ether (eg, CMG) up to about 2% by weight; other polymers (eg, maleic/acrylic acid copolymer, PVP, PEG) about 1-3% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and minor ingredients (eg foam reducers, perfumes), about 0-5% by weight.

5) An aqueous liquid detergent composition comprising: linear alkylbenzenesulfonate (calculated as acid), about 15-21% by weight; alcohol ethoxylate (eg, C12-18 alcohol, 7 EO); or C12-15 alcohol, 5 EO), about 12-18% by weight; soap as fatty acid (eg oleic acid), about 3-13% by weight; alkenylsuccinic acid (C12-14), about 0-13% by weight; aminoethanol, about 8-18% by weight; citric acid, about 2-8% by weight; phosphonate,

<img file="MX373205B_D0085.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY approximately 0-3% by weight; poly-alpha1,3-glucan ether (eg, CMG) up to about 2% by weight; other polymers (eg PVP, PEG), about 0-3% by weight; borate, about 0-2% by weight; ethanol, about 0-3% by weight; propylene glycol, about 8-14% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and minor ingredients (eg, dispersants, suds reducers, perfume, optical brightener), about 0-5% by weight.

6) An aqueous structured liquid detergent composition comprising: linear alkylbenzenesulfonate (calculated as acid), about 15-21% by weight; alcohol ethoxylate (eg, C12-18 alcohol, 7 EO); or C12-15 alcohol, 5 EO), about 3-9% by weight; soap as fatty acid (eg oleic acid), about 3-10% by weight; zeolite (for example, NaAlSiO₄), about 14-22% by weight; potassium citrate, about 9-18% by weight; borate, about 0-2% by weight; poly-alpha1,3-glucan ether (eg, CMG) to

<img file="MX373205B_D0086.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

7) about 2% by weight; other polymers (eg PVP, PEG), about 0-3% by weight; ethanol, about 0-3% by weight; fixative polymers (eg, lauryl methacrylate/acrylic acid copolymer, 25:1 molar ratio, MW 3800), about 0-3% by weight; glycerol, about 0-5% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and minor ingredients (eg, dispersants, suds reducers, perfume, optical brightener), about 0-5% by weight.

A detergent composition formulated as a granulate having a bulk density of at least 600 g/L comprising: fatty alcohol sulfate, about 5-10% by weight, ethoxylated fatty acid monoethanolamide, about 3-9% by weight; soap as fatty acid, about 0-3% by weight; sodium carbonate, about 5-10% by weight; soluble silicate (eg Na2® 2SIO2), about 1-4% by weight; zeolite (eg NaAlSiO4), about 20-40% by weight; sodium sulfate, about 2-8% by weight; sodium Perborate,

<img file="MX373205B_D0087.tif" />

' IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY approximately 12-18% by weight; TAED, about 2-7% by weight; poly-alpha1,3-glucan ether (eg, CMG) up to about 2% by weight; other polymers (eg, maleic/acrylic acid copolymer, PEG) about 1-5% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and minor ingredients (eg, optical brighteners, foam reducers, perfumes), about 0-5% by weight.

8) A detergent composition formulated as a granulate comprising: linear alkylbenzenesulfonate (calculated as acid), about 8-14% by weight; ethoxylated fatty acid monoethanolamide, about 5-11% by weight; soap as fatty acid, about 0-3% by weight; sodium carbonate, about 4-10% by weight; soluble silicate (eg Na20 2S1O2), about 1-4% by weight; zeolite (eg NaAlSiOl), about 30-50% by weight; sodium sulfate, about 3-11% by weight; sodium citrate, about 5-12% by weight; poly-alpha-1,3-glucan ether (eg, CMG) up to about 2% by weight; others

<img file="MX373205B_D0088.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

9) polymers (eg, PVP, maleic/acrylic acid copolymer, PEG) about 1-5% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and minor ingredients (eg foam reducers, perfumes), about 0-5% by weight.

A detergent composition formulated as a granulate comprising: linear alkylbenzenesulfonate (calculated as acid), about 6-12% by weight; nonionic surfactant, about 1-4% by weight; soap as fatty acid, about 2-6% by weight; sodium carbonate, about 14-22% by weight; zeolite (eg NaAlSiO4), about 18-32% by weight; sodium sulfate, about 5-20% by weight; sodium citrate, about 3-8% by weight; sodium perborate, about 4-9% by weight; bleach activator (eg NOBS or TAED), about 1-5% by weight; poly-alpha-1,3-glucan ether (eg, CMG) up to about 2% by weight; other polymers (eg polycarboxylate or PEG), about 1-5% by weight; optionally one or more enzymes (calculated as pure enzyme protein),

<img file="MX373205B_D0089.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY approximately 0.0001-0.1% by weight; and minor ingredients (eg, optical brightener, perfume), about 0-5% by weight.

10) An aqueous liquid detergent composition comprising: linear alkylbenzenesulfonate (calculated as acid), about 15-23% by weight; alcohol ethoxysulfate (eg, C12-15 alcohol, 2-3 EO), about 8-15% by weight; alcohol ethoxylate (eg, C12-15 alcohol, 7 EO); or C12-15 alcohol, 5 EO), about 3-9% by weight; soap as fatty acid (eg lauric acid), about 0-3% by weight; aminoethanol, about 1-5% by weight; sodium citrate, about 5-10% by weight; hydrotrope (eg sodium toluenesulfonate), about 2-6% by weight; borate, about 0-2% by weight; poly-alpha-1,3-glucan ether (eg, CMG) up to about 1% by weight; ethanol, about 1-3% by weight; propylene glycol, about 2-5% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and minor ingredients (for example, dispersants, perfume, optical brighteners),

<img file="MX373205B_D0090.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY approximately 0-5% by weight.

11) An aqueous liquid detergent composition comprising: linear alkylbenzenesulfonate (calculated as acid), about 20-32% by weight; alcohol ethoxylate (eg, C12-15 alcohol, 7 EO); or C12-15 alcohol, 5 EO), about 6-12% by weight; aminoethanol, about 2-6% by weight; citric acid, about 8-14% by weight; borate, about 1-3% by weight; poly-alpha1,3-glucan ether (eg, CMG) up to about 2% by weight; ethanol, about 1-3% by weight; propylene glycol, about 2-5% by weight; other polymers (eg, maleic/acrylic acid copolymer, fixing polymer such as lauryl methacrylate/acrylic acid copolymer), about 0-3% by weight; glycerol, about 3-8% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and minor ingredients (eg hydrotropes, dispersants, perfume, optical brighteners), about 0-5% by weight.

<img file="MX373205B_D0091.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

12) A detergent composition formulated as a granulate having a bulk density of at least 600 g/L comprising: anionic surfactant (for example, linear alkylbenzenesulfonate, alkylsulfate, alpha-olefinsulfonate, alpha-sulfo fatty acid methyl esters, alkanesulfonates, soap), about 25-40% by weight; nonionic surfactant (eg alcohol ethoxylate), about 1-10% by weight; sodium carbonate, about 8-25% by weight; soluble silicate (eg Na2O2SIO2), about 5-155% by weight; sodium sulfate, about 0-5% by weight; zeolite (eg NaAlSiOj), about 15-28% by weight; sodium perborate, about 0-20% by weight; bleach activator (eg, TAED or NOBS), about 0-5% by weight; poly-alpha-1,3-glucan ether (eg, CMG) up to about 2% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and minor ingredients (eg perfume, optical brighteners), about 0-3% by weight.

13) Detergent compositions as described in

<img file="MX373205B_D0092.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY (1)-(12) above, but, in which all or part of the linear alkylbenzenesulfonate is replaced by C12-C18 alkylsulfate.

14) A detergent composition formulated as a granulate having a volume density of at least 600 g/L comprising: C12-C18 sodium alkyl sulfate, about 9-15% by weight; alcohol ethoxylate, about 3-6% by weight; polyhydroxyalkyl fatty acid amide, about 1-5% by weight; zeolite (eg, NaAlSiOd, about 10-20 wt%; layered disilicate (eg, SK56 ex Hoechst), about 10-20 wt%; sodium carbonate, about 3-12% by weight; soluble silicate (eg Na2O2SIO2), about 0-6% by weight; sodium citrate, about 4-8% by weight; sodium percarbonate, about 13-22% by weight; TAED, about 3-8% by weight; poly-alpha1,3-glucan ether (eg, CMG) up to about 2% by weight; other polymers (eg polycarboxylates and PVP), about 0-5% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and

<img file="MX373205B_D0093.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY minor ingredients (for example, optical brightener, photobleach, perfume, foam reducers), approximately 0-5% by weight.

15) A detergent composition formulated as a granulate having a volume density of at least 600 g/L comprising: C12-C18 sodium alkyl sulfate, about 4-8% by weight; alcohol ethoxylate, about 11-15% by weight; soap, about 1-4% by weight; zeolite MAP or zeolite A, about 35-45% by weight; sodium carbonate, about 2-8% by weight; soluble silicate (eg Na20 2S1O2), about 0-4% by weight; sodium percarbonate, about 13-22% by weight; TAED, about 1-8% by weight; poly-alpha1,3-glucan ether (eg, CMG) up to about 3% by weight; other polymers (eg polycarboxylates and PVP), about 0-3% by weight; optionally one or more enzymes (calculated as pure enzyme protein), about 0.0001-0.1% by weight; and minor ingredients (eg, optical brightener, phosphonate, perfume), about 0-3% by weight.

16) Detergent formulations as described in

<img file="MX373205B_D0094.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY (1)-(15) above, but containing a stabilized or encapsulated peracid, either as an additional component or as a substitute for one or more of a specified bleaching system.

17) Detergent compositions as described in (1), (3), (7), (9) and (12) above, but in which the perborate is replaced by percarbonate.

18) Detergent compositions as described in (1), (3), (7), (9), (12), (14) and (15) above, but additionally containing a manganese catalyst. A manganese catalyst, for example, is one of the compounds described by Hage et al. (1994, Nature 369:637-639), incorporated herein by reference.

19) Detergent compositions formulated as a non-aqueous detergent liquid comprising a liquid nonionic surfactant (eg a linear alkoxylated primary alcohol), a builder system (eg phosphate), polyalpha-1,3-glucan ether (eg example, CMG), optionally, one or more enzymes and alkali. The detergent may further comprise an anionic surfactant and/or bleach system.

<img file="MX373205B_D0095.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

It is believed that several commercially available detergent formulations can be adapted to include a poly-alpha-1,3-glucan ether compound. Examples include PUREX® ULTRAPACKS (Henkel), FINISH® QUANTUM (Reckitt Benckiser), CLOROX™ 2 PACKS (Clorox), OXICLEAN MAX FORCE POWER PAKS (Church &amp; Dwight), TIDE® STAIN RELEASE, CASCADE® ACTIONPACS, and TIDE® PODS™ (Procter &amp; Gamble).

The compositions described herein may be in the form of an oral care composition. Examples of oral care compositions include dentifrices, toothpaste, mouthwash, mouthwash solution, chewing gum, edible strips that provide some form of oral care (eg, treatment or prevention of caries [dental caries], gingivitis , tartar, tartar and/or periodontal disease). An oral care composition may further be for the treatment of an oral surface, encompassing any soft or hard surface within the oral cavity including surfaces of the tongue, hard and soft palates, buccal mucosa, gums and tooth surfaces. . A tooth surface in the present description is a natural tooth surface or a hard artificial tooth surface including a crown, cap, filling, bridge, denture or dental implant, for example.

One or more poly-alpha-1,3-glucan and/or ether compounds

<img file="MX373205B_D0096.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY of poly-alpha-1,3-glucan comprised in an oral care composition are typically provided in this composition as a thickening agent and/or a dispersant, which may be useful for imparting to the composition a desired consistency and/or mouthfeel. An oral care composition herein may comprise about 0.01-15.0 wt% (eg -0.1-10 wt% or -0.1-5.0 wt%, -0.1-2.0 wt%) of one or plus poly-alpha-1,3-glucan and/or poly-alpha-1,3-glucan ether compounds described herein (for example, a carboxyalkyl poly-alpha-1,3-glucan ether such as poly -carboxymethyl alpha-1,3-glucan [CMG]), for example. One or more other thickening agents or dispersing agents may also be provided in an oral care composition of the present disclosure, such as a carboxyvinyl polymer, carrageenan (eg, L-carrageenan), natural gum (eg, example, karaya, xanthan, gum arabic, tragacanth), colloidal magnesium aluminum silicate or colloidal silica, for example.

An oral care composition in the present description can be a toothpaste or other dentifrice, for example. These compositions, in addition to any other oral care compositions of the present disclosure, may further comprise, without limitation, one or more agents.

<img file="MX373205B_D0097.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY anticaries, antimicrobial or antibacterial agents, anticalculus or tartar control agent, surfactant, abrasive, pH-modifying agent, foam buffer, humectant, flavoring, sweetener, pigment/colorant, bleaching agent, and/or or other suitable components. Some examples of oral care compositions to which one or more poly-alpha-1,3-glucan ether compounds may be added are described in US Patent Application Publication Nos. 2006/0134025, 2002/0022006 and 2008/0057007, incorporated herein by reference.

An anticaries agent in the present disclosure may be an orally acceptable source of fluoride ions. Suitable sources of fluoride ions include fluoride, monofluorophosphate and fluorosilicate salts, as well as amine fluorides, including olaflur (Ν' octadecyltrimethylenediamine-N,N,N'-tris(2-ethanol)dihydrofluoride), for example. An anticaries agent can be present, for example, in an amount that provides a total of about 100-20,000 ppm, about 200-5000 ppm, or about 500-2500 ppm fluoride ions to the composition. Oral care compositions, in which sodium fluoride is the exclusive source of fluoride ions, may contain an amount of about 0.01-5.0% by weight, about 0.05-1.0%

<img file="MX373205B_D0098.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY by weight or approximately 0.1-0.5% by weight of sodium fluoride, for example.

An antimicrobial or antibacterial agent suitable for use in an oral care composition herein includes, for example, phenolic compounds (eg, 4-allylcatechol; p-hydroxybenzoic acid ethers such as benzylparaben, butylparaben, ethylparaben, methylparaben and propylparaben, 2-benzylphenol, butylated hydroxyanisole, butylated hydroxytoluene, capsaicin, carvacrol, creosol, eugenol, guaiacol, halogenated bisphenolics such as hexachlorophene and bromochlorophene; 4-hexylresorcinol; 8-hydroxyquinoline and salts thereof; salicylic acid esters such as menthyl salicylate, methyl salicylate, and phenyl salicylate; phenol; pyrocatechol; salicylanilide; thymol; halogenated diphenyl ether compounds such as triclosan and triclosan monophosphate), copper (II) compounds (for example, copper (II) chloride, fluoride, sulfate, and hydroxide), zinc ion sources (for example, acetate, citrate, gluconate , glycinate, zinc oxide and sulfate), italic acid and salts thereof (for example, monopotassium magnesium phthalate), hexetidine, octenidine, sanguinarine, benzalkonium chloride, domifen bromide, alkylpyridinium chlorides (for example, cetylpyridinium chloride, tetradecylpyridinium chloride, N-tetradecyl-4-ethylpyridinium chloride), iodine, sulfonamides,

<img file="MX373205B_D0099.tif" />

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY bisbiguanides (eg, alexidine, chlorhexidine, chlorhexidine digluconate), piperidine derivatives (eg, delmopinol, octapinol), magnolia extract, grape seed extract, rosemary extract, menthol, geraniol, citral, eucalyptol, antibiotics (eg, augmentin, amoxicillin, tetracycline, doxycycline, minocycline, metronidazole, neomycin, kanamycin, clindamycin) and/or any antibacterial agent described in US patent no. 5776435, incorporated herein by reference. One or more antimicrobial agents may optionally be present in an amount of about 0.01-10% by weight (eg, 0.1-3% by weight), for example, in the disclosed oral care composition.

A suitable tartar control or anticalculus agent for use in an oral care composition herein includes, for example, phosphates and polyphosphates (eg, pyrophosphates), polyaminopropanesulfonic acid (AMPS), zinc citrate trihydrate, polypeptides (for example, polyaspartic and polyglutamic acids), polyolefin sulfonates, polyolefin phosphates, diphosphonates (for example, azacycloalkane-2,2-diphosphonates such as azacycloheptane-2,2-diphosphonic acid), N-methyl azacyclopentane-2,3-diphosphonic acid, ethane-1-hydroxy-1,1-diphosphonic acid (EHDP), ethane-1-amino-1,1-diphosphonate

<img file="MX373205B_D0100.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY and/or phosphonoalkane carboxylic acids and their salts (for example, their alkali metal and ammonium salts). Useful inorganic phosphate and polyphosphate salts include, for example, monobasic, dibasic, and tribasic sodium phosphates, sodium tripolyphosphate, tetrapolyphosphate, mono-, di-, tri-, and tetra-sodium pyrophosphates, disodium dihydrogen pyrrophosphate, sodium trimetaphosphate, sodium hexametaphosphate or any of these in which sodium is replaced by potassium or ammonium. Other anticalculus agents useful in certain embodiments include anionic polycarboxylate polymers (eg, polymers or copolymers of acrylic, methacrylic acid, and maleic anhydride such as polyvinyl methyl ether/maleic anhydride copolymers). Other useful anticalculus agents include sequestering agents, such as hydroxycarboxylic acids (eg, citric, fumaric, malic, glutaric, and oxalic acids and salts thereof) and aminopolycarboxylic acids (eg, EDTA). One or more anticalculus agents or tartar control agents may optionally be present in an amount of about 0.01-50% by weight (for example, about 0.05-25% by weight or about 0.1-15% by weight), for example, in the described oral care composition.

A suitable surfactant for use in an oral care composition in the present description may be

<img file="MX373205B_D0101.tif" />

IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY anionic, non-ionic or amphoteric, for example. Suitable anionic surfactants include, but are not limited to, water-soluble salts of Ce-2o alkyl sulfates, sulfonated monoglycerides of Ce-2o fatty acids, sarcosinates, and taurates. Examples of anionic surfactants include sodium lauryl sulfate, sodium coco monoglyceride sulfonate, sodium lauryl sarcosinate, sodium lauryl isoethionate, sodium laureth carboxylate, and sodium dodecyl benzenesulfonate. Suitable nonionic surfactants include, but are not limited to, poloxamers, polyoxyethylene sorbitan esters, fatty alcohol ethoxylates, alkylphenol ethoxylates, tertiary amine oxides, tertiary phosphine oxides, and dialkyl sulfoxides. Suitable amphoteric surfactants include, without limitation, secondary and tertiary aliphatic amine derivatives of Ce20 having an anionic group such as a carboxylate, sulfate, sulfonate, phosphate or phosphonate. An example of a suitable amphoteric surfactant is cocoamidopropyl betaine. One or more surfactants are optionally present in a total amount of about 0.01-10% by weight (for example, about 0.05-5.0% by weight or about 0.1-2.0% by weight), for example, in the composition for the oral care described.

An abrasive suitable for use in an oral care composition herein may include,

<img file="MX373205B_D0102.tif" />

IMPI

100

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY For example, silica (for example, silica gel, hydrated silica, precipitated silica), alumina, insoluble phosphates, calcium carbonate, and resinous abrasives (for example, a urea-formaldehyde condensation product). Examples of insoluble phosphates useful as abrasives in the present disclosure are orthophosphates, polymetaphosphates, and pyrophosphates, and include dicalcium orthophosphate dihydrate, calcium pyrophosphate, beta-calcium pyrophosphate, tricalcium phosphate, calcium polymetaphosphate, and insoluble sodium polymetaphosphate. One or more abrasives are optionally present in a total amount of about 5-70% by weight (eg, about 10-56% by weight or about 15-30% by weight), for example, in the composition for the oral care described. The average particle size of an abrasive in certain embodiments is about 0.1-30 microns (eg, about 1-20 microns or about 515 microns).

An oral care composition in certain embodiments may comprise at least one pH modifying agent. Such agents can be selected to acidify, basicize, or buffer the pH of a composition to a pH range of about 2-10 (eg, a pH ranging from about 2-8, 3-9, 4-8, 5). -7, 6-10 or 79). Some Examples of Useful pH Modifying Agents

<img file="MX373205B_D0103.tif" />

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101

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY in this description include, without limitation, carboxylic, phosphoric and sulfonic acids; acid salts (eg monosodium citrate, disodium citrate, monosodium malate); alkali metal hydroxides (eg sodium hydroxide, carbonates such as sodium carbonate, bicarbonates, sesquicarbonates); borates; silicates; phosphates (eg monosodium phosphate, trisodium phosphate, pyrophosphate salts); and imidazole.

A suitable foam modulator for use in an oral care composition of the present disclosure may be a polyethylene glycol (PEG), for example. High molecular weight PEGs are suitable, and include those having a molecular weight of about 200,000-7,000,000 (eg, about 500,000-5,000,000 or about 1,000,000-2,500,000), for example. One or more PEGs are optionally present in a total amount of about 0.1-10% by weight (for example, about 0.2-5.0% by weight or about 0.25-2.0% by weight), for example, in the composition for the oral care described.

An oral care composition in certain embodiments may comprise at least one humectant. A humectant in certain embodiments can be a polyhydric alcohol such as glycerin, sorbitol, xylitol, or a low molecular weight PEG. Most suitable humectants can also function as a sweetener in the present

<img file="MX373205B_D0104.tif" />

102 ' IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY description. One or more humectants are optionally present in a total amount of about 1070 wt% (eg, about 1.0-50 wt%, about 2-25 wt%, or about 5-15 wt%), eg , in the described oral care composition.

A natural or artificial sweetener may optionally be comprised in an oral care composition of the present disclosure. Examples of suitable sweeteners include dextrose, sucrose, maltose, dextrin, invert sugar, mannose, xylose, ribose, fructose, levulose, galactose, corn syrup (eg, high fructose corn syrup or corn syrup solids). ), partially hydrolyzed starch, hydrogenated starch hydrolysate, sorbitol, mannitol, xylitol, maltitol, isomalt, aspartame, neotame, saccharin and salts thereof, dipeptide-based intense sweeteners and cyclamates. One or more sweeteners are optionally present in a total amount of about 0.005-5.0% by weight, for example, in the disclosed oral care composition.

A natural or artificial flavor may optionally be comprised in an oral care composition of the present disclosure. Examples of suitable flavors include vanillin; sage; marjoram; parsley oil; peppermint oil; cinnamon oil; oil

<img file="MX373205B_D0105.tif" />

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103

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY of wintergreen (methylsalicylate); peppermint oil; clove oil; Bay oil; anise oil; eucalyptus oil; citrus oils; fruity oils; essences such as those derived from lemon, orange, lime, grapefruit, apricot, banana, grape, apple, strawberry, cherry or pineapple; flavorings derived from grains and nuts such as coffee, cocoa, soft drinks, peanut or almond; and adsorbed and encapsulated flavorings. In addition, the flavors of the present disclosure may comprise ingredients that provide a fragrance effect and/or other sensory effect in the mouth, including cooling or warming effects. These ingredients include, but are not limited to, menthol, menthyl acetate, menthyl lactate, camphor, eucalyptus oil, eucalyptol, anethole, eugenol, cassia, oxanone, Irisone®, propenyl guaiethol, thymol, linalool, benzaldehyde, cinnamaldehyde, N- ethyl-p-menthan-3-carboxamine, N,2,3-trimethyl-2-isopropylbutanamide, 3-(1-menthoxy)-propane1,2-diol, cinnamaldehyde glycerol acetal (CGA), and menthone glycerol acetal (MGA). One or more flavors are optionally present in a total amount of about 0.01-5.0% by weight (eg, about 0.1-2.5% by weight), for example, in the disclosed oral care composition.

An oral care composition in certain embodiments may comprise at least one bicarbonate salt.

<img file="MX373205B_D0106.tif" />

IMPI

104

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

Any orally acceptable bicarbonate can be used including alkali metal bicarbonates such as sodium or potassium bicarbonate and ammonium bicarbonate, for example. One or more bicarbonate salts are optionally present in a total amount of about 0.1-50% by weight (eg, about 1-20% by weight), for example, in the disclosed oral care composition.

An oral care composition in certain embodiments may comprise at least one bleaching and/or coloring agent. A suitable bleaching agent is a peroxide compound, such as any of those described in US patent no. 8540971, incorporated herein by reference. Suitable colorants in the present disclosure include pigments, dyes, lacquers, and agents that impart a particular shine or reflectivity, such as pearlescent agents, for example. Specific examples of colorants useful in the present description include talc; mica; magnesium carbonate; calcium carbonate; magnesium silicate; aluminum magnesium silicate; silica; titanium dioxide; zinc oxide; red, yellow, brown and black iron oxides; ferric ammonium ferrocyanide; manganese violet; overseas; titanated mica; and bismuth oxychloride. One or more colorants are optionally present in a total amount of about 0.001-20% by weight (for example,

<img file="MX373205B_D0107.tif" />

105

7* IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY about 0.01-10% by weight or about 0.1-5.0% by weight), for example, in the described oral care composition.

Additional components that may optionally be included in an oral composition in the present description include one or more enzymes (above), vitamins and anti-adhesion agents, for example. Examples of vitamins useful in the present disclosure include vitamin C, vitamin E, vitamin B5, and folic acid. Examples of suitable anti-adhesion agents include solbrol, ficin, and quorum sensing inhibitors.

The disclosed invention further relates to a method for increasing the viscosity of an aqueous composition. This method comprises contacting one or more poly-alpha-1,3-glucan ether compounds described herein with the aqueous composition. This step produces an increase in the viscosity of the aqueous composition. The poly-alpha-1,3-glucan ether compound(s) used in this method may be represented by the structure:

<img file="MX373205B_D0108.tif" />

<img file="MX373205B_D0109.tif" />

IMPI

106

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

With respect to the formula of this structure, n can be at least 6 and each R can independently be an H or an organic group. Also, the polyalpha-1,3-glucan ether compound has a degree of substitution of from about 0.05 to about 3.0. Any hydrocolloid and aqueous solution described in the present description can be produced using this method.

An aqueous composition of the present disclosure can be water (eg, deionized water), an aqueous solution, or a hydrocolloid, for example. The viscosity of an aqueous composition before the contacting step, measured at about 20-25°C, can be about 010,000 cPs (or any integer between 0 and 10,000 cPs), for example. Since the aqueous composition may be a hydrocolloid or the like in certain embodiments, it will be apparent that the method can be used to increase the viscosity of already viscous aqueous compositions.

Contacting a poly-alpha-1,3-glucan ether compound described herein with an aqueous composition increases the viscosity of the aqueous composition in certain embodiments. This increase in viscosity can be an increase of at least about 1%, 10%, 100%, 1000%, 100,000% or 1,000,000% (or any whole number between 1% and 1,000,000%), for example, compared to the viscosity of the aqueous composition before

<img file="MX373205B_D0110.tif" />

IMPI

107

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY of the contact stage. It will be apparent that considerable percentage increases in viscosity can be obtained by the described method when the aqueous composition is not viscous or has a very low viscosity prior to the contacting step.

Contacting a poly-alpha-1,3-glucan ether compound described herein with an aqueous composition increases the shear thinning or swelling behavior of the aqueous composition in certain embodiments. Therefore, a poly-alpha-1,3-glucan ether compound rheologically modifies the aqueous composition in these embodiments. The increase in shear thinning or dilatant behavior can be an increase of at least about 1%, 10%, 100%, 1000%, 100,000%, or 1,000,000% (or any integer between 1% and 1,000,000%), for example , compared to the pseudoplastic behavior or dilatant behavior of the aqueous composition before the contact stage. It will be apparent that considerable percentage increases in rheological modification can be obtained with the described method when the aqueous composition has no rheological behavior or exhibits very little rheological behavior prior to the contacting step.

The contact step can be carried out by mixing or dissolving one or more polyalpha-1, 3-glucan ester compounds described in the present description in the

<img file="MX373205B_D0111.tif" />

IMPI

108

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY aqueous composition by any means known in the field. For example, mixing or dissolution can be done manually or with a machine (eg, industrial mixer, orbital shaker, stir plate, homogenizer, sonicator, ball mill). The mixing or dissolution may comprise a homogenization step in certain embodiments. Homogenization (plus any other mixing) can be done for about 5 to 60, 5 to 30, 10 to 60, 10 to 30, 5 to 15, or 10 to 15 seconds (or any integer between 5 and 60 seconds) or longer periods required to mix a poly-alpha-1,3-glucan ether compound with the aqueous composition. A homogenizer can be used, for example, at about 5,000 to 30,000 rpm, 10,000 to 30,000 rpm, 15,000 to 30,000 rpm, 15,000 to 25,000 rpm, or 20,000 rpm (or any integer between 5,000 and 30,000 rpm). The hydrocolloids and aqueous solutions described herein prepared with the use of a homogenization step may be referred to as hydrocolloids and homogenized aqueous solutions.

After a poly-alpha-1,3-glucan ether compound is mixed with or dissolved in an aqueous composition, the resulting aqueous composition may or may not be filtered. For example, an aqueous composition prepared with a homogenization step may or may not be filtered.

<img file="MX373205B_D0112.tif" />

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109

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

Certain embodiments of the above method can be used to prepare an aqueous composition described herein, such as a household product (eg, laundry detergent, fabric softener, dishwashing detergent), personal care product (eg, a water-containing dentifrice, such as toothpaste) or industrial product.

The described invention further relates to a method for treating a material. This method comprises contacting a material with an aqueous composition comprising at least one poly-alpha-1,3-glucan ether compound described herein. A poly-alpha-1,3-glucan ether compound used in this method is represented by the structure:

<img file="MX373205B_D0113.tif" />

With respect to the formula of this structure, n can be at least 6 and each R can independently be an H or an organic group. Furthermore, the polyalpha-1,3-glucan ether compound has a degree of substitution of from about 0.05 to about 3.0.

<img file="MX373205B_D0114.tif" />

IMPI

110

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

A material that is contacted with an aqueous composition in a contacting method of the present disclosure may comprise a fabric in certain embodiments. A fabric of the present disclosure may comprise natural fibers, synthetic fibers, semi-synthetic fibers, or any combination of these. A semi-synthetic fiber of the present disclosure is produced with the use of a naturally occurring material that has been chemically derived, an example of which is rayon. Non-limiting examples of fabric types herein include fabrics made from (i) cellulosic fibers such as cotton (for example, close-knit wool, canvas, chambray, chenille, chintz, corduroy, chintz, damask, denim, flannel, gingham, jacquard, woven, quilting, oxford, percale, poplin, pleated, satin, seersucker, sheers, terry, twill, velvet), rayon (for example, viscose, modal, lyocell), linen, and Tencel®; (ii) protein fibers, such as silk, wool, and related mammalian fibers; (iii) synthetic fibers such as polyester, acrylic, nylon, and the like; (iv) long vegetable fibers of jute, flax, ramie, coconut fiber, kapok, sisal, henequen, abaca, hemp and Bengal hemp; and (v) any combination of a fabric of (i)-(iv). Fabrics comprising a combination of fiber types (eg, natural and synthetic) include those having a cotton and polyester fiber, for example. The

<img file="MX373205B_D0115.tif" />

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111

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY Materials/articles that contain one or more fabrics in this description include, for example, clothing, curtains, draperies, upholstery, rugs, bedding, bath linens, tablecloths, sleeping bags , tents, car interiors, etc. Other materials comprising natural and/or synthetic fibers include, for example, nonwoven fabrics, fillers, paper, and foams.

An aqueous composition that contacts fabric can be, for example, a fabric care composition (eg, laundry detergent, fabric softener). Thus, a treatment method in certain embodiments may be considered a fabric care method or laundry method if a fabric care composition is used therein. A fabric care composition of the present disclosure may provide one or more of the following fabric care benefits (i.e., surface substantive effects): wrinkle removal, wrinkle reduction, wrinkle resistance, fabric wear reduction, fabric wear resistance, fabric pilling reduction, fabric color maintenance, color fading reduction fabric, fabric color restoration, fabric soil reduction, fabric stain release, shape retention

<img file="MX373205B_D0116.tif" />

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112

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY of the fabric, improvement of the softness of the fabric, anti-redeposition of dirt on the fabric, anti-graying of the washed clothes, improvement of the handling/feel imparted by the fabric and/or reduction of shrinkage of the cloth.

Examples of conditions (eg, time, temperature, wash/rinse volumes) for carrying out a fabric care method or laundry method of the present disclosure are described in US Pat. WO1997/003161 and in US patent nos. 4794661, 4580421 and 5945394, incorporated herein by reference. In other examples, a material comprising fabric may be contacted with an aqueous composition of the present disclosure: (i) for at least about 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100 , 110 or 120 minutes; (ii) at a temperature of at least about 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, or 95°C (for example , for washing or rinsing clothes: a cold temperature of about 15-30°C, a medium temperature of about 30-50°C, a hot temperature of about 50-95°C); (iii) at a pH of about 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 (eg, a pH range of about 2-12 or about 3-11); (iv) at a salt (eg, NaCl) concentration of at least about 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, or 4.0% by weight; or any combination of

<img file="MX373205B_D0117.tif" />

113

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY (i) - (iv) .

The contacting step in a fabric care method or laundry method may comprise any washing, soaking and/or rinsing step, for example. In still other embodiments, contacting a material or fabric may be by any means known in the art, such as dissolving, mixing, stirring, spraying, treating, immersing, rinsing, pouring on or in, blending, painting, coating, applying, attaching to and/or communicating an effective amount of a poly-alpha-1,3-glucan ether compound of the present disclosure with the fabric or material. In still other embodiments, contact can be used to treat a fabric to provide a substantive effect to a surface. As used herein, "fabric feel" or "handling" refers to a person's tactile sensory response to fabric that may be physical, physiological, psychological, social, or any combination of these. In one embodiment, the feel of the fabric to the touch can be measured using a PhabrOmeter® system for measuring relative tactile value (available from Nu Cybertek, Inc., Davis, CA) (American Association of Textile Chemists and Colorists (method AATCC 202-2012, Relative Hand Value of Textiles: Instrumental Method)).

In certain modalities of the treatment of a material

<img file="MX373205B_D0118.tif" />

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114

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY comprising fabric, one or more components of a poly-alpha-1,3-glucan ether compound of the aqueous composition is adsorbed on the fabric. This feature is believed to make poly-alpha-1,3-glucan ether compounds (eg, anionic glucan ether compounds such as carboxymethyl poly-alpha1,3-glucan) useful as antiredeposition agents and/or or anti-graying in fabric care compositions described herein (in addition to its viscosity modifying effect). An anti-redeposition agent or anti-graying agent of the present disclosure helps prevent soil from redepositing on clothes in the wash water after the soil has been removed. Furthermore, adsorption of one or more poly-alpha-1,3-glucan ether compounds of the present disclosure onto a fabric is contemplated to improve the mechanical properties of the fabric.

The following examples demonstrate that poly-alpha-1,3-glucan ether compounds such as carboxymethyl poly-alpha-1,3-glucan adsorb to natural (cotton, chintz) and synthetic (polyester) fabrics, as well as a mixture of these (polyester/cretonne). This result is surprising since carboxymethylcellulose (CMC) is not absorbed or is absorbed to a very small amount in polyester and polyester-cotton blends (see European Patent Application Publication No. EP0035478,

<img file="MX373205B_D0119.tif" />

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115

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY for example). Thus, in certain embodiments of a method of treatment herein, an anionic poly-alpha-1,3-glucan ether compound (eg, carboxyalkyl poly-alpha-1,3-glucan such as poly -carboxymethyl alpha-1,3-glucan) is adsorbed on material comprising natural fiber (eg cotton) and/or synthetic fiber (eg polyester). Such adsorption of an anionic poly alpha-1,3-glucan ether compound may be at least about 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 100%, 120%, 140%, 160%, 180% or 200% greater than the adsorption of the same glucan ether on cotton fabric (eg cretonne), for example. In addition, adsorption can optionally occur under conditions of about 1-3 or 1-4 wt% salt (eg NaCl) and/or a pH of about 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, 9.0, or 9.5, for example.

The adsorption of a poly-alpha-1,3-glucan ether compound on a fabric of the present disclosure can be determined, for example, according to the methodology described in the examples below. Alternatively, adsorption can be measured using a colorimetric technique (eg, Dubois et al., 1956, Anal. Chem. 28:350-356; Zemljic et al., 2006, Lenzinger Berichte 85:6876; both incorporated herein by reference) or any other method known in the art.

<img file="MX373205B_D0120.tif" />

116 ' IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

Other materials that may be contacted in the above treatment method include surfaces that may be treated with a dish detergent (eg, detergent for an automatic dishwashing machine or manual dishwashing detergents). Examples of these materials include surfaces of plates, glasses, pots, pans, baking dishes, utensils, and cutlery made of ceramic, porcelain, metal, glass, plastic (eg, polyethylene, polypropylene, polystyrene, etc.), and wood. (collectively, referred to herein as tableware). Therefore, the treatment method in certain embodiments may be considered a dishwashing method or tableware washing method, for example. Examples of conditions (eg, time, temperature, wash volume) for carrying out a dishware or tableware washing method of the present disclosure are described in US patent no. 8575083, incorporated herein by reference. In other examples, an article of tableware may be contacted with an aqueous composition of the present disclosure under a set of suitable conditions, such as any of those described above with respect to contacting a material comprising fabric.

Other materials that can be contacted in the

<img file="MX373205B_D0121.tif" />

117

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY method of treatment above include oral surfaces, such as any soft or hard surface within the oral cavity including surfaces of the tongue, hard and soft palate, buccal mucosa, gums, and dental surfaces (e.g., teeth). natural or a hard surface of artificial teeth such as a crown, cap, filling, bridge, denture or dental implant). Thus, a treatment method in certain modalities may be considered an oral care method or a dental care method, for example. Conditions (eg, time, temperature) for contacting a buccal surface with an aqueous composition of the present disclosure should be suitable for the intended purpose of making such contact. Other surfaces that may be contacted in a method of treatment further include a surface of the integumentary system, such as skin, hair, or nails.

Therefore, certain embodiments of the disclosed invention relate to the material (eg, fabric) comprising a poly-alpha-1,3-glucan ether compound of the present disclosure. This material can be produced according to a material treatment method as described, for example. A material may comprise a glucan ether compound in certain embodiments, if the compound is adsorbed or otherwise in contact with the surface.

<img file="MX373205B_D0122.tif" />

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118

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY of the material.

Certain embodiments of a method of treating a material of the present disclosure further comprise a drying step in which a material is dried after contacting the aqueous composition. A drying step can be carried out directly after the contact step or after one or more additional steps that could follow the contact step (for example, the drying of a fabric after rinsing, in water, for example, after a wash in an aqueous composition of the present disclosure). Drying can be accomplished by any of a number of means known in the art, such as air drying (eg, ~20-25°C), or at a temperature of at least about 30, 40, 50, 60, 70, 80, 90, 100, 120, 140, 160, 170, 175, 180 or 200°C, for example. A dried material of the present description typically comprises less than 3, 2, 1, 0.5 or 0.1% by weight of water. A cloth is a preferred material for carrying out an optional drying step.

An aqueous composition used in a treatment method of the present disclosure may be any aqueous composition described herein, such as in the embodiments above or in the examples below. Thus, the poly-alpha-1,3 glucan ether component(s) of an aqueous composition may be any of those described herein. Examples of aqueous compositions include detergents (eg, laundry detergent or dish detergent) and water-containing dentifrices, such as toothpaste.

The poly-alpha-1,3-glucan ether compounds useful in preparing the hydrocolloids and aqueous solutions of the present invention can be prepared as described in US patent application publication no. 2014/0179913 (incorporated herein by reference), and as described herein, for example.

The poly-alpha-1,3-glucan ether compounds described in the present description can be produced by a method comprising: putting the poly-alpha-1,3-glucan in a reaction under alkaline conditions in contact with at least one etherifying agent comprising an organic group, wherein the organic group is etherified to poly-alpha-1,3-glucan to produce a poly-alpha-1,3-glucan ether compound represented by the structure:

where (i) n is at least 6,

<img file="MX373205B_D0123.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY (ii) each R is independently an H or an organic group and (iii) the compound has a degree of substitution of from about 0.05 to about 3.0.

A poly-alpha-1,3-glucan ether produced by this method may optionally be isolated. This method can be considered to comprise an etherification reaction.

The following steps can be considered to prepare the above etherification reaction. The poly-alpha-1,3-glucan can be contacted with a solvent and one or more alkali hydroxides to provide a solution or mixture. Therefore, the alkaline reaction conditions may comprise an alkali hydroxide solution. The pH of alkaline conditions can be at least about 11.0, 11.2, 11.4, 11.6, 11.8, 12.0, 12.2, 12.4, 12.6, 12.8, or 13.0.

Various alkali hydroxides can be used, such as sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium hydroxide and/or tetraethylammonium hydroxide. The concentration of the alkali hydroxide in a preparation with poly-alpha-1,3-glucan and a solvent may be about 1-70% by weight, 5-50% by weight, 10-50% by weight, 10-40% by weight. by weight or 10-30% by weight (or any integer between 1 and 70% by weight). Alternatively, the concentration of the alkali hydroxide, such as sodium hydroxide, can be by

<img file="MX373205B_D0124.tif" />

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121

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY at least approximately 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27, 28, 29 or 30% by weight. An alkali hydroxide used to prepare the alkaline conditions may be in a wholly aqueous solution or an aqueous solution comprising one or more water-soluble organic solvents, such as ethanol or isopropanol. Alternatively, an alkali hydroxide can be added as a solid to produce alkaline conditions.

Various organic solvents that may optionally be included in preparing the reaction include alcohols, acetone, dioxane, isopropanol, and toluene, for example; neither of these solvents dissolve poly-alpha-1,3-glucan. In certain embodiments, toluene or isopropanol can be used. An organic solvent can be added before or after the addition of the alkali hydroxide. The concentration of an organic solvent (for example, isopropanol or toluene) in a preparation comprising poly-alpha-1,3-glucan and an alkali hydroxide can be at least about 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85 or 90% by weight (or any integer between 10 and 90% by weight).

Alternatively, solvents that can dissolve poly-alpha-1,3-glucan can be used in preparing the reaction. These solvents include, but are not limited to, lithium chloride(LiCl)/N,N-dimethyl-acetamide (DMAc), SOz/diethylamine

<img file="MX373205B_D0125.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY (DEA)/dimethyl sulfoxide (DMSO), LiCl/1,3-dimethyl-2imidazolidinone (DMI), Ν,Ν-dimethylformamide (DMF)/N2O₄, DMSO/tetrabutylammonium fluoride trihydrate (TBAF), N-methylmorpholine-N-oxide (NMMO), aqueous solutions of Ni(tren)(OH)2 [tren^tris(2-aminoethyl)amine] and LIC1O4-3H2O fusions, aqueous solutions of NaOH/urea, aqueous sodium hydroxide, aqueous potassium hydroxide, formic acid and ionic liquids.

Poly-alpha-1,3-glucan can be contacted with a solvent and one or more alkali hydroxides by mixing. Such mixing can be carried out during or after adding these components together. The mixing can be carried out manually, it can be mixed with the use of a vertical mixer, with the use of a magnetic stir bar or with stirring, for example. In certain embodiments, the polyalpha-1,3-glucan may first be mixed in water or an aqueous solution before mixing with a solvent and/or alkali hydroxide.

After bringing the poly-alpha-1,3-glucan, solvent and one or more alkali hydroxides into contact with each other, the resulting composition may optionally be kept at room temperature for up to 14 days. The term room temperature, as used in the present description, refers to a temperature between about 15-30°C or 20-25°C (or any integer between

<img file="MX373205B_D0126.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY and 30°C). Alternatively, the composition may be heated with or without reflux at a temperature of from about 30°C to about 150°C (or any integer between 30 and 150°C) for up to about 48 hours. In certain embodiments, the composition can be heated to about 55°C for about 30 minutes or 60 minutes. Therefore, a composition obtained by mixing a poly-alpha-1,3-glucan, solvent and one or more alkali hydroxides together can be heated to about 50, 51, 52, 53, 54, 55, 56, 57, 58 , 59 or 60°C for approximately 30-90 minutes.

After bringing the poly-alpha-1,3-glucan, solvent and one or more alkali hydroxides into contact with each other, the resulting composition can optionally be filtered (with or without applying a temperature treatment step). Such filtration can be carried out with the use of a funnel, centrifuge, pressure filter or any other method and/or equipment known in the art that allows liquids to be removed from solids. Although filtration removes much of the alkaline hydroxide, the filtered poly-alpha-1,3-glucan would still be alkaline (eg, mercerized poly-alpha-1,3-glucan), to provide alkaline conditions.

An etherifying agent comprising an organic group can be contacted with poly-alpha-1,3-glucan in a reaction under alkaline conditions in a method of

<img file="MX373205B_D0127.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY present description to produce poly-alpha-1,3-glucan ether compounds. For example, an etherifying agent can be added in a composition that is prepared by contacting poly-alpha-1,3-glucan, solvent, and one or more alkali hydroxides with each other as described above. Alternatively, an etherifying agent may be included when alkaline conditions are prepared (for example, an etherifying agent may be mixed with poly-alpha-1,3-glucan and solvent before mixing with alkali hydroxide).

An etherifying agent of the present description refers to an agent that can be used to etherify one or more hydroxyl groups of the glucose units of poly-alpha1,3-glucan with an organic group as described above. Examples of such organic groups include alkyl groups, hydroxyalkyl groups, and carboxyalkyl groups. One or more etherifying agents may be used in the reaction.

Suitable etherifying agents for preparing an alkyl poly-alpha-1,3-glucan ether compound include, for example, dialkyl sulfates, dialkyl carbonates, alkyl halides (eg, alkyl chloride), iodoalkanes, alkyl triflates (alkyl trifluoromethanesulfonates) and alkyl fluorosulfonates. Therefore, the examples of agents of

<img file="MX373205B_D0128.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY etherification to produce poly-alpha-1,3-glucan methyl ethers include dimethyl sulfate, dimethyl carbonate, methyl chloride, iodomethane, methyl triflate, and methyl fluorosulfonate. Examples of etherifying agents to produce ethyl poly-alpha-1,3-glucan ethers include diethyl sulfate, diethyl carbonate, ethyl chloride, iodoethane, ethyl triflate, and ethyl fluorosulfonate. Examples of etherifying agents to produce poly-alpha-1,3-propyl glucan ethers include dipropyl sulfate, dipropyl carbonate, propyl chloride, iodopropane, propyl triflate, and propyl fluorosulfonate. Examples of etherifying agents to produce poly-butyl alpha-1,3-glucan ethers include dibutyl sulfate, dibutyl carbonate, butyl chloride, iodobutane, and butyl triflate.

Suitable etherifying agents for preparing a hydroxyalkyl poly-alpha-1,3-glucan ether compound include, for example, alkylene® oxides, such as ethylene oxide, propylene oxide (eg, 1, 2-propylene), butylene oxide (eg, 1,2-butylene oxide; 2,3-butylene oxide; 1,4-butylene oxide), or combinations of these. As examples, propylene oxide can be used as an etherifying agent to prepare poly-alpha-1,3-hydroxypropyl glucan and ethylene oxide can be used as an etherifying agent to prepare

<img file="MX373205B_D0129.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY poly-alpha-1,3-hydroxyethyl glucan. Alternatively, hydroxyalkyl halides (eg, hydroxyalkyl chloride) can be used as etherifying agents to prepare hydroxyalkyl poly-alpha-1,3-glucan. Examples of hydroxyalkyl halides include hydroxyethyl halide, hydroxypropyl halide (eg, 2-hydroxypropyl chloride, 3-hydroxypropyl chloride), and hydroxybutyl halide. Alternatively, alkylene chlorohydrins can be used as etherifying agents to prepare hydroxyalkyl poly-alpha-1,3-glucan. Alkylene chlorohydrins that can be used include, but are not limited to, ethylene chlorohydrin, propylene chlorohydrin, butylene chlorohydrin, or combinations of these.

Suitable etherifying agents for preparing a dihydroxyalkyl poly-alpha-1,3-glucan ether compound include dihydroxyalkyl halides (eg dihydroxyalkyl chloride), such as dihydroxyethyl halide, dihydroxypropyl halide (eg dihydroxyalkyl chloride) 2,3-dihydroxypropyl [eg, 3-chloro-1,2-propanediol]) or dihydroxybutyl halide, for example. 2,3-dihydroxypropyl chloride can be used to prepare dihydroxypropyl poly-alpha-1,3-glucan, for example.

Suitable etherifying agents for preparing a carboxyalkyl poly-alpha-1,3-glucan ether compound may include haloalkylates (eg, chloroalkylate).

<img file="MX373205B_D0130.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

Examples of haloalkylates include haloacetate (eg chloroacetate), 3-halopropionate (eg 3-chloropropionate) and 4-halobutyrate (eg 4-chlorobutyrate). For example, chloroacetate (monochloroacetate) (eg, sodium chloroacetate or chloroacetic acid) can be used as an etherifying agent to prepare carboxymethyl poly-alpha-1,3-glucan.

Therefore, in producing a polyalpha-1,3-glucan ether compound with two or more different organic groups, two or more different etherifying agents would be used. For example, both an alkylene oxide and an alkyl chloride could be used as etherifying agents to produce an alkyl hydroxyalkyl poly-alpha-1,3-glucan ether. Therefore, any of the etherifying agents described herein can be combined to produce poly-alpha-1,3-glucan ether compounds with two or more different organic groups. These two or more etherifying agents may be used in the reaction at the same time or may be used in the reaction sequentially. When used sequentially, any of the temperature treatment (eg heating) steps described below may optionally be used between each addition. Sequential introduction of etherifying agents could be selected to control the desired DoS of each organic group.

<img file="MX373205B_D0131.tif" />

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Generally, a particular etherifying agent would be used first if the organic group forming in the ether product is desired at a higher DoS compared to the DoS of another organic group to be added.

The amount of etherifying agent to be contacted with polyalpha-1,3-glucan in a reaction under alkaline conditions can be determined based on the degree of substitution required in the polyalpha-1,3-glucan ether compound. that is produced. The amount of ether substitution groups on each monomer unit in the poly-alpha-1,3-glucan ether compounds produced in the present disclosure can be determined with the use of nuclear magnetic resonance (NMR) spectroscopy. The molar substitution value (MS) for poly-alpha-1,3-glucan has no upper limit. Generally, an etherifying agent can be used in an amount of at least about 0.05 mole per mole of poly-alpha-1,3-glucan. There is no upper limit to the amount of etherifying agent that can be used.

The reactions to produce the poly-alpha-1,3-glucan ether compounds of the present invention may optionally be carried out in a pressure apparatus, such as a Parr reactor, an autoclave, a stirrer tube, or any other apparatus. pressure apparatus well known in the art. In certain embodiments, a stirrer tube is used to carry

<img file="MX373205B_D0132.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY carried out the reaction.

A reaction of the present invention may optionally be heated following the step of contacting the poly-alpha-1,3-glucan with an etherifying agent under alkaline conditions. The reaction temperatures and the time for applying such temperatures can be varied within wide limits. For example, a reaction may optionally be kept at room temperature for up to 14 days. Alternatively, a reaction can be heated, with. or without reflux, between about 25°C and about 200°C (or any integer between 25 and 200°C). The reaction time can be modified accordingly: more time at a low temperature and less time at a high temperature.

In certain embodiments for producing poly-alpha-1,3 hydroxypropyl glucan, a reaction can be heated at about 75°C for about 3 hours. A reaction to prepare poly-alpha-1,3-hydroxyethyl glucan can be heated at about 60°C for about 6 hours, for example. Therefore, a reaction to prepare a hydroxyalkyl poly-alpha-1,3-glucan of the present disclosure may optionally be heated to about 55°C to about 80°C (or any integer between 55 and 80°C). for about 2 hours to about 7 hours,

<img file="MX373205B_D0133.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY for example.

In certain embodiments for producing methyl poly-alpha-1,3-glucan, a reaction can be heated at about 55°C or 70°C for about 17 hours. A reaction to prepare ethyl poly-alpha-1,3-glucan can be heated at about 90°C for about 17 hours, for example. Therefore, a reaction mixture for preparing a poly-alkyl alpha-1,3-glucan of the present disclosure can be heated to about 55°C to about 95°C (or any integer between 55 and 95°C) for about 15 hours to about 20 hours, for example.

In certain embodiments for producing carboxymethyl poly-alpha-1,3-glucan, a reaction can be heated at about 55°C for about 3 hours. Thus, a reaction to prepare a carboxyalkyl poly-alpha-1,3-glucan in the present disclosure can be heated at about 50°C to about 60°C (or any integer between 50 and 60°C) for about 2 hours to about 5 hours, for example.

In certain embodiments for producing dihydroxyalkyl (eg, dihydroxypropyl) poly-alpha1,3-glucan ether, the poly-alpha-1,3-glucan is added to an alkali hydroxide (eg, tetraethylammonium hydroxide) solution ( For example, a solution of

<img file="MX373205B_D0134.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY approximately 20% by weight) to a final concentration or mass contribution of poly-alpha-1,3-glucan of approximately 4, 5, 6, 7 or 8% by weight (for example, -6.5 % in weigh). Following the heating/stirring steps to dissolve the poly-alpha-1,3-glucan, a suitable etherifying agent (eg, a dihydroxyalkyl chloride, such as 2,3-dihydroxypropyl chloride) can be added to a concentration final about 7, 8, 9, 10 or 11% by weight (eg -9.5% by weight). The resulting reaction can be held at about 50°C to about 60°C (or any integer between 50 and 60°C, eg, 55°C) for about 1.5-2.5 hours (eg, about 2 hours), eg , before neutralizing the reaction. Water-soluble dihydroxyalkyl poly-alpha-1,3-glucan can be produced by implementing these steps.

Optionally, a reaction of the present disclosure may be maintained under an inert gas, with or without heating. As used in the present description, the term "inert gas" refers to a gas that does not undergo chemical reactions under a set of specific conditions, such as those described to prepare a reaction of the present description.

All the components of the reactions described in the present description can be mixed with each other at the same

<img file="MX373205B_D0135.tif" />

132 ' IMPI

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY time and can be brought to the desired reaction temperature, whereby the temperature is maintained with or without stirring until the desired poly-alpha-1,3-glucan ether compound is formed. Alternatively, the mixed components can be left at room temperature as described above.

After etherification, the pH of a reaction can be neutralized. The neutralization of a reaction can be carried out with the use of one or more acids. The term neutral pH, as used herein, refers to a pH that is neither substantially acidic nor basic (for example, a pH of about 6-8 or about 6.0, 6.2, 6.4, 6.6, 6.8, 7.0, 7.2, 7.4, 7.6, 7.8 or 8.0). The various acids that can be used for this purpose include, but are not limited to, sulfuric acid, acetic acid, hydrochloric acid, nitric acid, any mineral (inorganic) acid, any organic acid, or any combination of these acids.

A poly-alpha-1,3-glucan ether compound produced in a reaction of the present disclosure may optionally be washed one or more times with a liquid that does not readily dissolve the compound. For example, poly-alpha-1,3-glucan ether can be washed with water, alcohol, acetone, aromatics, or any combination of these, depending on the solubility of the ether compound (wherein lack of

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY solubility is desirable for washing). Generally, a solvent comprising an organic solvent, such as alcohol, is preferred for washing a poly-alpha-1,3-glucan ether. A poly-alpha-1,3-glucan ether product can be washed one or more times with an aqueous solution containing methanol or ethanol, for example. For example, 7095 wt% ethanol can be used to wash the product. In another embodiment, a poly-alpha-1,3-glucan ether product can be washed with a solution of methanol:acetone (eg, 60:40). In certain embodiments, hot water (about 95-100°C) can be used to wash poly-alpha-1,3-glucan alkyl ethers (eg, poly-alpha-1,3-glucan ethyl) and poly-alpha-1,3-glucan ethyl ethers. alkyl hydroxyalkyl alpha-1,3-glucan (eg, poly-ethyl hydroxyethyl alpha-1,3-glucan).

A poly-alpha-1,3-glucan ether produced in the described reaction can be isolated. This stage can be carried out before or after the neutralization and/or washing stages with the use of a funnel, centrifuge, pressure filter or any other method or equipment known in the art that allows liquids to be removed from solids. For example, a Buchner funnel can be used to isolate a poly-alpha-1,3-glucan ether product. An isolated poly-alpha-1,3-glucan ether product can be dried using any method known in the art, such as

<img file="MX373205B_D0137.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY vacuum drying, air drying or freeze drying.

Any of the etherification reactions mentioned above can be repeated using a poly-alpha-1,3-glucan ether product as the starting material for further modification. This method may be suitable for increasing the DoS of an organic group and/or for adding one or more different organic groups to the ether product. For example, a dihydroxypropyl poly-alpha1,3-glucan ether product can be used as a substrate for further modification with dihydroxypropyl groups.

The structure, molecular weight, and degree of substitution of a poly-alpha-1,3-glucan ether product can be confirmed using various physiochemical analyzes known in the art, such as NMR spectroscopy and size exclusion chromatography ( SEQ).

The percentage of glycosidic linkages between the monomeric glucose units of poly-alpha-1,3-glucan used to prepare the poly-alpha-1,3-glucan ether compounds of the present disclosure that are alpha-1,3 is at least about 50%, 60%, 70%, 80%, 90%, 95%, 96%, 97%, 98%, 99%, or 100% (or any integer value between 50% and 100%). Therefore, in such embodiments, a poly-alpha-1,3-glucan has less than about 50%, 40%, 30%, 20%, 10%, 5%, 4%, 3%, 2%, 1 % or 0% (or any integer value between 0% and 50%) of glycosidic linkages that are not alpha-1,3.

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The poly-alpha-1,3-glucan used to prepare the poly-alpha-1,3-glucan ether compounds of the present disclosure is preferably linear/unbranched. In certain embodiments, the poly-alpha-1,3-glucan has no branch points or has less than about 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2% or 1% of the branch points as a percentage of the glycosidic linkages in the polymer. Examples of branch points include alpha-1,6 branch points.

The Mn or M_w of the poly-alpha-1,3-glucan used to prepare the poly-alpha-1,3-glucan ether compounds of the present disclosure can be from at least about 1,000 to about 600,000. Alternatively, the M_n or M_wcan be at least about 2,000, 3,000, 4,000, 5,000, 6,000, 7,000, 8,000, 9,000, 10,000, 15,000, 20,000, 25,000,

30,000, 35,000, 40,000, 45,000, 50,000, 75,000, 100,000,

150,000, 200,000, 250,000, 300,000, 350,000, 400,000,

450,000, 500,000, 550,000, or 600,000 (or any integer between 2,000 and 600,000), for example.

The poly-alpha-1,3-glucan used to prepare the poly-alpha-1,3-glucan ether compounds of the present disclosure can be produced enzymatically from sucrose with the use of one or more glycosyltransferase enzymes ( gtf). The poly-alpha-1,3-glucan product of this enzymatic reaction can be purified before it is used to prepare a

<img file="MX373205B_D0139.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY ether with the use of the described process. Alternatively, a poly-alpha-1,3-glucan product of a gtf reaction can be used with little or no processing to prepare poly-alpha-1,3-glucan ether compounds.

A suspension of poly-alpha-1,3-glucan can be used directly in any of the processes mentioned above to produce a polyalpha-1,3-glucan ether compound described herein. As used herein, a poly-alpha1,3-glucan suspension refers to a mixture comprising the components of a gtf enzyme reaction. A gtf enzyme reaction may include, in addition to the poly-alpha-1,3-glucan itself, various components, such as sucrose, one or more gtf enzymes, glucose, fructose, leucrose, buffer, FermaSure®, soluble oligosaccharides, primers of oligosaccharides, components of extracts of bacterial enzymes, borates, sodium hydroxide, hydrochloric acid, cell lysate, proteins and/or nucleic acids. Minimally, the components of a gtf enzyme reaction may include, in addition to the poly-alpha-1,3-glucan itself, sucrose, one or more gtf enzymes, glucose, and fructose, for example. In another example, the components of a gtf enzyme reaction may include, in addition to the poly-alpha-1,3-glucan itself, sucrose, one or more gtf enzymes, glucose, fructose, leucrose, and soluble oligosaccharides (and, optionally, components of

<img file="MX373205B_D0140.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY extracts of bacterial enzymes). It should be apparent that poly-alpha-1,3-glucan, when in suspension as described herein, has not been purified or washed. It should further be apparent that a suspension represents a complete gtf enzyme reaction or for which an observable amount of poly-alpha-1,3-glucan has been produced, which forms a solid since it is insoluble in the surrounding environment. the aqueous reaction (has a pH of 5-7, for example). A suspension of polyalpha-1,3-glucan can be prepared by creating a gtf reaction as described in US patent no. 7,000,000 or publications of US patent applications. no. 2013/0244288 and 2013/0244287, for example, which are incorporated herein by reference. A suspension of poly-alpha-1,3-glucan may, for example, take part in a reaction to produce a carboxyalkyl poly-alpha-1,3-glucan, such as poly-carboxymethyl alpha1,3-glucan.

Alternatively, a wet pellet of poly-alpha-1,3-glucan can be used directly in any of the above processes to produce a poly-alpha-1,3-glucan ether compound described herein. A poly-alpha-1,3-glucan wet agglomerate, as used herein, refers to a poly-alpha-1,3-glucan that has been separated (eg, filtered) from a

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY suspension and washing with water or an aqueous solution. A wet chipboard can be washed at least 1, 2, 3, 4, 5 or more times, for example. Poly-alpha-1,3-glucan does not dry out when preparing a wet agglomerate. A wet agglomerate is defined as wet due to water retention by the washed poly-alpha-1,3-glucan.

A wet pellet of poly-alpha-1,3-glucan can be prepared using any device known in the art for separating solids from liquids, such as a filter or centrifuge. For example, polyalpha-1,3-glucan solids in suspension can be collected on a Buchner funnel using a mesh screen over filter paper. The filtered wet agglomerate can be resuspended in water (eg, deionized water) and filtered one or more times to remove soluble components of the suspension, such as sucrose, fructose, and leucrose. As another example for preparing a wet agglomerate, the poly-alpha-1,3-glucan solids from a suspension can be collected as a pellet by centrifugation, resuspended in water (eg, deionized water), and pelletized and suspended. again one or more times. A wet agglomerate of poly-alpha-1,3-glucan can take part in a reaction to produce any ether compound of the present disclosure, such as carboxyalkyl poly-alpha-1,3-glucan

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY (for example, carboxymethyl poly-alpha-1,3-glucan).

The poly-alpha-1,3-glucan ether compounds described herein may be crosslinked using any means known in the art. Such crosslinking may be between the same poly-alpha-1,3-glucan ether compounds or between two or more different poly-alpha-1,3-glucan ether compounds. Furthermore, the crosslinks can be intermolecular and/or intramolecular.

A crosslinked poly-alpha-1,3-glucan ether compound can be prepared in the following manner, for example. One or more poly-alpha-1,3-glucan ether compounds can be dissolved in water or an aqueous solution to prepare a 0.2, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9o solution. 10% by weight of one or more ether compounds. The poly-alpha-1,3-glucan ether compound(s) may be dissolved or mixed using any process known in the art, such as by increasing the temperature, manual mixing, and/or homogenization (as described above). previously).

Next, a crosslinking agent is dissolved in the poly-alpha-1,3-glucan ether solution or mixture. The concentration of the crosslinking agent in the resulting solution can be from about 0.2 to 20% by weight or about 0.1, 0.2, 0.3, 0.4, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9 , 10, 15 or 20% by weight.

Examples of suitable crosslinking agents are

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY compounds containing boron and polyvalent metals, such as titanium or zirconium. Boron-containing compounds include boric acid, diborates, tetraborates, pentaborates, polymeric compounds such as Polybor®, polymeric boric acid compounds, and alkali borates, for example. These agents can be used to produce borate crosslinks between poly-alpha-1,3-glucan ether molecules. Titanium crosslinks can occur with the use of titanium IV containing compounds (eg, titanium ammonium lactate, titanium triethanolamine, titanium acetylacetonate, titanium polyhydroxyl complexes) as crosslinking agents. Zirconium crosslinks can occur with the use of zirconium-containing compounds IV (eg, zirconium lactate, zirconium carbonate, zirconium acetylacetonate, zirconium triethanolamine, zirconium diisopropylamine lactate, zirconium polyhydroxy complexes) as crosslinking agents. . Other examples of crosslinking agents useful in the present description are described in US patent nos. 4462917, 4464270, 4477360 and 4799550, incorporated herein by reference.

The pH of the solution or mixture containing one or more crosslinking agents and one or more poly-alpha-1,3-glucan ether compounds can be adjusted so that it is alkaline (for example, pH 8, 8.5, 9 , 9.5 or 10). The

<img file="MX373205B_D0144.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY pH modification can be done by any means known in the art, such as with a concentrated aqueous solution of an alkaline hydroxide such as sodium hydroxide. Dissolution of a crosslinking agent in a solution or mixture containing one or more poly-alpha-1,3-glucan ether compounds at alkaline pH results in crosslinking of one or more poly-alpha1 ether compounds, 3-glucan. EXAMPLES

The described invention is defined in more detail through the following examples. It should be understood that these examples, while indicating certain preferred aspects of the invention, are illustrative only. From the foregoing description and these examples, persons skilled in the art can determine the essential features of this invention and, without departing from the spirit and scope thereof, various changes and modifications may be made to the invention to adapt it to various uses and conditions. Materials

Acetone, sodium hydroxide, acetic acid and isopropanol were from EMD Chemicals (Billerica, ΜΆ). Methyl chloride, acetic acid, toluene, dimethyl sulfate, ethanol, and propylene oxide were from Sigma Aldrich (St. Louis, MO). Methanol and 2-propanol were

<img file="MX373205B_D0145.tif" />

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BDH Chemicals (Poole Dorset, UK).

Preparation of poly-alpha-1,3-glucan

Poly-alpha-1,3-glucan was prepared using a gtfJ enzyme preparation as described in US patent application publication no. 2013/0244288, which is incorporated herein by reference in its entirety.

Nuclear magnetic resonance method¹H (NMR) to determine the molar substitution of polyalpha-1,3-glucan ether derivatives

Approximately 30 mg of the poly-alpha1,3-glucan ether derivative was weighed into a vial on an analytical balance. The vial was removed from the balance and 1.0 mL of deuterium oxide was added to the vial. A magnetic stir bar was added to the vial and the mixture was stirred to suspend the solid. Deuterated sulfuric acid (50% v/v in D2O), 1.0 mL, was then added to the vial and the mixture was heated at 90°C for 1 hour to depolymerize and solubilize the polymer. The solution was allowed to cool to room temperature, and then a 0.8 mL portion of the solution was transferred to a 5 mm NMR tube using a glass pipette. An NMR spectrum was obtained¹!! Quantitative with the use of an Agilent VNMRS 400 MHz NMR spectrometer equipped with a self-changing 5 mm Quad probe. The spectrum was achieved at a spectral frequency of 399.945 MHz, with the use of a

<img file="MX373205B_D0146.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY spectral window of 6410.3 Hz, a capture time of 3.744 seconds, a delay between pulses of 10 seconds and 64 pulses. Time domain data were transformed using 0.50 Hz exponential multiplication.

Two regions of the resulting spectrum were integrated for NMR analysis of hydroxypropyl poly-alpha-1,3-glucan: one integral from 1.1 ppm to 1.4 ppm, representative of the three methyl protons of all isopropyl groups present; and an integer from 4.7 ppm to 5.6 ppm, representative of the anomeric protons of the glucose rings. The integral of the isopropylmethyl region was divided by 3 to obtain a measure of the OCH2CH(CH3)O groups that were present. The molar substitution for the OCH2CH(CH3)O groups was then calculated by dividing the measure of the OCH2CH(CH3)O groups by the measure of all glucose rings present (the integral value of the anomeric protons).

Two regions of the resulting spectrum were integrated for NMR analysis of methyl poly-alpha-1,3-glucan: an integral from 3.0 ppm to 4.2 ppm representative of the six glucan protons plus OCH3 protons, and an integral from 4.6 ppm at 5.6 ppm representative of the anomeric protons of the glucose rings. The integral value of this latter region was multiplied by six to obtain the integral value of the other six glycan protons. The

<img file="MX373205B_D0147.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY integral calculated for the six non-anomeric protons of glucan was subtracted from the integral of the region from 3.0 ppm to 4.2 ppm to obtain the integral contribution of the OCH3 protons. This integral value was divided by 3.0 to obtain a measure of the OCH3 groups that are present. The degree of methylation was then calculated by dividing the size of OCH3 groups by the size of all glucose rings present (the integral value of anomeric protons).

Regarding the NMR analysis of carboxymethyl poly-alpha-1,3-glucan, the chemical shifts of the lines in the spectrum were related to the signal for the alpha anomeric protons without substitution at C2OH. This signal should be the third group of peaks from the leftmost edge of the spectrum. The leftmost signal in this group of peaks was determined to be 5222 ppm. Five regions of the mentioned spectrum were integrated: an integral from 5.44 ppm to 4.60 ppm represents all anomeric protons; the integrals from 4.46 ppm to 4.41 ppm and from 4.36 ppm to

4.32 ppm were from carboxymethyl CH2 at the C2 position adjacent to C1HOH either alpha or beta; the integral from 4.41 ppm to 4.36 ppm is from carboxymethyl CH2 at the C4 position; and the integral from 4.24 ppm to 4.17 ppm was from carboxymethyl CH₂ at the C6 position. The degree of carboxymethylation at positions 2, 4 and 6 was then calculated by the

<img file="MX373205B_D0148.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY division of the integrals for the OCH2COOH groups by two and then division of these results by the integration for all anomeric protons. A total degree of substitution was obtained by adding together the three individual degrees of substitution.

Measurement of the degree of polymerization

The degree of polymerization (DP) was determined by size exclusion chromatography (SEC). For SEC analysis, dry poly-alpha-1,3-glucan ether derivative was dissolved in phosphate buffered saline (PBS) (0.02-0.2 mg/ml). An Alliance™ 2695 liquid chromatograph from Waters Corporation (Milford, MA) coupled with three on-line detectors was used as the chromatographic system: a Waters 410 differential refractometer, a Heleos™ 8+ multi-angle light scattering photomer from Wyatt Technologies (Santa Barbara, CA) and a Wyatt Technologies ViscoStar™ Differential Capillary Viscometer. The columns used for SEC were two Tosoh Haas Bioscience TSK GMPWxl g3K and g4K G3000PW and G4000PW polymeric columns for aqueous polymers. The mobile phase was PBS. The chromatographic conditions used were 30°C in the column and detector compartments, 30°C in the sample and injector compartments, a flow rate of 0.5 ml/min, and an injection volume of 100 pL.

The software packages used for data reduction

<img file="MX373205B_D0149.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY were Wyatt's Astra version 6 (triple detection method with column calibration).

Homogenization

Homogenization was performed with an IKA ULTRA TURRAX T25 digital homogenizer (IKA, Wilmington, NC). Example 1 Preparation of poly-alpha-1,3-hydroxypropyl glucan

This example describes the production of the glucan ether derivative, poly-hydroxypropyl alpha-1,3-glucan.

g poly-alpha-1,3-glucan (number average molecular weight [M_n] = 71127) were mixed with 101 g of toluene and 5 ml of 20% sodium hydroxide. This preparation was stirred in a 500 ml glass beaker on a magnetic stirrer at 55°C for 30 minutes. The preparation was then transferred to a stirred tube reactor after which 34 g of propylene oxide was added; then the reaction was stirred at 75°C for 3 hours. The reaction was then quenched with 20 g of acetic acid and the hydroxypropyl polyalpha-1,3-glucan solids thus formed were filtered with a Buchner funnel. The solids were then washed in a beaker with 70% ethanol and dried in a vacuum oven with a light nitrogen purge to constant dryness. The molar substitution (MS) of the dry product was reported by NMR and was 3.89.

Therefore, the ether derivative was prepared and isolated.

<img file="MX373205B_D0150.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY of glucan, poly-alpha-1,3-hydroxypropyl glucan.

Example 2

Preparation of poly-alpha-1,3-hydroxyethyl glucan

This example describes the production of the glucan ether derivative, poly-alpha-1,3-hydroxyethyl glucan.

g poly-alpha-1,3-glucan (M_n = 71127) were mixed with 150 ml of isopropanol and 40 ml of 30% sodium hydroxide. This preparation was stirred in a 500 ml glass beaker on a magnetic stirrer at 55°C for 1 hour, and then stirred overnight at room temperature. The preparation was then transferred to a stirred tube reactor after which 15 g of ethylene oxide was added; then the reaction was stirred at 60°C for 6 hours. The reaction was then allowed to stand in the sealed shaker tube overnight (approximately 16 hours) before neutralizing with 20.2 g of acetic acid to form poly-alpha-1,3-hydroxyethyl glucan solids. Solids were filtered using a Buchner funnel with 35 micron filter paper. The solids were then washed in a beaker by adding a mixture of methanol:acetone (60:40 v/v) and stirring with a stir bar for 20 minutes. The methanol:acetone mixture was then filtered and separated from the solids. This washing step was repeated twice. The solids, which were slightly brown/beige in color, were dried in a

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY vacuum with a nitrogen purge. The hydroxyethyl poly-alpha1,3-glucan product was soluble in 10% NaOH solution. The MS of the dry product was reported by NMR and was 0.72.

Therefore, the glucan ether derivative, poly-alpha-1,3-hydroxyethyl glucan, was prepared and isolated.

Example 3

Preparation of poly-alpha-1,3-ethyl glucan

This example describes the production of the glucan ether derivative, poly-ethyl alpha-1,3-glucan.

The poly-alpha-1,3-glucan was added to a stirring tube, after which sodium hydroxide (1-70% solution) and ethyl chloride were added to cause a reaction. The reaction was heated to 25-200 °C and held at that temperature for 1-48 hours before quenching the reaction with acetic acid. The solid thus formed is collected by vacuum filtration and washed, vacuum dried at 20-25°C and analyzed by NMR and SEC to determine the molecular weight and degree of substitution (DoS) of poly-alpha1 ethyl,3-glucan.

Therefore, the glucan ether derivative, poly-ethyl alpha1,3-glucan, is prepared and isolated.

Example 4

Preparation of ethyl hydroxyethyl poly-alpha-1,3-glucan

This example describes the production of the ether derivative

<img file="MX373205B_D0152.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY of glucan, poly-alpha-1,3-glucan of ethyl hydroxyethyl.

The poly-alpha-1,3-glucan was added to a shaker tube, after which sodium hydroxide (1-70% solution) was added. Ethyl chloride is then added followed by an ethylene oxide/ethyl chloride mixture to cause a reaction. The reaction is slowly heated to 25-200°C and held at that temperature for 1-48 hours before neutralizing with acetic acid. The solid thus formed is collected by vacuum filtration and washed with hot water, vacuum dried at 20-70°C and analyzed by NMR and SEC to determine the molecular weight and DoS of poly-alpha-1. Ethyl hydroxyethyl ,3-glucan.

Therefore, the glucan ether derivative, hydroxyethyl poly-alpha1,3-glucan, is prepared and isolated. Example 5 Preparation of poly-methyl alpha-1,3-glucan

This example describes the production of the glucan ether derivative, poly-methyl alpha-1,3-glucan.

g poly-alpha-1,3-glucan (M_n = 71127) were mixed with 40 ml of 30% sodium hydroxide and 40 ml of 2-propanol and stirred at 55°C for 1 hour to produce the alkaline poly-alpha1,3-glucan. This preparation was then filtered using a Buchner funnel. Then the alkaline poly-alpha-1,3-glucan was mixed with 150 ml of 2-propanol to produce a suspension. In a stirred tube reactor,

<img file="MX373205B_D0153.tif" />

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The MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY placed this suspension and added 15 g of methyl chloride to produce a reaction. The reaction was stirred at 70°C for 17 hours. The resulting poly-methyl alpha-1,3-glucan solid was filtered and neutralized with 20 ml of 90% acetic acid, followed by three washes with 200 ml of ethanol. NMR analysis was performed which indicated the DoS of the methyl poly-alpha-1,3-glucan product to be 1.2.

Table 1 provides a list of DoS measurements for various samples of methyl poly-alpha-1,3-glucan prepared using methods that have certain modifications compared to the method described above (see Table 1). The mercerization step (alkaline treatment of poly-alpha-1,3-glucan before adding the methylation reagent) for each of the processes listed in Table 1 was carried out for 1 hour, as mentioned above.

Table 1

Preparation of poly-methyl alpha-1,3-glucan with the use of various mercerization and methylation conditions

<td colspan="3">Mercerization conditions</td><td colspan="3">Methylation conditions</td><td></td>

<td>glucan min</td><td>Temp(°C)</td><td>Solvent</td><td>Reagent</td><td>Weather (hours)</td><td>Temp(°C)</td><td>Two</td>

<td> 71127</td><td>RT</td><td>Toluene (140 ml)</td><td>AMD^a(50 mi)</td><td> 17</td><td> 50</td><td> 1.51</td>

<td> 71127</td><td> 55</td><td>2-propanol (150 ml)</td><td>CH₃C1 (15g)</td><td> 17</td><td> 70</td><td> 1.2</td>

<td> 71127</td><td> 55</td><td>2-propanol (150 ml)</td><td>CH3Cl (25g)</td><td> 24</td><td> 70</td><td> 1.38</td>

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<td colspan="3">Mercerization conditions</td><td colspan="3">Methylation conditions</td><td></td>

<td>glucan M_n</td><td>Temp(°C)</td><td>Solvent</td><td>Reagent</td><td>Time (hours)</td><td>Temp(°C)</td><td>Two</td>

<td> 25084</td><td> 55</td><td>2-propanol (150 ml)</td><td>CH₃C1 (30g)</td><td> 34</td><td> 70</td><td> 1.0</td>

<td> 25084</td><td> 55</td><td>2-propanol (150 ml)</td><td>CH₃C1 (25g)</td><td> 24</td><td> 70</td><td> 0.39</td>

^a dimethyl sulfate

Therefore, the glucan ether derivative, poly-methyl alpha-1,3-glucan, was prepared and isolated.

Example 6

Preparation of water-soluble poly-methyl alpha-1,3-glucan

This example describes the production of water-soluble poly-methyl alpha-1,3-glucan.

g of methyl poly-alpha-1,3-glucan (DoS = 1.38), as prepared in Example 5 (Table 1), were mixed with 40 ml of 30% sodium hydroxide and 40 ml of 2-propanol and stirred at 55°C for 1 hour. This mixture was then filtered using a Buchner funnel. 150 ml of 2-propanol was added to produce a suspension, which was then placed in a shaker tube reactor. 15 g of methyl chloride was added to the suspension to cause a reaction. The reaction was stirred at 55°C for 17 hours, then neutralized with 10 mL of acetic acid and mixed with 200 mL of acetone to precipitate the product. The product was then washed with two more washes of 200 ml of acetone.

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NMR analysis of the methyl poly-alpha-1,3-glucan product indicated that it had a DoS of 2.

A solution of the methyl poly-alpha-1,3-glucan product in water was prepared by dissolving 0.2 g of the product in 9.8 g of water and mixing at room temperature. A clear solution formed, indicating that the methyl polyalpha-1,3-glucan product was soluble in water.

Therefore, the water-soluble poly-methyl alpha-1,3-glucan was prepared and isolated.

Example 7

Preparation of hydroxyalkyl methyl poly-alpha-1,3-glucan

This example describes the production of the glucan ether derivative, hydroxyalkyl methyl poly-alpha-1,3-glucan.

Poly-alpha-1,3-glucan was added in a pot, then sodium hydroxide (5-70% solution) was added. This preparation is stirred for 0.5-8 hours. Methyl chloride is then added to the pot to produce a reaction, which is then heated to 30-100°C for up to 14 days. Alkylene oxide (eg, ethylene oxide, propylene oxide, butylene oxide, etc.) is then added to the reaction while controlling the temperature. The reaction was heated to 25-100°C for up to 14 days before neutralizing with acid. The solid product thus formed is filtered, washed and dried.

Therefore, the glucan ether derivative, poly-alpha373205

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1,3-Hydroxyalkyl methyl glucan, prepare and isolate. Depending on the alkylene oxide used after the methylation step, examples of this derivative include poly-hydroxyethyl methyl alpha1,3-glucan, poly-hydroxypropyl methyl alpha-1,3-glucan, and poly-alpha-1,3 -Hydroxybutyl methyl glucan.

Example 8

Preparation of carboxymethyl hydroxyethyl poly-alpha-1,3-glucan

This example describes the production of the glucan ether derivative, carboxymethyl hydroxyethyl poly-alpha-1,3-glucan.

The poly-alpha-1,3-glucan is added to an aliquot of a substance such as isopropanol or toluene in a 400-mL shaker tube, after which sodium hydroxide (1-70% solution) is added. ). This preparation is stirred for up to 48 hours. Monochloroacetic acid is then added to produce a reaction, which is then heated to 25-100°C for up to 14 days. Ethylene oxide is then added to the reaction, which is then heated to 25-100°C for up to 14 days before neutralizing with acid (eg acetic, sulfuric, nitric, hydrochloric, etc.). The solid product thus formed is collected by vacuum filtration, washed and dried.

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Therefore, the glucan ether derivative, hydroxyethyl carboxymethyl polyalpha-1,3-glucan, is prepared and isolated.

Example 9

Preparation of sodium carboxymethyl hydroxyethyl poly-alpha-1,3-glucan

This example describes the production of the glucan ether derivative, sodium carboxymethyl hydroxyethyl poly-alpha-1,3-glucan.

The poly-alpha-1,3-glucan is added to an aliquot of an alcohol, such as isopropanol, in a 400 ml shaker tube, then sodium hydroxide (1-70% solution) is added. This preparation is stirred for up to 48 hours. Sodium monochloroacetate is then added to produce a reaction, which is then heated to 25-100°C for up to 14 days. Ethylene oxide is then added to the reaction, which is then heated to 25-100°C for up to 14 days before neutralizing with acid (eg acetic, sulfuric, nitric, hydrochloric, etc.). The solid product thus formed is collected by vacuum filtration, washed and dried.

Therefore, the glucan ether derivative, sodium carboxymethyl hydroxyethyl polyalpha-1,3-glucan, is prepared and isolated.

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Example 10

Preparation of hydroxypropyl carboxymethyl poly-alpha-1,3-glucan

This example describes the production of the glucan ether derivative, carboxymethyl hydroxypropyl poly-alpha-1,3-glucan.

The poly-alpha-1,3-glucan is added to an aliquot of a substance such as isopropanol or toluene in a 400-mL shaker tube, after which sodium hydroxide (1-70% solution) is added. ) . This preparation is stirred for up to 48 hours. Monochloroacetic acid is then added to produce a reaction, which is then heated to 25100°C for up to 14 days. Propylene oxide is then added to the reaction, which is then heated to 25100°C for up to 14 days before neutralizing with acid (eg acetic, sulfuric, nitric, hydrochloric, etc.). The solid product thus formed is collected by vacuum filtration, washed and dried.

Therefore, the glucan ether derivative, poly-carboxymethyl hydroxypropyl alpha1,3-glucan, is prepared and isolated.

Example 11

Preparation of sodium carboxymethyl hydroxypropyl poly-alpha-1,3-glucan

This example describes the production of the ether derivative

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY of glucan, sodium carboxymethyl hydroxypropyl poly-alpha-1,3-glucan.

The poly-alpha-1,3-glucan is added to an aliquot of a substance such as isopropanol or toluene in a 400-mL shaker tube, after which sodium hydroxide (1-70% solution) is added. ). This preparation is stirred for up to 48 hours. Sodium monochloroacetate is then added to produce a reaction, which is then heated to 25-100°C for up to 14 days. Propylene oxide is then added to the reaction, which is then heated to 25-100°C for up to 14 days before neutralizing with acid (eg acetic, sulfuric, nitric, hydrochloric, etc.). The solid product thus formed is collected by vacuum filtration, washed and dried.

Therefore, the glucan ether derivative, sodium carboxymethyl hydroxypropyl poly-alpha1,3-glucan, is prepared and isolated.

Example 12

Preparation of poly-alpha-1,3-glucan suspension and wet agglomerate with the use of GtfJ enzyme

This example describes the production of a wet pellet or suspension of poly-alpha-1,3-glucan using a reaction catalyzed by a glycosyltransferase enzyme, gtfJ. These compositions were used in Examples 13 and 14

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY to prepare poly-alpha-1,3-glucan ether compounds.

More information related to the gtfJ enzyme can be found in US patent no. 7,000,000 and US patent application publication nos. 2013/0244288 and 2013/0244287 (which are incorporated herein by reference).

To prepare a suspension of poly-alpha-1,3-glucan, an aqueous solution (0.75 l) containing sucrose (100 g/l), potassium phosphate buffer (20 mM), and FermaSure® (500 ppm) was prepared and it was adjusted to a pH of 6.8-7.0. Then, this solution was quenched with gtfJ enzyme extract (50 units/1). The enzyme reaction solution was kept at 20-25°C for 48 hours. A suspension was formed since the poly-alpha-1,3-glucan synthesized in the reaction was insoluble in water. This suspension was then used, without any filtration, to prepare carboxymethyl poly-alpha-1,3-glucan (see Example 13).

The gtfJ enzyme reaction was carried out as mentioned above to prepare a wet pellet of poly-alpha-1,3-glucan. The poly-alpha-1,3-glucan solids produced in the reaction were collected using a Buchner funnel fitted with a 325 mesh screen over 40 micron filter paper. The filtered poly-alpha-1,3-glucan solids were resuspended in deionized water and filtered two more times as mentioned above to

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OF THE PROPERTY

INDUSTRIAL remove sucrose, fructose and other low molecular weight soluble by-products. The wet agglomerate of poly-alpha-1,3-glucan solids was then used to prepare carboxymethyl poly-alpha-1,3-glucan (see Example 14).

Therefore, a suspension and an "agglomerate" were prepared. wet poly-alpha-1,3-glucan. These types of poly-alpha-1,3-glucan preparations can be used as substrates to prepare poly-alpha-1,3-glucan ether compounds. Example 13 Preparation of carboxymethyl poly-alpha-1,3-glucan from suspension of poly-alpha-1,3-glucan

This example describes the production of the carboxymethyl poly-alpha-1,3-glucan ether compound using a suspension of poly-alpha-1,3-glucan as prepared in Example 12. This suspension is not neither filtered nor washed and thus comprised components of the glycosyltransferase reaction which is used to synthesize poly-alpha1,3-glucan.

The poly-alpha-1,3-glucan suspension (500 g) was placed in a 1 1 coated reaction vessel fitted with a thermocouple to monitor temperature, a condenser connected to a recirculating bath, and a magnetic stir bar. Solid sodium hydroxide (75 g) was added to the suspension to produce a preparation with 15 wt% sodium hydroxide. This preparation was heated to 25°C in

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY a heating plate. The preparation was then stirred for 1 hour before the temperature was increased to 55°C. Sodium chloroacetate (227.3 g) was added in the preparation and the reaction temperature was kept at 55°C for 3 hours. The reaction was then quenched with acetic acid (90%). The solid was collected by vacuum filtration and washed with ethanol (70%) four times, vacuum dried at 20-25°C and analyzed by NMR and SEC for molecular weight and DoS. The solid material obtained was identified as water-soluble carboxymethyl poly-alpha-1,3-glucan with a DoS of 0.3 and a M_w of 140,000.

Therefore, a poly-alpha-1,3-glucan suspension containing components of a glycosyltransferase reaction can be used as a substrate to prepare poly-alpha-1,3-glucan ether compounds. This result indicates that the products of a glycosyltransferase reaction used to synthesize poly-alpha-1,3-glucan do not require any processing (such as washing or purification of the poly-alpha-1,3-glucan product) before they are used in reactions to synthesize poly-alpha-1,3-glucan. produce poly-alpha-1,3-glucan ether compounds. Example 14 Preparation of carboxymethyl poly-alpha-1,3-glucan from wet poly-alpha-1,3-glucan agglomerate

This example describes the production of the compound

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY ether, poly-alpha-1,3-glucan of carboxymethyl, with the use of a wet agglomerate of poly-alpha-1,3-glucan as prepared in Example 12. This wet agglomerate is not dried before using it in this example.

The poly-alpha-1,3-glucan wet pellet (500 g) was placed in a 11-lined reaction vessel fitted with a thermocouple to monitor temperature, a condenser connected to a recirculating bath, and a vertical stirrer. Isopropanol (500 ml) and solid sodium hydroxide (79.1 g) were added to the wet cake to produce a preparation with 15 wt% sodium hydroxide. This preparation was heated to 25°C on a hot plate and then stirred for 1 hour before the temperature was increased to 55°C. Sodium chloroacetate (227.3 g) was added in the preparation and the reaction temperature was kept at 55°C for 3 hours. The reaction was then quenched with acetic acid (90%). The solids were collected by vacuum filtration and washed with ethanol (70%) four times, vacuum dried at 20-25°C and analyzed by NMR and SEC for molecular weight and DoS. The solid material obtained was identified as water-soluble carboxymethyl polyalpha-1,3-glucan with a DoS of 0.7 and an M_w of 250,000.

Therefore, a wet pellet of poly-alpha-1,3-glucan can be used as a substrate to prepare

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY poly-alpha-1,3-glucan ether compounds. This result indicates that the poly-alpha-1,3-glucan product of a glycosyltransferase reaction can be used with little processing (washing with water) in reactions to produce poly-alpha-1,3-glucan ether compounds.

Example 15

Preparation of sodium carboxymethyl poly-alpha-1,3-glucan

This example describes the production of the glucan ether derivative, sodium carboxymethyl poly-alpha-1,3-glucan.

g poly-alpha-1,3-glucan (M_w [weight average molecular weight] = 236.854) were added in 200 ml of isopropanol in a distillation flask with 500 ml capacity fitted with a thermocouple to monitor temperature and a condenser connected to a recirculating bath and a magnetic stir bar. 40 mL of sodium hydroxide (15% solution) was added dropwise into the preparation, which was then heated to 25°C on a hot plate. The preparation was stirred for 1 hour before the temperature was increased to 55°C. Sodium chloroacetate (12g) was then added to produce a reaction, which was held at 55°C for 3 hours before being neutralized with 90% acetic acid. The solid thus formed was collected by vacuum filtration and washed with ethanol (70%) four times, vacuum dried at 20-25°C and

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INSTITUTO MEXICANO DE LA PROPERDAD INDUSTRIAL was analyzed by NMR and SEC to determine molecular weight and DoS. The solid material obtained was identified as water-soluble sodium carboxymethyl polyalpha-1,3-glucan with a DoS of 0.5 and a M_w of 580,000.

Table 2 provides a list of DoS measurements for various samples of sodium carboxymethyl poly-alpha-1,3-glucan prepared using the method described above. The poly-alpha-1,3-glucan starting material had various molecular weights (Table 2).

Table 2

Sodium carboxymethyl poly-alpha-1,3-glucan DoS prepared from poly-alpha-1,3-glucan

<td colspan="2">CMG sample designation</td><td>M_w of poly-alpha-1,3-glucan raw material</td><td>Two</td>

<td>1A</td><td> (35)</td><td> 140287</td><td> 0.5</td>

<td>BI</td><td> (36)</td><td> 140287</td><td> 0.9</td>

<td>1 C</td><td> (39)</td><td> 140287</td><td> 1</td>

<td>ID</td><td> (44)</td><td> 88445</td><td> 0.7</td>

<td>1E</td><td> (47)</td><td> 278858</td><td> 0.7</td>

<td>1F</td><td> (58)</td><td> 248006</td><td></td>

<td>1G</td><td> (67)</td><td> 236854</td><td> 0.5</td>

<td>1 HOUR</td><td> (72)</td><td> 236854</td><td> 0.9</td>

<td> 11</td><td> (-41)</td><td> 200000</td><td> 0.5</td>

<td>1J</td><td> (-39)</td><td> 168584</td><td> 0.5</td>

Therefore, the glucan ether derivative, sodium carboxymethyl poly-alpha-1,3-glucan, was prepared and isolated.

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Example 16

Effect of dissolution method on the viscosity of solutions of poly-alpha-1,3-carboxymethyl glucan (CMG)

This example describes the viscosity of CMG solutions prepared using different dissolution techniques.

A sample of CMG (1G, Table 2) was prepared as described in Example 15 and then dissolved using three different methods:

a) homogenization: 1 g of CMG (1G) was added in deionized (DI) water (49 g) to give a 2 wt% CMG preparation, which was then homogenized for 12-15 seconds at 20,000 rpm to dissolve the CMG. Filtering was not necessary because there were no particulates in the solution.

b) Mechanical mixing: deionized water (49 g) was stirred at 400 rpm with the use of a vertical mixer equipped with a paddle. 1 g of CMG (1G) was added gradually to the vortex created by the mixer to give a 2 wt% CMG preparation which was then heated to 25°C using a water bath and hot plate to obtain uniform heating. The preparation was stirred until all

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY the CMG was dissolved. The resulting solution was then vacuum filtered to remove any particulate matter.

c) Manual stirring: 1 g of the CMG (1G) was added in 49 g of deionized water to give a 2 wt% CMG preparation which was then manually stirred for 10-15 seconds and all allowed to settle. overnight to complete dissolution. The resulting solution was then vacuum filtered to remove any particulate matter.

To determine the viscosity of each CMG solution at various shear rates, dissolved CMG samples were exposed to shear rates of 10, 60, 150, and 250 rpm with a Brookfield III+ rheometer equipped with a recirculating bath to control temperature ( 20°C) and a SC4-21 Thermosel® spindle. Shear rate was increased with a gradient program that increased from 10-250 rpm and shear rate increased by 4.9 (1/s) every 20 seconds. The results of this experiment are listed in Table 3.

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eleventh

<td rowspan="2"></td><td colspan="2"> 1</td><td rowspan="2"> 168.8</td><td rowspan="2"> 161.6</td><td rowspan="2"> 327.2</td>

<td>Goo</td><td>(cPs) at 250 ] ....</td>

<td></td><td></td><td> 1</td><td></td><td></td><td></td>

<td></td><td></td><td>either</td><td></td><td></td><td></td>

<td></td><td>Ό</td><td>IT</td><td></td><td></td><td></td>

<td></td><td> 01</td><td></td><td></td><td></td><td></td>

<td></td><td>You</td><td></td><td></td><td></td><td></td>

<td></td><td>-rl</td><td>(C</td><td></td><td></td><td></td>

<td></td><td>C.Q.</td><td></td><td></td><td></td><td></td>

<td></td><td> 0</td><td></td><td>CO</td><td></td><td></td>

<td></td><td>OR</td><td>ω</td><td> •</td><td> •</td><td> •</td>

<td></td><td>ω</td><td>cu</td><td></td><td>kD</td><td>NC</td>

<td></td><td>•H</td><td></td><td>either</td><td>(You</td><td></td>

<td> 0</td><td> &gt;</td><td></td><td>cn</td><td>r4</td><td></td>

<td>SW</td><td></td><td> &amp;</td><td></td><td></td><td></td>

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<td>hey</td><td>ω</td><td></td><td>in</td><td></td><td></td>

<td>YOU</td><td> 0</td><td> &gt;</td><td>&lt;o</td><td>CO</td><td></td>

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<td>ω</td><td></td><td> £</td><td></td><td></td><td></td>

<td>-rl</td><td></td><td>CU</td><td></td><td></td><td></td>

<td> &gt;</td><td></td><td>you</td><td></td><td></td><td></td>

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<td></td><td> &lt;0</td><td>fH</td><td></td><td></td><td></td>

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<td>Φ</td><td> 0</td><td>(OR</td><td></td><td></td><td></td>

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in

<img file="MX373205B_D0169.tif" />

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MEXICAN INSTITUTE

OF THE PROPERTY

INDUSTRIAL

The results summarized in Table 3 indicate that the method of CMG dissolution can have an effect on solution viscosity. The manually stirred or mechanically stirred samples showed a lower viscosity compared to the sample that was homogenized. Apparently, the filtration step after manual agitation or mechanical agitation has a considerable effect in reducing the viscosity.

Therefore, a CMG solution prepared by homogenization had a higher viscosity compared to CMG solutions prepared by manual stirring and mechanical stirring.

Example 17

Effect of shear rate on CMG viscosity

This example describes the effect of shear rate on the viscosity of various CMG solutions, where the solutions were prepared using CMGs with different molecular weights. It is shown that the CMG solutions exhibited significant pseudoplastic behavior. Therefore, the addition of CMG to a liquid can modify the rheological behavior of the liquid.

Various CMG solutions with different molecular weights were prepared as described in Example 16 by homogenization. Specifically, to prepare a 2% by weight solution of each of these samples,

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY added 1 g of CMG (particular samples from Table 2) in 49 g of deionized water. Each preparation was then homogenized for 12-15 seconds at 20,000 rpm to dissolve the CMG.

The viscosity of each CMG solution was measured as in Example 16. The results of this experiment are listed in Table 4.

Table 4

Viscosity of CMG solutions with different molecular weights at various shear rates

<td>CMG Sample</td><td>CMG Burden</td><td>Goo (cps) to 10rpm</td><td>Viscosity (cPs) at 60 rpm</td><td>Goo (cps) at 150rpm</td><td>Viscosity (cPs) at 250rpm</td>

<td>1 C</td><td> 2%</td><td> 93</td><td> 73</td><td> 64</td><td> 60</td>

<td>ID</td><td> 2%</td><td> 10</td><td> 10</td><td> 10</td><td> 10</td>

<td>1E</td><td> 2%</td><td> 1242</td><td> 713.9</td><td> 504</td><td> 414.6</td>

<td>1F</td><td> 2%</td><td> 5393</td><td> 1044</td><td> 656</td><td> 454</td>

<td>1J</td><td> 2%</td><td> 8379.3</td><td> 980.7</td><td> 442.4</td><td> 327.2</td>

The results summarized in Table 4 indicate that the viscosity of most CMG solutions decreases as the shear rate increases. This observation means that the CMG solutions demonstrate significant shear thinning behavior.

Therefore, when CMG dissolves in aqueous solution, it not only modifies the viscosity of the solution, but also the rheological properties of the solution. For the

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Therefore, the CMG can be added to an aqueous liquid to modify its rheological profile.

Example 18

Effect of temperature on viscosity

This example describes the effect of temperature on the viscosity of CMG solutions.

A 2 wt% CMG solution (1G, Table 2) was prepared as described in Example 16 with the homogenization method. The viscosity of the CMG solution was measured using a Brookfield DV III+ rheometer equipped with a recirculating bath for temperature control and a Thermosel® SC4-21 spindle. The cutting speed was kept constant at 60 rpm while the temperature was increased by 2°C every 2 minutes. The temperature was increased from 20°C to 70°C and viscosity measurements were taken at certain temperatures. The results are shown in Table 5. Table 5

Effect of temperature on the viscosity of CMG solutions

<td>Temperature (°C)</td><td>Viscosity (cPs) at 60 rpm</td>

<td> 20</td><td> 784.3</td>

<td> 40</td><td> 491.4</td>

<td> 50</td><td> 435.6</td>

<td> 60</td><td> 404.6</td>

<td> 70</td><td> 365.8</td>

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The results summarized in Table 5 indicate a decrease in viscosity as temperature increases.

Example 19

Effect of degree of substitution on viscosity

This example describes the effect of CMG DoS on the viscosity of CMG in solution.

Two 2 wt% CMG solutions (1G and 1H, Table 2) were prepared as described in Example 16 using the homogenization method. The viscosity of each solution was measured according to Example 16 and the results are shown in Table 6.

Table 6

Effect of degree of substitution on viscosity

<td>CMG Sample</td><td>Two</td><td>Viscosity (cPs) at 10 rpm</td><td>Viscosity (cPs) at 60 rpm</td><td>Viscosity (cPs) at 150 rpm</td><td>Goo (cps) at 250rpm</td>

<td>1G</td><td> 0.5</td><td> 8379.3</td><td> 980.8</td><td> 442.4</td><td> 327.2</td>

<td>1 HOUR</td><td> 0.9</td><td>N/A</td><td>N/A</td><td> 61.8</td><td> 57.2</td>

The results summarized in Table 6 indicate that as the DoS of the CMG polymer increases, a reduction in viscosity occurs. It is highlighted that the Brookfield rheometer failed to accurately measure the viscosity at low shear rates (10 and 60 rpm) for the CMG with a DoS of 0.9. However, as the shear rate

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY was increased to 150 rpm and 250 rpm for this CMG, the torque on the instrument was increased and the viscosity measurement became reliable.

Therefore, the CMG with a lower DoS has a higher viscosity-aggregating activity than the CMG with a higher DoS.

Example 20

Effect of pH on CMG viscosity

This example describes the effect of pH on the viscosity of CMG in solution.

A 2 wt% CMG solution (1G, Table 2) was prepared as described in Example 16 using the homogenization method. The solution was divided into four aliquots, which were adjusted to pH 3.5, pH 4.5, pH 4.8, or pH 5.0 using citric acid.

A second 2 wt% CMG solution (1G, Table 2) was prepared as in Example 16 using the homogenization method. The solution was divided into two aliquots. One aliquot was adjusted to pH 3.0 with citric acid and the second aliquot was adjusted to pH 12 with sodium hydroxide.

The viscosity of each of the above preparations was measured according to Example 16 and the results are shown in Table 7.

CMG solutions were prepared at 1% by weight, 1.5% by weight

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY or 2% by weight (II and 1J, Table 2) as in Example 16 with the homogenization method. The solutions were then adjusted to pH 3, pH 3.5, pH 4, pH 5, pH 6, or pH 7 with glacial acetic acid. The viscosity of certain preparations was measured according to Example 16 (results are shown in Table 7), but with the following modifications. Certain viscosity measurements were made with a Brookfield III+ rheometer equipped with a Thermosel® SC4-21 or SC4-18 spindle. Viscosity measurements were made at shear rates of 10 rpm, 58.98 rpm, 152 rpm, and 232.5 rpm.

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<td rowspan="8">Table 7 Viscosity of CMG solutions at various pH values</td><td>Viscosity (cPs) at 250 rpm</td><td>9' LF</td><td> 440 1</td><td>00 &lt;0 00 in</td><td> 440 |</td><td>9*ee£</td><td> ¡216 1</td><td>Viscosity (cPs) at 232.5 rpm</td><td>93*3^1l</td><td>I Z8'60T</td><td>in in NC</td><td> ¡76.37 |</td><td>m in 00 in</td><td> 47.6 1</td><td>N/A |</td><td>N/A |</td><td>_n/a</td><td> ¡354.4 |</td><td> ¡234.18 |</td><td>3*91d</td><td> ¡183.15 |</td><td> ¡263.2 |</td><td> ¡222.4 |</td><td>9ΈΔδ</td><td> ¡126.72 |</td><td>IT 00 00</td>

<td>Viscosity (cPs) at 150 rpm</td><td>in &lt;φ in</td><td>Ή</td><td>IT or k0</td><td>in L0</td><td>in or LO</td><td>NC CN OR IN</td><td>Viscosity (cPs) at 152.0 rpm</td><td>CN 'Φ in NC</td><td>LOD OR LO 'Φ</td><td>in or in</td><td>IT in</td><td>at 00 CN H</td><td>LO in in</td><td> 25</td><td>ñ</td><td>'Φ 'Φ in LO</td><td>NC OR IT 'Φ</td><td>in 'Φ in in</td><td>in or in</td><td>LO 'Φ 00 NC</td><td>NC rHLO in</td><td>00 CN CN in</td><td>00 00 in in</td><td>in 00</td><td>LO OR either</td>

<td>Viscosity (cPs) at 60 rpm____________</td><td>NC &lt;0 LO</td><td>LO LO CN</td><td>in IT</td><td>IT 'ΦP</td><td>IT</td><td>in &lt;0 in L0</td><td>Viscosity (cPs) at 58.98 rpm</td><td>00 00 in</td><td>'Φ IT CN in</td><td> &lt;0 2</td><td>at 00 ooo</td><td>IT EITHER H</td><td>IT in</td><td> 1354.48</td><td></td><td> 1351.32</td><td> |1256.71 |</td><td>00 00 00 LO LO</td><td>00 00 00 LO L0</td><td> 671.77</td><td>'Φ00 CN (N k©</td><td>IT 00k© k0</td><td>in k©</td><td>00 00 in</td><td>NC NC</td>

<td>Viscosity (cPs) at 10 rpm</td><td>NC in NC NC</td><td>k0 'Φ LO OR CN</td><td>in σί 00 &lt;0</td><td>or in NC or</td><td>'Φ 00CN in</td><td>LO CN m CN</td><td>Viscosity (cPs) at 10 rpm</td><td>'φ cn cn</td><td>00 'φ or 'Φ</td><td> £3</td><td>IT IS</td><td>IT IS</td><td>or NC</td><td>or NC in</td><td>NC ^Φ LO 'Φ LO</td><td>in in</td><td>00 or in or</td><td> ¡3505.92</td><td> ¡3269.38 |</td><td> ¡3970.56</td><td>in or 'φ 00 in</td><td>Δ*9Δτή</td><td>in 00 oo</td><td> ¡2289.41</td><td>a</td>

<td>spindle</td><td>rHCN 8 in</td><td>NC 8 in</td><td>8 CO</td><td>NC 8 in</td><td>rHCN 8 in</td><td>NC 8 in</td><td>spindle</td><td>00 8 in</td><td>00 3 in</td><td>00 8 in</td><td>00 8 in</td><td>00 3 cn</td><td>NC 'ΦO in</td><td>rHCN1'φUin</td><td>NC 8 in</td><td>(N 8 in</td><td>NC 1 3 in</td><td>00 8 in</td><td>00 8 in</td><td>00 1'φU in</td><td>CN 1 3 in</td><td>NC 8 in</td><td>T£-TOS</td><td>SC4-18</td><td>8T-WS|</td>

<td> 5</td><td>either in</td><td>IT in</td><td>IT</td><td> 00</td><td>either IT</td><td>NC</td><td> 5</td><td>IT in</td><td>either</td><td>either IT</td><td>either IT</td><td>EITHER</td><td>either in</td><td>IT in</td><td>either 'Φ</td><td>either IT</td><td>EITHER IT</td><td>IT in</td><td>either ^φ</td><td>either IT</td><td>EITHER</td><td>either IT</td><td>either 'φ</td><td>either 'φ</td><td>EITHER IT</td>

<td>CMG Charge</td><td>o\°CN</td><td>o\°CN</td><td>o\°CN</td><td>□\°CN</td><td>o\°CN</td><td>o\°CN</td><td>&lt;ΰ (ΰυ</td><td>H</td><td>o\o</td><td>or\°</td><td>H</td><td>H</td><td>o\P CN</td><td>o\P CN</td><td>&lt;A9 CN</td><td>o\°CN</td><td>&lt;AP CN</td><td>o\°CN</td><td>o\°CN</td><td>o\°CN</td><td>or\or CN</td><td>o\° (N</td><td>o\°CN</td><td>oV &gt; LO</td><td>o\o LO</td>

<td>CMG Sample</td><td> 0</td><td> 0</td><td> 2</td><td> 0</td><td> 0</td><td> 0</td><td>CMG Sample</td><td>H</td><td>M</td><td> 1—1</td><td> 1—|</td><td>H</td><td> 1—1</td><td> 1—1</td><td> 1—1</td><td> 1—1</td><td>H</td><td>Jo</td><td>JO</td><td></td><td> ^3</td><td>Jo</td><td>H</td><td>Jo</td><td>Jo</td>

IT

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

The results summarized in Table 7 for the CMG 1G sample indicate a reduction in viscosity at pH 3.5. The viscosity of CMG (1G) solutions at pH levels greater than 4.5 indicated no decrease in viscosity, with the exception that at pH 12 there was a slight decrease in viscosity.

The pH of each of the CMG solutions in the above procedure was adjusted after the preparation of each solution. To examine whether the order of acid addition to adjust pH had any impact on solution viscosity, deionized water was adjusted to pH 3 with citric acid. A 2 wt% CMG solution (1G, Table 2) was prepared with the deionized water/citric acid pH 3 and homogenized according to Example 16 to dissolve the polymer. The viscosity of this solution was measured as in Example 16 and is indicated in Table 8.

Table 8

CMG Solution Viscosity - Reverse Addition of Acid to Adjust pH

<td>CMG Sample</td><td>CMG Burden</td><td>pH</td><td>Viscosity (cPs) at 10 rpm</td><td>Viscosity (cPs) at 60 rpm</td><td>Goo (cps) to 150rpm</td><td>Goo (cps) to 250rpm</td>

<td>1G</td><td> 2%</td><td> 3</td><td> 9188.4</td><td> 1444.4</td><td> 665.1</td><td> 416.8</td>

The results summarized in Table 8 indicate that

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INSTITUTO MEXICANO DE LA PROPERDAD INDUSTRIAL when the pH of the water is adjusted before the CMG polymer dissolves, the viscosity is stable (i.e., the viscosity values ​​in Table 8 at each respective shear rate are greater than those listed in the top row of Table 7). This could be due to a buffering effect of the polymer.

Therefore, pH affects the viscosity of CMG solutions.

Example 21

Effect of sodium chloride on CMG viscosity

This example describes the effect of sodium chloride on the viscosity of CMG in solution.

A 2 wt% CMG solution (1G, Table 2) was prepared by adding 3 g CMG in 147 g deionized water as described in Example 16 with the homogenization method. Therefore, the prepared CMG solution was divided into three aliquots, each weighing 49.98 g, 49.84 g, and 45.63 g, respectively. Sodium chloride (0.025 g) was added into the 49.98 g CMG solution to prepare a 2 wt% CMG solution in 0.05 wt% sodium chloride. Sodium chloride (0.15 g) was added into the 49.84 g CMG solution to prepare a 2 wt% CMG solution in 0.3 wt% sodium chloride. Sodium chloride (0.47 g) was added in the 45.63 g of CMG solution to prepare a 2 wt% CMG solution in

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY sodium chloride 1% by weight. The viscosity levels of each of the solutions were measured as described in Example 16 and shown in Table 9.

To determine whether the order of sodium chloride addition had an effect on the final viscosity of the CMG solution, 1% sodium chloride solution was prepared by dissolving 0.5 g sodium chloride in 4 9.5 g water. deionized CMG (1 g) in 49 g of the 1% sodium chloride was added with the homogenization method described in Example 16. The viscosity of the solution was measured as described in Example 16 and is indicated as sample 1G- 1 in Table 9.

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<td></td><td>Goo</td><td>(cps) to</td><td>250rpm</td><td> 206</td><td> 261.2</td><td> 302</td><td> 221.2</td>

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<td></td><td>τι</td><td></td><td></td><td></td><td></td><td></td><td></td>

<td></td><td>H</td><td>(ΰ</td><td> £</td><td></td><td></td><td></td><td></td>

<td></td><td>ω</td><td></td><td>Ρ&lt;</td><td></td><td></td><td></td><td></td>

<td></td><td> 0</td><td></td><td>μι</td><td></td><td></td><td>ΙΌ</td><td></td>

<td></td><td>υ</td><td>ω</td><td></td><td></td><td> •</td><td> •</td><td> •</td>

<td></td><td>m</td><td>Λ</td><td>o</td><td>σι</td><td></td><td> &lt;0</td><td>ω</td>

<td></td><td>-H</td><td>υ</td><td>ιη</td><td></td><td>o</td><td>L0</td><td>σι</td>

<td></td><td> &gt;</td><td> —*</td><td>Rh</td><td>Ο]</td><td>m</td><td>C0</td><td> 04</td>

<td></td><td>You</td><td></td><td></td><td></td><td></td><td></td><td></td>

<td> 0</td><td>rt</td><td></td><td></td><td></td><td></td><td></td><td></td>

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<td>or</td><td>•Rh</td><td>rt</td><td></td><td></td><td></td><td></td><td></td>

<td></td><td>m</td><td></td><td> £</td><td></td><td></td><td></td><td></td>

<td></td><td> 0</td><td></td><td>Ρ*</td><td>σι</td><td></td><td> &lt;0</td><td> 04</td>

<td></td><td>or</td><td>ω</td><td>Í4</td><td> •</td><td> •</td><td> ♦</td><td> •</td>

<td>You</td><td>w</td><td>CU</td><td></td><td> &lt;0</td><td></td><td></td><td>σι</td>

<td></td><td>•Rh</td><td>υ</td><td>Ο</td><td>Rh</td><td> 00</td><td> &lt;0</td><td>C0</td>

<td>Ό</td><td> &gt;</td><td></td><td>&lt;ο</td><td>ΓΟ</td><td>'φ</td><td>ΙΌ</td><td>ΙΌ</td>

<td>(OR</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

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<td>Ώ</td><td>You</td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>Ή</td><td>-H</td><td>ίΰ</td><td></td><td></td><td></td><td></td><td></td>

<td> &gt;</td><td>ω</td><td></td><td> £</td><td></td><td></td><td>NC</td><td>σι</td>

<td></td><td> 0</td><td></td><td></td><td></td><td>σ»</td><td> ♦</td><td> •</td>

<td>(you</td><td>υ</td><td>ω</td><td>Μ</td><td></td><td> *</td><td> &lt;0</td><td>ΙΌ</td>

<td></td><td>Ώ</td><td></td><td></td><td>(β</td><td></td><td>ΓΟ</td><td>σι</td>

<td></td><td>Η</td><td>o</td><td>o</td><td></td><td>ΙΌ</td><td>NC</td><td>p**</td>

<td>you</td><td> &gt;</td><td> *—</td><td>dr</td><td>you</td><td>σι</td><td>Γ-1</td><td>γΗ</td>

<td>(D</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>0 •H</td><td>you '0 -Η EITHER</td><td>φΌ 0</td><td></td><td></td><td></td><td></td><td></td>

<td> 0</td><td>(ΰ</td><td>μι</td><td></td><td></td><td></td><td></td><td></td>

<td>ω</td><td>Μ</td><td>p</td><td></td><td></td><td></td><td></td><td></td>

<td></td><td>4J</td><td>Η</td><td></td><td></td><td></td><td></td><td></td>

<td>(D</td><td>ΰ</td><td> 0</td><td></td><td></td><td></td><td></td><td></td>

<td>τι</td><td>(ϋ</td><td></td><td> 0</td><td>ο\ο</td><td></td><td></td><td></td>

<td></td><td>υ</td><td>o</td><td></td><td>ΙΌ</td><td>□V·</td><td></td><td></td>

<td> 0</td><td>α</td><td></td><td>τί</td><td>Ο</td><td>C0</td><td></td><td></td>

<td>μι</td><td> 0</td><td> 0)</td><td> 0</td><td> •</td><td> •</td><td>ο\°</td><td>ο\ο</td>

<td> 2</td><td>υ</td><td>τι</td><td>ω</td><td>o</td><td>o</td><td>Rh</td><td> 1—1</td>

<td>μι</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td> 0</td><td>(β</td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>OR</td><td> ?</td><td></td><td> 0</td><td></td><td></td><td></td><td></td>

<td></td><td>(β</td><td> 0)</td><td>yes</td><td>oV»</td><td>ο&gt;Ρ</td><td>ο\°</td><td>ο\ο</td>

<td> 0</td><td>υ</td><td>Ό</td><td> □</td><td>ΟΙ</td><td>η</td><td> 04</td><td>ΟΙ</td>

<td>T)</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td></td><td></td><td></td><td>(ΰ</td><td></td><td></td><td></td><td></td>

<td> 0</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>(ΰjj</td><td></td><td></td><td>OR</td><td></td><td></td><td></td><td></td>

<td>Rev</td><td></td><td></td><td>ω</td><td></td><td></td><td></td><td></td>

<td>Xí ω</td><td></td><td> 0</td><td> 0</td><td></td><td></td><td></td><td> 1</td>

<td>nj 4-1</td><td></td><td>g</td><td> 2</td><td>o</td><td></td><td>o</td><td> 0</td>

<td>H.W.</td><td></td><td> 0</td><td>yes</td><td></td><td>Η</td><td></td><td>γΗ</td>

it

IT

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The results summarized in Table 9 indicate that neither the presence of sodium chloride nor the method of adding it to the CMG solution has a significant impact on the viscosity of the CMG in solution.

Example 22

Effect of sodium sulfate on CMG viscosity

This example describes the effect of sodium sulfate on the viscosity of CMG in solution.

A 2 wt% CMG solution (1G, Table 2) was prepared as described in Example 16 with the homogenization method. This solution was then divided into three portions, each weighing 30.00 g, 29.69 g, and 29.92 g, respectively. Sodium sulfate (0.014 g) was dissolved in the 30.00 g CMG solution to prepare a 2 wt% CMG solution in 0.047 wt% sodium sulfate. Sodium sulfate (0.088 g) was dissolved in the 29.69 g of CMG solution to prepare a 2 wt% CMG solution in 0.3 wt% sodium sulfate. Sodium sulfate (0.29 g) was dissolved in the 29.92 g of CMG solution to prepare a 2 wt% CMG solution in 0.96 wt% sodium sulfate. The viscosity levels of each of the solutions were measured as described in Example 16 and shown in Table 10.

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<td></td><td>Goo</td><td>(cps) to</td><td>250rpm</td><td> 230.8</td><td> 237.6</td><td> 246.4</td>

<td></td><td>Ό</td><td></td><td></td><td></td><td></td><td></td>

<td></td><td>dr</td><td></td><td></td><td></td><td></td><td></td>

<td></td><td>You</td><td></td><td></td><td></td><td></td><td></td>

<td></td><td>H</td><td>dr</td><td> £</td><td></td><td></td><td></td>

<td></td><td>ω</td><td></td><td>CU</td><td></td><td></td><td>NC</td>

<td></td><td> 0</td><td></td><td>Cl</td><td>IT</td><td> 00</td><td>IT</td>

<td></td><td>υ</td><td>ω</td><td></td><td> •</td><td> •</td><td> ♦</td>

<td></td><td>ω</td><td>cu</td><td>either</td><td>either</td><td>either</td><td>f4</td>

<td></td><td>-Η</td><td>υ</td><td>IT</td><td>σλ</td><td>fH</td><td>CO</td>

<td></td><td> &gt;</td><td> *</td><td>Rh</td><td>NC</td><td>n</td><td>CO</td>

<td></td><td>τί</td><td></td><td></td><td></td><td></td><td></td>

<td></td><td>dr</td><td></td><td></td><td></td><td></td><td></td>

<td></td><td>τι</td><td></td><td></td><td></td><td></td><td></td>

<td></td><td>•Η</td><td></td><td></td><td></td><td></td><td></td>

<td> 0</td><td>ω</td><td></td><td> £</td><td></td><td></td><td></td>

<td>yes</td><td> 0</td><td>,*«—S.</td><td>CU</td><td>co</td><td>NC</td><td>NC</td>

<td>either</td><td>υ</td><td>ω</td><td>Cl</td><td> »</td><td> •</td><td> •</td>

<td></td><td>ω</td><td>cu</td><td></td><td>σ&gt;</td><td>either</td><td></td>

<td></td><td>•Η</td><td>υ</td><td>EITHER</td><td>IT</td><td></td><td></td>

<td>Φ</td><td> &gt;</td><td></td><td>IT</td><td>IT</td><td>IT</td><td></td>

<td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>Π</td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>(d you</td><td>τί (d</td><td></td><td></td><td></td><td></td><td></td>

<td>•H</td><td>Ό</td><td></td><td></td><td></td><td></td><td></td>

<td>ω</td><td>•Η</td><td>dr</td><td></td><td></td><td></td><td></td>

<td> 0</td><td>ω</td><td></td><td> £</td><td></td><td> [—</td><td>NC</td>

<td>υ</td><td> 0</td><td></td><td>CU</td><td> •</td><td> •</td><td> »</td>

<td>ω</td><td>υ</td><td>ω</td><td>Ci</td><td>NC</td><td>EITHER</td><td>IT</td>

<td>Ή</td><td>ω</td><td>cu</td><td></td><td>IFC</td><td></td><td></td>

<td> &gt;</td><td>Ή</td><td>υ</td><td>either</td><td>NC</td><td>IT</td><td>NC</td>

<td></td><td> &gt;</td><td></td><td> 1—1</td><td>Rh</td><td></td><td>IT</td>

<td>Η £</td><td>C</td><td> 0)</td><td></td><td></td><td></td><td></td>

<td> 0)</td><td> '0</td><td>Ό</td><td></td><td></td><td></td><td></td>

<td></td><td>Ή</td><td></td><td></td><td></td><td></td><td></td>

<td> 0</td><td>Ο</td><td> 0</td><td></td><td></td><td></td><td></td>

<td></td><td>dr</td><td>4J</td><td></td><td></td><td></td><td></td>

<td></td><td>Cl</td><td>dr</td><td></td><td></td><td></td><td></td>

<td>0ω</td><td>-U α 0)</td><td>UI 3</td><td> 0</td><td>o\o</td><td></td><td></td>

<td>φ</td><td>υ</td><td>ω</td><td>-H</td><td>IT</td><td>either\"</td><td></td>

<td>τΐ</td><td>α</td><td></td><td>You</td><td>EITHER</td><td>CO</td><td></td>

<td></td><td> 0</td><td>ω</td><td> 0</td><td> •</td><td> •</td><td>or\°</td>

<td> 0</td><td>o</td><td>τί</td><td>ω</td><td>either</td><td>either</td><td>H</td>

<td> 4-)</td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>dr U-4</td><td></td><td></td><td>(you y'all</td><td></td><td></td><td></td>

<td></td><td></td><td> 0</td><td></td><td></td><td></td><td></td>

<td>.-4 rn</td><td></td><td>yes</td><td></td><td>o\o</td><td>or\°</td><td>or\°</td>

<td>UJ</td><td></td><td>υ</td><td>or</td><td>NC</td><td>NC</td><td>NC</td>

<td>ω</td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>or you</td><td></td><td></td><td>dr</td><td></td><td></td><td></td>

<td></td><td></td><td></td><td>C4</td><td></td><td></td><td></td>

<td> 0</td><td></td><td></td><td>4J</td><td></td><td></td><td></td>

<td>rd -U</td><td></td><td></td><td>ω</td><td></td><td></td><td></td>

<td>rHU</td><td></td><td> 0</td><td> 0)</td><td></td><td></td><td></td>

<td>Λω</td><td></td><td>yes</td><td> 3</td><td> 0</td><td> 0</td><td></td>

<td>dr</td><td></td><td>υ</td><td> 8</td><td> | |</td><td>dr</td><td>H</td>

<td></td><td></td><td></td><td></td><td></td><td></td><td></td>

IT

LO H

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The results summarized in Table 10 indicate that the presence of sodium sulfate did not have a significant impact on the viscosity of the CMG in solution.

Example 23

Effect of sucrose on CMG viscosity

This example describes the effect of sucrose on the viscosity of CMG in solution.

A 2 wt% CMG solution (1G, Table 2) was prepared as described in Example 16 with the homogenization method. This solution was divided into two portions, each weighing 45 g and 20 g, respectively. To prepare a 10 wt% sucrose in CMG solution, 5 g of sucrose was dissolved in 45 g of the CMG solution. For a 60% by weight solution of sucrose in CMG, 30 g of sucrose was dissolved in 20 g of the CMG solution by manual mixing. The viscosity levels of each of the solutions were measured as described in Example 16 and shown in Table 11.

Table 11

Effect of sucrose on CMG viscosity

<td>CMG Sample</td><td>CMG Burden</td><td>Saccharose Conc.</td><td>Viscosity (cPs) at 10 rpm</td><td>Viscosity (cPs) at 60 rpm</td><td>Viscosity (cPs) at 150 rpm</td><td>Goo (cps) at 250rpm</td>

<td>1G</td><td> 2%</td><td> 10%</td><td> 7151.7</td><td> 1067.5</td><td> 430.7</td><td> 322.8</td>

<td>1G</td><td> 2%</td><td> 60%</td><td> 4278</td><td>N/A</td><td>N/A</td><td>N/A</td>

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The results summarized in Table 11 indicate that the presence of 10% sucrose has no impact on the viscosity of the CMG. However, a higher amount of sucrose (60%) reduced the viscosity.

Example 24

Preparation of potassium/sodium carboxymethyl poly-alpha-1,3-glucan

This example describes the production of the glucan ether derivative, potassium/sodium carboxymethyl poly-alpha-1,3-glucan.

10 g of poly-alpha-1,3-glucan (M_w = 168,000) to 200 ml of isopropanol in a distillation flask with 500 ml capacity fitted with a thermocouple to monitor temperature and a condenser connected to a recirculating bath and a magnetic stir bar. 40 mL of potassium hydroxide (15% solution) was added dropwise into this preparation, which was then heated to 25°C on a hot plate. The preparation was stirred for 1 hour before the temperature was increased to 55°C. Sodium chloroacetate (12g) was then added to produce a reaction, which was held at 55°C for 3 hours before being neutralized with 90% acetic acid. The solid thus formed was collected by vacuum filtration and washed with ethanol (70%) four times, vacuum dried at 20-25°C and analyzed by NMR and SEC for molecular weight and molecular weight.

<img file="MX373205B_D0184.tif" />

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MEXICAN INSTITUTE

OF THE PROPERTY

INDUSTRIAL the DoS. The solid material obtained was identified as water-soluble potassium/sodium carboxymethyl polyalpha-1,3-glucan with a DoS of 0.77.

Therefore, the glucan ether derivative, potassium/sodium carboxymethyl poly-alpha-1,3-glucan, was prepared and isolated.

The procedure of this example could be adapted to produce potassium carboxymethyl poly-alpha-1,3-glucan by the simple use of chloroacetic acid, rather than sodium chloroacetate, as the etherifying agent. Example 25 Effect of Shear Rate on Viscosity of Potassium/Sodium CMG

This example describes the effect of shear rate on the viscosity of potassium/sodium CMG (KNaCMG) in solution. KNaCMG in solution is shown to exhibit significant shear thinning behavior. Therefore, the addition of KNaCMG to a liquid can modify the rheological behavior of the liquid.

A sample of KNaCMG was prepared as described in Example 24. To prepare a 2 wt% KNaCMG solution, 1 g KNaCMG in 49 g deionized water was added. This preparation was then homogenized for 12-15 seconds at 20,000 rpm to dissolve the KNaCMG.

To determine the viscosity of the KNaCMG solution at

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY various shear rates, KNaCMG samples were exposed at various shear rates with a Brookfield III+ rheometer equipped with a recirculating bath to control temperature (20°C) and a YULA15-E(Z) spindle. . Shear rate was increased with a gradient program that increased from 0.01-250 rpm and shear rate increased by 7.36 (1/s) every 20 seconds. The results of this experiment are listed in Table 12. Table 12

Viscosity of the KNaCMG solution at various shear rates

<td>Load of KNaCMG</td><td>Goo (cps) to 22.07rpm</td><td>Goo (cPs) at 80.89rpm</td><td>Goo (cps) to 161.8rpm</td><td>Goo (cps) to 250rpm</td>

<td> 2%</td><td> 108.52</td><td> 82.06</td><td> 69.47</td><td> 62.12</td>

The results summarized in Table 12 indicate that the viscosity of the KNaCMG solution decreases as the shear rate increases. This observation means that the KNaCMG solutions demonstrate significant shear thinning behavior.

Therefore, when KNaCMG dissolves in aqueous solution, it not only modifies the viscosity of the solution, but also the rheological properties of the solution. Therefore, KNaCMG can be added to an aqueous liquid to

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY modify its rheological profile.

The procedure in this example could easily be adapted to use potassium carboxymethyl poly-alpha-1,3-glucan (KCMG) instead of KNaCMG.

Example 26

Preparation of lithium/sodium carboxymethyl poly-alpha-1,3-glucan

This example describes the production of the glucan ether derivative, lithium/sodium carboxymethyl poly-alpha-1,3-glucan.

10 g of poly-alpha-1,3-glucan (M_w = 168,000) to 200 ml of isopropanol in a distillation flask with 500 ml capacity fitted with a thermocouple to monitor temperature and a condenser connected to a recirculating bath and a magnetic stir bar. 50 mL of lithium hydroxide (11.3% solution) was added dropwise into this preparation, which was then heated to 25°C on a hot plate. The preparation was stirred for 1 hour before the temperature was increased to 55°C. Sodium chloroacetate (12g) was then added to produce a reaction, which was held at 55°C for 3 hours before being neutralized with 90% acetic acid. The solid thus formed was collected by vacuum filtration and washed with ethanol (70%) four times, vacuum dried at 20-25°C and analyzed by NMR and SEC for molecular weight and molecular weight.

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY the DoS. The solid material obtained was identified as CMG soluble in water with a DoS of 0.79.

Reagent amounts were adjusted to prepare another CMG sample, which had a DoS of 0.36. The CMG samples prepared in this example are listed in Table 13. Table 13 Synthesis of lithium/sodium CMG

<td>Sample Designation</td><td>Two</td>

<td>2A (127)</td><td> 0.79</td>

<td>2B (130)</td><td> 0.36</td>

Therefore, the glucan ether derivative, lithium/sodium carboxymethyl poly-alpha-1,3-glucan, was prepared and isolated.

The procedure of this example could be adapted to produce lithium carboxymethyl poly-alpha-1,3-glucan by the simple use of chloroacetic acid, rather than sodium chloroacetate, as the etherifying agent. Example 27 Effect of Shear Rate on Viscosity of Lithium/Sodium CMG

This example describes the effect of shear rate on the viscosity of lithium/sodium CMG (LiNaCMG) in the

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY solution. LiNaCMG in solution is shown to exhibit significant pseudoplastic behavior. Therefore, the addition of LiNaCMG to a liquid can modify the rheological behavior of the liquid.

To prepare a 2 wt% solution of LiNaCMG, 1 g of LiNaCMG (2A, Table 13) in 49 g of deionized water was added. This preparation was then homogenized for 12-15 seconds at 20,000 rpm to dissolve the LiNaCMG.

To determine the LiNaCMG solution viscosity at various shear rates, LiNaCMG samples were exposed at various shear rates with a Brookfield III+ rheometer equipped with a recirculating bath for temperature control (20°C) and a YULA15- spindle. E(Z). Shear rate was increased with a gradient program that increased from 0.01-250 rpm and shear rate increased by 7.36 (1/s) every 20 seconds. The results of this experiment are listed in Table 14. Table 14 Viscosity of LiNaCMG solution at various shear rates

<td>LiNaCMG Sample</td><td>LiNaCMG Burden</td><td>Viscosity (cPs) at 44.13 rpm</td><td>Viscosity (cPs) at 80.89 rpm</td><td>Viscosity (cPs) at 161.8 rpm</td><td>Goo (cps) to 250rpm</td>

<td>2A</td><td> 2%</td><td> 37.6</td><td> 35.22</td><td> 31.83</td><td> 29.62</td>

The results summarized in Table 14 indicate that the

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY The viscosity of the LiNaCMG solution decreases as the shear rate increases. This observation means that LiNaCMG solutions demonstrate significant shear thinning behavior.

Therefore, when LiNaCMG dissolves in aqueous solution, it not only modifies the viscosity of the solution, but also the rheological properties of the solution. Therefore, LiNaCMG can be added to an aqueous liquid to modify its rheological profile.

The procedure in this example could easily be adapted to use lithium carboxymethyl poly-alpha-1,3-glucan (LiCMG) instead of LiNaCMG.

Example 28

Preparation of poly-methyl alpha-1,3-glucan

This example describes the production of the glucan ether derivative, poly-methyl alpha-1,3-glucan (MG). This example is in addition to Examples 5 and 6 which describe the production of MG.

Sample 1

10 g of poly-alpha-1,3-glucan (M_w = 168584) in 40 mL isopropanol and 40 mL 30 wt% sodium hydroxide in a 400 mL beaker with a magnetic stir bar. The beaker was stirred on a magnetic stirrer at 375 rpm for one hour. The solid from this preparation was then collected by filtration to

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY was emptied, mixed with 150 ml of isopropanol and placed in a 200 ml capacity bottle with a lid. This preparation was left to stand overnight before being transferred to a 250 ml shaker tube reactor. The reactor was heated to 70°C and charged with 10 g of methyl chloride. The reaction was held at temperature for 17 hours, then charged with an additional 20 g of methyl chloride and held at temperature for 17 hours. After cooling, the reaction was quenched with 90% acetic acid. The solid from this reaction was collected by vacuum filtration, washed with methanol three times, dried in vacuo at 20-25°C and analyzed by NMR for DoS. The solid material obtained was identified as MG with a DoS of 1.75.

Then, 8 g of this MG was mixed with 50 ml of isopropanol and 32 ml of 30% by weight sodium hydroxide in a 400 ml beaker with a magnetic stir bar. The beaker was stirred on a magnetic stirrer at 375 rpm for one hour. The solid was then collected by vacuum filtration, mixed with 150 ml of isopropanol, and placed in a 200 ml bottle with a lid. This preparation was left to stand overnight before being transferred to a 250 ml shaker tube reactor. The reactor was heated to 70°C and charged with 12 g of methyl chloride. After cooling, the reaction

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY was neutralized with 90% acetic acid. The solid was collected by vacuum filtration and washed with methanol:acetone (60:40) five times, dried in vacuo at 2025°C and analyzed by NMR for DoS. The solid material obtained was identified as MG with a DoS of 1.8. This MG was indicated as Sample 1.

sample 2

20 g of poly-alpha-1,3-glucan (M_w = 245,000) in 50 mL of isopropanol and 80 mL of 30 wt% sodium hydroxide in a 400 mL beaker with a magnetic stir bar. The beaker was stirred on a magnetic stirrer at 375 rpm for one hour. Then, the solid of this preparation was collected by vacuum filtration, mixed with 150 ml of isopropanol, and placed in a 200 ml bottle with a lid. This preparation was left to stand overnight before being transferred to a 250 ml shaker tube reactor. The reactor was heated to 70°C and charged with 30 g of methyl chloride. The reaction was kept at temperature for 17 hours. After cooling, the reaction was quenched with 90% acetic acid. The solid from this reaction was collected by vacuum filtration, washed with methanol:acetone (60:40) five times, dried in vacuo at 20-25°C and analyzed by NMR for DoS. The solid material obtained was identified as MG with a DoS of 1.39.

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Then, 10 g of this MG was mixed with 50 ml of isopropanol and 40 ml of 30 wt% sodium hydroxide solution in a 400 ml beaker with a magnetic stir bar. The beaker was stirred on a magnetic stirrer at 375 rpm for one hour. Then, the solid of this preparation was collected by vacuum filtration, mixed with 100 ml of isopropanol, and placed in a 200 ml bottle with a lid. This preparation was left to stand overnight before being transferred to a 250 ml shaker tube reactor. The reactor was heated to 70°C and charged with 15 g of methyl chloride. After cooling, the reaction was quenched with 90% acetic acid. The solid was collected by vacuum filtration and washed with methanol:acetone (60:40) five times, dried in vacuo at 20-25°C and analyzed by NMR for DoS. The solid material obtained was identified as MG. This MG was indicated as Sample 2.

Therefore, additional samples of the glucan ether derivative, poly-methyl alpha-1,3-glucan, were prepared and isolated.

Example 29

Effect of shear rate on the viscosity of methyl polyalpha-1, 3-glucan

This example describes the effect of the speed of

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY cut in the viscosity of MG. It is shown that the MG exhibits pseudoplastic behavior. Therefore, the addition of MG to a liquid can modify the rheological behavior of the liquid.

To prepare a 2 wt% solution of MG, 1 g of Sample 1 or 2 prepared in Example 28 in 49 g of deionized water was added. Afterwards, each preparation was homogenized for 15-30 seconds at 20,000 rpm to dissolve the MG.

To determine the viscosity of each MG solution at various shear rates, the MG samples were exposed at shear rates of 10-250 rpm with a Brookfield DV III+ rheometer equipped with a recirculating bath to control temperature (20°C). and a Thermosel® SC4-21 spindle or ULA (Ultra Low Adapter) spindle and adapter assembly. The cutting speed was increased with a gradient program that increased from 10-250 rpm. Cutting speed increased by 7.35 (1/s) every 20 seconds for the ULA spindle and adapter and by 4.9 (1/s) every 20 seconds for the SC4-21 spindle. The results of this experiment are listed in Table 15.

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Table 15

Viscosity of MG solutions at various rates of

MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY court

<td>MG Sample (Example 28)</td><td>MG Burden</td><td>spindle</td><td>Viscosity (cPs) at 14.72 rpm</td><td>Viscosity (cPs) at 66.18 rpm</td><td>Viscosity (cPs) at 154.4 rpm</td><td>Viscosity (cPs) at 250 rpm</td>

<td> 1</td><td> 2%</td><td>ULA</td><td>N/A</td><td> 24.84</td><td> 23.42</td><td> 22.67</td>

<td> 2</td><td> 2%</td><td>ULA</td><td> 254.17</td><td> 228.97</td><td>N/A</td><td>N/A</td>

<td> 2</td><td> 1%</td><td>ULA</td><td>N/A</td><td> 24.36</td><td> 25.5</td><td> 25.92</td>

<td>MG Sample (Example 28)</td><td>MG Burden</td><td>spindle</td><td>Viscosity (cPs) at 14.9 rpm</td><td>Viscosity (cPs) at 63.88 rpm</td><td>Viscosity (cPs) at 152.0 rpm</td><td>Viscosity (cPs) at 232.5 rpm</td>

<td> 2</td><td> 2%</td><td>SC4-21</td><td> 193.49</td><td> 257.69</td><td> 226.38</td><td> 208.0</td>

The results summarized in Table 15 indicate that the viscosity of the MG solutions decreases as the shear rate increases. This observation means that the MG solutions demonstrate pseudoplastic behavior.

Therefore, when MG dissolves in aqueous solution, it not only modifies the solution's viscosity, but also the rheological properties of the solution. Therefore, the MG can be added to an aqueous liquid to modify its rheological profile. Example 30 Preparation of ethyl poly-alpha-1,3-glucan

This example describes the production of the glucan ether derivative, poly-ethyl alpha-1,3-glucan (EG).

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This example is in addition to Example 3, which describes a method of producing EG.

20 g of poly-alpha-1,3-glucan (M_w245,000) in 200 mL isopropanol and 109 mL of 15 wt% sodium hydroxide in a 400 mL beaker with a magnetic stir bar. The beaker was stirred on a magnetic stirrer at 375 rpm for one hour. Then, the solid of this preparation was collected by vacuum filtration, mixed with 100 ml of acetone, and placed in a 200 ml bottle with a lid. This preparation was left to stand overnight before being transferred to a 250 ml shaker tube reactor. The reactor was heated to 90°C and charged with 85 g of ethyl chloride. The reaction was kept at temperature for 17 hours. After cooling, the reaction was quenched with 90% acetic acid. The solid was collected by vacuum filtration, washed with 80% acetone five times, dried in vacuo at 20-25°C and analyzed by NMR for DoS. The solid material obtained was identified as EG with a DoS of 1.03.

Therefore, the glucan ether derivative, poly-alpha-1,3-glucan ethyl, was prepared and isolated.

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Example 31

Effect of shear rate on the viscosity of ethyl polyalpha-1, 3-glucan

This example describes the effect of shear rate on EG viscosity. EG is shown to exhibit pseudoplastic behavior. Therefore, the addition of EG to a liquid can modify the rheological behavior of the liquid.

To prepare a 2 wt% solution of EG, 1 g of EG as prepared in Example 3 0 was added to 49 g of deionized water. This preparation was then homogenized for 15-30 seconds at 20,000 rpm to dissolve the EG. In addition, a 1% by weight EG solution was prepared.

To determine the viscosity of EG solutions at various shear rates, EG solutions were exposed at various shear rates with a Brookfield DV III+ rheometer equipped with a recirculating temperature control bath (20°C) and an SC4 spindle. -21 Thermosel® or ULA spindle and adapter assembly. Shear rate was increased with a gradient program that increased from 10-250 rpm. Cutting speed increased by 7.35 (1/s) every 20 seconds for the ULA adapter and spindle and by 4.9 (1/s) every 20 seconds for the SC4-21 spindle. The results of this experiment are listed in Table 16.

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Table 16

Viscosity of EG solutions at various rates of

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<td>EG Burden</td><td>spindle</td><td>Viscosity (cPs) at 14.72 rpm</td><td>Viscosity (cPs) at 66.18 rpm</td><td>Viscosity (cPs) at 154.4 rpm</td><td>Goo (cps) to 250rpm</td>

<td> 2%</td><td>ULA</td><td> 146.76</td><td> 123.24</td><td>N/A</td><td>N/A</td>

<td> 1%</td><td>ULA</td><td> 12.76</td><td> 13.25</td><td> 12.27</td><td> 11.90</td>

<td>Burden</td><td>spindle</td><td>Viscosity (cPs) at 10 rpm</td><td>Goo (cps) to 83.47rpm</td><td>Viscosity (cPs) at 152.0 rpm</td><td>Viscosity (cPs) at 232.5 rpm</td>

<td> 2%</td><td>SC4-21</td><td>N/A</td><td> 112.53</td><td> 105.24</td><td> 98.8</td>

The results summarized in Table 16 indicate that the viscosity of the EG solutions decreases as the shear rate increases. This observation means that the EG solutions demonstrate pseudoplastic behavior.

Therefore, when EG dissolves in aqueous solution, it not only modifies the viscosity of the solution, but also the rheological properties of the solution. Therefore, EG can be added to an aqueous liquid to modify its rheological profile. Example 32 Preparation of poly-alpha-1,3-hydroxypropyl glucan

This example describes the production of the glucan ether derivative, poly-hydroxypropyl alpha-1,3-glucan (HPG).

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This example is in addition to Example 1, which describes a method of producing HPG.

10 g of poly-alpha-1,3-glucan (M_w = 168584) in 101 mL of toluene and 5 mL of 20% by weight sodium hydroxide in a 400 mL beaker with a magnetic stir bar. The beaker was stirred on a magnetic stirrer at 375 rpm for one hour at 55°C. This preparation was then placed in a 200 ml flask with a lid and allowed to settle overnight before being transferred to a 250 ml shaker tube reactor. The reactor was heated to 75°C and 34 g of 1,2-propylene oxide was added. The reaction was kept at temperature for 4 hours. After cooling, the reaction was quenched with 90% acetic acid. The solid was collected by vacuum filtration, washed with hot water three times, dried in vacuo at 20-25°C and analyzed by NMR for DoS. The solid material was determined to be HPG.

Therefore, samples of the glucan ether derivative, poly-alpha-1,3-hydroxypropyl glucan, were prepared and isolated.

Example 33

Effect of shear rate on the viscosity of polyalpha-1, 3-hydroxypropyl glucan

This example describes the effect of shear rate on HPG viscosity. HPG is shown to exhibit a

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY pseudoplastic behavior. Therefore, the addition of HPG to a liquid can modify the rheological behavior of the liquid.

To prepare a 2% by weight solution of HPG, 1 g of HPG as prepared in Example 32 was added to 49 g of deionized water. This preparation was then homogenized for 15-30 seconds at 20,000 rpm to dissolve the HPG.

To determine HPG solution viscosity at various shear rates, the sample was exposed at various shear rates with a Brookfield DV III+ rheometer equipped with a recirculating bath for temperature control (20°C) and a ULA spindle assembly. and adapter. The shear rate was increased with a gradient program that increased from 10-250 rpm and the shear rate increased by 7.3 5 (1/s) every 20 seconds for the ULA spindle and adapter. The results of the experiment are listed in Table 17. Table 17

Viscosity of HPG solutions at various shear rates

<td>HPG Burden</td><td>spindle</td><td>Goo (cps) to 14.72rpm</td><td>Viscosity (cPs) at 66.18 rpm</td><td>Goo (cps) to 154.4rpm</td><td>Goo (cps) to 250rpm</td>

<td> 2%</td><td>ULA</td><td> 45.73</td><td> 35.01</td><td> 26.36</td><td> 20.54</td>

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The results summarized in Table 17 indicate that the viscosity of the HPG solution decreases as the shear rate increases. This observation means that HPG solutions demonstrate pseudoplastic behavior.

Therefore, when HPG dissolves in aqueous solution, it not only modifies the viscosity of the solution, but also the rheological properties of the solution. Therefore, HPG can be added to an aqueous liquid to modify its rheological profile.

Example 34

Preparation of a dihydroxyalkyl poly-alpha-1,3-glucan

This example describes the production of a dihydroxyalkyl poly-alpha-1,3-glucan ether derivative. Specifically, dihydroxypropyl poly-alpha-1,3-glucan was produced.

10 g of poly-alpha-1,3-glucan (M_w = 138.438) in 100 mL of 20% tetraethylammonium hydroxide in a 500 mL distillation flask fitted with a thermocouple to monitor temperature and a condenser connected to a recirculating bath and a magnetic stir bar (which produced poly- alpha-1,3-glucan at -9.1% by weight). This preparation was stirred and heated to 30°C on a hot plate. The preparation was stirred for 1 hour to dissolve the solid before the temperature was increased to 55°C. Then 3-chloro-l,2373205 was added

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY propanediol (6.7 g) and 11 g of deionized water to produce a reaction (containing 3-chloro-l,2-propanediol at ~5.2% by weight), which was maintained at 55°C for 1.5 hours later, 5.6 g of deionized water was added to the reaction. The reaction was held at 55°C for an additional 3 hours and 45 minutes before being neutralized with acetic acid. After neutralization, excess isopropanol was added to precipitate a solid. The solid thus formed was collected by vacuum filtration and washed with ethanol (95%) four times and dried under vacuum at 20-25°C. The solid material obtained was identified as dihydroxypropyl poly-alpha1,3-glucan which was not soluble in water and had a degree of substitution of 0.6.

The procedure described above was repeated with some modification and this time using a sample of the previously prepared dihydroxypropyl poly-alpha-1,3-glucan as the starting material. Briefly, 5 g of the glucan ether in 50 mL of 20% tetraethylammonium hydroxide was added. This preparation was stirred with a magnetic stir bar until the solid dissolved, then heated to 30°C for 1 hour on a hot plate. The preparation was then heated to 55°C and 3-chloro-1,2-propanediol (8 g) was added to cause a reaction. The reaction was then stirred for 2 hours, then neutralized with acetic acid. After

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After neutralization, an excess of isopropanol was added to precipitate a solid. The solid thus formed was collected by vacuum filtration and washed with ethanol (95%) four times and dried under vacuum at 20-25°C. The solid material obtained was identified as dihydroxypropyl poly-alpha1,3-glucan which was soluble in water and had a degree of substitution of 0.89.

Therefore, a water-soluble dihydroxyalkyl poly-alpha-1,3-glucan ether derivative was prepared and isolated. Example 35

Preparation of a dihydroxyalkyl poly-alpha-1,3-glucan

This example describes the production of dihydroxypropyl poly-alpha-1,3-glucan. This example is in addition to Example 34, which further describes the production of this glucan ether derivative.

10 g of poly-alpha-1,3-glucan (M_w = 138.438) in 143 g of 20% tetraethylammonium hydroxide in a 500 ml distillation flask fitted with a thermocouple to monitor temperature and a condenser connected to a recirculating bath and a magnetic stir bar (which produced poly- alpha-1,3-glucan at -6.5% by weight). This preparation was stirred and heated to 30°C on a hot plate. The preparation was stirred for 1 hour to dissolve the solid before the temperature was increased to 55°C. Then 3-chloro-l,2373205 was added

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INSTITUTO MEXICANO DE LA PROPERDAD INDUSTRIAL propanediol (16 g) to produce a reaction (containing 3-chloro-l,2-propanediol at ~9.5% by weight), which was kept at 55°C for 2 hours before neutralization with acetic acid. After neutralization, excess isopropanol was added to precipitate a solid. The solid thus formed was collected by vacuum filtration and washed with ethanol (95%) four times and dried under vacuum at 20-25°C. The solid material obtained was identified as dihydroxypropyl poly-alpha-1,3-glucan which was soluble in water and had a degree of substitution of 0.6.

Therefore, a water-soluble dihydroxyalkyl poly-alpha-1,3-glucan ether derivative was prepared and isolated. It is noted that although the dihydroxypropyl poly-alpha-1,3-glucan produced in this example had a degree of substitution of 0.6, it was soluble in water. This result is in contrast to the dihydroxypropyl poly-alpha-1,3-glucan produced in the first process described above in Example 34, which also had a degree of substitution of 0.6, but was insoluble in water. Example 36 Effect of Shear Rate on Viscosity of Dihydroxypropyl Polyalpha-1,3-Glucan

This example describes the effect of shear rate on the viscosity of dihydroxypropyl poly-alpha-1,3-glucan. This glucan ether is shown to exhibit

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY pseudoplastic behavior. Therefore, the addition of dihydroxypropyl poly-alpha-1,3-glucan to a liquid can modify the rheological behavior of the liquid.

Poly-alpha-1,3-dihydroxypropyl glucan samples were prepared as described in Examples 34 and 35. To prepare 2% by weight solutions of these samples, 1 g of any sample was added to 49 g of deionized water. . Each preparation was then homogenized for 12-15 seconds at 20,000 rpm to dissolve the glucan ether.

To determine the viscosity of each solution at various shear rates, each solution was exposed at various shear rates with a Brookfield DV III+ rheometer equipped with a recirculating bath to maintain a constant temperature of 20°C. Shear rate was increased with a gradient program that increased from 10-250 rpm and shear rate increased by 4.9 (1/s) every 20 seconds. The results of the experiment are listed in Table 18.

Table 18

Viscosity of dihydroxypropyl poly-alpha-1,3-glucan solutions at various shear rates

<td>Sample</td><td>Goo (cps) to 66.18rpm</td><td>Viscosity (cPs) at 102.9 rpm</td><td>Viscosity (cPs) at 183.8 rpm</td><td>Goo (cps) at 250rpm</td>

<td>Example 34</td><td> 26.02</td><td> 25.41</td><td> 24.02</td><td> 23.23</td>

<td>Example 35</td><td> 26.97</td><td> 25.71</td><td> 24.61</td><td> 24.11</td>

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The results summarized in Table 18 indicate that the viscosities of the dihydroxypropyl poly-alpha-1,3-glucan solutions decrease as the shear rate increases. This observation means that the glucan ether demonstrates pseudoplastic behavior.

Therefore, when dihydroxypropyl poly-alpha-1,3-glucan dissolves in aqueous solution, it not only modifies the viscosity of the solution, but also the rheological properties of the solution. Such poly-alpha1,3-glucan ether derivatives can therefore be added to an aqueous liquid to modify its rheological profile. Example 37 Effect of shear rate on viscosity of borate cross-linked dihydroxypropyl poly-alpha1,3-glucan

This example describes the effect of shear rate on the viscosity of dihydroxypropyl poly-alpha-1,3-glucan when crosslinked with borate. This composition is shown to exhibit dilatant behavior. Therefore, the addition of borate cross-linked dihydroxypropyl poly-alpha-1,3-glucan to a liquid can modify the rheological behavior of the liquid.

A sample of dihydroxypropyl poly-alpha-1,3-glucan was first prepared as described in Example 34. To prepare a 2% by weight solution of this sample, 1 g of the sample in 49 g of deionized water was added. . Afterwards, each

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY The preparation was homogenized for 12-15 seconds at 20,000 rpm to dissolve the glucan ether.

Then, 0.04 g of boric acid was dissolved in the 2% by weight solution of poly-alpha-1,3-dihydroxypropyl glucan prepared above, including an appropriate amount of added deionized water, after which the pH was adjusted. to 9 with 20% sodium hydroxide. This procedure produced a 0.2% by weight solution of borate cross-linked dihydroxypropyl poly-alpha-1,3-glucan.

To determine the viscosity of this 0.2 wt% solution at various shear rates, the solution was exposed to various shear rates with a Brookfield DV III+ rheometer equipped with a recirculating bath to maintain constant temperature at 20°C. Shear rate was increased with a gradient program that increased from 10-250 rpm and shear rate increased by 4.9 (1/s) every 20 seconds. The results of the experiment are listed in Table 19. Table 19

Viscosity of a solution of borate cross-linked dihydroxypropyl poly-alpha-1,3-glucan at various shear rates

<td>Goo</td><td>Goo</td><td>Goo</td><td>Goo</td>

<td>(cps) to</td><td>(cps) to</td><td>(cps) to</td><td>(cps) to</td>

<td>66.18rpm</td><td>102.9rpm</td><td>183.8rpm</td><td>250rpm</td>

<td> 285.35</td><td> 304.89</td><td> 407.07</td><td> 437.6</td>

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The results summarized in Table 19 indicate that the viscosity of the borate cross-linked dihydroxypropyl poly-alpha-1,3-glucan solution increases as the shear rate increases. This observation means that this borate-crosslinked glucan ether demonstrates dilatant behavior. This result is contrary to the results observed with the uncrosslinked dihydroxypropyl poly-alpha-1,3-glucan solutions (Example 36), which exhibited pseudoplastic behavior.

Therefore, when the borate-crosslinked dihydroxypropyl poly-alpha-1,3-glucan dihydroxypropyl is dissolved in aqueous solution, it not only modifies the viscosity of the solution, but also the rheological properties of the solution. Such cross-linked poly-alpha-1,3-glucan ether derivatives can therefore be added to an aqueous liquid to modify its rheological profile. Example 38 Creation of the calibration curve for toluidine blue dye 0 with UV absorption

This example describes the creation of a calibration curve useful for determining the relative level of adsorption of poly alpha-1,3-glucan ether derivatives on fabric surfaces.

Solutions of known concentration (in ppm) were prepared with toluidine blue O dye. The absorbance of these

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY solutions were measured with a LAMOTTE SMART2 colorimeter at 520 or 620 nm. Absorption data was plotted so that it could be used to determine the dye concentration of solutions that were exposed to fabric samples. The concentration and absorbance of each calibration curve are provided in Table 20.

Table 20

Toluidine O Blue Dye Calibration Curve Data

<td>Colorant Concentration (ppm)</td><td>Average Absorbance at 620 nm</td>

<td> 12.5</td><td> 1.41</td>

<td> 10</td><td> 1.226666667</td>

<td> 7</td><td> 0.88</td>

<td> 5</td><td> 0.676666667</td>

<td> 3</td><td> 0.44</td>

<td> 1</td><td> 0.166666667</td>

Therefore, a useful calibration curve was prepared for determining the relative level of adsorption of poly alpha-1,3-glucan ether derivatives on fabric surfaces. This calibration curve was used in Example 39. Example 39 Adsorption of poly-carboxymethyl alpha-1,3-glucan (CMG) on various fabrics

This example describes the tests for the degree of adsorption

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY of a poly-alpha-1,3-glucan ether compound (CMG) in different types of fabrics.

A 0.25 wt% CMG solution was prepared by dissolving 0.375 g of the polymer in 149.625 g of deionized water. This solution was divided into several aliquots with different concentrations of polymer and other components (Table 21). These other components were acid (dilute hydrochloric acid) or base (sodium hydroxide) to modify the pH, or NaCl salt.

Table 21

CMG solutions used in fabric adsorption studies

<td>Amount of NaCl (g)</td><td>Amount of solution (g)</td><td>Polymer concentration (% by weight)</td><td>Acid quantity (g)</td><td>Base amount (g)</td><td>final pH</td>

<td> 0</td><td> 15</td><td> 0.25</td><td>N/A</td><td>N/A</td><td> ~7</td>

<td> 0.15</td><td> 14.85</td><td> 0.2475</td><td>N/A</td><td>N/A</td><td> -7</td>

<td> 0.3</td><td> 14.7</td><td> 0.245</td><td>N/A</td><td>N/A</td><td> -7</td>

<td> 0.45</td><td> 14.55</td><td> 0.2425</td><td>N/A</td><td>N/A</td><td> ~7</td>

<td> 0</td><td> 9.8412</td><td> 0.2459</td><td> 0.1641</td><td>N/A</td><td> 3.52</td>

<td> 0</td><td> 9.4965</td><td> 0.2362</td><td> 0.553</td><td>N/A</td><td> 5.01</td>

<td> 0</td><td> 9.518</td><td> 0.2319</td><td>N/A</td><td> 0.752</td><td> 8.98</td>

<td> 0</td><td> 9.8811</td><td> 0.247</td><td>N/A</td><td> 0.1189</td><td> 10.93</td>

Four different types of fabrics (cretonne, polyester, 65:35 poly/cretonne, bleached cotton) were cut into 0.17 g pieces. Each piece was placed in a 2 ml well in a 48-well cell culture plate. each sample

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The fabric was exposed to 1 ml of each of the above solutions (Table 21) for a total of 36 samples (a control solution without polymer was included for each fabric test). The fabric samples were allowed to stand for at least 30 minutes in the polymer solutions. The fabric samples were removed from the polymer solutions and rinsed in deionized water for at least one minute to remove any unbound polymer. The fabric samples were then dried at 60°C for at least 30 minutes until constant dryness was achieved. The fabric samples were weighed after drying and individually placed in 2 ml wells in a 48-well cell culture plate. The fabric samples were then exposed to 1 mL of a 250 ppm solution of toluidine blue dye. The samples were left in the dye solution for at least 15 minutes. Each fabric sample was taken out of the dye solution, and then the dye solution was diluted 10x.

The absorbance of the diluted solutions was measured in comparison to a control sample. A relative measure of glycan polymer adsorbed on the fabric was calculated based on the calibration curve created in Example 38 for Toluidine Blue 0 dye. Specifically, the difference in UV absorbance for the fabric samples exposed to the polymer at comparison with controls (fabric

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY not exposed to polymer) represents a relative measure of the polymer adsorbed on the fabric. This difference in UV absorbance could be further expressed as the amount of dye bound to the fabric (over the amount of dye bound to the control), which was calculated from the calibration curve (i.e. UV absorbance was converted to ppm of dye). Table 22 provides colorant (ppm); a positive value represents the amount of dye that exceeded the amount of dye bound to the control fabric, while a negative value represents the amount of dye that was less than the amount of dye bound to the control fabric. A positive value reflects that the glucan ether compound was adsorbed on the surface of the fabric.

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<td rowspan="8">Table 22 Relative amount of CMG bound to different fabrics under different conditions</td><td rowspan="2">bleached cotton</td><td>_AND (uidd) squejoioo</td><td> + 9.28</td><td> +6.26</td><td> + 5.57</td><td> +7.62</td><td></td><td></td><td> +3.22</td><td> +10.17</td><td>Or r-1 +</td><td> +15.73</td><td rowspan="8">^a Amount of dye attached to the fabric. A positive value represents the amount of dye that exceeded the amount of dye bound to the control. A positive amount of dye, in turn, represents the relative amount of glucan ether adsorbed on the fabric. b The pH of the binding conditions was about 7 (refer to Table 21).^c Binding conditions did not include salt (refer to Table 21).</td>

<td>salt concentration</td><td>Λ OR</td><td>Λ H</td><td>x) or\°CM</td><td>Λ or\° m</td><td></td><td>oh wow</td><td> 3.5</td><td>in</td><td>Ch</td><td></td>

<td rowspan="2">Polyester/cretonne 65:35</td><td>colorant (ppm)^a</td><td>EITHER</td><td> + 0.49</td><td> + 1.76</td><td>IT +</td><td></td><td></td><td> -0.39</td><td> 1</td><td> -1.95</td><td> + 2.54</td>

<td>salt concentration</td><td>Λ OR</td><td>eleventh H</td><td>Λ or\or CM</td><td>ΧΪ or\© C0</td><td></td><td>wow</td><td> 3.5</td><td>IT</td><td>in</td><td></td>

<td rowspan="2">Polyester</td><td>colorant (ppm)^a</td><td>EITHER</td><td>00 id +</td><td> + 3.62</td><td> + 1.47</td><td></td><td></td><td> + 1.76</td><td> + 7.62</td><td> + 1.36</td><td>00 or +</td>

<td>salt concentration</td><td>Λ OR</td><td>Λ or\&lt;&gt;</td><td>XI o\° CM</td><td>Λo\°CO</td><td></td><td>or eft</td><td> 3.5</td><td>in</td><td>σι</td><td>dr</td>

<td rowspan="2">Cretonne</td><td>colorant (ppm)^a</td><td> 0.29</td><td> +2.25</td><td>or 1</td><td> + 1.37</td><td></td><td></td><td>EITHER 1</td><td> + 0.02</td><td>00 or +</td><td> +4.39</td>

<td>salt concentration</td><td>Λ OR</td><td>Λ o\o (—1</td><td>Λ or V&gt; CM</td><td>XI o\°CO</td><td></td><td>or X0&lt;</td><td> 3.5</td><td>IT</td><td>in</td><td>dr</td>

IT

EITHER

ID rH

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The data in Table 22 indicates that the CMG polymer can adsorb to various types of fabric under different pH and salt conditions. This adsorption occurs even when fabrics are rinsed after exposure to the polymer. It is highlighted that the glucan ether was able to adsorb on the polyester and the polyester/cretonne mixture, considering that the carboxymethylcellulose is not absorbed on or is only poorly absorbed on the polyester and mixtures of this with cotton (see the publication of the application for European Patent No. EP0035478, for example).

Therefore, a poly-alpha-1,3-glucan ether derivative in an aqueous composition can be adsorbed on the fabric.

Example 40

Preparation and viscosity analysis of poly-methyl alpha-1,3glucan

This example describes the production of the glucan ether derivative, poly-methyl alpha-1,3-glucan (MG), with one-pot and two-pot synthesis strategies. This example is in addition to Examples 5, 6 and 28 which describe the production of MG. This example further describes the viscosity analysis of MG.

One pot synthesis:

g (0.0617 mol) of poly-alpha-1,3-glucan (M_w

-160,000) and 25.55 g of 30% sodium hydroxide (total NaOH=

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7.665 g [0.192 mol]) were loaded into a shaker tube. Then 70 g (1.386 mol) of methyl chloride was added. This preparation was placed in a sealed pressure vessel, heated to 50°C and stirred for 10 hours. The solid content was then isolated. 40.7 g solids were placed in 150 ml water at 95°C, stirred for 30 seconds and filtered (filtrate was yellow). The solids were stirred again in 80-90°C water for 3 minutes; the pH of the solids was determined to be neutral. The final solid material was filtered and dried in a vacuum oven at 85°C to yield 7.6 g of a brownish solid. This material was analyzed by NMR, and it was determined that methyl poly-alpha-1,3-glucan was produced with a DoS of approximately 1.35.

Synthesis in two vessels:

A 250 mL 3-neck round bottom flask with magnetic stir bar was charged with 200 g of 30% sodium hydroxide and 10 g (0.0617 mol) of poly-alpha-1,3-glucan (M_w = -160,000). This preparation was stirred at room temperature for 60 minutes. The solid was then filtered and blown dry on the filter for 5 minutes to yield 35,547 g of off-white solids. The solids were then charged to a pressure vessel together with 100g of methyl chloride and the contents stirred at 50°C for 10 hours. The solids were collected and placed in 150 ml of water at 95°C, stirred for 30 seconds and

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY filtered (the filtrate was yellow). The solids were stirred again in 80-90°C water for 3 minutes; the pH of the solids was determined to be neutral. The final solid material was filtered and dried in a vacuum oven at 85°C to yield 7.3 g of an off-white solid. This material was analyzed by NMR, and it was determined that methyl poly-alpha-1,3-glucan was produced with a DoS of approximately 1.41.

Viscosity analysis:

The MG samples isolated from the one-pot and two-pot syntheses (above) were analyzed for viscosity at various shear rates largely following the procedures described in Example 29. The results of this experiment are listed in Table 23.

Table 23

Viscosity of MG solutions at various shear rates

<td>MG Sample</td><td>MG Burden</td><td>Viscosity (cPs) at 1 rpm</td><td>Viscosity (cPs) at 5 rpm</td><td>Viscosity (cPs) at 9 rpm</td><td>Viscosity (cPs) at 25 rpm</td>

<td> 1</td><td> 2%</td><td> 8777</td><td> 1874</td><td> 1180</td><td> 650</td>

<td> 2</td><td> 2</td><td> 6628</td><td> 2244</td><td> 1522</td><td> -</td>

The results summarized in Table 23 indicate that the viscosity of the MG solutions decreases as the shear rate increases. This observation means that the MG solutions demonstrate pseudoplastic behavior.

<img file="MX373205B_D0216.tif" />

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MEXICAN INSTITUTE OF INDUSTRIAL PROPERTY

Therefore, when MG dissolves in aqueous solution, it not only modifies the solution's viscosity, but also its rheological properties. of the solution. Therefore, the MG can be added to an aqueous liquid to modify its rheological profile.

It is stated that in relation to this date, the best method known by the applicant to carry out the aforementioned invention is the one that is clear from the present description of the invention.