Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents

"Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents"

FIELD OF THE INVENTION

The present invention relates to novel sulfoperoxycarboxylic acid compounds, compositions, and methods for manufacturing and using these compounds.

CONTEXT

Peroxycarboxylic acids are known for their use as antimicrobial and bleaching agents. However, conventional peroxycarboxylic acids have inherent disadvantages regarding limited storage stability and water solubility. Furthermore, most peroxycarboxylic acids have an unpleasant odor. Therefore, there is a need for peroxycarboxylic acid compositions and compounds with little or no odor, soluble in water, and with stable storage that also possess antimicrobial and bleaching properties.

SUMMARY

In some respects, the present invention relates to novel sulfoperoxycarboxylic acids and their methods of manufacture. The compounds of the invention are stable during storage, have little or no odor, and are soluble in water. Furthermore, the compounds of the present invention can be derived from renewable, non-petroleum-based oils.

In some respects, the present invention provides methods for using its compounds as bleaching and/or antimicrobial agents. In others, the present invention provides methods for using its compounds as coupling agents. The present invention also provides methods for using its compounds as low-foaming bleaching hydrotropes for tunnel washers and side-loading washing machines.

In some cases, the compounds and compositions of the present invention are suitable for use as bleaches at low temperatures, for example, around 40 degrees Celsius. In others, the compounds of the present invention are suitable for use as pH-optimized peroxygen bleaches in combination with alkaline detergents. The present invention also includes a method for using its compounds and compositions as bleaches for fabrics, such as wool and cotton, that protect colors and are tolerant to fabrics.

BRIEF DESCRIPTION OF THE FIGURES

Figure 1 is a graphical representation of the stability profile of peroxyoctanoic acid over time when in contact with different test solutions.

Figure 2 is a graphical representation of the stability of a model composition of the present invention over time at an elevated temperature.

Figure 3 is a graphical representation of the capabilities of selected compositions of the present invention for stabilizing percarboxylic acids over time.

Figure 4 is a graphical representation of the bleaching performance of the compositions of the present invention compared to bleaching agents available on the market.

Figure 5 is a graphical representation of the stability profile of peroxyoctanoic acid in combination with model compositions of the present invention.

Figure 6 is a graphical representation of the coupling capacity of a selected composition of the present invention.

DETAILED DESCRIPTION

The present invention relates to sulfoperoxycarboxylic acids of Formula I and to their methods of manufacture and use. Unlike conventional peroxycarboxylic acids, the sulfoperoxycarboxylic acids of the present invention have little odor, are water-soluble, and are stable in storage. The compounds of the present invention can be used as a pure solid powder, or mixed with other functional ingredients, for example, chelating agents, buffers, or other cleaning agents. They can also be incorporated into liquid formulas. The compounds and compositions of the present invention have many uses, including, but not limited to, antimicrobial, bleaching, and coupling agents.

To make the invention easier to understand, certain terms will first be defined.

As used herein, the terms “percentage by weight”, “% by weight”, “percentage by weight”, “% by weight” and their variations refer to the concentration of a substance as its weight is divided by the total weight of the composition and multiplied by 100. It is understood that, as used herein, the terms “percentage”, “%” and the like are synonymous with “percentage by weight”, “% by weight”, etc.

As used in this document, the term “about” refers to the variation that may occur in the numerical quantity, for example, through typical measurement and handling procedures of liquids used for the manufacture of concentrates or solutions for real-world use; through unintentional error in these procedures; through differences in the manufacture, source, or purity of the ingredients used to make the compositions or perform the methods; and so on. The term "about" also encompasses quantities that differ due to different equilibrium conditions for a resulting composition from a given initial mixture. Whether or not modified by the term "about," the statements include equivalent quantities.

It is necessary to observe that, as used in these specifications and in the attached statements, the singular forms “a”, “an” and “the” include their respective plural forms, unless the content clearly indicates otherwise. Thus, for example, reference to a composition containing “a compound” includes a composition with two or more compounds. It should also be noted that the term “or” is generally used in the sense of “and/or” unless the content clearly indicates otherwise.

As used here, the expressions “unpleasant odor,” “repulsive odor,” or “bad smell” refer to a pungent, acrid, strong odor or atmospheric environment from which an ordinary person would withdraw if able. The hedonic tone provides a measure of the degree to which the odor is pleasant or unpleasant. An “unpleasant odor,” “repulsive odor,” or “bad smell” has a hedonic evaluative tone as being “as unpleasant as” or “more unpleasant than” a 5% by weight solution of acetic acid, propionic acid, butyric acid, or mixtures thereof.

As used in this document, the term “microorganism” refers to any non-cellular or unicellular organism (including colonial). Microorganisms include all prokaryotes. These include bacteria (including cyanobacteria), spores, lichens, fungi, protozoa, virines, viroids, viruses, bacteriophages, and some algae. As used herein, the term “microbe” is synonymous with microorganism.

The term “food product,” as used herein, includes any food substance that may require treatment with an antimicrobial composition or agent and that is edible, with or without further preparation. Food products include meats (p. e.g., red meat and pork), seafood, poultry, agricultural products (e.g., fruits and vegetables), eggs, live eggs, egg products, ready-to-eat foods, wheat, seeds, roots, tubers, leaves, stems, cereals, flowers, sprouts, spices, or any combination thereof. The term "agricultural products" refers to food products, such as fruits, vegetables, and plant-derived materials, that are typically sold raw and often unpackaged, and which can sometimes be eaten raw.

As used herein, the term "vegetable" or "vegetable product" includes any substance made from plants or derived from plants. Vegetable products include, but are not limited to, seeds, nuts, pits, cut flowers, plants or crops grown or stored in greenhouses, houseplants, and so forth. Vegetable products include many animal feeds.

The term "meat product," as used in this document, refers to all types of animal meat, including carcass, muscle, fat, organs, skin, bones, body fluids, and similar components that make up the animal. Animal meat includes, but is not limited to, meat from mammals, birds, fish, reptiles, amphibians, snails, mollusks, crustaceans, other edible species such as lobster, crab, etc., or other types of seafood. Types of animal meat include, for example, the whole or part of animal meat, alone or in combination with other ingredients. Typical forms include, for example, processed meats such as cured meats, sectioned and formed products, minced products, diced products, ground meat and products that include it, whole products, and so on.

As used in this document, the term "poultry" refers to all forms of any bird kept, obtained, or domesticated for the purpose of obtaining meat or eggs, including chicken, turkey, ostrich, young chicken, pigeon, guinea fowl, pheasant, quail, duck, goose, emu, or similar birds and their eggs. The term "poultry" includes whole, cut, processed, cooked, or raw poultry, and encompasses all forms of poultry meat, its by-products, and secondary products. Poultry meat includes muscles, fat, organs, skin, bones, and body fluids and similar components that make up the animal. Types of animal meat include, for example, the whole or part of the animal meat, alone or in combination with other ingredients. The most common types include, for example, processed poultry meat such as cured meat, sectioned and formed products, minced products, diced products, and whole products.

As used herein, the expression "poultry remains" refers to debris, waste, materials, dirt, inedible parts, parts, remains, viscera, organs, fragments or combinations of these and similar materials removed from poultry carcasses or parts thereof during processing and which go into a sewer system.

As used herein, the term "food processing surface" refers to the surface of a tool, machine, equipment, structure, building, or similar item that is used as part of a food processing, preparation, or storage activity. Examples of food processing surfaces include the surface of food processing or preparation equipment (e.g., slicing, canning, or conveying equipment, including chutes), food processing utensils (e.g., utensils, dishes, washing equipment, and bar glasses), and also floors, walls, or structural devices where food processing occurs. Food processing surfaces are found and used in food anti-spoilage air circulation systems, aseptic packaging sanitization, refrigerator and food chiller cleaners and disinfectants, washing equipment sanitization, bleach cleaning and sanitization, food packaging materials, cutting board additives, third sink sanitization, beverage refrigerators and warmers. Cooling or boiling water for meats, automatic washer disinfectants, sanitizing gels, cooling towers, antimicrobial clothing sprays for food processing, and non-aqueous or low-water food preparation lubricants, oils, and rinsing additives.

As used herein, the terms “equipment” or “utensils” may refer to eating and cooking utensils, dishes, and other hard surfaces such as showers, sinks, toilets, bathtubs, countertops, windows, mirrors, transport vehicles, and floors.

As used in this document, the term "washing equipment" refers to utensils for washing, cleaning, or rinsing. Utensils also include articles made of plastic. The types of plastics that can be cleaned with the compositions according to the invention include, but are not limited to, those comprising polycarbonate (PC) polymers, acrylonitrile butadiene styrene (ABS) polymers, and polysulfone (PS) polymers. Another example of plastic that can be cleaned with the compounds and compositions of the invention includes polyethylene terephthalate (PET).

As used herein, the term "air currents" includes air circulation systems designed to prevent food spoilage. Air currents also include those typically found in hospitals, operating rooms, wards, maternity wards, morgues, and clinical diagnostic rooms.

As used herein, the term "waters" includes water used for food processing or transportation. Food processing or transport water includes water from transporting agricultural products (e.g., that found in chutes, pipeline transport, cutters, slicers, bleachers, retort systems, washers, and the like), belt sprays for food conveyor lines, boot and hand soaking containers, third sink rinse water, and so on. Water features also include domestic and recreational water sources such as swimming pools, spas, recreational slides, water slides, fountains, and similar features.

As used herein, the expression "healthcare service surface" refers to a surface of an instrument, device, cart, cage, furniture, structure, building, or similar item, used as part of a healthcare service activity. Examples of healthcare service surfaces include the surfaces of medical or dental instruments or devices, electronic equipment used in patient health monitoring, and floors, walls, or structural devices where healthcare services are provided. Healthcare service surfaces are found in hospitals, operating rooms, wards, maternity wards, morgues, and clinical diagnostic rooms. These surfaces can be classified as "hard surfaces" (such as walls, floors, urinals, etc.), or fabric surfaces, for example, mesh, woven and non-woven surfaces (such as surgical gowns, drapes, bedding, bandages, etc.), or patient care equipment (such as respirators, diagnostic equipment, shunts, probes, wheelchairs, beds, etc.), or surgical and diagnostic equipment. Healthcare service surfaces include items and surfaces used in animal healthcare.

As used herein, the term "instrument" refers to the various medical or dental instruments or devices that can benefit from cleaning with a composition according to the present invention.

The terms “medical instrument”, “dental instrument”, “medical device”, “dental device”, “medical equipment” or “dental equipment” used in this document refer to instruments, devices, tools, items, apparatus and equipment used in medicine or dentistry. These instruments, devices, and equipment can be cold-sterilized, rinsed or washed, and then heat-sterilized or otherwise cleaned with a composition of the present invention. These various instruments, devices, and equipment include, but are not limited to: Diagnostic instruments, trays, containers, holders, racks, forceps, scissors, blades, saws (e.g., bone saws and their blades), hemostats, knives, chisels, surgical forceps, files, tweezers, drills, drill points, rasps, dental drills, retractors, openers, elevators, clamps, needle holders, carriers, clips, hooks, gouges, curettes, retractors, straighteners, punctures, extractors, curettes, keratotomy, spatulas, expressers, trocars, Dilators, cages, glassware, tubes, catheters, cannulas, plugs, stents, probes (e.g., endoscopes, stethoscopes, and arthroscopes) and related and similar equipment, or combinations thereof.

As used herein, "agricultural" or "veterinary" objects or surfaces include animal feed, water supply stations and animal holding areas, animal housing, veterinary clinics (e.g., surgery or treatment areas), veterinary surgical areas, and so forth.

As used herein, the term “phosphorus-free” or “substantially phosphorus-free” refers to a composition, mixture, or ingredient that does not contain phosphorus or a compound containing phosphorus, or to which phosphorus or a phosphorus-containing compound has been added. If phosphorus or a phosphorus-containing compound is present due to contamination of a phosphorus-free composition, mixture, or ingredient, the amount of phosphorus must be less than 0.5% by weight. It is preferable that the amount of phosphorus be less than 0.1% of the weight, and even better if it is less than 0.01% of the weight.

For the purposes of this patent application, successful microbial reduction is achieved when microbial populations are reduced to at least about 50%, or significantly more than that achieved by washing with water. Greater reductions in the microbial population provide higher levels of protection.

As used herein, the term "disinfectant" refers to an agent that reduces the number of bacterial contaminants to safe levels, as determined by public health requirements. In certain cases, the disinfectants for use in this invention will provide a reduction of at least 99.999% (reduction on the order of 5 logs). These reductions can be evaluated using a procedure established in Germicidal and Detergent Sanitizing Action of Disinfectants, Official Methods of Analysis of the Association of Official Analytical Chemists, paragraph 960.09 and applicable sections, 15.^the edition, 1990 (EPA Guideline 91-2). According to this reference, a disinfectant must provide a 99.999% reduction (reduction on the order of 5 logs) within 30 seconds at room temperature, 25 ± 2 °C, against various test organisms.

As used in this document, the term “disinfectant” also refers to an agent that kills all vegetative cells, including the most well-known pathogenic microorganisms, using the procedure described in AOAC Use Dilution Methods, Official Methods of Analysis of the Association of Official Analytical Chemists, paragraph 955.14 and applicable sections, 15.^the edition, 1990 (EPA Guideline 91-2). According to this document, the term "high-level disinfection" or "high-level disinfectant" refers to a compound or composition that kills virtually all organisms except high levels of bacterial spores, and this is achieved with a chemical germicide released for commercialization as a sterilizing agent by the FDA (Food and Drug Administration). As used herein, the term "intermediate-level disinfection" or "intermediate-level disinfectant" refers to a compound or composition that kills mycobacteria, most viruses, and bacteria with a chemical germicide registered as a tuberculocide by the EPA (Environmental Protection Agency). As used in this document, the term "low-level disinfection" or "low-level disinfectant" refers to a compound or composition that kills some viruses and bacteria with a chemical germicide registered as a hospital disinfectant by the EPA.

As used in this invention, the term "sporicide" refers to a physical or chemical agent or process capable of causing a reduction greater than 90% (reduction on the order of 1 log) in the spore population of Bacillus cereus or Bacillus subtilis in 10 seconds at 60 °C. In certain cases, the sporicidal compositions of the invention provide a reduction greater than 99% (reduction on the order of 2 logs), greater than 99.99% (reduction on the order of 4 logs) or greater than 99.999% (reduction on the order of 5 logs) in this population within 10 seconds at 60 °C.

The differentiation between the "cidal" or "static" activity of antimicrobials, the definitions that describe the degree of efficacy, and the official laboratory protocols for measuring efficacy are considerations for understanding the relevance of antimicrobial agents and compositions. Antimicrobial compositions can cause two types of microbial cell damage. The first is a lethal and irreversible action, resulting in the complete destruction of microbial cells or their incapacitation. The second type of cellular damage is reversible, so that if the organism gets rid of the agent, it can multiply again. The first is called microbicidal and the second microbiostatic. A disinfectant is, by definition, an agent that provides antimicrobial or microbicidal activity. In contrast, a preservative is generally described as an inhibitory or microbiostatic composition.

As used in this document, the term “alkyl” or “alkyl groups” refers to saturated hydrocarbons with one or more carbon atoms, including straight-chain alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc.), cyclic alkyl groups (or cycloalkyl or alicyclic or carbocyclic groups) (e.g., cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.), branched-chain alkyl groups (e.g., e.g., isopropyl, tert-butyl, sec-butyl, isobutyl, etc.) and substituted alkyl groups (e.g., substituted alkyl cycloalkyl groups and substituted cycloalkyl alkyl groups).

Unless otherwise specified, the term "alkyl" includes both "unsubstituted alkyls" and "substituted alkyls." As defined in this document, the term "substituted alkyls" refers to alkyl groups with substituents in place of one or more hydrogens on one or more carbons of the base hydrocarbon. Such substituents may include, for example, the groups alkenyl, alkynyl, halogen, hydroxyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxylcarbonyloxy, aryloxy, aryloxycarbonyloxy, carboxylate, alkylcarbonyl, arylcarbonyl, alkoxylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthiocarbonyl, alkoxyl, phosphate, phosphonate, phosphinate, cyano, amino (including alkylamino, dialkylamino, arylamino, diarylamino and alkylarylamino), acylamino (including alkylcarbonylamino, arylcarbonylamino, carbamoyl and ureido), imino, sulfhydryl, alkylthio, arylthio, thiocarboxylate, sulfates, alkylsulfinyl, sulfonates, sulfamoyl, sulfonamido, nitro, trifluoromethyl, cyano, azido, heterocyclic, alkylaryl or aromatics (including heteroaromatics).

In some cases, substituted alkyl groups may include a heterocyclic group. As used herein, the term "heterocyclic group" includes closed-ring structures analogous to carbocyclic groups in which one or more carbon atoms of the ring are elements other than carbon, for example, nitrogen, sulfur, and oxygen. Heterocyclic groups may be saturated or unsaturated. Examples of heterocyclic groups include, but are not limited to, aziridine, ethylene oxide (epoxides, oxiranes), thiarane (episulfides), dioxirane, azetidine, oxetane, thiethane, dioxethane, dithiethane, dithiide, azolidine, pyrrolidine, pyrroline, oxolane, dihydrofuran, and furan.

Compounds of the invention

The present invention relates, at least in part, to sulfoperoxycarboxylic acids, their compositions, and their use in a variety of bleaching, disinfection, and cleaning applications. The sulfoperoxycarboxylic acids of the present invention are also useful as coupling agents. Furthermore, certain compounds of the present invention may be derived from renewable, non-petroleum-based oils, for example, castor, pine, soybean, canola, olive, peanut, tallow, rapeseed, and palm oils.

As used in this document, the term "sulfoperoxycarboxylic acid" or "sulfonated peroxycarboxylic acid" refers to the peroxycarboxylic acid form of a sulfonated carboxylic acid. The sulfoperoxycarboxylic acids of the present invention may be used independently or combined with other ingredients. In some cases, the compositions of the present invention may include one or more of the sulfoperoxycarboxylic acids of the present invention.

Peroxycarboxylic acids (or percarboxylic acids) generally have the formula R(CO₃H)_n, where, for example, R is an alkyl, arylalkyl, cycloalkyl, aromatic, or heterocyclic group, en is one, two, or three, and is named by prefixing the parent acid with peroxy. Percarboxylic acids can be created by the direct acid-catalyzed equilibrium action of hydrogen peroxide with the carboxylic acid, by auto-oxidation of aldehydes or acid chlorides, and carboxylic hydrides or anhydrides with hydrogen or sodium peroxide. The R group can be saturated or unsaturated, as well as substituted or unsubstituted.

The chemical structures found in this document were represented according to known conventional standards. Thus, in places where an atom, such as a carbon atom, appears to be drawn in a certain way, the structure is represented in accordance with conventional standards. suggests it has an unsatisfied valence, it is assumed that this valence is satisfied by a hydrogen atom, even if that atom has not necessarily been explicitly represented. The structures of some of the compounds of this invention include stereogenic carbon atoms. It is necessary to understand that isomers resulting from this asymmetry (e.g., all enantiomers and diastereomers) are included within the scope of this invention, unless otherwise indicated. That is, unless otherwise determined, any chiral carbon center can be of (R) or (S) stereochemistry. These isomers can be obtained in a substantially pure form by means of classical separation techniques and by stereochemically controlled synthesis. Furthermore, the alkenes can include E or Z geometry, if applicable. Additionally, the compounds of the present invention can exist in both non-solvated and solvated forms, with acceptable solvents such as water, THF, ethanol, and the like. In general, solvated forms are considered equivalent to non-solvated forms for the purposes of the present invention.

In some respects, the present invention relates to sulfoperoxycarboxylic acids with Formula I:

Ri--CH —R₂—COOOH

ONLY₃X⁺ (Formula I)

Where Ri is hydrogen or a substituted or unsubstituted alkyl group;

R₂ It is a substituted or unsubstituted alkyl group;

X is hydrogen, a cationic group, or an ester that forms a group; salts or esters thereof.

In some cases, it is a C alkyl group._m substituted or not; X is hydrogen, a cationic group, or an ester that forms a group; R₂ It is a C alkyl group._n substituted or not; m=1 to 10; n = 1 to 10; m+n less than 18, or salts, esters or mixtures thereof.

In other cases, Rí is hydrogen. Rí can also be a substituted or unsubstituted alkyl group. In certain cases, Rí is a substituted or unsubstituted alkyl group that does not include a cyclic alkyl group. In others, Rí is a substituted alkyl group. Rí can also be an unsubstituted C1-C9 alkyl group. In certain cases, Rí is a C alkyl group.₇ or C₈ not substituted. In others, Ri is a C alkyl group.₈ - Cw substituted. Ri can also be a C alkyl group.₈-W₁₀ replaced by at least 1 or 2 hydroxyl groups. In other cases, R is a C1-C1 alkyl group.₉ substituted. In others, Rí is a C1-C9 alkyl group substituted by at least one SO group.₃H.

Rí can also be a C-alkyl group.₉-Cw substituted. In certain cases, Rí is a C alkyl group.₉-Ci₀ A substituted carbon is one in which at least two of the carbons on the base carbon form a heterocyclic group. This heterocyclic group may be an epoxide group in certain cases.

In certain cases, R₂ It is a substituted C1 to Cw alkyl group. In others, R₂ It is a C alkyl group.₈-Ci₀ replaced. R₂ It could also be a C alkyl group.₆-W₉ not replaced. In certain situations, R₂ It is a C alkyl group.₈ in other cases, R₂ It is a Cw alkyl group substituted by at least two hydroxyl groups. R₂ It could also be a C alkyl group.₈ replaced by at least one SO3H group. R₂ It could still be a Group C.₉ Substituted in which at least two of the carbons on the base carbon form a heterocyclic group. This heterocyclic group may be an epoxide group in certain cases. In some cases, R is a C₆ alkyl group.₈-W₉replaced or not, and R₂ It is a C alkyl group.₇-W₈ Replaced or not.

In others, the compound of the invention is selected from a group consisting of:

III

CH₃(CH₂)₇---c---c---c---(CH₂)₆---z£₀

OH OHSO

H HH

CH₃(CH₂)₆---c—ç—ç---(CH₂)₇

OHSO

H HH ch₃(ch₂)₇—ii[—_(Wh₂₎₆H |H so₃ho

--O---OH .0

--O--OH

<img file="BRPI0907918A2_D0001.tif" />

H H H

III

HC---C---C (CH₂)₇ only₃h so₃h

<img file="BRPI0907918A2_D0002.tif" />

<img file="BRPI0907918A2_D0003.tif" />

<img file="BRPI0907918A2_D0004.tif" />

and their mixtures and derivatives.

In other cases, the compound of the invention is selected from a group consisting of:

H H H o

III z

CH₃(CH₂)₆----Ç---ç---ç---CH₂(CH₂)₆

ONLY₃H OH OH

H H H ch₃(Ch₂)₆—c—C\/C—(^CH2)?

ONLY₃H⁰

<img file="BRPI0907918A2_D0005.tif" />

<img file="BRPI0907918A2_D0006.tif" />

H H H so₃h oh n

H H H ch₃(ch₂)₇—|—।—c—_(CH2)₆ONLY₃H H

<img file="BRPI0907918A2_D0007.tif" />

H H H

CH₃(CH₂)₇----।---।----c----(CH₂)₆ only₃h so₃h

<img file="BRPI0907918A2_D0008.tif" />

Ϊ Ϊ h₃c—ç—C---(CH₂)₇ only₃h

<img file="BRPI0907918A2_D0009.tif" />

and their mixtures and derivatives.

The compounds of the invention are also presented below in Table 1.

Table 1.

<td colspan="2">Sulfonated peroxyacid compounds</td>

<td>ID</td><td>Structure/Name of the compound</td>

<td>THE</td><td>H H H III /° CH₃(CH₂)₆—' I '_(CH2)7---Z_₀___0H^H II Oh so₃H 10-hydroxy-9-sulfooctadecaneperoxoic acid</td>

<td>B</td><td>ϊ ϊ Ϊ /° CH₃(CH₂)₇_ Ç—A—_(WH₂₎₆--^0—OH Oh oh so₃H 9,10-Dihydroxy-8-sulfooctadecaneperoxoic acid</td>

<td>W</td><td>CH₃(CH₂)₇---c---ç---C----(CH₂)₆-------_OHΠ Π only₃h 9-sulfooctadecaneperoxoic acid</td>

<td>D</td><td>H H H¹¹¹ / HÇ—c--C--(CH₂)₇---U—Q--_0Honly₃h 11-sulfoundecaneperoxoic acid</td>

<td>AND</td><td>LLL / í í^s ° ^OHonly₃h so₃h 10,11-disulfoundecaneperoxoic acid</td>

<td>F</td><td>8-(3-octyloxiran-2-yl)-8-sulfooctaneperoxoic acid III CH₃(CH₂)₇—I —_(Wh₂₎₆^ZL_the__oh⁰ only₃h</td>

<td>G</td><td>H H H o 1 1 1 / CH₃(CH₂)₆ Ç Ç Ç CH₂(CH₂)₆---- ---0 OH only₃h oh oh 9,10-Dihydroxy-11-sulfooctadecaneperoxoic acid</td>

<td>H</td><td>HHH III /° CH₃(CH₂)₆— I— C—C—_(WH₂₎₇---OH S₃H⁰8-(3-octyloxiran-2-yl)-8-sulfooctaneperoxoic acid</td>

<td>I</td><td>9-hydroxy-10-sulfooctadecaneperoxoic acid H H H III /° CH₃(CH₂)₇---q---o---c---(CH₂)₆---U—q---_0HONLY₃H OH h</td>

<img file="BRPI0907918A2_D0010.tif" />

In some cases, the starting material for the preparation of the compounds of the present invention is a sulfonated fatty acid. Without wishing to be bound to any particular theory, it is believed that the sulfo- group is inert in an oxidative environment. Furthermore, it is believed that the hydrophilicity of the sulfo- group is not as affected by pH as in other substituents. In certain cases, the sulfonated percarboxylic acids of the present invention are formed from commercially available sulfonated fatty acids. In others, the compounds of the present invention are formed from commercially available non-sulfonated fatty acids, which can be sulfonated. In other situations, the initial fatty acid will be sulfonated before conversion to peroxycarboxylic acid. In others, the initial fatty acid will be sulfonated at the same time as, or after, the formation of the peroxycarboxylic acid. Sulfonated fatty acids suitable for use in the formation of compounds of the present invention include, but are not limited to, 11-sulfoundecanoic acid, 10,11-disulfoundecanoic acid, sulfonated oleic acid, sulfonated linoleic acid, sulfonated palmitoleic acid, and sulfonated stearic acid.

Without wishing to be bound to any particular theory, it is believed that the peracid formed from certain commercially available sulfonated oleic acid starting materials includes a mixture of compounds of the present invention. This is believed to be due, in part, to the nature of the sulfonated oleic acid starting material. In other words, it is believed that, since the initial material of sulfonated oleic acid is derived from natural sources, it is not chemically pure, that is, it does not contain only one form of sulfonated oleic acid. Thus, without being tied to any particular theory, it is believed that the sulfonated peroleic acid formed (hereinafter “sulfonated peroleic acid product”) may include a mixture of compounds A, N, I, and O as the main components. Without being tied to any particular theory, it is believed that, in some cases, the sulfonated peroleic acid product includes about 20 to 25% by weight of Compound A (10-hydroxy-9-sulfooctadecaneperoxoic acid), about 20 to 25% by weight of Compound N (10,11-dihydroxy-9-sulfooctadecaneperoxoic acid), about 20 to 25% by weight of Compound I (9-hydroxy-10-sulfooctadecaneperoxoic acid), and about 20 to 25% by weight of Compound O (8,9-dihydroxy-10-sulfooctadecaneperoxoic acid). It is believed that the remainder of the product comprises approximately 5 to 10% of the weight of a mixture of these compounds.

Sulfoperoxyacids can be formed using various reaction mechanisms. For example, in some cases, peracids are formed by the direct acid-catalyzed equilibrium reaction of hydrogen peroxide with the starting materials.

In certain cases, the sulfonated carboxylic acids used in the formation of compounds of the present invention are not sulfonated at the α-position. It has been found that having the sulfonated group at the α-position of the fatty acid prohibits the oxidation and/or perhydrolysis of the carboxylic acid group to form the corresponding peroxycarboxylic acid. Without wanting to be tied to any particular theory, it is believed that the α-sulfo group causes the carboxylic acid group of the fatty acid to become electronically deficient and, therefore, oxidation and/or perhydrolysis and the formation of the corresponding percarboxylic acid do not occur.

Sulfonated peroxycarboxylic acid compositions

In some respects, the present invention relates to compositions that include a sulfonated peroxycarboxylic acid compound, or mixtures thereof, of Formula I. The compositions of the present invention can be used as bleaching compositions for a variety of substrates and surfaces, for example, textiles, hard surfaces. The compositions of the present invention can also be used as disinfectant or antimicrobial compositions. Furthermore, the compounds of the present invention can be used as coupling agents in compositions for various applications, for example, food contact sanitization, hard surface disinfection, and textile disinfection. In some cases, the compositions containing compounds of the present invention can be multi-purpose. That is, the compositions of the present invention can, for example, act as antimicrobial and bleaching agents, or as coupling and bleaching agents.

The compositions of the present invention also demonstrate greater stability when compared to conventional peroxygen-based compositions. In certain cases, the compositions of the present invention are stable for at least about 1 year at room temperature. In others, the compositions of the present invention are stable at about 37.8 °C (100 °F) for at least 30 days. The compositions of the present invention are also stable at about 60 °C (140 °F) for at least 30 days. For example, 11-sulfoundecanoic peroxyacid (Compound D) is stable as a powder system at about 60 °C (140 °F) for at least 30 days.

The compositions of the present invention have little or no odor. For example, in some cases, the compositions of the present invention have a less unpleasant odor than 5, 4, 3, 2, or 1% by weight of acetic acid in water (measured by a hedonic tone assessment). In others, the compositions of the present invention have no odor detectable by the user.

In certain situations, the compositions of the present invention include a sulfonated peracid or mixtures thereof, as per Formula I, and at least one additional ingredient. Suitable additional ingredients for use with the compositions of the present invention include, but are not limited to, oxidizing agents, carboxylic acids, surfactants, stabilizing agents (e.g., metal chelators) and mixtures thereof. The compounds and compositions of the invention can also be used in conjunction with conventional cleaning agents, for example, alkaline detergents.

In some cases, the compositions of the present invention can be used as a sanitizing composition for items cleaned with a clean-in-place (CIP) technique. These compositions may include an oxidizing agent, a stabilizing agent, an acidulant, and a surfactant, or mixtures thereof, in the following concentrations.

Table A — Concentrated disinfectant for CIP by % of weight

<td>Oxidizing agent</td><td> 0.1 -10</td><td> 2-8</td><td> 5-7</td>

<td>Stabilizing agent</td><td> 0.1-10</td><td> 0.5-5</td><td> 1-2</td>

<td>Acidulant</td><td> 0-50</td><td> 10-40</td><td> 20-30</td>

<td>Surfactant</td><td> 0-50</td><td> 10-40</td><td> 25-35</td>

In other cases, the compositions of the present invention can be used as a textile disinfectant. These compositions may include an oxidizing agent, a stabilizing agent, and a carboxylic acid in the following concentrations.

Table B. — Concentrated textile disinfectant by % of weight.

<td>Oxidizing agent</td><td> 10-75</td><td> 25-60</td><td> 30-50</td>

<td>Stabilizing agent</td><td> 0.1-10</td><td> 0.5-5</td><td> 2-4</td>

<td>Carboxylic acid</td><td> 1-40</td><td> 10-30</td><td> 20-25</td>

Oxidizing agents

In some respects, the compositions of the present invention include a compound of Formula I. In certain cases, the compositions of the present invention also include at least one oxidizing agent. In others, the compositions of the present invention are basically free of oxidizing agent. When present, the present composition may include a variety of oxidizing agents, such as hydrogen peroxide. The oxidizing agent may be present in sufficient quantity to convert a sulfonated carboxylic acid into a sulfonated peroxycarboxylic acid. In some cases, the oxidizing agent may also possess antimicrobial activity. In others, the oxidizing agent is present in insufficient quantity to exhibit antimicrobial activity.

In certain cases, the compositions of the present invention include from about 0.001% to about 99% of the weight of oxidizing agent. In others, the compositions of the present invention include from about 1% to about 60% of the weight of oxidizing agent. In some cases, the compositions of the invention include from about 50% to about 80% of the weight of oxidizing agent. In others, the compositions of the invention include from about 15% to about 30% of the weight of oxidizing agent. In still other cases, the compositions of the present invention include approximately 25% by weight of oxidizing agent. It should be understood that all ranges and values ​​between them are covered by the present invention.

Examples of inorganic oxidizing agents include the following types of compounds or sources of these compounds, or alkali metal salts, including these types of compounds or forming an adduct with: hydrogen peroxide, hydrogen peroxide-urea complexes or hydrogen peroxide donors: group 1 (IA): oxidizing agents, for example, lithium peroxide, sodium peroxide; Group 2 (IIA): oxidizing agents, for example, magnesium peroxide, calcium peroxide, strontium peroxide, barium peroxide; Group 12 (IIB): oxidizing agents, for example, zinc peroxide; Group 13 (IIIA): oxidizing agents, for example, boron compounds, such as perborates, for example, sodium perborate hexahydrate of the formula Na₂O₂O₂.₂[B₂(THE₂)₂(OH)₄]-6H₂(also called sodium perborate tetrahydrate); sodium peroxiborate tetrahydrate with the formula Na₂B₂(THE₂)₂[(OH)₄]-4H₂Sodium perborate (also called sodium perborate trihydrate); sodium peroxiborate with the formula Na₂O₂₂[B₂(THE₂)₂(OH)₄] (also called sodium perborate monohydrate); group 14 (IVA): oxidizing agents, for example, persilicates and peroxycarbonates, which are also called percarbonates, such as alkali metal persilicates or peroxycarbonates; group 15 (VA): oxidizing agents, for example, peroxynitrous acid and its salts; peroxyphosphoric acids and their salts, for example, perphosphates; Group 16 (VIA): oxidizing agents, for example, peroxysulfuric acids and their salts, such as peroxymonosulfuric and peroxydisulfuric acids and their salts, such as persulfates, for example, sodium persulfate; and Group VIA: oxidizing agents, such as sodium periodate and potassium perchlorate. Other active inorganic oxygen compounds may include transition metal peroxides and other peroxygen compounds, and mixtures thereof. In some cases, the compositions of the present invention use one or more of the inorganic oxidizing agents listed above. Suitable inorganic oxidizing agents include ozone, hydrogen peroxide, hydrogen peroxide adduct, group IIIA oxidizing agent or hydrogen peroxide donors of group VIA oxidizing agent, group VA oxidizing agent, group VIIA oxidizing agent, or mixtures thereof. Suitable examples of these inorganic oxidizing agents include percarbonate, perborate, persulfate, perphosphate, persilicate, or mixtures thereof.

Carboxylic and percarboxylic acids

In some cases, the compositions of the present invention include at least one sulfoperoxycarboxylic acid of the present invention and at least one carboxylic and/or percarboxylic acid. In others, the compositions of the present invention include at least two, three, four, or more carboxylic and/or percarboxylic acids.

In certain cases, the carboxylic acid for use with the compositions of the present invention includes a C1 to C1 carboxylic acid.₂₂In some cases, the carboxylic acid for use with the compositions of the present invention is a C4 carboxylic acid.₅ In others, the carboxylic acid for use with the compositions of the present invention is a C1 to C4 carboxylic acid. Examples of suitable carboxylic acids include, but are not limited to, formic, acetic, propionic, butanoic, pentanoic, hexanoic, heptanoic, octanoic, nonanoic, decanoic, undecanoic, dodecanoic acids, as well as their branched isomers, lactic, maleic, ascorbic, citric, hydroxyacetic, neopentanoic, neoeptanoic, neodecanoic, oxalic, malonic, succinic, glutaric, adipic, pimelic, and subric acids, and mixtures thereof. In some cases, the compositions of the present invention include from about 0.1% to about 80% by weight of a carboxylic acid. In others, the compositions of the present invention include from about 1% to about 60% by weight of a carboxylic acid. In still other cases, the compositions of the present invention include from about 20%, about 30%, or about 40% by weight of a carboxylic acid. The compositions of the present invention also include about 5% to about 10% by weight of acetic acid. In others, the compositions of the present invention include about 5% to about 10% by weight of octanoic acid. In still other cases, the compositions of the present invention include a combination of octanoic acid and acetic acid. In some cases, the compositions of the present invention include a compound of Formula I and at least one peroxycarboxylic acid. The peroxycarboxylic acids useful in the compositions and methods of the present invention include peroxyformic acid, peroxyacetic acid, peroxypropionic acid, peroxybutanoic acid, peroxypentanoic acid, peroxyhexanoic acid, peroxyheptanoic acid, peroxyoctanoic acid, peroxynonanoic acid, peroxydecanoic acid, peroxyundecanoic acid, peroxydecanoic acid or the peroxyacids of their branched-chain isomers, peroxylactic acid, peroxymaleic acid, peroxyascorbic acid, peroxyhydroxyacetic acid, peroxyoxalic acid, peroxymalonic acid, peroxysuccinic acid, peroxyglutaric acid, peroxyadipic, peroxypimelic, and peroxysubric acids, and mixtures thereof. In certain cases, the compositions of the invention utilize a combination of different peroxycarboxylic acids. For example, in some cases, the compositions include one or more C1 to C4 peroxycarboxylic acids and one or more C6 peroxycarboxylic acids.₅ a Cn. In certain cases, the peroxycarboxylic acid Ct a C₄ It is peroxyacetic acid and 0 C acid.₅ Cn is peroxyoctanoic acid. In some cases, the compositions of the present invention include peroxyacetic acid. Peroxyacetic acid (or peracetic acid) is a peroxycarboxylic acid with the formula: CH3COOOH. Generally, peroxyacetic acid is a liquid with a pungent odor at higher concentrations and is very soluble in water, alcohol, ether, and sulfuric acid. Peroxyacetic acid can be prepared by any methods known to qualified persons, including the preparation of acetaldehyde and oxygen in the presence of cobalt acetate. A solution of peroxyacetic acid can be obtained by combining acetic acid with hydrogen peroxide. A 50% solution of peroxyacetic acid can be obtained by combining acetic anhydride, hydrogen peroxide, and sulfuric acid. In some cases, the compositions of the present invention include peroxyoctanoic acid, peroxinonanoic acid, or peroxyheptanoic acid. In others, the compositions include peroxyoctanoic acid. Peroxyoctanoic acid (or peroctanoic acid) is a peroxycarboxylic acid with the formula, n-peroxyoctanoic acid: CH₃(CH₂Peroxyoctanoic acid can be an acid with a straight-chain alkyl group, an acid with a branched alkyl group, or a mixture thereof. Peroxyoctanoic acid can be prepared by any methods known to qualified persons. A solution of peroxyoctanoic acid can be obtained by combining octanoic acid and hydrogen peroxide and a hydrotrope, solvent, or vehicle.

In some cases, the compositions of the present invention include from about 0.1% to about 90% by weight of one or more peroxycarboxylic acids. In others, the compositions of the present invention include from about 1% to about 25% by weight of one or more peroxycarboxylic acids. In still others, the compositions of the present invention include from about 5% to about 10% by weight of one or more peroxycarboxylic acids. The compositions of the present invention also include from about 1% to about 25% by weight of peroxyacetic acid. In other instances, the compositions of the present invention include from about 0.1% to about 10% by weight of peroxyoctanoic acid. In others, the compositions of the present invention include a mixture of about 5% by weight of peroxyacetic acid and about 1.5% by weight of peroxyoctanoic acid.

Surfactants

In some cases, the compositions of the present invention include a surfactant. Surfactants suitable for use with the compositions of the present invention include, but are not limited to, nonionic surfactants, anionic surfactants, and zwitterionic surfactants. In certain cases, the compositions of the present invention include from about 10% to about 50% by weight of a surfactant. In others, the compositions of the present invention include from about 15% to about 30% by weight of a surfactant. The compositions of the present invention may also include about 25% by weight of a surfactant. In certain cases, the compositions of the present invention include from about 100 ppm to about 1,000 ppm of a surfactant.

Non-ionic surfactants

Suitable non-ionic surfactants for use with the compositions of the present invention include alkoxylated surfactants. Suitable alkoxylated surfactants include EO/PO copolymers, capped EO/PO copolymers, alcohol alkoxylates, capped alcohol alkoxylates and mixtures thereof or the like. Suitable alkoxylated surfactants for use as solvents include EO/PO block copolymers, such as Pluronic and Pluronic reverse surfactants; alcohol alkoxylates, such as Dehypon LS-54 (R-(EO)₅(DUST)₄) and Dehypon LS36 (R-(EO)₃(DUST)₆); and capped alcohol alkoxylates, such as Plurafac LF221 and Tegoten EC11; their mixtures or similar products.

Semipolar non-ionic surfactants

The semipolar type of non-ionic surface-active agents is another class of non-ionic surfactants useful in the compositions of the present invention. Semipolar non-ionic surfactants include amine oxides, phosphine oxides, sulfoxides, and their alkoxylated derivatives.

Amine oxides are oxides of tertiary amines corresponding to the general formula:

R²

R¹—(OR⁴)_n-NODE

R³

Where the arrow is a conventional representation of a semipolar bond; and R¹R² and R³ They can be aliphatic, aromatic, heterocyclic, alicyclic, or combinations thereof. Generally, for amine oxides of detergent interest, R¹ It is an alkyl radical with approximately 8 to 24 carbon atoms; R² and R³ They are alkyl or hydroxyalkyl groups with 1 to 3 carbon atoms, or mixtures thereof. R² and R³ They can be linked together, for example, through an oxygen or nitrogen atom, to form a ring structure, R⁴ It is a hydroxyalkylene or alkylene group containing 2 to 3 carbon atoms, and its concentration ranges from 0 to 20. An amine oxide can be generated from the corresponding amine and an oxidizing agent, such as hydrogen peroxide.

Water-soluble functional amine oxide surfactants are selected from octyl, decyl, dodecyl, coconut, tallow or alkyl di (lower alkyl) amine oxides. Concrete examples include the following oxides: octyldimethylamine, nonyldimethylamine, decyldimethylamine, undecyldimethylamine, dodecyldimethylamine, isododecyldimethylamine, tridecyldimethylamine, tetradecyldimethylamine, pentadecyldimethylamine, hexadecyldimethylamine, heptadecyldimethylamine, octadecyldimethylamine, dodecyldipropylamine, tetradecyldipropylamine, hexadecyldipropylamine, tetradecylbutylamine, octadecylbutylamine, bis(2-hydroxyethyl)dodecylamine, bis(2-hydroxyethyl)-3-dodecoxy-1-hydroxypropylamine, dimethyl-(2hydroxydodecyl)amine, 3,6,9-trioctadecyldimethylamine and 3-dodecoxy-2-hydroxypropyldi-(2hydroxyethyl)amine.

Anionic surfactants

The sulfated anionic surfactants suitable for use in the present compositions include alkyl ether sulfates, primary and secondary alkyl sulfates, straight and branched alkyl sulfates, alkyl ethoxysulfates, glycerol oleyl fatty acid sulfates, ethylene oxide phenol alkyl ether sulfates, and glucamine C sulfates.₅-W₁₇ acil-N-fCi -C₄ Alkyl) and -N-fCrCg hydroxyalkyl) and alkyl polysaccharide sulfates, such as alkyl polyglucoside sulfates, and the like. Also included are alkyl sulfates, poly(ethyleneoxy) alkyl ether sulfates and poly(ethyleneoxy) aromatic sulfates, such as ethylene oxide and nonylphenol sulfates or condensation products (typically with 1 to 6 oxyethylene groups per molecule).

Suitable sulfonated anionic surfactants for use in the present compositions also include alkyl sulfonates, primary and secondary alkyl sulfonates, straight and branched alkyl sulfonates, and aromatic sulfonates with or without substituents.

Suitable anionic carboxylate surfactants for use in the present compositions include carboxylic acids (and their salts), such as alkanoic acids (and alkanoates), carboxylic ester acids (e.g., alkyl succinates), carboxylic ether acids, and the like. These carboxylates include ethoxy alkyl carboxylates, ethoxy aryl alkyl carboxylates, polyethoxy alkyl polycarboxylate surfactants and soaps (such as carboxyl alkyl). The secondary carboxylates useful in the present compositions include those containing a carboxyl unit attached to a secondary carbon. The secondary carbon may be in a ring structure, as in p-octyl benzoic acid, or as in substituted alkyl cyclohexyl carboxylates. Secondary carboxylate surfactants generally do not contain ether or ester linkages, nor even a hydroxyl group. Furthermore, they typically lack nitrogen atoms in the main group (amphiphilic portion). Suitable secondary surfactants and soaps generally contain 11 to 13 carbon atoms, although more carbon atoms may be present (e.g., up to 16). Suitable carboxylates also include acylamino acids (and their salts), such as acyl glutamates, acyl peptides, sarcosinates (e.g., N-acyl sarcosinates), taurates (e.g., N-acyl taurates and tauridomethyl fatty acid amides), and the like.

Suitable anionic surfactants include ethoxy alkyl or alkylaryl carboxylates of the following formula:

R - O - (CH₂CH₂O)n(CH₂m - CO₂X (3)

where R is an alkyl group C₈ C₂₂ or, where R¹ It is a C alkyl group.₄-Ci₆n is an integer from 1 to 20; m is an integer from 1 to 3; and X is a counterion, such as hydrogen, sodium, potassium, lithium, ammonium, or an amine salt, such as monoethanolamine, diethanolamine, or triethanolamine. In some cases, n is an integer from 4 to 10 and R is 1. In others, R is a C₁₀ alkyl group.₈-W₁₆There are also other cases where R is a C alkyl group.₁₂-W₁₄, né4emé1.

In other cases, R is and R¹ It is a C alkyl group.₆-W₁₂In others, R¹ It is a C alkyl group.₉, n is 10 in is 1.

These alkyl and alkylaryl ethoxy carboxylates are commercially available. These ethoxy carboxylates are typically available as acidic forms, which can be easily converted to an anionic or salt form. Commercially available carboxylates include Neodox 23-4, a C1 polyethoxyalkyl (4) carboxylic acid.₂.i₃ (Shell Chemical) and Emcol CNP-110, a C (10) polyethoxyalkylaryl carboxylic acid_g (Witco Chemical). Carboxylates are also available through Clariant, such as the product Sandopan® DTC, a C polyethoxyalkyl carboxylic acid (7).₁₃.

Amphoteric surfactants

Amphoteric, or ampholytic, surfactants contain both a basic group and an acidic hydrophilic group, in addition to an organic hydrophobic group. These ionic entities can be any of the anionic and cationic groups described in this document for other types of surfactants. A basic nitrogen group and an acidic carboxylate group are the typical functional groups employed as both basic and acidic hydrophilic groups. In some surfactants, the negative charge is provided through sulfonate, sulfate, phosphonate, or phosphate.

Amphoteric surfactants can be generically described as derivatives of aliphatic secondary and tertiary amines, wherein the aliphatic radical can be straight-chain or branched, and one of the aliphatic substituents contains about 8 to 18 carbon atoms and one contains an anionic water solubilization group, for example, carboxy, sulfo, sulfate, phosphate, or phosphono. Amphoteric surfactants are subdivided into two main classes known to those qualified in this area and described in “Surfactant Encyclopedia” Cosmetics &amp; Toiletries. Vol. 104 (2) 69-71 (1989). The first class includes acyl/dialkyl ethylenediamine derivatives (such as 2-alkyl hydroxyethyl imidazoline derivatives) and their salts. The second category includes N-alkylamino acids and their salts. Some amphoteric surfactants may fall into both classes.

Amphoteric surfactants can be synthesized by methods known to qualified persons. For example, 2-alkyl hydroxyethyl imidazoline is synthesized by condensation and ring closure of a long-chain carboxylic acid (or a derivative) with ethylenediamine dialkyl. Commercial amphoteric surfactants are derived by subsequent hydrolysis and ring opening of imidazoline by alkylation, for example, with chloroacetic acid or ethyl acetate. During alkylation, one or two carboxyalkyl groups react to form a tertiary amine and an ether linkage with different alkylating agents, producing different tertiary amines.

Long-chain imidazole derivatives used in the present invention generally have the following general formula:

(MONO)ACETATE (DI)PROPIONATE AMPHOTERIC

SULFONATE

CH₂COO® CH₂CH₂COO®_oh

RCONHCH₂CH₂N®H RCONHCH₂CH₂Ú®CH₂CH₂COOH CH₂CHCH₂ONLY₃®Na®

Oh₂ch₂oh ch₂ch₂oh rconhch₂ch₂n^ ch₂ch₂oh

Neutral pH - Zwitterion

Where R is an acyclic hydrophobic group with about 8 to 18 carbon atoms and M is a cation to neutralize the charge of the anion, usually sodium. Commercially known imidazoline amphoteric derivatives that can be used in the present compositions include, for example: Cocoamphopropionate, Cocoamphocarboxypropionate, Cocoamphoglycinate, Cocoamphocarboxyglycinate, Cocoamphopropylsulfonate and Cocoamphocarboxypropionic acid. Amphocarboxylic acids can be produced from fatty imidazolines in which the dicarboxylic acid functionality of the amphodicarboxylic acid is a diacetic and/or dipropionic acid.

The carboxymethylated compounds (glycinates) described above are often called betaines. Betaines are a special class of amphoteric surfactants discussed below in the section entitled "Zwitterionic Surfactants".

Long-chain N-alkylamino acids are readily prepared by an RNH reaction.₂, in which straight or branched chain alkyl R=C₈-W₁₈N-alkylamines are fatty amines with halogenated carboxylic acids. Alkylation of the primary amino groups of an amino acid results in secondary and tertiary amines. Alkyl substituents may have additional amino groups that provide more than one reactive nitrogen center. Most commercial N-alkylamine acids are alkyl derivatives of beta-alanine or beta-N(2-carboxyethyl)alanine. Examples of commercially available N-alkylamino acid ampholytes with application in this invention include beta-amino alkyl dipropionates, RN(C₂H₄(COM)₂ and RNHC₂H₄In certain cases, R can be an acyclic hydrophobic group containing about 8 to 18 carbon atoms, and M is a cation to neutralize the charge of the anion.

Suitable amphoteric surfactants include those derived from coconut products, such as coconut oil or fatty acids. Other suitable coconut-derived surfactants include, as part of their structure, an ethylenediamine group, an alkanolamide group, an amino acid group, for example, glycine, or a combination thereof, and an aliphatic substituent of about 8 to 18 carbon atoms (e.g., 12). This surfactant may also be considered an alkyl amphodicarboxylic acid. These amphoteric surfactants may include chemical structures represented as: Ci₂-alkyl-C(O)-NH-CH₂-CH₂N⁺(CH2-CH2-CO2Na)2-CH2-CH2-OH or C12-alkyl-C(O)-N(H)-CH2-CH2-N⁺(CH2-CO₂Na)₂CH₂-CH₂-OH. Disodium cocoampho dipropionate is a suitable and commercially available amphoteric surfactant under the brand name Miranol™ FBS from Rhodia Inc., Cranbury, NJ, USA. Another suitable coco-derived amphoteric surfactant with the chemical name disodium cocoampho diacetate is sold under the brand name Mirataine™ JCHA, also from Rhodia Inc., Cranbury, NJ, USA.

A typical listing of amphoteric classes, and species of these surfactants, is provided in U.S. Patent No. 3,929,678 issued to Laughlin and Heuring on December 30, 1975. Other examples are provided in “Surface Active Agents and Detergents” (Vol. I and II by Schwartz, Perry, and Berch).

Zwitterionic surfactants

Zwitterionic surfactants can be considered a subset of amphoteric surfactants and may include an anionic charge. Zwitterionic surfactants can be generically described as derivatives of secondary and tertiary amines, derivatives of heterocyclic secondary and tertiary amines, or derivatives of quaternary ammonium, quaternary phosphonium, or tertiary sulfonium compounds. Typically, a zwitterionic surfactant includes a positively charged quaternary ammonium group or, in some cases, a sulfonium or phosphonium ion, a negatively charged carboxyl group, and an alkyl group. Zwitterions generally contain cationic and anionic groups that ionize at a level nearly identical to the isoelectric region of the molecule and that can develop strong attraction in the internal salt between the positive-negative charge centers. Examples of such synthetic zwitterionic surfactants include aliphatic quaternary ammonium derivatives, phosphonium and sulfonium compounds in which the aliphatic radicals may be straight-chain or branched and in which one of the aliphatic substituents contains 8 to 18 carbon atoms and one contains an anionic water solubilization group, for example, carboxyl, sulfonate, sulfate, phosphate or phosphonate. Betaine and sultaine surfactants are examples of zwitterionic surfactants for use in this document.

The general formula for these compounds is:

(1¾ l₊ 3 ' ry-ch₂-r—z

In which R¹ contains an alkyl, alkenyl, or hydroxyalkyl radical of 8 to 18 carbon atoms and 0 to 10 ethylene oxide groups and 0 to 1 glyceryl group, Y is selected from the group consisting of nitrogen, phosphorus, and sulfur atoms, R² is an alkyl or monohydroxy alkyl group containing 1 to 3 carbon atoms, x is 1 when Y is a sulfur atom and 2 when Y is a nitrogen or phosphorus atom, R³ It is an alkylene or hydroxyalkylene with 1 to 4 carbon atoms, and Z is a radical selected from the group composed of carboxylate, sulfonate, sulfate, phosphonate, and phosphate groups.

Examples of zwitterionic surfactants with the structures listed above: 4-[N,N-di(2-hydroxyethyl)-N-octadecylammonium]-butane-1-carboxylate; 5-[S-3-hydroxypropyl-Shexadecylsulfonium]-3-hydroxypentane-1-sulfate; 3-[P,P-diethyl-P-3,6,9-trioxatetracosanephosphonium]-2-hydroxypropane-1-phosphate; 3-[N,N-dipropyl-N-3-dodecoxy-2-hydroxypropyl-ammonium]-propane-1-phosphonate; 3-(N,N-dimethyl-N-hexadecylammonium)-propane-1-sulfonate; 3-(N,N-dimethyl-N-hexadecylammonium)-2-hydroxypropane-1-sulfonate; 4-[N,N-di(2(2-hydroxyethyl)-N(2-hydroxydodecyl)ammonium]-butane-1-carboxylate; 3-[S-ethyl-S-(3-dodecoxy-2-hydroxypropyl)sulfonium]-propane-1-phosphate; 3-[P,P-dimethyl-P-dodecylphosphonium]-propane-1-phosphonate; and S[N,N-di(3-hydroxypropyl)-N-hexadecylammonium]-2-hydroxypentane-1-sulfate. The alkyl groups contained in said detergent surfactants may be straight or branched, saturated or unsaturated.

The zwitterionic surfactant suitable for use in the present compositions includes a betaine with the following general structure:

¹¹ ”

RR R

RN-CH₂-CO₂ R— S—CH2-CO2 R— P—CH2-CO2 r” r

These surfactant betaines typically do not exhibit strong anionic or cationic characteristics at extreme pH nor do they demonstrate reduced water solubility in their isoelectric range. Unlike "external" quaternary ammonium salts, betaines are anionically compatible. Examples of suitable betaines include coconut acylamidopropyldimethyl betaine; hexadecyl dimethyl betaine; and C-acylamidopropyl betaine.₁₂.i₄; betaine acylamidohexyldiethyl C₈.14; acylmethylamidodiethylammonium-1-carboxybutane 4-C₁₄._1sacylamidodimethylbetaine C₁₆.₁₈; acylamidopentanediethylbetaine C₁₂-ie; and acylmethylamidodimethylbetaine C₁₂-ie.

The sultaines useful in the present invention include compounds with the formula (R(R¹)2 N⁺ R²ONLY³', in which R is a C8-C hydrocarbyl group₁₈each R¹ In general, it is a CtC alkyl group.₃independent, for example, methyl, and R² It is a CrCe hydrocarbyl group, such as a C1-C3 alkylene or hydroxyalkylene group.

A typical listing of zwitterionic classes, and species of these surfactants, is provided in U.S. Patent No. 3,929,678 issued to Laughlin and Heuring on December 30, 1975. Other examples are provided in “Surface Active Agents and Detergents” (Vol. I and II by Schwartz, Perry, and Berch).

In certain cases, the compositions of the present invention include a betaine. For example, the compositions may include cocoamidopropyl betaine.

Other additional ingredients

In some cases, the compositions of the present invention may include other additional ingredients. Suitable additional ingredients for use with the compositions of the present invention include, but are not limited to, acidulants, stabilizing agents, for example, chelating or sequestering agents, buffers, detergents, wetting agents, antifoaming agents, thickeners, foaming agents, solidifying agents, aesthetic enhancement agents (i.e., colorants, odors or perfumes) and other cleaning agents. These additional ingredients can be pre-formulated with the compositions of the invention or added to the system before, after, or essentially simultaneously with the addition of the compositions of the present invention. Furthermore, the compositions can be used in conjunction with one or more conventional cleaning agents, for example, an alkaline detergent.

Acidulants

In some cases, the compositions of the present invention include an acidulant. The acidulant may act as a catalyst for the conversion of carboxylic acid to peroxycarboxylic acid. The acidulant may be effective in forming a concentrate composition with a pH of about 1 or less. The acidulant may be effective in forming a workable composition with a pH of about 5 or less, about 4 or less, about 3 or less, about 2 or less, or similar. In certain cases, an acidulant may be used to lower the pH of an alkaline cleaning solution to a pH of about 10 or less, about 9 or less, about 8 or less, about 7 or less, or about 6 or less. In others, the acidulant includes an inorganic acid. Suitable inorganic acids include, but are not limited to, sulfuric acid, sodium bisulfate, phosphoric acid, nitric acid, and hydrochloric acid. In others, the acidulant includes an organic acid. Suitable organic acids include, but are not limited to, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, xylenesulfonic acid, benzenesulfonic acid, formic acid, acetic acid, mono-, di-, or trihalocarboxylic acids, picolinic acid, dipicolinic acid, and mixtures thereof. In some cases, the compositions of the present invention contain little or no phosphorus-based acid.

In some cases, the selected acidulant may also function as a stabilizing agent. Therefore, the compositions of the present invention may be essentially free of an additional stabilizing agent.

In certain cases, the composition includes approximately 0.5 to approximately 80% by weight of acidulant, approximately 1 to 50% by weight, approximately 5 to 30% by weight of acidulant, or approximately 7 to 14% by weight of acidulant. It is understood that all values ​​and ranges thereof are encompassed by the compositions of the present invention.

Stabilizing agents

In some cases, the compositions of the present invention include one or more stabilizing agents. Stabilizing agents can be used, for example, to stabilize peracid and hydrogen peroxide and prevent premature oxidation of this component in the composition of the invention.

In certain cases, an acidic stabilizing agent may be used. Thus, in some cases, the compositions of the present invention may be essentially free of an additional acidulant.

Suitable stabilizing agents include, for example, chelating or sequestering agents. Suitable sequestering agents include, but are not limited to, organic chelating compounds that sequester metal ions from solution, especially transition metal ions. These sequestrants include amino acid or hydroxyphosphonic acid complexing agents (in acid or soluble salt form), carboxylic acids (e.g., polymeric polycarboxylate), hydroxycarboxylic acids, aminocarboxylic acids, or heterocyclic carboxylic acids, such as pyridine-2,6-dicarboxylic acid (dipicolinic acid).

In some cases, the compositions of the present invention include dipicolinic acid as a stabilizing agent. Compositions that include dipicolinic acid can be formulated to have little or no phosphorus. It has also been observed that the inclusion of dipicolinic acid in a composition of the present invention helps to achieve phase stability of the compositions, compared to other conventional stabilizing agents, such as 1-hydroxyethylidene-1,1-diphosphonic acid (CH3).₃C(PO3H₂)2OH) (HEDP).

In other cases, the sequestrant may be or include phosphonic acid or a phosphonate salt. Suitable phosphonic acids and phosphonate salts include HEDP; ethylenediaminetetramethylenephosphonic acid (EDTMP); diethylenetriaminepentamethylenephosphonic acid (DTPMP); cyclohexane-1,2-tetramethylenephosphonic acid; amino[tri(methylenephosphonic)] acid; (ethylenediamine[tetramethylenephosphonic)] acid; 2-phosphenobutane-1,2,4-tricarboxylic acid, or their salts, such as alkali metal, ammonium or alkyl amine salts, including mono-, di- or tetraethanolamine salts; Picolinic acid, dipicolinic acid, or mixtures thereof. In some cases, organic phosphonates, such as HEDP, are included in the compositions of the present invention.

Commercially available food additive chelating agents include phosphonates sold under the trade name DEQUEST®, including, for example, 1-hydroxyethylidene-IJ-diphosphonic acid, made available by Monsanto Industrial Chemicals Co., St. Louis, MO, USA, as DEQUEST® 2010; amino(tri(methylenephosphonic)) acid (N[CH2PO₃H₂]3), made available by Monsanto as DEQUEST® 2000; ethylenediamine[tetra(methylenephosphonic)] acid made available by Monsanto as DEQUEST® 2041; and 2-phosphonobutane-1,2,4-tricarboxylic acid, made available by Mobay Chemical Corporation, Inorganic Chemicals Division, Pittsburgh, PA, USA, as Bayhibit AM.

The sequestrant may be or include a type of aminocarboxylic acid. Suitable aminocarboxylic acid-type sequestrants include alkali metal acids or their salts, such as aminoacetates and their salts. Suitable aminocarboxylates include N-hydroxyethylaminodiacetic acid; hydroxyethylenediaminetetraacetic acid, nitrilotriacetic acid (NTA), ethylenediaminetetraacetic acid (EDTA), N-hydroxyethylethylenediaminetriacetic acid (HEDTA); diethylenetriaminepentaacetic acid (DTPA) and alanine-N,N-diacetic acid, and their similar compounds and mixtures.

The sequestrant may be or include a polycarboxylate. Suitable polycarboxylates include, for example, polyacrylic acid, maleic/olefin copolymer, acrylic/maleic copolymer, polymethacrylic acid, acrylic-methacrylic acid copolymers, hydrolyzed polyacrylamide, hydrolyzed polymethacrylamide, hydrolyzed polyamide-methacrylamide copolymers, hydrolyzed polyacrylonitrile, hydrolyzed polymethacrylonitrile, hydrolyzed acrylonitrile-methacrylonitrile copolymers, polymaleic acid, polyfumaric acid, Copolymers of acrylic and itaconic acid, phosphine polycarboxylate, their acidic or salt forms, mixtures and the like.

In certain cases, the present composition includes approximately 0.01 to 10% by weight of stabilizing agent, approximately 0.4 to 4% by weight of stabilizing agent, approximately 0.6 to 3% by weight of stabilizing agent, and approximately 1 to 2% by weight of stabilizing agent. It should be understood that all values ​​and ranges therebetween are covered by the present invention.

Wetting or anti-foaming agents

Wetting and antifoaming agents are also useful in the compositions of the invention. Wetting agents function to increase the surface contact or penetration activity of the antimicrobial composition of the invention. Wetting agents that can be used in the composition of the invention include components known to increase the surface activity of the composition of the invention.

Generally, the antifoaming agents that can be used according to the invention include silica and silicones; aliphatic acids or esters; alcohols; sulfates or sulfonates; amines or amides; halogenated compounds, such as fluorochlorohydrocarbons; vegetable oils, waxes, mineral oils, as well as their sulfonated or sulfated derivatives; fatty acids and/or their soaps, such as alkalis, alkaline earth metal soaps; and phosphate esters and phosphates, such as alkaline and alkyl diphosphates, and tributyl phosphates, among others; and mixtures thereof.

In some cases, the compositions of the present invention may include food-grade antifoaming agents due to the application of the invention's method. For this purpose, one of the most effective antifoaming agents includes silicones. Silicones, such as dimethylsilicone, polysiloxane glycol, polysiloxanemethylphenol, tetraalkyl or trialkyl silanes, hydrophobic silica antifoams, and mixtures thereof, can be used in antifoaming applications. Commonly available commercial antifoams include silicones such as Ardefoam®, from Armour Industrial Chemical Company, which is a silicone bonded to an organic emulsion; Foam Kill® or Kresseo®, offered by Krusable Chemical Company, which are silicone and non-silicone type antifoams, as well as silicone esters; and Anti-Foam A® and DC-200, from Dow Corning Corporation, which are food-grade silicones, among others. These antifoaming agents may be present in concentrations ranging from about 0.01% to 20% by weight, from about 0.01% to 5% by weight, or from about 0.01% to 1% by weight.

Thickening or chelating agents

The compositions of the present invention may include any varieties of known thickeners. Suitable thickeners include natural gums, such as xanthan gum, guar gum or other vegetable mucilage gums; polysaccharide-based thickeners, such as alginates, starches and cellulosic polymers (e.g., carboxymethylcellulose); polyacrylate thickeners; and hydrocolloid thickeners, such as pectin. In certain cases, the thickener leaves no contaminating residue on the surface of the object. For example, thickening or gelling agents may be compatible with food or other sensitive products in contact areas. Generally, the concentration of the thickener used in the present compositions or methods will be dictated by the desired viscosity of the final composition. However, as a general guideline, the viscosity of the thickener in the present composition varies from about 0.1% to 5% by weight, from about 0.1% to 1.0% by weight, or from about 0.1% to 0.5% by weight.

Solidifying agent

The present compositions may include a solidifying agent, which may participate in maintaining the compositions in solid form. In some cases, the solidifying agent may form and/or maintain the composition as a solid. In others, the solidifying agent may solidify the composition without unacceptably impairing the eventual release of the sulfonated peroxycarboxylic acid. The solidifying agent may include, for example, an inert and neutral organic or inorganic solid compound, or one that makes a functional, stabilizing, or purifying contribution to the present composition. Suitable solidifying agents include solid polyethylene glycol (PEG), solid polypropylene glycol, solid EO/PO block copolymer, amide, urea (also known as carbamide), nonionic surfactant (which may be used as a coupler), anionic surfactant, starch that has been made water-soluble (e.g., through an acid or alkaline treatment process), cellulose that has been made water-soluble, inorganic poly(maleic anhydride/methyl vinyl) ether, Polymethacrylic acid, other generally functional or inert materials with a high melting point, mixtures thereof and the like;

Suitable glycol solidifying agents include solid polyethylene glycol or solid polypropylene glycol, which may, for example, have a molecular weight of approximately 1,400 to about 30,000. In certain cases, the solidifying agent includes or is a solid PEG, for example, PEG 1,500 to PEG 20,000. In others, the PEG includes PEG 1,450, PEG 3,350, PEG 4,500, PEG 8,000, PEG 20,000, and the like. Suitable solid polyethylene glycols are commercially available from Union Carbide under the trade name CARBOWAX.

Suitable amide solidifying agents include stearic monoethanolamide, lauric diethanolamide, stearic diethanolamide, stearic monoethanolamide, cocodiethyleneamide, an alkylamide, mixtures thereof, and the like. In certain cases, the present composition may include glycol (e.g., PEG) and amide.

Suitable nonionic surfactant solidifying agents include nonylphenol ethoxylate, linear alkyl alcohol ethoxylate, ethylene/propylene oxide block copolymer, mixtures thereof, and the like. Suitable ethylene/propylene oxide block copolymers include those sold under the Pluronic brand name (such as Pluronic 108 and Pluronic F68) commercially available from BASF Corporation. In some cases, the nonionic surfactant may be selected to be solid at room temperature or at the temperature at which the composition will be stored or used. In others, the nonionic surfactant may be selected to have reduced solubility in water in combination with the coupling agent. Suitable couplers that may be employed with the nonionic surfactant solidifying agent include propylene glycol, polyethylene glycol and mixtures thereof, or similar products.

Suitable anionic surfactant solidifying agents include linear alkylbenzene sulfonate, alcohol sulfate, alcohol ether sulfate, alpha olefin sulfonate, mixtures thereof, and the like. In certain situations, the anionic surfactant solidifying agent is or includes linear alkylbenzene sulfonate. In others, the anionic surfactant may be selected to be solid at room temperature or at the temperature at which the composition will be stored or used.

Suitable inorganic solidifying agents include phosphate salts (e.g., alkali metal phosphate), sulfate salts (e.g., magnesium sulfate, sodium sulfate, or sodium bisulfate), acetate salts (e.g., anhydrous sodium acetate), borates (e.g., sodium borate), silicates (e.g., precipitated or vaporized forms (e.g., Sipernat 50®, made available by Degussa)), carbonate salts (e.g., calcium carbonate or hydrated carbonate), Other known hydratable compounds, mixtures thereof, and the like. In one case, the inorganic solidifying agent may include organic phosphonate compounds and carbonate salts, as a form E composition.

In certain cases, the compositions of the present invention may include any agent or combination of agents that provide a necessary degree of solidification and solubility in water and that may be included in the present compositions. In other cases, increasing the concentration of the solidifying agent in the present composition may tend to increase the hardness of the composition. Decreasing the concentration of the solidifying agent may also tend to decrease or soften the concentrated composition.

In certain situations, a solidifying agent may include any organic or inorganic compound that provides a solid characteristic and/or controls the soluble characteristic of the current composition, for example, when placed in an aqueous environment. For instance, a solidifying agent may provide controlled distribution if it has greater solubility in water compared to the other ingredients in the composition. Urea can be one such solidifying agent. Another example: for systems that would benefit from lower aqueous solubility or a slower rate of dissolution, a non-ionic organic or amide hardening agent may be appropriate.

In some cases, the compositions of the present invention may include a solidifying agent that allows for convenient processing or manufacturing of the present composition. For example, the solidifying agent can be selected to form a composition that can harden into solid form at ambient temperatures of about 30 to 50 °C after mixing ceases and the mixture is dispensed from the mixing system, in about 1 minute to 3 hours, or about 2 minutes to 2 hours, or about 5 minutes to 1 hour.

The compositions of the present invention may include a solidifying agent in any effective quantity. The amount of solidifying agent included in this composition may vary depending on the type of composition, its ingredients, its intended use, the amount of distribution solution applied to the solid composition over time during use, the temperature of the distribution solution, the hardness of the distribution solution, the physical size of the solid composition, and the concentration of the other ingredients. The concentration of the cleaning agent in the composition and other similar factors. Suitable amounts may include approximately 1 to 99% of the weight, approximately 1.5 to 85% of the weight, approximately 2 to 80% of the weight, approximately 10 to 45% of the weight, approximately 15% to 40% of the weight, approximately 20% to 30% of the weight, approximately 30% to 70%, approximately 40% to 60%, up to 50% of the weight, approximately 40% to 50%.

Vehicle

In some cases, the compositions of the present invention include a vehicle. The vehicle provides a means that dissolves, suspends, or transports the other components of the composition. For example, the vehicle may provide a means of solubilizing, suspending, or producing a sulfonated peroxycarboxylic acid and for forming a balanced mixture. The vehicle may also function to deliver and wet the composition of the invention onto an object. To that end, the vehicle may contain any component or components that may facilitate these functions.

In certain cases, the vehicle primarily includes water, which can promote solubility and function as a reaction and equilibrium medium. The vehicle may include, or be primarily, an organic solvent, such as simple alkyl alcohols like ethanol, isopropanol, n-propanol, benzyl alcohol, and the like. Polyols are also useful vehicles, including glycerol, sorbitol, and the like.

Suitable vehicles include glycol ethers. Suitable glycol ethers include diethylene glycol n-butyl ether, diethylene glycol n-propyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, diethylene glycol t-butyl ether, dipropylene glycol n-butyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, dipropylene glycol propyl ether, dipropylene glycol tert-butyl ether, ethylene glycol butyl ether, ethylene glycol propyl ether, ethylene glycol ethyl ether. ethylene glycol methyl ether, ethylene glycol methyl ether acetate, propylene glycol n-butyl ether, propylene glycol ethyl ether, propylene glycol methyl ether, propylene glycol n-propyl ether, tripropylene glycol methyl ether and tripropylene glycol n-butyl ether, ethylene glycol phenyl ether (commercially available as DOWANOL EPH™ from Dow Chemical Co.), propylene glycol phenyl ether (commercially available as DOWANOL PPH™ from Dow Chemical Co.), and similar substances or mixtures thereof. Other suitable glycol ethers that are commercially available (all are made available by Union Carbide Corp.) include Butoxyethyl PROPASOL™, Butyl CARBITOL™ acetate, Butyl CARBITOL™, Butyl CELLOSOLVE™ acetate, Butyl CELLOSOLVE™, Butyl DI PROPASOL™, Butyl PROPASOL™, CARBITOL™ PM-600, CARBITOL™ Low Gravity, CELLOSOLVE™ acetate, CELLOSOLVE™, Ester EEP™, FILMER IBT™, Hexyl CARBITOL™, Hexyl CELLOSOLVE™, Methyl CARBITOL™, Methyl CELLOSOLVE™ acetate, Methyl CELLOSOLVE™. Methyl DI PROPASOL™, Methyl PROPASOL™ acetate, Methyl PROPASOL™, Propyl CARBITOL™, Propyl CELLOSOLVE™, Propyl

DIPROPASOL™ and Propyl PROPASOL™.

In some cases, the vehicle comprises a large part of the composition of the invention and may be the balance of the composition in addition to the sulfonated peroxycarboxylic acid, oxidizing agent, additional ingredients, and so on. The concentration and type of vehicle will depend on the nature of the composition as a whole, the storage environment, and the method of application, including the concentration of the sulfonated peroxycarboxylic acid, among other factors. It should be noted that the vehicle must be chosen and used in a concentration that does not inhibit the effectiveness of the sulfonated peroxycarboxylic acid in the composition of the invention for its intended use, for example, bleaching, sanitizing, disinfecting.

In certain cases, the present composition includes approximately 5 to 90% of the vehicle's weight, approximately 10 to 80% of the vehicle's weight, approximately 20 to 60% of the vehicle's weight, or approximately 30 to 40% of the vehicle's weight. It should be understood that all values ​​and ranges therebetween are covered by the present invention.

Compositions for use

The compositions of the present invention include concentrate and use-only compositions. A concentrate composition can be diluted in water, for example, to form a use-only composition. In one case, a concentrate composition can be diluted in a use-only solution before application to an object. For reasons of economy, the concentrate can be marketed and the end user can dilute it in water or an aqueous diluent, transforming it into a use-only solution.

The level of active components in the concentrate composition depends on the desired dilution factor and the intended activity of the sulfonated peroxycarboxylic acid compound. Generally, a dilution of about 1 fluid ounce (29.6 ml) in about 37.8 L (10 gallons) of water to about 10 fluid ounces (296 ml) in about 3.7 L (1 gallon) of water is used for aqueous compositions of the present invention. In some cases, higher dilutions may be used if high operating temperatures (above 25°C) or prolonged exposure times (more than 30 seconds) can be employed. In typical use, the concentrate is diluted with a higher proportion of water using tap water or commonly available utility water, mixing the materials at a dilution ratio of approximately 88.7 ml (3 oz) to 1,183 ml (40 oz) of concentrate per 378 l (100 gallons) of water.

In some cases, when used in laundry applications, the concentrated compositions may be diluted in a dilution ratio of approximately 0.1 g/l to approximately 100 g/l of concentrate to diluent, approximately 0.5 g/l to approximately 10.0 g/l of concentrate to diluent, approximately 1.0 g/l to approximately 4.0 g/l of concentrate to diluent, or approximately 1.0 g/l to approximately 2.0 g/l of concentrate to diluent.

In other cases, a working composition may include about 0.01 to 10% by weight of a concentrated composition and about 90 to 99.99% by weight of diluent; or about 0.1 to 1% by weight of a concentrated composition and about 99 to 99.9% by weight of diluent.

The quantities of an ingredient in a composition for use can be calculated from the quantities listed above for concentrated compositions and these dilution factors. In certain cases, for example, when used in laundry applications, the concentrated compositions of the present invention are diluted in such a way that sulfopercarboxylic acid is present from about 20 ppm to 80 ppm. In others, the concentrated compositions of the present invention are diluted in such a way that sulfopercarboxylic acid is present at about 20, 40, 60, 80, 500, 1,000 or 10,000 ppm to 20,000 ppm. It should be understood that all values ​​and ranges thereafter are covered by the present invention.

Methods employing sulfoperoxycarboxylic acid compounds and compositions

In some respects, the present invention includes methods of using sulfoperoxycarboxylic acid compounds and compositions of the present invention. In certain cases, these methods employ the antimicrobial and/or bleaching activity of sulfoperoxycarboxylic acid. For example, the invention includes a method for reducing microbial population, one for reducing the population of a microorganism on the skin, one for treating a skin disease, one for reducing odor, and/or a bleaching method. These methods can operate on an article, surface, body, or stream of water or gas, or similar, by coming into contact with the article, surface, body, or stream through a sulfoperoxycarboxylic acid compound or composition of the invention. Contacting the compound or composition may include any of several methods of applying a compound or composition of the invention, such as spraying compounds or compositions, immersing the item in the compounds or compositions, foaming or gelling the compounds or composition, or a combination thereof.

In some aspects, a composition of the present invention includes an amount of sulfoperoxycarboxylic acid of the present invention effective in killing one or more of the foodborne pathogenic bacteria associated with a food product, including, but not limited to, Salmonella typhimurium, Salmonella javiana, Campylobacter jejuni, Listeria monocytogenes and Escherichia coli O157:1-17, yeasts and mold. In certain cases, the compositions of the present invention include an amount of sulfoperoxycarboxylic acid effective in killing one or more of the pathogenic bacteria associated with the surface and environments of healthcare facilities, including, but not limited to, Salmonella typhimurium, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, Salmonella choleraesurus, Pseudomonas aeruginosa, Escherichia coli, mycobacteria, yeasts, and mold. The compounds and compositions of the present invention have activity against a wide variety of microorganisms, such as gram-positive bacteria (e.g., Listeria monocytogenes or Staphylococcus aureus) and gram-negative bacteria (e.g., Escherichia coli or Pseudomonas aeruginosa), yeasts, molds, bacterial spores, viruses, etc. The compounds and compositions of the present invention, as described above, can be used against a wide variety of human pathogens. The present compounds and compositions can kill a wide variety of microorganisms on food processing surfaces, food product surfaces, water used to wash or process food products, and healthcare service surfaces or environments.

The compounds of the invention can be used for a variety of domestic or industrial applications, such as reducing microbial or viral populations on a surface, object, body, or water stream. The compounds can be applied in diverse areas, including kitchens, bathrooms, factories, hospitals, dental offices, and food processing plants, and can be applied to numerous hard or soft surfaces with smooth, irregular, or porous topography. Suitable hard surfaces include, for example, architectural surfaces (floors, walls, windows, sinks, tables, countertops, and warning signs); utensils used for eating; medical or surgical instruments and devices with a hard surface; and hard-surface packaging. These hard surfaces can be composed of various materials, including, for example, ceramic, metal, glass, wood, or rigid plastic. Suitable soft surfaces include, for example, paper; filter media; hospital and surgical linens and clothing; medical or surgical instruments and devices with a soft surface; and soft-surface packaging. These soft surfaces can be composed of various materials, including paper, fiber, woven or non-woven fabrics, soft plastics, and elastomers. The compounds of the invention can also be applied to soft surfaces such as food and skin (e.g., hands). These compounds can be used as an environmental disinfectant, with or without foaming.

The compounds and compositions of the invention can be included in products such as sterilizers, disinfectants, preservatives, deodorants, antiseptics, fungicides, germicides, sporicides, virucides, detergents, bleaches, hard surface cleaners, soaps, waterless hand sanitizers, and pre- or post-surgical gowns.

The compounds can also be used in veterinary products, such as mammalian skin treatments, or in products for cleaning or disinfecting animal enclosures, corrals, water supply stations, and veterinary treatment areas, such as examination tables and operating rooms. The present compounds can be used in antimicrobial foot baths for animals or people. The compounds of the present invention can also be used as an antimicrobial udder soak.

In some respects, the compounds of the present invention can be used to reduce the population of pathogenic microorganisms, such as human, animal and similar pathogens. The compounds exhibit activity against pathogens that include fungi, molds, bacteria, spores and viruses, for example, S. aureus, E. coli, Streptococci, Legionella, Pseudomonas aeruginosa, mycobacteria, tuberculosis, bacteriophages or similar organisms. These pathogens can cause a variety of diseases and disorders, including mastitis and other diseases of milking mammals, tuberculosis, and the like. The compounds of the present invention can reduce the population of microorganisms on the skin or other external or mucous surfaces of animals. Furthermore, the present compounds can kill pathogenic microorganisms that spread by water, air, or surface substrate transfer. The compounds only need to be applied to the skin, other external surfaces or mucous membranes of an animal, water, air or surface.

In some cases, the compounds and compositions of the present invention can be used to reduce the prion population on a surface. Prions are infectious protein particles devoid of nucleic acid. Prions are known to cause a variety of brain diseases, including kuru, Creutzfeldt-Jakob disease, Gerstmann-Straussler-Scheinker disease, and fatal familial insomnia in humans; scrapie in sheep; bovine spongiform encephalopathy (mad cow disease) in cattle; transmissible mink encephalopathy in minks; chronic wasting disease in deer and elk; and feline spongiform encephalopathy in cats. These diseases result in symptoms that include dementia, ataxia, behavioral disorders, vertigo, involuntary movements, and death. Prions can be transmitted primarily through exposure to infected tissue and brain tissue, spinal cord tissue, pituitary tissue, and eye tissue. In some cases, the compounds and compositions of the present invention can be used to reduce the prion population according to the method described in U.S. Patent No. 7470655, the contents of which are attached hereto by reference.

Antimicrobial compounds can also be used in food and plant species to reduce surface microbial populations; in manufacturing or processing facilities that handle food and plant species; or in the treatment of process water around these facilities. For example, the compounds can be used in food conveyor lines (such as belt sprays); boot and hand dipping containers; food storage facilities; anti-spoilage air circulation systems; refrigeration and cooling equipment; beverage coolers and heaters; blanchers, cutting boards, third sink areas, and devices for chilling or scalding meats. The compounds of the invention can be used to treat water from the transport of agricultural products, such as those found in chutes, pipeline transport, cutters, slicers, bleachers, retort systems, washers, and the like. Specific food products that can be treated with the compounds of the invention include eggs, meats, seeds, leaves, fruits, and vegetables. Specific plant surfaces include leaves, roots, seeds, bark, stalks, stems, tubers, underground stems, fruits, and similar harvested and growing plants. The compounds can also be used to treat animal carcasses to reduce pathogenic or non-pathogenic microbial levels.

Antimicrobial compounds can also be used for wastewater treatment, where both their antimicrobial function and their oxidizing properties can be utilized. In addition to the microbial issues surrounding wastewater, it is often rich in foul-smelling compounds of reduced sulfur, nitrogen, or phosphorus. A strong oxidant, such as the present invention, efficiently converts these compounds to their odorless derivatives, for example, sulfates, phosphates, and amine oxides. These same properties are very useful in the paper and pulp industry, where the bleaching property is also of great utility.

In some respects, the compounds of the present invention can be used for epoxidations. The polymer industry is a large consumer of peracids, especially peroxyacetic acid, but normal equilibrium peroxyacetic acid also includes some strongly acidic residues that are problematic for epoxide derivatives. Therefore, a stable peracid isolate is potentially of great use in this sector.

In some respects, the compounds and compositions of the present invention are useful for cleaning or sanitizing containers, processing facilities, or equipment in the food service or food processing sectors. The compounds and compositions have particular value for use in food packaging materials and equipment, and especially in aseptic cold or hot packaging. Examples of processing facilities in which the compound of the invention can be employed include dairy milk lines, continuous brewing systems, food processing lines such as food pumping systems and beverage lines, etc. Food service utensils can be disinfected with the compound of the invention. For example, the compounds can also be used in dishwashers, low-temperature dishwashers, tableware, bottle washers, bottle coolers, heaters, third sink washers, cutting areas (e.g., knives, slicers, cutters, and saws), and egg washers. Specific treatable surfaces include packaging, such as boxes, bottles, films and resins; tableware, such as glasses, plates, utensils, pots and pans; dishwashers and low-temperature dishwashers; exposed surfaces in the food preparation area, such as sinks, countertops, tables, floors and walls; Processing equipment, such as tanks, vats, lines, pumps and hoses (e.g., milk, cheese, ice cream and other dairy processing equipment); and transport vehicles. Containers include glass bottles, PVC or polyolefin film bags, cans, polyester, PEN or PET bottles of various volumes (100 ml to 2 liters, etc.), 3.7 l (1 gallon) milk containers, paper cartons for juice or milk, etc.

The compounds and compositions can also be used in other industrial equipment and in other industrial process flows, such as heaters, cooling towers, boilers, retort water, rinse water, aseptic packaging wash water, and the like. The compounds can be used to treat microbes and odors in recreational waters, such as swimming pools, spas, slides, water slides, fountains, and the like.

A filter containing this compound can reduce the population of microorganisms in the air and in liquids. This filter can remove waterborne and airborne pathogens, such as Legionella.

These compounds can be used to reduce the population of microbes, fruit flies, or other insect larvae in a drain or other surface.

The compounds of the present invention can also be used by food processing equipment by immersion in the solution of use, immersing the equipment for a sufficient time to sanitize the equipment, cleaning or draining the excess solution out of the equipment. The compound can also be used for spraying or cleaning food processing surfaces with the working solution, keeping the surfaces moist long enough to sanitize them and removing excess solution by wiping, vertical drainage, vacuuming, etc.

The compounds of the present invention can also be used in a method of sanitizing hard surfaces, such as institutional-type equipment, utensils, dishes, health service equipment or instruments, and other hard surfaces.

Antimicrobial compounds can be applied to microbes or to soiled or clean surfaces using various methods. These methods can operate on an object, surface, body, or stream of water or gas, or similar, by bringing the object, surface, body, or stream into contact with a compound of the invention. Contact can include any of numerous compound application methods, such as spraying the compound, immersing the object in the compound, treating the object with the compound in foam or gel form, or a combination thereof.

A concentrate or use concentration of a compound of the present invention can be applied or brought into contact with an object by any conventional method or apparatus for applying antimicrobial or cleaning compounds to an object. For example, it is possible to clean, spray, foam, and/or immerse the object in the compound, or in a use solution thereof. The compound can be sprayed, applied as a foam, or passed over the surface; the compound can be flowed over the surface, or the surface can be immersed in the compound. Application can be manual or by machine. Food processing surfaces, food products, food processing or transport water, and the like may be treated with stabilized compounds in liquid, foam, gel, aerosol, gas, wax, solid, or powder form, according to the invention, or with solutions of these compounds.

Laundry applications

In some respects, the compounds can also be used to sanitize items, such as fabrics, that have been contaminated. The items are placed in contact with the compounds of the invention at operating temperatures in the range of about 4°C to 80°C, for a period effective for their sanitization, disinfection and/or sterilization. In some cases, the compounds of the present invention can be used to bleach and/or sanitize items at a temperature of about 30°C to 50°C or about 40°C. In certain cases, the compounds of the present invention can be injected into the wash or rinse water of a washing machine and placed in contact with the contaminated fabric for a sufficient time to sanitize it. In other cases, the contaminated fabric is placed in contact with the compounds and compositions of the present invention for about 5 to 30 minutes. Excess solution can be removed by rinsing or spinning the fabric.

In some respects, the compounds of the present invention can be used as a bleaching agent to whiten, lighten, or remove stains from a substrate, for example, a hard surface or fabric. The compounds of the present invention can be used to lighten or remove stains from any conventional textile, including, but not limited to, cotton, cotton-polyester blends, wool, and polyester. The compounds of the present invention are also textile-tolerant, meaning they will not substantially degrade the fabric to which they are applied. The compounds of the present invention can be used to remove a variety of stains from diverse sources, including, but not limited to, lipstick, pigment/tallow, pigment/lanolin, rust, olive oil, mineral oil, motor oil, blood, makeup, red wine, tea, ketchup, and combinations thereof.

In some cases, the compounds of the present invention can be used as an acidic and low-odor bleaching agent. In certain cases, the compounds of the present invention can be used as a low-odor bleaching agent at a neutral pH, i.e., around 7. In others, the compounds of the present invention can be used at an alkaline pH, such as 8, 9, or 10. The compounds of the present invention can also be used as a complete product: acid, bleach, and sterilizing agent.

The compounds and compositions of the present invention can be used alone to treat items, such as textiles, or they can be used in conjunction with conventional detergents suitable for the items to be treated. The compounds and compositions of the invention can be used with conventional detergents in various ways, for example, they can be formulated with a conventional detergent. In other cases, the compounds and compositions of the invention can be used to treat the article as a separate additive from conventional detergent. When used as a separate additive, the compounds and compositions of the present invention can come into contact with the article to be treated at any time. For example, the compounds and compositions of the invention can come into contact with the article before, after, or essentially simultaneously with the contact of the items with the selected detergent.

In some cases, when used as a bleaching and/or sanitizing/disinfecting agent in laundry applications, a compound or mixture of compounds of the present invention will be present in a composition of about 5 ppm to 1,000 ppm. In others, when used as a bleaching and/or sanitizing/disinfecting agent in laundry applications, a compound or mixture of compounds of the present invention will be present in a composition of about 25 ppm to 100 ppm. In other situations, when used as a bleaching and/or sanitizing/disinfecting agent in laundry applications, a compound or mixture of compounds of the present invention will be present in a composition of about 20, 40, 60 or 80 ppm. In others, a compound or mixture of compounds of the present invention itself will be used as a bleaching agent, i.e., the compound or mixture of compounds will be present in a composition of about 100% by weight.

On-site cleaning

Other hard surface cleaning applications for the compounds of the present invention include clean-in-place (CIP) systems, off-site cleaning (COP) systems, washing machine decontaminators, sterilizers, textile washing machines, ultra- and nanofiltration systems, and indoor air filters. COP systems can include easily accessible systems, including wash tanks, immersion containers, mop buckets, holding tanks, sanitizing sinks, vehicle parts washers, non-continuous batch systems and washers, and the like. CIP systems include the internal components of tanks, lines, pumps, and other processing equipment generally used to process liquid product streams, such as beverages, milk, and juices.

In general, the actual cleaning of the system or other surface on-site (i.e., the removal of unwanted debris found on them) is performed with a different material, such as a formulated detergent that is applied with heated water. After this cleaning step, the instant composition should be applied or introduced into the system at a concentration of the solution to be used in unheated water, at room temperature. CIP typically employs flow rates on the order of about 40 to 600 liters per minute, from ambient temperatures up to about 70 °C and contact times of at least about 10 seconds, for example, about 30 or 120 seconds. The present composition can remain in solution in cold water (e.g., 4 °C/40 °F) or heated water (e.g., 60 °C/140 °F). Although heating the aqueous solution of the present composition is not normally necessary, in some circumstances heating may be desirable to improve its action. These materials are useful at any conceivable temperature.

A method for sanitizing fixed processing facilities on-site includes the following steps. The solution of use of the invention is introduced into the processing facilities at a temperature in the range of 4 °C to 60 °C. After the introduction of the solution of use, it is kept in a container or applied throughout the system for a sufficient time to sanitize the processing facilities (e.g., to kill undesirable microorganisms). After the surfaces have been sanitized using this composition, the solution is drained. After the sanitization step is complete, the system can optionally be rinsed with other materials, such as potable water. The composition can be applied to processing facilities for 10 minutes or less.

The present method may include delivering the present composition by supplying air for cleaning on-site or other surfaces, such as those inside pipes and tanks. This method of supplying air may reduce the required volume of solution.

Contacting a food product with sulfoperoxycarboxylic acid compounds. In some respects, the present invention provides methods for contacting a food product with a sulfoperoxycarboxylic acid compound or composition using any method or apparatus suitable for the application of that compound or composition. For example, in some cases, the food product is brought into contact with a compound of the present invention by means of spraying, immersion, or treatment in the form of a foam or gel. Contact with a spray, foam, gel, or through immersion can be achieved in various ways known to persons qualified to apply antimicrobial agents to food. Contact with the food product can occur in any location where the product may be found, such as a field, processing plant or factory, vehicle, warehouse, store, restaurant, or home. These same methods can also be adapted to apply the compounds of the present invention to other objects.

Present methods require a minimum contact time of the compound with the food product for a significant antimicrobial effect to occur. The contact time may vary depending on the concentration, application method, and temperature of the compound used, and on the amount of dirt and microorganisms in the food product, the type of antimicrobial agent, or similar factors. The exposure time may be at least 5 to 15 seconds. In some cases, the exposure time is about 15 to 30 seconds. In others, the exposure time is at least about 30 seconds.

In certain situations, the food product washing method employs a pressure spray that includes a compound of the present invention. During the application of the spray solution to the food product, its surface can be moved by mechanical action, for example, agitated, rubbed, brushed, etc. This agitation can occur through physical rubbing of the food product, by the action of the spray solution under pressure, through sonication, or other methods. Agitation increases the effectiveness of the spray solution in killing microorganisms; one reason for this may be better exposure of the solution to crevices or small colonies containing microorganisms. To increase effectiveness, the spray solution can also be heated to a temperature of about 15 to 20 °C before application, for example, from about 20 to 60 °C. The stabilized spray compound can be left on the food product for a sufficient time to adequately reduce the population of microorganisms and then rinsed, drained, or evaporated from the product.

The application of the material by spraying can be carried out using a manual spray wand, an automatic food product sprayer that moves along a production line using multiple spray heads to ensure complete contact, or by another spraying device. An automatic spray application involves the use of a spray booth. The spray booth basically confines the sprayed compound to the interior of the booth. The production line moves the food product through the spray booth entrance, where the food is sprayed onto all its external surfaces with sprays located inside the booth. After the food product is fully covered by the material, this material is drained back into the booth. Then, the food product can exit the booth. The spray booth may include steam jets used to apply the stabilized compounds of the invention. These steam jets can be used in combination with cooling water to ensure that the treatment reaching the surface of the food product is below 65°C, for example, below 60°C. The temperature of the spray on the food product is important to ensure that it is not substantially altered (cooked) by the spray temperature. The spray pattern can be virtually any useful pattern.

Immersion of a food product in a stabilized liquid compound of the present invention can be achieved by a variety of methods known to qualified persons. For example, the food product can be placed in a tank or tub containing the stabilized compound. Alternatively, the food products can be transported or processed in a chute containing the stabilized compound. The washing solution can be agitated to increase its effectiveness and the speed at which it reduces microorganisms accompanying the food product. Agitation can be achieved by conventional methods, including ultrasound, aeration via bubbling air through the solution, mechanical methods such as sieves, paddles, brushes, pump-driven liquid jets, or combinations of these methods. The washing solution can be heated to increase its effectiveness in killing microorganisms. After the food product has been immersed for a sufficient time to achieve the desired antimicrobial effect, it can be removed from the tub or trough, and the stabilized compound can be rinsed, drained, or evaporated from the food product.

In other cases, a food product may be treated with a foam version of the compound of the present invention. The foam may be prepared by mixing foam surfactants with the washing solution at the time of use. The foam surfactants may be non-ionic, anionic, or cationic in nature. Examples of useful types of surfactant include, but are not limited to, the following: alcohol ethoxylates, alcohol ethoxylate carboxylates, amine oxides, alkyl sulfates, alkyl ether sulfates, sulfonates, including, for example, alkylaryl sulfonates, quaternary ammonium compounds, alkyl sarcosines, betaines, and alkylamides. Typically, foam surfactant is mixed with the washing solution at the time of use. The solution concentrations for foaming agents range from approximately 50 ppm to about 2.0% by weight. At the time of use, compressed air can be injected into the mixture, and then it can be applied to the surface of the food product using a foam application device, such as a tank foamer or a wall-mounted suction foamer.

In some cases, the food product may be treated with a thickened or gelled version of the compound of the present invention. In the thickened or gelled state, the washing solution remains in contact with the surface of the food product for longer periods, thus increasing its antimicrobial effectiveness. The thickened or gelled solution also adheres to vertical surfaces. The compound or washing solution can be thickened or gelled using existing technologies such as xanthan gum, polymeric thickeners, cellulosic thickeners, or similar. Rod micelle-forming systems, such as amine oxides and anionic counterions, can also be used. Thickening or gelling agents can be used in the concentrated product or in mixtures with the washing solution at the time of use. Typical usage levels of thickening or gelling agents range from about 100 ppm to about 10% by weight.

Processing methods for beverages, food, and pharmaceutical products.

The sulfoperoxycarboxylic acid compounds of the present invention can be used in the manufacture of beverages, foods and pharmaceutical products, including fruit juice, dairy products, malt drinks, soy-based products, yogurts, baby food, bottled water products, teas, cough medicines, medications and soft drinks. The compounds of the present invention can be used to sanitize, disinfect, act as a sporicide, or sterilize bottles, pumps, lines, tanks, and mixing equipment used in the manufacture of such beverages. Furthermore, the sulfoperoxycarboxylic acid antimicrobial compounds of the present invention can be used in aseptic cold filling operations where the interior of the food, beverage, or pharmaceutical container is sanitized or sterilized prior to filling. In these operations, a container can be brought into contact with the disinfectant sulfoperoxycarboxylic acid compound, typically using a spray, immersion, or filling device to bring the inside of the container into contact with the sulfoperoxycarboxylic acid compound for a period sufficient to reduce the populations of microorganisms within the container. The container can then be emptied, removing the amount of disinfectant or sterilizing agent used. After emptying, the container can be rinsed with potable water or sterilized and emptied again. After rinsing, the container can be filled with the beverage, food, or pharmaceutical product. The container can then be sealed, capped, or closed and then packaged for shipment and final sale. The sealed container can be placed in an autoclave or retort to further kill microorganisms.

In the manufacture of food, beverages, or pharmaceutical products, fungal microorganisms of the genus Chaetomium or Arthrinium, and spores or bacteria of the genus Bacillus spp. can be a major problem in bottling processes, especially in aseptic cold bottling processes. The sulfoperoxycarboxylic acid compounds of the present invention can be used to control or significantly reduce (reduction of more than 5 log) these microorganisms.₀) the number of Chaetomium, Arthrinium, or Bacillus microorganisms in bottling lines for beverages, food, or pharmaceutical products using aseptic cold bottling techniques.

In these techniques, it is possible to fill aluminum or steel metal cans, glass bottles or containers, plastic bottles (PET, PBT or PEN) or similar, using aseptic cold filling techniques. In these processes, the sulfoperoxycarboxylic acid materials of the invention can be used to sanitize the interior of beverage containers before filling with carbonated or non-carbonated beverage. Typical carbonated beverages in this application include, but are not limited to, cola drinks, fruit drinks, ginger ale, root beer, iced tea (which may be non-carbonated), and other common beverages considered soft drinks. The sulfoperoxycarboxylic acid materials of the invention can be used to sanitize tanks, lines, pumps, and other equipment used for the manufacture and storage of soft drink material, and also used in bottling or in containers of the beverages. In certain cases, sulfoperoxycarboxylic acid disinfectants are useful for killing bacteria, fungi, and fungal microorganisms that may be present on the surfaces of production equipment and beverage containers.

The sulfoperoxycarboxylic acid compounds of the present invention can effectively kill microorganisms (e.g., reduction > 1 log).₁₀ up to about 5 log₁₀ within 30 seconds) from a concentration level of at least about 50 ppm, for example, about 150, 500 or 1,000 ppm of a sulfoperoxycarboxylic acid compound. In a given case, the sulfoperoxycarboxylic acid compound, except for water, would be present at a concentration of about 0.001 to 1% by weight, for example, about 0.01 to 0.15% by weight or about 0.05 to 0.1% by weight.

All acid, salt, base, and other ionic and non-ionic forms of the compounds described are included as compounds of the invention. For example, if a compound is shown as an acid in this document, the salt forms of the compound are also included. Similarly, if a compound is shown as a salt, the acid and/or base forms are also included.

Qualified individuals in this field will recognize, or be able to determine through the use of, at most, routine experimentation, various equivalents to the specific procedures, cases, statements, and examples described in this document. These equivalents are considered to be within the scope of the invention and are covered by the statements appended to this document. The content of all references, patents, and patent applications cited throughout this application is incorporated herein for reference. The invention is further illustrated by the following examples, which should not be construed as limiting.

EXAMPLES

Some of the following examples were performed using a sulfonated peroleic acid product. Without wishing to be bound to any particular theory, it is believed that the peracid formed from a commercially available sulfonated oleic acid starting material includes a mixture of compounds of the present invention. This is believed to be due, in part, to the nature of the sulfonated oleic acid starting material. In other words, it is believed that, since the initial material of sulfonated oleic acid is derived from natural sources, it is not chemically pure, that is, it does not contain only one form of sulfonated oleic acid. Thus, without wishing to be bound to any particular theory, it is believed that the sulfonated peroleic acid (hereinafter referred to as the “sulfonated peroleic acid product”) used in these examples included a mixture of about 20 to 25% by weight of Compound A (10-hydroxy-9-sulfooctadecaneperoxoic acid), about 20 to 25% by weight of Compound N (10,11-dihydroxy-9-sulfooctadecaneperoxoic acid), Approximately 20 to 25% by weight of Compound I (9-hydroxy-10-sulfooctadecaneperoxoic acid) and approximately 20 to 25% by weight of Compound O (8,9-dihydroxy-10-sulfooctadecaneperoxoic acid). The remainder of the peracid composition is believed to comprise approximately 5 to 10% by weight of a mixture of these compounds.

Example 1 - Use of a sulfoperoxycarboxylic acid as a coupler under high-level disinfection application conditions.

Stability experiments with peroxyoctanoic acid (POOA) were performed under high-level disinfection (HLD) conditions to evaluate the stability of a composition of the present invention that included a sulfonated peroleic acid product compared to known and commercially available disinfectants.

Octave FS®, a product containing peroxyoctanoic acid, commercially available from Ecolab Inc., was tested in comparison with Formulas A, B, and C, and their mixtures. Formula A was a mixture of: 2.5% by weight of Dequest 2010 (commercially available from thermPhos), peracid grade; 61% by weight of hydrogen peroxide (35%); 2.50% by weight of sulfuric acid (98%); 6.0% by weight of octanoic acid; 19% by weight of Hostapur SAS (40%) (commercially available from Clariant); and 9.00% by weight of SXS-40 (commercially available from Stepan Company). Formula B was a mixture of approximately 20% by weight of the product of sulfonated peroleic acid, approximately 10% of peroctanoic acid, approximately 15% by weight of octanoic acid, and approximately 0.5% by weight of hydrogen peroxide. Formula C was a mixture of approximately 25% by weight of sulfonated peroleic acid and approximately 0.50% by weight of hydrogen peroxide. Mixtures of formulas A, B, and C were also tested. The test solutions were diluted with DL water to compose a solution with approximately 1,000 ppm of POOA present at a pH of approximately 6.5. The table below shows the five solutions tested and the amount of sulfonated peroleic acid product, POOA, and hydrogen peroxide available, in ppm, in each of the tested solutions.

Table 2.

<td></td><td colspan="5">Test solution composition</td>

<td></td><td> #1</td><td> #2</td><td> #3</td><td> #4</td><td> #5</td>

<td>Octave FS® (% of weight)</td><td> 10.00</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td>

<td>Formula A (% of weight)</td><td> 0</td><td> 4.2</td><td> 0</td><td> 0</td><td> 0</td>

<td>Formula B (% of weight)</td><td> 0</td><td> 0</td><td> 0.88</td><td> 0.55</td><td> 0.33</td>

<td>Formula C (% of weight)</td><td> 0</td><td> 0</td><td> 0.22</td><td> 0.55</td><td> 0.77</td>

<td>Final weight, with added water dl (g)</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td><td> 100</td>

<td>Product of sulfonated pearloleic acid (ppm)</td><td> 0</td><td> 0</td><td> 2318</td><td> 2459</td><td> 2554</td>

<td>POOA (ppm)</td><td> 1000</td><td> 1000</td><td> 800</td><td> 500</td><td> 300</td>

<td>H₂THE₂</td><td> 8050</td><td> 8928</td><td> 55</td><td> 55</td><td> 55</td>

The samples were stored at 40 °C and the amount of POOA present was measured by high-performance liquid chromatography at selected times. The following table shows the HPLC analysis results for the samples at various times.

Table 3.

<td></td><td colspan="5">Test solution</td>

<td></td><td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td>

<td>Time (hours)</td><td>POOA (ppm)</td><td>POOA (ppm)</td><td>POOA (ppm)</td><td>POOA (ppm)</td><td>POOA (ppm)</td>

<td> 0</td><td> 490</td><td> 870</td><td> 700</td><td> 470</td><td> 290</td>

<td> 6</td><td> 310</td><td> 730</td><td> 590</td><td> 400</td><td> 250</td>

<td> 24</td><td> 0</td><td> 120</td><td> 350</td><td> 240</td><td> 150</td>

<td> 48</td><td> 0</td><td> 10</td><td> 240</td><td> 160</td><td> 100</td>

<td> 72</td><td> 0</td><td> 0</td><td> 180</td><td> 130</td><td> 80</td>

<td>9 days</td><td> 0</td><td> 0</td><td> 20</td><td> 0</td><td> 0</td>

These results are also graphically represented in Figure 1. As can be seen in the table above, and in Figure 1, the test solutions, including a compound of the present invention, namely test solutions 3, 4 and 5, lost less POOA over the first 24 hours compared to the other two test solutions. Even after 48 hours, a greater amount of POOA remained in the test solutions that included a compound of the present invention compared to the other solutions tested. For each of the test solutions that included a compound of the present invention, it was demonstrated that the loss of POOA in the solutions was not linear, and that the rate of POOA decomposition was drastically reduced at higher proportions of the sulfonated peroleic acid product to POOA.

Another stability study was conducted to evaluate the stability of a composition of the present invention at an elevated temperature, namely 37.7 °C (100 °F). A solution was used that included approximately 2% by weight of the sulfonated peroleic acid product and approximately 55% by weight of H₂THE₂, among other ingredients. The amount of the product of sulfonated peroleic acid and H₂THE₂ The activity was measured over 48 days. The results are shown in Figure 2. As can be seen in this figure, the peracid compound, the product of sulfonated peroleic acid, maintained its activity throughout the assay, even at this accelerated temperature.

Another stability study was conducted to evaluate the stability of peroxyoctanoic acid when in contact with a compound of the present invention, namely, the sulfonated peroleic acid product, under ambient conditions. For this study, the pH was consistently around 6 to 6.5. Three different formulas were tested for this study: Formula D included approximately 5 grams of a mixture of sulfonated peroleic acid, peroxyoctanoic acid, hydrogen peroxide, and sodium cumene sulfate, among other ingredients; Formula E included approximately 0.5 g of a mixture of sulfonated peroleic acid and peroxyoctanoic acid; and Formula F included Octave®, commercially available from Ecolab Inc. The amount of active peroxyoctanoic acid available at various times over 15 days was measured. The results are shown in the table below.

Table 4.

<td></td><td>Formula D</td><td>Formula E</td><td>Formula F</td>

<td>Time (days)</td><td>POOA (ppm)</td><td>POOA (ppm)</td><td>POOA (ppm)</td>

<td> 0</td><td> 590</td><td> 640</td><td> 570</td>

<td> 1</td><td> 550</td><td> 590</td><td> 500</td>

<td> 4</td><td> 470</td><td> 480</td><td> 360</td>

<td> 6</td><td> 420</td><td> 400</td><td> 240</td>

<td> 8</td><td> 410</td><td> 360</td><td> 160</td>

<td> 11</td><td> 360</td><td> 270</td><td> 70</td>

<td> 14</td><td> 310</td><td> 230</td><td> 30</td>

These results are also graphically represented in Figure 3. As can be observed in this table and in the figure, the formulas that included a compound of the present invention, namely Formulas D and E, maintained a higher level of POOA over 15 days. Thus, without wishing to be bound to any particular theory, it is believed that the addition of a composition that includes the compounds of the present invention acts to stabilize other percarboxylic acids present in the composition.

Example 2 - Use of a sulfoperoxycarboxylic acid as a bleaching agent

The use of a compound of the present invention as a bleaching agent was evaluated. The stain removal ability of the cleaning composition was determined by washing with artificially stained fabric samples. The stained samples were purchased from a manufacturer or distributor (e.g., Test Fabrics, Inc., West Pittston, Pa., USA). Types of stains, such as olive oil, sebum, makeup, and wine, are characteristic of natural stains found in laundry applications.

The stained samples were washed with the cleaning composition in a device such as the Terg-o-tometer (United States Testing Co., Hoboken, NJ, USA). The Terg-o-tometer is a laboratory washing device consisting of several pots placed in a single water bath at a controlled constant temperature, with suspended stirrers and time and speed control. The wash test parameters included: wash temperature, wash duration, pH, mechanical agitation, cleaning composition dose, water hardness, washing formula, and cloth/liquid ratio. After completing the appropriate exposure times, the fabric samples were removed. The test chemicals were immediately discharged, and the samples were rinsed with cold synthetic water with a hardness of 5 until 5 fill and rinse cycles were completed. The samples were then placed on a flat surface and dried overnight on white cotton-polyester towels before reflectance readings were taken using a spectrophotometer, such as the Hunter ColorQuest XE (reflectance).

To determine the percentage (%) of stain removal (SR), for example, the bleaching capacity, the reflectance of the fabric sample was measured in a spectrophotometer. The “L value” is a direct reading provided by the spectrophotometer. L is generally indicative of a broad spectrum of visible reflectance, where a value of 100% would be absolute white. The stain removal percentage is calculated by the difference between the initial lightness value (L) (before washing) and the final L value (after washing):

SR= ((LfjnarL initial)/(9®4- initial))x100%

A bleaching test was conducted comparing a composition that included a sulfonated peroleic acid product with the following commercially available bleaching/cleaning compositions: Ozonit® and Oxysan®, provided by Ecolab Inc. Ozonit® represents a product with 4.5% peroxyacetic acid, while Oxysan® represents a product with 0.6% peroxyoctanoic acid. Formula A was a composition that included approximately 2% by weight of sulfonated peroleic acid, approximately 5% by weight of peroxyacetic acid, and approximately 1.5% by weight of peroxyoctanoic acid. Formula A was used at a concentration of 1,200 ppm and subsequently treated in two of the three cases with additional acetic acid to produce test solutions with reduced pH. Ozonit® was used at a concentration of 2,000 ppm. Oxysan® was tested at concentrations of 1,272 and 2,545 ppm. All washing solutions were additionally treated with Detergent MP® and TurboCharge II®, both provided by Ecolab Inc., and used at 500 and 750 ppm, respectively. The bath/wash temperature was maintained at 37.7 °C (100 °F). Detergent MP® and TurboCharge II provide a common alkaline accumulator detergent base. The bleaching test results are shown in the table below.

Table 5.

<td></td><td>Stain removal (%) from cotton</td><td></td><td></td><td>Cone, of bleach</td><td></td>

<td>Type of bleach</td><td>Tea</td><td>Red wine</td><td>Ketchup</td><td>(mg/l)</td><td>pH</td>

<td>Ozonit ®</td><td> 29</td><td> 59</td><td> 27</td><td> 2000</td><td> 9.50</td>

<td>Oxysan®</td><td> 21</td><td> 66</td><td> 19</td><td> 1272</td><td> 8.00</td>

<td>1X Oxysan®</td><td> 33</td><td> 69</td><td> 27</td><td> 2545</td><td> 8.00</td>

<td>Formula A, pH 8.0</td><td> 37</td><td> 73</td><td> 38</td><td> 1000</td><td> 8.00</td>

<td>Formula A, pH 8.5</td><td> 38</td><td> 72</td><td> 41</td><td> 1000</td><td> 8.50</td>

<td>Formula A, pH 9.0</td><td> 34</td><td> 69</td><td> 36</td><td> 1000</td><td> 9.00</td>

As can be seen in this table, the Formula A compositions achieved a higher percentage of stain removal than the commercially available solutions tested at all pH levels, especially in the case of ketchup, which is a hydrophobic stain.

Formula A was also tested using a full wash cycle bleaching test. The test was performed with a 15 kg (35 lb) commercial side-loading washing machine (UniMac UX35PVXR). Pre-stained test sheets with multiple panels (Ecomon No. 1 &amp; Ecomon No. 4 included 14 bleachable stained panels and 12 non-bleachable pigment stained panels) were added to the empty washing machine before starting a 20-minute wash program (typically at 40°C). The chemicals were added in a staggered sequence of 5 x 30 seconds via the suspended dispensing cups after the machine was filled with

I. Soft synthetic water of hardness 5. The initial chemical was added with the alkaline detergent product (approximately 84 g of Turboemulsion, commercially available from Ecolab Inc.). Then, the bleaching chemical was added approximately 30 seconds after the caustic surfactant mixture and a 20-minute wash cycle was started. 10 After the wash cycle, the machine was drained and 3 rinse cycles were run.

The leaves were removed and naturally dried at 21 °C (70 °F) overnight before measuring the reflectance of each sample panel with a Hunter ColorQuest XE spectrophotometer (reflectance) (UV filter ΊN”). The results are shown in the table below.

Table 6.

<td></td><td colspan="4">Reflectance values ​​L</td><td colspan="2">⁵Stain removal, %</td>

<td></td><td>Initial sample stained</td><td>³Turboemulsion only</td><td>TE +⁶Formula A</td><td>TE + Ozonit</td><td>TE + Formula THE</td><td>TE + Ozonit</td>

<td>Stains that can be bleached</td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>Tea in AL</td><td> 80.64</td><td> 80.67</td><td> 91.62</td><td> 88.94</td><td> 71.48</td><td> 54.01</td>

<td>Tea in POL/AL</td><td> 80.43</td><td> 79.24</td><td> 91.17</td><td> 88.28</td><td> 68.96</td><td> 50.40</td>

<td>Red wine in AL</td><td> 73.66</td><td> 85.94</td><td> 93.03</td><td> 92.06</td><td> 86.72</td><td> 82.36</td>

<td>Red wine in POL/AL, old</td><td> 73.82</td><td> 82.98</td><td> 91.71</td><td> 90.67</td><td> 80.67</td><td> 75.97</td>

<td>Coffee in AL</td><td> 78.92</td><td> 90.72</td><td> 93.10</td><td> 92.70</td><td> 83.04</td><td> 80.70</td>

<td>Coffee in POL/AL</td><td> 79.77</td><td> 92.27</td><td> 93.62</td><td> 93.28</td><td> 85.34</td><td> 83.26</td>

<td>Blackcurrant juice in AL</td><td> 64.40</td><td> 88.37</td><td> 93.54</td><td> 92.82</td><td> 92.22</td><td> 89.94</td>

<td>Blackcurrant juice in POL/AL</td><td> 63.57</td><td> 85.02</td><td> 93.30</td><td> 92.07</td><td> 91.68</td><td> 87.89</td>

<td>Blood in AL</td><td> 46.25</td><td> 89.51</td><td> 90.60</td><td> 91.48</td><td> 89.14</td><td> 90.91</td>

<td>IEC 456, old</td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>Blood in AL IEC 456, recent</td><td> 49.36</td><td> 93.06</td><td> 93.81</td><td> 93.88</td><td> 95.30</td><td> 95.45</td>

<td>Blood/Milk/Ink in AL</td><td> 45.26</td><td> 61.00</td><td> 51.10</td><td> 51.89</td><td> 11.51</td><td> 13.06</td>

<td>Cocoa in AL IEC 456, recent</td><td> 75.22</td><td> 83.76</td><td> 83.47</td><td> 83.27</td><td> 39.72</td><td> 38.74</td>

<td>Blood/Milk/Rust in AL</td><td> 58.87</td><td> 86.37</td><td> 69.87</td><td> 70.54</td><td> 29.62</td><td> 31.44</td>

<td>Egg/Rust in AL</td><td> 62.87</td><td> 76.36</td><td> 76.09</td><td> 75.81</td><td> 39.89</td><td> 39.05</td>

<td>average /14</td><td> 66.65</td><td> 83.95</td><td> 86.15</td><td> 85.55</td><td> 68.95</td><td> 65.23</td>

<td>Stains that cannot be bleached</td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>Pigment/Lanolin in AL</td><td> 71.98</td><td> 80.90</td><td> 78.63</td><td> 80.55</td><td> 27.70</td><td> 35.68</td>

<td>Pigment/Lanolin in POL/AL</td><td> 66.65</td><td> 82.38</td><td> 73.28</td><td> 81.72</td><td> 22.60</td><td> 51.35</td>

<td>Pigment/Sebum in AL</td><td> 73.19</td><td> 87.70</td><td> 84.02</td><td> 86.76</td><td> 47.49</td><td> 59.48</td>

<td>Pigment/Tallow in POL/AL</td><td> 70.64</td><td> 87.97</td><td> 77.82</td><td> 86.74</td><td> 28.33</td><td> 63.49</td>

<td>Rust/Olive oil in AL</td><td> 47.93</td><td> 69.90</td><td> 62.45</td><td> 64.87</td><td> 30.21</td><td> 35.23</td>

<td>Rust/Olive oil in POL/AL</td><td> 40.77</td><td> 62.89</td><td> 56.23</td><td> 58.57</td><td> 27.99</td><td> 32.23</td>

<td>Rust/Mineral oil in AL</td><td> 59.76</td><td> 72.35</td><td> 68.93</td><td> 71.80</td><td> 25.30</td><td> 33.21</td>

<td>Rust/Mineral oil in POL/AL</td><td> 55.62</td><td> 80.15</td><td> 73.89</td><td> 78.78</td><td> 45.25</td><td> 57.36</td>

<td>Used motor oil in AL</td><td> 65.91</td><td> 73.06</td><td> 70.99</td><td> 71.77</td><td> 16.89</td><td> 19.47</td>

<td>Used motor oil in POL/AL</td><td> 61.10</td><td> 68.27</td><td> 64.08</td><td> 66.01</td><td> 8.53</td><td> 14.08</td>

<td>Makeup in AL</td><td> 84.81</td><td> 90.06</td><td> 89.50</td><td> 90.14</td><td> 41.94</td><td> 47.63</td>

<td>Makeup in POL/AL</td><td> 85.16</td><td> 92.57</td><td> 91.91</td><td> 92.14</td><td> 62.24</td><td> 64.42</td>

<td>average /12</td><td> 70.85</td><td> 86.01</td><td> 81.49</td><td> 84.62</td><td> 32.04</td><td> 42.80</td>

Notes: 3. Turbo Usona is a commercially available, complete emulsion of alkali metal chelators emulsified with a surfactant blend made by Ecolab, Inc. and was used in this test at 1750 ppm. 4. Ozonit Super is a peracetic acid and hydrogen peroxide disinfectant/bleach used at a concentration of 2000 ppm. Ozonit is a mixture of peracetic acid and hydrogen peroxide made by Ecolab, Inc. 5 The stain removal percentage was calculated using the following formula: SR = ((Lfinal-Lincial)/(96-Lincial)) x 100% CO: Cotton; POL/AL: polyester and cotton blend

As can be seen in this table, Formula A, on average, provides superior bleaching to Ozonit®. Although the superiority in bleachable stains is only 3.7 points (5.4%), in the case of stains that are more resistant to removal by washing, such as tea, the difference was up to 17 points (24%).

Another complete wash test was conducted using a wash cycle (full-size side-loading washing machine), but instead of individual stained samples, this test used multi-panel sheets combining 14 stained, bleachable samples (Ecomon 4) and a second sheet combining 12 stained samples with pigment/hydrocarbon that cannot be bleached (Ecomon 1). These panels are custom-made for Ecolab by wfk Testgewebe GmbH of Bruggen, Germany. This extensive bleaching test utilized a design experiment that varied concentrations, sometimes simultaneously, with temperatures, etc. After the specified washing time was complete, all Ecomon sheets were thoroughly rinsed, dried, and their reflectivity under broad-spectrum light was measured, again with UV filtering to remove possible interference from optical glare effects. Unlike the data from the “tergotometer”, the percentage of stain removal was not calculated, but measured directly from the reflectance instrument (Minolta CM-2610d Spektrophotometer). A value “Y”, representing broad-spectrum reflectivity, was reported. The higher the “Y” value, the whiter the material and therefore the greater the bleaching or stain removal.

In this test, Formula A was compared to Ozonit®, Ozonit Super® (a product with 15% peroxyacetic acid provided by Ecolab), and Oxysan®, which were combined in various ways with the following commercially available alkaline buildup cleaners: Triplex Emulsion®, provided by Ecolab Inc.; Turbo Usona®, provided by Ecolab Inc.; Ozonit Super®, provided by Ecolab Inc.; and Oxysan®, provided by Ecolab Inc. The results are displayed in the tables below.

Table 7. Bleaching results

<td>Procedure</td><td>Tea in AL</td><td>Tea in POL/ AL</td><td>Red wine in AL, old</td><td>Red wine in POL/AL, former</td><td>Coffee in AL</td><td>Coffee in POL/ AL</td><td>Blackcurrant juice in AL</td><td>Blackcurrant juice in POL/AL</td><td>Average</td>

<td>1.5 ml/l of 2Triplex Emulsion + 1 ml/l of Formula A. Conditions: 15' 40°C</td><td> 72.7</td><td> 70.0</td><td> 75.4</td><td> 74.6</td><td> 80.2</td><td> 84.6</td><td> 82.5</td><td> 84.1</td><td> 78.0</td>

<td>1.5 ml/l of Triplex Emulsion + 2 ml/l of Formula A. Conditions: 15' 40°C</td><td> 80.6</td><td> 79.6</td><td> 82.5</td><td> 80.5</td><td> 83.5</td><td> 86.0</td><td> 85.5</td><td> 86.1</td><td> 83.0</td>

<td>1.5 ml/l of Triplex Emulsion + 2.5 ml/l of Formula A. Conditions: 20'</td><td> 82.6</td><td> 83.1</td><td> 84.3</td><td> 80.9</td><td> 84.3</td><td> 86.0</td><td> 86.2</td><td> 86.3</td><td> 84.2</td>

<td>40°C</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>1.5 ml/l of Triplex Emulsion + 1 ml/l of Ozonit Super Conditions: 10' 70 □</td><td> 78.5</td><td> 79.0</td><td> 82.2</td><td> 82.1</td><td> 84.8</td><td> 86.2</td><td> 86.7</td><td> 86.5</td><td> 83.3</td>

<td>4 ml/l³ Turbo Usona + 2 ml/l ^Ozonit Performance Conditions: 20' 40α</td><td> 80.8</td><td> 80.5</td><td> 81.5</td><td> 79.0</td><td> 81.1</td><td> 84.2</td><td> 82.0</td><td> 80.8</td><td> 81.2</td>

<td>4 ml/l Turbo Usona + 4 ml/l^sOxysan Conditions: 20' 400</td><td> 79.2</td><td> 77.9</td><td> 78.9</td><td> 76.3</td><td> 79.9</td><td> 83.3</td><td> 77.6</td><td> 75.9</td><td> 78.6</td>

<td>4 ml/l of Turbo Usona + 2 ml/l of Formula A Conditions: 15' 40α</td><td> 82.2</td><td> 81.7</td><td> 82.1</td><td> 80.5</td><td> 82.6</td><td> 85.2</td><td> 82.6</td><td> 82.6</td><td> 82.4</td>

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

<td>LSD</td><td> 1.8</td><td> 3</td><td> 1.9</td><td> 2.4</td><td> 1.1</td><td> 0.8</td><td> 1.7</td><td> 1.8</td><td> 1.9</td>

Table 8. Bleaching results

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

<td></td><td>1.5 ml/l of 2Triplex Emulsion + 1 ml/l of Formula A Conditions: 15' 40ü</td><td>1.5 ml/l of Triplex Emulsion + 2 ml/l of Formula A Conditions: 15' 40 α</td><td>1.5 ml/l of Triplex Emulsion + 2.5 ml/l of Formula A. Conditions: 20' 40D</td><td>1.5 ml/l of Triplex Emulsion + 1 ml/l of Ozonit Super Conditions: 10' 70 α</td><td>4 ml/l³ Turbo Usona + 2 ml/l⁴ Ozonit Performance Conditions: 20' 40α</td><td>4 ml/l Turbo Usona + 4 ml/lc_THEOxysan Conditions: 20' 40α</td><td>4 ml/l of Turbo Usona + 2 ml/l of Formula A Conditioner tions: 15' 400</td><td>LSD</td>

<td>Pigment/ Lanolin in AL</td><td> 54.3</td><td> 55.6</td><td> 56.8</td><td> 67.3</td><td> 57.5</td><td> 56.6</td><td> 54.8</td><td> 6.1</td>

<td>Pigment/Lanolin in POL/AL</td><td> 53.4</td><td> 51.4</td><td> 48.8</td><td> 60.6</td><td> 46.1</td><td> 44.9</td><td> 46.2</td><td> 5.8</td>

<td>Pigment/ Used bookstore in AL</td><td> 68.3</td><td> 59.7</td><td> 59.6</td><td> 67.5</td><td> 60.1</td><td> 58.0</td><td> 60.9</td><td> 6.7</td>

<td>Pigment/ Used bookstore in POL/AL</td><td> 66.0</td><td> 54.2</td><td> 54.7</td><td> 73.4</td><td> 53.2</td><td> 50.5</td><td> 54.3</td><td> 6.3</td>

<td>Rust/Olive oil in AL</td><td> 47.7</td><td> 42.5</td><td> 32.2</td><td> 46.9</td><td> 24.7</td><td> 25.1</td><td> 24.3</td><td> 7.8</td>

<td>Rust/Olive oil</td><td> 33.8</td><td> 28.5</td><td> 24.2</td><td> 38.4</td><td> 15.7</td><td> 14.4</td><td> 13.0</td><td> 9.6</td>

<td>olive in POL/AL</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>Rust/OIL the mineral in AL</td><td> 36.9</td><td> 34.3</td><td> 36.0</td><td> 34.0</td><td> 33.4</td><td> 30.6</td><td> 30.6</td><td> 4.5</td>

<td>Rust/Oil the mineral in POL/AL</td><td> 42.4</td><td> 43.9</td><td> 35.8</td><td> 46.6</td><td> 31.0</td><td> 32.7</td><td> 37.7</td><td> 8.2</td>

<td>Used motor oil in AL</td><td> 42.7</td><td> 43.9</td><td> 42.6</td><td> 46.0</td><td> 44.0</td><td> 44.9</td><td> 46.3</td><td> 2.6</td>

<td>Used motor oil in POL/AL</td><td> 37.7</td><td> 34.7</td><td> 33.7</td><td> 36.4</td><td> 32.2</td><td> 33.5</td><td> 33.8</td><td> 1.6</td>

<td>Makeup in AL</td><td> 75.3</td><td> 74.1</td><td> 75.7</td><td> 84.1</td><td> 73.3</td><td> 72.4</td><td> 73.5</td><td> 4</td>

<td>Makeup in POL/AL</td><td> 79.8</td><td> 77.9</td><td> 76.8</td><td> 86.6</td><td> 75.7</td><td> 74.0</td><td> 76.9</td><td> 3.8</td>

<td>Lipstick in AL</td><td> 87.6</td><td> 87.4</td><td> 87.3</td><td> 87.7</td><td> 85.9</td><td> 86.9</td><td> 87.3</td><td> 1.4</td>

<td>Lipstick in POL/AL</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td> 3.047 0618</td>

<td>Average</td><td> 53.2</td><td> 50.1</td><td> 48.1</td><td> 57.3</td><td> 45.6</td><td> 44.8</td><td> 46.0</td><td> 5.6</td>

Notes:

1. The Y value refers to the reflectance value calculated by the Minolta CM-2610d spectrophotometer.

It is very similar to the L value calculated by the spectrophotometers at Hunter Lab.

2. Triplex Emulsion is a commercially available, complete emulsion of alkali metal chelators emulsified with a surfactant blend manufactured by Ecolab, Inc. (Europe).

3. Turbo Usona is a commercially available, complete emulsion of alkali metal chelators emulsified with a surfactant blend manufactured by Ecolab, Inc. (Europe).

4. Ozonit Super is a peracetic acid and hydrogen peroxide disinfectant/bleach manufactured by Ecolab, Inc. (Europe).

5. Oxysan is a disinfectant/bleach containing peracetic acid and hydrogen peroxide, and also peroxyoctanoic acid, manufactured by Ecolab, Inc. (Europe).

AL: Cotton

POL/AL: polyester and cotton blend

As can be seen from these results, overall the samples washed with the compositions of the present invention, i.e., with Formula A, achieved similar bleaching compared to bleaching agents available on the market.

Example 3 - Use of a sulfoperoxycarboxylic acid as a bleaching agent

A bleaching test was performed comparing a composition that included a sulfoperoxycarboxylic acid of the present invention, namely 11sulfoundecaneperoxoic acid (Compound D), with the following commercially available bleaching/cleaning compositions: Tsunami 100®, made available by Ecolab Inc.; Oxonia Active®, made available by Ecolab Inc.; hydrogen peroxide (35%); and PAP-70®, made available by Solvay. These chemicals were used as is, except for pH adjustments to pH 8 using sodium bicarbonate and to pH 12 by adding sodium hydroxide to hard water of hardness 5.

Samples of fabric stained with tea, blood, or wine were used in this example. The stained samples were washed using the same experimental procedure described earlier in Example 2. However, for this example, the stained samples were washed for 10 minutes at 48 °C (120 °F). The pH of the washing solution for all samples was approximately 9. The percentage of stain removal (SR) was determined according to the method described above in Example 2. The table below shows the results of this study.

Table 9.

<td colspan="7">Tea stain removal</td>

<td>Type of bleach</td><td>pH</td><td>Temp. (F)</td><td>Wash time- gem (min)</td><td>%SR</td><td>Bleach solution usage mg/l</td><td>Solution for use with available oxygen (ppm)</td>

<td>Composition, including compound D</td><td> 9</td><td> 120</td><td> 10</td><td> 37</td><td> 1350</td><td> 56</td>

<td>Tsunami 100®</td><td> 9</td><td> 120</td><td> 10</td><td> 34</td><td> 770</td><td> 56</td>

<td>Oxonia Acti-</td><td> 9</td><td> 120</td><td> 10</td><td> 27</td><td> 410</td><td> 56</td>

<td>ve®</td><td></td><td></td><td></td><td></td><td colspan="2"></td><td></td>

<td>H2O2 (35%)</td><td> 9</td><td> 120</td><td> 10</td><td> 24</td><td colspan="2"> 340</td><td> 56</td>

<td>PAP-70</td><td> 9</td><td> 120</td><td> 10</td><td> 63</td><td colspan="2"> 1386</td><td> 56</td>

<td>Water (control)</td><td> 9</td><td> 120</td><td> 10</td><td> 11</td><td colspan="2"> 0</td><td> 56</td>

<td colspan="8"></td>

<td colspan="8">Blood stain removal</td>

<td>Type of bleach</td><td>pH</td><td>Temp. (F)</td><td>Wash time- gem (min)</td><td colspan="2">%SR</td><td>Bleach solution usage mg/l</td><td>Solution for use with available oxygen (ppm)</td>

<td>Composition, including compound D</td><td> 9</td><td> 120</td><td> 10</td><td colspan="2"> 90</td><td> 1350</td><td> 56</td>

<td>Tsunami 100®</td><td> 9</td><td> 120</td><td> 10</td><td colspan="2"> 81</td><td> 770</td><td> 56</td>

<td>Oxonia Active®</td><td> 9</td><td> 120</td><td> 10</td><td colspan="2"> 80</td><td> 410</td><td> 56</td>

<td>H₂THE₂ (35%)</td><td> 9</td><td> 120</td><td> 10</td><td colspan="2"> 82</td><td> 340</td><td> 56</td>

<td>PAP-70</td><td> 9</td><td> 120</td><td> 10</td><td colspan="2"> 88</td><td> 1386</td><td> 56</td>

<td>Water (control)</td><td> 9</td><td> 120</td><td> 10</td><td colspan="2"> 36</td><td> 0</td><td> 0</td>

<td></td><td></td><td></td><td></td><td colspan="2"></td><td></td><td></td>

<td colspan="2">Stain removal</td><td colspan="6">and red wine</td>

<td>Type of bleach</td><td>pH</td><td>Temp. (F)</td><td>Wash time- gem (min)</td><td colspan="2">%SR</td><td>Bleach solution usage mg/l</td><td>Solution for use with available oxygen (ppm)</td>

<td>Composition, including compound D</td><td> 9</td><td> 120</td><td> 10</td><td colspan="2"> 62</td><td> 1350</td><td> 56</td>

<td>Tsunami 100®</td><td> 9</td><td> 120</td><td> 10</td><td colspan="2"> 57</td><td> 770</td><td> 56</td>

<td>Oxonia Active®</td><td> 9</td><td> 120</td><td> 10</td><td colspan="2"> 41</td><td> 410</td><td> 56</td>

<td>H₂THE₂ (35%)</td><td> 9</td><td> 120</td><td> 10</td><td> 45</td><td> 340</td><td> 56</td>

<td>PAP-70</td><td> 9</td><td> 120</td><td> 10</td><td> 74</td><td> 1386</td><td> 56</td>

<td>Water (control)</td><td> 9</td><td> 120</td><td> 10</td><td> 36</td><td> 0</td><td> 56</td>

As can be seen in this table, with regard to tea stains, the PAP-70® composition achieved the highest stain removal. Following that, the composition with a compound of the present invention achieved the highest percentage of stain removal. With regard to blood stains, the composition containing the sulfoperoxycarboxylic acid of the present invention achieved the highest stain removal. However, all concentrated oxidants performed well in removing blood stains. With regard to red wine stains, the sulfoperoxycarboxylic acid of the present invention performed well compared to PAP-70®.

Example 4 - Stability studies

The stability of a sulfoperoxycarboxylic acid of the present invention, namely 11-sulfoundecaneperoxoic acid (Compound D), was compared with that of phthalimidoperoxyhexanoic acid (PAP). The stability data of the PAP sample were extracted from U.S. Patent No. 5,994,284, assigned to Clariant GmbH. Samples of the compound of the present invention were stored for four (4) weeks at different temperatures. The loss of active oxygen was measured by titrimetry. The results are shown in the table below.

Table 10.

<td>Compound</td><td>Storage time (weeks)</td><td>Temperature (°C)</td><td>Active oxygen loss (%)</td>

<td>Compound D</td><td> 4</td><td>Temp, environment</td><td> 0.78</td>

<td>Compound D</td><td> 4</td><td> 38</td><td> 7.9</td>

<td>Compound D</td><td> 4</td><td> 50</td><td> 15.7</td>

<td>PAP</td><td> 4</td><td> 25</td><td> 1.4</td>

<td>PAP</td><td> 4</td><td> 40</td><td> 2.0</td>

<td>PAP</td><td> 4</td><td> 50</td><td> 12.0</td>

As can be seen in this table, the compound of the present invention was more stable, i.e., it lost less active oxygen, at room temperature, around 23 °C, than PAP at 25 °C.

Example 5 - Bleaching performance of various formulas of the present invention

A test was conducted to compare the bleaching properties of compositions of the present invention with the following commercially available bleaching agents: Ozonit®, made available by Ecolab Inc., and PAP®, made available by Clariant. The following compositions of the present invention were used: Formula A, which included approximately 25% by weight of the product of sulfonated peroleic acid, approximately 70% by weight of H₂THE₂(35%) and approximately 5% by weight of HEDP 60; Formula B which included approximately 24% by weight of a mixture of sulfonated peroleic acid and peroxyoctanoic acid, approximately 72% by weight of H₂THE₂ (35%) and approximately 4% by weight of HEDP 60; and Formula C which included approximately 20% by weight of a mixture of the product of sulfonated peroleic acid and peroxyoctanoic acid, approximately 62% by weight of H₂THE₂ (35%), approximately 4% by weight of HEDP 60 and approximately 13% by weight of acetic acid. These formulas were compared to commercially available bleaching agents at 40 °C at a pH between 7 and 8. Ozonit® was also tested at 60 °C.

To measure the bleaching ability of the formulations, a bleaching test described in Example 2 was performed. The results are shown in Figure 4. As can be seen in this figure, Formulas A, B, and C had significantly superior bleaching ability compared to Ozonit® at 40°C. When Ozonit® was used at 60°C, Formulas A, B, and C had very similar bleaching ability. Formula C also had similar bleaching performance compared to PAP. Thus, Formulas A, B, and C showed equal, if not better, bleaching properties compared to known and commercially available bleaching agents at 40 °C.

Example 6 - Antimicrobial studies (a) Bactericidal efficacy

An experiment was conducted to determine the bactericidal efficacy of a composition according to the present invention, with and without surfactant, compared to other products available on the market. Formula A included approximately 1,190 ppm of a sulfonated peroleic acid product, in addition to peroxyoctanoic acid and peracetic acid. The surfactant used in this example was Turboemulsion® (TE), commercially available from Ecolab Inc. The compositions were tested against Clostridium difficile ATCC 9689, MRSA ATCC 33592, Enterococcus hirae ATCC 10541, Escherichia coli ATCC 11229, and Pseudomonas aeruginosa ATCC 15442, at exposure times of 5 and 60 minutes. The commercially available compositions Ozonit® and PAP were also tested. The following formulations were tested:

Table 11.

<td>Test formulation</td><td>Desired concentration of active agent</td><td>Diluent</td><td>Solution used in the test (volume of test substance/total volume)</td><td>pH</td>

<td>Formula A with surfactant</td><td>1,190 ppm</td><td>MilliQ sterile water</td><td>0.194g of Formula A + 170 plc of TE/100g</td><td> 7.59</td>

<td>Surfactant-free Formula A</td><td>1,190 ppm</td><td rowspan="3"></td><td>0.194 g of Formula A/100g</td><td> 8.53</td>

<td>PAP®</td><td>1,820 ppm</td><td>0.182 g of PAP + 1.5 g of TE/100g</td><td> 8.50</td>

<td>Ozonit®</td><td> 2000</td><td>0.200 g of Ozonit + 1.5 g of TE/100g</td><td> 7.21</td>

The test method used was in accordance with European Standard EN 13704: Quantitative Suspension Test for the Evaluation of Sporicidal Activity of Chemical Disinfectants and Antiseptics Used in Food, Industrial, Domestic and Institutional Areas. In general, a test suspension of bacterial spores in a solution of interfering substance, simulating cleaning conditions, was added to a prepared sample of the test formulation diluted in hard water. The mixture was maintained at the specific temperature for the desired time. During this contact time, an aliquot was taken, and the sporicidal action in that portion was immediately neutralized or suppressed by a validated method. The number of surviving bacterial spores in each sample was determined, and the reduction in viable counts was calculated.

The disinfectant properties of each formulation, at 5 minutes and 40 °C, are shown in Table 12.

Table 12.

<td>Test/System</td><td>Formula A with surfactant</td><td>PAP</td><td>Ozonit</td><td>Surfactant-free Formula A</td>

<td>MRSA</td><td> &gt;6.66</td><td> &gt;6.66</td><td> &gt;6.66</td><td> &gt;6.66</td>

<td>Enterococcus hirae ATCC 10541</td><td> &gt;6.26</td><td> &gt;6.26</td><td> &gt;6.26</td><td> &gt;6.26</td>

<td>Escherichia coh ATCC 11229</td><td> &gt;6.74</td><td> &gt;6.74</td><td> &gt;6.74</td><td> &gt;6.74</td>

<td>Pseudomonas aeruginosa ATCC 15442</td><td> &gt;6.32</td><td> &gt;6.32</td><td> &gt;6.32</td><td> &gt;6.32</td>

<td>Clostridium difficile ATCC 9689</td><td> &gt;3.87</td><td> 1.17</td><td> 2.57</td><td> 3.09</td>

As can be seen in this table, the compositions of the present invention that were tested were as effective as a disinfectant as the commercially available formulations tested. Furthermore, with respect to Clostridium difficile, the compositions of the present invention were more effective than the commercially available products tested.

(b) Stability and sporicidal efficacy in 14 days

A test was conducted to determine the stability and sporicidal efficacy of a composition of the present invention against spores. The composition tested included the sulfonated peroleic acid product and an amount of peroxyoctanoic acid. The test method used was in accordance with the European Standard EN 13704: Quantitative Suspension Test for the Evaluation of Sporicidal Activity of Chemical Disinfectants and Antiseptics Used in Food, Industrial, Domestic and Institutional Areas, described below. The table below displays the results of this study.

Table 13.

<td colspan="2"></td>

<td colspan="2">Water DL</td>

<td colspan="2">pH 6.5</td>

<td>B. subtilis</td><td>C. difficile</td>

<td colspan="2">Cleaning conditions</td>

<td colspan="2">20 °C</td>

<td>60 min</td><td>60 min</td>

<td>Log reduction of 3.84</td><td>Log reduction of 2.71</td>

A composition that included 30 ppm of peroxyoctanoic acid was also tested. The composition containing only peroxyoctanoic acid did not result in a reduction.

Figure 5 shows the impact of the stability that the compound used in the present invention, namely the sulfonated peroleic acid product, had on the amount of POOA over time during this study. As can be seen in this figure, the amount of POOA available over time was greater with the POOA sample stabilized with a composition of the present invention compared to a POOA sample not stabilized with a composition of the present invention.

(c) Synergistic effect of a composition of the present invention with a known disinfectant

For this study, ASME 1052-96 was used: A standard test method for the effectiveness of antimicrobial agents against viruses in suspension. A composition that included 1,000 ppm of peroxyacetic acid (POAA) was tested alone and in combination with the sulfonated peroleic acid product.

The POAA solution alone did not show complete inactivation of poliovirus type 1 after an exposure time of 4 minutes. The reductions in viral titer were &lt; 0.75 and &lt; 0.50 log.₁₀When the POAA solution was tested with 1,000 ppm of sulfonated pearloleic acid product, it showed complete inactivation of poliovirus type 1 after an exposure time of a few minutes and was therefore effective against the virus. The reduction in viral titer was 5.75 log .₁₀.

(d) Synergistic effect of a compound of the present invention with peroxyoctanoic acid

For this study, the MS103 was used: A quantitative tuberculocidal test. The sulfonated peroleic acid product was tested alone and in combination with peroxyoctanoic acid at various concentrations against Mycobacterium bovis BCG. The compositions were tested at a pH of 6.5 at room temperature. The results are shown in the table below.

Table 14.

<td>Test substance</td><td>Exposure time</td><td>Log reduction</td>

<td>1,000 ppm of sulfonated peroleic acid product</td><td>2.5 min</td><td> 4.46</td>

<td></td><td>5 min</td><td> 5.11</td>

<td>300 ppm of POA</td><td>2.5 min</td><td> 3.48</td>

<td></td><td>5 min</td><td> &lt;4.31</td>

<td>1,000 ppm of sulfonated peroleic acid product and 300 ppm of POOA.</td><td>2.5 min</td><td> &gt;7.31</td>

<td></td><td>5 min</td><td> &gt;7.31</td>

<td>1,000 ppm of sulfonated peroleic acid product and 150 ppm of POOA.</td><td>2.5 min</td><td> &gt;7.31</td>

<td></td><td>5 min</td><td> &gt;7.31</td>

As can be seen in this table, samples treated with a composition of the present invention that included the sulfonated peroleic acid product and POOA had a greater log reduction of Mycobacterium bovis BCG than samples treated with the sulfonated peroleic acid product or POOA alone. However, it was found that samples treated only with the sulfonated peroleic acid product had a greater log reduction of bacteria than samples treated only with POOA.

(e) Use of a compound of the invention as a hospital disinfectant

For this test, the AOAC Official Method 955.15 - Testing Disinfectant Against Staphylococcus aureus and the AOAC Official Method 964.02 - Testing Disinfectants Against Pseudomonas aeruginosa were used. The composition used included sulfonated peroleic acid and peroxyoctanoic acid (POOA) products in different concentrations. The following table summarizes the test procedure used and the results.

Table 15.

<td>Test substance</td><td>Desired concentration</td><td>Diluent</td><td colspan="2">Dilution (Volume of the test system / Total volume)</td><td>pH test</td>

<td>Product of sulfonated pearloleic acid + POOA</td><td>1,000 ppm of sulfonated peroleic acid product 300 ppm of POA</td><td rowspan="2">400 ppm synthetic hard water</td><td colspan="2">2.910g of sulfonated peroleic acid product + 0.2345g of POOA i 1,500 g</td><td> 6.5</td>

<td></td><td>1,000 ppm of sulfonated peroleic acid product 150 ppm of POAO</td><td colspan="2">0.1852 g of sulfonated peroleic acid product + 0.4690 g of POOA/1.500 g</td><td> 6.5</td>

<td colspan="2">Test system</td><td colspan="2">Test substance</td><td colspan="2">Number of negative tubes: 1 Number of vehicles tested</td>

<td colspan="2">Staphylococcus aureus ATCC 6538</td><td colspan="2">1,000 ppm of sulfonated peroleic acid product + 300 ppm of POOA</td><td colspan="2"> 60/60</td>

<td colspan="2">Staphylococcus aureus ATCC 6538</td><td colspan="2">1,000 ppm of sulfonated peroleic acid product + 150 ppm of POOA</td><td colspan="2"> 60/60</td>

<td colspan="2">Pseudomonas aeruginosa ATCC 15442</td><td colspan="2">1,000 ppm of sulfonated peroleic acid product + 300 ppm of POOA</td><td colspan="2"> 60/60</td>

<td colspan="2">Pseudomonas aeruginosa ATCC 15442</td><td colspan="2">1,000 ppm of sulfonated peroleic acid product + 150 ppm of POOA</td><td colspan="2"> 60/60</td>

As can be seen in this table, the tested compositions were effective against each of the test systems.

Example 7 - Coupling capabilities of the compounds of the present invention

The ability of a composition of the present invention that includes the sulfonated peroleic acid product to couple octanoic acid was compared to the coupling abilities of two known and commercially available coupling agents: NAS and sulfonated linear alkylbenzene (LAS).

The results can be seen in Figure 6. As can be observed in this figure, one gram of the sulfonated peroleic acid product was able to couple twice as much octanoic acid compared to the other coupling agents tested.

Example 8 - Formation of sulfonated carboxylic acids and their percarboxylic salts

A study was conducted to determine the effect of the position of the sulfonated group on the carboxylic acid in the formation of a peracid. Specifically, the study was conducted to determine whether having the sulfonated group in the α position prohibits the oxidation and/or perhydrolysis of the carboxylic acid group to form the corresponding peroxycarboxylic acid.

Commercially available sulfonated fatty acid salts (methyl esters) are predominantly sulfonated in α, including, for example, Alpha-Step PC-48 (commercially available from Stepan Comp.), Alpha-Step MC-48 (MC-48) (commercially available from Stepan Comp.), Alpha-Step BSS-45 (commercially available from Stepan Comp.), and MES (commercially available from Lion Corporation). Structurally, these compounds are C12-C14 sodium alpha-sulfomethyl esters.₁₈ and the alpha-sulfodisodium fatty acid salts Ci₂-W₁₈Their structures are shown below:

<img file="BRPI0907918A2_D0011.tif" />

ONLY₃In

Sulfonated oleic acid is another commercially available sulfonated fatty acid. These compounds are primarily salts of 8-sulfo-octadecenoic acid, with a minority of 9-sulfo-10-hydroxy-octadecanoic acid salts. They are not sulfonated at the α-position. The structures of these types of compounds are shown below:

<img file="BRPI0907918A2_D0012.tif" />

<img file="BRPI0907918A2_D0013.tif" />

only₃m⁺

Alpha-sulfonated fatty acids were prepared by hydrolysis of a mixture of methyl esters of alpha-sulfonated fatty acids and the acid (MC-48). In a beaker containing 25 g of MC-48, 12 g of 50% NaOH solution were added. The mixture was stirred at room temperature for 3 hours. The mixture was then acidified by adding 50% H2SO4 until the pH of the mixture reached approximately 0-1. The white solid precipitate was filtered, washed with cold water, and dried. The resulting white solid powder was evaluated using¹³C NMR (DMSO-d_andThe methyl group of the methyl ester in the raw material was not observed, indicating complete hydrolysis.

In order to attempt to form peracid using an acid-catalyzed hydroxide reaction, the following reaction was performed. 0.5 g of the fatty acid sulfonate derived from MC48, as prepared above, was weighed into a 50 ml beaker. To this beaker, 30 g of H were added.₂THE₂ (35%). Then, 5g of H₂ONLY₄ (985) were added slowly, producing a clear solution. After standing at 50 °C for 24 hours, the solution was analyzed to determine the presence of a peracid.

To determine the presence of a peracid, a kinetic iodometric titration similar to the method disclosed in Sully and Williams (“The Analysis of Per-Acids and Hydrogen Peroxide,” The Analyst, 87:1037, p. 653 (Aug. 1962)) was used. This method demonstrated a lower detection limit of approximately 0.3 ppm for POAA. In view of the molecular weight relationship of POAA with the percarboxylic acid perspective of PC-48, the detection limit was estimated at approximately 1.4 ppm (3.93 x 10⁻⁶ M). No peracid formation was observed. This is equivalent to a percarboxylic acid formation constant (Keq) of less than 0.002, suggesting that basically no peracid was formed.

Alternatively, peracid formation was determined using¹³C NMR (D₂0). Using this technique, no carbonyl resonance signal of the peracid was observed.

Other sources of sulfonated fatty acids in α, such as Alpha-Step PC-48 and AlphaStep BSS-45, also reacted with H.₂THE₂ Similarly, in both cases, no corresponding peracids were detected.

Non-sulfonated fatty acids in α were also tested to determine the likelihood of peracid formation. For the sulfonated oleic acid examined above, the measured formation constant was 1.42. The sulfonated undecenoic acid was collected as a stable solid powder, so the formation constant was not measured. Although the formation constant of sulfonated oleic acid peracid is significantly lower than that of the more commonly marketed peracid, peroxyacetic acid (Keq = 2.70), it is still high enough to produce practical results.

In general, without wanting to be tied to any particular theory, it is believed that the α-sulfo group prohibits the oxidation and/or perhydrolysis of the carboxylic acid group by H.₂THE₂ in the corresponding peracid. This may occur, in part, due to its strong electron-withdrawing effects.

Example 9 - Disinfection compositions for on-site cleaning

A study was conducted to determine the effectiveness of the compositions of the present invention as disinfectants used in an on-site cleaning method. A composition was prepared that included approximately 5.85% by weight of the product of sulfonated peroleic acid and approximately 11.6% hydrogen peroxide, approximately 1% by weight of a chelating agent, approximately 12.75% by weight of H2SO4, approximately 13.6% by weight of NAS-FAL (sodium octane sulfonate), and approximately 1.5% by weight of SXS (commercially available from Stepan Company). Synthetic hard water was used to dilute the test composition to the desired peracid concentration. The peracid was tested at concentrations of 1,000 ppm, 750 ppm, and 500 ppm. The pHs of the solutions used were as follows:

<td>Peracid concentration in the solution for use</td><td>pH</td>

<td>500 ppm of peracid</td><td> 1.65</td>

<td>750 ppm</td><td> 1.46</td>

<td>1,000 ppm</td><td> 1.38</td>

The solutions for use were tested against Staphylococcus aureus ATCC 6538 and Pseudomonas aeruginosa ATCC 15442. The organic stains used were 5% fetal bovine serum. The exposure time for the test was 5 minutes at a temperature of 20 ± 1 °C.

A neutralizing screen was also prepared as part of the tests to verify that the neutralizer adequately rendered the product unusable and was not harmful to the organisms tested. The plates were incubated at 35 °C for 48 hours with the test systems prior to exposure to peracids. The results are shown in the table below.

Table 16.

Staphylococcus aureus ATCC 6538

<td>Test substance</td><td>Number of negative tubes: 1 Number of vehicles tested</td>

<td>1,000 ppm of peracid composition</td><td> 60/60</td>

Pseudomonas aeruginosa ATCC 15442

<td>Test substance</td><td>Number of negative tubes / Number of vehicles tested</td>

<td>1,000 ppm of peracid composition</td><td> 60/60</td>

Test controls

<td>Control</td><td>Test system</td><td>Results</td>

<td>Negative vehicle</td><td></td><td>1 negative out of 1 tested</td>

<td>Positive vehicle</td><td>Staphylococcus aureus ATCC 6538</td><td>1 positive out of 1 tested</td>

<td>Positive vehicle</td><td>Pseudomonas aeruginosa ATCC 15442</td><td>1 positive out of 1 tested</td>

<td>Organic stain</td><td></td><td>1 negative out of 1 tested</td>

<td>Neutralization (1,000 ppm)</td><td>Staphylococcus aureus ATCC 6538</td><td>6 positive out of 6 tested</td>

<td>Neutralization (1,000 ppm)</td><td>Pseudomonas aeruginosa ATCC 15442</td><td>6 positive out of 6 tested</td>

<td>Culture enumeration</td><td>Staphylococcus aureus ATCC 6538</td><td>9.0 x 10⁸ CFU/ml</td>

<td>Culture enumeration</td><td>Pseudomonas aeruginosa ATCC 15442</td><td>1.0 x 10⁹ CFU/ml</td>

<td>Vehicle enumeration</td><td>Staphylococcus aureus ATCC 6538</td><td>1.0 x 10^B CFU/ml 1.0 x 10⁷ CFU/vehicle</td>

<td>Vehicle enumeration</td><td>Pseudomonas aeruginosa ATCC 15442</td><td>2.3x10⁶ CFU/ml 2.3 x 10⁷ CFU/vehicle</td>

Staphylococcus aureus ATCC 6538

<td>Test substance</td><td>Number of negative tubes / Number of vehicles tested</td>

<td>500 ppm of peracid composition</td><td> 59/60</td>

<td>750 ppm of peracid composition</td><td> 60/60</td>

Pseudomonas aeruginosa ATCC 15442

<td>Test substance</td><td>Number of negative tubes / Number of vehicles tested</td>

<td>500 ppm of peracid composition</td><td> 58/60</td>

<td>750 ppm of peracid composition</td><td> 60/60</td>

Test controls

<td>Control</td><td>Test system</td><td>Results</td>

<td>Negative vehicle</td><td></td><td>1 negative out of 1 tested</td>

<td>Positive vehicle</td><td>Staphylococcus aureus ATCC 6538</td><td>1 positive out of 1 tested</td>

<td>Positive vehicle</td><td>Pseudomonas aeruginosa ATCC 15442</td><td>1 positive out of 1 tested</td>

<td>Organic stain</td><td></td><td>1 negative out of 1 tested</td>

<td>Neutralization</td><td>Staphylococcus aureus ATCC 6538</td><td>3 positive out of 3 tested.</td>

<td>Neutralization</td><td>Pseudomonas aeruginosa ATCC 15442</td><td>3 positive out of 3 tested.</td>

<td>Enumeration of</td><td>Staphylococcus aureus ATCC 6538</td><td>1.0 x 10⁹ CFU/ml</td>

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

<td>Culture enumeration</td><td>Pseudomonas aeruginosa ATCC 15442</td><td>1.0 x 10⁹ CFU/ml</td>

<td>Vehicle enumeration</td><td>Staphylococcus aureus ATCC 6538</td><td>7.2 x 10® CFU/ml 7.2 x 10® CFU/vehicle</td>

<td>Vehicle enumeration</td><td>Pseudomonas aeruginosa ATCC 15442</td><td>2.0 x 10® CFU/ml 2.0 x 10⁷ CFU/vehicle</td>

As can be seen from these results, the tested solutions were effective disinfectants against Staphylococcus aureus and Pseudomonas aeruginosa at the tested concentrations.

Another study was conducted to determine the disinfection efficacy of the 5-test solution against Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 11229 after an exposure time of 30 seconds. For this experiment, the solutions were diluted to have a concentration of 50 ppm, 75 ppm, or 100 ppm of the sulfonated pearloleic acid product. The pHs of the solutions used were as follows:

<td>Peracid concentration in the solution for use</td><td>pH</td>

<td>50 ppm of peracid</td><td> 2.70</td>

<td>75 ppm</td><td> 2.47</td>

<td>100 ppm</td><td> 2.30</td>

The solutions for use were tested against Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 11229. The exposure time was 30 seconds at a temperature of 25 ± 1 °C. A neutralizing screen was also prepared as part of the tests to verify that the neutralizer adequately rendered the product unusable and was not harmful to the organisms tested. The plates were incubated at 35 °C for 48 hours with the test systems prior to exposure to the peracids. The results are shown in the table below.

Table 17.

Inoculum numbers

<td>Test system</td><td>CFU/ml</td><td>Log growth₀</td><td>Average log growth</td>

<td>Staphylococcus aureus ATCC 6538</td><td>107x10®, 109x10®</td><td> 8.03, 8.04</td><td> 8.04</td>

<td>Escherichia coli ATCC 11229</td><td>138x10®, 151 x10^B</td><td> 8.14, 8.18</td><td> 8.16</td>

Staphylococcus aureus ATCC 6538

<td>Test substance</td><td>Survivors (CFU/ml)</td><td>Logio growth</td><td>Average logistics growth_Q</td><td rowspan="2">Log reduction 5.66</td>

<td>50 ppm of peracid composition</td><td>28 x 10¹, 20 x 10¹</td><td> 2.45, 2.30</td><td> 2.38</td>

<td>75 ppm of peracid composition</td><td>0 x 10¹, 100 x 10¹</td><td> &lt;1.00, 3.00</td><td> &lt;2.00</td><td> &gt;6.04</td>

<td>100 ppm of peracid composition</td><td>0x10¹, 0x10¹</td><td> &lt;1.00, &lt;1.00</td><td> &lt;1.00</td><td> &gt;7.04</td>

Escherichia coli ATCC 11229

<td>Test substance</td><td>Survivors (CFU/ml) .</td><td>Growth</td><td>Average log-growth₀</td><td>Log reduction</td>

<td>50 ppm of peracid composition</td><td>Ox 10¹, 2x10¹</td><td> &lt;1.00, 1.30</td><td> &lt;1.15</td><td> &gt;7.01</td>

<td>75 ppm of peracid composition</td><td>Ox 10¹, 0χ10^A</td><td> &lt;1.00, &lt;1.00</td><td> &lt;1.00</td><td> &gt;7.16</td>

<td>100 ppm of peracid composition</td><td>Ox 10¹, Ox 10¹</td><td> &lt;1.00, &lt;1.00</td><td> &lt;1.00</td><td> &gt;7.16</td>

As can be seen from these results, the tested solutions were effective disinfectants against Staphylococcus aureus and Escherichia coli. The test solution containing 100 ppm of the sulfonated pearloleic acid product was the most effective disinfectant.

Example 10 - Foaming properties of selected compositions of the present invention

A study was conducted to determine the foaming properties of selected compositions of the present invention compared with compositions that included commercially available surfactants. The following compositions were prepared: Formula A included 50 ppm of the sulfonated peroleic acid product at pH 2.48; Formula B included 50 ppm of the sulfonated peroleic acid product at pH 6.75; Formula C included 64 ppm of a commercially available sulfonated oleic acid (SOA) (Lankropol OPA (50%), supplied by Akzo Nobel) at pH 2.48; Formula D included 64 ppm of a commercially available sulfonated oleic acid (Lankropol OPA - 50% supplied by Akzo Nobel) at pH 6.56; Formula E included 128 ppm of a commercially available sulfonated oleic acid (Lankropol OPA - 50% supplied by Akzo Nobel) at pH 2.48; Formula F included 128 ppm of a commercially available sulfonated oleic acid (Lankropol OPA - 50% supplied by Akzo Nobel) at pH 7.20; Formula G included 93 ppm of sodium octane sulfonate (NAS) (commercially available from Ecolab) at pH 2.48. Foam heights were determined using the following method. First, 3000 ml of each formula were prepared and gently poured into the Glewwe cylinder. A ruler was attached to the side of the cylinder, and the solution was leveled with the bottom of the ruler. The pump was then turned on. The foam height was estimated by reading the average foam level according to the ruler. Foam height readings were taken over time using a stopwatch or timer. The pump was turned off and the foam height was recorded at various times. The results are shown in the table below.

Table 18.

<td>Sample</td><td colspan="3">Pump on time (s)</td><td colspan="3">Pump off time (s)</td>

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

<td></td><td> 30</td><td> 60</td><td> 300</td><td> 30</td><td> 60</td><td> 300</td>

<td></td><td>Foam height (in.)</td><td>Foam height (in)</td><td>Foam height (in.)</td><td>Foam height (in.)</td><td>Foam height (in.)</td><td>Foam height (in.)</td>

<td>Formula A</td><td> 2.5</td><td> 3.8</td><td> 5.5</td><td> 3.5</td><td> 2.0</td><td> 0.5</td>

<td>Formula B</td><td> 1.5</td><td> 2.0</td><td> 2.5</td><td> 0.2</td><td> &lt;0.1</td><td>N/A</td>

<td>Formula C</td><td> 4.0</td><td> 6.2</td><td> 9.2</td><td> 8.7</td><td> 8.5</td><td> 5.5</td>

<td>Formula D</td><td> 3.1</td><td> 4.5</td><td> 10</td><td> 9.8</td><td> 8.5</td><td> 4.0</td>

<td>Formula E</td><td> 2.6</td><td> 4.5</td><td> 8.5</td><td> 8.2</td><td> 8.0</td><td> 5.0</td>

<td>Formula F</td><td> 0.15</td><td> 0.15</td><td> 0.2</td><td> &lt;0.1</td><td> &lt;0.1</td><td> &lt;0.1</td>

<td>Formula G</td><td> 1.0</td><td> 1.0</td><td> 1.2</td><td> 0.4</td><td> 0.2</td><td> &lt;0.1</td>

As can be seen from these results, the formulas that included compositions of the present invention, namely Formulas A and B, had much lower foam heights than Formulas C and D, which included the non-peracid form of the sulfonated material, namely sulfonated oleic acid. The reduced foam height of the compositions of the present invention is useful when using the compositions in applications where foam production is detrimental to the application, for example, in a spot cleaning and/or disinfection application.

Example 11 - Disinfection solutions for laundries

A study was conducted to determine the ability of a composition of the present invention to disinfect clothing during washing. A composition containing sulfonated peroleic acid was tested in comparison with commercially available cleaning compositions: Ozonit®, made available by Ecolab Inc., and PAP-70®, made available by Solvay. The compositions were tested against Staphylococcus aureus ATCC 6538 and Pseudomonas aeruginosa ATCC 15442 at 40 °C (104 °F) for 6 minutes.

The following test method was used. Tissue samples were obtained that had been rinsed with boiling water containing 300 grams of sodium carbonate and 1.5 grams of a non-ionic wetting agent (e.g., Triton X-100), followed by rinsing with cold water until all visible traces of the wetting agent were removed. The tissue samples were allowed to dry completely. The tissue samples were then placed in an autoclave for sterilization.

The test substances were then prepared, and tissue samples were inoculated with the test substances. The inoculated samples were then dried. Next, the samples were placed in a washing speed tester and agitated in wash water. The wash water was removed from the washing chamber, and both it and the tissue samples were evaluated for reduction in the population of the tested microorganisms.

The results are shown in the table below.

Table 19.

<td>Test/System</td><td>Composition that includes sulfonated peroleic acid product.</td><td>PAP-70®</td><td>Ozonit®</td>

<td>Disinfectant screen</td><td> &gt;3.82</td><td> &gt;3.82</td><td>N/A</td>

<td>Disinfectant (fabric conveyor belt)</td><td>9 negative / 9 total</td><td>9 negative / 9 total</td><td>5 negative/9 total</td>

As can be seen from these results, the composition of the present invention tested showed a reduction greater than 3 log in the washing water and in the fabric carriers against P. aeruginosa and in the latter against S. aureus.

The present invention also relates to new compounds and their synthesis. Thus, the following examples are presented to illustrate how some of these compounds can be prepared.

Synthesis of selected compounds of the invention

Preparation of sulfonated peroleic acid product.

417.8 g of OA5-R (from Intertrade Organic, 40% active sulfonated oleic acid) were added to a 2-liter beaker immersed in a large ice bath, to which were subsequently added 66.4 g of Dequest 2010 (60% active hydroxyethylene diphosphonic acid, from Monsanto) and 535 g of hydrogen peroxide (46% active, from SolvayInterox). The beaker was secured with a magnetic stirring bar, and the solution was vigorously stirred while 940 g of sulfuric acid (96% active, Mallinkrodt brand) was added. The rate of addition of sulfuric acid was controlled to produce an exothermic reaction of

48.9 °C (120 °F) in the reaction solution, and although this was sometimes exceeded by several degrees, it was not allowed to exceed 51.7 °C (125 °F). Several minutes after completing the addition of sulfuric acid, the ice bath was stopped and the heterogeneous solution was stirred for 72 hours, allowing the temperature to equilibrate with ambient conditions (21 °C/70 °F).

Several hours after the agitation was stopped, the two-phase reaction solution was added to a separatory funnel and the upper and lower phases were separated. 239.4 g of the upper phase were collected and it was further purified by centrifugation at 3,000 rpm for 10 minutes. The final yield of the upper phase was 206 g (theoretical yield of 174 g) and titrated as 55% peroxyacid based on an assumed molecular weight of 380. Furthermore, the upper phase contained 1.8% hydrogen peroxide. A sample of the centrifuged lower phase was titrated as 13% peroxyacid (MW 380) and 8.8% hydrogen peroxide.

Synthesis of 11-sulfoundecanoic acid and 10,11-disulfoundecanoic acid h₂c^

In₂S₂THE₅ /NaOH/TBPB

O=S=OI CT x ONa ONa

11-Sulfoundecanoic acid

10,11-Disulfoundecanoic acid

11-Sulfundecanoic acid: Deionized water (150 ml), isopropyl alcohol (200 ml), and 11-undecylenic acid (28.56 g, 0.155 mol) were placed in a 1-liter flask equipped with a stirrer, additional funnel, reflux condenser, thermometer, and a gas inlet tube. A premix containing 15.2 g (0.08 mol) of sodium metabisulfite and 1.28 g of NaOH in 55 g of water was added to the additional funnel. The entire apparatus was gently purged with nitrogen. After heating to reflux (82 °C), a small portion of t-butyl perbenzoate (from a total amount of 0.5 g, 2.5 mmol) was added to the flask. Then, the premixed sodium metabisulfite/NaOH was continuously added over a period of five hours to the reaction solution using an addition funnel. The remaining t-butyl perbenzoate was also added in small portions during this time.

The solvent was then removed under reduced pressure using a rotary evaporator, and the residue was washed with acetone and then dried, yielding 31.0 g of white solid. NMR analysis of the solids did not indicate the presence of residual raw materials. The white solid obtained was dissolved in hot water (100 ml, 75 °C) and neutralized to a pH of 5.5 with NaOH.

Next, 2.0 g of H₂THE₂ 50% of the solution was added. The solution was then allowed to cool to room temperature, and the solid precipitate was filtered, washed with cold water, and dried, resulting in 21.0 g of white solid, characterized as pure 11-sulfoundecanoic acid.¹³C NMR (D₂O): 180, 51, 34, 28-29 (multiple), 27.5, 24.5, 24 ppm. MS (ESI): 265.1 (M⁺-H).

10,11-Disulfoundecanoic acid: This compound was obtained as a byproduct of the reaction of 11-sulfoundecanoic acid, as described above. The filtrate, after collection of the 11-sulfoundecanoic acid by filtration, was concentrated to ~50 ml, at which point the precipitate began to form. The mixture was cooled in a refrigerator, and the additional solid formed was filtered, washed with a small amount of ice-cold water, and then dried, yielding 5.0 g of white solid.¹³C NMR (D₂O): 184, 57, 51.5, 37.5, 28-29 (multiple), 27.5, 26, 24 ppm. MS (ESI): 345.0.

Synthesis of 11-sulfoundecaneperoxoic acid (Compound D) and 10,11-disulfoundecaneperoxoic acid (Compound E)

11-sulfoperoxyundecanoic acid:

<img file="BRPI0907918A2_D0014.tif" />

1.3 g of 11-sulfoundecanoic acid was dissolved in 2.5 g of 98% sulfuric acid. To this solution (whose temperature did not exceed 60 °C) 1.5 g of H was added.₂THE₂The mixture was diluted to 50%, and the resulting solution was stirred at room temperature for 1.5 hours. At this point, a white solid precipitated from the solution. The mixture was reheated to 50 °C in a water bath until the solution became clear. The solution was then stirred at room temperature for 0.5 hours and cooled in a refrigerator. Next, 20 ml of ice-cold water were added to the mixture, the filtered solid was washed with ice-cold water and dried under vacuum, yielding 0.6 g of a white solid.¹³C NMR (D₂O): 176, 51.5, 30.5, 27.5-29 (multiple), 24.5, 24 ppm. MS (ESI): 281.5 (M⁺ -H). Available oxygen (iodometric): 5.41% (theoretical: 5.64%).

10,11-Disulfoundecaneperoxoic acid (Compound E):

<img file="BRPI0907918A2_D0015.tif" />

To 1.5 g of 10,11-disulfoundecaneperoxoic acid were added 2.5 g of H₂ONLY₄ at 96%, and the mixture was stirred at room temperature. Then, 1.0 g of H₂THE₂ 50% was slowly added (the temperature did not exceed 60 °C) to the mixture, which, after the addition, was heated to 50 °C in a water bath, and the solution was stirred for 2 hours. The solution was then cooled in the refrigerator, and 20 ml of ice-cold water were added during stirring. The solid precipitate was filtered, washed with ice-cold water, and dried under vacuum, resulting in 1.0 g of white solid.¹³C NMR (D₂O): 175.5, 57, 30.5, 27.5-29 (multiple),

24.5, 24 ppm. Available oxygen (iodometric): 4.10% (theoretical: 4.41%).

Synthesis of 9/10-sulfostearic acid (sulfonated stearic acid)

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Deionized water (150 ml), isopropyl alcohol (200 ml), and oleic acid (43.78 g, 0.155 mol) were placed in a 1-liter flask equipped with a stirrer, additional funnel, reflux condenser, thermometer, and gas inlet tube. A premix containing 15.2 g (0.08 mol) of sodium metabisulfite (Na₂) was added to the additional funnel.₂S₂THE₅) and 1.28 g of NaOH in 55 g of water. The entire apparatus was gently effervesced with nitrogen. After heating to reflux (82 °C), a small portion of tert-butyl perbenzoate (from a total amount of 0.5 g, 2.5 mmol) was added to the flask. Then, the premixed Na₂S₂O5/NaOH was added continuously through the addition funnel over five hours. The remaining t-butyl perbenzoate was also added in portions during this time.

The solvent was then removed under reduced pressure using a rotary evaporator. 100 ml of DL water was added to the residue, and the pH of the solution was adjusted to 2.5 with H2SO4. The resulting mixture/solution was transferred to a separatory funnel, and the top oily layer (unreacted oleic acid) was removed. The aqueous layer was extracted with petroleum ether (2 x 50 ml) and, after removal of the water, resulted in 12.5 g of a white, pasty solid.¹³C NMR (D₂O): 179, 60, 34.5, 32, 28.5-30 (multiple), 24.5, 22.5, 14 ppm. MS (ESI): 363.4 (M⁺ -H).

Preparation of 9/10-sulfoperoxystearic acid (in formulation)

To a mixture of 2.0 g of 9- or 10-sulfostearic acid, 2.0 g of H were added.₂THE₂ at 50%. The mixture was stirred at room temperature until all the solid was dissolved. Then, 2.0 g of H were added.₃DUST₄ The solution was reduced to 75% and the resulting solution was stirred at room temperature overnight. No attempt was made to isolate pure 9- or 10-sulfoperoxystearic acid from the solution.¹³C NMR (D₂O) of the solution showed a peak of peracid (COOOH) at 174 ppm and 0 parent, a peak of carboxylic acid at 178 ppm. Iodometric titration (QATM -202) indicated 18.96% sulfoperoxystearic acid.