Fabric softening compositions comprising polymeric materials.

(54) Title: SOFTENING COMPOSITION OF FABRICS THAT INCLUDE POLYMERIC MATERIALS.

(54) Title: FABRIC SOFTENING COMPOSITIONS COMPRISING POLYMERIC MATERIALS.

(57) Summary

The present invention relates to fabric softening compositions comprising polymeric materials, capable of retaining volatile perfume ingredients, as well as to fabric softening methods.

(57) Abstract

Fabric softening compositions comprising polymeric materials capable of retaining volatile perfume ingredients are disclosed, as well as methods of softening fabrics.

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PATENT TITLE No. 348279

Owner (s): COLGATE-PALMOLIVE COMPANY

Address: 300 Park Avenue, New York, New York, 10022, USA

Name: SOFTENING COMPOSITION OF FABRICS INCLUDING POLYMERIC MATERIALS.

<td>Classification: CIP: CPC:</td><td>C11D3 / 37; C11D1 / 62; C11D3 / 50 C11D3 / 3746; C11D1 / 62; C11D3 / 505</td>

Inventor (s): GUY BROZE; ALAIN JACQUES; ALEXANDRINE TUZI; GEORGES

YIANAKOPOULOS; LOUIS OLDENHOVE, RICHARD PAYNE

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

Number:

MX / a / 2012/011745

International Presentation Date:

May 2008

Divisional Patent Number: 309100

PRIORITY

Country: Date:

US May 31, 2007

Validity: Twenty years

Expiration Date: May 27, 2028

Issue Date: June 2, 2017

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The reference patent is granted based on articles 1, 2, section V, 6^or IU fraction, and 59 of the Industrial Property Law

In accordance with article 23 of the Industrial Property Law. This patent is valid for twenty years, non-extendable, counted from the filing date of the application and will be subject to the payment of the bull to keep the rights in force.

Whoever signs this title does so based on the provisions of articles 6 ° sections III and 7 ° bis, 2 of the Industrial Property Law (Official Gazette of the Federation (DOF) 06/27/1991, amended on 02 / 08/1994, 10/25/1996, 12/26/1997, 05/17/1999, 01/26/2004, 06/16/2005, 01/25/2006, 05/06/2009, 06/01 / 2010, 06/18/2010, 06/28/2010, 01/27/2012 and 04/09/2012); items 1^or 3 »Vinciso fraction a), 4^or and 12th sections I and III of the Regulations of the Mexican Institute of Industrial Property (0.0 F. 12/14/1999, amended on 07/01/2002, 15707/2004 07/28/2004 and 09/07/2007); items 1^or, 3^or, 4^ft, 5^ft fraction V part a), ....... fractions! ^ DLy 30 of the Organic Statute of the Mexican Institute of Industrial Property (DOF 12/27/1999, amended on 10/10/2002, 07/29/2004, 04 / Q8 / 2004 and 09/13/2007) 1 ', 3 "and 5 'subsection a) of the Agreement that delegates powers to the Deputy General Directors, Coordinator. Divisional Directors, Heads of Regional Offices, Divisional Deputy Directors, Departmental Coordinators and other subordinates of the Mexican Institute of Industrial Property (DOF 12/15/1999, amended 02/04/2000, 07/29/2004, 08/04 2004 and 09/13/2007).

This document is signed with an advanced electronic signature (FIEL), based on articles 7 BIS 2 of the Industrial Property Law; 3 of its Regulations, and 1 section III, 2 section V, 26 BIS and 26 TER of the Agreement establishing the guidelines for the use of the Payment and Electronic Services Portal (PASE) of the Mexican Institute of Industrial Property, in the procedures indicated.

THE DIVISIONAL DIRECTOR OF PATENTS

NAHANNY CANAL REYES

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Mexico vw.gob.mx/lympi

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SOFTENING COMPOSITION OF FABRICS THAT COMP ”* ™? * M a POLYMERIC TETALS

I

FIELD OF THE INVENTION

Perfume is an important component of modern fabric softeners, particularly those supplied through the rinse cycle of a washing machine and those present in dryer sheets and other forms. Perfume cost is estimated to represent approximately 50% of the total formula cost of a typical rinse cycle fabric softener. However, there is a high volume of residual perfume in the laundry process; Instrumental measurements have indicated that approximately 50 to 70% of the perfume ingredients in a commercial liquid fabric softener typically remain in the wash liquor, and thus are never deposited on the fabrics to be treated.

BACKGROUND OF THE INVENTION

Consequently, increasing the efficiency of deposition of perfume on fabrics is desirable, because it can allow significant reduction in waste and cost of a commercial fabric softener product. Furthermore, improving the deposition efficiency of volatile ingredients in a

Ref. 236328

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JXSTTTUTO MUMH'i víitE'Er '/ ÍS of property O5 = ·. · «INDUSTRIAL perfume, new perfume notes can be ^Ihw^{, w}'fabric softening compositions and more effectively deposited on treated fabrics.

In laundry products such as fabric softeners, the presence of a perfume is proposed to make the compositions more aesthetically pleasing to consumers.

Apart from the perception point of acquisition, perfume additives can impart a long-lasting and pleasant fragrance to fabrics that are treated with them. However, as noted above, with respect to liquid fabric softening compositions that are added during the laundry process, the major portion of the perfume is often lost in the wash solution during the wash and subsequently discarded.

Attempts have been made in the art to increase the efficiency and deposition of perfumes on fabrics. For example, the use of cross-linked cationic vinyl polymers, 20 has been discussed and explored in conjunction with conditioning formulations and personal care compositions as a thickening agent, for example, in International Patent Publication No. WO 90/12862 and US Patent 4,806,345. Various methods to achieve controlled release have been developed. One of the simplest of such

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incorporations, described in Patent C &amp; IiaaiUHue Ihs. ι &lt;- · «1,111,616 by Young, and US Patent No. 6,042,792 by Shefer et al., which describes incorporation of perfumes into wax. US Patent No. 4,464,2.71, describes encapsulation technology to entrap softening compositions and fragrance oils in solid particles. An example of such microencapsulation technology is included in perfumed capsules, which are broken under friction to provide an instant burst of fragrance when the capsules are broken.

These types of capsules can behave differently depending on the compositions with which they are used. In particular, they can be disadvantageous in that they can often leak in aqueous compositions containing high levels of surfactants and lower alcohols. Since it is desirable to provide scented articles that are stable in flowable compositions but still release perfume in use, different procedures have been used; for example, creating a coating around the particles as described in US Patent No. 5,137,646, or by encapsulating perfume materials in conjunction with high C log P solvents to allow fragrances to remain in capsules for extended times without leaching from capsules, as described in European Patent Publication

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No. 1 533 364 A3. However, there is a need. pdPa the improvement of perfume and deposition efficiency in fabrics and the capture of more volatile ingredients from a perfume for fabric deposition.

The present invention is directed, in certain embodiments, to a cross-linked polymeric material designed as a perfume sponge to retain volatile perfume ingredients. In certain embodiments, the invention is directed to a polymeric material capable of increasing the efficiency of perfume deposition on fabrics such as cotton, when used in conjunction with a rinse cycle fabric softening composition.

BRIEF SYNTHESIS OF THE INVENTION

A fabric softening composition comprising:

(a) about 0.001% to about 50% of a cationic or non-cationic softening compound;

(b) a perfume; and (c) a polymeric material capable of retaining volatile perfume ingredients comprising:

MEXICAN INSTITUTE

OS THE PROPERTY

INDUSTRIAL

i. at least about 0.001% by weight of a cross-linked polymer comprising at least one vinyl monomer, · and ii. about 5,000 to about 100,000 ppm of a divinyl crosslinking agent.

A fabric softening composition comprising a polymeric material capable of retaining volatile perfume ingredients, the polymeric material comprising:

(a) at least about 0.001% by weight of a water dispersible crosslinked cationic polymer derived from the polymerization of about 4% to 80% by weight of a cationic vinyl addition monomer;

(b) about 50% to about 95% by weight acrylamide; and (c) approximately 5,000 to approximately

100,000 ppm of a difunctional vinyl addition monomer crosslinking agent.

A fabric softening composition comprising:

<img file="MX348279B_D0005.tif" />

(a) about 2 to about 10% of

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OF THE INDUSTRIAL WOWITY a fatty ester quaternary ammonium compound;

(b) about 0.01 to about 5% fatty alcohol;

(c) about 0.01 to about 2% lactic acid;

(d) about 0.01 to about 5% of a cross-linked polymer; and '(e) about 0.01 to about 5% of a perfume chosen from eugenol, phenylhexanol and hexyl salicylate.

A fabric softening composition comprising, a cross-linked polymer comprising:

(a) about 40 to about 60% acrylamide;

(b) about 40 to about 50% quaternized dimethylaminoethyl methacrylate; Y

<img file="MX348279B_D0006.tif" />

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OF THE PROPERTY

INDUSTRIAL (c) about 3 to about 8% methylene bis-acrylamide crosslinking agent.

A fabric softening composition comprising a polymeric material capable of retaining volatile perfume ingredients, comprising:

(a) about 1 to about 99% styrene or alpha-methyl styrene monomer®; and (b) about 5,000 to about 100,000 ppm of divinylbenzene crosslinking agent.

A fabric softening composition comprising:

(a) about 1 to about 99% of a polyether polyurethane-polyurea copolymer;

(b) about 2 to about 10% of a fatty ester quaternary ammonium compound; and (cj about 0.01 to about 5% of a perfume selected from eugenol, phenylhexanol, and hexyl salicylate.

In various embodiments, the present invention is directed to methods of softening a fabric which comprise contacting the fabric with an effective amount of the fabric softening compositions of the present invention.

<img file="MX348279B_D0007.tif" />

DETAILED DESCRIPTION OF THE INVENTION

As used here, ranges is a nomenclature to describe any and every value within a range, which includes end points. All references cited in the present description are hereby incorporated by reference in their entirety. Where there is conflict between a definition in the present description and that of a cited reference, the present description controls.

The present invention is directed, in certain embodiments, to a fabric softening composition comprising a polymeric material capable of retaining volatile perfume ingredients. Withholding.

The present invention is directed, in certain embodiments, to a polymeric material that has the ability to provide increased perfume deposition efficiency. As used herein, the term "perfume deposition efficiency" refers to a proportion of perfume

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which is retained on the surface of, v / n - ai-&gt; gnrbi &lt;jia in, a material after the addition of the material's perfume, and can be expressed as, for example, log P. In various embodiments, the compositions of the present invention are capable of providing fabric deposition efficiency of perfume ingredients having a log P below about 3.5 of at least 50%, as opposed to conventional softening compositions, where the deposition rate of such perfume ingredients is significantly low. As used herein, the term "perfume" refers to odoriferous materials that are capable of providing a pleasant fragrance to fabrics, and can encompass conventional materials commonly used in detergents, fabric softening compositions, and other home care uses. For a further discussion of perfumes, see for example, US Patent No. 6,864,223 by Smith et al.

Aside from the cumulative economic advantage of improved perfume deposition efficiency, improved deposition of perfumes with ingredients having various log P values, enables the formulation and design of various new perfume notes for rinsed fabrics. As used herein, log P, (also referred to as the solubility parameter), refers to the log of the division coefficient of a compound, in

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the concentration ratio in which the division coefficient is concentration of compound in aqueous phase to an immiscible solvent - the lipophilicity / hydrophilicity of the compound. For further discussion of log P, see for example, Sina D. Escher and Esther Oliveros: A Quantitative Study of Factors that Influence the Substantivity of Fragrance Chemicals on Laundered and Dried Fabrics: Journal of American Oil Chemist's Society, Vol. 71, No. 1, pp. 31-40 (1994).

In various embodiments, the polymeric material is contained within a fabric softening composition. In various embodiments, the fabric softening composition further contains at least one skin benefit fabric or ingredient, such as perfume contained within a microcapsule having a capsule shell comprising urea formaldehyde or melamine-formaldehyde polymer. The microcapsules can be made of a hard polymeric material that is friable and which breaks after gentle rubbing. In this form, an intense burst of ingredient that benefits the skin or fabric can, for example, be detected in fabric rinsed with a softening composition of the invention during ordinary handling of the fabric. The perfume can then be released as the user wears the garments.

Dry towels washed with a fabric softener from the

<img file="MX348279B_D0011.tif" />

OílflUTO MEXICANO MUFROP! £ DAD INDUSTRlAl invention, have a pleasant fragrance ..... 1111 ^^ 1 rn_; | particularly intense fragrance burst when worn.

In certain embodiments, the compositions of the present invention comprise at least about 0.001% by weight of a cross-linked polymer comprising at least one vinyl monomer. In various embodiments, the vinyl monomer is a cationic vinyl monomer. The deposition on fabric such as cotton is enhanced by the presence of vinyl monomers, and examples of the vinyl monomers employed include, for example, diallyldimethylammonium chloride or the quaternized form of dimethylaminoethyl methacrylate.

In certain embodiments, the polymeric material further comprises a polar monomer such as, for example, acrylamide. In various incorporations, acrylamide. may be present in amounts from about 20 to about 95%, about 25 to about

80%, about 30 to about 75% or about 35 to about 70% of the polymeric material.

Certain embodiments of the present invention may additionally comprise a crosslinking agent. In

<img file="MX348279B_D0012.tif" />

Certain incorporations, the crosslinking agent may be a difunctional vinyl addition monomer crosslinking agent. In various embodiments, the difunctional vinyl addition monomer crosslinking agent is methylene bis 5 acrylamide, a diethylenically unsaturated compound such as, for example, ethylene glycol di-acrylate, diacrylamide, or cyanomethylacrylate.

Copolymers of acrylamide and a cationic monomer, 10 can exhibit thickening / structuring properties. These may not always be desirable beyond a certain degree; however, the affinity for the perfume can result in an increase in the hydrodynamic volume of the copolymer. To prevent uncontrolled thickness and swelling. of the copolymers of acrylamide and a cationic monomer, the amount of crosslinking agent can be adjusted to use relatively high amounts as needed, for example, in various incorporations, about 5,000 to about 100,000 ppm, about 10,000 to about 80,000 ppm, about 20,000 to about 70,000 ppm, about 30,000 to about 60,000 ppm, or about 45,000 to about 55,000 ppm. In certain incorporations, the amount of crosslinking agent is present in an amount of about 50,000 ppm (ie, 5%). In

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Certain incorporations, the agent of τα ^ ίryi ^ g-iAn is .1 ^ 3 - .., methylene acrylamide. In other embodiments, the crosslinking agent is a divinylbenzene crosslinking agent.

In certain embodiments, the polymeric material comprises a cross-linked polymer comprising about 47.5% by weight of acrylamide, about 47.5% by weight of the quaternized form of dimethylaminoethylmethacrylate, and about 5% by weight of methylene bis-acrylamide as the cross-linking agent.

In various embodiments, the water dispersible cross-linked cationic polymer is present in amounts of at least about 0.001% by weight, about 2% to about 50% by weight, or about 5% to about 35% by weight of the polymeric material.

In certain embodiments, the polymeric material comprises a polyether polyurethane-polyurea copolymer. Such a polymer may be commercially available under the trade name Lycra®. In certain embodiments, the present invention is directed to a fabric softening composition comprising:

<img file="MX348279B_D0014.tif" />

(a) about 1 to about 99% of a polyether polyurethane-polyurea copolymer;

(b) about 2 to about 10% of a fatty ester quaternary ammonium compound; and (c) about 0.01 to about 5% of a perfume selected from eugenol, phenylhexanol, and hexyl salicylate.

In other embodiments, the polymeric material of the present invention may be loaded with perfume, in addition to other ingredients such as, for example, ingredients that benefit the skin or agents that control suds, such as, for example, 2-butylhexanol.

The embodiments of the present invention may be further illustrated by the following non-limiting Examples:

EXAMPLE 1

One method of preparing the polymeric material is to mix 50 grams of the two comonomers and the crosslinking agent in the appropriate proportions in 250 ml of a solvent such as benzene, toluene or even tetrahydrofuran.

<img file="MX348279B_D0015.tif" />

(THF). About 2% of a free radical initiator 'such as azobis isobutyronitrile (AIBN) is added to the solution. This solution is added dropwise into a 1 L spherical flask containing 200 ml of the same solvent at its boiling temperature. The spherical flask is fitted with a cooling device to prevent the loss of solvent by evaporation. Polymerization takes place when the solution containing the comonomers, the crosslinking agent, and the free radical polymerization initiator hit the reflux medium.

After completion of the addition, the reflux is maintained for an additional 15 minutes, and then allowed to cool. The solvent is removed under reduced pressure, at a temperature not exceeding 60 ° C. When most of the solvent is removed, the polymeric mass is stored overnight in a desiccator under vacuum to remove the remainder of the solvent.

A non-sticky white powder is obtained by adding 5% of the crosslinking agent (50,000 ppm). With only 1%, you get an elastic, sticky dough.

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<img file="MX348279B_D0016.tif" />

Preparation of the perfume-polymer premix;

The process is similar to one of a normal rinse cycle fabric softener, except that the perfume is replaced by a perfume-polymer premix, which could be obtained after two processes:

• mixing polymer and fragrance without water • mixing polymer, fragrance and water

Assuming that the cross-linked polymer is 25% in water, 50 grams of the polymer gel (12.5 g of polymer) is mixed with 6.25 g of perfume for at least 2 hours. The ratio of polymer and perfume has to be adjusted, between

50: 1 and 1:50, preferably between 10: 1 and 1:10. The proportion of the perfume-polymer premix has to be adjusted as well, between 0.01 and 20%.

The perfume-polymer premix can be introduced into the formula at different stages, for example:

• In the esterquat-fatty alcohol premix • Right after the esterquat premix • In subsequent addition; or · In hot water before premix esterquat.

<img file="MX348279B_D0017.tif" />

EXAMPLE 2

A polymeric material was prepared as follows: A mixture of melamine-formaldehyde and urea-formaldehyde resin is crosslinked with an anhydride copolymer¹ maleic and methyl vinyl ether (commercially known as Gantrez). Capsules were prepared with the above material and three perfume ingredients selected according to their log P (eugenol, phenyl hexane and hexyl salicylate). The capsules were formulated into a fabric softener, and their ability to deposit on cotton was evaluated.

Table 1 shows the amount of perfume molecules that remain deposited on cotton from a fabric softener containing the capsules one day after the fabric softener formulation, compared to the same fabric softener in which the molecules fragrances were not encapsulated with the polymeric material. The difference between the amount deposited for encapsulation versus non-encapsulated polymeric material was found to be large for eugenol and phenyl hexanol (which have low or medium log P values), and small for hexyl salicylate (which has a higher log P value). This suggests that encapsulation has a higher potential impact on the deposition of log P from higher perfumes such as

<img file="MX348279B_D0018.tif" />

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Table 1

<td></td><td>pg / g cotton (with capsules)</td><td>pg / g cotton (not encapsulated)</td>

<td>Eugenol (log P = 2.3)</td><td> 53</td><td>None Detected</td>

<td>Phenyl Hexanol (log P = 3.3)</td><td> 55</td><td> 22</td>

<td>Hexyl Salicylate (log P = 5.26)</td><td> 65</td><td> 52</td>

When the same measurements are performed again after 2 weeks, the results indicated that there is no detectable difference between levels of encapsulated perfume and non-encapsulated formulations.

The capsules are then reformulated with a '__ copolymer. .... ....... .. -. .. ________.

made of polyether and polyurethane-polyurea polymeric fiber material (commercially available as Lycra). Various amounts of the polymeric material (approximately 1 g to approximately 5 g) were dispersed in 100 g of regular fabric softener compositions containing approximately 3.6% esterquat and approximately 0.38% perfume (either eugenol, phenyl hexanol

<img file="MX348279B_D0019.tif" />

or hexyl salicylate). Containers will shake for ^ K— hours ......—

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ΟΕΙΛ MOREDA »INDWTBiAL until the systems are allowed to balance. The polymeric material was then removed, and the esterquat was tested for perfume molecule content (via HPLC dosing).

Table 2 shows the proportion of perfume molecule extracted from the esterquat aggregates to the fibers of polymeric material, that is, the proportion of the perfume that is absorbed by the polymeric material.

Table 2

<td></td><td>1.0 g of polymeric material</td><td>3.1 g of polymeric material</td><td>5.0 g polymeric material</td>

<td>Eugenol</td><td> 0.24</td><td> 0.45</td><td> 0.57</td>

<td>Phenyl hexanol</td><td> 0.26</td><td> 0.51</td><td> 0.60</td>

<td>Hexyl Salicylate</td><td> 0.34</td><td> 0.63</td><td> 0.69</td>

The results indicate that when the polymeric material is present, the perfume passes from the esterquat to the polymeric material.

The formulation is varied to use the polyether-polyurethane-polyurea copolymer in powder form (preferably in fiber form). The results are

<img file="MX348279B_D0020.tif" />

IMPI βΟΛΠΙΤΟ MEXICANO O * L * MíONEDlAt 'wcwnuxi similar, with deposition slightly mendT ~ ertt! Íertte — in- —— cotton, probably due to the escape of perfume during the drying of the fabric. To improve deposition and reduce perfume loss during drying, the perfume-laden particles are coated with an aminoplast layer (composed of a mixture of melamine-formaldehyde and ureaformaldehyde resins cross-linked with a copolymer of methyl anhydride and methyl vinyl ether, which is commercially available as Gantrez). .

EXAMPLE 3

The nature of the polymeric material can be varied to optimize perfume absorption. Therefore, the polyether can be polytetramethylene oxide (PTHF), polyethylene oxide, polypropylene oxide, or binary or tertiary polymers thereof. The molecular weight of the polyether segments can be varied from about 300 to about 10,000. The length of the polyurethane-polyurea segments can therefore be varied. Polyamide segments can also be used.

EXAMPLE 4

<img file="MX348279B_D0021.tif" />

Divinyl benzene cross-linked polystyrenes were explored as the polymeric material. The partition coefficient of perfume molecules between such cross-linked polystyrene coated with an aminoplast shell (commercially available as Serdolit III) and esterquat was evaluated. The results showed that polystyrene has a high affinity for perfume. When the polystyrene beads are soaked in a perfumed rinse cycle fabric softener composition, it is expected to pump the perfume out of the quat vesicles. A soak test is conducted, various amounts of beads (0.25%, 0.5% and 1%) are added to a rinse cycle fabric softener containing 3.6% EQ and 0.38% of a trio perfume (eugenol, phenyl hexanol and hexyl salicylate). The results showed that the coefficients of division (and therefore affinity to perfume) of the polymeric material comprising polystyrene is much higher than that of the polyether-polyurethane copolymer, as shown in Table 3:

Table 3:

<td></td><td>Copolymer Copolymer Portion of Polyether and Polyurethane</td><td>Polystyrene Material Coefficient Portion</td>

<td>Eugenol</td><td> 1.0</td><td> 6.7</td>

<td>Phenyl hexanol</td><td> 1.1</td><td> 10.3</td>

<td>Hexyl Salicylate</td><td> 1.4</td><td> 6.7</td>

<img file="MX348279B_D0022.tif" />

<img file="MX348279B_D0023.tif" />

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EXAMPLE 5

Table 4 shows the proportion of perfume molecules that remain deposited on the cotton surface from a fabric softener containing 1 and 3% cross-linked polystyrene after formulation of the fabric softening composition:

<td colspan="3">Point of</td><td colspan="3">Concentration of</td>

<td></td><td>Log</td><td>boiling ° C</td><td> 0%</td><td>polystyrene 1%</td><td> 3%</td>

<td>Hexil</td><td>P 5.26</td><td> 290</td><td> 88</td><td> 87</td><td> 88</td>

<td>Salicylate Fen Hexane1</td><td> 3.30</td><td> 258</td><td> 48</td><td> 64</td><td> 80</td>

<td>Eugenol</td><td> 2.30</td><td> 253</td><td> 20</td><td> 42</td><td> 71</td>

<td>Nerol</td><td> 2.65</td><td> 227</td><td> 13</td><td> 42</td><td> 69</td>

<td>Linalool</td><td> 2.43</td><td> 196</td><td> 1.4</td><td> 33</td><td> 61</td>

Table 4 clearly shows the benefit of using cross-linked polystyrene in delivering the medium to low log P of perfume. The results are particularly dramatic for perfumes that are more volatile (have a low boiling point); perfumes such as nerol and even more, linalool, which does not deposit efficiently on its own, is shown to deposit much better in the presence of polystyrene.

<img file="MX348279B_D0024.tif" />