AU2007269428A1 - Cationic polymer stabilized microcapsule composition - Google Patents

Description

WO 2008/005693 PCT/US2007/071782 TITLE OF THE INVENTION CATIONIC POLYMER STABILIZED MICROCAPSULE COMPOSITION CROSS REFERENCE TO RELATED APPLICATIONS [0001] This application claims priority to United States Patent Application No. 11/479,679 filed June 30, 2006, the contents of which are incorporated herein by reference. BACKGROUND OF THE INVENTION [0002] Consumer products, such as fabric care products, personal care products and home care products are well known in the art and usually comprise one or more perfumes to impart the consumer product and/or a substrate treated or applied with the consumer product with a fragrance; however, these perfumes dissipate over time from the consumer product or substrate. Another problem with perfumes in consumer products is that they are released prior to an optimal delivery time, and the user of the consumer product is deprived of experiencing the perfume's fragrance. For example, it is desirable for a perfume to be present on clothes treated with a detergent and/or fabric softener long after such treatment, and there is a tendency for perfumes to evaporate or diffuse from the clothes over time. [0003] Thus attempts have been made to minimize the loss of perfumes due to volatility and evaporation, and to optimize the release of the perfume's fragrance. One such approach has been to encapsulate the perfume within a shell to create a fragrance microcapsule. [0004] The calculated log P (Clog P) of many perfumes is known in the art, and has been reported, for example, in the Ponoma92 database, available from Daylight Chemical Information Systems, Inc. (Daylight CIS) Irvine, CA. Methods of calculating Clog P are also known in the art. Perfumes with lower Clog P values may be more volatile and exhibit higher aqueous solubility than perfumes having higher Clog P values, and are therefore preferred to be used in consumer products. However when lower Clog P materials are encapsulated, they may have a greater tendency to leach out of, or diffuse out of the shell into the consumer product (preventing optimal delivery of fragrances), and the perfumes may eventually diffuse out of the consumer product prior to use by the consumer. [0005] Methods to prevent the leaching of perfumes from fragrance microcapsules have been developed. These may include coating the interior or exterior of the shell with one or more polymers, or incorporation of stabilizing agents in the core. However, there is a continuing need to develop systems that deliver fragrances. More efficient delivery systems, or more stable 1 WO 2008/005693 PCT/US2007/071782 encapsulated perfumes may result in more efficient use of perfumes, thus decreasing manufacturing costs. [0006] When fragrance microcapsules are incorporated in consumer products containing solvents and/or surfactants, e.g., shampoos, stability problems may arise. The encapsulated perfume may leach out of the shell. The shell may also absorb a solvent, surfactant, or any other material in the consumer product, causing the shell's integrity to be compromised. The shell may swell because additional materials diffuse into the shell or the core, or the shell may shrink as materials of the core diffuse out of the shell. Indeed, components of the shell may even diffuse into the consumer product. [00071 Similar considerations apply to the delivery using microcapsules of other materials providing benefits to the consumer, such as flavorants or antibacterial materials. [00081 Thus there is a need to develop compositions suitable for use in compositions that provide for stability of microcapsules encapsulating fragrance or antimicrobial materials. BRIEF SUMMARY OF THE INVENTION [0009] In one embodiment the invention provides a composition comprising: a. a microcapsule comprising a shell encapsulating a material having an average Clog P of at least about 2.5 and more than 60% by weight of the material has a Clog P of at least 3.3, and b. a cross-linked cationic polymer derived from the polymerization of about 5 to 100 mole percent of a cationic vinyl addition monomer, 0 to about 95 mole percent acrylamide, and about 5 to about 500 ppm of a difunctional vinyl addition monomer cross-linking agent. [0010] In another embodiment, the invention provides a method of improving the stability of a product that comprises at least one microcapsule comprising admixing with the product (before, after, or simultaneously with the addition of the at least one microcapsule) a cross-linked cationic polymer derived from the polymerization of about 5 to 100 mole percent of a cationic vinyl addition monomer, 0 to about 95 percent acrylamide, and about 5 to about 500 ppm of a difunctional vinyl addition monomer cross-linking agent, wherein the microcapsule comprises a shell encapsulating a material having an average ClogP of at least 2.5 and more than 60% by weight of the material has a Clog P of at least 3.3. 2 WO 2008/005693 PCT/US2007/071782 DETAILED DESCRIPTION OF THE INVENTION [0010] As used throughout, ranges are used as a shorthand for describing each and every value that is within the range. Any value within the range can be selected as the terminus of the range. Percentages given below are percent of total weight unless otherwise indicated. [0011] The present invention is related to the benefit that is provided by use of a cationic polymer in a composition containing microcapsules, in particular to microcapsules having an average Clog P of at least about 2.5 with more than 60% by weight of the material having a Clog P of at least 3.3. The addition of the cationic polymer to the composition increases the stability of the microcapsule in the composition compared to compositions lacking such cationic polymer. [0012] Perfumes are known in the art and may include odoriferous materials which are able to provide a fragrance to consumer products and/or impart a fragrance to a substrate, e.g.. shampoos and conditioners treat hair. laundry detergents and rinse cycle fabric softeners treat fabrics and clothes, glass cleaners treat glass and hard surfaces, colognes, soaps, deodorants, antiperspirants and shower gels treat skin and hair. Perfumes may also counteract malodors and/or provide a fragrance. The perfumes may be in liquid state at ambient temperature, although solid perfumes may also be useful. Perfumes may include aldehydes, ketones, esters and other chemicals and compounds known in the art, including natural, synthetic perfumes, and mixtures thereof. Perfumes useful for the present invention may have relatively simple compositions or may comprise complex mixtures of natural and synthetic chemical components, all of which are intended to provide an odor or fragrance in consumer products, and/or to the substrate. It is understood in the present application that a perfume may be substituted with flavors known in the art, and that the term perfume, as used herein, also includes flavors. Generally, perfumes may be present in consumer products between 0.00001 - 10%. [0013] Formulations of the invention may comprise unencapsulated fragrance materials in addition to any fragrance material present in the microcapsules. [0014] Fragrance microcapsules are generally known in the art, see ,e.g., WO/2004016234, US 2005/0153135, US 2005/0256027, US2004/0072719A1, US2004/0072720A1, US20040071742A1, US2004/0071746A1, US 6,194,375, WO 02/074430A1: US 6,620.777, the contents of each patent publication are incorporated herein by reference. A fragrance microcapsule generally has a shell which encapsulates a perfume, and optionally other materials, such as solvents, surfactants, hydrophobic polymers, and other 3 WO 2008/005693 PCT/US2007/071782 materials known in the art. The shell may be considered to be made Iup of a tight collection of strands of polymer(s) and may have a diameter less than 1000 ptm, and the shells may have a mean diameter in the range 1 to 500 pm, preferably 1 to 300 tm, more preferably 1 to 50 mrn and most preferably 1 to 10 tLm. The size of the shell may be modified by methods known in the art. Preferred sizes for the shell will depend upon their intended use. [0015] The shell generally prevents leaching of the perfumes from the consumer product. The shell may also bind to substrates, and release the perfume under predetermined conditions, i.e., while fabric is being ironed, a fragrance microcapsule on the fabric bursts due to change in temperature, or while fabric is being worn, a fragrance microcapsule bursts due to friction, shearing, or other physical/mechanical stress caused by the movement of the wearer. [0016] A microcapsule's shell may be made by any of the methods known in the art. The shell may be a polymer or resin known in the art. Shells comprised of polyurethane, polyamide, polyolefin, polysaccaharide, protein, silicone, lipid, modified cellulose, gums, polyacrylate, polyphosphate, polystyrene, and polyesters or combinations thereof may be suitable for use in the present invention. Preferred shells may be an aminoplast which is formed by the reaction of one of more amines known in the art with one or more aldehydes known in the art, such as formaldehyde. In a preferred embodiment, aminoplasts may be prepared by polycondensation. A preferred aminoplast may be a melamine-formaldehyde or urea-formaldehyde condensate. such as melamine resin or urea-formaldehyde resin. Aminoplasts, preferably a melamine resin, may be used singularly or in combination with other suitable amides known in the art. crosslinking agents known in the art (e.g., toluene diisocyanate, divinyl benzene, butane diol diacrylate), and secondary polymers known in the art, such as polymers and co-polymers of maleic anhydride. Aminoplasts may also be mixed resins of urea-formalehyde, maleic anhydride copolymers, and melamine-formalehyde. [0017] The microcapsules of the present invention have a shell, the shell having an inner surface, and an outer surface. The inner surface and/or outer surface of the shell may be coated, e.g., with a polymer. The coating on the inner surface and/or outer surface may improve the barrier properties of the shell and thus may enhance retention of the encapsulated materials in surfactant-containing and/or solvent containing consumer products. [0018] A cationically charged water-soluble polymer known in the art can be coated on shell. The water-soluble polymer can also be an amphoteric polymer with a ratio of cationic and 4 WO 2008/005693 PCT/US2007/071782 anionic functionalities resulting in a net total charge of zero and positive. Methods for coating the cationically charged polymer onto the microcapsule are also known in the art. [0019] The application of a coating to the inner surface of the shell capsules may be carried out by a number of methods known in the art. One approach known in the art involves the use of a suitable material for the coating which is insoluble in the material to be encapsulated, but can be dissolved in a water soluble solvent e.g., ethanol, carbitol, which is miscible with the material to be encapsulated. The coating material, typically a polymer, is dissolved in the solvent and then the solution is dissolved in the material to be encapsulated. The material to be encapsulated is then emulsified into a standard aminoplast capsule forming aqueous solution. As the emulsion forms, the solvent is lost to the water and the polymer precipitates out from solution at the surface of the emulsion droplets, forming a film at the interface of water/material to be encapsulated. An encapsulation process known in the art may then be carried out and the coating may be deposited on the inner surface of the shell. [0020] In another method known in the art, a coating material, e.g., silicone, used may be immiscible with materials to be encapsulated and immiscible with water, and is capable of forming a thin film at the water interface. A shell encapsulate comprising a coating of silicone on the inner surface of the shell can be prepared by dispersing the material to be encapsulated within the silicone and then emulsifying this mixture so that an emulsion is formed where droplets of encapsulated material are surrounded by a thin film of silicone. The encapsulation process is then carried out as known in the art. Alternatively, a thin film may be formed at the surface by dispersing the material to be encapsulated in water, adding the second material e.g., silicone and allowing it to coat the encapsulating material droplets subsequently. An inner surface coating may also be made from a film-forming polymer known in the art, for example: poly(ethylene-maleic anhydride), povidones, waxes e.g. carbowax, polyvinylpyrrolidone (PVP) and its co-polymers such as polyvinylpyrrolidone-ethyl acrylate (PVP-EA). polyvinylpyrrolidone-vinyl acrylate, polyvinylpyrrolidone methylacrylate (PVP-MA), polyvinylpyrrolidone/vinyl acetate, polyvinyl acetal, polyvinyl butyral, polysiloxane, poly(propylene maleic anhydride), maleic anhydride derivatives and co-polymers of the above, e.g. polyvinyl methyl ether/maleic anhydride. Preferably, the inner wall coating comprises polysiloxane, PVP or PVP co-polymers, more preferably PVP or PVP co- polymers, and even more preferably PVP co-polymers, particularly PVP-MA or PVP-EA. 5 WO 2008/005693 PCT/US2007/071782 [0021] A coating may be applied to the outer surface of a shell techniques known in the art, such as by including spraying, fluid bed coating, or precipitating. For example a coating, e.g., of a polymer, may be precipitated from aqueous solution to condense onto the outer surface of the shell or microcapsule, e.g., in the form of a capsules slurry, with precipitation being caused by change of temperature, pH. addition of salt, and other variables and conditions known in the art. The shell capsule to be coated is thus formed in a separate first step, prior to the application of the coating to the outer surface of the shell wall. Depending on the composition of the outer surface coating, a coated shell capsule may be prepared for example, by coacervation or polycondensation. [0022] The outer surface coating may comprise high molecular weight, film- forming polymers known in the art, which may optionally be cross-linked. "High molecular weight" is meant a molecular weight average of greater than 2000 Da, preferably greater than 4000 Da, more preferably greater than 5000 Da. The polymer maybe water-soluble or water- insoluble, preferably water-soluble. Suitable polymers for use may include, polyvinyl alcohol (PVOH), styrene-butadiene latex, gelatin, gum arabic, carboxymethyl cellulose, carboxymethyl hydroxyethyl cellulose, hydroxyethyl cellulose, other modified celluloses, sodium alginate, chitosan, casein, pectin, modified starch, polyvinyl acetal, polyvinyl butyral, polyvinyl methyl ether/maleic anhydride, PVP and its co-polymers (e.g. polyvinylpyrrolidone/vinyl acetate (PVP/VA), poly(vinyl pyrrolidone/dimethylaminoethyl methacrylate) (PVP/DMAEMA), poly(vinyl pyrrolidone/methacrylamidopropyl trimethyl ammonium chloride), melamine formaldehyde and urea-formaldehyde. Preferably. the outer surface of the shell is coated with PVOH, PVP or a PVP co-polymer. [0023] A preferred coated shell may be an aminoplast capsule having a coating of PVOH, PVP or a co-polymer PVP (preferably PVP/DMAEMA) on the outer surface of the shell and/or a coating of a film- forming polymer (preferably PVP-EP) on the inner surface. [0024] The coating (inner and/or outer) may be cross-linked in any known manner, e.g., by interfacial cross-linking. A shell capsule useful herein may have more than one coating on the outer surface of the shell. [0025] Coated shell capsules typically have a wall thickness in the range of about 0.01 to about 30 pm. preferably about 0.01 to about 5 jtm. more preferably about 0.03 to about 1 pm, most preferably about 0.03 to about 0.5 pm. The wall thickness may be regulated and controlled 6 WO 2008/005693 PCT/US2007/071782 according to the encapsulate size and by varying the relative proportions of coating and shell polymer. The weight ratio of coating to shell wall is typically in the range of about 0.01 to about 10:1, preferably about 0.1:1 to about 10:1, more preferably about 0.1:1 to about 3:1. [0026] Typically, the weight ratio of polymer shell wall material to encapsulated material is in the range of about 1:10 to about 3:2 and preferably in the range of about 1:10 to about 1:2. The coating on the inner surface and/or outer surface will increase these weight ratios. [0027] When the shell is coated, materials having an average Clog P value equal to or greater than 2.5 may be encapsulated, preferably within the range of about 3 to about 5. Materials used in uncoated microcapsules may include materials wherein at least about 60% have a Clog P equal to or greater than about 3.3, preferably greater than about 4. By "average Clog P" is meant the average Clog P for all of the encapsulated materials. Thus the average Clog P of the encapsulated materials may be raised, for example, by adding a solvent having a high ClogP, e.g., about 6 or greater, wherein the solvent is miscible with the other encapsulated materials. [0028] One or more perfumes may be used in the present invention as a mixture of perfumes. Thus, for microcapsules having a shell without a coating, a mixture of perfumes greater than about 60 weight percent of the fragrance materials have a Clog P of greater than about 3.3, preferably more than about 80 weight percent of the fragrances have a Clog P value of greater than about 4.0, and more preferably, more than about 90 weight percent of the fragrances have a Clog P value of greater than about 4.5 may be used. [0029] The microcapsule contains a core within the shell, and the core comprises a perfume or other benefit agent, such as a flavorant or antibacterial material, and may optionally contain other materials known in the art, for example, hydrophobic solvents such as triglyceride oil, mono and diglycerides, mineral oil, silicone oil, diethyl phthalate, polyalphaolefins, fatty alcohols, castor oil and isopropyl myristate. The solvent materials may be miscible with the benefit agents. For microcapsules having a shell without a coating on the inner or outer surface, suitable solvents include those having reasonable affinity for the perfume, and the solvent may have a Clog P greater than 3.3, preferably greater than 6 and most preferably greater that 10. A preferred solvent may be isopropyl myristate. A preferred solvent may also be silicone, such polydimethylsiloxane and polydimethylcyclosiloxane. In another embodiment of the present invention, a preferred solvent may be diethyl phthalate. The solvent may be greater than about 30 7 WO 2008/005693 PCT/US2007/071782 weight percent, preferably greater than about 50 weight percent and more preferably greater than about 70 weight percent of the core. [0030] It is known in the art that the addition of hydrophobic polymers in a microcapsule may also improve stability of the microcapsule by slowing diffusion of the perfume from the shell. The amount of the hydrophobic polymer may be less than 80% of the microcapsule by weight, preferably less than 50%, and most preferably less than 20%. A hydrophobic polymer may be ethyl cellulose, hydroxypropyl cellulose, cellulose acetate butyrate, ethylene vinyl acetate, polystyrene, and PVP and ester terminated polyamides or amrnide terminated polyamides. [0031] As previously described, when microcapsules are incorporated in certain solvents and/or surfactant- containing consumer products. e.g., shampoos, stability problems may arise. Thus in the present invention, a cationic polymer is added to the consumer product to increase the stability of the microcapsule. [0032] The cationic polymer in the present invention is a cross-linked polymer which is cross-linked using a cross-linking agent of a difunctional vinyl addition monomer at a level of about 5-500 ppm, preferably about 70 to about 300 ppm, preferably about 75 to about 200ppm, and most preferably of from about 80 to about 150 ppm. The cationic polymer may be a cationic vinyl polymer. A cationic vinyl polymer may be derived from the polymerization of from about 5 to 100 mole percent of a cationic vinyl addition monomer and 0 to about 95 mole percent of acrylamide. The difunctional vinyl addition monomer may be a polyethylene glycol diacrylic ester having a weight average molecular weight of from 300 to 3,000. [00331 The cationic polymer may be derived from the polymerization of about 5 to 100 mole percent of a cationic vinyl addition monomer, 0 to about 95 mole percent of acrylamide, and about 70 to about 300 ppm of a difunctional vinyl addition monomer crosslinking agent. The difunctional vinyl addition monomer may be a polyethylene glycol diacrylic ester having a weight average molecular weight of about 300 to about 3,000. [0034] The cationic polymer may also be a cross-linked cationic vinyl addition polymer derived from the polymerization of about 15 to about 70 mole percent of a quaternary ammonium salt of dimethyl/aminoethylmethacrylate and about 30 to about 85 mole percent of acrylamide, and about 0.005 to about 0.025 weight percent of the polyethylene glycol diacrylic ester. The polyethylene glycol diacrylic ester may be polyethylene glycol dimethacrylate. 8 WO 2008/005693 PCT/US2007/071782 [0035] The cationic polymer may be prepared as water in oil emulsions, wherein the cross-linked polymers are dispersed in the oil, preferably a mineral oil. A cationic polymer may be a cross-linked copolymer of a quaternary ammonium acrylate or methacrylate in combination with an acrylamide comonomer. Additional description of cationic polymers useful in the present invention may be found in U.S. Patent Nos. 4,806,345 and 6,864,223, which are incorporated herein by reference. [0036] A composition may comprise about 0.001 % to about 40% total weight of the cationic polymer, preferably about 0.01% to about 10%, more preferably, about 0.01% to about 5%. The amount of cationic polymer present will depend upon the composition and the microcapsule used therein. The cationic polymer may be admixed to the consumer product before, during or after the addition of a microcapsule to the consumer product. [0037] As described herein, the cationic polymer is well suited for use in a variety of well-known consumer products comprising a microcapsule, such as oral care products, toothpastes, mouthwashes, personal care products, lotions, creams, shampoos, conditioners, hair gel, antiperspirants, deodorants, shaving creams, hair spray, colognes, body wash, home care products, laundry detergent, fabric softeners, liquid dish detergents, tumble dryer sheets, automatic dish washing detergents, and hard surface cleaners. These consumer products may employ surfactant, solvents and emulsifying systems that are well known in the art. In the consumer product base, a fragrance is used to provide the consumer with a pleasurable fragrance during and after using the product or to mask unpleasant odors from some of the functional ingredients used in the product. As stated above, a problem with the use of encapsulated fragrance in product bases is the loss of the fragrance before the optimal time for fragrance delivery. [0038] In the present invention, the microcapsule may be in an aqueous solution of a consumer product. Alternatively, the microcapsule may be in the continuous phase of an oil-in water emulsion of a consumer product. Alternatively, the microcapsule may be in the discontinuous phase of an oil-in-water emulsion of a consumer product. Alternatively, the microcapsule may be in the discontinuous phase of a water-in-oil emulsion of a consumer product. Alternatively, the microcapsule may be in the continuous phase of a water-in-oil emulsion of a consumer product. 9 WO 2008/005693 PCT/US2007/071782 [0039] Consumer products may be made using an aqueous base containing a surfactant, although some products use glycols, polyhydric alcohols, alcohols, or silicone oils as the dominant solvent or carrier. Suitable surfactant agents for use in the present invention include those surfactants that are commonly used in consumer products such as laundry detergents, fabric softeners and the like. The products commonly include cationic surfactants which also are used as fabric softeners; as well as nonioinic and anionic surfactants which are known in the art. Surfactants are normally present at levels of about 1 to 30 weight %. In some instances the surfactant loading may be more than 85, typically more than 95 and greater than about 99 weight % of the formulated product. [0040] The present invention is further illustrated for use in a consumer product, such as a fabric softener composition. Fabric softener compositions are known in the art, and contain a fabric softening component, and other optional materials such as perfumes, chelators, preservatives, dyes, soil release polymers, and thickeners. Other optional ingredients may also include solvents, alcohols, amphoteric and non-ionic surfactants, fatty alcohols, fatty acids, organic or inorganic salts, pH buffers, antifoams, germicides, fungicides, antioxidants, corrosion inhibitors, enzymes, optical brighteners, antifoams, and other materials known in the art. [0041] A fabric softener composition may be substantially free of anionic surfactants known in the art, such as, lithium dodecyl sulfate, or sodium dodecyl sulfate. By substantially free is meant that the fabric softener composition contains less than 5% weight of anionic surfactant, preferably less than 1% by weight, more preferably less than .5% by weight and still more preferably less than 0.1% by weight of an anionic surfactant. [0042] A fabric softener composition may be substantially free of water soluble builder salts known in the art. such as alkali metal phosphates, such as sodium phosphate and potassium phosphate. By substantially free is meant that the fabric softener composition contains less than 5% weight of a builder salt, preferably less than 1% by weight, more preferably less than 0.5% by weight and still more preferably less than 0.1% by weight an water soluble builder salt. [0043] Fabric softening components in fabric softener compositions are well known in the art. and may include cationic surfactants, quaternary ammonium salts (acyclic quaternary ammonium salts, ester quaternary ammonium salts, cyclic quaternary ammonium salts, diamido quaternary ammonium salts, biodegradable quaternary ammonium salt, polymeric ammonium salts), polyquats, tertiary fatty amines, carboxylic acids, esters of polyhydric alcohols, fatty 10 WO 2008/005693 PCT/US2007/071782 alcohols, ethoxylated fatty alcohols, alkyphenols, ethoxylated alkyphenols, ethoxylated fatty amines, difatty, ethoxylated monolycerides, ethoxylated diglycerides, mineral oils, clays, and polyols. [0044] A fabric softener composition may comprise about 0.01% to about 35% by weight of one or more fabric softening components. Preferably, the present invention may comprise about 0.5% to about 25% weight of a fabric softening component. Optionally, the present invention may comprise about 1.5% to about 12% of a fabric softening component. Optionally, the present invention may comprise about 15% to about 24% of a fabric softening component. [0045] The amount of the components in a fabric softener composition will depend on the purpose of the formulation, i.e., whether the formulation concentrated or dilute. Thus, the fabric softening component may, for example, be about 0.1% to about 50% of the total weight of the composition, e.g., about 10% to about 25% for a concentrated composition and about 1 to about 10% for a dilute composition. The fabric softener composition may also have one or more chelators, dyes, fatty alcohols, preservatives and/or perfumes, and/or other ingredients as known in the art. [0046] A fabric softening component may be an esterquat (or mixture of esterquats) having the formula of structure 1 R2 R+ R N 0

X

Rj \ 11 (CH2)q-O-C-R 4 STRUCTURE 1 wherein Ri represents -(CH 2

),R

6 where R 6 represents benzyl, phenyl. (Ci-C4)-alkyl substituted phenyl, OH or H: R2 and R 3 represent -(CH 2 )s-R 5 where R 5 represents an acyloxy group containing from 8 to 22 carbon atoms, benzyl, phenyl. (CI -C4)-alkyl substituted phenyl. OH or H;

R

4 represents an aliphatic hydrocarbon group having from 8 to 22 carbon atoms; q, s, and t, each independently, represent an integer from 1 to 3; and X- is a softener compatible anion. 11 WO 2008/005693 PCT/US2007/071782 [0047] A particular softener for use in the present invention is produced by reacting two moles of fatty acid methyl ester with one mole of triethanolamine followed by quaternization with dimethyl sulfate (further details on this preparation method are disclosed in US 3,915,867, which is incorporated herein by reference). The reaction products are distributed as follows: (a) 50% diesterquat material; (b) 20% monoesterquat: and (c) 30% triesterquat. [0048] Depending on the esterification process conditions, the distribution of the three species (mono, di and tri) may vary. The esterquat compounds described herein are prepared by quaternizing the product of the condensation reaction between a fatty acid fraction containing at least one saturated or unsaturated linear or branched fatty acid, or derivative, and at least one functionalized tertiary amine, wherein the molar ratio of the fatty acid fraction to tertiary amine is about 1.7 : 1. The method of manufacture for such a esterquat surfactant is described in US Patent 5,637,743 (Stepan). the disclosure of which is incorporated herein by reference. [0049] The aforementioned molar ratio will determine the equilibrium between the mono. di and tri-esterquat compounds in the products. For example, using a molar ratio of about 1.7 results in a normalized distribution of about 34% mono-esterquat, about 56% of di-esterquat and about 10% of tri-esterquat which is a fatty ester quat compound in accordance with the invention. On the other hand, for example, using a molar ratio of about 1.96 results in a normalized distribution of about 21% mono-esterquat, 61% of di-esterquat and 18% of tri esterquat. [0050] A preferred fabric softening component may thus include a quaternized fatty acid triethanolamine ester salt, e.g., a triethanolamine-esterquat tallow. A preferred fabric softening component of the present invention may include a di-alkyl ester of triethanol ammonium methyl sulfate, or a dihydrogenated tallowoylethyl hydroxyethylmonium methosulfate. Fabric softening components may be purchased from Kao Corporation under the product name Tetranyl L1/90 or Tetranyl AT1-75. [0051] Fabric softener compositions may also comprise soil release polymers (SRP's). SRP's are well known in the art, and may include polymers which are absorbed onto fabric fibers where they counteract resoiling of the fibers. The polymers may include polyesters and co polymers of terephthalic acid, polyesters of and co-polymers of ethylene glycol, copolymers of ethylene glycol and benzene, and polyethylene terephthalate. The polymers may include 12 WO 2008/005693 PCT/US2007/071782 nonionic polyesters. The polymers may be modified whereby a portion of the ethylene glycol is removed and replaced with a high molecular weight hydroxy-terminated polyethylene glycol. [0052] Chelating agents are well known in the art, and may be present at a level of at least about 0.001%, by weight, of the fabric softening composition, preferably about 0.001% to about 1%, more preferably about 0.01% to about 0.5%, more preferably about 0.06% - 0.1% by weight. The chelating agents may be selected from among amino carboxylic acid compounds and organo aminophosphonic acid compounds, and mixtures of the same. Suitable amino carboxylic acid compounds may include: ethylenediamine tetraacetic acid, N hydroxyethylenediamine triacetic acid, nitrilotriacetic acid, and diethylenetriamine pentaacetic acid. Suitable organo aminophosphonic acid compounds may include methylenephosphonic acid, 1-hydroxyethane 1.1-diphosphonic acid, and aminotrimethylene phosphonic acid. A preferred chelating agent may be an aminotrimethylene phosphonic acid, which may be obtained from Solutia, Inc. (St. Louis. Missouri, USA) as Dequest 2000. [0053] Preservatives are well known in the art, and may include lactic acid, formaldehyde, or other preservatives known in the art. A fabric softener composition may comprise 0% to about 10% weight of a preservative, preferably, about 0.01% to about 2%, more preferably about 0.05% to about 0.5%. A preferred preservative in the present invention may be lactic acid. [0054] Fatty alcohols and aliphatic alcohols are known in the art. Fatty alcohols may have carbon chain which are fully saturated or unsaturated. Preferred fatty alcohols include Clo 0 C 28 alcohols, preferably C 16 - 18.s, C 13

-C

15 alcohols, and mixtures thereof. A fabric softener composition may comprise 0% to about 10% weight of a fatty alcohol, preferably about 0.1% to about 5%. and more preferably about 0.1% to about 0.5% of a fatty alcohol. [0055] Dyes are well known in the art and may comprise 0% to about 5% of a product. [0056] In another embodiment, the invention provides a method of delivering a fragrance or antimcrobial material in a product comprising admixing any of compositions into a consumer product. The consumer product may be a oral care product, toothpaste, mouthwash, personal care product, lotion, cream, shampoo, conditioner, hair gel, antiperspirant, deodorant. antiperspirant and deodorant, shaving cream, hair spray, cologne, body wash, home care product, laundry detergent. fabric softener, liquid dish detergent, tumble dryer sheet, automatic dish detergent, or hard surface cleaner. 13 WO 2008/005693 PCT/US2007/071782 EXAMPLES Example 1 [0057] The following compositions are prepared by mixing in deionized water to create an emulsion (percentages are percentage of total weight): FC#1 FC#2 TEA-esterquat tallow 8.667% 8.667% Cationic polymer 0.268% Amino trimethylene 0.1% 0.1% phosphonic acid Lactic acid 0.063 % 0.063 % Fragrance microcapsule 3.6% 3.6% Water Balance Balance [0058] Water and TEA-esterquat tallow are each separately heated to 65 0 C. Add amino trimethylene phosphonic acid to the water and mix. Add TEA-esterquat the water at a rate of about between 25 to 40 grams per minute. Mix for 10 minutes, and cool while mixing in an ice/water bath until a temperature of 35 0 C is reached. Add lactic acid and mix. Add cationic polymer, and mix for 10 minutes. Fragrance microcapsules are added, and the solution is mixed for an additional 30 minutes. Example 2 [0059] Cotton terry towels are washed in laundry washing machines with equal amounts of compositions FC#1 and FC#2. Following washing, the towels are line dried for one day at room temperature. A panel of 20 judges is asked to evaluate the towels washed with FC#1 and FC#2 according to odor. 63% of the judges preferred towels washed with FC#1. The towels are then rubbed and judges are asked to reevaulate the towels. 70% of the judges preferred FC#1. The results show that the towels washed in FC#1 with the cationic polymer with the fragrance microcapsules gave an increased fragrance. 14 WO 2008/005693 PCT/US2007/071782 Example 3 [0060] The following compositions are prepared by mixing in deionized water to create an emulsion (percentages are percentage of total weight): FC#3 FC#4 Tetranyl L1/90 8.667% 8.667% Cationic polymer 0.268% 0.268% Dequest2000 0.1% 0.1% Lactic acid 0.063 % 0.063 % Fragrance 0.99% Fragrance microcapsule - 5.723% (0.99% (17.3% fragrance) fragrance) Water Balance Balance [0061] Water and Tetranyl L1/90 are each separately heated to 65°C. Add Dequest2000 to the water and mix. Add Tetranyl L1/90 to the water at a rate of about between 25 to 40 grams per minute. Mix for 10 minutes, and cool while mixing in an ice/water bath until a temperature of 35 0 C is reached. Add lactic acid and mix. Add cationic polymer, and mix for 10 minutes. Fragrance microcapsules and fragrance are added to respective formulations, and the solutions are mixed for an additional 30 minutes. Example 4 [0062] Cotton terry towels are washed in laundry washing machines with equal amounts of compositions FC#3 and FC#4. Following washing, the towels are stored for 1 week at temperature for 1 week, 3 months at 35 0 C, and one month at 43 0 C. Following storage, a panel of 20 judges is asked to rate the intensity of the perfume on the towel, and the intensity of the perfume on the towel after rubbing the towel several times. The results are shown in the chart below. The towels washed in FC#4 with the encapsulated fragrance with the cationic polymer outperformed the towels washed in FC#3 without the encapsulated fragrance. 15 WO 2008/005693 PCT/US2007/071782 8 1 Week Aged at 3 Months Aged 1 Month Aged 7 Room Temp. at 35 oC at 43 'C 6 5] " 4 -l Unrubbed S3 Rubbed 0 FC#3 FC#4 FC#3 FC#4 FC#3 FC#4 [0063] The matters set here are offered by way of illustration only and not as limitations. While particular embodiments have been shown and described, it will be apparent to those skilled in the art that changes and modifications may be made without departing from the broader aspects of invention. The actual scope of the protection sought is intended to be defined in the following claims when viewed in their proper perspective based on the prior art. 16

Claims (34)

1. A composition comprising: (a) a microcapsule comprising a shell encapsulating a material having an average Clog P of at least about 2.5 and more than 60% by weight of the material has a Clog P of at least 3.3, and (b) a cross-linked cationic polymer derived from the polymerization of about 5 to 100 mole percent of a cationic vinyl addition monomer, 0 to about 95 mole percent acrylamide, and about 5 to about 500 ppm of a difunctional vinyl addition monomer cross linking agent.

2. The composition of claim 1, wherein the shell has an inner surface and an outer surface and the shell has a coating of a polymer film on the inner surface, the outer surface, or both the inner surface and the outer surface.

3. The composition of claim 1, wherein the cross-linking agent is at a level of 70 to 200 ppm.

4. The composition of claim 1, wherein the cross-linking agent is at a level of 80 to 150 ppm.

5. The composition of claim 1, wherein the cross-linked cationic polymer comprises a quaternary ammonium salt of an (meth)acrylate.

6. The composition of claim 1, wherein the cross-linked cationic polymer comprises a quaternary ammonium salt of dimethyl aminoethyl methacrylate.

7. The composition of claim 1, wherein the shell comprises an aminoplast.

8. The composition of claim 7, wherein the amnioplast comprises a resin of melamine and formaldehyde. 17 WO 2008/005693 PCT/US2007/071782

9. The composition of claim 1, wherein the shell comprises a mixed resin of urea formaldehyde resin, maleic anhydride copolymers, and melamine resin.

10. The composition of claim 1, wherein the material has an average ClogP value of equal to or greater than 3.3.

11. The composition of claim 2, wherein the inner surface has the coating with the polymer film.

12. The composition of claim 11, wherein the polymer is selected from the group consisting of poly(ethylene-maleic anhydride), polyamine, wax, polyvinylpyrrolidone, polyvinylpyrrolidone co-polymers, polyvinylpyrrolidone-ethyl acrylate, polyvinylpyrrolidone vinyl acrylate, polyvinylpyrrolidone methylacrylate, polyvinylpyrrolidone/vinyl acetate, polyvinyl acetal, polyvinyl butyral, polysiloxane, poly(propylene maleic anhydride), maleic anhydride derivatives, co-polymers ofmaleic anhydride derivatives, and combinations thereof.

13. The composition of claim 2, wherein the outer surface has the coating of the polymer film comprising an outer polymer.

14. The composition of claim 13, wherein the outer polymer is selected from the group consisting of polyvinyl alcohol, styrene-butadiene latex, gelatin, gum Arabic, carboxymethyl cellulose, carboxymethyl hydroxyethyl cellulose, hydroxyethyl cellulose, other modified celluloses, sodium alginate, chitosan, casein, pectin, modified starch, polyvinyl acetal, polyvinyl butyral, polyvinyl methyl ether/maleic anhydride, polyvinyl pyrrolidone and its co polymers, poly(vinyl pyrrolidone/methacrylamidopropyl trimethyl ammonium chloride), polyvinylpyrrolidone/vinyl acetate, poly(vinyl pyrrolidone/dimethylaminoethyl methacrylate, and combinations thereof

15. The composition of claim 1, wherein the material comprises a fragrance material. 18 WO 2008/005693 PCT/US2007/071782

16. The composition of claim 1, wherein the material comprises an antimicrobial material.

17. The composition of claim 1 further comprising in the microcapsule with the material a solvent having a ClogP of at least 6 that is miscible with the material.

18. The composition of claim 1, wherein the material comprises a flavorant material.

19. The composition of claim 1 further comprising at least one fabric softening component.

20. The composition of claim 19, wherein the fabric softening component is an esterquat.

21. The composition of claim 20, wherein the esterquat is a compound or mixture of compounds of Structure 1 R 2 \ /R3 \N O X 1-00 R 1 I I (CH 2 )q-O-C-R 4 STRUCTURE 1 wherein R 1 represents -(CH2)tR 6 where R 6 represents benzyl, phenyl, (Cl -C4)-alkyl substituted phenyl, OH or H; R 2 and R 3 represent -(CH2)s-R 5 where R 5 represents an acyloxy group containing from 8 to 22 carbon atoms, benzyl, phenyl, (C 1-C4)-alkyl substituted phenyl, OH or H: R 4 represents an aliphatic hydrocarbon group having from 8 to 22 carbon atoms; q, s, and t, each independently, represent an integer from 1 to 3; and X is a softener compatible anion. 19 WO 2008/005693 PCT/US2007/071782

22. The composition of claim 20, wherein the esterquat comprises a mixture of the mono-, di-alkyl and tri-alkyl esters of triethanol ammonium methyl sulfate.

23. The composition of claim 22, wherein the distribution of the ester forms is a) monoester: 15-40% b) diester: 50-65% c) triester: 5-30%.

24. The composition of claim 22, wherein the distribution of the ester forms is a) monoester: 32-36% b) diester: 54-58% c) triester: 8-12%.

25. The composition of claim 22, wherein the distribution of the ester forms is a) monoester: 19-23% b) diester: 59-63% c) triester: 16-20%.

26. The composition of claim 22, wherein the distribution of the ester forms is a) monoester: 18-22% b) diester: 48-52% c) triester: 28-32%.

27. The composition of claim 19, wherein the fabric softening component is about 0.1% to about 50% of the total weight of the composition.

28. The composition of claim 19, wherein the microcapsule encapsulates fragrance materials and is present in an amount of about 0.0001% to about 10% of the total weight of the composition. 20 WO 2008/005693 PCT/US2007/071782

29. A method of improving the stability of a product that comprises at least one microcapsule comprising admixing with the product a cross-linked cationic polymer derived from the polymerization of about 5 to 100 mole percent of a cationic vinyl addition monomer, 0 to about 95 percent acrylamide, and about 5 to about 500 ppm of a difunctional vinyl addition monomer cross-linking agent, wherein the microcapsule comprises a shell encapsulating a material having an average ClogP of at least 2.5 and more than 60% by weight of the material has a Clog P of at least 3.3.

30. The method of claim 29, wherein the shell has an inner surface and an outer surface and the shell has a coating of a polymer film on the inner surface, the outer surface, or both the inner surface and the outer surface.

31. The method of claim 29, wherein the cross-linking agent is at a level of 70 to 300 ppm.

32. The method of claim 29, wherein the cross-linking agent is at a level of 80 to 150 ppm.

33. The method of claim 29, wherein the cross-linked cationic polymer comprises a quaternary ammonium salt of a (meth)acrylate.

34. The method of claim 29, wherein the cross-linked cationic polymer comprises a quaternary ammonium salt of dimethyl aminoethyl methacrylate. 21