Method of making personal care formulation

Abstract

A method of making a personal care formulation is provided, comprising: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSi(R1)3 group; wherein each R1 is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a C1-4 alkoxy group; and wherein the silylated compound has a viscosity of ≤ 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate.

Description

Attorney Docket No.86610-WO-PCTMETHOD OF MAKING PERSONAL CARE FORMULATION

[0001] The present invention relates to a method of making a personal care formulation. In particular, the present invention relates to a method of making a personal care formulation comprising: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSi(R' p group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a CM alkoxy group; and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate.

[0002] Silicone fluids (e.g., dimethicones, cyclomethicones, phenyl trimethicones) have demonstrated outstanding physicochemical and sensory properties that make them desirable for use in an array of personal care products. Silicone fluids may serve a variety of functions in personal care products including as earners for other cosmetic ingredients, as emollients, as conditioning agents and as anti-soaping agents. Silicone fluids incorporated into skin care formulations provide a variety of benefits including improved slip, reduction of tack, impartation of emolliency, reduction of soaping during rubbing among other improved feel characteristics of the formulation. Silicone fluids incorporated into hair care formulations as conditioners provide reduced combing force, reduced hair friction, improved feel and increased hair shine.

[0003] Notwithstanding, there has been concern expressed by some about the use of silicone fluids in cosmetics and there is a recent trend to seek biosourced, biodegradable alternatives to silicones for use in personal care products. However, proposed entirely silicone free alternatives identified to date have failed to reach the same level of performance as that associated with the silicone counterparts.

[0004] Castor oil has been proposed as a partial replacement for silicones in some personal care products to offer a more natural alternative. However, castor oil is difficult to formulate into personal care products, particularly at high concentrations because of its high viscosity and sticky texture. Also castor oil tends to impart a heavy and greasy feel on the skin and presents undesirable product consistency and user experience.

[0005] Accordingly, there remains a need for alternative ingredients to silicone fluids that provide comparable performance but while offering an alternative chemistry with reduced silicon content and / or an improved biosourced / biodegradability profile, which alternativeAttorney Docket No.86610-WO-PCTchemistry is readily incorporated into personal care formulations without imparting a heavy and greasy feel on the skin.

[0006] The present invention provides a method of making a personal care formulation comprising: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSi(R' J i group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a CM alkoxy group; and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate.

[0007] The present invention provides a method of making a personal care formulation comprising: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSilR1)? group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a C1-4 alkoxy group; and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate; and with any one or more of the following provisos (i)-(xi): (i) with the proviso that the silylated compound has a log P of > 10; (ii) with the proviso that the personal care formulation comprises < 0.1 equivalent isocyanate groups with respect to the total number of hydroxyl groups in the silylated compound; (iii) with the proviso that the personal care formulation further comprises a humectant and / or emulsifier selected from the group consisting of glycerin, sorbitol, monoglycerides, lecithins, glycolipids, fatty acids, fatty acid salts (e.g., glyceryl stearate), polysaccharides, sorbitan esters, polysorbates (e.g., Polysorbate 20, Polysorbate 40, Polysorbate 60, and Polysorbate 80), natural oils (e.g., Jojoba oil) and mixtures thereof; (iv) with the proviso that the personal care formulation comprises < 0.005 wt%, based on weight of the personal care formulation, of a maleated natural oil; (v) with the proviso that the silylated compound comprises 0 maleated functionalities per molecule of the silylated compound; (vi) with the proviso that the personal care formulation comprises < 0.005 wt%, based on weight of the personal care formulation, of silylated compound having > 4 carbonyl groups (C=O) per molecule; (vii) with the proviso that the fatty acid esterAttorney Docket No.86610-WO-PCTcomprises 50 to 100% biobased carbon content determined according to ASTM 6866-24, Method B; (viii) with the proviso that 25 to 100 % of the hydroxyl groups of the fatty acid ester have been converted to -OSi R1)^ groups in the silylated compound; (ix) with the proviso that each R1is independently selected a C1-2 alkyl group; (x) with the proviso that each R1is a methyl group; and (xi) with the proviso that the personal care formulation further comprises a personal care additive; wherein the personal care additive is selected from the group consisting of selected from the group consisting of an absorbent; an aesthetic enhancer (e.g., starch); an alpha hydroxy acid; an antiaging agent; an antidandruff agent; an antifungal; an antimicrobial agent; an antioxidant (e.g., butyl ated hydroxytoluene); an antiseptic; an antistatic agent; a bioactive agent; a bleaching agent; a chelating agent; a cleaning surfactant; a colorant; a conditioning agent (e.g., silicone, polyquatemium. cationic guar); a dye; an emollient; a fdm former (e.g., water proofing agent); a fixative polymer; a foaming agent; a fragrance; a hard particle; a humectant and / or emulsifier (e.g., glycerin, sorbitol, monoglycerides, lecithins, glycolipids, fatty alcohols, fatty acids, polysaccharides, sorbitan esters, polysorbates (e.g., Polysorbate 20, Polysorbate 40, Polysorbate 60, and Polysorbate 80), glycols (e.g., propylene glycol)); a lubricating agent; a nonionic surfactant other than an acyclic branched alcohol ethoxy glucoside surfactant; an opacifier; a pearlizing agent; a penetrant; a pH adjusting agent; a pigment; a plant extract; a preservative (e.g., benzoic acid, sorbic acid, phenoxyethanol); a protein / amino acid; a rheology modifier; a salt (e.g., NaCl); a sensory modifier; a slip agent; a soap; a soft particle; a sunscreen additive; a suspending agent; a UV light inhibitor; a vitamin and mixtures thereof.

[0008] The present invention provides a method of making a personal care formulation comprising: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSitR 'p group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a C1-4 alkoxy group; and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate; and wherein the silylated compound has a log P of > 20.

[0009] The present invention provides a method of making a personal care formulation comprising: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixtureAttorney Docket No.86610-WO-PCTthereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSilR1^ group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a C1-4 alkoxy group; and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate; and wherein the personal care formulation comprises < 0.1 equivalent isocyanate groups with respect to the total number of hydroxyl groups in the silylated compound.

[0010] The present invention provides a method of making a personal care formulation comprising: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSitR ')3 group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a C1-4 alkoxy group; and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate; and wherein the personal care formulation comprises < 0.005 wt%, based on weight of the personal care formulation, of a maleated natural oil.

[0011] The present invention provides a method of making a personal care formulation comprising: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSilR1)? group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a C1-4 alkoxy group; and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate; and wherein the silylated compound comprises 0 maleated functionalities per molecule of the silylated compound.

[0012] The present invention provides a method of making a personal care formulation comprising: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been convertedAttorney Docket No.86610-WO-PCTto an -OSiiR 'p group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a CM alkoxy group; and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate; and wherein the personal care formulation comprises < 0.005 wt%, based on weight of the personal care formulation, of silylated compound having > 4 carbonyl groups (C=O) per molecule.

[0013] The present invention provides a method of making a personal care formulation comprising: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSiiR1) group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a C1-4 alkoxy group; and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate; and wherein the fatty acid ester comprises 50 to 100% biobased carbon content determined according to ASTM 6866-24, Method B.

[0014] The present invention provides a method of making a personal care formulation comprising: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSiiR'p group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a C alkoxy group; and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate; wherein the fatty acid ester comprises 50 to 100% biobased carbon content determined according to ASTM 6866-24, Method B; and wherein the fatty acid ester is readily biodegradable according to OECD 30 IF protocol.

[0015] The present invention provides a method of making a personal care formulation comprising: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been convertedAttorney Docket No.86610-WO-PCTto an -OSiiR 'p group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a CM alkoxy group; and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate; and wherein 25 to 100 % of the hydroxyl groups of the fatty acid ester have been converted to -OSi R'h groups in the silylated compound.DETAILED DESCRIPTION

[0016] We have surprisingly found that silylating a fatty acid ester selected from castor oil, hydrogenated castor oil and mixtures thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSiiR1p group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a C1-4 alkoxy group significantly reduces the viscosity of the fatty acid ester rendering it much more easily processed into personal care formulations as a silicone replacement ingredient and significantly improving the aesthetic characteristics of the formulation relative to an identical formulation comprising the fatty acid ester.

[0017] Unless otherwise indicated, ratios, percentages, parts, and the like are by weight.

[0018] As used herein, unless otherwise indicated, the phrase "molecular weight" or Mw refers to the weight average molecular weight as measured in a conventional manner with gel permeation chromatography (GPC) and conventional standards, such as pullulan narrow molecular weight standards with molecular weight range of 180 to 708,000 Daltons. GPC techniques are discussed in detail in Modem Size-Exclusion Liquid Chromatography -Practice of Gel Permeation and Gel Filtration Chromatography, Second Edition, A.M.Striegel, W. W. Yau, J. J. Kirkland, D. D. Bly; John Wiley & Sons, Inc. 2009. Molecular weights are reported herein in units of Daltons, or equivalently, g / mol.

[0019] The term "dermatologically acceptable" as used herein and in the appended claims refers to ingredients that are typically used for topical application to the skin, and is intended to underscore that materials that are toxic when present in the amounts typically found in skin care compositions are not contemplated as part of the present invention.

[0020] The term "aesthetic characteristics" as used herein and in the appended claims in reference to a personal care formulation refers to visual and tactile sensory properties (e.g., smoothness, tack, lubricity, texture, color, clarity, turbidity, uniformity).

[0021] The term "isocyanates" as used herein and in the appended claims refers to any material comprising an isocyanate group (-N=C=O). Isocyanates include, for example,Attorney Docket No.86610-WO-PCTtolylene diisocyanate, diphenylmethane diisocyanate, diphenylpropane diisocyanate, xylylene diisocyanate, diphenylsulfone diisocyanate, hexamethylene diisocyanate, 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate, 3, 3 '-diisocyanate dipropyl ether, diphenyl ether-4,4'-diisocyanate, isophorone diisocyanate.

[0022] The term "log P" as used herein and in the appended claims is equivalent to the predicted atom-based log P (A log P98). The log P is the logarithm of P, wherein P is the partition coefficient and is defined as a particular ratio of concentrations of a solute between 2-octanol and water. The log P value is a measure of lipophilicity or hydrophobicity. A log P98 is the log P value of a solute as predicted using QSAR methods, Hansch, C., Leo, A. D. Hoekman. Exploring QSAR-Hydrophobic, Electronic, and Steric Constants. Washing, D.C.: American Chemical Society, 1995, p.7.

[0023] The term "biobased" as used herein and in the appended claims refers to fatty acid esters containing organic carbon of renewable origin like agricultural, plant, animal, fungi, microorganisms, marine (e.g., algal) or forestry materials living in a natural environment in equilibrium with the atmosphere.

[0024] The term "biobased carbon content" as used herein and in the appended claims refers to the amount of biobased carbon in the fatty acid ester as a percent of the total organic carbon (TOC) in the fatty acid ester.

[0025] The term "natural oil" as used herein and in the appended claims refers to compounds comprising triglycerides and may contain varying levels of fatty acids, monoglycerides, diglycerides and triglycerides derived from plant, animal, fungi, protist and monera sources. Natural oils include fatty acid glyceryl esters, which are synthesized by reacting glycerol with 1, 2 or 3 molar equivalents of a fatty acid or a mixture of fatty acids. The compounds can be mono, di or triglycerides of a single fatty acid or a mixture of fatty acids.

[0026] The term "maleated natural oil" as used herein and in the appended claims refers to natural oil containing at least one maleated functionality.

[0027] The terms "maleated", "maleation" and the like as used herein and in the appended claim refers to the modification of natural oil molecules which introduce additional carboxylic moieties (or the related anhydride structure) onto the natural oil molecule by reaction of the natural oil with one or more of an a,0-unsaturated carboxylic acid or anhydride, for example, maleic anhydride. The a,0-unsaturated carboxylic acid or anhydride can be biogenically derived a,|3-unsaturated carboxylic acid or anhydride. Nonlimiting examples of biogenically derived a,0-unsaturated carboxylic acids or anhydrides include itaconic acid, itaconic anhydride, aconitic acid, aconitic anhydride, acrylic acid, methacrylicAttorney Docket No.86610-WO-PCTacid, citraconic acid, citraconic anhydride, mesaconic acid, muconic acid, glutaconic acid, methylglutaconic acid, traumatic acid and fumaric acid. The acids and anhydrides include any isomers (e.g., enantiomers, diastereomers and cis / trans isomers) and salts. The a, -unsaturated carboxylic acid and anhydride can maleic anhydride, maleic acid, fumaric acid, acrylic acid, methacrylic acid and their mixtures.

[0028] Preferably, the personal care formulation made by the method of the present invention is selected from the group consisting of a suncare formulation, a face care formulation, a make up formulation, a hair conditioner, a hair styling formulation, a conditioning shampoo formulation, a body care formulation, an antiperspirant / deodorant formulation, a body wash formulation, an exfoliating body wash formulation, a facial wash formulation, an exfoliating facial wash fonuulation, a liquid hand soap formulation, a sulfate-free cleansing formulation and a mild cleansing formulation. More preferably, the personal care formulation made by the method of the present invention is selected from the group consisting of a suncare fonuulation, a face care formulation, a make up formulation, a body care formulation, a hair conditioner, a conditioning shampoo and an antiperspirant / deodorant formulation. Most preferably, the personal care formulation made by the method of the present invention is a face care formulation, a body care formulation, a make up formulation, a suncare formulation and a hair conditioner (preferably, a leave on hair conditioner).

[0029] Preferably, the method of making a personal care formulation, of the present invention, comprises: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof (preferably, castor oil or a mixture of castor oil and hydrogenated castor oil with an average of at least 1 vinyl group per molecule; more preferably, castor oil or a mixture of castor oil and hydrogenated castor oil with an average of at least 2 vinyl groups per molecule; most preferably, castor oil); wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSilR1^ group; wherein each R1is independently selected from a hydrogen, a CM alkyl group, a phenyl group and a Ci-4 alkoxy group (preferably, a hydrogen and a Ci-4 alkyl group; more preferably, a C1-2 alkyl group; most preferably, a methyl group); and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle (preferably, wherein the dermatologically acceptable vehicle is selected from the group consisting of water; Cus monohydric alcohols (e.g., ethanol, propanol, isopropanol, hexanol); aromatic alcohols (e.g., benzyl alcohol, cyclohexanol); natural and synthetic oils (e.g., vegetable oils, plant oils, animal oils, essential oils, mineral oils); waxes (e.g., C7-40Attorney Docket No.86610-WO-PCTisoparaffins (such as, isododecane, isohexadecane, isoeicosane, C9-11 isoparaffin, C9-12 isoparaffin, C9-13 isoparaffin, C13-14 isoparaffin)); alkyl carboxylic esters (e.g., ethyl acetate, amyl acetate, ethyl lactate) and mixtures thereof; more preferably, wherein the dermatologically acceptable vehicle is selected from the group consisting of water, C1-4 monohydric alcohols, waxes, alkyd carboxylic esters and mixtures thereof; most preferably, wherein the dermatologically acceptable vehicle comprises water); wherein the personal care formulation comprises 0 to < 0.01 wt% (preferably, 0 to < 0.001 wt%; more preferably, 0 to < 0.0001 ; most preferably, 0 to < 0.00001 wt%), based on weight of the personal care formulation, of an isocyanate (preferably, wherein the personal care formulation comprises 0.5 to 70 wt% (preferably, 0.75 to 25 wt%; more preferably, 1 to 20 wt%; most preferably, 2 to 10 wt%), based on weight of the personal care formulation, of the silylated compound; and 25 to 99.5 wt% (preferably, 30 to 99 wt%; more preferably, 60 to 98 wt%; most preferably, 65 to 97 wt%), based on weight of the personal care formulation, of the dermatologically acceptable vehicle). More preferably, the method of making a personal care formulation, of the present invention, comprises: silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof (preferably, castor oil or a mixture of castor oil and hydrogenated castor oil with an average of at least 1 vinyl group per molecule; more preferably, castor oil or a mixture of castor oil and hydrogenated castor oil with an average of at least 2 vinyl groups per molecule; most preferably, castor oil); wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSi(R1) group; wherein each R1is independently selected from a hydrogen, a CM alkyl group, a phenyl group and a C1-4 alkoxy group (preferably, a hydrogen and a CM alkyl group; more preferably, a C1-2 alkyl group; most preferably, a methyl group); and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; and mixing the silylated compound with a dermatologically acceptable vehicle (preferably, wherein the dermatologically acceptable vehicle is selected from the group consisting of water; Ci-s monohydric alcohols (e.g., ethanol, propanol, isopropanol, hexanol); aromatic alcohols (e.g., benzy l alcohol, cyclohexanol); natural and synthetic oils (e.g.. vegetable oils, plant oils, animal oils, essential oils, mineral oils); waxes (e.g., C7-40 isoparaffins (such as, isododecane, isohexadecane, isoeicosane, C9-11 isoparaffin, C9-12 isoparaffin, C9-13 isoparaffin, C13-14 isoparaffin)); alkyl carboxylic esters (e.g., ethyl acetate, amyl acetate, ethyl lactate) and mixtures thereof; more preferably, wherein the dermatologically acceptable vehicle is selected from the group consisting of water, CM monohydric alcohols, waxes, alkyl carboxylic esters and mixturesAttorney Docket No.86610-WO-PCTthereof; most preferably, wherein the dermatologically acceptable vehicle comprises water); wherein the personal care formulation comprises 0 to < 0.01 wt% (preferably, 0 to < 0.001 wt%; more preferably, 0 to < 0.0001; most preferably, 0 to < 0.00001 wt%), based on weight of the personal care formulation, of an isocyanate (preferably, wherein the personal care formulation comprises 0.5 to 70 wt% (preferably, 0.75 to 25 wt%; more preferably, 1 to 20 wt%; most preferably, 2 to 10 wt%), based on weight of the personal care formulation, of the silylated compound; and 25 to 99.5 wt% (preferably, 30 to 99 wt%; more preferably. 60 to 98 wt%; most preferably, 65 to 97 wt%), based on weight of the personal care formulation, of the dermatologically acceptable vehicle); and with any one or more of the following additional provisos (i)-(xii) (all provisos taken individually, all possible combinations of two or more provisos and all of the provisos together are contemplated):(i) with the proviso that the silylated compound has a log P of > 10 (preferably, 11 to 50; more preferably, 12 to 40; still preferably, 15 to 35; yet more preferably, 20 to 30; most preferably, 25 to 27.5);(ii) with the proviso that the personal care formulation comprises < 0.1 (preferably, < 0.05; more preferably, < 0.01; still more preferably, < 0.001; most preferably, < 0.0001) equivalent isocyanate groups with respect to the total number of hydroxyl groups in the silylated compound;(iii) with the proviso that the personal care formulation further comprises a humectant and / or emulsifier selected from the group consisting of glycerin, sorbitol, monoglycerides, lecithins, glycolipids, fatty acids, fatty acid salts (e.g., glyceryl stearate), polysaccharides, sorbitan esters, polysorbates (e.g., Polysorbate 20, Polysorbate 40, Polysorbate 60, and Polysorbate 80), natural oils (e.g., Jojoba oil) and mixtures thereof; (preferably, wherein the humectant and / or emulsifier includes at least one of glycerin, Jojoba oil and a fatty acid salt; more preferably, wherein the humectant and or emulsifier includes a mixture of glycerin and a fatty acid salt; most preferably, wherein the humectant and / or emulsifier includes a mixture of glycerin and glyceryl stearate);(iv) with the proviso that the personal care formulation comprises < 0.005 wt% (preferably, 0 to < 0.001 wt%; more preferably, 0 to < 0.0001 wt%; still more preferably. 0 to < 0.00001 wt%; yet more preferably, 0 to < 0.000001 wt%; most preferably, less than detectable limit), based on weight of the personal care formulation, of a maleated natural oil;(v) with the proviso that the silylated compound comprises 0 maleated functionalities per molecule of the silylated compound;Attorney Docket No.86610-WO-PCT(vi) with the proviso that the personal care formulation comprises < 0.005 wt% (preferably, 0 to < 0.001 wt%; more preferably, 0 to < 0.0001 wt%; still more preferably. 0 to < 0.00001 wt%; yet more preferably, 0 to < 0.000001 wt%; most preferably, less than detectable limit) , based on weight of the personal care formulation, of silylated compound having > 4 carbonyl groups (C=O) per molecule;(vii) with the proviso that the fatty acid ester comprises 50 to 100% (preferably, 75 to 100%; more preferably, 90 to 100%; most preferably, 99 to 100%) biobased carbon content determined according to ASTM 6866-24, Method B;(viii) with the proviso that the fatty acid ester is readily biodegradable according to OECD 301F protocol;(ix) with the proviso that 25 to 100% (preferably, 50 to 100%) of the hydroxyl groups of the fatty acid ester have been converted to -OSi(R1)r groups in the silylated compound;(x) with the proviso that each R1is independently selected a C1-2 alkyd group;(xi) with the proviso that each R1is a methy l group; and(xii) with the proviso that the personal care formulation further comprises a personal care additive (preferably. 0 to 74.5 wt%; more preferably, 0.25 to 69.25 wt%; still more preferably, 1 to 38 wt%: most preferably, 1 to 32.5 wt%), based on weight of the personal care formulation, of the personal care additive); wherein the personal care additive is selected from the group consisting of selected from the group consisting of an absorbent; an aesthetic enhancer (e.g., starch); an alpha hydroxy acid: an antiaging agent; an antidandruff agent; an antifungal; an antimicrobial agent; an antioxidant (e.g., butylated hydroxy toluene); an antiseptic; an antistatic agent; a bioactive agent; a bleaching agent; a chelating agent; a cleaning surfactant; a colorant; a conditioning agent (e.g., silicone, polyquatemium, cationic guar); a dye; an emollient; a film former (e.g., water proofing agent); a fixative polymer; a foaming agent; a fragrance; a hard particle; a humectant and / or emulsifier (e.g., glycerin, sorbitol, monoglycerides, lecithins, glycolipids, fatty alcohols, fatty acids, polysaccharides, sorbitan esters, polysorbates (e.g., Polysorbate 20, Polysorbate 40, Polysorbate 60, and Polysorbate 80), glycols (e.g., propylene glycol)); a lubricating agent; a nonionic surfactant other than an acyclic branched alcohol ethoxy glucoside surfactant: an opacifier; a pearlizing agent; a penetrant; a pH adjusting agent; a pigment; a plant extract; a preservative (e.g., benzoic acid, sorbic acid, phenoxyethanol); a protein / amino acid; a rheology modifier; a salt (e.g., NaCl); a sensory modifier; a slip agent; a soap; a soft particle; a sunscreen additive; a suspending agent; a UV light inhibitor; a vitamin and mixtures thereof.Attorney Docket No.86610-WO-PCT

[0030] Preferably, the personal care formulation made by the method of the present invention, comprises: 25 to 99.5 wt% (preferably, 30 to 99 wt%; more preferably, 60 to 98 wt%; most preferably, 65 to 97 wt%), based on weight of the personal care formulation, of a dermatologically acceptable vehicle. More preferably, the personal care formulation made by the method of the present invention, comprises: 25 to 99.5 wt% (preferably, 30 to 99 wt%; more preferably, 60 to 98 wt%; most preferably, 65 to 97 wt%), based on weight of the personal care formulation, of a dermatologically acceptable vehicle; wherein the dermatologically acceptable vehicle is selected from the group consisting of water; Cus monohydric alcohols (e.g., ethanol, propanol, isopropanol, hexanol); aromatic alcohols (e.g., benzy l alcohol, cyclohexanol); natural and synthetic oils (e.g., vegetable oils, plant oils, animal oils, essential oils, mineral oils); waxes (e.g., C7-40 isoparaffins (such as, isododecane, isohexadecane, isoeicosane, C9-11 isoparaffin, C9-12 isoparaffin, C9-13 isoparaffin, C13-14 isoparaffin)); alkyl carboxylic esters (e.g., ethyl acetate, amyl acetate, ethyl lactate) and mixtures thereof. Still more preferably, the personal care formulation made by the method of the present invention, comprises: 25 to 99.5 wt% (preferably. 30 to 99 wt%; more preferably, 60 to 98 wt%; most preferably, 65 to 97 wt%), based on weight of the personal care formulation, of a dermatologically acceptable vehicle; wherein the dermatologically acceptable vehicle is selected from the group consisting of water, C1-4 monohydric alcohols, waxes, alkyl carboxylic esters and mixtures thereof. Most preferably, the personal care formulation made by the method of the present invention, comprises: 25 to 99.5 wt% (preferably, 30 to 99 wt%; more preferably, 60 to 98 wt%; most preferably, 65 to 97 wt%), based on weight of the personal care formulation, of a dermatologically acceptable vehicle; wherein the dermatologically acceptable vehicle comprises water.

[0031] Preferably, the water used in the personal care formulation made by the method of the present invention is at least one of distilled water and deionized water. More preferably, the water used in the personal care formulation made by the method of the present invention is distilled and deionized.

[0032] Preferably, the personal care formulation made by the method of the present invention, comprises: 0.5 to 70 wt% (preferably, 0.75 to 25 wt%; more preferably. 1 to 20 wt %; most preferably, 2 to 10 wt%), based on weight of the personal care formulation, of a silylated compound formed by silylating a fatty acid ester selected from the group consisting of castor oil, hydrogenated castor oil and mixtures thereof (preferably, castor oil or a mixture of castor oil and hydrogenated castor oil with an average of at least 1 vinyl group per molecule; more preferably, castor oil or a mixture of castor oil and hydrogenated castor oilAttorney Docket No.86610-WO-PCTwith an average of at least 2 vinyl groups per molecule; most preferably, castor oil); wherein at least one hydroxyl (-OH) group of the fatty acid ester has been converted to an -OSi(R1) group; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a C1-4 alkoxy group (preferably, a hydrogen and a C1-4 alkyl group; more preferably, a C1-2 alkyl group; most preferably, a methyl group).

[0033] Preferably, the fatty acid ester comprises 50 to 100% (preferably, 75 to 100%; more preferably, 90% to 100%; most preferably, 99 to 100%) biobased carbon content determined according to ASTM 6866-24, Method B.

[0034] Preferably, the fatty acid ester is readily biodegradable according to OECD 30 IF protocol.

[0035] Preferably, 25 to 100% (preferably, 50 to 100%) of the hydroxyl groups of the fatty acid ester have been converted to -OSi(R1)s groups in the silylated compound.

[0036] Preferably, the silylated compound has a log P of > 20 (preferably, 20 to 50; more preferably, 20 to 40; still preferably, 20 to 35; yet more preferably, 20 to 30; most preferably, 25 to 27.5).

[0037] Preferably, the silylated compound comprises 0 maleated functionalities per molecule.

[0038] Preferably, wherein the personal care formulation made by the method of the present invention comprises < 0.005 wt% (preferably, 0 to < 0.001 wt%; more preferably, 0 to < 0.0001 wt%; still more preferably, 0 to < 0.00001 wt%; yet more preferably, 0 to < 0.000001 wt%; most preferably, less than detectable limit), based on weight of the personal care formulation, of silylated compound having > 4 carbonyl groups (C=O) per molecule.

[0039] Preferably, the personal care formulation made by the method of the present invention, optionally, further comprises 0 to 74.5 wt% (preferably, 0.25 to 69.25 wt%; more preferably, 1 to 38 wt%; most preferably, 1 to 32.5 wt%), based on weight of the personal care formulation, of a personal care additive; wherein the personal care additive is selected from the group consisting of selected from the group consisting of an absorbent; an aesthetic enhancer (e.g., starch); an alpha hydroxy acid; an antiaging agent; an antidandruff agent; an antifungal; an antimicrobial agent; an antioxidant (e.g., butylated hydroxy toluene); an antiseptic; an antistatic agent; a bioactive agent; a bleaching agent; a chelating agent; a cleaning surfactant; a colorant; a conditioning agent (e.g., silicone, polyquaternium, cationic guar); a dye; an emollient; a film former (e.g., water proofing agent); a fixative polymer; a foaming agent; a fragrance; a hard particle; a humectant and / or emulsifier (e.g., glycerin, sorbitol, monoglycerides, lecithins, glycolipids, fatty alcohols, fatty acids, polysaccharides, sorbitan esters, polysorbates (e.g.. Polysorbate 20, Polysorbate 40, Polysorbate 60, andAttorney Docket No.86610-WO-PCTPolysorbate 80), glycols (e.g., propylene glycol)); a lubricating agent; a nonionic surfactant other than an acyclic branched alcohol ethoxy glucoside surfactant; an opacifier; a pearlizing agent; a penetrant; a pH adjusting agent; a pigment; a plant extract; a preservative (e.g., benzoic acid, sorbic acid, phenoxyethanol); a protein / amino acid; a rheology modifier; a salt (e.g., NaCl); a sensory modifier; a slip agent; a soap; a soft particle; a sunscreen additive; a suspending agent; a UV light inhibitor; a vitamin and mixtures thereof. More preferably, the personal care formulation made by the method of the present invention, optionally, further comprises 0 to 74.5 wt% (preferably, 0.25 to 69.25 wt%; more preferably, 1 to 38 wt%; most preferably, 1 to 32.5 wt%), based on weight of the personal care formulation, of a personal care additive; wherein the personal care additive includes a humectant and / or emulsifier selected from the group consisting of glycerin, sorbitol, monoglycerides, lecithins, glycolipids, fatty acids, fatty acid salts (e.g., glyceryl stearate), polysaccharides, sorbitan esters, polysorbates (e.g., Polysorbate 20, Polysorbate 40, Polysorbate 60, and Polysorbate 80), natural oils (e.g., Jojoba oil) and mixtures thereof (preferably, wherein the humectant and / or emulsifier includes at least one of glycerin. Jojoba oil and a fatty acid salt; more preferably, wherein the humectant and / or emulsifier includes a mixture of glycerin and a fatty acid salt; most preferably, wherein the humectant and / or emulsifier includes a mixture of glycerin and glyceryl stearate).

[0040] Preferably, the personal care formulation made by the method of the present invention comprises < 0.1 (preferably, < 0.05; more preferably, < 0.01; still more preferably, < 0.001; most preferably, < 0.0001) equivalent isocyanate groups with respect to the total number of hydroxyl groups in the silylated compound.

[0041] Preferably, the personal care formulation made by the method of the present invention comprises < 0.005 wt% (preferably, 0 to < 0.001 wt%; more preferably, 0 to < 0.0001 wt%; still more preferably, 0 to < 0.00001 wt%; yet more preferably, 0 to < 0.000001 wt%; most preferably, less than detectable limit), based on weight of the personal care formulation, of a maleated natural oil.

[0042] Some embodiments of the present invention will now be described in detail in the following Examples.Syntheses S1-S2: Silylation of polyols

[0043] Into a round bottom flask was added saccharin as a catalyst followed by introduction of the polyol noted in TABLE 1. The flask was then connected to vacuum to ensure sufficient drying at 80 to 100 °C until no bubbles were observed in the flask contents. A trap containing a diluted HC1 solution (0.1 N) was connected to the system to catch the volatiles producedAttorney Docket No.86610-WO-PCTduring the reaction. Then a molar excess of hexamethyldisilazane (HMDZ) relative to the -OH groups present in the polyol was added to the flask via a funnel. The temperature and vacuum were turned up during the reaction to optimize capping efficiency. Aliqouts were withdrawn from time to time and analyzed by1H NMR to check the capping efficiency by the shift of -CH2OH signal at 3.65 ppm to lower chemical shift due to the formation of -CH2-OSi(CH3)s end groups. Additional charges of HMDZ were added to the flask contents as necessary until the -CH2OH signal at 3.65 disappeared. The flask was then heated up to 150 °C under high vacuum to remove the HMDZ excess from the flask contents. The product in the flask was then dried under vacuum at 70 °C for 72 hours and the product was confirmed to be without any trace of residual HMDZ as attested by1f I NMR. The weight average molecular weight, Mw, in Daltons of the product was then measured by GPC with the results provided in TABLE 2.Viscosity

[0044] The viscosity of each of the silylated materials prepared according to Synthesis S1-S2 were measured using a Modular Compact Rheometer (MCR300 Serial No. 701266) using the CP 50-1 cone and plate geometry and a shear rate of 100 sec1. The application used was US200 / 31 V2.43 21001579-33024 with the following parameters:The viscosities at 20 °C is reported in TABLE 2.Log Kow (Log P)

[0045] The Log Kow of each of the silylated materials prepared according to Synthesis Sl-S2 were calculated using QSAR method (EPI (Estimation Programs Interface) Suite KOWWIN v 1.69. The results are reported in TABLE 2.Attorney Docket No.86610-WO-PCTRefractive Index (at 25 °C)

[0046] The refractive idex of each of the silylated materials prepared according to Synthesis S1-S2 was measured using Mettler-Toledo's portable refractometer. The results are reported in TABLE 2.T BLE 2Water Contact Angle On Film

[0047] Films were prepared from the ingredient noted in TABLE 3. Specifically, the films were prepared by drawdown of a wet film (25 pm) with a two-sided cube applicator onto glass slide . The drawn films were allowed to air dry in an environmental! controlled rom (72 °F and 50% RH) for at least 72 hours before making measurements. The water contact angles were measured at 4 seconds and 120 seconds after water droplets were deposited on the substrate using a KSV CAM 200 Optical Contact Angle Meter. The results of the water contact angle measurements are provided in TABLE 3. Due to its high melting point temperature, hydrogenated castor oil was heated for casting the film, which solidifies instantaneously. The associated hydrogenated castor oil data reported in Table 3 are misleading as they are not representative of molecules in a liquid state that can reorient themselves when exposed to the water droplet during the contact angle measurement.TABLE 3Comparative Examples CF1-CF2 and Example Fl: Skin Care Formulations

[0048] Oil in water skin care formulations were prepared in each of Comparative Examples CF1-CF2 and Example Fl having the ingredients noted in TABLE 4.Antisoaping Benefit

[0049] The oil in water skin care formulations of Comparative Examples CF1-CF2 and Example Fl were evaluated for antisoaping benefit. A controlled amount of the oil in water skin care formulation was applied on the forearm of panelists. The lasting properties of the undesirable soaping (foaming / whitening) effect, which appears when rubbing a silicone-free, oil-rich, oil in water emulsion on the skin surface, was observed and compared toAttorney Docket No.86610-WO-PCTformulations containing either the non-silylated polyol material (CF1: control formulation expected to produce high level of soaping) or dimethicone 350 cSt fluid (CF2: control formulation expected to produce low level of soaping). The skin care formulation of Comparative Example CF1 containing castor oil had significantly more soaping than the skin care formulation of Example Fl containing silylated castor oil. The skin care formulation of Example Fl was slightly less performing that Comparative Example CF2 containing the dimethicone 350 cSt fluid.TABLE 4Skin Care Performance

[0050] Studies to evaluate the slipperiness of skin treated with a skin care ingredient of Comparative Example CF3 and Examples F2-F3 were performed as follows. The skin care ingredients of Comparative Example CF3 and Examples F2-F3 were applied to a skin mimicking Vitro-Skin substrate (from IMS Inc.) at 25 pm (wet thickness) using an automatic coater and a four-sided coating applicator. The deposited films were air dried in an environmentally controlled room (~22 °C and 50% RH) overnight.

[0051] A Dia-Stron Friction testor (model number MTT175 Miniature Tensile Tester in conjunction with a Universal Control Unit, model UV1000 and UvWin Softare) was thenAttorney Docket No.86610-WO-PCTused to measure the friction between the treated Vitro-Skin substrate and a rubber probe mounted on a balanced arm assembly (force needed to move the rubber probe down the treated Vitro-Skin substrate). An average friction force from two treated substrates was measured for each skin care ingredient. After measurement an analysis tool was used to calculate the average coefficient of friction for each ingredient which is provided in TABLE 5.TABLE 5Comparative Example CHI and Examples H1-H2: Leave on Hair Formulations

[0052] Leave on hair conditioner formulations were prepared in each of Comparative Example CHI and Examples H1-H2 having the ingredients noted in TABLE 6.Hair Care Performance

[0053] Studies to evaluate the slipperiness of hair treated with a leave on conditioner formulation of Comparative Example CHI and Examples H1-H2 were performed as follows. Slightly bleached Caucasian hair from International Hair Importers was used for the testing. Each tress weighted 2 grams. Each tress was rinsed for 30 seconds under a stream of 40 °C tap water with a flow rate of about 5.5 L / min. Using a pipette, 0.4 grams of a solution containing nine percent of sodium lauryl sulfate was applied and lathered through each tress for 30 seconds. The tresses were then rinsed for 1 minute under running 40 °C tap water with a flow rate of about 5.5 L / min. Excess water was removed from the tresses by passing each tress between the index and middle fingers of the hand twice. The tresses were then allowed to dry on a paper towel overnight at room temperature. The tresses were then wetted for 15 seconds under 40 °C tap water with a flow rate of about 5.5 L / min. Excess water was removed from the tresses by passing each tress between the index and middle fingers of the hand. The tresses were then laid on a clean support and 100 microliters of leave on conditioner formulation was applied to the tresses using a calibrated micropipette. The leave on conditioner formulation was allowed to dry on the tresses overnight. Each tress was then combed through three times with the cuticle before performing the friction test.

[0054] A Dia-Stron Friction testor (model number MTT175 Miniature Tensile Tester in conjunction with a Universal Control Unit, model UV1000 and UvWin Softare) was then used to measure the friction between the hair tresses and a rubber probe mounted on a balanced arm assembly (force needed to more the rubber probe down a hair tress). The frictional forces were measured with the cuticle. An average dry friction force from threeAttorney Docket No.86610-WO-PCTtresses was measured for each leave on conditioner formulation. After measurement an analysis tool was used to calculate the average coefficient of friction for each leave in conditioner formulation which is provided in TABLE 6.TABLE 6Comparative Example CH2 and Example H3; Leave on Hair Formulations

[0055] Leave on hair conditioner formulations were prepared in each of Comparative Example CH2 and Example H3 having the ingredients noted in TABLE 7.TABLE 71NXT SOLV 300 ethyl pg-acetal levulinate from NXTLEVVELHair Care Sensory

[0056] Studies to evaluate the sensory performance of a leave on conditioner formulation on hair of Comparative Example CH2 and Example H3 were performed as follows. Slightly bleached Caucasian hair from International Hair Importers was used for the testing. Each tress weighted 2 grams. Each tress was rinsed for 30 seconds under a stream of 40 °C tap water with a flow rate of about 5.5 L / min. Using a pipette, 0.4 grams of a solution containing nine percent of sodium lauryl sulfate was applied and lathered through each tress for 30 seconds. The tresses were then rinsed for 1 minute under running 40 °C tap water with a flow rate of about 5.5 L / min. Excess water was removed from the tresses by passing each tress between the index and middle fingers of the hand twice. The tresses were then allowed to dry on a paper towel overnight at room temperature. The tresses were then wetted for 15 seconds under 40 °C tap water with a flow rate of about 5.5 L / min. Excess water was removed from the tresses by passing each tress between the index and middle fingers of the hand. The tresses were then laid on a clean support and 100 microliters of leave in conditioner formulation was applied to the tresses using a calibrated micropipette. The leave on conditioner formulation was allowed to dry on the tresses for 60 minutes. Each tress wasAttorney Docket No.86610-WO-PCTthen evaluated by a group of five panelists to assess the sensory profile of the treated hair. The results of the evaluation are provided in TABLE 7.TABLE 7

Claims

1. Attorney Docket No.86610-WO-PCTWe claim:

1. A method of making a personal care formulation comprising:silylating a fatty acid ester to form a silylated compound; wherein the fatty acid ester is selected from the group consisting of castor oil, hydrogenated castor oil and a mixture thereof; wherein at least one hydroxyl (-OH) group of the fatty acid ester has been convertedgroup; wherein each R1is independently selected from a hydrogen, a C1-4 alkyl group, a phenyl group and a CM alkoxy group; and wherein the silylated compound has a viscosity of < 300 cP measured at 20 °C; andmixing the silylated compound with a dermatologically acceptable vehicle; wherein the personal care formulation comprises 0 to < 0.01 wt%, based on weight of the personal care formulation, of an isocyanate.

2. The method of claim 1, with any one or more of the following provisos (i)- (xii):(i) with the proviso that the silylated compound has a log P of > 10;(ii) with the proviso that the personal care formulation comprises < 0.1 equivalent isocyanate groups with respect to the total number of hydroxyl groups in the silylated compound;(iii) with the proviso that the personal care formulation further comprises a humectant and / or emulsifier selected from the group consisting of glycerin, sorbitol, monoglycerides, lecithins, glycolipids, fatty acids, fatty acid salts, polysaccharides, sorbitan esters, polysorbates, natural oils and mixtures thereof;(iv) with the proviso that the personal care formulation comprises < 0.005 wt%, based on weight of the personal care formulation, of a maleated natural oil;(v) with the proviso that the silylated compound comprises 0 maleated functionalities per molecule of the silylated compound;(vi) with the proviso that the personal care formulation comprises < 0.005 wt%, based on weight of the personal care formulation, of silylated compound having > 4 carbonyl groups (C=O) per molecule;(vii) with the proviso that the fatty acid ester comprises 50 to 100% biobased carbon content determined according to ASTM 6866-24, Method B;(viii) with the proviso that the fatty acid ester is readily biodegradable according to OECD 301F protocol;(ix) with the proviso that 25 to 100% of the hydroxyl groups of the fatty acid ester have been converted to -OSi / R^a groups in the silylated compound;Attorney Docket No.86610-WO-PCT(x) with the proviso that each R1is independently selected a C1-2 alkyl group;(xi) with the proviso that each R1is a methyl group; and(xii) with the proviso that the personal care formulation further comprises a personal care additive; wherein the personal care additive is selected from the group consisting of selected from the group consisting of an absorbent; an aesthetic enhancer; an alpha hydroxy acid; an antiaging agent; an anti dandruff agent; an antifungal; an antimicrobial agent; an antioxidant; an antiseptic; an antistatic agent; a bioactive agent; a bleaching agent; a chelating agent; a cleaning surfactant; a colorant; a conditioning agent; a dye; an emollient; a film former; a fixative polymer; a foaming agent; a fragrance; a hard particle; a humectant and / or emulsifier; a lubricating agent; a nonionic surfactant other than an acyclic branched alcohol ethoxy glucoside surfactant; an opacifier; a pearlizing agent; a penetrant; a pH adjusting agent; a pigment; a plant extract; a preservative; aprotein / amino acid; a rheology modifier; a salt; a sensory modifier; a slip agent; a soap; a soft particle; a sunscreen additive; a suspending agent; a UV light inhibitor; a vitamin and mixtures thereof.

3. The method of claim 1 , wherein the silylated compound has a log P of > 20.

4. The method of claim 1, wherein the personal care formulation comprises < 0.1 equivalent isocyanate groups with respect to the total number of hydroxyl groups in the silylated compound.

5. The method of claim 1, wherein the personal care formulation comprises < 0.005 wt%, based on weight of the personal care formulation, of a maleated natural oil.

6. The method of claim 1, wherein the silylated compound comprises 0 maleated functionalities per molecule of the silylated compound.

7. The method of claim 1, wherein the personal care formulation comprises < 0.005 wt%, based on weight of the personal care formulation, of silylated compound having > 4 carbonyl groups (C=O) per molecule.

8. The method of claim 1, wherein 25 to 100 % of the hydroxyl groups of the fatty acid ester have been converted to -OSiiR1)3 groups in the silylated compound.

9. The method of claim 8, wherein each R1is independently selected a C1-2 alkyl group.

10. The method of claim 9, wherein each R1is a methyl group.

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