Title - HAIR CARE COMPOSITION

Abstract

A hair care composition is described comprising a polyhydroxylated fatty acid amide surfactant of the general formula (1) wherein R 1 is an alkyl group C 1-4 or alkyl groups C 1- 4 substituted with hydroxyl; R 2 CO is an acyl group C 12-18 saturated or unsaturated, linear or branched, a silicone compound and 0.01 to 10% by weight of an anti-dandruff agent selected from piroctone olamine, azole-based antifungal agents and mixtures thereof.

Description

DESCRIPTIVE MEMORANDUM Technical field of the invention The present invention relates to hair care compositions comprising a specific nonionic surfactant, a silicone compound, and anti-dandruff agents. This invention also relates to the use of such compositions to deposit anti-dandruff agents onto the hair and / or scalp of an individual. Background of the invention Hair care products typically provide cleansing or conditioning benefits, or a combination of both. These products usually contain one or more cleansing surfactants that help cleanse the hair and scalp, removing dirt, particles, and unwanted oils. However, the ideal hair care product offers more than just cleansing and conditioning. For example, it's desirable to incorporate mild surfactants into hair care products so they are non-irritating and gentle on the scalp. It is also desirable to incorporate several beneficial agents into the hair care formula to provide benefits beyond cleansing and conditioning. For example, anti-dandruff benefits have been provided through hair care formulations. Dandruff is a problem Dandruff, a condition affecting many people worldwide, is characterized by the shedding of clumps of dead skin cells from the scalp. These flakes are white and have an unsightly appearance. Certain Malassezia yeasts contribute to dandruff. To combat them, anti-dandruff products often contain antifungal agents such as piroctone olamine (Octopirox®), azole antifungals (e.g., climbazole, ketoconazole), selenium sulfide, or combinations thereof. However, many anti-dandruff formulations fail to provide sufficient deposition of the anti-dandruff agent during the rinsing process. The anti-dandruff agents are simply rinsed away, thus providing little to no effective anti-dandruff benefit.Therefore, it is always desirable to effectively deposit anti-dandruff agents on the hair and / or scalp to provide good anti-dandruff performance. WO 2015 / 078587 A1 discloses compositions containing at least one N-alkyl-N-acylglucamine as component A, dimethiconol as component B, at least one anionic surfactant as component C, optionally at least one betaine surfactant as component D, optionally at least one other surfactant as component E, water as component F, and optionally at least one other additive as component G, the compositions of which can be used as hair washing agents. Document WO 2013 / 178697 A2 describes that N-methyl-N-acylglucamines are suitable as thickening agents in aqueous surfactant solutions that 1176086 of 26 contain one or more anionic surfactants from the group containing alkyl ether sulfates and alkyl sulfates, containing at least the N-methyl-N-acylglucamines 60% by weight of N-methyl-N-acylglucamines having a C12, C14 or C18 unsaturated acyl group and at the same time less than 5% by weight of N-methyl-N-acylglucamines containing an acyl group <Ci2. Document WO 9205764 Ai describes the mixed composition of conditioning / anti-dandruff shampoo containing 3.6% by weight of coconut N-methylglucose amide, 1.5% by weight of dimethicone and 1.5% by weight of selenium sulfide. Document US 2019365619 A1 describes a salicylic acid anti-dandruff cleansing composition and a surfactant system. The present inventors have now unexpectedly discovered that a composition comprising a polyhydroxylated fatty acid amide surfactant and a silicone compound can provide desirable smoothness and also improved deposition of anti-dandruff agents. Summary of the invention In one aspect, the present invention relates to a hair care composition comprising: (a) a polyhydroxylated fatty acid amide surfactant of general formula (I): 1176086 of 26 O r1OH R2 CN CH2 CH CH2OH - -14 (I) where R1 is a C1-C4 alkyl group or C1-C4 alkyl groups substituted with hydroxy; R2CO is a saturated or unsaturated, linear or branched C12-C18 acyl group: (b) a silicone compound; and (c) from 0.01 to 10% by weight of an anti-dandruff agent selected from piroctone olamine, azole-based antifungal agents and mixtures thereof. In a second aspect, the present invention relates to a packaged hair care product comprising the hair care composition of the first aspect of this invention. In a third aspect, the present invention relates to a method for depositing anti-dandruff agents on the scalp comprising the step of applying the hair care composition of any embodiment of the first aspect of this invention to the scalp surfaces of an individual, followed by rinsing the surfaces with water. All other aspects of the present invention will become more evident upon consideration of the detailed description and examples that follow. 1176086 of 26 Detailed description Except in the examples, or where explicitly stated otherwise, all numbers in this description that indicate quantities of material or reaction conditions, physical properties of materials and / or use may optionally be understood as modified by the word approximately. All quantities are by weight of the final hair care composition unless otherwise specified. It should be noted that when specifying any range of values, any particular upper value may be associated with any particular lower value. To avoid confusion, the word "comprises" means that it includes, but not necessarily that it consists of or is composed of. In other words, the stages or options listed do not need to be exhaustive. The disclosure of the invention, as it is found herein, should be considered to encompass all embodiments found in the claims as being multiplely dependent on each other, regardless of the fact that claims without multiple dependence or redundancy may be found. When a feature is disclosed with respect to a particular aspect of the invention (e.g., a composition of the invention), such disclosure should also be considered applicable to any other aspect of the invention (e.g., a method of the invention) mutatis mutandis. 1176086 of 26 Hair care composition, as used herein, means a composition for topical application to the hair and / or scalp of mammals, especially humans. Such a composition may be generally classified as a leave-in or rinse-out composition and includes any product applied to the human body to further enhance appearance, cleanliness, odor control, or overall aesthetics. The composition of the present invention may be in the form of a liquid, lotion, cream, foam, scrub, gel, or bar. Non-restrictive examples of such compositions include leave-in hair lotions, creams, rinse-out shampoos, conditioners, shower gels, or bar soap. The composition of the present invention is preferably a rinse-out composition, especially preferably a shampoo or conditioner, and most preferably a shampoo. The polyhydroxylated fatty acid amide surfactant suitable for use in the compositions of the present invention is a non-ionic surfactant represented by the general formula (I): O R1OH R2-CN-CH2—CH--CH2-OH - J 4 (I) wherein R1 is a C1-C4 alkyl group or C1-C4 alkyl groups substituted with hydroxy; R2CO is a saturated or unsaturated, linear or branched C12-C18 acyl group. Preferably, R1 is a methyl group, the acyl group R2CO is derived from acid 1176086 of 26 lauric, myristic acid, oleic acid, linoleic acid, palmitic acid or stearic acid. In another preferred embodiment, R1 is a methyl group, the acyl group R2CO is derived from coconut oil. Most preferably, the polyhydroxylated fatty acid amide of general formula (I) for use in the invention includes lauroyl methyl glucamide, cocoyl methyl glucamide, myristoyl methyl glucamide, or mixtures thereof, preferably lauroyl methyl glucamide, myristoyl methyl glucamide, or mixtures thereof, more preferably myristoyl methyl glucamide or a mixture thereof with lauroyl methyl glucamide. In a preferred embodiment, the polyhydroxylated fatty acid amide comprises at least 60% by weight of a mixture of lauroyl methyl glucamide and myristoyl methyl glucamide based on the total weight of the polyhydroxylated fatty acid amide, preferably from 65 to 99% by weight of a mixture of lauroyl methyl glucamide and myristoyl methyl glucamide, more preferably from 70 to 95%, based on the total weight of the polyhydroxylated fatty acid amide. In another preferred embodiment, the polyhydroxylated fatty acid amide is a mixture of lauroyl methyl glucamide and myristoyl methyl glucamide. The polyhydroxylated fatty acid amide preferably comprises lauroyl methyl glucamide and myristoyl methyl glucamide in a weight ratio ranging from 1:5 to 10:1, more preferably from 1:2 to 5:1. The composition of the present invention may additionally have small fractions of polyhydroxylated fatty acid amide derived from short-chain fatty acids, in particular those comprising C1-C4, C6, C8, C10 acyl groups. 1176086 of 26 Examples of commercially produced polyhydroxylated fatty acid amides having the general formula (I) and suitable for use in the present invention include lauroyl / myristoyl methylglucamide (GLUCOTAIN® FLEX, Clariant Company) Ltd.), cocoyl methyl glucoamide (GLUCOTAIN® CARE, Clariant Ltd. company) and mixtures thereof. The hair care composition typically comprises the polyhydroxylated fatty acid amide in an amount of 0.1 to 45%, more preferably 1 to 30% and more preferably 5 to 20%, based on the total weight of the hair care composition and including all intervals therein. The hair care composition of the present invention comprises a silicone compound. Preferably, the silicone compound is a non-volatile silicone. “Non-volatile,” as used herein, means that the silicone has a vapor pressure of less than 1000 Pa at 25°C and atmospheric pressure. Preferably, the silicone compound consists of emulsified droplets of silicone oil, which has a mean droplet diameter (D3,2) of less than 15 µm, preferably less than 10 µm, and more preferably less than 5 µm. Preferably, the mean droplet diameter (D3,2) of a silicone oil is greater than 0.05 µm, more preferably greater than 0.1 µm, and ideally from 0.1 µm to 5 µm. The mean droplet diameter (D3,2) of a silicone oil can be measured 1176086 of 26 by a laser light scattering technique, for example, using a Malvern Instruments 2600D particle meter. Suitable silicones include polydiorganosiloxanes, in particular polydimethylsiloxanes designated CTFA dimethicone. Also suitable for use in the compositions of this invention (especially shampoos and conditioners) are polydimethylsiloxanes having terminal hydroxyl groups, designated CTFA dimethiconol. Silicone rubbers having a slight degree of crosslinking, as described, for example, in WO 96 / 31188, are also suitable for use in the compositions of this invention. Preferably, the silicone oil comprises dimethicone, dimethiconol, or a mixture thereof. The viscosity of a preferred silicone compound used as an emulsified silicone oil in itself is typically at least 10,000 cSt (centistokes = mm2*S-1) at 25°C, preferably at least 60,000 cSt is the highest preference, but at least 500,000 cSt is preferred, and ideally at least 1,000,000 cSt. Preferably, the viscosity should not exceed 109 cSt to facilitate formulation. The viscosity of the silicone can be determined, for example, using the relevant international standard, such as ISO 3104. Emulsified silicones suitable for use in the hair care compositions of this invention are available as pre-formed silicone emulsions from silicone suppliers such as Dow Silicones Corporation and GE Silicones. The use of such a silicone emulsion is preferred. 1176086 of 26 preformed for easy processing and control of silicone particle size. Such preformed silicone emulsions shall further comprise a suitable emulsifier and may be prepared by a chemical emulsification process such as emulsion polymerization, or by mechanical emulsification using a high-shear mixer. Examples of suitable preformed silicone emulsions include MEM-7128, MEM-1788, and MEM-1785, all available from Dow Silicones. Corporation. These are dimethiconol / dimethicone emulsions. Another class of silicones that can be used are functionalized silicones, such as amino-functional silicones, meaning a silicone that contains at least one primary, secondary, or tertiary amine group, or a quaternary ammonium group. Examples of suitable amino-functional silicones include polysiloxanes with the CTFA designation amodimethicone. The silicone compound is generally present in the hair care composition of the present invention in an amount of 0.1 to 15%, more preferably 0.5 to 10%, and most preferably 1 to 5%, based on the total weight of the hair care composition and includes all intervals therein. The hair care composition comprises anti-dandruff agents, which are compounds active against dandruff and are generally antimicrobial and preferably antifungal agents. The anti-dandruff agents used in the present invention are selected from piroctone olamine (Octopirox®), azole-based antifungal agents, and mixtures thereof. 1176086 of 26 preferred azole-based antifungal is ketoconazole, climbazole or mixtures of them. Preferably, the anti-dandruff agent is selected from piroctone olamine, climbazole, and mixtures thereof. In a particularly preferred embodiment, the anti-dandruff agent is piroctone olamine. Without wishing to adhere to any theory, the present inventors believe that the deposition enhancer can only be applied to piroctone olamine or azole-based antifungal agents (especially climbazole) because both can be stabilized and resolved into micelles, and deposition can be improved by reducing the solubility of the active ingredient in the system. Typically, the hair care composition of the invention comprises the anti-dandruff agent in an amount of 0.01 to 10%, more preferably 0.01 to 5%, more preferably even 0.05 to 2%, and most preferably 0.05 to 1.5%, based on the total weight of the hair care composition and includes all intervals therein. The pH of the hair care composition is preferably equal to or greater than 4.0, more preferably in the range of 4.0 to 7.0. It is preferred if the hair care composition also includes other surfactants in addition to the polyhydroxylated fatty acid amide. Examples of suitable anionic surfactants are alkyl sulfates, alkyl ether sulfates, alkaryl sulfonates, alkanoyl isethionates, alkyl succinates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, N-alkyl sarcosinates, 1176086 of 26 alkyl phosphates, alkyl ether phosphates and alkyl ether carboxylic acids and their salts, especially their sodium, magnesium, ammonium salts and mono-, di- and triethanolamine. The alkyl and acyl groups generally contain from 8 to 18, preferably from 10 to 16 carbon atoms and may be unsaturated. Alkyl ether sulfates, alkyl ether sulfosuccinates, alkyl ether phosphates and alkyl ether carboxylic acids and their salts may contain from 1 to 20 ethylene oxide or propylene oxide units per molecule.Typical anionic cleaning surfactants for use in the compositions of the invention include, but are not limited to, sodium oleyl succinate, ammonium lauryl sulfosuccinate, sodium lauryl sulfate, sodium lauryl ether sulfate, sodium lauryl ether sulfosuccinate, ammonium lauryl sulfate, sodium dodecylbenzene sulfonate, triethanolamine dodecylbenzene sulfonate, sodium cocoyl isethionate, sodium lauryl isethionate, lauryl ether carboxylic acid, sodium N-lauryl sarcosinate, or mixtures thereof. Preferred anionic cleaning surfactants are alkyl sulfates and alkyl ether sulfates. The preferred alkyl sulfates are C12-18 alkyl sulfates, more preferably C12-18 alkyl sulfates, preferably in the form of a salt with a solubilizing cation such as sodium, potassium, ammonium, or substituted ammonium. Examples are sodium lauryl sulfate (SLS) or sodium dodecyl sulfate (SDS).It is particularly preferred that the anionic cleaning surfactant be an alkyl ether sulfate. The preferred alkyl ether sulfates are those with the formula R3O(CH2CH2O)nSO3M; where R3 is an alkyl or alkenyl group having 8 to 18 (preferably 12 to 18) carbon atoms; n is a number with an average value greater than at least 0.5, preferably between 1 and 3, most preferably between 2 and 3; and M is a solubilizing cation such as sodium, potassium, ammonium, or substituted ammonium. An example is sodium lauryl ether sulfate (SLES). 1176086 of 26 The preferred alkyl ether sulfate is sodium lauryl ether sulfate having an average degree of ethoxylation of 0.5 to 3, preferably 1 to 3, more preferably 2 to 3. Anionic cleansing surfactants are generally present in the hair care composition of the present invention at a level of 0.5 to 45%, more preferably 1.5 to 35% and most preferably 5 to 20% based on the total weight of the hair care composition and including all ranges therein. The hair care composition may also comprise other nonionic surfactants in addition to the polyhydroxylated fatty acid amide, which may be included in an amount of 0.1 to 10%, more preferably 0.5 to 8%, and most preferably 1 to 5%, based on the total weight of the hair care composition and including all ranges therein. Examples of suitable nonionic surfactants include condensation products of linear or branched primary or secondary aliphatic (C8-C18) alcohols or phenols with alkylene oxides, usually ethylene oxide, and generally having 6 to 30 ethylene oxide groups. Alkyl ethoxylates are preferred, most preferably alkyl ethoxylates having the formula R4-(OCH2CH2)mOH, where R4 is an alkyl chain having 12 to 15 carbon atoms and m is 5 to 9. Other suitable nonionic surfactants include mono- or dialkylalkanolamides. Examples include coco-mono- or diethanolamide and coco-mono-isopropanolamide. 1176086 of 26 Other nonionic surfactants that may be included in the compositions of the invention are alkylpolyglycosides (APGs). Typically, an APG comprises an alkyl group connected (optionally by a bridging group) to a block of one or more glycosyl groups. Preferred APGs are defined by the following formula: R5O-(G)k, where R5 is a linear or branched alkyl group, which may be saturated or unsaturated, and G is a saccharide group. R5 may represent an average alkyl chain length from C5 to C20. Preferably, R5 represents an average alkyl chain length from C8 to C12. Most preferably, the value of R5 is between 9.5 and 10.5. G may be selected from C5 or C6 monosaccharide residues and is preferably a glucoside. G may be selected from the group comprising glucose, xylose, lactose, fructose, mannose, and their derivatives. Preferably, G is glucose. The degree of polymerization, k, may have a value from 1 to 10 or more; preferably, the value of k is between 1.1 and 2; most preferably, the value of k is between 1.3 and 1.5.The alkylpolyglycosides suitable for use in the invention are commercially available and include, for example, those materials identified as: Oramix NS10 from Seppic; Plantaren 1200 and Plantaren 2000 from Henkel. The hair care composition may also comprise amphoteric or zwitterionic surfactants, which may be included in a quantity 1176086 of 26 from 0.1 to 10%, more preferably from 0.5 to 8% and more preferably from 1 to 5%, based on the total weight of the hair care composition and including all intervals therein. Examples include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl sulfobetaines (sultaines), alkyl amphoacetates, alkyl amphopropionates, and alkyl amidopropyl hydroxysultaines, wherein the alkyl group has from 8 to 19 carbon atoms. Preferably, the co-surfactant is a betaine surfactant. Typical amphoteric and zwitterionic surfactants for use in the invention include lauryl amine oxide, cocodimethyl sulfopropyl betaine, lauryl betaine, cocamidopropyl betaine, and sodium cocoamphoacetate. Cocamidopropyl betaine (CAPB) is particularly preferred. Mixtures of any of the above amphoteric or zwitterionic surfactants may also be suitable. Preferred mixtures are those of cocamidopropyl betaine with other amphoteric or zwitterionic surfactants as previously described. Another preferred amphoteric or bipolar surfactant is sodium cocoamphoacetate. The composition may also include a cationic polymer. Suitable cationic polymers may be homopolymers or composed of two or more types of monomers. The molecular weight of the polymer will generally be between 5,000 and 10,000,000 g / mol, normally at least 10,000 g / mol and preferably from 100,000 to 2,000,000 g / mol. The polymers will have groups containing cationic nitrogen, such as 1176086 of 26 quaternary ammonium or protonated amino groups, or a mixture thereof. The group containing cationic nitrogen will generally be present as a substituent on a fraction of all the monomeric units of the cationic polymer. Thus, when the polymer is not a homopolymer, it may contain non-cationic spacer monomeric units. The ratio of cationic to non-cationic monomer units is selected to provide a polymer that has a cationic charge density in the required range. Suitable cationic polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functionalities with water-soluble spacer monomers such as (meth)acrylamide, alkyl and dialkyl (meth)acrylamides, alkyl (meth)acrylate, vinyl caprolactone, and vinyl pyrrolidine. The alkyl- and dialkyl-substituted monomers preferably have C1-C7 alkyl groups, more preferably C1-C3 alkyl groups. Other suitable spacers include vinyl esters, vinyl alcohol, maleic anhydride, propylene glycol, and ethylene glycol. Preferably, the cationic polymer is a cationic polysaccharide polymer such as cationic cellulose derivatives, cationic starch derivatives, and cationic guar gum derivatives. Suitablely, such cationic polysaccharide polymers have a molecular weight of 100,000 g / mol to 2,300,000 g / mol, more preferably from 150,000 g / mol to 2,000,000 g / mol. Such cationic polysaccharide polymers preferably have a cationic charge density of 0.1 to 4 meq / g. 1176086 of 26 Cationic polysaccharide polymers suitable for use in the compositions of this invention include those represented by the general formula: AO-[R6-N+(R7)(R8)(R9)X-] where: A is an anhydroglucose residue group, such as a starch or cellulose anhydroglucose residue. R6 is an alkylene, oxyalkylene, polyoxyalkylene, or hydroxyalkylene group, or a combination thereof. R7, R8, and R9 independently represent alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, or alkoxyaryl groups, each group containing up to approximately 18 carbon atoms. The total number of carbon atoms for each cationic residue (i.e., the sum of the carbon atoms in R7, R8, and R9) is preferably approximately 20 or less, and X is an anionic counterion. Cationic cellulose is available from Amerchol Corp. (Edison, NJ, USA) in its Polymer JR (registered trademark) and LR (registered trademark) polymer series, as hydroxyethylcellulose salts reacted with trimethylammonium epoxide, referred to in the industry (CTFA) as Polyquaternium 10. Another type of cationic cellulose includes quaternary ammonium polymer salts of hydroxyethylcellulose reacted with lauryl dimethyl ammonium epoxide, referred to in the industry (CTFA) as Polyquaternium 24. These materials are available from Amerchol Corp. (Edison, NJ, USA) under the trade name Polymer LM-200. 1176086 of 26 Other suitable cationic polysaccharide polymers include cellulose ethers containing quaternary nitrogen (e.g., as described in U.S. Patent 3,962,418) and copolymers of etherified cellulose and starch (e.g., as described in U.S. Patent 3,958,581). A particularly preferred type of cationic polysaccharide polymer that can be used in the compositions of the present invention is a cationic derivative of guar gum, such as guar hydroxypropyltrimonium chloride (for example, commercially available from Solvay in its Jaguar series of brands, or from Ashland in its N-Hance series of brands). Examples of such materials are Jaguar® C-13S, Jaguar® C-14S, Jaguar® C-17, Jaguar® Excel, Jaguar® C-162, Jaguar® C-500, Jaguar® Optima, Jaguar® LS, N-Hance™ BF17, N-Hance™ BF13, and N-Hance™ CCG45. Mixtures of any of the above cationic polymers may be used. The cationic polymer preferably comprises cationic cellulose derivatives, cationic guar gum derivatives, or mixtures thereof. Guar hydroxypropyltrimonium chloride is particularly preferred. When used, the cationic polymer will generally be present in the hair care composition of the present invention in an amount of 0.001 to 1% by weight of the hair care composition, more preferably 0.01 to 0.5%, and much more preferably 0.03 to 0.3%, based on the total weight of the hair care composition and includes all ranges therein. 1176086 of 26 Preferably, the composition of the invention further comprises a suspending agent. Suitable suspending agents are selected from polyacrylic acids, crosslinked polymers of acrylic acid, copolymers of acrylic acid with a hydrophobic monomer, copolymers of monomers containing carboxylic acid and acrylic esters, crosslinked copolymers of acrylic acid and acrylate esters, heteropolysaccharide gums, and crystalline derivatives of long-chain acyls. The long-chain acyl derivative is desirably selected from ethylene glycol stearate, alkanolamides of fatty acids having 16 to 22 carbon atoms, and mixtures thereof. Ethylene glycol distearate and polyethylene glycol distearate 3 are preferred long-chain acyl derivatives because they impart pearlescence to the composition. The polyacrylic acid is commercially available as Carbopol 420, Carbopol 488, or Carbopol 493.Acrylic acid polymers crosslinked with a polyfunctional agent can also be used; these are readily available commercially as Carbopol 910, Carbopol 934, Carbopol 941, and Carbopol 980. An example of a suitable copolymer of a carboxylic acid containing acrylic acid monomer and esters is Carbopol 1342. All Carbopol (registered trademark) materials are available from Goodrich. Suitable crosslinked acrylic acid polymers and acrylate esters are Pemulen TR1 or Pemulen TR2. A suitable heteropolysaccharide gum is xanthan gum, for example, that available as Kelzan mu. Mixtures of any of the above suspending agents may be used. A mixture of crosslinked acrylic acid polymer and long-chain crystalline acyl derivative is preferred. 1176086 of 26 The suspending agent is generally present in the hair care composition of this invention in an amount of 0.1 to 10%, more preferably 0.5 to 6%, and much more preferably 0.5 to 4%, based on the total weight of the hair care composition and includes all intervals therein. The shampoo compositions of the invention are generally aqueous, that is, they have water or an aqueous solution or a lyotropic liquid crystalline phase as their main component. The composition will typically comprise 50 to 98% water, more preferably 60 to 90%, based on the total weight of the hair care composition. Preservatives may also be incorporated into the hair care composition of this invention to protect against the growth of potentially harmful microorganisms. Suitable traditional preservatives include alkyl esters of parahydroxybenzoic acid, hydantoin derivatives, propionate salts, and a variety of quaternary ammonium compounds. Illustrative, but not restrictive, examples of the types of preservatives that may be used in this invention include, for example, phenoxyethanol, sodium salicylate, methylparaben, butylparaben, propylparaben, diazolidinyl urea, sodium dehydroacetate, benzyl alcohol, sodium benzoate, iodopropynyl butylcarbamate, caprylyl glycol, disodium EDTA, or mixtures thereof. In a particularly preferred embodiment, the preservative is phenoxyethanol, sodium salicylate, or a mixture thereof. 1176086 of 26 are preferably used in quantities ranging from 0.01 to 2% by weight of the hair care composition. The hair care composition of the present invention may contain other ingredients that are common in the art to improve physical properties and performance. Suitable ingredients include, but are not limited to, fragrances, dyes and pigments, pH adjusting agents, pearlizers or opacifiers, viscosity modifiers, thickeners, and natural hair nutrients such as botanicals, fruit extracts, sugar derivatives, and amino acids. Such ingredients typically and collectively constitute less than 20% by weight of the composition, and preferably from 0.0 to 15% by weight, and more preferably from 0.01 to 12% by weight of the composition, including all intervals therein. The compositions of the invention are primarily intended for topical application to the scalp and / or at least a portion of an individual's hair, either in compositions that are left on or rinsed off, preferably in compositions that are rinsed off like shampoos. The following examples are provided to facilitate understanding of the present invention. The examples are not provided to limit the scope of the claims. Examples Example 1 1176086 of 26 This example demonstrates the deposition of anti-dandruff agents using polyhydroxylated fatty acid amide surfactants. The compositions were prepared according to the formulations detailed in Table 1. All ingredients are expressed as a percentage by weight of the total formulation and as the level of active ingredient. Table 1 Ingredient Samples 1 2 3 Sodium laureth sulfate (1EO) 13.00 — — Piroctone olamine 0.50 0.50 0.50 Disodium EDTA 0.05 0.05 0.05 Sodium benzoate 0.50 0.50 0.50 Carbopol 980 0.35 0.35 0.35 Guar hydroxypropyltrimonium chloride 0.20 0.20 0.20 Dimethiconol* 0.78 0.78 0.78 Dimethiconac 0.52 0.52 0.52 Capryloyl / caproyl methylglucamide -- 13.00 -- Lauroyl / myristoyl methylglucamide -- -- 13.00 Perfume 0.80 0.80 0.80 Citric acid 0.42 1.54 1.45 Sodium chloride 1.00 1.00 1.00 Water at 100 to 100 to 100 1176086 of 26 a. Commercial guar hydroxypropyltrimonium chloride has a weight average molecular weight of 1.0 to 1.5 million g / mol and a degree of substitution of 0.16 to 0.20 from Lamberti. b. Commercial Dimethiconol having a particle size of 0.2 pm from Dow Silicones Corporation. c. Commercial Dimethiconol having a particle size of 10 pm from Dow Silicones Corporation. d. Capryloyl / caproyl methyl glucoamide commercially available under the trade name Glucotain® Clear by Clariant. e. Lauroyl / myristoyl methyl glucoamide commercially available under the trade name Glucotain® Clear by Clariant. Methods Citric acid was added to the samples to adjust the pH to 4.3. Approximately 0.2 grams of the test sample were taken from artificial skin (VITROSKIN from the IMS test group). It was diluted with 1.8 mL of water and rubbed with a plastic swab for 30 seconds. The artificial skin surface was then rinsed twice with water, first with 4 mL of water for 30 seconds and then again with 4 mL of water for 30 seconds. The deposition of piroctone olamine on the skin (10.75 cm² per plate) was measured using HPLC. Results The average deposition (from five such experiments) is reported in Table 2 (error represents the standard deviation for duplicate measurements). 1176086 of 26 Table 2 Samples 1 2 3 Piroctone olamine deposition (μg / plate) 9.75±0.76 10.74±0.81 30.56±6.20 The data in Table 2 indicate that sample 3 comprising lauroyl / myristoyl methylglucamide provided significantly better piroctone olamine deposition (p < 0.01) compared to samples 1 and 2, while sample 2 showed comparable piroctone olamine deposition to sample 1. Example 2 This example demonstrates the effect of silicone oil on the deposition of anti-dandruff agents on the scalp. All ingredients are expressed as a percentage by weight of the total formulation and as the level of active ingredient. Table 3 Ingredient Samples 4 5 6 7 Piroctone olamine 0.50 0.50 0.50 0.50 Disodium EDTA 0.05 0.05 0.05 0.05 Sodium benzoate 0.50 0.50 0.50 0.50 Carbopol 980 0.35 0.35 0.35 0.35 1176086 of 26 Guar Hydroxypropyltrimonium Chloride 0.20 0.20 0.20 0.20 Dimethiconol* — 1.00 2.00 3.00 Lauroyl / Myristoyl Methyl Glucamide 13.00 13.00 13.00 13.00 Perfume 0.80 0.80 0.80 0.80 Sodium Chloride 1.00 1.00 1.00 1.00 Water 100 100 100 100 Methods The same protocol was used to measure the deposition of piroctone olamine on artificial skin as described in Example 1. Results The average deposition (from five such experiments) is reported in the Table (error represents the standard deviation for duplicate measurements). Table 4 Samples 4 5 6 7 Piroctone olamine deposition (μg / plate) 5.44±0.76 7.70±1.41 9.63±1.65 15.82±4.89 Samples 5 to 7 comprising silicone compounds provided significantly better piroctone olamine deposition (p < 0.05) than sample 4. 1176086 of 26 MOELLER & CO. SA - 30529767664 Digitally signed by PORTALTRAM ITES - INPI Date: 2020.11.10 12:56:57 -03:00 Reason: Digitally Signed by the INPI Location: Buenos Aires, Argentina 1176086

Claims

1. A hair care composition characterized in that it comprises: (a) a polyhydroxylated fatty acid amide surfactant of general formula (I): (FORMULA 1) wherein R1 is a C1-4 alkyl group or C1-4 alkyl groups substituted with hydroxy; R2CO is a saturated or unsaturated, linear or branched C12-18 acyl group; (b) a silicone compound; and (c) from 0.01 to 10% by weight of an anti-dandruff agent selected from piroctone olamine, azole-based antifungal agents, and mixtures thereof. Fourteen claims follow.