Hair care composition

Abstract

A hair care composition is disclosed, comprising: (i) benzophenone or a benzophenone derivative, which is one or more components selected from benzophenone, benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-6, benzophenone-7, benzophenone-8, benzophenone-10 and benzophenone-12; (ii) piroctone olamine; (iii) a silicone compound; a cosmetically acceptable carrier; wherein the amount of the benzophenone or benzophenone derivative is 0.2 to 10% by weight of the total composition. It shows improved deposition and stability of piroctone olamine.

Description

Technical Field

[0001] The present invention relates to hair care compositions. More particularly, the present invention relates to hair care compositions comprising piroctone olamine. Background Art

[0002] Dandruff is a disease experienced by many people worldwide. Dandruff disease changes from mild symptoms (such as skin peeling) to severe inflammation and scalp itching. Some people believe that Malassezia yeast (such as Malassezia furfur) is the main cause of dandruff, and although this may not represent the complete scientific picture of this situation, Malassezia yeast does show that it is closely related to dandruff. Therefore, the strategy commonly used to treat dandruff is to apply antifungal agents topically, such as zinc pyrithione (ZnPTO), piroctone olamine, climbazole and ketoconazole, which are usually delivered by shampoo.

[0003] Piroctone olamine (also known as ) is a compound commonly used in the treatment of fungal infections. Piroctone olamine is the ethanolamine salt of the hydroxamic acid derivative piroctone. Piroctone olamine has antifungal properties, which makes it ideal for controlling the root cause of dandruff, the commonly present fungus called Malassezia globosa. It is commonly used in anti-dandruff shampoos as a substitute for the commonly used compound zinc pyrithione. Typically, piroctone olamine is dissolved in a base composition of a shampoo, which includes a surfactant, water, silicone, a polymer, and coloring and fragrance ingredients. When the user applies the composition to the hair and scalp, some of the compounds of piroctone olamine are deposited thereon.

[0004] Typically, the efficacy of anti-dandruff shampoos or conditioners depends on the amount of anti-dandruff actives deposited on the scalp and hair, because more deposition means higher bioavailability. However, it is well known that piroctone olamine is light unstable, and the deposited piroctone olamine is not bioavailable because piroctone olamine tends to react with UV radiation, which causes it to destabilize. By using UV light stabilizers or sunscreens, this destabilization can be avoided to a certain extent. Efforts have also been made to improve the antimicrobial efficacy of piroctone olamine by combining piroctone olamine with "enhancement" technology. Summary of the invention

[0005] The inventors of the present invention have identified a new method for improving the deposition of anti-dandruff agents such as piroctone olamine and at the same time improving the photostability of piroctone olamine. We have determined that if piroctone olamine, a silicone compound and a specific benzophenone or benzophenone derivative are co-formulated into a composition, both the deposition and photostability of piroctone olamine can be improved.

[0006] According to a first aspect, a hair care composition is disclosed, comprising:

[0007] (i) benzophenone or a benzophenone derivative, which is one or more components selected from benzophenone, benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-6, benzophenone-7, benzophenone-8, benzophenone-10 and benzophenone-12;

[0008] (ii) piroctone olamine;

[0009] (iii) a siloxane compound; and

[0010] (iv) a cosmetically acceptable carrier;

[0011] The amount of benzophenone or benzophenone derivative is 0.2 to 10% by weight of the total composition.

[0012] In a second aspect, the present invention relates to a method for preparing a hair care composition according to any embodiment of the first aspect of the present invention, the method comprising the steps of:

[0013] (a) mixing the benzophenone or benzophenone derivative with the silicone compound to form a premix;

[0014] (b) mixing the premix of step (a) with other ingredients to form a hair care composition.

[0015] According to a third aspect, a method of treating dandruff is disclosed, comprising the step of applying thereon the composition of the first aspect. DETAILED DESCRIPTION

[0016] For the avoidance of doubt, any feature of one aspect of the present invention may be used in any other aspect of the present invention. The word "comprising" is intended to mean "including", but not necessarily "consisting of" or "composed of". In other words, the steps or options listed do not need to be exhaustive. It should be noted that the examples given in the following description are intended to illustrate the present invention and are not intended to limit the present invention to those examples themselves. Similarly, all percentages are weight / weight percentages unless otherwise indicated. Except in the operating and comparative examples, or in the case of otherwise explicitly indicated, all the numbers indicating the amount of materials or reaction conditions, the physical properties of materials and / or the use in this specification and claims are modified by the word "about". Numerical ranges expressed in the format of "x to y" should be understood to include x and y. When multiple preferred ranges are described in the form of "x to y" for a particular feature, it should be understood that all ranges combining different endpoints are also considered. Unless otherwise specified, as used herein, the indefinite article "a" or "an" and its corresponding definite article "the" refer to at least one, or one or more. The various features of the invention mentioned in the above sections are appropriately applicable to other sections mutatis mutandis. Therefore, features specified in one section may be appropriately combined with features specified in other sections. Any section headings are added for convenience only and are not intended to limit the present disclosure in any way.

[0017] As used herein, "hair care composition" is meant to include compositions for topical application to the hair or scalp of mammals, especially humans. Topical refers to the application of the composition to the external surface of the body. In the present invention, this is achieved by applying the composition to the hair or scalp. Such compositions can generally be classified as leave-on or rinse-off, and include any product applied to improve the appearance, cleaning, odor control or general aesthetics of the scalp and hair. The hair care composition of the present invention may be in the form of a liquid, lotion, cream, foam, scrub, gel, shampoo, conditioner, shower gel or soap bar. The hair care composition of the present invention is preferably a leave-on composition. Alternatively, the hair care composition of the present invention is a rinse-off composition. Compositions that achieve the desired benefits by ingestion into the human body are not included in the scope of the present invention.

[0018] Benzophenone or benzophenone derivatives

[0019] The composition according to the present invention comprises benzophenone or a benzophenone derivative, wherein the benzophenone or the benzophenone derivative is one or more components selected from benzophenone, benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-6, benzophenone-7, benzophenone-8, benzophenone-10 and benzophenone-12, more preferably selected from benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-6, benzophenone-8, benzophenone-10 and benzophenone-12, more preferably selected from benzophenone-2, benzophenone-3, benzophenone-6, benzophenone-8 and benzophenone-10, further preferably selected from benzophenone-2, benzophenone-3 and benzophenone-8 thereof, further preferably selected from benzophenone-2 and benzophenone-3, most preferably benzophenone-3.

[0020] LogP

[0021] The partition coefficient (logP) describes the tendency of a compound to dissolve in an immiscible two-phase system of lipids (fats, oils, organic solvents) and water. A low logP value means that the compound has a higher affinity for the aqueous phase (more hydrophilic); a high logP value indicates a higher concentration in the organic phase (i.e., the compound is more lipophilic).

[0022] The logP value is a constant defined in the following manner: LogP = log10 (partition coefficient), partition coefficient, P = [organic] / [aqueous]; where [ ] represents the concentration of the solute in the organic and aqueous fractions.

[0023] The log P values ​​of benzophenone, benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-6, benzophenone-7, benzophenone-8, benzophenone-10, and benzophenone-12 are 3.21, 3.15, 3.09, 3.99, 4.78, 4.51, 4.31, 4.66, and 7.56, respectively.

[0024] Without wishing to be bound by theory, the inventors of the present invention believe that lipophilic benzophenone or benzophenone derivatives can be combined with piroctone olamine and a carrier, resulting in co-deposition of piroctone olamine with the carrier. On the one hand, lipophilic benzophenone or benzophenone derivatives can be easily dispersed in a carrier, such as polydimethylsiloxane with a logP of 2.67. On the other hand, the special aromatic structure of benzophenone or benzophenone derivatives can interact with piroctone olamine, thereby improving the carrier capacity of piroctone olamine, thereby improving the deposition of piroctone olamine.

[0025] The amount of benzophenone or benzophenone derivative in the composition of the present invention will depend on the type of hair care composition and the amount of piroctone olamine used. The composition according to the present invention comprises 0.2 to 10% by weight, preferably 0.2 to 5% by weight, more preferably 0.3 to 2% by weight, further preferably 0.4 to 1% by weight of the benzophenone or benzophenone derivative, based on the weight of the composition.

[0026] Piroctone olamine

[0027] Piroctone olamine is the ethanolamine salt of the hydroxamic acid derivative piroctone, which is a typical antimicrobial active substance. It is commonly known as hydroxymethyl octopirox olamine and its trade name is

[0028] Piroctone olamine according to the present invention is a 1:1 compound of 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone and 2-aminoethanol, and is also called 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone monoethanolamine salt. CAS No. is 68890-66-4, and the compound has the following general formula:

[0029]

[0030] Several anti-dandruff hair care products contain piroctone olamine. It was found that the dissolved intact piroctone olamine molecule is the only biologically active form of piroctone olamine. When using hair care products with piroctone olamine, piroctone olamine dissociates and undergoes photooxidation, and the stability of the biologically active substance is affected due to this photooxidation, which reduces its anti-dandruff efficacy.

[0031] The amount of piroctone olamine in the composition of the present invention will depend on the type of hair care composition and the exact nature of the other anti-dandruff agents used. It is preferred that the composition comprises 0.1 to 10% by weight, more preferably 0.5 to 5% by weight, and further preferably 0.5 to 2% by weight of the piroctone olamine, based on the weight of the composition.

[0032] The weight ratio of benzophenone or a benzophenone derivative to piroctone olamine is preferably 1:0.1 to 1:10, more preferably 1:0.5 to 1:5, further preferably 1:1 to 1:3.

[0033] Siloxane

[0034] The hair care compositions of the present invention comprise a silicone compound.

[0035] Suitable silicones include polydiorganosiloxanes, polydimethylsiloxanes, which have the CTFA designation dimethicone. Also suitable for use in the compositions of the present invention, particularly shampoos and conditioners, are polydimethylsiloxanes having hydroxyl end groups, which have the CTFA designation dimethiconol.

[0036] Preferably, the viscosity of the emulsified silicone is at least 10,000 cSt at 25°C, preferably the viscosity of the silicone is at least 60,000 cSt, most preferably at least 500,000 cSt, and ideally at least 1,000,000 cSt. Preferably, the viscosity does not exceed 10 9 cst for easy preparation.

[0037] Examples of suitable preformed emulsions include Xiameter MEM 1785 and microemulsion DC2-1865 available from Dow Corning. These are emulsions / microemulsions of dimethiconol. Crosslinked silicone gums can also be obtained in pre-emulsified form, which is advantageous for formulation convenience. A further preferred silicone type for inclusion in shampoos and conditioners is amino-functional silicones. "Amino-functional silicones" refers to silicones containing 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 "amino-terminated polydimethylsiloxanes".

[0038] Specific examples of amino functional silicones suitable for use herein are amino silicone oils DC2-8220, DC2-8166 and DC2-8566 (all ex Dow Corning).

[0039] It is preferred that the total amount of siloxane is from 0.01 to 10 wt%, more preferably from 0.1 to 5 wt%, most preferably from 0.5 to 3 wt%.

[0040] Hair care composition

[0041] According to another aspect of the present invention, a hair care composition of the first aspect is disclosed. Preferably, the composition is a shampoo, a conditioner, a hair cream, a hair gel, a hair essence, a mousse or a hair oil. More preferably, the composition is a shampoo composition.

[0042] The compositions of the present invention, especially shampoos, are preferably formulated with anionic surfactants such as alkyl sulfates and / or alkoxylated alkyl sulfate surfactants. These anionic surfactants are preferably present in an amount of 2 to 16%, more preferably 3 to 16%, by weight of the composition. Preferred alkyl sulfates are C8-18 alkyl sulfates, more preferably C12-18 alkyl sulfates, preferably in the form of salts with solubilizing cations such as sodium, potassium, ammonium or substituted ammonium. Examples are sodium lauryl sulfate (SLS) or sodium dodecyl sulfate (SDS).

[0043] Preferred alkyl ether sulfates are those having the formula: RO(CH2CH2O) n SO3M; wherein R is an alkyl or alkenyl group having 8 to 18 (preferably 12 to 18) carbon atoms; n is a number having an average value greater than at least 0.5, preferably 1-3, more preferably 1-2; M is a solubilizing cation such as sodium, potassium, ammonium or substituted ammonium. An example is sodium lauryl ether sulfate (SLES).

[0044] A preferred alkoxylated alkyl sulfate anionic surfactant is sodium lauryl ether sulfate (SLES) having an average degree of ethoxylation of 0.5 to 3, preferably 1 to 3.

[0045] The composition according to the invention optionally and preferably further comprises a betaine surfactant. In a preferred embodiment, the composition comprises 0.1 to 10 wt. %, preferably 0.5 to 8 wt. %, more preferably 1 to 5 wt. % of a betaine surfactant, preferably an alkylamidopropyl betaine, such as cocamidopropyl betaine.

[0046] Preferably, the hair care composition of the present invention in the form of a shampoo comprises a surfactant which is sodium lauryl sulfate, sodium lauryl ether sulfate, sodium lauryl ether sulfosuccinate, ammonium lauryl sulfate, ammonium lauryl ether sulfate, sodium cocoyl isethionate and lauryl ether carboxylic acid, coco betaine, cocamidopropyl betaine, sodium cocoamphoacetate or a mixture thereof.

[0047] Preferably, the hair care compositions of the present invention comprise from 1% to 50%, preferably from 2% to 40%, more preferably from 4% to 25% total surfactants.

[0048] The hair conditioning composition comprises a conditioning surfactant selected from cationic surfactants, used alone or in admixture. Preferably, the cationic surfactant has the formula N+R1R2R3R4, wherein R1, R2, R3 and R4 are independently (C1 to C30) alkyl or benzyl. Preferably, one, two or three of R1, R2, R3 and R4 are independently (C4 to C30) alkyl, and the other one or more groups of R1, R2, R3 and R4 are (C1-C6) alkyl or benzyl. More preferably, one or two of R1, R2, R3 and R4 are independently (C6 to C30) alkyl, and the other R1, R2, R3 and R4 groups are (C1-C6) alkyl or benzyl. Optionally, the alkyl group may contain one or more ester (-OCO- or -COO-) and / or ether (-O-) bonds within the alkyl chain. The alkyl group may optionally be substituted with one or more hydroxyl groups. The alkyl group may be straight or branched and, for alkyl groups having 3 or more carbon atoms, may be cyclic. The alkyl group may be saturated or may contain one or more carbon-carbon double bonds (e.g., oleyl). The alkyl group may optionally be ethoxylated with one or more ethyleneoxy groups on the alkyl chain.

[0049] Cationic surfactants suitable for use in conditioner compositions according to the present invention include hexadecyl trimethyl ammonium chloride, behenyl trimethyl ammonium chloride, hexadecyl pyridinium chloride, tetramethyl ammonium chloride, tetraethyl ammonium chloride, octyl trimethyl ammonium chloride, dodecyl trimethyl ammonium chloride, hexadecyl trimethyl ammonium chloride, octyl dimethyl benzyl ammonium chloride, decyl dimethyl benzyl ammonium chloride, stearyl dimethyl benzyl ammonium chloride, didodecyl dimethyl ammonium chloride, dioctadecyl dimethyl ammonium chloride, tallow trimethyl ammonium chloride, dihydrogenated tallow dimethyl ammonium chloride (e.g. Arquad 2HT / 75 from Akzo Nobel), coconut oil trimethyl ammonium chloride, PEG-2-oleyl ammonium chloride and its corresponding hydroxide. Other suitable cationic surfactants include those materials with CTFA names Quaternium-5, Quaternium-31 and Quaternium-18. Mixtures of any of the foregoing materials may also be suitable. A particularly useful cationic surfactant for use in conditioners according to the present invention is cetyl trimethyl ammonium chloride, for example commercially available from Hoechst Celanese as GENAMIN CTAC. Another particularly useful cationic surfactant for use in conditioners according to the invention is behenyltrimethylammonium chloride, commercially available, for example, as GENAMIN KDMP from Clariant. Yet another preferred cationic surfactant is stearamidopropyl dimethylamine.

[0050] The most preferred cationic surfactant for use in the composition is stearamidopropyl dimethylamine, behenyl trimethyl ammonium chloride or stearyl trimethyl ammonium chloride.In conditioners of the invention, the cationic surfactant is typically present at a level of from 0.1 to 5%, preferably from 0.5 to 2.5% by weight of the composition.

[0051] The hair conditioning compositions of the present invention may preferably also additionally comprise a fatty alcohol.It is believed that the combined use of a fatty alcohol and a cationic surfactant in the conditioning composition is particularly advantageous as this results in the formation of a lamellar phase in which the cationic surfactant is dispersed.

[0052] Representative fatty alcohols contain 8 to 22 carbon atoms, more preferably 16 to 22 carbon atoms. Fatty alcohols are typically compounds containing straight chain alkyl groups. Examples of suitable fatty alcohols include cetyl alcohol, stearyl alcohol, and mixtures thereof. The use of these materials is also advantageous because they contribute to the overall conditioning properties of the compositions of the present invention.

[0053] The content of fatty alcohol in the conditioner of the present invention is generally 0.5 to 10% by weight of the composition, preferably 0.1 to 8%, more preferably 0.2 to 7%, most preferably 0.3 to 6%. The weight ratio of cationic surfactant to fatty alcohol is suitably 1:1 to 1:10, more preferably 1:1.5 to 1:8, optimally 1:2 to 1:5.

[0054] It is also preferred that the hair care composition of the present invention comprises a cosmetic ingredient. Preferably, the cosmetic ingredient is selected from silicones, antimicrobial agents other than antidandruff agents, foam enhancers, fragrances, encapsulates (e.g. encapsulated fragrances), dyes, colorants, pigments, preservatives, thickeners, proteins, phosphates, buffers, pH adjusters, pearlescent agents (e.g. mica, titanium dioxide, titanium dioxide coated mica, glycol distearate (INCI glycol distearate)) and / or sunscreens, viscosity modifiers, emollients, sunscreens, emulsifiers, sensory actives (e.g. menthol and menthol derivatives), vitamins, mineral oils, essential oils, lipids, natural actives, glycerin, natural hair nutrients such as plant extracts, fruit extracts, sugar derivatives and amino acids, microcrystalline cellulose and mixtures thereof.

[0055] Preferably, the hair care composition of the present invention comprises 0.01 to 20 wt% of at least one cosmetic ingredient, more preferably 0.05 to 10 wt%, still more preferably 0.075 to 7.5 wt%, and most preferably 0.1 to 5 wt% of at least one cosmetic ingredient, based on the weight of the total composition.

[0056] The hair care compositions of the present invention may also contain synergistic antimicrobial compounds that provide synergistic antimicrobial benefits when used in combination with piroctone olamine to enhance its properties and further inhibit the growth of Malassezia furfur. Non-limiting examples of these compounds include compounds with alcohol groups (e.g., honokiol, magnolol, or paeonol), piperazines, and phenolic compounds found in natural plant extracts, i.e., thymol and terpeniol.

[0057] The composition may additionally comprise a vitamin B3 compound. A preferred vitamin B3 compound is niacinamide.

[0058] Nicotinamide is known to secrete AMPs (antimicrobial proteins) from keratinocytes. The AMPs so secreted provide for improving immunity, for example, of the scalp. Thus, in the case of the use of nicotinamide, the anti-dandruff efficacy can be enhanced by using nicotinamide, not only through antifungal activity, but also by strengthening the scalp's own antibacterial protective barrier. This combination can provide further long-lasting protection, for example up to 24 hours of antibacterial protection.

[0059] When present, it is preferred that hair care compositions of the invention comprise from 0.1% to 5%, more preferably from 0.5% to 5%, further preferably from 0.5% to 3% and optimally from 1.0% to 3.0% niacinamide by weight of the composition.

[0060] Shampoo

[0061] When the hair care compositions according to the invention are shampoos, they are typically aqueous, ie they have water or an aqueous solution or a lyotropic liquid-crystalline phase as their major component.

[0062] Suitably, the shampoo composition comprises from 50 to 98%, preferably from 60 to 92% water.

[0063] Preferably, the shampoo composition comprises one or more cationic polymers for conditioning the hair.

[0064] Suitable cationic polymers include homopolymers of cationically substituted monomers or may be formed from two or more types of monomers. The weight average (M) of the polymer w ) molecular weight is generally 100000 to 3 million Daltons. The polymer has cationic nitrogen-containing groups, such as quaternary ammonium or protonated amino groups, or mixtures thereof. If the molecular weight of the polymer is too low, the conditioning effect is poor. If it is too high, there may be problems with high extensional viscosity, resulting in stringiness of the composition when poured.

[0065] Cationic nitrogen-containing groups are usually present as substituents on a portion of the total monomer units of cationic polymers. Therefore, when the polymer is not a homopolymer, it may contain spacer non-cationic monomer units. Such polymers are described in the CTFA Cosmetic Ingredient Directory, 3rd edition. The ratio of cationic monomer units to non-cationic monomer units is selected to obtain a polymer with a cationic charge density in the desired range, which is generally 0.2 to 3.0 meq / g. The cationic charge density of the polymer is suitably determined by the Kjeldahl method, as described in the chemical test for nitrogen determination in the United States Pharmacopoeia.

[0066] Suitable cationic polymers include copolymers of vinyl monomers having cationic amine or quaternary ammonium functional groups and water-soluble spacer monomers such as (meth)acrylamide, alkyl and dialkyl (meth)acrylamide, alkyl (meth)acrylate, vinyl caprolactone and vinyl pyrrolidine. Alkyl and dialkyl substituted monomers preferably have C1-C7 alkyl groups, more preferably C1-3 alkyl groups. Other suitable spacers include vinyl esters, vinyl alcohol, maleic anhydride, propylene glycol and ethylene glycol.

[0067] The cationic amines can be primary, secondary or tertiary amines, depending on the particular species and the pH of the composition. In general, secondary and tertiary amines are preferred, particularly tertiary amines.

[0068] Amine-substituted vinyl monomers and amines can be polymerized in the amine form and then converted to ammonium by quaternization.

[0069] The cationic polymer may comprise a mixture of monomer units derived from amine-substituted and / or quaternary ammonium-substituted monomers and / or compatible spacer monomers.

[0070] Suitable cationic polymers, non-limiting examples of which include:

[0071] - cationic diallyl quaternary ammonium-containing polymers, including, for example, dimethyldiallylammonium chloride homopolymers and copolymers of acrylamide and dimethyldiallylammonium chloride, known in the industry (CTFA) as Polyquaternium 6 and Polyquaternium 7, respectively;

[0072] - inorganic acid salts of amino-alkyl esters of homopolymers and copolymers of unsaturated carboxylic acids having 3 to 5 carbon atoms (as described in US Pat. No. 4,009,256);

[0073] - Cationic polyacrylamides (as described in WO 95 / 22311).

[0074] Other cationic polymers that may be used include cationic polysaccharide polymers, such as cationic cellulose derivatives, cationic starch derivatives, and cationic guar gum derivatives.

[0075] A particularly suitable type of cationic polysaccharide polymer that can be used is a cationic guar gum derivative such as guar hydroxypropyltrimonium chloride (commercially available from Rhodia in its JAGUAR trademark series). Examples of such materials are JAGUAR C13S, JAGUAR C14 and JAGUAR C17.

[0076] Mixtures of any of the above cationic polymers may be used.

[0077] It is preferred that hair care compositions of the present invention comprise from 0.01 to 5%, preferably from 0.02 to 1%, more preferably from 0.05 to 0.8% of the cationic polymer.

[0078] The hair care compositions of the present invention may further comprise a cationic deposition polymer having an average molecular weight (M) of from 1 million to 2.2 million g / mol. w ) and a cationic polygalactomannan having a cationic degree of substitution of 0.13 to 0.3.

[0079] Polygalactomannan is a polysaccharide composed mainly of galactose and mannose units and is generally found in the endosperm material of seeds of leguminous plants such as guar, locust bean, honey locust, poinciana and other members of the leguminous family. Polygalactomannan consists of a main chain of 1→4 linked β-D-pyranosyl main chain units (also called mannoside units or residues) with repeated 1→6 linked α-D-galactosyl side groups (also called galactoside units or residues) branching from the carbon atom No. 6 of the pyranosyl residue in the polymer main chain. The polygalactomannans of different leguminous species differ from each other in the frequency of occurrence of galactoside side units branching from the polymannoside main chain. Mannoside and galactoside units are generally referred to as glycoside units or residues herein. The average ratio of mannoside to galactoside units in the polygalactomannan contained in guar gum (hereinafter referred to as "guar gum") is about 2:1.

[0080] Suitable cationic polygalactomannans include guar gum and hydroxyalkyl guar gum (eg hydroxyethyl guar gum or hydroxypropyl guar gum) which have been cationically modified by chemical reaction with one or more derivatizing agents.

[0081] In typical compositions, the amount of cationic polygalactomannan generally ranges from about 0.05 to 1%, preferably 0.1 to 0.8%, more preferably 0.2 to 0.6% by weight of the composition.

[0082] The hair care compositions of the present invention may additionally comprise anionic polymeric rheology modifiers, such as carboxylic acid polymers.

[0083] In the context of the present invention, the term "carboxylic acid polymer" generally refers to a homopolymer or copolymer obtained by the polymerization of ethylenically unsaturated monomers containing pendant carboxylic acid groups (hereinafter referred to as "carboxylic acid monomers").

[0084] Suitable carboxylic acid monomers generally have one or two carboxylic acid groups, one carbon-carbon double bond, and contain a total of 3 to about 10 carbon atoms, more preferably 3 to about 5 carbon atoms.

[0085] Specific examples of suitable carboxylic acid monomers include α-β-unsaturated monocarboxylic acids, such as acrylic acid, methacrylic acid, and crotonic acid; and α-β-unsaturated dicarboxylic acids, such as itaconic acid, fumaric acid, maleic acid, and aconitic acid. Salts, esters, or anhydrides of the above α-β-unsaturated monocarboxylic acids or dicarboxylic acids may also be used. Examples include α-β-unsaturated dicarboxylic acids and C 1-4 Half esters of alkanols, such as monomethyl fumarate; cyclic anhydrides of α-β-unsaturated dicarboxylic acids, such as maleic anhydride, itaconic anhydride and citraconic anhydride; and acrylic acid or methacrylic acid with C 1-30 Esters of alkanols, such as ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, dodecyl acrylate, hexadecyl acrylate and octadecyl acrylate.

[0086] Optionally, other ethylenically unsaturated monomers may be copolymerized into the carboxylic acid polymer backbone. Other examples of such ethylenically unsaturated monomers include styrene, vinyl acetate, ethylene, butadiene, acrylonitrile and mixtures thereof. The carboxylic acid polymer may preferably have a molecular weight of at least 1 million Daltons.

[0087] Suitable examples include C 1-4 Crosslinked copolymers of alkyl acrylates or methacrylates (e.g. ethyl acrylate) polymerized with one or more comonomers selected from acrylic acid, methacrylic acid and mixtures thereof. Such materials are generally referred to by the INCI name acrylate copolymers. Commercially available examples include Acrylates Copolymers from Rohm and Haas 33.

[0088] Also suitable is a C of acrylic acid or methacrylic acid. 10-30 Alkyl esters and one or more selected from acrylic acid, methacrylic acid and their corresponding C 1-4 Such materials are generally referred to under the INCI name Acrylates / C10-30 Alkyl Acrylate Crosspolymer. Commercially available examples include Acrylates / C10-30 Alkyl Acrylate Crosspolymer from Lubrizol Advanced Materials. Polymers 1342 and 1382.

[0089] Also suitable are optionally crosslinked copolymers of acrylic acid or methacrylic acid with alkyl acrylates and ethoxylated hydrophobically modified alkyl acrylates. Such materials may generally be referred to under the INCI names Acrylates / Steareth-20 Methacrylate Copolymer, Acrylates / Beheneth-25 Methacrylate Copolymer, Acrylates / Steareth-20 Methacrylate Crosspolymer, and Acrylates / Palmeth-25 Acrylate Copolymer. Commercially available examples include Acrylates / Steareth-20 Methacrylate Crosspolymer from Rohm & Haas. 22, 28 or 88 and from 3V Sigma

[0090] Preferably the carboxylic acid is a carbomer, such as a homopolymer of acrylic acid crosslinked with an allyl ether of pentaerythritol or an allyl ether of sucrose.

[0091] Mixtures of any of the above materials may also be used.

[0092] Preferably, hair care compositions of the present invention comprise from 0.1% to 3.0%, more preferably from 0.4% to 1.5% by weight of the composition of the carboxylic acid polymer.

[0093] In formulations containing anionic polymeric rheology modifiers (such as the above-mentioned carboxylic acid polymers), it is usually necessary to neutralize at least a portion of the free carboxyl groups by adding an inorganic or organic base. Examples of suitable inorganic or organic bases include alkali metal hydroxides (such as sodium hydroxide or potassium hydroxide), sodium carbonate, ammonium hydroxide, methylamine, diethylamine, trimethylamine, monoethanolamine, triethanolamine, and mixtures thereof.

[0094] The hair care compositions of the present invention may further comprise a nonionic polymeric rheology modifier selected from one or more nonionic cellulose ethers.

[0095] Suitable nonionic cellulose ethers for use as nonionic polymeric rheology modifiers in the present invention include (C 1-3 Alkyl) cellulose ethers, such as methyl cellulose and ethyl cellulose; hydroxy (C 1-3 alkyl) cellulose ethers, such as hydroxyethyl cellulose and hydroxypropyl cellulose; mixed hydroxy (C 1-3 alkyl) cellulose ethers, such as hydroxyethyl hydroxypropyl cellulose; and (C 1-3 Alkyl)hydroxyl (C 1-3 alkyl) cellulose ethers, such as hydroxyethyl methylcellulose and hydroxypropyl methylcellulose.

[0096] Preferred nonionic cellulose ethers for use as nonionic polymeric rheology modifiers in the present invention are water-soluble nonionic cellulose ethers, such as methylcellulose and hydroxypropylmethylcellulose. The term "water-soluble" in this context means that the solubility in water is at least 1 gram, more preferably at least 3 grams, and most preferably at least 5 grams in 100 grams of distilled water at 25°C and 1 atmosphere. This level indicates the production of macroscopically isotropic or transparent colored or colorless solutions.

[0097] Methylcellulose and hydroxypropyl methylcellulose are available from Dow Chemical as The HYDRADE(R) brand series is commercially available in a variety of viscosity grades.

[0098] Mixtures of any nonionic cellulose ethers may also be suitable. In typical compositions according to the invention, the level of nonionic cellulose ether is generally in the range of about 0.01 to about 2.0 wt %, preferably 0.1 to 0.5 wt %, more preferably 0.1 to 0.3 wt %, based on the total weight of the composition.

[0099] Preferably, the hair care compositions of the present invention comprise from 0.1 to 0.3% by weight of nonionic cellulose ether.

[0100] The hair care compositions of the present invention may contain further optional ingredients to enhance performance and / or consumer acceptance. Examples of such ingredients include fragrances, dyes and pigments, and preservatives. Each of these ingredients is present in an amount effective to achieve its purpose. Typically, these optional ingredients are individually included at a level of up to 5% by weight, based on the total weight of the composition.

[0101] Method for preparing hair care composition

[0102] The present invention also relates to a method for preparing a hair care composition, comprising the steps of:

[0103] (a) mixing the benzophenone or benzophenone derivative with the silicone compound to form a premix;

[0104] (b) mixing the premix of step (a) with other ingredients to form a hair care composition.

[0105] Benzophenone or benzophenone derivatives are one or more components selected from benzophenone, benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-6, benzophenone-7, benzophenone-8, benzophenone-10 and benzophenone-12, more preferably selected from benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-6, benzophenone-8, benzophenone-10 and benzophenone-12, more preferably selected from benzophenone-3, benzophenone-6, benzophenone-8 and benzophenone-10, further preferably selected from benzophenone-2, benzophenone-3 and benzophenone-8, and most preferably benzophenone-3.

[0106] It is preferred that the silicone compound is selected from dimethicone, dimethiconol or mixtures thereof.

[0107] Methods and uses

[0108] The present invention also provides a method for treating dandruff, comprising the step of applying the composition of the first aspect thereon. The method is non-therapeutic in nature. Preferably, it is for cosmetic purposes.

[0109] The present invention also provides the use of the composition of the first aspect for treating dandruff. The use is non-therapeutic in nature, preferably cosmetic in nature.

[0110] How to use

[0111] The hair care compositions of the present invention are primarily intended for topical application to the hair and scalp.

[0112] When the composition is a shampoo, it is applied topically to the hair and then massaged into the hair and scalp. It is then rinsed with water and the hair is dried. Hair oil or hair essence, which is a leave-in hair care composition, is left on for 1 to 10 hours after application and then washed off.

[0113] The invention will be further illustrated by the following non-limiting examples, in which all percentages cited are by weight based on total weight unless otherwise stated.

[0114] These examples are intended to illustrate the invention and are not intended to limit the invention to those examples per se.

[0115] Example

[0116] Example 1: Shampoo Set with or without Combination of Benzophenone or Benzophenone Derivative and Silicone Compound Sedimentation.

[0117] Preparation of hair care compositions

[0118] The following shampoo compositions were prepared as shown in Table-1:

[0119] In preparing Composition 1, benzophenone-3 and dimethicone are premixed and then mixed with the other ingredients to form the composition.

[0120] Table-1

[0121]

[0122] Vitro-skin (provided by IMS Inc) is used to simulate the human scalp. The skin is cut into appropriate sizes and fixed with plastic rings. 0.20g of the tested shampoo composition is added to the Vitro-skin, followed by 1.8ml of deionized water. The shampoo is stirred and rubbed onto the entire surface by stirring with a stirring rod for 30 seconds, and all the shampoo solution is removed using a dropper. The vitro-skin is then rinsed with 4ml of deionized water. Stir and rub the entire surface again for 30 seconds. Remove all the rinse water and repeat the rinse once more. After the vitro-skin is completely dry, the skin is placed in a centrifuge tube containing 10mL of methanol and then ultrasonically extracted for 30 minutes. 4mL of methanol is transferred to a new centrifuge tube and the methanol is completely evaporated by a vacuum concentrator. Reconstitute with 0.4mL of methanol, and transfer 0.2mL of the sample to a 2mL ultra-high performance liquid chromatography (LIPLC) brown vial with Micro-Inserts.

[0123] use ACQUITY ultra-high performance liquid chromatography (UPLC, Waters, Manchester, UK) was used for sample analysis. MassLynx software (version 4.1) was used for instrument control and data acquisition. Separation was performed on a Waters Acquity UPLC BEHC18 column (2.1 × 100 mm, 1.7 μm particle size). Mobile phase A consisted of 0.1% formic acid + 5 μM methylene phosphoric acid in DI water, while mobile phase B consisted of 0.1% formic acid in acetonitrile, programmed in gradient mode.

[0124] Deposition Test Method The samples were measured by a photodiode array (PDA) detector at an absorption wavelength of 302 nm.

[0125] Tested The results of the deposition are shown in Table-2 below:

[0126] Table-2

[0127]

[0128] The results show that Composition 1, which contains a combination of benzophenone-3 and dimethicone, provides significantly better deposition of piroctone olamine than Compositions A (without benzophenone-3 and dimethicone), B (without dimethicone), and C (without benzophenone-3).

[0129] Example 2: Effect of different benzophenone derivatives on Deposition Impact .

[0130] The following compositions as shown in Table 3 were prepared.

[0131] In preparing compositions D and 2, benzophenone-3 or benzophenone-4 was premixed with dimethicone and then mixed with the other ingredients to form the composition.

[0132] Table-3

[0133]

[0134] With UV exposure Shen Volume test

[0135] Following the protocol mentioned in Example 1, the in vitro-skin was treated with the shampoo composition.

[0136] UV treatment:

[0137] After the in vitro-skin was completely dry, 300 μL of 50% water / 50% methanol was added to the skin and then subjected to ultraviolet (UV) irradiation. UV irradiation was performed in an X-Rite (Macbeth) Spectra Light III chamber. The UV mode was selected for UV irradiation, which provides both UVA and UVB light. The UV light was tested by a UVX radiometer (UVX-36, E24195, UVP.), and the intensity was estimated to be 250 μw / cm for UVA. 2 , and for UVB it is estimated to be 110 μw / cm 2 The temperature of the chamber is equal to room temperature (20 ± 2 ° C). The sample is placed in the pipeline near the center of the chamber and exposed for 4 hours. The in vitro-skin is dried overnight and measured by UPLC Sedimentation.

[0138] The deposited

[0139] Tested The results of the deposition are shown in Table-4 below:

[0140] Table-4

[0141]

[0142] The data in Table 4 clearly show that the deposition of piroctone olamine under UV exposure was significantly improved when the composition according to the invention (Composition 2) was used during the experiment compared to the corresponding example outside the invention (Composition D, not containing the benzophenone or benzophenone derivative of the invention). The data further show that the combination of the benzophenone or benzophenone derivative of the invention with a silicone can improve the deposition and photostability of piroctone olamine.

[0143] Example 3: Effect of the dose of benzophenone derivatives under UV exposure Deposition Impact .

[0144] The following compositions as shown in Table-5 were prepared.

[0145] In preparing compositions D and 2, benzophenone-2 or benzophenone-3 was premixed with dimethicone and then mixed with the other ingredients to form the composition.

[0146] Table-5

[0147]

[0148]

[0149] The same method as that disclosed in Example 1 was used to test Sedimentation.

[0150] Tested The results of the deposition are shown in Table-6 below:

[0151] Table-6

[0152]

[0153] The results show that compositions 3-5 comprising a combination of benzophenone-3 or benzophenone-2 and dimethicone at a dosage of 0.2% or more provided significantly better piroctone olamine deposition than compositions E (containing no benzophenone derivatives and dimethicone), F (containing no benzophenone derivatives) and G (dosage of benzophenone derivatives less than 0.2%).

Claims

1. A hair care composition comprising: (i) a benzophenone derivative selected from benzophenone-2, benzophenone-3 and benzophenone-8; (ii) piroctone olamine; (iii) a siloxane compound; and (iv) a cosmetically acceptable carrier; The amount of the benzophenone derivative is 0.2 to 10 wt % of the total composition.

2. The hair care composition according to claim 1, wherein the amount of the benzophenone derivative is 0.3 to 5% by weight.

3. The hair care composition according to claim 1 or 2, wherein the amount of piroctone olamine is 0.01 to 10% by weight.

4. The hair care composition according to claim 1 or 2, wherein the amount of the silicone is 0.01 to 10% by weight.

5. The hair care composition according to claim 1, further comprising a surfactant.

6. The hair care composition according to claim 5, wherein the surfactant is an anionic surfactant or a cationic surfactant.

7. A hair care composition according to claim 6, wherein the anionic surfactant is an alkyl sulfate and / or alkoxylated alkyl sulfate surfactant.

8. A hair care composition according to claim 7, wherein the composition comprises a betaine surfactant.

9. A hair care composition according to any one of claims 5 to 8, wherein the composition is a shampoo.

10. The hair care composition according to claim 6, wherein the cationic surfactant is stearamidopropyldimethylamine, behenyltrimethylammonium chloride or stearyltrimethylammonium chloride.

11. The hair care composition of claim 10, wherein the composition is a hair conditioner.

12. A method for preparing a hair care composition according to any one of claims 1 to 11, comprising the steps of: (a) mixing the benzophenone derivative and the silicone compound to form a premix; (b) mixing the premix of step (a) with other ingredients to form the hair care composition.

13. Use of a composition as claimed in any one of claims 1 to 11 in the manufacture of a product for treating dandruff on the surface of the scalp.

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