Anti-dandruff compositions containing piroctone ethanolamine

Abstract

A hair care composition is disclosed comprising (i) an anionic surfactant; (ii) an amphoteric or zwitterionic surfactant; (iii) pyrrolidone ethanolamine; and (iv) polyaspartic acid or a derivative thereof represented by the structure of formula (1), wherein the sum of m+n is 2 to 10000, and R1 and R2 are independently selected from H, OH, and (O). m G and m are 0 or 1, G is independently selected from H and substituted or unsubstituted C1-C12 organic groups, M1 and M2 are independently selected from H, metal salts or ammonium salts, wherein non-limiting examples of metal salts include Na, K, Ca, Mg, and Al salts; and v) a cosmetically acceptable carrier; wherein the weight ratio of the polyaspartic acid or its derivative in the composition to the piroctone ethanolamine is at least 2:3. It has been shown to improve the stability of piroctone ethanolamine.

Description

Invention Field

[0001] This invention relates to hair care compositions. More specifically, this invention relates to hair care compositions comprising piroctone ethanolamine. Background of the Invention

[0003] Dandruff is a condition experienced by many people worldwide. Symptoms range from mild peeling to severe scalp inflammation and itching. Malassezia yeasts, such as Malassezia furfur, are considered by some to be a major cause of dandruff. While this may not represent the full scientific picture, Malassezia yeasts do appear to be closely associated with dandruff. Therefore, the common strategy for treating dandruff is to apply topical antifungal medications such as zinc pyrithione (ZnPTO), piroctone olamine, clomiprazole, and ketoconazole, which are typically delivered through shampoo.

[0004] Piroctone ethanolamine (also known as Piroctone ethanolamine is a compound commonly used to treat fungal infections. It is the ethanolamine salt of pyroctone olamine, an isohydroxamic acid derivative. Piroctone ethanolamine possesses antifungal properties, making it ideal for controlling the root cause of dandruff, a common fungus called Malassezia globosa. It is frequently used in anti-dandruff shampoos as an alternative to the commonly used compound zinc pyrithione. Typically, pyroctone ethanolamine is dissolved in a shampoo base composition that includes surfactants, water, siloxanes, polymers, and coloring and fragrance ingredients. When the user applies this composition to the hair and scalp, some of the pyroctone ethanolamine compound deposits on it.

[0005] Generally, the effectiveness of anti-dandruff shampoos or conditioners depends on the amount of anti-dandruff active ingredients deposited on the scalp and hair, as more deposits mean higher bioavailability.

[0006] However, the presence of metal salts reduces the efficacy of piroctone ethanolamine because deposited piroctone ethanolamine has lower bioavailability due to its tendency to react with metal salts. Metal salts are known to be introduced from raw materials and manufacturing processes, tap water during and after product application, and sweat in daily life. Therefore, there is a need to develop products that mitigate this phenomenon and provide higher efficacy. Summary of the Invention

[0007] The inventors have identified a novel way to improve the bioactivity of anti-dandruff agents such as piroctone olamine. We have determined that the stability of piroctone olamine can be improved by co-formulating it with polyaspartic acid or its derivatives and a specific surfactant system. Furthermore, the inventors believe that polyaspartic acid or its derivatives can enhance the bioactivity of piroctone olamine after it has been deposited on the scalp, because polyaspartic acid or its derivatives can be readily deposited on the scalp upon application.

[0008] According to a first aspect, a hair care composition is disclosed, comprising:

[0009] (i) Anionic surfactants;

[0010] (ii) Amphoteric or zwitterionic surfactants;

[0011] (iii) Piroctone ethanolamine;

[0012] (iv) Polyaspartic acid or its derivatives represented by the structure of Formula 1

[0013]

[0014] The sum of m+n ranges from 2 to 10000, and R1 and R2 are independently selected from H, OH, and (O). m G and m are 0 or 1, G is independently selected from H and substituted or unsubstituted C1-C12 organic groups, and M1 and M2 are independently selected from H, metal salts, or ammonium salts, wherein non-limiting examples of metal salts include Na, K, Ca, Mg, and Al salts; and

[0015] (v) A cosmetically acceptable carrier.

[0016] The weight ratio of the polyaspartic acid or its derivative to the pyrrolidone ethanolamine in the composition is at least 2:3.

[0017] According to a second aspect, a method for treating dandruff is disclosed, comprising the step of topically applying the composition of the first aspect to the desired scalp surface. Invention Details

[0019] To avoid doubt, any feature of one aspect of the invention may be used in any other aspect of the invention. The word “comprising” is intended to mean “including”, but not necessarily “consisting of” or “made up of”. In other words, the listed steps or options need not be exhaustive. Note that the examples given in the following description are intended to illustrate the invention and not to limit the invention to these examples alone. Similarly, unless otherwise stated, all percentages are weight / weight percentages. Unless explicitly indicated in the operational and comparative examples, or otherwise, all figures in this specification representing the amount of material or reaction conditions, physical properties of the material, and / or uses should be understood to be modified by the word “about”. Numerical ranges expressed in the format “from x to y” are understood to include both x and y. When multiple preferred ranges are described in the format “from x to y” for a particular feature, it should be understood that combinations of all ranges at different endpoints may also be considered. As used herein, the indefinite article “a” or “an” and its corresponding definite article “the” indicate at least one or more, unless otherwise stated. Where appropriate, the various features of the invention mentioned in the foregoing sections may be adapted to other sections with necessary modifications. 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 this disclosure in any way.

[0020] As used herein, "hair care composition" refers to a composition that is applied topically to the hair or scalp of mammals, particularly humans. Topically means applying the composition to an external surface of the body. In this invention, this is achieved by applying the composition to the hair or scalp. Such compositions are generally categorized as leave-in or wash-off and include any product intended to improve the appearance, cleanliness, odor control, or overall aesthetics of the scalp and hair. The hair care compositions of this invention may be in the form of liquids, lotions, creams, foams, scrubs, gels, shampoos, conditioners, shower gels, or strips. Preferably, the hair care compositions of this invention are leave-in compositions. Alternatively, the hair care compositions of this invention are wash-off compositions. Compositions that obtain the desired benefits through human ingestion are excluded from the scope of this invention.

[0021] Polyaspartic acid or its derivatives

[0022] The compositions according to the invention comprise polyaspartic acid or a derivative thereof represented by the structure of Formula 1:

[0023]

[0024] The sum of m+n ranges from 2 to 10000, and R1 and R2 are independently selected from H, OH, and (O). mG and m are 0 or 1, G is independently selected from H and substituted or unsubstituted C1-C12 organic groups, and M1 and M2 are independently selected from H, metal salts or ammonium salts, wherein non-limiting examples of metal salts include Na, K, Ca, Mg and Al salts.

[0025] Preferably, when m is 0, G is independently selected from substituted or unsubstituted C1-C9 organic groups, and when m is 1, G is independently selected from substituted or unsubstituted C1-C2 organic groups.

[0026] Preferably, polyaspartic acid or its derivatives can be represented by the structure of Formula 1, wherein the sum of m+n is 2 to 10000, R1 and R2 are independently selected from H and OH, and M1 and M2 are independently selected from H, metal salts or ammonium salts, wherein non-limiting examples of metal salts include Na, K, Ca, Mg and Al salts.

[0027] Preferably, polyaspartic acid or its derivatives can be represented by the structure of Formula 1, wherein the sum of m+n is 2 to 10000, R1 and R2 are H, and M1 and M2 are independently selected from H, metal salts or ammonium salts, wherein non-limiting examples of metal salts include Na, K, Ca, Mg, and Al salts.

[0028] More preferably, polyaspartic acid or its derivatives can be represented by the structure of Formula 1, where the sum of m+n is 10 to 50, R1 and R2 are H, and M1 and M2 are independently selected from H, metal salts or ammonium salts, wherein non-limiting examples of metal salts include Na, K, Ca, Mg, and Al salts.

[0029] Of particular preference is that the polyaspartic acid derivative is sodium polyaspartate.

[0030] The amount of polyaspartic acid or its derivatives in the compositions of the present invention depends on the amount of pyrrolidone ethanolamine used. Preferably, the composition contains 0.1 to 10% by weight of polyaspartic acid or its derivatives, more preferably 0.5 to 5% by weight, and even more preferably 1 to 2% by weight.

[0031] Not wanting to be bound by theory, the inventors believe that polymers or polymer derivatives capable of complexing with metal ions can improve the stability of piroctone ethanolamine during application of the composition, and can also improve the bioactivity of piroctone ethanolamine after deposition on the scalp, because polymers or polymer derivatives are more easily deposited on the scalp compared to other common metal chelating agents (e.g., EDTA, citric acid, etc.).

[0032] Surprisingly, the inventors have discovered that polyaspartic acid or its derivatives exhibit better performance in improving the stability of pyrrolidone ethanolamine compared to other polymers or polymer derivatives.

[0033] Furthermore, the inventors also believe that the bioactivity of piroctone ethanolamine can be enhanced after it is deposited on the scalp, because polyaspartic acid or its derivatives can be easily deposited on the scalp upon application.

[0034] Piroctone ethanolamine

[0035] Piroctone ethanolamine is the ethanolamine salt of pyroctone, an isohydroxamic acid derivative. Piroctone is a typical antimicrobial active substance. It is commonly known as pyroctone ethanolamine and is traded under the name...

[0036] The pyrrolidone ethanolamine 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, also known as 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)pyridone monoethanolamine salt. CAS number 68890-66-4, this compound has the following general formula:

[0037]

[0038] Some anti-dandruff hair care products contain piroctone olamine. It has been found that dissolved, intact piroctone olamine molecules are the only bioactive form of piroctone olamine. When hair care products containing piroctone olamine are used, the piroctone olamine dissociates and forms a complex with metal ions (e.g., iron ions) derived from tap water or sweat. The stability of the bioactive substance is affected by these metal ions, thus reducing its anti-dandruff efficacy.

[0039] The amount of piroctone ethanolamine in the compositions of the present invention will depend on the type of hair care composition and the exact nature of any other anti-dandruff agents used. Preferably, the composition contains 0.1 to 10% by weight of the piroctone ethanolamine, more preferably 0.5 to 5% by weight, and even more preferably 0.5 to 2% by weight.

[0040] The weight ratio of polyaspartic acid or its derivative to pyrrolidone ethanolamine in the composition is at least 2:3, preferably at least 1:1, and more preferably at least 2:1. Preferably, the weight ratio of polyaspartic acid or its derivative to pyrrolidone ethanolamine in the composition is from 2:3 to 85:1, preferably 1:1 to 85:1, more preferably 2:3 to 20:1, more preferably 1:1 to 10:1, further preferably 2:1 to 10:1, and most preferably 2:1 to 5:1.

[0041] surfactants

[0042] The compositions according to the present invention comprise anionic surfactants.

[0043] Non-limiting examples of suitable anionic cleaning surfactants are alkyl sulfates, alkyl ether sulfates, alkylaryl sulfonates, alkyl acyl hydroxyethyl sulfonates, alkyl succinates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, N-alkyl sarcosine salts, alkyl phosphates, alkyl ether phosphates, and alkyl ether carboxylic acids and their salts, particularly their sodium, magnesium, and ammonium salts, as well as mono-, di-, and triethanolamine salts. The alkyl and acyl groups typically contain 8 to 18, preferably 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 1 to 20 ethylene oxide or propylene oxide units per molecule. Typical anionic cleaning surfactants used in the compositions of the present 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, sodium triethanolamine dodecylbenzene sulfonate, sodium cocoyl hydroxyethyl sulfonate, sodium lauryl hydroxyethyl sulfonate, lauryl ether carboxylic acid, sodium N-lauryl sarcosinate, or mixtures thereof.

[0044] Preferred anionic surfactants are alkyl sulfates and alkyl ether sulfates. 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). Particularly preferred are alkyl ether sulfates. Preferred alkyl ether sulfates are those having the following 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 with an average value greater than at least 0.5, preferably between 1 and 3, more 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). Preferred alkyl ether sulfates are sodium lauryl ether sulfates with an average degree of ethoxylation of 0.5 to 3, preferably 1 to 3, more preferably 2 to 3.

[0045] These anionic surfactants are preferably present at a level of 2 to 16% by weight of the composition, more preferably 3 to 16%.

[0046] The compositions according to the invention comprise an amphoteric or zwitterionic surfactant. Suitable examples include alkylamine oxides, alkyl betaines, alkylamidopropyl betaines, alkyl sulfobetaine (sulfobetaine), alkyl amphoteric acetates, alkyl amphoteric propionates, and alkylamidopropyl hydroxysulfobetaine, wherein the alkyl group has 8 to 19 carbon atoms.

[0047] Preferably, the amphoteric surfactant is a betaine surfactant. More preferably, the betaine surfactant is one of alkylamidopropyl betaines. Cocamidopropyl betaine (CAPB) is particularly preferred.

[0048] In a preferred embodiment, the composition contains 0.1 to 10% by weight, preferably 0.5 to 8% by weight, more preferably 1 to 5% by weight of an amphoteric surfactant.

[0049] Hair care composition

[0050] According to another aspect of the invention, a hair care composition of the first aspect is disclosed. Preferably, the composition is a shampoo composition.

[0051] Preferably, the hair care composition of the present invention contains 1 to 50%, more preferably 2 to 40%, and more preferably 4 to 25% total surfactant.

[0052] Suitable, the shampoo composition contains 50 to 98%, preferably 60 to 92%, of water.

[0053] Preferably, the shampoo composition comprises one or more cationic polymers for conditioning hair.

[0054] Suitable cationic polymers include homopolymers with cationic substitution, or can be formed from two or more types of monomers. The weight-average molecular weight (M) of the polymer... w The molecular weight is typically between 100,000 and 3 million Daltons. The polymer will have 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 will be poor. If it is too high, there may be a problem with high tensile viscosity, resulting in stringiness of the composition when poured.

[0055] Cationic nitrogen-containing groups are typically present as substituents on a portion of the total monomer units of cationic polymers. Therefore, when the polymer is not a homopolymer, it can contain spaced non-cationic monomer units. Such polymers are described in the CTFA Cosmetic Ingredient Directory, Third Edition. The ratio of cationic to non-cationic monomer units is chosen to give the polymer a cationic charge density within a desired range, typically from 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 Tests for Nitrogen Determination in the United States Pharmacopeia.

[0056] Suitable cationic polymers include copolymers of vinyl monomers having cationic amine or quaternary ammonium functional groups with water-soluble spacer monomers such as (meth)acrylamide, alkyl and dialkyl (meth)acrylamide, alkyl (meth)acrylates, vinylcaprolactone, and vinylpyrrolidine. 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.

[0057] The cationic amine can be a primary, secondary, or tertiary amine, depending on the specific type of composition and the pH value. Generally, secondary and tertiary amines are preferred, especially tertiary amines.

[0058] Amine-substituted vinyl monomers and amines can be polymerized in the form of amines and then converted to ammonium via quaternization.

[0059] Cationic polymers may comprise monomer units derived from amine- and / or quaternary ammonium-substituted monomers and / or a mixture of compatible spacer monomers.

[0060] Suitable cationic polymers (non-limiting examples) include:

[0061] - Polymers containing cationic diallyl quaternary ammonium, including, for example, dimethyl diallyl ammonium chloride homopolymers and copolymers of acrylamide and dimethyl diallyl ammonium chloride, referred to in the industry (CTFA) as polyquaternary ammonium salt 6 and polyquaternary ammonium salt 7, respectively.

[0062] - Inorganic acid salts of homopolymers and copolymers of unsaturated carboxylic acids having 3 to 5 carbon atoms, including amino-alkyl esters (as described in U.S. Patent 4,009,256);

[0063] - Cationic polyacrylamide (as described in WO95 / 22311).

[0064] Other cationic polymers that can be used include cationic polysaccharide polymers, such as cationic cellulose derivatives, cationic starch derivatives, and cationic guar gum derivatives.

[0065] A particularly suitable type of cationic polysaccharide polymer is cationic guar gum derivatives, such as guar hydroxypropyltrimethylammonium chloride (available from Rhodia under the JAGUAR trademark series). Examples of such materials are JAGUAR C13S, JAGUAR C14, and JAGUAR C17.

[0066] A mixture of any of the above-mentioned cationic polymers can be used.

[0067] Preferably, the hair care composition of the present invention contains 0.01 to 5%, preferably 0.02 to 1%, more preferably 0.05 to 0.8% of a cationic polymer.

[0068] The hair care composition of the present invention may additionally comprise a cationic deposited polymer, which is a cationic galactomannan with an average molecular weight (M). w The concentration ranges from 1 million to 2.2 million g / mol, and the degree of cation substitution ranges from 0.13 to 0.3.

[0069] Galactomannan is a polysaccharide primarily composed of galactose and mannose units, and is commonly found in the endosperm of leguminous seeds, such as guar, locust bean, soapberry, flame tree, and other members of the leguminous family. Galactomannan consists of a backbone of 1→4-linked β-D-mannopyranosyl main chain units (also called mannoside units or residues) with repeating 1→6-linked α-D-galactose side groups (also called galactoside units or residues) branching from the 6th carbon atom of the mannnopyranose residues in the polymer backbone. Galactomannan from different leguminous species differs in the frequency of occurrence of galactoside side units branching from the polymannoside backbone. Mannosides and galactoside units are collectively referred to as glycoside units or residues herein. The average ratio of mannosides to galactoside units in galactomannan contained in guar gum (hereinafter referred to as "guar gum") is approximately 2:1.

[0070] Suitable cationic galactomannans include guar gum and hydroxyalkyl guar gum (e.g., hydroxyethyl guar gum or hydroxypropyl guar gum), which have been cationically modified by chemical reaction with one or more derivatizing agents.

[0071] In a typical composition, the amount of cationic galactomannan is generally from about 0.05 to 1% of the weight of the composition, preferably from 0.1 to 0.8%, and more preferably from 0.2 to 0.6%.

[0072] The hair care composition of the present invention may additionally contain anionic polymer rheology modifiers, such as carboxylic acid polymers.

[0073] In the context of this invention, the term "carboxylic acid polymer" generally refers to a homopolymer or copolymer obtained by polymerizing an olefinically unsaturated monomer containing a side-attached carboxylic acid group (hereinafter referred to as "carboxylic acid monomer").

[0074] Suitable carboxylic acid monomers typically have one or two carboxylic acid groups, a carbon-carbon double bond, and contain a total of 3 to about 10 carbon atoms, more preferably 3 to about 5 carbon atoms.

[0075] Specific examples of suitable carboxyl 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-mentioned α-β-unsaturated monocarboxylic or dicarboxylic acids can also be used. Examples include α-β-unsaturated dicarboxylic acids with 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.

[0076] Optionally, other olefinically unsaturated monomers can be copolymerized into a carboxylic acid polymer backbone. Examples of such other olefinically 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.

[0077] Suitable examples include those made of acrylic acid or methacrylic acid C. 1-4 Crosslinked copolymers formed by polymerizing alkyl esters (e.g., ethyl acrylate) with one or more comonomers selected from acrylic acid, methacrylic acid, and mixtures thereof. These materials are typically referred to as acrylate copolymers in the INCI nomenclature. Commercially available examples include those from Rohm and Haas. 33.

[0078] Also suitable is C from 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 Crosslinked copolymers formed by the polymerization of alkyl ester comonomers. These materials are typically referred to as acrylate / C in INCI nomenclature. 10-30 Alkyl acrylate crosspolymers. Commercially available examples include those from Lubrizol Advanced Materials. Polymers 1342 and 1382.

[0079] Copolymers of acrylic acid or methacrylic acid with alkyl acrylates and ethoxylated hydrophobically modified alkyl acrylates, optionally crosslinked, are also suitable. These materials are typically referred to in INCI nomenclature as acrylate / stearyl alcohol polyether-20 methacrylate copolymers, acrylate / behenol polyether-25 methacrylate copolymers, acrylate / stearyl alcohol polyether-20 methacrylate crosslinked polymers, and acrylate / palmethol polyether-25 acrylate copolymers. Commercially available examples include those from Rohm & Haas. 22, 28, or 88, and from 3V Sigma

[0080] Preferably, the carboxylic acid is carbomer, such as a homopolymer of acrylic acid crosslinked with allyl ether of pentaerythritol or allyl ether of sucrose.

[0081] A mixture of any of the above materials may also be used.

[0082] Preferably, the hair care composition of the present invention comprises 0.1 to 3.0%, more preferably 0.4 to 1.5% by weight of a carboxylic acid polymer.

[0083] In formulations containing anionic polymeric rheology modifiers (such as the carboxylic acid polymers described above), it is typically 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 (e.g., sodium hydroxide or potassium hydroxide), sodium carbonate, ammonium hydroxide, methylamine, diethylamine, trimethylamine, monoethanolamine, triethanolamine, and mixtures thereof.

[0084] The hair care composition of the present invention may further comprise a nonionic polymer rheology modifier selected from one or more nonionic cellulose ethers.

[0085] Suitable nonionic cellulose ethers used as nonionic polymer rheology modifiers in this invention include (C 1-3 Alkyl cellulose ethers, such as methylcellulose and ethylcellulose; hydroxyl (C 1-3 Alkyl cellulose ethers, such as hydroxyethyl cellulose and hydroxypropyl cellulose; mixed hydroxyl (C 1-3 Alkyl) cellulose ethers, such as hydroxyethyl hydroxypropyl cellulose; and (C 1-3 alkyl) hydroxy (C 1-3 Alkyl) cellulose ethers, such as hydroxyethyl methylcellulose and hydroxypropyl methylcellulose.

[0086] In this invention, the preferred nonionic cellulose ethers used as nonionic polymer rheology modifiers are water-soluble nonionic cellulose ethers, such as methylcellulose and hydroxypropyl methylcellulose. The term "water-soluble" as used herein means a solubility in water of 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.

[0087] Methylcellulose and hydroxypropyl methylcellulose are available from Dow Chemical. The trademark series was acquired in various viscosity grades.

[0088] Any mixture of nonionic cellulose ethers may also be suitable. In typical compositions according to the invention, the level of nonionic cellulose ether is typically in the range of about 0.01 to about 2.0% based on the total weight of the composition, and preferably in the range of 0.1 to 0.5%, more preferably from 0.1 to 0.3%.

[0089] Preferably, the hair care composition of the present invention comprises 0.1 to 0.3% by weight of nonionic cellulose ether.

[0090] Further preferably, the hair care composition of the present invention comprises cosmetic ingredients. Preferably, the cosmetic ingredients are selected from siloxanes, antibacterial agents other than anti-dandruff agents, foaming agents, fragrances, encapsulating agents (e.g., encapsulated aromatics), dyes, colorants, pigments, preservatives, thickeners, proteins, phosphate esters, buffers, pH adjusters, pearlescent agents (e.g., mica, titanium dioxide, titanium dioxide-coated mica, ethylene glycol distearate (INCI glycol distearate)) and / or sunscreens, viscosity modifiers, emollients, sunscreens, emulsifiers, sensory active substances (e.g., menthol and menthol derivatives), vitamins, mineral oils, essential oils, lipids, natural active substances, glycerin, natural hair nutrients such as plant extracts, fruit extracts, sugar derivatives and amino acids, microcrystalline cellulose and mixtures thereof.

[0091] Preferably, the hair care composition of the present invention comprises at least one cosmetic ingredient in 0.01 to 20% by weight of the total composition, more preferably 0.05 to 10% by weight, even more preferably 0.075 to 7.5% by weight, and most preferably 0.1 to 5% by weight of the total composition.

[0092] The hair care compositions of the present invention may also contain synergistic antimicrobial compounds that, when used in combination with piroctone olamine, provide synergistic antimicrobial benefits to enhance their performance and further inhibit the growth of Malassezia furfur. Non-limiting examples of such compounds include compounds having an alcohol group (e.g., magnolol, honokiol, or paeonol), piperazines, and phenolic compounds found in natural plant extracts, namely thymol and terpeniol.

[0093] The composition may additionally contain a vitamin B3 compound. A preferred vitamin B3 compound is nicotinamide.

[0094] Niacinamide is known to be used to secrete AMPs (antimicrobial proteins) from keratinocytes. These secreted AMPs enhance immunity, for example, in the scalp. Therefore, by using niacinamide, not only can anti-dandruff efficacy be enhanced through antifungal activity, but the scalp's own protective barrier against bacteria can also be strengthened. This combination can provide longer-lasting protection, for example, up to 24 hours of antibacterial protection.

[0095] When present, the hair care composition of the present invention preferably contains 0.1 to 5%, more preferably 0.5 to 5%, more preferably 0.5 to 3%, and most preferably 1.0 to 3.0% nicotinamide by weight of the composition.

[0096] Methods and uses

[0097] The present invention also provides a method for treating dandruff, comprising the step of topically applying the composition of the first aspect to a desired scalp surface. This method is inherently non-therapeutic. Preferably, it is for cosmetic purposes.

[0098] The present invention also provides the use of the composition of the first aspect for treating dandruff on a desired scalp surface. This use is inherently non-therapeutic, and preferably, inherently cosmetic.

[0099] How to use

[0100] The hair care composition of the present invention is primarily intended for topical application to hair and scalp.

[0101] When the composition is a shampoo, it is applied topically to the hair and then massaged into the hair and scalp. Rinse with water before drying the hair.

[0102] The present invention will be further illustrated by the following non-limiting embodiments, wherein, unless otherwise stated, all percentages cited are based on total weight by weight.

[0103] These embodiments are intended to illustrate the invention and are not intended to limit the invention to these embodiments alone. Example

[0104] Example 1: Shampoo composition in the presence of metal salts The stability of polyasparagus amino acids or their derivatives and The effect of weight ratio.

[0105] Preparation of hair care composition

[0106] Prepare the following shampoo compositions as shown in Table 1:

[0107] Table 1

[0108]

[0109] Stability test methods

[0110] A 0.1% FeCl3·6H2O solution was added to the above composition to simulate the presence of iron salts in tap water and sweat during and after product application. The aqueous solution was then diluted 20-fold with menthol in a 2 mL ultra-high performance liquid chromatography (UPLC) amber vial for measurement.

[0111] use Sample analysis was performed using ACQUITY ultra-high performance liquid chromatography (UPLC, Waters, Manchester, UK). 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 medronic acid in deionized water, and mobile phase B consisted of 0.1% formic acid + 5 μM medronic acid in acetonitrile, programmed in gradient mode. Samples were measured at an absorption wavelength of 302 nm using a photodiode array (PDA) detector.

[0112] The values ​​in Table 2 below represent the free free radicals in the composition. concentration:

[0113] Table 2

[0114]

[0115] The results show that, in the presence of metal salts, compositions 1 and 2 of the present invention provide significantly better pyrrolidone ethanolamine stability than compositions A (containing no polyaspartic acid or its derivatives) and composition B (polyaspartic acid or its derivatives in a weight ratio of less than 2:3 to pyrrolidone ethanolamine).

[0116] Example 2: The effect of surfactant system on metal salt in the presence of metal salt The impact on stability.

[0117] Prepare the following compositions as shown in Table 3.

[0118] Table 3

[0119]

[0120]

[0121] In the presence of metal salts stability

[0122] A 10% FeCl3·6H2O aqueous solution was prepared and added to the above-mentioned shampoo sample. The final concentration of FeCl3·6H2O was 0.1%, and the percentages of other active ingredients were unaffected. The above shampoo composition was colorless; however, it turned red immediately upon the addition of iron salts. The inventors discovered that when the FeCl3·6H2O aqueous solution was added to a solution containing... When added to a shampoo composition, it turns pale yellow. Therefore, it is speculated that the red color comes from... A complex formed with iron ions.

[0123] The color of the above composition after adding FeCl3·6H2O was measured using a Hunterlab UltraScan Pro (Hunter Associates Laboratory, Inc.). EasyMatchQC version 4.12 software was used for instrument control and data acquisition. The measurement mode was TTRAN-full transmission, and the color of deionized water was set as the background.

[0124] The values ​​in Table 4 below represent the intensity of the red color. A higher red intensity indicates that more of the composition reacts with the metal salt. and retain less free

[0125] Table 4

[0126] Composition C D 3 Intensity of red (au) 46.95±0.026 37.32±0.016 28.42±0.008

[0127] The data in Table 4 clearly demonstrate that, compared to corresponding embodiments other than those of the present invention (Composition C - without polyaspartic acid or its derivatives, Composition D - a combination without the surfactants of the present invention), when the composition according to the present invention (Composition 3) is used in the experiment, in the presence of a metal salt, Its stability has been improved.

[0128] Example 3: Compared with other chelating agents used as polymers or their derivatives, polytetrafluoroethylene (PTFE) exhibits superior performance in the presence of metal ions. aspartic acid or its derivatives The impact on stability.

[0129] Prepare the following compositions as shown in Table 5.

[0130] Table 5

[0131]

[0132] Stability test methods

[0133] A 0.01% FeCl3·6H2O solution was added to the above composition to simulate the presence of iron salts in sweat. The aqueous solution was then diluted 20-fold with menthol in a 2 mL ultra-high performance liquid chromatography (UPLC) vial for measurement.

[0134] The values ​​in Table 6 below are free Percentage (initial free) (Considered as 100%)

[0135] Table 6

[0136]

[0137] The results show that, in the presence of a metal salt, composition 4 of the present invention provides significantly better stability of pyrrolidone ethanolamine salt than composition EI (which does not contain polyaspartic acid or its derivatives).

Claims

1. A hair care composition comprising: (i) 0.1 to 20 wt% of an anionic surfactant, wherein the anionic surfactant is selected from an alkyl sulfate surfactant, an alkyl ether sulfate surfactant, or a mixture thereof; (ii) 0.1 to 10 wt% of an amphoteric surfactant, wherein the amphoteric surfactant is a betaine surfactant; (iii) 0.1 to 2 wt% of piroctone olamine; (iv) 0.1 to 10 wt% of a polyaspartic acid or a derivative thereof represented by the structure of Formula 1 Formula 1 wherein the sum of m+n is 10 to 50, R1, R2 is H, M1, M2 is independently selected from H, a metal salt, or an ammonium salt, wherein the metal salt is selected from Na, K, Ca, Mg, Al salt; and (v) a cosmetically acceptable carrier, wherein the weight ratio of the polyaspartic acid or a derivative thereof to the piroctone olamine in the composition is 1:1 to 85:

1.

2. The hair care composition of claim 1, wherein the polyaspartic acid derivative is polyaspartic acid sodium.

3. The hair care composition of claim 1 or 2, wherein the anionic surfactant is an alkyl ether sulfate surfactant, which is sodium lauryl ether sulfate.

4. The hair care composition of claim 1 or 2, wherein the betaine surfactant is one of an alkyl amidopropyl betaine.

5. The hair care composition of claim 1 or 2, wherein the betaine surfactant is cocamidopropyl betaine.

6. The hair care composition of claim 1 or 2, wherein the amount of the polyaspartic acid or a derivative thereof is 0.5 to 5 wt%.

7. The hair care composition of claim 1 or 2, wherein the amount of the polyaspartic acid or a derivative thereof is 1 to 2 wt%.

8. The hair care composition of claim 1 or 2, wherein the amount of the anionic surfactant is 2 to 16 wt%.

9. The hair care composition of claim 1 or 2, wherein the amount of the anionic surfactant is 3 to 16 wt%.

10. The hair care composition of claim 1 or 2, wherein the amount of the amphoteric surfactant is 0.5 to 8 wt%.

11. The hair care composition of claim 1 or 2, wherein the amount of the amphoteric surfactant is 1 to 5 wt%.

12. The hair care composition of claim 1 or 2, wherein the composition comprises a cationic polymer.

13. The hair care composition of claim 1 or 2, wherein the composition is a shampoo.

14. The hair care composition of claim 1 or 2, wherein the weight ratio of the polyaspartic acid or a derivative thereof to the piroctone olamine in the composition is 1:1 to 20:

1.

15. The hair care composition of claim 1 or 2, wherein the weight ratio of the polyaspartic acid or a derivative thereof to the piroctone olamine in the composition is 1:1 to 10:

1.

16. The hair care composition of claim 1 or 2, wherein the weight ratio of the polyaspartic acid or derivative thereof to the piroctone olamine in the composition is from 2: 1 to 10:

1.

17. The hair care composition of claim 1 or 2, wherein the weight ratio of the polyaspartic acid or derivative thereof to the piroctone olamine in the composition is from 2: 1 to 5:

1.

18. A non-therapeutic method of treating dandruff comprising the step of topically applying to the surface of the desired scalp the composition of any one of claims 1 to 17.

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