Hair care composition

Cationic polymers with defined charge densities improve piroctone compound deposition in hair care compositions, addressing the wash-off issue and enhancing anti-dandruff activity.

JP7757327B2Active Publication Date: 2025-10-21UNILEVER IP HLDG BV
View PDF 3 Cites 0 Cited by

Patent Information

Application Number
JP2022579800
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Priority Date
2020-06-25
Filing Date
2021-06-22
Publication Date
2025-10-21
Estimated Expiration
2041-06-22

AI Technical Summary

Technical Problem

Existing hair care compositions face challenges in effectively depositing piroctone compounds onto the scalp due to their wash-off nature when anionic surfactants are present, leading to poor anti-dandruff activity.

Method used

Incorporation of cationic polymers with defined charge densities, specifically acrylamidopropyltrimonium moieties, to enhance the deposition of piroctone compounds on the scalp.

Benefits of technology

Enhances the deposition of piroctone compounds, improving anti-dandruff efficacy by ensuring they remain on the scalp during rinsing.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure 0007757327000001
    Figure 0007757327000001
  • Figure 0007757327000002
    Figure 0007757327000002
  • Figure 0007757327000003
    Figure 0007757327000003
Patent Text Reader

Abstract

1. A hair care composition comprising: a) a piroctone compound; and 5b) a cationic homopolymer and / or copolymer comprising an acrylamidopropyltrimonium moiety, wherein the homopolymer and / or copolymer has a charge density of at least 3.5 meq / g.
Need to check novelty before this filing date? Find Prior Art

Description

[Technical Field]

[0001] The present invention relates to hair care compositions, and in particular to anti-dandruff shampoo compositions. [Background technology]

[0002] Hair care compositions generally provide cleansing or conditioning benefits, or a combination of the two. Such compositions typically include one or more cleansing surfactants, which generally aid in cleaning the hair and scalp free of unwanted dirt, particles, and grease.

[0003] Dandruff is a problem affecting many worldwide. The condition manifests itself when clumps of dead skin cells slough off the scalp. These are white and result in an aesthetically unpleasing appearance. The contributing factors to dandruff are certain members of the Malassezia yeast. To combat these, hair treatment compositions containing various actives for anti-dandruff effects have been developed. Piroctone compounds, such as piroctone olamine, are one such active.

[0004] A common problem with piroctone compounds is their difficulty in deposition onto the hair or scalp during the cleansing process. This is especially true when an effective anionic cleansing surfactant, such as sodium laureth sulfate, is present in the composition. During excessive rinsing, most of the piroctone is easily washed away along with the surfactant. Poor deposition correlates with poor anti-dandruff activity and therefore provides little relief from the adverse effects of dandruff. To date, attempts have been made to offset this drawback by increasing the amount of piroctone olamine in hair treatment compositions. However, this approach poses various problems, including increased cost, potential formulation instability, and potentially adverse effects on hair feel. Therefore, it is not a preferred approach in the industry.

[0005] Cationic polymers are used to enhance deposition of conditioning and / or antidandruff agents onto the hair and / or scalp. These polymers can be synthetic or natural polymers modified with cationic substituents. US Patent Application Publication No. 2019 / 000735 describes a hair care composition having a 2-pyridinol-N-oxide material and an iron chelating agent to provide antifungal benefits.

[0006] The present invention relates to the enhanced deposition of piroctone compounds (Octopirox) using cationic polymers with defined charge densities. Summary of the Invention [Means for solving the problem]

[0007] In a first aspect, the present invention provides a method for producing a medicament for the treatment of a pulmonary arthritis, comprising: a) a piroctone compound; b) homopolymers and / or copolymers containing acrylamidopropyltrimonium moieties, wherein the polymers and / or copolymers have a charge density of at least 3.5 meq / g at pH 7 and a weight average molecular weight (g / mol) of 100,000 to 500,000; The present invention relates to a hair care composition comprising:

[0008] In a second aspect, the present invention relates to a cosmetic method of depositing an anti-dandruff agent onto the scalp, the method being for a non-therapeutic benefit, comprising applying to the scalp surface of an individual a hair care composition according to any embodiment of the first aspect of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0009] The term "hair care composition" refers to a composition for topical application to mammalian, particularly human, hair and / or scalp. Such compositions can generally be classified as leave-on or rinse-off. The compositions of the present invention can be in the form of a liquid, lotion, cream, foam, scrub, gel, or bar. Non-limiting examples of such compositions include leave-on hair lotions, creams, and rinse-off shampoos, conditioners, shower gels, or toilet bars. The compositions of the present invention are preferably rinse-off compositions, particularly preferably shampoos or conditioners, and most preferably shampoos.

[0010] Cationic charge density refers to the number of cationic charges per unit weight of a given polymer. As used herein, the term "charge density" refers to the ratio of the positive charges on the 20 monomer units comprising a polymer to the molecular weight of said monomer units. The charge density multiplied by the polymer molecular weight determines the number of positively charged sites on a given polymer chain. Cationic charge density can be calculated from the degree of substitution as described in WO 2013 / 011122, the disclosure of which is incorporated herein by reference in its entirety, particularly page 8, lines 8-17.

[0011] The cationic charge density of the polymer may also be suitably determined under Chemical Tests for Nitrogen Determination by the Kjeldahl method as described in the United States Pharmacopoeia and is expressed in milliequivalents (meq) per gram.

[0012] The cationic charge density is measured at pH 7.

[0013] Water-insoluble means that the solubility of a material in water at 25° C. and atmospheric pressure is 0.1% by weight or less.

[0014] Molecular weight refers to the weight-average molecular weight of a given polymer. The weight-average molecular weight (WAVG MW) of a given polymer is determined by SEC (size exclusion chromatography) analysis using an absolute calibration (universal calibration). Polysaccharide standards pullulan and dextran were used for calibration.

[0015] Except in the examples, or where expressly indicated otherwise, all numbers herein expressing quantities of ingredients or reaction conditions, physical properties and / or uses of ingredients may be understood to be modified by the word "about."

[0016] All amounts are by weight of the final hair care composition unless otherwise specified.

[0017] It should be noted that in specifying any range of values, any particular upper limit value can be associated with any particular lower limit value.

[0018] Where features are disclosed with respect to a particular embodiment of the invention (e.g., a composition of the invention), such disclosure should be considered to apply mutatis mutandis to any other embodiment of the invention (e.g., a method of the invention).

[0019] Polymers suitable for use in the compositions of the present invention include acrylamidopropyltrimonium chloride. Preferably, the copolymer also includes acrylamide in addition to acrylamidopropyltrimonium chloride. A particularly preferred copolymer is a copolymer of acrylamidopropyltrimonium chloride and acrylamide.

[0020] The polymers and / or copolymers according to the present invention have a charge density at pH 7 of at least 3.5 meq / g, more preferably 4 meq / g or more, most preferably 4.3 to 5.3 meq / g.

[0021] The homopolymer and / or copolymer preferably has a weight average molecular weight of 100,000 to 500,000, more preferably 150,000 to 400,000.

[0022] An example of a suitable homopolymer is commercially available from Ashland under the tradename N-DurHance A-1000® (cationic homopolymer of acrylamidopropyltrimethylammonium chloride). An example of a suitable copolymer is commercially available from Ashland under the tradename N-DurHance AA2000® (cationic copolymer of acrylamidopropyltrimonium chloride / acrylamide copolymer).

[0023] Typically, the cationic polymer is present in an amount of from 0.01 to 5%, preferably from 0.05 to 2%, more preferably from 0.1 to 1% by weight of the total composition.

[0024] Additional cationic deposition polymers may be included in addition to the homopolymer / copolymer, but are not preferred.

[0025] A preferred form of the composition is an anti-dandruff shampoo, which may suitably contain 50 to 90%, preferably 60 to 80% by weight of water based on the total weight of the shampoo.

[0026] Cleansing Phase The cleansing phase comprises one or more cleansing surfactants, which act to cleanse the hair and / or scalp. The total amount of cleansing surfactant is preferably 3 to 45%, more preferably 5 to 25%, and most preferably 7 to 20% by weight of the total composition.

[0027] Preferably, the cleansing surfactant comprises an anionic surfactant, which comprises an ethoxylated alkyl sulfate anionic surfactant.

[0028] Preferred alkyl ether sulfates are of formula (I): RO-(CH2CH2-O) n -SO3 - M + (I) where R is a linear or branched alkyl chain having 8 to 18 (preferably 12 to 18) carbon atoms; n is the average degree of ethoxylation, ranging from 0.5 to 3 (preferably from 1 to 3); and M is a solubilizing cation such as sodium, potassium, ammonium, or substituted ammonium. One example is sodium lauryl ether sulfate (SLES). The most preferred example is SLES having an average degree of ethoxylation of 0.5 to 3, preferably 1 to 3.

[0029] The amount of such surfactant is preferably 2 to 20% by weight, more preferably 7 to 15% by weight, of the total composition.

[0030] Other surfactants, such as alkyl sulfates, may be present in the composition. Preferred alkyl sulfates are C 8-18 Alkyl sulfates, more preferably C 12-18 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).

[0031] The cleansing phase may contain one or more additional anionic surfactants that are cosmetically acceptable and suitable for topical application to hair and / or scalp. Examples of additional anionic surfactants include alkyl sulfonates, alkyl succinates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, N-alkyl sarcosinates, alkyl phosphates, alkyl ether phosphates, and alkyl ether carboxylic acids and their salts, particularly their sodium, magnesium, ammonium, and mono-, di-, and triethanolamine salts. The 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.

[0032] Typical anionic cleansing surfactants for use in shampoo compositions according to the invention include sodium oleyl succinate, ammonium lauryl sulfosuccinate, sodium lauryl ether sulfosuccinate, sodium dodecylbenzenesulfonate, triethanolamine dodecylbenzenesulfonate, lauryl ether carboxylic acid and sodium N-lauryl sarcosinate, sodium lauryl monoglyceride sulfate, sodium lauryl sulfate, sodium laureth sulfate, sodium cosyl sulfate, sodium cocoyl isethionate and mixtures thereof.

[0033] The composition may contain a co-surfactant to help impart aesthetic, physical, or cleansing properties to the composition. The co-surfactant is preferably included in the cleansing phase of the composition. Examples of co-surfactants include nonionic surfactants, which may be included in amounts ranging from 0.5 to 10%, preferably from 2 to 8%, and more preferably from 1 to 5% by weight of the total composition.

[0034] For example, representative nonionic surfactants that can be included in the treatment compositions, preferably shampoo compositions of the present invention, include aliphatic (C8-C 18 These include the condensation products of primary or secondary, straight- or branched-chain alcohols or phenols with alkylene oxides, usually ethylene oxide, generally containing 6 to 30 ethylene oxide groups. Other representative nonionic surfactants include mono- or di-alkylalkanolamides. Examples include coco mono- or di-ethanolamide and coco mono-isopropanolamide.

[0035] Further nonionic surfactants that can be included are alkyl polyglycosides (APGs). Typically, APGs comprise an alkyl group attached (possibly via a bridging group) to a block of one or more glycosyl groups. Preferred APGs are defined by the following formula (II): R ’ O-(G) k (II) In the formula, R’ is a branched or straight chain alkyl group which may be saturated or unsaturated, and G is a sugar group. ’ is about C5 to about C 20 Preferably, R' represents an average alkyl chain length of from about C to about C. 12 represents the average alkyl chain length. Most preferably, the value of R' is about 9.5 to about 10.5. G may be selected from a C5 or C6 monosaccharide residue, preferably a glucoside. G may be selected from the group consisting of glucose, xylose, lactose, fructose, mannose, and derivatives thereof. Preferably, G is glucose. The degree of polymerization k may have a value of about 1 to about 10 or more, preferably a value of k of about 1.1 to about 2, and most preferably a value of m of about 1.3 to about 1.5. Alkyl polyglycosides suitable for use in the present invention are commercially available, for example, materials identified as Seppic's Oramix NS10 and Henkel's Plantaren 1200 and Plantaren 2000.

[0036] Other sugar-derived nonionic surfactants that can be included in the compositions (preferably shampoos) of the present invention include C 10 -C 18 N-alkyl (C1-C6) polyhydroxy fatty acid amides, such as those described in WO 92 / 06154 and U.S. Pat. No. 5,194,639 12 -C 18 N-methylglucamides, as well as N-alkoxypolyhydroxyfatty acid amides, such as C 10 -C 18 N-(3-methoxypropyl)glucamide.

[0037] Preferred examples of co-surfactants are amphoteric or zwitterionic surfactants, which may be included in an amount ranging from 0.5 to about 10% by weight of the total composition, preferably from 2 to 8%, more preferably from 1 to 5% by weight.

[0038] Examples of amphoteric or zwitterionic surfactants include alkylamine oxides, alkylbetaines, alkylamidopropylbetaines, alkylsulfobetaines (sultaines), alkylglycinates, alkylcarboxyglycinates, alkylamphoacetates, alkylamphopropionates, alkylamphoglycinates, alkylamidopropylhydroxysultaines, acyltaurates, and acylglutamates, wherein the alkyl and acyl groups have from 8 to 22 carbon atoms. Exemplary amphoteric and zwitterionic surfactants for use in shampoos of the present invention include laurylamine oxide, cocodimethylsulfopropylbetaine, laurylbetaine, cocamidopropylbetaine, and sodium cocoamphoacetate.

[0039] Particularly preferred amphoteric or zwitterionic surfactants are the amidobetaine amphoteric surfactants of the general formula (III): [ka] In the formula, m is 2 or 3, and R 1 C(O) is selected from linear or branched, saturated or unsaturated acyl groups having 8 to 22 carbon atoms and mixtures thereof; R 2 and R 3 are each independently selected from alkyl, hydroxyalkyl, or carboxyalkyl groups having 1 to 6 carbon atoms and mixtures thereof. One example is cocamidopropyl betaine. The preferred amount of such surfactants is 0.5 to 10% by weight of the total composition, more preferably 2 to 8% by weight, and most preferably 1 to 5% by weight.

[0040] An optional but preferred additional surfactant is alkyl glycinate and / or alkyl carboxyglycinate, which, when present, is present in an amount of 1 to 8% by weight, preferably 2 to 6% by weight.

[0041] Preferably, the alkyl glycinate and / or alkyl carboxyglycinate is in the form of a salt with a solubilizing cation such as sodium, potassium, ammonium or substituted ammonium, C 8-22 The preferred glycinates are sodium cocoglycinate and sodium cocoyl glycinate.

[0042] Mixtures of any of the aforementioned amphoteric or zwitterionic surfactants may also be suitable. A preferred mixture is a mixture of cocamidopropyl betaine with the aforementioned additional amphoteric or zwitterionic surfactant. A preferred additional amphoteric or zwitterionic surfactant is sodium cocoamphoacetate.

[0043] In a preferred embodiment, the cleansing phase comprises an alkyl sulfate and / or ethoxylated alkyl sulfate anionic surfactant and a betaine surfactant, preferably alkylamidopropyl betaine.

[0044] The total amount of surfactant (including co-surfactant) in the hair treatment composition is generally from 1 to 50% by weight of the total composition, preferably from 2 to 40% by weight, more preferably from 10 to 25% by weight.

[0045] Piroctone compounds Piroctone compounds for use in the present invention may include piroctonic acid, primary, secondary and tertiary olamine salts of piroctonic acid (such as the diethanolamine and triethanolamine salts), and mixtures thereof, preferably piroctonic acid, primary olamine salts of piroctonic acid (i.e., piroctone olamine, also known as Octirox®), and mixtures thereof.

[0046] Piroctone compounds useful in the present invention typically comprise a structure defined by formula (IV): [ka] wherein R4 is selected from a C1-C17 hydrocarbon group, R5 is selected from C1-4 alkyl, C2-4 alkenyl or alkynyl, hydrogen, phenyl, or benzyl, and M1 is selected from hydrogen, monoethanolamine (MEA), diethanolamine (DEA), or triethanolamine (TEA). A preferred R4 group is (CH3)3CCH2CH(CH3)CH2-, and R5 is preferably methyl. More preferably, R4 is (CH3)3CCH2CH(CH3)CH2-, R5 is methyl, and M1 is hydrogen or MEA. Most preferably, R4 is (CH3)3CCH2CH(CH3)CH2-, R5 is methyl, and M1 is hydrogen.

[0047] Piroctone olamine is particularly preferred.

[0048] Typical amounts of piroctone compound are 0.01 to 5% by weight of the total composition, preferably 0.05 to 2% by weight, more preferably 0.1 to 1.5% by weight.

[0049] Preferably, the weight ratio of homopolymer / copolymer to piroctone compound is preferably 2:1 or more preferably 1.5:1 or less, and most preferably in the form of 0.3:1 to 1.1:1.

[0050] Preferably, the piroctone compound forms at least 50% by weight of the total amount of anti-dandruff agents in the composition, more preferably at least 70% by weight.

[0051] Oil-in-water emulsion The composition according to the invention may comprise an oil-in-water emulsion.

[0052] The aqueous phase of the emulsion comprises water. Suitably the emulsion comprises 25 to 85%, preferably 40 to 70%, more preferably 45 to 60% water by weight of the total emulsion.

[0053] The silicone is present in an oil-in-water emulsion and is a conditioning agent intended to be deposited on the remaining hair after rinsing the hair with water.

[0054] Silicone in water-in-oil emulsion (D 3,2 ) The particle size of the droplets is preferably 10 nm to 10 microns, more preferably 50 nm to 5 microns, and most preferably 100 nm to 5 microns. 3,2 The mean droplet diameter is D 3,2 The average droplet size can be measured by laser light scattering techniques, for example using a 2600D Particle Sizer from Malvern Instruments.

[0055] Typical amounts of silicones are from 0.1 to 5%, preferably from 0.3 to 3%, more preferably from 0.5 to 2.5% by weight of the total composition.

[0056] Typical silicones may include polyalkyl siloxanes, polyaryl siloxanes, polyalkylaryl siloxanes, polyether siloxane copolymers, and mixtures thereof.

[0057] Silicone can include functionalized silicone.Suitable functionalized silicones include, for example, hydroxyl-, amino-, carboxy-, betaine-, quaternary ammonium-, carbohydrate-, hydroxy- and alkoxy-substituted silicones.Functionalized silicones can also include multiple substitutions.Preferably, functionalized silicones are aminosilicones, especially when priloctone compounds are solubilized in silicones.

[0058] Aminosilicones are described in EP 455185 and include trimethylsilylamodimethicone, shown below, which is sufficiently water-insoluble to be useful in emulsions. Si(CH3)3-O-[Si(CH3)2-O-]x-[Si(CH3)(R6-NH-CH2CH2-NH2)-O-]y-Si(CH3)3 where x + y is a number between about 50 and about 500, the weight percent of amine functional groups is between about 0.03% and about 8%, and R6 is an alkylene group having 2 to 5 carbon atoms. Preferably, the number x + y is between 100 and 300, and the weight percent of amine functional groups is between about 0.5% and 4%. As expressed herein, weight percent amine functional groups is measured by titrating a sample of the aminosilicone against alcoholic hydrochloric acid to a bromocresol green endpoint. The weight percent amine is calculated using a molecular weight of 45 (corresponding to CH3-CH2-NH2).

[0059] Other cationic polymers include polygalactomannans and polysaccharide polymers such as cationic cellulose derivatives and cationic starch derivatives.

[0060] suspending agent A suspending agent is a preferred feature of the composition. Suitable suspending agents are selected from polyacrylic acid, crosslinked polymers of acrylic acid, copolymers of acrylic acid and hydrophobic monomers, copolymers of carboxylic acid-containing monomers and acrylic acid esters, crosslinked copolymers of acrylic acid and acrylate esters, heteropolysaccharide gums, and crystalline long-chain acyl derivatives. The long-chain acyl derivative is preferably selected from ethylene glycol stearate, alkanolamides of fatty acids having 16 to 22 carbon atoms, and mixtures thereof. Ethylene glycol distearate and polyethylene glycol 3 distearate are preferred long-chain acyl derivatives because they impart a pearlescent appearance to the composition. Polyacrylic acid is commercially available as Carbopol 420, Carbopol 488, or Carbopol 493. Polymers of acrylic acid crosslinked with polyfunctional agents may also be used. These are commercially available as Carbopol 910, Carbopol 934, Carbopol 941, and Carbopol 980. An example of a suitable copolymer of a carboxylic acid-containing monomer and an acrylic acid ester is Carbopol 1342. All Carbopol™ materials are available from Goodrich. A suitable crosslinked polymer of acrylic acid and an acrylate ester is Pemulen TR1 or Pemulen TR2. A suitable heteropolysaccharide gum is xanthan gum, such as that available as Kelzan mu.

[0061] Mixtures of any of the above suspending agents may be used. Mixtures of crosslinked polymers of acrylic acid and crystalline long chain acyl derivatives are preferred.

[0062] The most preferred example is a cross-linked polyacrylate polymer.

[0063] When included, suspending agents are generally present in shampoo compositions of the present invention in an amount of from 0.01 to 5% by weight, preferably from 0.1 to 2.5% by weight, more preferably from 0.25 to 1% by weight.

[0064] The viscosity of the composition, as measured at 30°C using a Brookfield V2 viscometer (spindle RTV5, 1 minute, 20 rpm), is suitably in the range of 3,000 to 10,000 mPa·s, preferably 4,000 to 8,000 mPa·s, and more preferably 5,000 to 7,000 mPa·s.

[0065] The pH of the composition of the present invention is preferably in the range of 3 to 9, more preferably 4 to 7, and even more preferably 4.5 to 6.5.

[0066] Other optional ingredients The composition may optionally contain one or more ingredients for use in hair treatment products, provided that the optional ingredients are physically and chemically compatible with the essential ingredients described hereinabove and do not otherwise unduly impair the feel, rheology, and conditioning performance of the formulation. The individual concentrations of such optional ingredients may range from 0.001% to 10%, preferably 0.01% to 5%, by weight of the total composition. Such ingredients may include fragrances, dyes and pigments, pH adjusters, pearlescent or opacifying agents, viscosity modifiers, preservatives, and natural hair nutrients such as botanical and fruit extracts, sugar derivatives, and amino acids. The composition may also contain additional silicones not present in the oil-in-water emulsion phase. The additional silicones may be the same as or different from the silicones present in the emulsion phase. The composition may also contain additional antidandruff and / or antibacterial agents, such as pyridinethione salts, pine tar, sulfur, salicylic acid, azoles, selenium sulfide, or mixtures thereof.

[0067] How to use The composition is used in a method for treating a surface. An effective amount of the composition is applied to the desired surface, preferably selected from hair and / or scalp, wetted with water. The composition is allowed to remain on the surface for a given time, preferably in combination with massage, to exert its effect before being rinsed off with water. The given time is preferably 20 seconds to 2 minutes, more preferably 30 seconds to 1 minute. The effective amount is typically in the range of 1 g to 20 g, preferably 2.5 g to 10 g.

[0068] The compositions of the present invention are primarily intended for topical application to at least a portion of an individual's scalp and / or hair, either as rinse-off or leave-on compositions, preferably as rinse-off compositions such as shampoos.

[0069] The following examples are provided to facilitate understanding of the present invention and are not intended to limit the scope of the claims. Examples in accordance with the present invention are designated by numbers, and comparative examples are designated by letters.

[0070] [Example] The following examples were prepared:

[0071] [Table 1]

[0072] 0.1 g of the example composition / g hair was applied evenly onto the hair switch. The hair switch was washed twice. After washing, the hair switch was placed in a drying cabinet (50°C) until dry. After drying, the hair switch was transferred to a bottle containing 10 ml of ethanol. The bottle was sealed and placed on a bottle roller for a known period of time. A sample of appropriate size for analysis was removed from the bottle using a syringe and filtered through a syringe filter into a vial for analysis using HPLC-UV methodology against a set of known standards containing known amounts of Octopirox (µg / ml) in ethanol.

[0073] [Table 2]

[0074] The inventive examples deposit octopirox into hair more effectively than the comparative examples.

Claims

1. a) Piroctonic acid, primary, secondary and tertiary olamine salts of piroctonic acid, and a compound represented by the following formula (IV): 【Chemical 1】 (In the formula, R 4 is C 1 -C 17 R is selected from hydrocarbon groups; 5 is C1-4 alkyl, C 2-4 selected from alkenyl or alkynyl, hydrogen, phenyl or benzyl; M 1 is selected from hydrogen, monoethanolamine (MEA), diethanolamine (DEA) or triethanolamine (TEA). a piroctone compound selected from the group of compounds comprising compounds comprising a structure defined by b) cationic homopolymers and / or copolymers comprising acrylamidopropyltrimonium moieties, said homopolymers and / or copolymers having a charge density of at least 3.5 meq / g at pH 7 and a weight average molecular weight (g / mol) of 100,000 to 500,000; A hair care composition comprising: The hair care composition further comprises an anionic surfactant.

2. 10. The hair care composition of claim 1, wherein the weight ratio of homopolymer / copolymer to piroctone compound is 2:1 or less.

3. 3. The hair care composition of claim 1, wherein the piroctone compound is piroctone olamine.

4. 4. A hair care composition according to any one of claims 1 to 3, wherein the copolymer is an acrylamidopropyltrimonium chloride / acrylamide copolymer.

5. 5. The hair care composition of claim 4, wherein the weight ratio of acrylamidopropyltrimonium chloride to acrylamide in said copolymer is greater than 2:

1.

6. 6. A hair care composition according to any one of claims 1 to 5, wherein the amount of the cationic polymer is from 0.001 to 2% by weight of the total composition.

7. The hair care composition of claim 1 , wherein the composition is a shampoo.

8. 8. A hair care composition according to any one of claims 1 to 7, wherein the piroctone compound is present in an amount of 0.01 to 5% by weight of the total composition.

9. A hair care composition according to any preceding claim, wherein the cationic polymer is present in an amount of from 0.01 to 5% by weight of the total composition.

10. 10. The hair care composition of claim 1, further comprising a silicone emulsion.

11. 11. The hair care composition of claim 1, wherein the piroctone compound is piroctone olamine.

Citation Information

Patent Citations

  • Compositions containing cationic polymers and water-insoluble solid substances

    JP2005511583A

  • Personal Cleansing Composition

    JP2019519551A

  • Compositions having enhanced deposition of surfactant soluble antidandruff agents

    US20190328647A1