WO2015200284A1 - Procédé de préparation d'une composition de conditionnement pour les cheveux comprenant un surfactant cationique à base de mono-alkyl amine et un polymère anionique - Google Patents

Procédé de préparation d'une composition de conditionnement pour les cheveux comprenant un surfactant cationique à base de mono-alkyl amine et un polymère anionique Download PDF

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WO2015200284A1
WO2015200284A1 PCT/US2015/037119 US2015037119W WO2015200284A1 WO 2015200284 A1 WO2015200284 A1 WO 2015200284A1 US 2015037119 W US2015037119 W US 2015037119W WO 2015200284 A1 WO2015200284 A1 WO 2015200284A1
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group
melting point
cationic surfactant
alkyl
anionic polymer
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PCT/US2015/037119
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English (en)
Inventor
Huixian GAO
Nobuaki Uehara
TianYong LIM
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The Procter & Gamble Company
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Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to MX2016016935A priority Critical patent/MX2016016935A/es
Priority to CN201580034612.5A priority patent/CN106456503A/zh
Priority to EP15736721.0A priority patent/EP3160432A1/fr
Priority to JP2016573824A priority patent/JP2017518337A/ja
Publication of WO2015200284A1 publication Critical patent/WO2015200284A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5424—Polymers characterized by specific structures/properties characterized by the charge anionic

Definitions

  • the present invention relates to a method of preparing a hair conditioning composition, wherein the composition comprising: a mono-alkyl amine cationic surfactant; a high melting point fatty compound; an anionic polymer comprising higher % of a vinyl monomer (A) with a carboxyl group; and an aqueous carrier, wherein the method comprises a step: mixing the cationic surfactant, high melting point fatty compound, anionic polymer and aqueous carrier to form an emulsion.
  • the method of the present invention provides hair conditioning compositions having reduced chunks while containing both mono-alkyl amine cationic surfactants and anionic polymers containing higher % of vinyl monomer with carboxyl group.
  • conditioning agents such as cationic surfactants, high melting point fatty compounds, silicone compounds, and mixtures thereof.
  • Most of these conditioning agents are known to provide various conditioning benefits.
  • rinse-off conditioners containing such conditioning agents it's relatively difficult for many of such agents to remain on the hair after rinsing.
  • conditioners There have been trials for conditioners to provide improved conditioning benefits, especially in rinse-off conditioners.
  • Japanese Patent Application Laid-Open No. 2012-106985 discloses hair cosmetics comprising a cationic surfactant, a fatty alcohol, a silicone, and a polymer containing a vinyl monomer with carboxyl group, wherein the polymer is said to provide superior deposition of cationic surfactants, superior viscosity to the composition, and superior smoothness during the application of the composition.
  • compositions comprise mono-alkylamine cationic surfactants and anionic polymers containing higher % of vinyl monomer with carboxyl group, the composition form visible larger size of chunks which are not desirable at least from the product appearance stand point.
  • the present invention is directed to a method of preparing a hair conditioning composition, wherein the composition comprising by weight:
  • an anionic polymer comprising a vinyl monomer (A) with a carboxyl group, wherein the vinyl monomer (A) is contained in the polymer at a level of from about 40 mass% to about 100mass% based on the total mass of the anionic polymer; and (d) an aqueous carrier;
  • the method of the present invention provides hair conditioning compositions having reduced chunks, especially reduced larger particle size of chunks, while containing both mono- alkyl amine cationic surfactants and anionic polymers containing higher % of vinyl monomer with carboxyl group.
  • FIG. 1 is a photo of a microscope image of the composition of Ex. 1
  • FIG. 2 is a photo of a microscope image of the composition of Ex.2
  • FIG. 3 is a photo of a microscope image of the composition of Ex. 3
  • FIG. 4 is a photo of an image of the composition of CEx. i DETAILED DESCRIPTION OF THE INVENTION
  • mixtures is meant to include a simple combination of materials and any compounds that may result from their combination.
  • the present invention comprises a step of mixing the cationic surfactant system, high melting point fatty compound, anionic polymer and aqueous carrier to form an emulsion.
  • the inventors of the present invention have surprisingly found that, the pre-addition of the anionic polymer prior to emulsion formation provides the composition having reduced chunk, compared to post-addition of the anionic polymer after emulsion formation.
  • the anionic polymer and aqueous carrier are mixed before mixing them with the cationic surfactant and/or high melting point fatty compound.
  • the polyols are contained in the composition, it is preferred that the polyols are also mixed to form an emulsion in view of the benefit of the present invention, more preferably, mixed with the anionic polymer and aqueous carrier before mixing them with the cationic surfactant and/or high melting point fatty compound.
  • the emulsion can be prepared by any conventional method well known in the art. They can be prepared by the following preferred methods, namely, E-METHOD A and E-METHOD B.
  • a preferred method of forming an emulsion comprises the steps of:
  • the mixture is cooled down to form an emulsion.
  • the temperature of the mixture is above the melting point of the high melting point fatty compounds, preferably above the melting point of the high melting point fatty compounds, cationic surfactant system, and mixtures thereof.
  • the mixture has a temperature of from about 40°C, more preferably from about 50°C, still more preferably from about 60°C, even more preferably from about 70°C, further preferably from about 75°C, and to about 150°C, more preferably to about 100°C, still more preferably to about 90°C.
  • the cationic surfactant, high melting point fatty compounds can be added to the aqueous carrier at anytime at any temperature, as long as they are mixed at the above temperature.
  • the cationic surfactant, high melting point fatty compounds can be added to the aqueous carrier at a lower temperature than the above temperature, then heated up to the above temperature, and mixed at the above temperature.
  • warmed and melted cationic surfactants and/or high melting point fatty compounds can be added to warmed water, and mixed without further heating up.
  • the mixture is cooled down to form an emulsion, preferably gel matrix.
  • the mixture is gradually cooled down, at a rate of from about 1°C to 10°C /minute, more preferably from about 1°C to 5°C/minute.
  • Another preferred method of forming an emulsion comprises the steps of:
  • (1-B2) preparing an aqueous phase comprising the anionic polymer and aqueous carrier, and optionally polyol, wherein the temperature of the aqueous phase is below the melting point of the high melting point fatty compounds, preferably the aqueous phase further comprising an aqueous carrier;
  • mixing step (1-B3) comprises the following detailed steps:
  • compositions of the present invention comprise a cationic surfactant.
  • the cationic surfactant is included in the composition at a level of from about 0.1% to about 8%, preferably from about 0.2% to about 6%, more preferably from about 0.5% to about 5% by weight of the composition.
  • the cationic surfactant is included such that the mole % of the cationic surfactant to a sum of the cationic surfactant and the high melting point fatty compound is from about 5% to about 60%, preferably from about 8% to about 40%, more preferably from about 10% to about 35%. If the mole% is too low, the composition provides increased wet friction and/or reduced wet clean feel. If the mole% is too high, the composition may provide an inferior product texture.
  • Cationic surfactants useful herein are mono-alkyl amine cationic surfactant having one long alkyl chain of from 12 to 30 carbon atoms including mono-alkyl amidoamine cationic surfactant. Additionally, di-alkyl quaternized ammonium salt cationic surfactant having two long alkyl chain of from 12 to 30 carbon atoms may be used together with the above mono-alkyl cationic surfactants, in view of providing improved clean feel on wet hair.
  • compositions of the present invention comprise a mono-alkyl amine cationic surfactant.
  • the mono-alkyl amine cationic surfactant can be included in the composition at a level of from about 0.1% to about 8%, preferably from about 0.2% to about 6%, more preferably from about 0.5% to about 5% by weight of the composition.
  • Mono-alkyl amine cationic surfactants useful herein are primary, secondary, and tertiary amines having one long alkyl or alkenyl group of from about 12 to about 30 carbon atoms, preferably from 16 to 24 carbon atoms, more preferably from 18 to 22 alkyl group.
  • Mono-alkyl amines useful herein also include mono-alkyl amidoamines.
  • tertiary amidoamines having an alkyl group of from about 12 to about 22 carbon atoms, preferably from about 16 to about 22 carbon atoms.
  • exemplary tertiary amido amines include: stearamidopropyldimethylamine, stearamidopropyldiethylamine, stearamidoethyldiethylamine, stearamidoethyldimethylamine, palmitamidopropyldimethylamine, palmitamidopropyldiethylamine, palmitamidoethyldiethylamine, palmitamidoethyldimethylamine, behenamidopropyldimethylamine, behenamidopropyldiethylamine, behenamidoethyldiethylamine, behenamidoethyldimethylamine, arachidamidopropyldimethylamine, arachidamidopropyldiethylamine,
  • the above mono-alkyl amine cationic surfactants are preferably used in combination with acids such as ⁇ -glutamic acid, lactic acid, hydrochloric acid, malic acid, succinic acid, acetic acid, fumaric acid, tartaric acid, citric acid, ⁇ -glutamic hydrochloride, maleic acid, and mixtures thereof; more preferably ⁇ -glutamic acid, lactic acid, citric acid.
  • the acid can be used at a molar ratio of the amine to the acid of from about 1 : 0.3 to about 1 : 2, more preferably from about 1 : 0.4 to about 1 : 1.
  • the composition of the present invention may contain a di-alkyl quaternized ammonium salt cationic surfactant.
  • the di-alkyl quaternized ammonium salt cationic surfactant can be included in the composition at a level of from about 0.05% to about 5%, preferably from about 0.1% to about 4%, more preferably from about 0.2% to about 3% by weight of the composition.
  • the weight ratio of the mono-alkyl cationic surfactant to the di-alkyl quaternized ammonium salt cationic surfactant is from about 1:1 to about 5:1, more preferably from about 1.2:1 to about 5:1, still more preferably from about 1.5:1 to about 4:1, in view of stability in rheology and conditioning benefits.
  • Di-alkyl quaternized ammonium salt cationic surfactants useful herein are those having two long alkyl chains of from 12 to 30 carbon atoms, more preferably from 16 to 24 carbon atoms, still more preferably from 18 to 22 carbon atoms.
  • Such di-alkyl quaternized ammonium salts useful herein are those having the formula (I):
  • R 71 , R 72 , R 73 and R 74 are selected from an aliphatic group of from 12 to 30 carbon atoms, preferably from 16 to 24 carbon atoms, more preferably from 18 to 22 carbon atoms or an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl group having up to about 30 carbon atoms; the remainder of R 71 , R 72 , R 73 and R 74 are independently selected from an aliphatic group of from 1 to about 8 carbon atoms, preferably from 1 to 3 carbon atoms or an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl group having up to about 8 carbon atoms; and X " is a salt-forming anion selected from the group consisting of halides such as chloride and bromide, C1-C4 alkyl sulfate such as methosulfate and
  • the aliphatic groups can contain, in addition to carbon and hydrogen atoms, ether linkages, and other groups such as amino groups.
  • the longer chain aliphatic groups e.g., those of about 16 carbons, or higher, can be saturated or unsaturated.
  • two of R 71 , R 72 , R 73 and R 74 are selected from an alkyl group of from 12 to 30 carbon atoms, preferably from 16 to 24 carbon atoms, more preferably from 18 to 22 carbon atoms; and the remainder of R 71 , R 72 , R 73 and R 74 are independently selected from CH 3 , C2H5, C2H4OH, CH2C6H5, and mixtures thereof.
  • Such preferred di-alkyl cationic surfactants include, for example, dialkyl (14-18) dimethyl ammonium chloride, ditallow alkyl dimethyl ammonium chloride, dihydrogenated tallow alkyl dimethyl ammonium chloride, distearyl dimethyl ammonium chloride, and dicetyl dimethyl ammonium chloride.
  • the composition of the present invention comprises a high melting point fatty compound.
  • the high melting point fatty compound is included in the composition at a level of from about 1% to about 15%, preferably from about 1.5% to about 12%, more preferably from about 2% to about 10% by weight of the composition.
  • the high melting point fatty compound useful herein have a melting point of 25 °C or higher, preferably 40°C or higher, more preferably 45 °C or higher, still more preferably 50°C or higher, in view of stability of the emulsion especially the gel matrix.
  • such melting point is up to about 90°C, more preferably up to about 80°C, still more preferably up to about 70°C, even more preferably up to about 65°C, in view of easier manufacturing and easier emulsification.
  • the high melting point fatty compound can be used as a single compound or as a blend or mixture of at least two high melting point fatty compounds. When used as such blend or mixture, the above melting point means the melting point of the blend or mixture.
  • the high melting point fatty compound useful herein is selected from the group consisting of fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, and mixtures thereof. It is understood by the artisan that the compounds disclosed in this section of the specification can in some instances fall into more than one classification, e.g., some fatty alcohol derivatives can also be classified as fatty acid derivatives. However, a given classification is not intended to be a limitation on that particular compound, but is done so for convenience of classification and nomenclature. Further, it is understood by the artisan that, depending on the number and position of double bonds, and length and position of the branches, certain compounds having certain required carbon atoms may have a melting point of less than the above preferred in the present invention. Such compounds of low melting point are not intended to be included in this section. Nonlimiting examples of the high melting point compounds are found in International Cosmetic Ingredient Dictionary, Fifth Edition, 1993, and CTFA Cosmetic Ingredient Handbook, Second Edition, 1992.
  • fatty alcohols are preferably used in the composition of the present invention.
  • the fatty alcohols useful herein are those having from about 14 to about 30 carbon atoms, preferably from about 16 to about 22 carbon atoms. These fatty alcohols are saturated and can be straight or branched chain alcohols.
  • Preferred fatty alcohols include, for example, cetyl alcohol (having a melting point of about
  • stearyl alcohol having a melting point of about 58-59°C
  • behenyl alcohol having a melting point of about 71°C
  • mixtures thereof are known to have the above melting point. However, they often have lower melting points when supplied, since such supplied products are often mixtures of fatty alcohols having alkyl chain length distribution in which the main alkyl chain is cetyl, stearyl or behenyl group. In the present invention, more preferred fatty alcohols are cetyl alcohol, stearyl alcohol and mixtures thereof.
  • high melting point fatty compounds useful herein include: cetyl alcohol, stearyl alcohol, and behenyl alcohol having tradenames KONOL series available from Shin Nihon Rika (Osaka, Japan), and NAA series available from NOF (Tokyo, Japan); pure behenyl alcohol having tradename 1-DOCOSANOL available from WAKO (Osaka, Japan).
  • a gel matrix is formed by the cationic surfactant, the high melting point fatty compound, and an aqueous carrier.
  • the gel matrix is suitable for providing various conditioning benefits, such as slippery feel during the application to wet hair and softness and moisturized feel on dry hair.
  • the total amount of the cationic surfactant and the high melting point fatty compound is from about 4.5%, preferably from about 5.0%, more preferably from about 5.5% by weight of the composition, in view of providing the benefits of the present invention, and to about 15%, preferably to about 14%, more preferably to about 13%, still more preferably to about 10% by weight of the composition, in view of spreadability and product appearance.
  • the cationic surfactant and the high melting point fatty compound are contained at a level such that the weight ratio of the cationic surfactant to the high melting point fatty compound is in the range of, preferably from about 1: 1 to about 1:10, more preferably from about 1:1.5 to about 1:7, still more preferably from about 1:2 to about 1:6, in view of providing improved wet conditioning benefits.
  • the composition of the present invention is substantially free of anionic surfactants, in view of stability of the gel matrix.
  • the composition being substantially free of anionic surfactants means that: the composition is free of anionic surfactants; or, if the composition contains anionic surfactants, the level of such anionic surfactants is very low.
  • composition of the present invention comprises an aqueous carrier.
  • level and species of the carrier are selected according to the compatibility with other components, and other desired characteristic of the product.
  • the carrier useful in the present invention includes water and water solutions of lower alkyl alcohols.
  • the lower alkyl alcohols useful herein are monohydric alcohols having 1 to 6 carbons, more preferably ethanol and isopropanol.
  • the aqueous carrier is substantially water.
  • Deionized water is preferably used.
  • compositions of the present invention comprise from about 20% to about 99%, preferably from about 30% to about 95%, and more preferably from about 80% to about 90% water.
  • the composition further comprises a polyol. It is believed that, with the addition of the polyol especially pre-addition of the polyol before emulsion formation, the composition has further reduced chunk and/or improved stability while reducing chunk such stability includes stable rheology and/or reduced syneresis.
  • Polyols can be included in the composition at a level of from about 0.5%, preferably from about 1%, more preferably from about 3%, and to about 20%, preferably to about 15%, more preferably to about 10%, more preferably to about 8% by weight of the composition.
  • Polyol useful herein are those having a molecular weight of from about 40 to about 500, preferably from about 50 to about 350, more preferably from about 50 to about 200, still more preferably from about 50 to about 150.
  • polyols useful herein have from 2 to 12 OH groups, more preferably, 2-6, 8 or 10 OH groups, still more preferably 2-6 OH groups, even more preferably 2-4 OH groups.
  • Polyols useful herein are preferably water soluble.
  • Water soluble polyols herein means those being soluble at a level used at 30°C.
  • Non-water soluble polyols are, for example, glyceryl stearate.
  • Polyols useful herein include, for example: pentaerythritol; propylene glycol; butylene glycol; glycerin; pentylene glycol; hexylene glycol; Diols such as 1, 2-diol, 1,3-diol, and other diols, the diols having a hydrocardon chain having 1-20 carbons, preferably 1-6 carbons; polyethylene glycol; polypropylene glycol; poly butylene glycol; polypentylene glycol; and polyhexylene glycol.
  • preferred are Glycerin, Butylene Glycol, Propylene glycol, more preferred are glycerin.
  • composition of the present invention further comprises an anionic polymer, preferably anionic deposition polymer.
  • anionic polymer is included at a level by weight of the composition of, from about 0.05% to about 6%, preferably from about 0.1% to about 5%, more preferably from about 0.2% to about 3.5%.
  • the anionic polymers useful herein are those comprising a vinyl monomer (A) with a carboxyl group, wherein the vinyl monomer (A) is contained in the polymer at a level of from about 40 mass% based on the total mass of the copolymer, preferably from about 50mass%, more preferably about 60 mass % or higher, and even more preferably about 70 mass% or higher, and to about 100 mass%, preferably about 90 mass% or less.
  • the weight ratio of (i) the anionic deposition polymer to (ii) a sum of the cationic surfactant and high melting point fatty compound is from about 1:1 to about 1:160, more preferably from about 1:2.5 to about 1:120, still more preferably from about 1:3.5 to about 1:80. If the weight ratio of (i) to (ii) is too low, the composition may provide lower deposition of cationic surfactants, high melting point fatty compounds, and/or silicone compounds. If the weight ratio of (i) to (ii) is too high, the composition may influence rheology, and may undesirably decrease rheology of the composition.
  • Anionic deposition polymer The deposition polymer useful herein is a copolymer comprising: a vinyl monomer (A) with a carboxyl group in the structure; and a vinyl monomer (B) expressed by the following formula (1):
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents a hydrogen atom or an alkyl group with from 1 to 5 carbon atoms, which may have a substitution group
  • Q represents an alkylene group with from 2 to 4 carbon atoms which may also have a substitution group
  • r represents an integer from 2 to 15
  • X represents an oxygen atom or an NH group
  • the vinyl monomer (A) is contained at a level of from about 50 mass to about 90 mass
  • the vinyl monomer (B) is contained at level of from about 10 mass to about 50 mass .
  • the copolymer of the present invention contains a vinyl monomer (A) having a carboxyl group in the structure.
  • the copolymer may contain one type of the vinyl monomer (A), or may contain two or more types of the vinyl monomer (A).
  • the vinyl monomer (A) is preferably anionic.
  • This vinyl monomer (A) is contained at a level of from about 50 mass based on the total mass of the copolymer, preferably from about 55mass , more preferably about 60 mass % or higher, and even more preferably about 65 mass or higher, in view of improved deposition of cationic surfactants, fatty compounds and/or silicones, and to about 90 mass , preferably about 85 mass or less, and more preferably about 80 mass or less, in view of not-deteriorating smoothness during application and/or the product viscosity.
  • Non-limited example of the vinyl monomer (A) having a carboxyl group include, for example, unsaturated carboxylic acid monomers having 3 to 22 carbon atoms.
  • the unsaturated carboxylic acid monomer has, preferably 4 or more carbon atoms, and preferably 20 or less carbon atoms, more preferably 18 or less carbon atoms, still more preferably 10 or less carbon atoms, and even more preferably 6 or less carbon atoms.
  • the number of carboxyl groups in the vinyl monomer (A) is preferably from 1 to 4, more preferably from 1 to 3, even more preferably from 1 to 2, and most preferably 1.
  • R 3 represents a hydrogen atom or a methyl group, preferably a hydrogen atom; m represents an integer of 1 through 4, preferably 2 to 3; and n represents an integer of 0 through 4, preferably 0 to 2, and most preferably 0
  • R 4 represents a hydrogen atom or a methyl group, preferably a hydrogen atom; p and q independently represent an integer of 2 through 6, preferably 2 to 3.
  • Examples of those expressed by the formula (2) include (meth)acrylic acid, crotonic acid, maleic acid, fumaric acid, itaconic acid, angelic acid, tiglic acid, 2-carboxy ethyl acrylate oligomer, and the like. Among them, preferred are acrylic acid and methacrylic acid, and more preferred is acrylic acid. Examples of those expressed by the formula (3) include acryloyloxy ethyl succinate, 2-methacryloyloxy ethyl succinate, and the like.
  • the copolymer contains a vinyl monomer (B).
  • the copolymer may contain one type of the vinyl monomer (B), or may contain two or more types of the vinyl monomer (B).
  • the vinyl monomer (B) is preferably nonionic.
  • the vinyl monomer (B) is contained at a level of from about 10 mass , preferably from about 15mass , more preferably from about 20mass based on the total mass of the copolymer in view of improving the feel and the smoothness during application, and to about 50 mass based on the total mass of the copolymer, preferably to about 45 mass , more preferably to about 40 mass , still more preferably about 35 mass , in view of improved deposition of cationic surfactants, fatty compounds and/or silicones.
  • the Vinyl monomers (B) useful herein are those expressed by formula (4)
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents a hydrogen atom or an alkyl group with 1 through 5 carbon atoms, which may have a substitution group
  • Q represents an alkylene group with 2 through 4 carbon atoms which may also have a substitution group
  • r represents an integer from 2 through 15
  • X represents an oxygen atom or an NH group
  • R 2 has a substitution group
  • the substitution group is a substitution group that does not react with other parts of the copolymer.
  • the vinyl monomer (B) is preferably hydrophilic, and therefore R 2 is preferably a hydrogen atom or an alkyl group with 1 - 3 carbon atoms, and more preferably a hydrogen atom or an alkyl group with 1 or 2 carbon atoms.
  • X preferably represents an oxygen atom.
  • Q represents preferably an alkylene group with 2 through 3 carbon atoms which may also have a substitution group, and more preferably an alkylene group with 2 through 3 carbon atoms without any substitution group. If the alkylene group of Q has a substitution group, it is preferred that such substitution group does not react with other parts of the copolymer, more preferably such substitution group has a molecular weight of 50 or less, still more preferably such substitution group has a molecular weight that is smaller than the structural moiety of - (Q - 0)r -. Examples of such substitution group include a hydroxyl group, methoxy group, ethoxy group, and the like.
  • r represents preferably 3 or higher, and preferably 12 or less, in view of improved deposition of cationic surfactants, fatty compounds and/or silicones, and/or in view of smoothness during application.
  • the number of atoms that are bonded by the straight chain is 70 or less.
  • the number of atoms that are bonded in the straight chain of the structure - (Q - 0)r - R 2 is calculated as 80, which therefore is outside of the scope.
  • the number of atoms bonded in the straight chain in the structure - (Q - 0)r - R 2 is preferably 60 or less, more preferably 40 or less, even more preferably 28 or less, and particularly preferably 20 or less, in view of improved deposition of cationic surfactants, fatty compounds and/or silicones, and/or in view of smoothness during application.
  • vinyl monomer (B) examples include, methoxy polyethylene glycol (meth) aery late
  • polyethylene glycol (meth)acrylate where the number of repetitions of polyethylene glycol (r in formula (4)) is between 2 ⁇ 15
  • methoxy polyethylene glycol / polypropylene glycol (meth)acrylate where the number of repetitions of polyethylene glycol / polypropylene glycol (r in formula (4)) is between 2 ⁇ 15
  • polyethylene glycol / polypropylene glycol (meth)acrylate where the number of repetitions of polyethylene glycol / polypropylene glycol (r in formula (4)) is between 2 ⁇ 15
  • methoxy polyethylene glycol / polybutylene glycol (meth)acrylate where the number of repetitions of polyethylene glycol / polybutylene glycol (r in formula (4)) is between 2 - 15
  • polyethylene glycol / polybutylene glycol (meth)acrylate where the number of repetitions of polyethylene glycol / polybutylene glycol (meth)acrylate (where the number of repetitions of polyethylene glycol
  • the copolymer may further contain a vinyl monomer (C) having an alkyl group with 12 ⁇ 22 carbon atoms, in view of providing conditioning effect such as smoothness during application.
  • a vinyl monomer (C) having an alkyl group with 12 ⁇ 22 carbon atoms in view of providing conditioning effect such as smoothness during application.
  • the amount of the vinyl monomer (C) is preferably 40 mass or less, more preferably 30 mass or less, even more preferably 25 mass or less, and still more preferably 20 mass or less based on the total mass of the copolymer, in view of improved deposition of cationic surfactants, fatty compounds and/or silicones, and/or in view of smoothness during application.
  • the vinyl monomer (C) is a (meth)acrylate monomer having an alkyl group with 12 ⁇ 22 carbon atoms, in view of smoothness during application. Furthermore, vinyl monomers with branched alkyl groups are particularly preferred.
  • Examples of the (meth)acrylate monomer having an alkyl group with 12 ⁇ 22 carbon atoms include myristyl (meth)acrylate, isostearyl (meth)acrylate, stearyl (meth)acrylate, behenyl (meth)acrylate, cetyl (meth)acrylate, lauryl (meth)acrylate, synthetic lauryl (meth)acrylate, (however "synthetic lauryl (meth)acrylate” refers to an alkyl (meth)acrylate having alkyl groups with 12 carbon atoms and alkyl groups with 13 carbon atoms), and the like. Of these, (meth)acrylate monomers having an alkyl group with 12 ⁇ 20 carbon atoms are preferable, and (meth)acrylate monomers having an alkyl group with 16 ⁇ 18 carbon atoms are more preferable.
  • the copolymer may contain one type of the vinyl monomer (C), or may contain two or more types of the vinyl monomer (C).
  • the copolymer may also contain other vinyl monomers, to the extent not to deteriorate the effect of the copolymer.
  • examples of other vinyl monomers include nonionic monomers, amphoteric monomers, semi- polar monomers, cationic monomers, as well as monomers containing a polysiloxane group., preferably nonionic monomers with or without polysiloxane group These other monomers are different from any of the aforementioned vinyl monomers (A), (B), and (C).
  • the amount of such other monomers, if included, is 40 mass or less of the total mass of the copolymer, preferably 30 mass or less, more preferably 20 mass or less, and even more preferably 10 mass or less.
  • the amount of cationic functional groups in the copolymer is preferably low, and for example cationic functional groups preferably account for 10 mole % or less of all functional groups in the copolymer. More preferably, the copolymer is free of cationic functional groups.
  • nonionic monomers examples include esters of (meth)acrylic acid and alcohols with 1 ⁇ 22 carbon atoms, amides of (meth)acrylic acid and alkyl amines with 1 - 22 carbon atoms, monoesters of (meth)acrylic acid and ethylene glycol, 1,3-propylene glycol or the like, as well as esters where the hydroxyl group of the monoester has been etherified by methanol, ethanol or the like, (meth)acryloyl morpholine and the like.
  • amphoteric monomers examples include (meth)acryl esters having a betaine group, (meth)acrylamide having a betaine group and the like.
  • semipolar monomers examples include (meth)acrylate esters having an amine oxide group, (meth)acrylamides having an amine oxide group, and the like.
  • Examples of cationic monomers include (meth)acrylate esters having a quaternary ammonium group, (meth)acrylamides having a quaternary ammonium group and the like.
  • the monomer containing a polysiloxane group is a monomer having a polysiloxane structure and also having a structure that can bond by covalent bond to the copolymer.
  • These component units have high affinity towards silicone oil that is normally used in conjunction in cosmetic material compositions, and are thought to act by bonding the silicone oil to the other component units in the copolymer and thus increasing the adsorption force of silicone oil to the skin and hair, particularly damaged hair.
  • the polysiloxane structure is a structure where two or more repeating structural units expressed by the following formula (4) are linked.
  • R 5 and R 6 independently represent an alkyl group with 1 to 3 carbon atoms or a phenyl group.
  • the structure that can link via covalent bond to the copolymer can be a structure that has a vinyl structure such as a (meth)acrylate ester, or (meth)acrylamide and that can copolymerize with another monomer, a structure that has a functional group such as a thiol, that can link to the copolymer by chain transfer during polymerization, or a structure that has an isocyanate group, carboxylic acid group, hydroxyl group, amino group, or the like, and that can react and link to the functional groups on the copolymer, but there is no restriction to these structures.
  • a plurality of these linkable structures can be present in one monomer containing a polysiloxane group.
  • the polysiloxane structure can link by a graft structure to the main chain, or conversely the polysiloxane structure can be the main chain with the other structure link by a graft structure, and in addition the polysiloxane structure and the other structure can be linked in a straight chain condition by a block structure.
  • the monomer containing a polysiloxane group is preferably expressed by the following formula (5).
  • R 7 represents a hydrogen atom or a methyl group
  • R 8 and R 9 independently represent an alkyl group with 1 to 3 carbon atoms or a phenyl group
  • R 10 represents an alkyl group with 1 to 8 carbon atoms
  • Z represents a bivalent linking group or a direct bond
  • s represents an integer between 2 to 200.
  • s is 3 or higher, and even more preferably, s is 5 or higher, in view of increased affinity to silicone oil, and preferably s is 50 or less, in view of enhanced copolymerization with the other monomers.
  • Z represents a bivalent linking group or a direct bond, but a linking group containing one or a combination of two or more of the structures suggested below is preferable.
  • the numbers that are combined is not particularly restricted, but normally is 5 or less.
  • the direction of the following structures are arbitrary (the polysiloxane group side can be on either end).
  • R represents an alkylene group with 1 to 6 carbon atoms or a phenylene group.
  • the monomer expressed by the aforementioned formula (5) include, for example, a-(vinyl phenyl) polydimethyl siloxane, a-(vinyl benzyloxy propyl) polydimethyl siloxane, a-(vinyl benzyl) polymethyl phenyl siloxane, a-(methacryloyl oxypropyl) polydimethyl siloxane, a- (methacryloyloxy propyl) polymethyl phenyl siloxane, a-(methacryloyl amino propyl) polydimethyl siloxane and the like.
  • the monomer containing a polysiloxane group can be a single type, or can be two or more types used in combination.
  • a cross-linking agent such as a polyfunctional acrylate or the like can be introduced to the copolymer.
  • a cross-linking agent is not included in the copolymer.
  • the amount of the vinyl monomers (A), (B), and (C) as well as other monomers in the copolymer can be measured using IR absorption or Raman scattering by the carbonyl groups, amide bonds, polysiloxane structures, various types of functional groups, carbon backbone and the like, by ⁇ -NMR of methyl groups in the polydimethyl siloxane, amide bond sites, and methyl groups and methylene groups adjacent thereto, as well as various types of NMR represented by 13 C-NMR and the like.
  • the weighted average molecular weight of the copolymer is preferably about 3,000 or higher, more preferably about 5,000 or higher, and even more preferably about 10,000 or higher, in view of providing conditioning effect via foaming a complex with cationic surfactant, and preferably to about 2,000,000, more preferably about 1,000,000 or less, still more preferably about 500,000 or less, even more preferably about 100,000 or less, and most preferably about 50,000 or less, in view of feeling after drying.
  • the weighted average molecular weight of the copolymer can be measured by gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • the development solvent that is used in gel permeation chromatography is not particularly restricted so long as being a normally used solvent, but for example, the measurement can be performed using a solvent blend of water / methanol / acetic acid / sodium acetate.
  • the copolymer preferably has a viscosity for a 20 mass ethanol solution at 25°C of 5 mPa»s or higher and 20,000 mPa»s or less.
  • the viscosity is more preferably 10 mPa»s or higher, even more preferably 15 mPa»s or higher, but on the other hand is more preferably 10,000 mPa»s or less, and even more preferably 5,000 mPa»s or less.
  • the viscosity of the copolymer is preferably 5 mPa»s or higher and 20,000 mPa»s or less, from the perspective of handling.
  • the viscosity can be measured using a B-type viscometer.
  • the viscosity of the copolymer can be adjusted by controlling the degree of polymerization of the copolymer, and can be controlled by increasing or decreasing the amount of a cross-linking agent such as a polyfunctional acrylate or the like that is added.
  • compositions of the present invention may further comprise a silicone compound.
  • the silicone compounds are included at levels by weight of the composition of from about 0.05% to about 15%, preferably from about 0.1% to about 10%, more preferably from about 0.1% to about 8%.
  • the silicone compounds have an average particle size of from about lmicrons to about 50 microns, in the composition.
  • the silicone compounds useful herein, as a single compound, as a blend or mixture of at least two silicone compounds, or as a blend or mixture of at least one silicone compound and at least one solvent, have a viscosity of preferably from about 1,000 to about 2,000,000mPa-s at 25°C.
  • Suitable silicone fluids include polyalkyl siloxanes, polyaryl siloxanes, polyalkylaryl siloxanes, polyether siloxane copolymers, amino substituted silicones, quaternized silicones, and mixtures thereof. Other nonvolatile silicone compounds having conditioning properties can also be used.
  • Silicone compounds useful herein also include amino substituted materials.
  • Preferred aminosilicones include, for example, those which conform to the general formula (I):
  • G is hydrogen, phenyl, hydroxy, or Ci-Cs alkyl, preferably methyl
  • a is 0 or an integer having a value from 1 to 3, preferably 1
  • b is 0, 1 or 2, preferably 1
  • n is a number from 0 to 1,999
  • m is an integer from 0 to 1,999; the sum of n and m is a number from 1 to 2,000; a and m are not both 0
  • Ri is a monovalent radical conforming to the general formula CqH 2q L, wherein q is an integer having a value from 2 to 8 and L is selected from the following groups: -N(R 2 )CH 2 -CH 2 -N(R 2 ) 2 ; -N(R
  • Such highly preferred amino silicones can be called as terminal aminosilicones, as one or both ends of the silicone chain are terminated by nitrogen containing group.
  • the above aminosilicones when incorporated into the composition, can be mixed with solvent having a lower viscosity.
  • solvents include, for example, polar or non-polar, volatile or non-volatile oils.
  • oils include, for example, silicone oils, hydrocarbons, and esters.
  • the non- volatile linear silicones useful herein are those having a viscosity of from about 1 to about 20,000 centistokes, preferably from about 20 to about 10,000 centistokes at 25°C.
  • non-polar, volatile hydrocarbons especially non-polar, volatile isoparaffins
  • Such mixtures have a viscosity of preferably from about l,000mPa-s to about 100,000mPa- s, more preferably from about 5,000mPa- s to about 50,000mPa-s.
  • alkylamino substituted silicone compounds include those having alkylamino substitutions as pendant groups of a silicone backbone. Highly preferred are those known as "amodimethicone". Commercially available amodimethicones useful herein include, for example, BY16-872 available from Dow Corning.
  • Silicone compounds useful herein also include polyalkyl siloxanes such as polydimethylsiloxane, polydiethylsiloxane, and polymethylphenylsiloxane.
  • Polydimethylsiloxane which is also known as dimethicone, is especially preferred. These silicone compounds are available, for example, from the General Electric Company in their
  • the above polyalkylsiloxanes are available, for example, as a mixture with silicone compounds having a lower viscosity.
  • Such mixtures have a viscosity of preferably from about l,000mPa- s to about 100,000mPa- s, more preferably from about 5,000mPa-s to about 50,000mPa-s.
  • Such mixtures preferably comprise: (i) a first silicone having a viscosity of from about 100,000mPa-s to about 30,000,000mPa- s at 25°C, preferably from about 100,000mPa-s to about 20,000,000mPa-s; and (ii) a second silicone having a viscosity of from about 5mPa-s to about 10,000mPa- s at 25°C, preferably from about 5mPa-s to about 5,000mPa-s.
  • Such mixtures useful herein include, for example, a blend of dimethicone having a viscosity of 18,000,000mPa- s and dimethicone having a viscosity of 200mPa-s available from GE Toshiba, and a blend of dimethicone having a viscosity of 18,000,000mPa-s and cyclopentasiloxane available from GE Toshiba.
  • the silicone compounds useful herein also include a silicone gum.
  • silicone gum means a polyorganosiloxane material having a viscosity at 25 °C of greater than or equal to 1,000,000 centistokes. It is recognized that the silicone gums described herein can also have some overlap with the above-disclosed silicone compounds. This overlap is not intended as a limitation on any of these materials.
  • the "silicone gums” will typically have a mass molecular weight in excess of about 200,000, generally between about 200,000 and about 1,000,000.
  • silicone gums are available, for example, as a mixture with silicone compounds having a lower viscosity.
  • Such mixtures useful herein include, for example, Gum/Cyclomethicone blend available from Shin-Etsu.
  • the silicone compounds may further be incorporated in the present composition in the form of an emulsion, wherein the emulsion is made my mechanical mixing, or in the stage of synthesis through emulsion polymerization, with or without the aid of a surfactant selected from anionic surfactants, nonionic surfactants, cationic surfactants, and mixtures thereof.
  • Silicone compounds useful herein include, for example, a Silicone Polymer Containing Quaternary Groups comprising terminal ester groups, having a viscosity up to 100,000 mPa-s and a D block length of greater than 200 D units. Without being bound by theory, this low viscosity silicone polymer provides improved conditioning benefits such as smooth feel, reduced friction, and prevention of hair damage, while eliminating the need for a silicone blend.
  • the silicone polymer is a polyorganosiloxane compound comprising one or more quaternary ammonium groups, at least one silicone block comprising greater than 200 siloxane units, at least one polyalkylene oxide structural unit, and at least one terminal ester group.
  • the silicone block may comprise between 300 to 500 siloxane units.
  • the silicone polymer is present in an amount of from about 0.05% to about 15%, preferably from about 0.1% to about 10%, more preferably from about 0.15% to about 5%, and even more preferably from about 0.2% to about 4% by weight of the composition.
  • the polyorganosiloxane compounds have the general formulas (la) and (lb):
  • m is > 0, preferred 0.01 to 100, more preferred 0.1 to 100, even more preferred 1 to 100, specifically 1 to 50, more specifically 1 to 20, even more specifically 1 to 10,
  • k is 0 or an average value of from >0 to 50, or preferably from 1 to 20, or even more preferably from 1 to 10,
  • M represents a terminal group, comprising terminal ester groups selected from
  • Z is selected from monovalent organic residues having up to 40 carbon atoms, optionally comprising one or more hetero atoms.
  • a and A' each are independently from each other selected from a single bond or a divalent organic group having up to 10 carbon atoms and one or more hetero atoms, and
  • E is a polyalkylene oxide group of the general formula:
  • R 2 is selected from hydrogen or R
  • R is selected from monovalent organic groups having up to 22 carbon atoms and optionally one or more heteroatoms, and wherein the free valencies at the nitrogen atoms are bound to carbon atoms,
  • Y is a group of the formula:
  • K is a bivalent or trivalent straight chain, cyclic and/or branched C2-C40 hydrocarbon residue which is optionally interrupted by— O— ,— NH— , trivalent N,— NR 1 — ,— C(O)— , — C(S)— , and optionally substituted with— OH, wherein R 1 is defined as above,
  • T is selected from a divalent organic group having up to 20 carbon atoms and one or more hetero atoms.
  • the residues K may be identical or different from each other.
  • the residue K is bound to the silicon atom of the residue S via a C-Si-bond.
  • amine groups (— (NR 2 — A— E— A'— NR 2 )— ) in the polyorganosiloxane compounds, they may have protonated ammonium groups, resulting from the protonation of such amine groups with organic or inorganic acids. Such compounds are sometimes referred to as acid addition salts of the polyorganosiloxane compounds.
  • the molar ratio of the quaternary ammonium groups b) and the terminal ester groups c) is less than 100 : 20, even more preferred is less than 100 : 30 and is most preferred less than 100 : 50.
  • the ratio can be determined by 13 C-NMR.
  • the polyorganosiloxane composition may comprise:
  • A) at least one polyorganosiloxane compound comprising a) at least one polyorganosiloxane group, b) at least one quaternary ammonium group, c) at least one terminal ester group, and d) at least one polyalkylene oxide group (as defined before),
  • the polyorganosiloxane compound B) differs from the polyorganosiloxane compound A) preferably in that it does not comprise quaternary ammonium groups.
  • Preferred polyorganosiloxane compounds B) result from the reaction of monofunctional organic acids, in particular carboxylic acids, and polyorganosiloxane containing bisepoxides.
  • the weight ratio of compound A) to compound B) is preferably less than 90 : 10. Or in other words, the content of component B) is at least 10 weight percent.
  • the molar ratio of the quaternary ammonium groups b) and the terminal ester groups c) is less than 100 : 10, even more preferred is less than 100 : 15 and is most preferred less than 100 : 20.
  • the silicone polymer has a viscosity at 20°C and a shear rate of 0.1s "1 (plate-plate system, plate diameter 40mm, gap width 0.5mm) of less than 100,000 mPa»s (100 Pa»s).
  • the viscosities of the neat silicone polymers may range from 500 to 100,000 mPa»s, or preferably from 500 to 70,000 mPa»s, or more preferably from 500 to 50,000 mPa»s, or even more preferably from 500 to 20,000 mPa»s.
  • the viscosities of the neat polymers may range from 500 to 10,000 mPa»s, or preferably 500 to 5000 mPa»s determined at 20 °C and a shear rate of 0.1 s "1 .
  • q 0 to 200, or preferably from 0 to 100, or more preferably from 0 to 50, or even more preferably from 0 to 20,
  • r 0 to 200, or preferably from 0 to 100, or more preferably from 0 to 50, or even more preferably from 0 to 20,
  • s 0 to 200, or preferably from 0 to 100, or more preferably from 0 to 50, or even more preferably from 0 to 20,
  • q+r+s 1 to 600, or preferably from 1 to 100, or more preferably from 1 to 50, or even more preferably from 1 to 40.
  • K in the group— K— S— K— ) is preferably a bivalent or trivalent straight chain, cyclical or branched C2-C2 0 hydrocarbon residue which is optionally interrupted by— O— ,— NH— , trivalent N,— NR 1 — ,— C(O)— ,— C(S)— , and optionally substituted with— OH.
  • R 1 is Ci-Cis alkyl, Ci-Cis fluoroalkyl and aryl. Furthermore, R 1 is preferably Ci-Cis alkyl, Ci-C 6 fluoroalkyl and aryl. Furthermore, R 1 is more preferably Ci-C 6 alkyl, Ci-C 6 fluoroalkyl, even more preferably C1-C4 fluoroalkyl, and phenyl. Most preferably, R 1 is methyl, ethyl, trifluoropropyl and phenyl.
  • C1-C22 alkyl means that the aliphatic hydrocarbon groups possess from 1 to 22 carbon atoms which can be straight chain or branched.
  • Methyl, ethyl, propyl, n-butyl, pentyl, hexyl, heptyl, nonyl, decyl, undecyl, isopropyl, neopentyl and 1,2,3- trimethyl hexyl moieties serve as examples.
  • C1-C22 fluoroalkyl means aliphatic hydrocarbon compounds with 1 to 22 carbon atoms which can be straight chain or branched and are substituted with at least one fluorine atom.
  • Monofluormethyl, monofluoroethyl, 1,1,1- trifluorethyl, perfluoroethyl, 1,1,1 -trifluoropropyl, 1,2,2-trifluorobutyl are suitable examples.
  • aryl means unsubstituted or phenyl substituted once or several times with OH, F, CI, CF 3 , C C 6 alkyl, C C 6 alkoxy, C3-C7 cycloalkyl, C 2 -C 6 alkenyl or phenyl.
  • Aryl may also mean naphthyl.
  • the positive charges resulting from the ammonium group(s), are neutralized with inorganic anions such as chloride, bromide, hydrogen sulfate, sulfate, or organic anions, like carboxylates deriving from C1-C30 carboxylic acids, for example acetate, propionate, octanoate, especially from Cio-Cis carboxylic acids, for example decanoate, dodecanoate, tetradecanoate, hexadecanoate, octadecanoate and oleate, alkylpolyethercarboxylate, alkylsulphonate, arylsulphonate, alkylarylsulphonate, alkylsulphate, alkylpolyethersulphate, phosphates derived from phosphoric acid mono alkyl/aryl ester and phosphoric acid dialkyl/aryl ester.
  • inorganic anions such as chloride, bromide, hydrogen sulfate,
  • the quaternary ammonium groups are usually generated by reacting the di-tertiary amines with an alkylating agents, selected from in particular di-epoxides (sometimes referred to also as bis -epoxides) in the presence of mono carboxylic acids and difunctional dihalogen alkyl compounds.
  • an alkylating agents selected from in particular di-epoxides (sometimes referred to also as bis -epoxides) in the presence of mono carboxylic acids and difunctional dihalogen alkyl compounds.
  • polyorganosiloxane compounds are of the general formulas (la) and (lb):
  • polyorganosiloxane compounds may be also of the general formulas (Ila) or (lib):
  • Z is a straight chain, cyclic or branched saturated or unsaturated Ci-C 2 o, or preferably C 2 to C 18 , or even more preferably a hydrocarbon radical, which can be interrupted by one or more— O— , or— C(O)— and substituted with— OH.
  • M is -OC(0)-Z resulting from normal carboxylic acids in particular with more than 10 carbon atoms like for example dodecanoic acid.
  • the molar ratio of the polyorganosiloxane-containing repeating group— K— S— K— and the polyalkylene repeating group— A— E— A'— or— A'— E— A— is between 100:1 and 1:100, or preferably between 20:1 and 1:20, or more preferably between 10:1 and 1:10.
  • R may represent a monovalent straight chain, cyclic or branched Ci-C 2 o hydrocarbon radical, which can be interrupted by one or more— O— ,— C(O)— and can be substituted by— OH
  • T may represent a divalent straight-chain, cyclic, or branched Ci-C 2 o hydrocarbon radical, which can be interrupted by — O— ,— C(O)— and can be substituted by hydroxyl.
  • the above described polyorganosiloxane compounds comprising quaternary ammonium functions and ester functions may also contain: 1) individual molecules which contain quaternary ammonium functions and no ester functions; 2) molecules which contain quaternary ammonium functions and ester functions; and 3) molecules which contain ester functions and no quaternary ammonium functions. While not limited to structure, the above described polyorganosiloxane compounds comprising quaternary ammonium functions and ester functions are to be understood as mixtures of molecules comprising a certain averaged amount and ratio of both moieties.
  • Various monofunctional organic acids may be utilized to yield the esters.
  • Exemplary embodiments include Ci-C 3 o carboxylic acids, for example C 2 , C 3 , Cs acids, C 10 -C 18 carboxylic acids, for example C 12 , C M , C 16 acids, saturated, unsaturated and hydroxyl functionalized C 18 acids, alkylpolyethercarboxylic acids, alkylsulphonic acids, arylsulphonic acids, alkylarylsulphonic acids, alkylsulphuric acids, alkylpolyethersulphuric acids, phosphoric acid mono alkyl/aryl esters and phosphoric acid dialkyl/aryl esters.
  • composition of the present invention may include other additional components, which may be selected by the artisan according to the desired characteristics of the final product and which are suitable for rendering the composition more cosmetically or aesthetically acceptable or to provide them with additional usage benefits.
  • additional components generally are used individually at levels of from about 0.001% to about 10%, preferably up to about 5% by weight of the composition.
  • triglyceride oligomer derived from the self-metathesis of soybean oil which can be fully or partially hydrogenated, and which can be blended with other materials such as byproducts and/or non-metathesized unsaturated polyol esters.
  • An example of metathesis derived soy oligomers is the fully hydrogenated DOW CORNING® HY-3050 soy wax, available from Dow Corning.
  • DOW CORNING® HY-3051 DOW CORNING® HY-3051, a blend of HY-3050 oligomer and hydrogenated soybean oil (HSBO), available from Dow Corning.
  • Peptein 2000 available from Hormel vitamin E with tradename Emix-d available from Eisai
  • panthenol available from Roche panthenyl ethyl ether available from Roche
  • hydrolysed keratin proteins, plant extracts, and nutrients
  • preservatives such as benzyl alcohol, methyl paraben, propyl paraben and imidazolidinyl urea
  • pH adjusting agents such as citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium carbonate
  • coloring agents such as any of the FD&C or D&C dyes
  • perfumes ultraviolet and infrared screening and absorbing agents such as benzophenones
  • antidandruff agents such as zinc pyrithione.
  • compositions of the present invention can be in the form of rinse-off products or leave- on products, and can be formulated in a wide variety of product forms, including but not limited to creams, gels, emulsions, mousses and sprays.
  • the composition of the present invention is especially suitable for hair conditioners especially rinse-off hair conditioners.
  • composition of the present invention is preferably used for a method of conditioning hair, the method comprising following steps:
  • compositions (wt ) (wt )
  • compositions (wt ) (wt )
  • Anionic polymer- 1 Copolymer of 80wt% of acrylic acid monomer and 20wt% methoxyPEG-4methacrylate monomer, having a molecular weight of about 17,800.
  • Anionic polymer-2 Copolymer of 60wt of acrylic acid monomer and 40wt of methoxyPEG-4methacrylate monomer, having a molecular weight of about 17,000.
  • G is methyl; a is an integer of 1; b is 0, 1 or 2, preferably 1; n is a number from 400 to about 600; m is an integer of 0; Ri is a monovalent radical conforming to the general formula CqH 2q L, wherein q is an integer of 3 and L is -NH 2 Method of Preparation
  • Method I including E-METHOD
  • a Group W components are mixed with agitation, and heated to about 80°C, and Groups O components are added and mixed with agitation.
  • the mixture is cooled down to about 55°C and gel matrix is formed.
  • Other components are added to the gel matrix with agitation. Then the composition is cooled down to room temperature.
  • Group O components are mixed and heated to from about 66°C to about 85°C to form an oil phase.
  • Group W components are mixed and heated to from about 20°C to about 48°C to form an aqueous phase.
  • Becomix® direct injection rotor-stator homogenizer the oil phase is injected and it takes 0.2 second or less for the oils phase to reach to a high shear field having an energy density of from 1.0x10 s J/m 3 to l.OxlO 7 J/m 3 where the aqueous phase is already present.
  • a gel matrix is formed. Other components are added to the gel matrix with agitation. Then the composition is cooled down to room temperature.
  • chunk is evaluated by the following methods. Results of the evaluation are also shown above in Table and Fig. 1-4.
  • Examples 1 through 7 are hair care compositions made by the methods of the present invention which are particularly useful for rinse-off use.
  • the embodiments disclosed and represented by the previous "Ex. 1" through “Ex. 7" have many advantages. For example, they provide reduced chunks, especially reduced larger size of chunks.
  • Chunk is evaluated by direct visual evaluation and/or visual evaluation via microscope. Photographs of such image are shown in Fig. 1-4.

Abstract

L'invention concerne un procédé de préparation d'une composition de conditionnement pour les cheveux, la composition comprenant : un surfactant cationique à base de mono-alkyl amine ; un composé gras à point de fusion élevé ; un polymère anionique comprenant un pourcentage plus élevé d'un monomère de vinyle (A) avec un groupe carboxyle ; et un véhicule aqueux, le procédé comprenant une étape consistant à : mélanger le surfactant cationique, le composé gras à point de fusion élevé, le polymère anionique et le véhicule aqueux pour former une émulsion. Le procédé de la présente invention concerne des compositions de conditionnement pour les cheveux ayant moins de blocs tout en contenant à la fois des surfactants cationiques à base de mono-alkyl amine et de polymères anioniques contenant un pourcentage plus élevé de monomère de vinyle avec un groupe carboxyle.
PCT/US2015/037119 2014-06-25 2015-06-23 Procédé de préparation d'une composition de conditionnement pour les cheveux comprenant un surfactant cationique à base de mono-alkyl amine et un polymère anionique WO2015200284A1 (fr)

Priority Applications (4)

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MX2016016935A MX2016016935A (es) 2014-06-25 2015-06-23 Un metodo para preparar una composicion acondicionadora para el cabello que comprende surfactante cationico de monoalquil amina y polimero anionico.
CN201580034612.5A CN106456503A (zh) 2014-06-25 2015-06-23 制备包含单烷基胺阳离子表面活性剂和阴离子聚合物的毛发调理组合物的方法
EP15736721.0A EP3160432A1 (fr) 2014-06-25 2015-06-23 Procédé de préparation d'une composition de conditionnement pour les cheveux comprenant un surfactant cationique à base de mono-alkyl amine et un polymère anionique
JP2016573824A JP2017518337A (ja) 2014-06-25 2015-06-23 モノアルキルアミンカチオン性界面活性剤及びアニオン性ポリマーを含むヘアコンディショニング組成物の調製方法

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US62/016,669 2014-06-25

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EP3532017B1 (fr) 2017-04-13 2022-08-17 The Procter & Gamble Company Composition de produit comprenant une particule discrète et une composition de base aqueuse

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WO2013148904A1 (fr) * 2012-03-30 2013-10-03 The Procter & Gamble Company Composition d'après-shampoing comportant un système tensioactif cationique monoalkylamine, un polymère de dépôt et une silicone

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US20070010408A1 (en) * 2005-07-07 2007-01-11 The Procter & Gamble Company Conditioning compositions comprising coacervate and gel matrix
WO2013148904A1 (fr) * 2012-03-30 2013-10-03 The Procter & Gamble Company Composition d'après-shampoing comportant un système tensioactif cationique monoalkylamine, un polymère de dépôt et une silicone

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3532017B1 (fr) 2017-04-13 2022-08-17 The Procter & Gamble Company Composition de produit comprenant une particule discrète et une composition de base aqueuse

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EP3160432A1 (fr) 2017-05-03

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