WO1999024014A1 - Compositions pour traitement capillaire comprenant des tensioactifs cationiques hydrophiliquement substitues et des composes a point de fusion eleve - Google Patents

Compositions pour traitement capillaire comprenant des tensioactifs cationiques hydrophiliquement substitues et des composes a point de fusion eleve Download PDF

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Publication number
WO1999024014A1
WO1999024014A1 PCT/US1997/020736 US9720736W WO9924014A1 WO 1999024014 A1 WO1999024014 A1 WO 1999024014A1 US 9720736 W US9720736 W US 9720736W WO 9924014 A1 WO9924014 A1 WO 9924014A1
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Prior art keywords
hair conditioning
conditioning composition
melting point
mixtures
hair
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PCT/US1997/020736
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English (en)
Inventor
Hirotaka Uchiyama
Arata Mitsumatsu
Yukiko Mizoguchi
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The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to BR9714976-4A priority Critical patent/BR9714976A/pt
Priority to PCT/US1997/020736 priority patent/WO1999024014A1/fr
Priority to JP11507088A priority patent/JP2000513382A/ja
Priority to EP97949420A priority patent/EP1032365A1/fr
Priority to AU27041/99A priority patent/AU2704199A/en
Priority to CN98811244A priority patent/CN1279600A/zh
Priority to BR9812347-5A priority patent/BR9812347A/pt
Priority to KR1020007002882A priority patent/KR20010024125A/ko
Priority to EP98926401A priority patent/EP1014919A1/fr
Priority to CA002304275A priority patent/CA2304275C/fr
Priority to AU78247/98A priority patent/AU7824798A/en
Priority to TR2000/01027T priority patent/TR200001027T2/xx
Priority to HU0100622A priority patent/HUP0100622A3/hu
Priority to IL13503798A priority patent/IL135037A0/xx
Priority to IDW20000711D priority patent/ID24697A/id
Priority to PL98339367A priority patent/PL339367A1/xx
Priority to PCT/US1998/011781 priority patent/WO1999013838A1/fr
Publication of WO1999024014A1 publication Critical patent/WO1999024014A1/fr
Priority to NO20001352A priority patent/NO20001352L/no

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    • 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
    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone

Definitions

  • the present invention relates to a hair conditioning composition comprising high levels of conditioning agents. More specifically, the present invention relates to a hair conditioning composition comprising hydrophilically substituted cationic surfactants and high melting point compounds.
  • shampooing cleans the hair by removing excess soil and sebum.
  • shampooing can leave the hair in a wet, tangled, and generally unmanageable state. Once the hair dries, it is often left in a dry, rough, lusterless, or frizzy condition due to removal of the hair's natural oils and other natural conditioning and moisturizing components.
  • the hair can further be left with increased levels of static upon drying which can interfere with combing and result in a condition commonly referred to as "fly-away hair", or contribute to an undesirable phenomena of "split ends", particularly for long hair.
  • a variety of approaches have been developed to alleviate these after- shampoo problems.
  • conditioners which provide smoothness and softness to the hair and wet combing benefits.
  • a common method of providing conditioning benefit to the hair is through the use of hair conditioning agents such as cationic surfactants and polymers, silicone conditioning agents, and hydrocarbon and other organic oils, and solid aliphatics such as fatty alcohols.
  • Cationic surfactants and polymers, as well as oils and aliphatics are known to enhance hair shine and provide moistness, softness, wet and dry combing benefits and static control to the hair; however, they are also known to provide stickiness or greasy or waxy feeling.
  • the present invention is directed to a hair conditioning composition
  • a hair conditioning composition comprising: (a) a hydrophilically substituted cationic surfactant; (b) from about 5% to about 20% by weight of a high melting point compound; (c) an additional cationic surfactant; and (d) water; wherein ⁇ / ⁇ ⁇ 4000, where ⁇ is the weight percent of the high melting point compound; ⁇ is viscosity (cps) of the composition at a constant shear rate 2sec-1 after 1 minute, ⁇ being less than about 35000 cps.
  • the hair conditioning compositions of the present invention comprise hydrophilically substituted cationic surfactants in which at least one of the substituents contain one or more aromatic, ether, ester, amido, or amino moieties present as substituents or as linkages in the radical chain, wherein at least one of the radicals contains one or more hydrophilic moieties selected from alkoxy (preferably C-) - C3 alkoxy), polyoxyalkylene (preferably C-
  • hydrophilically substituted cationic surfactants permits the addition of increased levels of the high melting point conditioning agents herein, which is desirable because higher levels of such conditioning agents generally provide improved conditioning benefits to the hair.
  • the interaction between the hydrophilically substituted cationic surfactants and the high melting point conditioning agents herein may be described as follows. Because these conditioning agents are solid aliphatics that tend to increase the viscosity of the composition to an undesirably high level if added in high quantities, it is necessary to reduce the viscosity of the composition so as to compensate for the viscosity increase that tends to result from the heightened levels of the conditioning agents in the compositions of the present invention.
  • the hydrophilically substituted cationic surfactant is believed to reduce the viscosity of the compositions herein, thus providing viscosity reduction not seen with other hydrogenated or partially hydrogenated cationic surfactants. It is such viscosity reduction that allows the addition of increased levels of high melting point conditioning agent to the present compositions.
  • compositions of the present invention where ⁇ is the weight percent of high melting point conditioning compound present in the composition; and ⁇ is the viscosity (cps) of the composition at a constant shear rate 2sec-1 after 1 minute: ⁇ / ⁇ ⁇ 4000
  • ⁇ is between about 5% and about 20% by weight of the composition.
  • ⁇ is less than about 35000 cps, more preferably less than about 32000 cps.
  • ⁇ / ⁇ is less than 3000, still more preferably less than 2500.
  • the hydrophilically substituted cationic conditioning surfactant contains from 2 to about 10 nonionic hydrophile moieties located within the above stated ranges.
  • Preferred hydrophilically substituted cationic surfactants include those of the formulas (I) through (VII) below:
  • n is from 8 to about 28, x+y is from 2 to about 40, Z ⁇ is a short chain alkyl, preferably a C «
  • ⁇ 2 is an alkyl, preferably a C-
  • R13 is a hydrocarbyl, preferably a C1 - C3 alkyl, more preferably methyl
  • Z 4 and Z 5 are, independently, short chain hydrocarbyls, preferably C2 - C4 alkyl or alkenyl, more preferably ethyl
  • a is from 2 to about 40, preferably from about 7 to about 30, and
  • X is a salt forming anion as defined above;
  • R ⁇ 4 and R 1 ⁇ independently, are C-
  • Z ⁇ is a C12 - C22 hydrocarbyl, alkyl carboxy or alkylamido
  • A is a protein, preferably a collagen, keratin, milk protein, silk, soy protein, wheat protein, or hydrolyzed forms thereof; and
  • X is a salt forming anion as defined above;
  • Nonlimiting examples of hydrophilically substituted cationic surfactants useful in the present invention include the materials having the following CTFA designations: quatemium-16, quatemium-26, quaternium-27, quaternium-30, quaternium-33, quaternium-43, quaternium-52, quaternium-53, quaternium-56, quaternium-60, quaternium-61 , quatemium-62, quaternium-70, quaternium-71 , quaternium-72, quatemium-75, quaternium-76 hydrolyzed collagen, quaternium-77, quaternium- 78, quaternium-79 hydrolyzed collagen, quaternium-79 hydrolyzed keratin, quaternium-79 hydrolyzed
  • hydrophilically substituted cationic surfactants include dialkylamido ethyl hydroxyethylmonium salt, dialkylamido ethyl dimonium salt, dialkoyl ethyl hydroxyethylmonium salt, dialkoyl ethyldimonium salt, and mixtures thereof, for example as commercially available under the following tradenames: VARISOFT 110, VARIQUAT K1215 and 638 from Witco Chemical; MACKPRO KLP, MACKPRO WLW, MACKPRO MLP, MACKPRO NSP, MACKPRO NLW, MACKPRO WWP, MACKPRO NLP, MACKPRO SLP from Mclntyre; ETHOQUAD 18/25, ETHOQUAD O/12PG, ETHOQUAD C/25, ETHOQUAD S/25, and ETHODUOQUAD from Akzo; DEHYQUAT SP from Henkel; and ATLAS G265 from ICI Americas; with VARISOFT 110 being
  • compositions of the present invention preferably include up to about 20% by weight of the hydrophilically substitued cationic surfactants, more preferably up to about 10% by weight.
  • the hair conditioning compositions of the present invention comprise a high melting point compound having a melting point of at least about 25°C selected from the group consisting of fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, hydrocarbons, steroids, and mixtures thereof.
  • these high melting point compounds cover the hair surface and reduce friction, thereby resulting in providing smooth feel on the hair and ease of combing.
  • 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.
  • a given classification is not intended to be a limitation on that particular compound, but is done so for convenience of classification and nomenclature.
  • certain compounds having certain required carbon atoms may have a melting point of less than about 25°C. 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, both of which are incorporated by reference herein in their entirety.
  • 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 can be straight or branched chain alcohols and can be saturated or unsaturated. Nonlimiting examples of fatty alcohols include, cetyl alcohol, stearyl alcohol, behenyl alcohol, and mixtures thereof.
  • the fatty acids useful herein are those having from about 10 to about 30 carbon atoms, preferably from about 12 to about 22 carbon atoms, and more preferably from about 16 to about 22 carbon atoms. These fatty acids can be straight or branched chain acids and can be saturated or unsaturated. Also included are diacids, triacids, and other multiple acids which meet the requirements herein. Also included herein are salts of these fatty acids. Nonlimiting examples of fatty acids include lauric acid, palmitic acid, stearic acid, behenic acid, sebacic acid, and mixtures thereof.
  • the fatty alcohol derivatives and fatty acid derivatives useful herein include alkyl ethers of fatty alcohols, alkoxylated fatty alcohols, alkyl ethers of alkoxylated fatty alcohols, esters of fatty alcohols, fatty acid esters of compounds having esterifiable hydroxy groups, hydroxy-substitued fatty acids, and mixtures thereof.
  • Nonlimiting examples of fatty alcohol derivatives and fatty acid derivatives include materials such as methyl stearyl ether; the ceteth series of compounds such as ceteth-1 through ceteth-45, which are ethylene glycol ethers of cetyl alcohol, wherein the numeric designation indicates the number of ethylene glycol moieties present; the steareth series of compounds such as steareth-1 through 10, which are ethylene glycol ethers of steareth alcohol, wherein the numeric designation indicates the number of ethylene glycol moieties present; ceteareth 1 through ceteareth-10, which are the ethylene glycol ethers of ceteareth alcohol, i.e.
  • Hydrocarbons useful herein include compounds having at least about 20 carbons.
  • Steroids useful herein include compounds such as cholesterol.
  • High melting point compounds of a single compound of high purity are preferred.
  • Single compounds of pure fatty alcohols selected from the group of pure cetyl alcohol, stearyl alcohol, and behenyl alcohol are highly preferred.
  • pure herein, what is meant is that the compound has a purity of at least about 90%, preferably at least about 95%.
  • high melting point compounds useful herein include: cetyl alchol, stearyl alcohol, and behenyl alcohol having tradenames KONOL series available from New Japan Chemical (Osaka, Japan), and NAA series available from NOF (Tokyo, Japan); pure behenyl alcohol having tradename 1-DOCOSANOL available from WAKO (Osaka, Japan), various fatty acids having tradenames NEO-FAT available from Akzo (Chicago Illinois, USA), HYSTRENE available from Witco Corp. (Dublin Ohio, USA), and DERMA available from Vevy (Genova, Italy); and cholesterol having tradename NIKKOL AGUASOME LA available from Nikko.
  • compositions of the present invention include from about 5% to about 20% by weight of the high melting point compound.
  • compositions of the present invention comprise an additional cationic surfactant.
  • the additional cationic surfactants herein are any known to the artisan, other than the hydrophilically substituted cationic surfactants described elsewhere herein.
  • the additional cationic surfactants herein are used at levels from about 0.01% to about 20.0%, preferably from about 0.1% to about 15.0%, and more preferably from about 0.25% to about 10.0%.
  • R 1 , R 2 , R 3 , and R 4 is selected from an aliphatic group of from 8 to 30 carbon atoms or an aromatic, alkoxy, polyoxyalkylene, aikylamido, hydroxyalkyl, aryl or alkylaryl group having up to about 22 carbon atoms, the remainder of R1 , R 2 , R3_ and R 4 are independently selected from an aliphatic group of from 1 to about 22 carbon atoms or an aromatic, alkoxy, polyoxyalkylene, aikylamido, hydroxyalkyl, aryl or alkylaryl group having up to about 22 carbon atoms; and X is a salt-forming anion such as those selected from halogen, (e.g.
  • 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 12 carbons, or higher, can be saturated or unsaturated. Preferred is when R-' , R 2 , R 3 , and R 4 are independently selected from Ci to about C22 alkyl.
  • Nonlimiting examples of cationic surfactants useful in the present invention include the materials having the following CTFA designations: quaternium-8, quaternium-14, quaternium-18, quaternium-18 methosulfate, quaternium-24, and mixtures thereof. Salts of primary, secondary, and tertiary fatty amines are also suitable additional cationic surfactants.
  • the alkyl groups of such amines preferably have from about 12 to about 22 carbon atoms, and can be substituted or unsubstituted. Particularly useful are amido substituted tertiary fatty amines.
  • Such amines include stearamidopropyldimethylamine, stearamidopropyldiethylamine, stearamidoethyldiethylamine, stearamidoethyldimethylamine, palmitamidopropyldimethylamine, palmitamidopropyldiethylamine, palmitamidoethyldiethylamine, palmitamidoethyldimethylamine, behenamidopropyldimethylamine, behenamidopropyldiethylamine, behenamidoethyldiethylamine, behenamidoethyldimethylamine, arachidamidopropyldimethylamine, arachidamidopropyldiethylamine, arachidamidoethyldiethylamine, arachidamidoethyldimethylamine, diethylaminoethylstearamide.
  • Stearamidopropyldimethylamines are herein preferred, and include those available under the tradenames AMIDOAMINE MPS from Nikko; ANDOGEN S- 18 from Witco; CHEMIDEX S from Chemron; INCROMINE SB from Croda, Inc.; LEXAMINE S-13 from Inolex; MACKINE 301 from Mclntyre; IRAMINE SODI from Rhone-Poulenc; SCHERCODINE S from Scher; TEGAMINE 18 and TEGO- AMID S 18 from Goldschmidt; and UNIZEEN SA from UPI.
  • dimethylstearamine dimethylsoyamine, soyamine, myristylamine, tridecylamine, ethylstearylamine, N-tallowpropane diamine, ethoxylated (with 5 moles of ethylene oxide) stearylamine, dihydroxyethylstearylamine, and arachidylbehenylamine.
  • These amines can also be used in combination with acids such as L-glutamic acid, lactic acid, hydrochloric acid, malic acid, succinic acid, acetic acid, fumaric acid, tartaric acid, citric acid, L-glutamic hydrochloride, and mixtures thereof; more preferably L- glutamic acid, lactic acid, citric acid.
  • Cationic amine surfactants included among those useful are disclosed in U.S. Patent 4,275,055, Nachtigal, et al., issued June 23, 1981 , which is incorporated by reference herein in its entirety.
  • the additional cationic surfactants for use herein may also include a plurality of ammonium quaternary moieties or amino moieties, or a mixture thereof.
  • Behentrimonium chloride commercially available under various tradenames, including GENAMIN KDM from Hoescht Celanese/Colorants & Surfactants; INCROQUAT TMC-80 and -95 from Croda, Inc., and VARISOFT BT- 185 from Witco, is useful herein.
  • Particularly suitable herein are the available behentrimonium chlorides pre-mixed with volatile solvents, for example lower alkyl alcohols having 1 to 3 carbons such as ethanol and isopropanol; nonvolatile solvents, for example alkyl alcohols having more than 3 carbons, and polyhydric alcohols such as 1 ,2-propane diol or propylene glycol, 1 ,3-propane diol, hexylene glycol, glycerin, diethylene glycol, dipropylene glycol, 1 ,2- butylene glycol, and 1 ,4-butylene glycol; and mixtures thereof.
  • volatile solvents for example lower alkyl alcohols having 1 to 3 carbons such as ethanol and isopropanol
  • nonvolatile solvents for example alkyl alcohols having more than 3 carbons
  • polyhydric alcohols such as 1 ,2-propane diol or propylene glycol, 1 ,3-propane diol, hex
  • compositions of the present invention comprise water.
  • the compositions herein are substantially free of organic solvents, for example other liquid, water-miscible or water-soluble solvents such as lower alkyl alcohols, e.g., C C 5 alkyl monohydric alcohols, and C 2 -C 3 alkyl alcohols.
  • organic solvents for example other liquid, water-miscible or water-soluble solvents such as lower alkyl alcohols, e.g., C C 5 alkyl monohydric alcohols, and C 2 -C 3 alkyl alcohols.
  • levels of up to about 5.0% by weight of the composition of such organic solvents are generally acceptable herein, since the component materials themselves may contain small amounts of such solvents.
  • the water useful herein includes deionized water and water from natural sources containing mineral cations. Deionized water is preferred. ADDITIONAL CONDITIONING AGENTS
  • compositions of the present invention may further comprise by weight from about 0.01 % to about 20.0%, preferably from about 1.0% to about 15.0%, and more preferably from about 2.0% to about 10.0%, of additional conditioning agents.
  • additional conditioning agents useful herein include oily compounds, cationic polymers, silicone compounds, and nonionic polymers.
  • compositions of the present invention may additionally comprise an oily compound having a melting point of not more than about 25°C selected from the group consisting of a first oily compound, a second oily compound, and mixtures thereof.
  • the oily compounds useful herein may be volatile or nonvolatile. Without being bound by theory, it is believed that, the oily compounds may penetrate the hair to modify the hydroxy bonds of the hair, thereby resulting in providing softness and flexibility to the hair.
  • the oily compound may comprise either the first oily compound or the second oily compound as described herein. Preferably, a mixture of the first oily compound and the second oily compound is used.
  • the oily compounds of this section are to be distinguished from the high melting point compounds described above. Nonlimiting examples of the oily compounds are found in International Cosmetic Ingredient Dictionary, Fifth Edition, 1993, and CTFA Cosmetic Ingredient Handbook, Second Edition, 1992, both of which are incorporated by reference herein in their entirety.
  • the fatty alcohols useful herein include those having from about 10 to about 30 carbon atoms, preferably from about 12 to about 22 carbon atoms, and more preferably from about 16 to about 22 carbon atoms. These fatty alcohols can be straight or branched chain alcohols and can be saturated or unsaturated alcohols, preferably unsaturated alcohols. Nonlimiting examples of these compounds include oleyl alcohol, palmitoleic alcohol, isostearyl alcohol, isocetyl alchol, undecanol, octyl dodecanol, octyl decanol, octyl alcohol, caprylic alcohol, decyl alcohol and lauryl alcohol.
  • the fatty acids useful herein include those having from about 10 to about 30 carbon atoms, preferably from about 12 to about 22 carbon atoms, and more preferably from about 16 to about 22 carbon atoms. These fatty acids can be straight or branched chain acids and can be saturated or unsaturated. Suitable fatty acids include, for example, oleic acid, linoleic acid, isostearic acid, linolenic acid, ethyl linolenic acid, ethyl linolenic acid, arachidonic acid, and ricinolic acid.
  • the fatty acid derivatives and fatty alcohol derivatives are defined herein to include, for example, esters of fatty alcohols, alkoxylated fatty alcohols, alkyl ethers of fatty alcohols, alkyl ethers of alkoxylated fatty alcohols, and mixtures thereof.
  • Nonlimiting examples of fatty acid derivatives and fatty alcohol derivatives include, for example, methyl linoleate, ethyl linoleate, isopropyl linoleate, isodecyl oleate, isopropyl oleate, ethyl oleate, octyldodecyl oleate, oleyl oleate, decyl oleate, butyl oleate, methyl oleate, octyldodecyl stearate, octyldodecyl isostearate, octyldodecyl isopalmitate, octyl isopelargonate, octyl pelargonate, hexyl isostearate, isopropyl isostearate, isodecyl isononanoate, Oleth-2, pentaeryth
  • first oily compounds useful herein include: oleyl alcohol with tradename UNJECOL 90BHR available from New Japan Chemical, pentaerythritol tetraisostearate and trimethylolpropane triisostearate with tradenames KAKPTI and KAKTTI available from Kokyu Alcohol (Chiba, Japan), pentaerythritol tetraoleate having the same tradename as the compound name available from New Japan Chemical, trimethylolpropane trioleate with a tradename ENUJERUBU series available from New Japan Chemical, various liquid esters with tradenames SCHERCEMOL series available from Scher, and hexyl isostearate with a tradename HIS and isopropryl isostearate having a tradename ZPIS available from Kokyu Alcohol.
  • the second oily compounds useful herein include straight chain, cyclic, and branched chain hydrocarbons which can be either saturated or unsaturated, so long as they have a melting point of not more than about 25°C. These hydrocarbons have from about 12 to about 40 carbon atoms, preferably from about 12 to about 30 carbon atoms, and preferably from about 12 to about 22 carbon atoms. Also encompassed herein are polymeric hydrocarbons of alkenyl monomers, such as polymers of C2-6 alkenyl monomers. These polymers can be straight or branched chain polymers. The straight chain polymers will typically be relatively short in length, having a total number of carbon atoms as described above. The branched chain polymers can have substantially higher chain lengths.
  • the number average molecular weight of such materials can vary widely, but will typically be up to about 500, preferably from about 200 to about 400, and more preferably from about 300 to about 350.
  • mineral oils are liquid mixtures of hydrocarbons that are obtained from petroleum. Specific examples of suitable hydrocarbon materials include paraffin oil, mineral oil, dodecane, isododecane, hexadecane, isohexadecane, eicosene, isoeicosene, tridecane, tetradecane, polybutene, polyisobutene, and mixtures thereof.
  • hydrocarbons selected from the group consisting of mineral oil, isododecane, isohexadecane, polybutene, polyisobutene, and mixtures thereof.
  • second oily compounds useful herein include isododecane, isohexadeance, and isoeicosene with tradenames PERMETHYL 99A, PERMETHYL 101 A, and PERMETHYL 1082, available from Presperse (South Plainfield New Jersey, USA), a copolymer of isobutene and normal butene with tradenames INDOPOL H-100 available from Amoco Chemicals (Chicago Illinois, USA), mineral oil with tradename BENOL available from Witco, isoparafl ⁇ n with tradename ISOPAR from Exxon Chemical Co.
  • polymer shall include materials whether made by polymerization of one type of monomer or made by two (i.e., copolymers) or more types of monomers.
  • the cationic polymer is a water-soluble cationic polymer.
  • water soluble cationic polymer what is meant is a polymer which is sufficiently soluble in water to form a substantially clear solution to the naked eye at a concentration of 0.1 % in water (distilled or equivalent) at 25°C.
  • the preferred polymer will be sufficiently soluble to form a substantially clear solution at 0.5% concentration, more preferably at 1.0% concentration.
  • the cationic polymers hereof will generally have a weight average molecular weight which is at least about 5,000, typically at least about 10,000, and is less than about 10 million. Preferably, the molecular weight is from about 100,000 to about 2 million.
  • the cationic polymers will generally have cationic nitrogen-containing moieties such as quaternary ammonium or cationic amino moieties, and mixtures thereof.
  • the cationic charge density is preferably at least about 0.1 meq/gram, more preferably at least about 1.5 meq/gram, even more preferably at least about 1.1 meq/gram, still more preferably at least about 1.2 meq/gram.
  • Cationic charge density of the cationic polymer can be determined according to the Kjeldahl Method. Those skilled in the art will recognize that the charge density of amino-containing polymers may vary depending upon pH and the isoelectric point of the amino groups. The charge density should be within the above limits at the pH of intended use.
  • Any anionic counterions can be utilized for the cationic polymers so long as the water solubility criteria is met.
  • Suitable counterions include halides (e.g., Cl, Br, I, or F, preferably Cl, Br, or I), sulfate, and methylsulfate. Others can also be used, as this list is not exclusive.
  • the cationic nitrogen-containing moiety will be present generally as a substituent, on a fraction of the total monomer units of the cationic hair conditioning polymers.
  • the cationic polymer can comprise copolymers, terpolymers, etc. of quaternary ammonium or cationic amine-substituted monomer units and other non-cationic units referred to herein as spacer monomer units.
  • Such polymers are known in the art, and a variety can be found in the CTFA Cosmetic Ingredient Dictionary, 3rd edition, edited by Estrin, Crosley, and Haynes, (The Cosmetic, Toiletry, and Fragrance Association, Inc., Washington, D.C., 1982).
  • Suitable cationic polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functionalities with water soluble spacer monomers such as acrylamide, methacrylamide, alkyl and dialkyi acrylamides, alkyl and dialkyi methacrylamides, alkyl acrylate, alkyl methacrylate, vinyl caprolactone, and vinyl pyrrolidone.
  • the alkyl and dialkyi substituted monomers preferably have C-
  • Other suitable spacer monomers include vinyl esters, vinyl alcohol (made by hydrolysis of polyvinyl acetate), maleic anhydride, propylene glycol, and ethylene glycol.
  • the cationic amines can be primary, secondary, or tertiary amines, depending upon the particular species and the pH of the composition. In general, secondary and tertiary amines, especially tertiary amines, are preferred.
  • Amine-substituted vinyl monomers can be polymerized in the amine form, and then optionally can be converted to ammonium by a quaternization reaction. Amines can also be similarly quaternized subsequent to formation of the polymer.
  • tertiary amine functionalities can be quaternized by reaction with a salt of the formula R'X wherein R' is a short chain alkyl, preferably a C-
  • Suitable cationic amino and quaternary ammonium monomers include, for example, vinyl compounds substituted with dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate, monoalkylaminoalkyl acrylate, monoalkylaminoalkyl methacrylate, trialkyl methacryloxyalkyl ammonium salt, trialkyl acryloxyalkyl ammonium salt, diallyl quaternary ammonium salts, and vinyl quaternary ammonium monomers having cyclic cationic nitrogen-containing rings such as pyridinium, imidazolium, and quaternized pyrrolidone, e.g., alkyl vinyl imidazolium, alkyl vinyl pyridinium, alkyl vinyl pyrrolidone salts.
  • the alkyl portions of these monomers are preferably lower alkyls such as the C-
  • Suitable amine-substituted vinyl monomers for use herein include dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate, dialkylaminoalkyl acrylamide, and dialkylaminoalkyl methacrylamide, wherein the alkyl groups are preferably C-
  • the cationic polymers hereof can comprise mixtures of monomer units derived from amine- and/or quaternary ammonium-substituted monomer and/or compatible spacer monomers.
  • Suitable cationic hair conditioning polymers include, for example: copolymers of 1-vinyl-2-pyrrolidone and 1-vinyl-3-methylimidazolium salt (e.g., chloride salt) (referred to in the industry by the Cosmetic, Toiletry, and Fragrance Association, "CTFA", as Polyquaternium-16), such as those commercially available from BASF Wyandotte Corp.
  • CTFA Cosmetic, Toiletry, and Fragrance Association
  • cationic polymers that can be used include polysaccharide polymers, such as cationic cellulose derivatives and cationic starch derivatives.
  • Cationic polysaccharide polymer materials suitable for use herein include those of the formula: wherein: A is an anhydroglucose residual group, such as a starch or cellulose anhydroglucose residual, R is an alkylene oxyalkylene, polyoxyalkylene, or hydroxyalkylene group, or combination thereof, R1 , R 2 , and R 3 independently are alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, or alkoxyaryl groups, each group containing up to about 18 carbon atoms, and the total number of carbon atoms for each cationic moiety (i.e., the sum of carbon atoms in R1 , R 2 and R 3 ) preferably being about 20 or less, and X is an anionic counterion, as previously described.
  • A is an anhydroglucose residual group, such as a starch or cellulose anhydroglucose residual
  • R is an alkylene oxyal
  • Cationic cellulose is available from Amerchol Corp. (Edison, NJ, USA) in their Polymer JR® and LR® series of polymers, as salts of hydroxyethyl cellulose reacted with trimethyl ammonium substituted epoxide, referred to in the industry (CTFA) as Polyquaternium 10.
  • CTFA trimethyl ammonium substituted epoxide
  • Another type of cationic cellulose includes the polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryl dimethyl ammonium-substituted epoxide, referred to in the industry (CTFA) as Polyquaternium 24. These materials are available from Amerchol Corp. (Edison, NJ, USA) under the tradename Polymer LM-200®.
  • cationic polymers that can be used include cationic guar gum derivatives, such as guar hydroxypropyltrimonium chloride (commercially available from Celanese Corp. in their Jaguar R series).
  • Other materials include quaternary nitrogen-containing cellulose ethers (e.g., as described in U.S. Patent 3,962,418, incorporated herein by reference), and copolymers of etherified cellulose and starch (e.g., as described in U.S. Patent 3,958,581 , incorporated herein by reference.) Silicone Compounds
  • the additional conditioning agents useful herein include silicone compounds.
  • the silicone compounds hereof can include volatile soluble or insoluble, or nonvolatile soluble or insoluble silicone conditioning agents.
  • soluble what is meant is that the silicone compound is miscible with the carrier of the composition so as to form part of the same phase.
  • insoluble what is meant is that the silicone forms a separate, discontinuous phase from the carrier, such as in the form of an emulsion or a suspension of droplets of the silicone.
  • Suitable silicone fluids include polyalkyl siloxanes, polyaryl siloxanes, cyclic siloxanes, polyalkylaryl siloxanes, polyether siloxane copolymers, and mixtures thereof.
  • Other nonvolatile silicone compounds having hair conditioning properties can also be used.
  • the silicone compounds herein also include polyalkyl or polyaryl siloxanes with the following structure (I):
  • R R R R wherein R is alkyl or aryl, and x is an integer from about 7 to about 8,000.
  • "A" represents groups which block the ends of the silicone chains.
  • the alkyl or aryl groups substituted on the siloxane chain (R) or at the ends of the siloxane chains (A) can have any structure as long as the resulting silicone remains fluid at room temperature, is dispersible, is neither irritating, toxic nor otherwise harmful when applied to the hair, is compatible with the other components of the composition, is chemically stable under normal use and storage conditions, and is capable of being deposited on and conditions the hair.
  • Suitable A groups include hydroxy, methyl, methoxy, ethoxy, propoxy, and aryloxy.
  • the two R groups on the silicon atom may represent the same group or different groups.
  • the two R groups represent the same group.
  • Suitable R groups include methyl, ethyl, propyl, phenyl, methylphenyl and phenylmethyl.
  • the preferred silicone compounds are polydimethylsiloxane, polydiethylsiloxane, and polymethylphenylsiloxane. Polydimethylsiloxane, which is also known as dimethicone, is especially preferred.
  • the polyalkylsiloxanes that can be used include, for example, polydimethylsiloxanes. These silicone compounds are available, for example, from the General Electric Company in their ViscasilR and SF 96 series, and from Dow Corning in their Dow Corning 200 series.
  • Cyclic siloxanes herein include cyclomethicone with the following structure (II): wherein n is an integer having a value of from 3 to 10.
  • the cyclomethicone may be a single species, or a combination of two or more species.
  • These cyclomethicones are available, for example, from Rh ⁇ ne-Poulenc as SILIBIONE OILS 70045, 70045 V2, 70045 V3, and 70045 V5; or from Wacker Silicones as SILOXANE F-222, F-223, F-250, F-251 , SWS-03314, or SWS-03400.
  • Polyalkylaryl siloxane fluids can also be used and include, for example, polymethylphenylsiloxanes. These siloxanes are available, for example, from the General Electric Company as SF 1075 methyl phenyl fluid or from Dow Corning as 556 Cosmetic Grade Fluid.
  • highly arylated silicone compounds such as highly phenylated polyethyl silicone having refractive index of about 1.46 or higher, especially about 1.52 or higher.
  • a spreading agent such as a surfactant or a silicone resin, as described below to decrease the surface tension and enhance the film forming ability of the material.
  • the silicone compounds that can be used include, for example, a polypropylene oxide modified polydimethylsiloxane although ethylene oxide or mixtures of ethylene oxide and propylene oxide can also be used.
  • the ethylene oxide and polypropylene oxide level should be sufficiently low so as not to interfere with the dispersibility characteristics of the silicone.
  • These material are also known as dimethicone copolyols.
  • Other silicone compounds include amino substituted materials.
  • Suitable alkylamino substituted silicone compounds include those represented by the following structure (III): wherein R is CH3 or OH, x and y are integers which depend on the molecular weight, the average molecular weight being approximately between 5,000 and 10,000, and a and b are integers from 1 to 5. This polymer is also known as "amodimethicone.”
  • Suitable amino substituted silicone fluids include those represented by the formula (IV):
  • R2 is chosen from the group consisting of hydrogen, phenyl, benzyl, a saturated hydrocarbon radical, preferably an alkyl radical containing from 1 to 20 carbon atoms, and A " denotes a halide ion.
  • n and m are selected depending on the exact molecular weight of the compound desired, and a and b are integers from 1 to 5.
  • R 3 denotes a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, preferably an alkyl or alkenyl radical such as methyl
  • R4 denotes a hydrocarbon radical, preferably a C-
  • Q " is a halide ion, preferably chloride
  • r denotes an average statistical value from 2 to 20, preferably from 2 to 8
  • s denotes an average statistical value from 20 to 200, and preferably from 20 to 50.
  • a preferred polymer of this class is available from Union Carbide under the name "UCAR SILICONE ALE 56.”
  • references disclosing suitable nonvolatile dispersed silicone compounds include U.S. Patent No. 2,826,551 , to Geen; U.S. Patent No. 3,964,500, to Drakoff, issued June 22, 1976; U.S. Patent No. 4,364,837, to Pader; and British Patent No. 849,433, to Woolston, all of which are incorporated herein by reference in their entirety. Also incorporated herein by reference in its entirety is "Silicon Compounds" distributed by Petrarch Systems, Inc., 1984. This reference provides an extensive, though not exclusive, listing of suitable silicone compounds.
  • 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. Silicone gums are described by Petrarch, and others including U.S. Patent No. 4,152,416, to Spitzer et al., issued May 1 , 1979 and Noll, Walter, Chemistry and Technology of Silicones, New York: Academic Press 1968.
  • 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. Specific examples include polydimethylsiloxane, polydimethylsiloxane methylvinylsiloxane) copolymer, polydimethylsiloxane diphenylsiloxane methylvinylsiloxane) copolymer and mixtures thereof. Also useful are silicone resins, which are highly crosslinked polymeric siloxane systems.
  • the crossiinking is introduced through the incorporation of tri- functional and tetra-functional silanes with mono-functional or di-functional, or both, silanes during manufacture of the silicone resin.
  • the degree of crossiinking that is required in order to result in a silicone resin will vary according to the specific silane units incorporated into the silicone resin.
  • silicone materials which have a sufficient level of trifunctional and tetrafunctional siloxane monomer units, and hence, a sufficient level of crossiinking, such that they dry down to a rigid, or hard, film are considered to be silicone resins.
  • the ratio of oxygen atoms to silicon atoms is indicative of the level of crossiinking in a particular silicone material.
  • Silicone materials which have at least about 1.1 oxygen atoms per silicon atom will generally be silicone resins herein. Preferably, the ratio of oxygen:silicon atoms is at least about 1.2:1.0.
  • Silanes used in the manufacture of silicone resins include monomethyl-, dimethyl-, trimethyl-, monophenyl-, diphenyl-, methylphenyl-, monovinyl-, and methylvinylchlorosilanes, and tetrachlorosilane, with the methyl substituted silanes being most commonly utilized.
  • Preferred resins are offered by General Electric as GE SS4230 and SS4267.
  • silicone resins will generally be supplied in a dissolved form in a low viscosity volatile or nonvolatile silicone fluid.
  • the silicone resins for use herein should be supplied and incorporated into the present compositions in such dissolved form, as will be readily apparent to those skilled in the art. Without being bound by theory, it is believed that the silicone resins can enhance deposition of other silicone compounds on the hair and can enhance the glossiness of hair with high refractive index volumes.
  • Other useful silicone resins are silicone resin powders such as the material given the CTFA designation polymethylsilsequioxane, which is commercially available as Tospear.T from Toshiba Silicones.
  • Silicone materials and silicone resins in particular can conveniently be identified according to a shorthand nomenclature system well known to those skilled in the art as the "MDTQ" nomenclature. Under this system, the silicone is described according to the presence of various siloxane monomer units which make up the silicone.
  • M denotes the mono-functional unit ( H3)3SiO) 5
  • D denotes the difunctional unit (CH3)2SiO
  • T denotes the trifunctional unit (CH3)SiO ⁇ 5
  • Q denotes the quadri- or tetra-functional unit Si ⁇ 2-
  • Typical alternate substituents include groups such as vinyl, phenyl, amino, hydroxyl, etc.
  • the molar ratios of the various units either in terms of subscripts to the symbols indicating the total number of each type of unit in the silicone, or an average thereof, or as specifically indicated ratios in combination with molecular weight, complete the description of the silicone material under the MDTQ system.
  • Higher relative molar amounts of T, Q, T and/or Q' to D, D', M and/or or M' in a silicone resin is indicative of higher levels of crossiinking.
  • the overall level of crossiinking can also be indicated by the oxygen to silicon ratio.
  • the silicone resins for use herein which are preferred are MQ, MT, MTQ,
  • Nonionic Polymer include cellulose derivatives, hydrophobically modified cellulose derivatives, ethylene oxide polymers, and ethylene oxide/propylene oxide based polymers.
  • Suitable nonionic polymers are cellulose derivatives including methylcellulose with tradename BENECEL, hydroxyethyl cellulose with tradename NATROSOL, hydroxypropyl cellulose with tradename KLUCEL, cetyl hydroxyethyl cellulose with tradename POLYSURF 67, all supplied by Herculus.
  • Other suitable nonionic polymers are ethylene oxide and/or propylene oxide based polymers with tradenames CARBOWAX PEGs, POLYOX WASRs, and UCON FLUIDS, all supplied by Amerchol.
  • Polvalkylene Glycols are examples of polyethylene oxide and/or propylene oxide based polymers with tradenames CARBOWAX PEGs, POLYOX WASRs, and UCON FLUIDS, all supplied by Amerchol.
  • the polyalkylene glycol is typically used at a level from about 0.025% to about 1.5%, preferably from about 0.05% to about 1%, and more preferably from about 0.1% to about 0.5% of the compositions.
  • R is selected from the group consisting of H, methyl, and mixtures thereof.
  • these materials are polymers of ethylene oxide, which are also known as polyethylene oxides, polyoxyethylenes, and polyethylene glycols.
  • R is methyl these materials are polymers of propylene oxide, which are also known as polypropylene oxides, polyoxypropylenes, and polypropylene glycols.
  • R is methyl it is also understood that various positional isomers of the resulting polymers can exist.
  • n has an average value of from about 1500 to about 25,000, preferably from about 2500 to about 20,000, and more preferably from about 3500 to about 15,000.
  • Polyethylene glycol polymers useful herein are PEG-2M wherein R equals
  • H and n has an average value of about 2,000 (PEG-2M is also known as Polyox WSR® N-10, which is available from Union Carbide and as PEG-2,000); PEG- 5M wherein R equals H and n has an average value of about 5,000 (PEG-5M is also known as Polyox WSR® N-35 and Polyox WSR® N-80, both available from Union Carbide and as PEG-5,000 and Polyethylene Glycol 300,000); PEG-7M wherein R equals H and n has an average value of about 7,000 (PEG-7M is also known as Polyox WSR® N-750 available from Union Carbide); PEG-9M wherein R equals H and n has an average value of about 9,000 (PEG 9-M is also known as Polyox WSR® N-3333 available from Union Carbide); and PEG-14 M wherein R equals H and n has an average value of about 14,000 (PEG-14M is also known as Polyox WSR® N-3000 available from
  • compositions 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 compositions more cosmetically or aesthetically acceptable or to provide them with additional usage benefits.
  • additional components generally are used individually at levels from about 0.001% to about 10.0%, preferably from about 0.01% to about 5.0% by weight of the composition.
  • a wide variety of other additional ingredients can be formulated into the present compositions. These include: other conditioning agents such as hydrolysed collagen with tradename 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; hair-fixative polymers such as amphoteric fixative polymers, cationic fixative polymers, anionic fixative polymers, nonionic fixative polymers, and silicone grafted copolymers; 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; salts, in general, such as potassium acetate and sodium chloride; coloring agents, such as any of the FD&C or D&C dyes;
  • a suitable method for making the compositions of the present invention comprises the steps of first mixing the hydrophilically substituted cationic surfactant and water at a temperature above about 60°C, followed by addition of high melting point compounds while maintaining the temperature above about 60 °C, cooling, and finally adding remaining components including heat-sensitive components.
  • the embodiments disclosed and represented by the previous examples have many advantages. For example, they can provide high levels of conditioning agents without causing an unacceptably high increase in the viscosity of the composition. They can further provide improved conditioning benefits, including wet and dry combing benefits and good feel when the hair is wet.

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Abstract

Cette invention concerne une composition capillaire renfermant les composés suivants: (a) un tensioactif cationique hydrophiliquement substitué; (b) environ 5 % à environ 20 % en poids d'un composé à point de fusion élevé; (c) un tensioactif cationique supplémentaire; et (d) de l'eau. Dans cette composition, β/α est inférieur à 4000, α étant le pourcentage en poids du composé à point de fusion élevé et β la viscosité (cps) de la composition à un taux de cisaillement constant de 2 sec. -1 au bout d'une minute, avec β inférieur à 35000 cps.
PCT/US1997/020736 1997-09-17 1997-11-12 Compositions pour traitement capillaire comprenant des tensioactifs cationiques hydrophiliquement substitues et des composes a point de fusion eleve WO1999024014A1 (fr)

Priority Applications (18)

Application Number Priority Date Filing Date Title
BR9714976-4A BR9714976A (pt) 1997-11-12 1997-11-12 "composição de condicionamento do cabelo"
PCT/US1997/020736 WO1999024014A1 (fr) 1997-11-12 1997-11-12 Compositions pour traitement capillaire comprenant des tensioactifs cationiques hydrophiliquement substitues et des composes a point de fusion eleve
JP11507088A JP2000513382A (ja) 1997-11-12 1997-11-12 親水的に置換されたカチオン性界面活性剤および高融点化合物を含有するヘアコンディショニング組成物
EP97949420A EP1032365A1 (fr) 1997-11-12 1997-11-12 Compositions pour traitement capillaire comprenant des tensioactifs cationiques hydrophiliquement substitues et des composes a point de fusion eleve
AU27041/99A AU2704199A (en) 1997-11-12 1997-11-12 Hair conditioning compositions comprising hydrophilically substituted cationi c surfactants and high melting point compounds
CA002304275A CA2304275C (fr) 1997-09-17 1998-06-04 Produit capillaire a base d'esters huiles a haute densite moleculaire
HU0100622A HUP0100622A3 (en) 1997-09-17 1998-06-04 Hair conditioning composition comprising high molecular weight ester oil
KR1020007002882A KR20010024125A (ko) 1997-09-17 1998-06-04 고분자량 에스테르 오일을 함유하는 모발 콘디쇼닝 조성물
EP98926401A EP1014919A1 (fr) 1997-09-17 1998-06-04 Produit capillaire a base d'esters huiles
CN98811244A CN1279600A (zh) 1997-09-17 1998-06-04 包含高分子量酯油的头发调理组合物
AU78247/98A AU7824798A (en) 1997-09-17 1998-06-04 Hair conditioning composition comprising high molecular weight ester oil
TR2000/01027T TR200001027T2 (tr) 1997-09-17 1998-06-04 Yüksek molaküler ağırlıklı ester yağı içeren saç şekillendiricisi karışımları.
BR9812347-5A BR9812347A (pt) 1997-09-17 1998-06-04 "composição para condicionamento do cabelo"
IL13503798A IL135037A0 (en) 1997-09-17 1998-06-04 Hair conditioning composition comprising high molecular weight ester oil
IDW20000711D ID24697A (id) 1997-09-17 1998-06-04 Komposisi pengkondisi rambut yang terdiri dari minyak ester berat molekul tinggi
PL98339367A PL339367A1 (en) 1997-09-17 1998-06-04 Hair nutrient containing high-molecular ester of oily nature
PCT/US1998/011781 WO1999013838A1 (fr) 1997-09-17 1998-06-04 Produit capillaire a base d'esters huiles
NO20001352A NO20001352L (no) 1997-09-17 2000-03-15 HÕrkondisjoneringsblanding omfattende esterolje med høy molekylvekt

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PCT/US1997/020736 WO1999024014A1 (fr) 1997-11-12 1997-11-12 Compositions pour traitement capillaire comprenant des tensioactifs cationiques hydrophiliquement substitues et des composes a point de fusion eleve

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Publication number Priority date Publication date Assignee Title
WO2001017492A1 (fr) * 1999-09-03 2001-03-15 The Procter & Gamble Company Procede de formation d'une composition de soins capillaires et composition ainsi obtenue
WO2002022089A1 (fr) * 2000-09-13 2002-03-21 The Procter & Gamble Company Composition revitalisante concentree
EP2418003A3 (fr) * 2010-07-23 2016-02-24 Henkel AG & Co. KGaA Composition de décoloration des cheveux contenant un sel d'ammonium
CN115023214A (zh) * 2020-01-15 2022-09-06 联合利华知识产权控股有限公司 毛发护理组合物

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JP2002293719A (ja) * 2001-03-29 2002-10-09 Asahi Denka Kogyo Kk 毛髪処理剤組成物

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WO1990010429A1 (fr) * 1989-03-13 1990-09-20 S.C. Johnson & Son, Inc. Composition de soins personnels se presentant sous forme de perles brillantes
WO1992010163A1 (fr) * 1990-12-05 1992-06-25 The Procter & Gamble Company Compositions de shampooing a base de silicones et d'agents conditionneurs tensioactifs cationiques
WO1993010746A1 (fr) * 1991-11-25 1993-06-10 Stepan Co Agents de suspension destines a des elements insolubles de compositions de nettoyage, formes par la reaction de sels d'ammonium alkyle avec des tensioactifs anioniques

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Publication number Priority date Publication date Assignee Title
WO1990010429A1 (fr) * 1989-03-13 1990-09-20 S.C. Johnson & Son, Inc. Composition de soins personnels se presentant sous forme de perles brillantes
WO1992010163A1 (fr) * 1990-12-05 1992-06-25 The Procter & Gamble Company Compositions de shampooing a base de silicones et d'agents conditionneurs tensioactifs cationiques
WO1993010746A1 (fr) * 1991-11-25 1993-06-10 Stepan Co Agents de suspension destines a des elements insolubles de compositions de nettoyage, formes par la reaction de sels d'ammonium alkyle avec des tensioactifs anioniques

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001017492A1 (fr) * 1999-09-03 2001-03-15 The Procter & Gamble Company Procede de formation d'une composition de soins capillaires et composition ainsi obtenue
WO2002022089A1 (fr) * 2000-09-13 2002-03-21 The Procter & Gamble Company Composition revitalisante concentree
EP2418003A3 (fr) * 2010-07-23 2016-02-24 Henkel AG & Co. KGaA Composition de décoloration des cheveux contenant un sel d'ammonium
CN115023214A (zh) * 2020-01-15 2022-09-06 联合利华知识产权控股有限公司 毛发护理组合物
US20230063524A1 (en) * 2020-01-15 2023-03-02 Conopco, Inc., D/B/A Unilever Hair care composition

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