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WO2004026269A1 - Produit de soin capillaire a effet fixateur - Google Patents

Produit de soin capillaire a effet fixateur Download PDF

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Publication number
WO2004026269A1
WO2004026269A1 PCT/EP2003/009939 EP0309939W WO2004026269A1 WO 2004026269 A1 WO2004026269 A1 WO 2004026269A1 EP 0309939 W EP0309939 W EP 0309939W WO 2004026269 A1 WO2004026269 A1 WO 2004026269A1
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Prior art keywords
hair
acrylate
polymer
hair treatment
treatment composition
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
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PCT/EP2003/009939
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German (de)
English (en)
Inventor
Konstanze Mayer
Peter Schmiedel
Michael Heyer
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority to AU2003264277A priority Critical patent/AU2003264277A1/en
Publication of WO2004026269A1 publication Critical patent/WO2004026269A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
    • A61K8/044—Suspensions
    • 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
    • A61K8/18—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
    • A61K8/817—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers

Definitions

  • the present invention relates to the use of nonionic, crosslinked (meth) acrylate-containing polymers with an average particle diameter in the range from 50 to 500 nm for strengthening keratin fibers, and to hair treatment compositions which contain these polymers.
  • hairdressing agents such as hair fixers or hair sprays.
  • Hair setting agents are distributed in damp hair for styling, while hair sprays are sprayed onto the finished hairstyle for fixation.
  • agents are generally used which remain on the hair.
  • this entails the risk of an undesirable strain on the hair.
  • the setting active ingredients which are usually polymeric compounds, are generally used in the form of hair setting agents or hair sprays. However, it is also possible to incorporate them into conventional hair cleaners or conditioners.
  • German patent application DE 19949517.3 describes setting hair cleansing agents in the form of an aqueous preparation which contain a synergistic combination of a water-soluble foaming surfactant and a film-forming polymer dispersed therein, which is a copolymer of quat.-ammonium-substituted acrylates.
  • the German patent application DE 4414424.5 describes hair treatment agents with good rewashability.
  • the compositions contain an aqueous dispersion of an insoluble polymer, the polymer having a glass transition temperature between -20 and + 70 ° C and being essentially formed from monomers which are selected from esters of acrylic acid, esters of methacrylic acid and styrene.
  • the hair treatment compositions also contain a water-soluble polymer.
  • European patent application EP-A2 0288012 describes hair cosmetic compositions which contain fine particles of a crosslinked polymer.
  • the polymer is derived from a monofunctional oil-soluble monomer, the polymerization product of which has a glass transition temperature of up to 300 ° K.
  • the polymer is still insoluble in water and ethanol and does not form a film at normal temperature.
  • the hair-setting active ingredients known from the prior art often no longer have sufficient effects in high ambient humidity. They can also strain the hair, especially when used in the form of a leave-on formulation, or change its feel or shine in an undesirable manner.
  • the applicability of the known hair-setting active ingredients is restricted by their solubilities or dispersibility in the corresponding hair treatment compositions and by their compatibility with the other formulation components contained therein.
  • the combination of the cationic polymers widely used as hair-setting active ingredients with anionic formulation components can lead to undesirable precipitation.
  • the present invention was based on the object of providing hair treatment compositions for strengthening keratin fibers are suitable and have advantages over the hair-setting agents known from the prior art which have a hair-setting effect.
  • nonionic, crosslinked (meth) acrylate-containing polymers with an average particle diameter in the range from 50 to 500 nm can meet these requirements in an outstanding manner and can bring about a significant strengthening of keratin fibers.
  • a first subject of the invention is therefore the use of a non-ionic, cross-linked (meth) acrylate-containing polymer with an average particle diameter in the range from 50 to 500 nm for the strengthening of keratin fibers.
  • keratin fibers are to be understood as meaning furs, wool, feathers, hair and in particular human hair.
  • the invention further relates to a hair treatment composition which, in addition to conventional cosmetic constituents, furthermore contains a dispersion of a nonionic, crosslinked (meth) acrylate-containing polymer with an average particle diameter in the range from 50 to 500 nm.
  • a crosslinked (meth) acrylate-containing polymer is to be understood as a crosslinked homopolymer or copolymer which is based on two or more monomers, including the crosslinker. At least one of these monomers must be polyfunctional in order to effect crosslinking. Including the crosslinker, according to the invention at least one of the monomers must furthermore be a derivative of acrylic acid or methacrylic acid, derivative being understood to mean in particular an ester or an amide.
  • Monomers for the polymers used according to the invention are monounsaturated polymerizable compounds, preferably the esters and amides of acrylic acid and methacrylic acid and vinylpyrrolidone.
  • esters and amides with alcohols or amines having 1 to 6 carbon atoms are preferred, it being possible for the alcohols or amines to be additionally substituted with 1 to 3 hydroxyl groups.
  • N-vinylpyrrolidone the following are particularly suitable as monomers: methyl acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate, tert-butyl acrylate, sec-butyl acrylate, n-hexyl acrylate, n-octyl acrylate, 2-ethylhexyl acrylate, n-dodecyl acrylate, 2-hydroxyl acrylate, 2-hydroxyl acrylate Isopropylacrylamide and the corresponding methacrylic acid derivatives.
  • Polymers which are particularly preferred for the purposes of the invention are poly-N-isopropylacrylamide and N-vinylpyrrolidone / (meth) acrylic ester copolymers.
  • the weight ratio of the different monomers to one another is not subject to any particular restrictions.
  • crosslinking of the polymer required according to the invention can be carried out by means of a polyfunctional monomer such as, for example, N, N'-methylenebisacramide or 1-vinyl-3- (E) -ethylidene pyrrolidone.
  • a polyfunctional monomer such as, for example, N, N'-methylenebisacramide or 1-vinyl-3- (E) -ethylidene pyrrolidone.
  • Crosslinking with N, N ' - methylenebisacrylamide is preferred for the purposes of the invention.
  • the polymer is about 0.5 to about 20%, but preferably about 2 to about 10% and most preferably about 4 to about 6% cross-linked.
  • a degree of crosslinking of x% is understood to mean that for 100 parts by weight of the total monofunctional monomers on which the polymer is based, x parts by weight of the crosslinker, i.e. of the polyfunctional monomer or the mixture of polyfunctional monomers.
  • Nonionic crosslinked (meth) acrylate-containing polymers suitable according to the invention with an average particle diameter in the range from 50 to 500 nm are preferably obtainable by polymerizing the monomers on which the polymer is based with one another in an emulsion polymerization.
  • the cross-linking is expediently thereby causes a suitable amount of a polyfunctional monomer or crosslinking agent to be added to the monomer or monomer mixture to be polymerized.
  • the size of the polymer particles depends on the production process used and can be influenced, for example, by the use of emulsifiers and by the choice of the concentration of the reactants during the polymerization. Through simple routine experiments, the person skilled in the art can determine the suitable production conditions for a respectively selected combination of monomers in order to obtain polymer particles of the size suitable according to the invention.
  • Anionic surfactants such as sodium dodecyl sulfate or alkylaryl polyglycol ether sulfate sodium salt are suitable as emulsifiers for the preparation of the polymers used according to the invention by emulsion polymerization.
  • the polymers used according to the invention are preferably prepared by emulsion polymerization in water as the dispersant.
  • Any initiator suitable for such an emulsion polymerization can be used as the polymerization initiator, but water-soluble initiators such as potassium peroxodisulfate are preferably used.
  • the reaction mixture obtained in the emulsion polymerization can be further purified in a manner known per se.
  • dialysis can remove residual monomers
  • centrifugation, filtration, freeze-drying or spray-drying can reduce the water content to a desired level or keep the polymers in an anhydrous, unswollen state.
  • the crosslinked (meth) acrylate-containing polymers used according to the invention are nonionic, ie they are not anionic, cationic or zwitterionic. This means in particular that they are free of acidic groups, such as carboxylate groups, and that they are free of quaternary or basic groups such as mono-, di- or trialkylamino groups, which would give the cross-linked polymer per se or in acidic solution a cationic character.
  • the average particle size of the polymers suitable according to the invention is between 50 and 500 nm, the value being based on the average particle diameter in the longitudinal direction, i.e. in the direction of the greatest expansion of the particles.
  • the particle size was determined in the context of the invention by laser diffraction using the Mastersizer-RT device from Malvern.
  • the polymers suitable according to the invention preferably have a glass transition temperature of more than 30 ° C. and particularly preferably of more than 50 ° C.
  • a glass transition temperature of more than 30 ° C. and particularly preferably of more than 50 ° C.
  • the person skilled in the art can make the necessary preselection based on the known laws that exist between the glass transition temperatures of the respective homopolymers and the corresponding copolymers.
  • Suitable hair treatment agents according to the invention are all agents whose application to the hair of the user primarily or among other things would like to achieve a shaping or shape-maintaining effect on the hairstyle.
  • cleaning agents such as shampoos, setting agents such as hair fixers, hair sprays and hair dryers, permanent shaping agents such as permanent wave and fixing agents, care agents such as conditioners, hair treatments and hair rinses, color-changing agents such as bleaching agents, oxidation dyes and toning agents based on direct dyes, Trade hair lotions and hair tip fluids.
  • the preparations can be formulated as solutions, emulsions, gels, creams, aerosols or lotions.
  • the hair treatment compositions according to the invention can be both rinse-off and products left on the hair. Rinse-off hair treatment agents are a preferred embodiment of the invention.
  • Hair treatment compositions which are particularly preferred according to the invention are hair shampoos.
  • the hair treatment compositions according to the invention contain the nonionic, crosslinked (meth) acrylate-containing polymer with an average particle diameter in the range from 50 to 500 nm in amounts of preferably about 0.01 to about 10, in particular about 0.05 to about 5, and particularly preferably about 0 , 1 to about 1 wt .-%, each based on the total weight of the agent.
  • the agents according to the invention contain at least one surfactant, particularly preferably an anionic surfactant.
  • surfactants is understood to mean surface-active substances which carry an anionic or cationic charge in the molecule. Both an anionic and a cationic charge can also be present in the molecule. These zwitterionic or amphoteric surface-active substances can also be used according to the invention. Furthermore, the surface-active substances can also be non-ionic.
  • Suitable anionic surfactants in agents according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 8 to 30 carbon atoms.
  • anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 8 to 30 carbon atoms.
  • glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups can be contained in the molecule.
  • suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium and the mono-, di- and triaikanolammonium salts with 2 to 4 carbon atoms in the alkanol group,
  • Alkyl sulfates and alkyl polyglycol ether sulfates of the formula R-0 (CH 2 -CH 2 0) x - OSO 3 H, in which R is a preferably linear alkyl group with 8 to 30 C atoms and x 0 or 1 to 12,
  • Esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols having 8 to 22 carbon atoms,
  • OX in R 1 is preferred for an aliphatic hydrocarbon radical with 8 to 30
  • R 2 for hydrogen, a radical (CH 2 CH 2 0) n R 1 or X, n for
  • sulfated fatty acid alkylene glycol esters of the formula (II) R 7 CO (AlkO) n SO 3 M (II) in which R 7 CO- for a linear or branched, aliphatic, saturated and / or unsaturated acyl radical having 6 to 22 carbon atoms, Alk for CH 2 CH 2 , CHCH3CH2 and / or CH 2 CHCH 3 , n for numbers of 0, 5 to 5 and M represents a cation as described in DE-OS 197 36 906.5, - monoglyceride sulfates and monoglyceride ether sulfates of the formula (III),
  • CH2 ⁇ (CH2CH2 ⁇ ) z - SO3X in R 8 CO for a linear or branched acyl radical having 6 to 22 carbon atoms, x, y and z in total for 0 or for numbers from 1 to 30, preferably 2 to 10, and X for a Alkali or alkaline earth metal stands.
  • Typical examples of monoglyceride (ether) sulfates suitable for the purposes of the invention are the reaction products of lauric acid monoglyceride, coconut fatty acid monoglyceride, palmitic acid monoglyceride, stearic acid monoglyceride, oleic acid monoglyceride and tallow fatty acid monoglyceride as well as their ethylene oxide adducts or their formulated with sulfuric acid trioxide.
  • Monoglyceride sulfates of the formula (III) are preferably used in which R 8 CO represents a linear acyl radical having 8 to 18 carbon atoms.
  • Monoglyceride sulfates and monoglyceride ether sulfates are described, for example, in EP-B1 0 561 825, EP-B1 0 561 999, DE-A1 42 04 700 or by AKBiswas et al. in J.Am.Oil.Chem.Soc. 37, 171 (1960) and FUAhmed in J.Am.Oil.Chem.Soc. 67, 8 (1990).
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule and sulfosuccinic acid and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid monoalkyl polyoxyethyl ester with 8 to 18 C atoms in the alkyl group and 1 to 6 oxyethyl groups.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and carry at least one -COO (_) - or -S ⁇ 3 (_) group.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyl-dimethylammonium glycinate, and 2 -Alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty
  • Ampholytic surfactants are surface-active compounds which, in addition to a C - C 24 - alkyl or acyl group in the molecule at least one free amino group and at least one -COOH or -SO 3 H group and are capable of forming inner salts.
  • suitable ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N- alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-
  • Alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 24 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethyl aminopropionate and C12 C 18 - sarcosine.
  • Nonionic surfactants contain z as a hydrophilic group.
  • B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
  • Such connections are, for example
  • Ci2-C 30 fatty acid monoesters and diesters of addition products from 1 to 30
  • Polyol fatty acid esters such as the commercial product Hydagen ® HSP
  • R 9 CO for a linear or branched, saturated and / or unsaturated acyl radical 6 to 22 carbon atoms
  • R 10 for hydrogen or methyl
  • R 11 for linear or branched alkyl radicals with 1 to 4
  • Carbon atoms and w represents numbers from 1 to 20,
  • Sorbitan fatty acid esters such as the polysorbates
  • Alkyl, Z stands for sugar and x for the number of sugar units.
  • the alkyl polyglycosides which can be used according to the invention can contain only one specific alkyl radical R. Usually, however, these compounds are made from natural fats and oils or mineral oils.
  • alkyl radicals R are mixtures corresponding to
  • Any mono- or oligosaccharides can be used as the sugar building block Z.
  • Sugar with 5 or 6 carbon atoms and the corresponding oligosaccharides are usually used.
  • sugars are glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, old rose, mannose, gulose, idose, talose and sucrose.
  • Preferred sugar components are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
  • alkyl polyglycosides which can be used according to the invention contain on average 1.1 to 5 sugar units. Alkyl polyglycosides with x values of 1.1 to 2.0 are preferred. Alkyl glycosides in which x is 1.1 to 1.8 are very particularly preferred.
  • alkoxylated homologs of the alkyl polyglycosides mentioned can also be used according to the invention. These homologues can contain an average of up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.
  • the alkylene oxide adducts with saturated linear fatty alcohols and fatty acids, each with 2 to 30 moles of ethylene oxide per mole of fatty alcohol or fatty acid, have proven to be preferred nonionic surfactants. Preparations with excellent properties are also obtained if they contain fatty acid esters of ethoxylated glycerol as nonionic surfactants. These connections are characterized by the following parameters.
  • the alkyl radical R contains 6 to 22 carbon atoms and can be either linear or branched. Primary linear and methyl-branched aliphatic radicals in the 2-position are preferred.
  • alkyl radicals are, for example, 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl.
  • 1-Octyl, 1-decyl, 1-lauryl, 1-myristyl are particularly preferred.
  • oxo alcohols compounds with an odd number of carbon atoms in the alkyl chain predominate.
  • the compounds with alkyl groups used as surfactant can each be uniform substances. However, it is generally preferred to start from natural vegetable or animal raw materials in the production of these substances, so that substance mixtures with different alkyl chain lengths depending on the respective raw material are obtained.
  • both products with a "normal” homolog distribution and those with a narrowed homolog distribution can be used.
  • “Normal” homolog distribution is understood to mean mixtures of homologs which are obtained as catalysts from the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates.
  • narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homolog distribution can be preferred.
  • nonionic, zwitterionic and / or amphoteric surfactants and mixtures thereof can be preferred.
  • Cationic surfactants of the type of the quaternary ammonium compounds, the esterquats and the amidoamines can also be used according to the invention.
  • Preferred quaternary ammonium compounds are ammonium halides, especially chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B.
  • cetyltrimethylammonium chloride stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, and the imidazolium compounds known under the INCI names Quaternium-27 and Quaternium-83.
  • the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
  • Ester quats are known substances which contain both at least one ester function and at least one quaternary ammonium group as a structural element.
  • Preferred ester quats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyldialkylamines.
  • Such products are sold, for example, under the trademarks Stepantex ® , Dehyquart ® and Armocare ® .
  • alkylamidoamines are usually produced by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
  • An inventively particularly suitable compound from this group is that available under the name Tegoamid ® S 18 commercially stearamidopropyl dimethylamine.
  • a hair treatment composition according to the invention contains an alkyl sulfate or alkyl polyglycol ether sulfate as the anionic surfactant, the sodium salt of double or triple ethoxylated lauryl or myristyl alcohol being particularly preferred as the alkyl polyglycol ether sulfate.
  • the preferably anionic surfactants can be used in amounts of about 0.1 to about 30% by weight, preferably about 1 to about 20% by weight and very particularly preferably from about 5 to about 15% by weight. based on the total agent.
  • the agents according to the invention can also contain a natural emulsifier.
  • Preferred natural emulsifiers are phospholipids, in particular lecithin, saponins, bile acids and their derivatives, in particular cholic acid, deoxycholic acid, lithocholic acid and taurocholic acid, tannic acid and abientic acid. Phospholipids and saponins are preferred natural emulsifiers.
  • the hair treatment compositions according to the invention can furthermore contain at least one fatty substance or a wax.
  • Preferred fatty substances are linear and branched, saturated and unsaturated fatty alcohols or fatty alcohol mixtures based on natural raw materials with 8 to 22 carbon atoms in the alkyl chain, such as, for example, decanol, octanol, octenol, dodecenol, decenol, octadienol, dodecadienol, decadienol, oleyl alcohol, eruco alcohol, ricinol alcohol , stearyl alcohol, isostearyl alcohol, cetyl alcohol, lauryl alcohol, myristyl alcohol, arachidyl alcohol, caprylic alcohol, capric alcohol, linoleyl alcohol, linolenyl alcohol and behenyl alcohol, and their Guerbet alcohols, as well as fatty alcohol cuts the naturally occurring by reducing triglycerides such as beef tallow, palm oil, peanut oil, rapeseed oil, cottonseed oil
  • Monoesters of fatty acids with alcohols with 6 to 24 carbon atoms and triglycerides of natural origin can also be used as fatty substances.
  • Paraffin oils and vegetable oils such as jojoba oil, sunflower oil, orange oil, almond oil, wheat germ oil, peach seed oil, henna oil from Lawsonia inermis and oil from Cassia auriculata can also be used as fatty substances.
  • Fatty substances for the purposes of the invention are also silicone oils, in particular dialkyl and alkylarylsiloxanes, such as, for example, dimethylpolysiloxane and methylphenylpolysiloxane, and their alkoxylated and quaternized analogs.
  • silicone oils in particular dialkyl and alkylarylsiloxanes, such as, for example, dimethylpolysiloxane and methylphenylpolysiloxane, and their alkoxylated and quaternized analogs.
  • examples of such silicones are the products sold by Dow Corning under the names DC 190, DC 200, DC 344, DC 345 and DC 1401.
  • waxes are esters of long-chain fatty acids with long-chain fatty alcohols. According to the invention, both natural waxes, chemically modified waxes and synthetic waxes can be used. Examples of such waxes are
  • Vegetable waxes such as candelilla wax, camauba wax, japan wax, esparto grass wax, cork wax, guaruma wax, rice germ oil wax, sugar cane wax, ouricury wax and montan wax,
  • Animal waxes such as beeswax, shellac wax, walrus, lanolin and pretzel fat,
  • Petrochemical waxes such as petrolatum, paraffin waxes and micro waxes
  • Hard waxes such as Montanester waxes, Sasol waxes and hydrogenated jojoba waxes, as well
  • Waxes preferred according to the invention are vegetable waxes such as candelilla wax, camamauba wax and Japanese wax and beeswax.
  • the fatty substances or waxes are usually present in amounts of from 0.01 to 15% by weight, preferably from 0.1 to 10% by weight and particularly preferably from 0.3 to 6% by weight, based on the total composition, used.
  • the amount of fat can also be up to 90% by weight.
  • the hair treatment compositions according to the invention can contain at least one protein hydrolyzate or a derivative thereof. Protein hydrolyzates are product mixtures that are obtained by acidic, basic or enzymatically catalyzed breakdown of proteins (proteins).
  • protein hydrolyzates of both vegetable and animal origin can be used.
  • Animal protein hydrolyzates are, for example, elastin, collagen, keratin, silk and milk protein protein hydrolyzates, which can also be in the form of salts.
  • Such products are, for example, under the trademarks Dehylan ® (Cognis), Promois ® (Interorgana), Collapuron ® (Cognis), Nutrilan ® (Cognis), Gelita-Sol ® (Deutsche Gelatine Fabriken Stoess & Co), Lexein ® (Inolex) and Kerasol ® (Croda) sold.
  • protein hydrolysates of plant origin e.g. B. soy, almond, rice, pea, potato and wheat protein hydrolyzates.
  • Such products are available, for example, under the trademarks Gluadin ® (Cognis), DiaMin ® (Diamalt), Lexein ® (Inolex) and Crotein ® (Croda).
  • amino acid mixtures or individual amino acids such as arginine, lysine, histidine or pyrroglutamic acid, which have otherwise been obtained, can optionally be used in their place.
  • derivatives of the protein hydrolyzates for example in the form of their fatty acid condensation products. Such products are sold for example under the names Lamepon ® (Cognis), Gluadin ® (Cognis), Lexein ® (Inolex), Crolastin ® (Croda) or Crotein ® (Croda).
  • Cationized protein hydrolyzates can also be used according to the invention, the underlying protein hydrolyzate being derived from animals, for example from collagen, milk or keratin, from the plant, for example from wheat, corn, rice, potatoes, soy or almonds, from marine life forms, for example from fish collagen or algae, or from biotechnologically obtained protein hydrolyzates.
  • the protein hydrolysates on which the cationic derivatives according to the invention are based can be obtained from the corresponding proteins by chemical, in particular alkaline or acidic hydrolysis, by enzymatic hydrolysis and / or a combination of both types of hydrolysis.
  • the hydrolysis of proteins usually results in a protein hydrolyzate with a molecular weight distribution of approximately 100 daltons up to several thousand daltons.
  • Preferred cationic protein hydrolyzates are those whose underlying protein content has a molecular weight of 100 to 25,000 Daltons, preferably 250 to 5000 Daltons.
  • Cationic protein hydrolyzates also include quaternized amino acids and their mixtures. The quaternization of the protein hydrolyzates or the amino acids is often carried out using quaternary ammonium salts such as, for example, N, N-dimethyl-N- (n-alkyl) -N- (2-hydroxy-3-chloro-n-propyl) ammonium halides.
  • the cationic protein hydrolyzates can also be further derivatized.
  • inventive cationic protein hydrolysates and derivatives are under the INCI - th names in the "International Cosmetic Ingredient Dictionary and Handbook" (seventh edition 1997, The Cosmetic, Toiletry, and Fragrance Association 1101 17 Street, NW, Suite 300 , Washington, DC 20036-4702) and commercially available products: Cocodimonium hydroxypropyl hydrolyzed collagen, Cocodimonium hydroxypropyl hydrolyzed casein, Cocodimonium hydroxypropyl hydrolyzed collagen, Cocodimonium hydroxypropyl hydrolyzed hair keratin, Cocodimonium hydroxypropyl hydrolyzed keratin, Cocodimonium hydroxypropyl hydrolyzed Rice Hydrolyzed Silk, Cocodimonium Hydroxypropyl Hydrolyzed Soy Protein, Cocodimonium Hydroxypropyl Hydrolyzed Wheat Protein, Cocodimonium Hydroxypropyl Silk Amino Acids, Hydroxypropyl Arginine Lauryl / Myr
  • the protein hydrolyzates and their derivatives can be contained in the agents according to the invention in amounts of 0.01 to 10% by weight, based on the total agent. Amounts of 0.1 to 5% by weight, in particular 0.1 to 3% by weight, are very particularly preferred.
  • the hair treatment compositions according to the invention can contain a conditioning agent selected from the group formed by cationic surfactants, cationic polymers, alkylamidoamines and synthetic oils.
  • Cationic polymers can be preferred as conditioning agents. These are usually polymers that have a quaternary nitrogen atom, for example in
  • Preferred cationic polymers are, for example, quaternized cellulose derivatives, such as are available under the names of Celquat ® and Polymer JR ® commercially.
  • the compounds Celquat ® H 100, Celquat ® L 200 and Polymer JR ® 400 are preferred quaternized cellulose derivatives.
  • polymeric dimethyldiallylammonium salts and their copolymers with esters and amides of acrylic acid and methacrylic acid are examples of such cationic polymers.
  • Copolymers of vinylpyrrolidone with quaternized derivatives of dialkylaminoacrylate and methacrylate such as, for example, vinylpyrrolidone-dimethyfaminomethacrylate copolymers quaternized with diethyl sulfate.
  • vinylpyrrolidone-dimethyfaminomethacrylate copolymers quaternized with diethyl sulfate are commercially available under the names Gafquat ® 734 and Gafquat ® 755.
  • Vinylpyrrolidone-methoimidazolinium chloride copolymers such as are offered under the name Luviquat ® , quaternized polyvinyl alcohol and those under the names Polyquatemium 2, Polyquaternium 17, Polyquatemium 18 and
  • Polyquatium 27 known polymers with quaternary nitrogen atoms in the main polymer chain.
  • Cationic polymers of the first four groups are particularly preferred.
  • Preferred cationic surfactants are those of the quaternary ammonium compound type, for example ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and triaikylmethylammonium chlorides, e.g. B. cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride,
  • these quaternary ammonium compounds can also be so-called esterquats such as N obtainable under the name Armocare® ® VGH-70 commercially, N-bis (2-palmitoyloxyethyl) dimethyl be used instead.
  • alkylamidoamines such as that commercially available under the name Tegoamid ® S 18
  • conditioning agents are silicone oils, in particular dialkyl and alkylarylsiloxanes, such as dimethylpolysiloxane and methylphenylpolysiloxane, and their alkoxylated and quaternized analogs.
  • silicones examples include the Dow Corning under the names DC 190, DC 200, DC 344, DC 345 and DC 1401 products sold and the commercial products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethyl silylamodimethicon), Dow Corning ® 929 emulsion (containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer. Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th Goldschmidt; diquaternary polydimethylsiloxanes, Quatemium-80).
  • Paraffin oils and vegetable oils such as jojoba oil, sunflower oil, orange oil, almond oil, wheat germ oil and peach seed oil can also be used as conditioning agents.
  • suitable hair-conditioning compounds are phospholipids, for example soy lecithin, egg lecithin and cephalins.
  • the conditioning agents can be present in the agents according to the invention in amounts of about 0.01 to about 10% by weight, based on the total agent. Amounts from about 0.1 to about 5% by weight, in particular about 0.1 to about 3% by weight, are very particularly preferred.
  • Hair treatment agents according to the invention which are hair coloring or tinting agents, can contain at least one oxidation dye precursor of the developer type, if appropriate in combination with oxidation dye precursors of the coupler type, and / or a substantive dye and / or a dye which occurs naturally.
  • the hair treatment compositions according to the invention can, if necessary additionally, serve for the permanent shaping of human hair.
  • Permanent hair shaping is carried out according to the known permanent wave method in such a way that the hair is mechanically deformed and the deformation z. B. by winding on hair rollers or papillots.
  • the hair Before and / or after this shaping, the hair is treated with the aqueous preparation of a keratin-reducing substance and rinsed with water or an aqueous solution after an exposure time.
  • the hair is then treated with the aqueous preparation of an oxidizing agent. After an exposure time, this is also rinsed out of the hair and the hair is freed from the mechanical shaping aids (curlers, papillots).
  • the aqueous preparation of the keratin reducing agent is usually made alkaline so that the hair swells and in this way a deep penetration of the keratin-reducing substance into the hair is made possible.
  • the keratin-reducing substance cleaves part of the disulfide bonds of the Keratins to -SH groups, so that there is a loosening of the peptide crosslinking and due to the tension in the hair due to the mechanical deformation to a new orientation of the keratin structure. Under the influence of the oxidizing agent, disulfide bonds are again formed, and in this way the keratin structure is re-fixed in the predetermined deformation.
  • the nonionic crosslinked (meth) acrylate-containing polymers according to the invention can be incorporated both in the keratin-reducing (waving agent) and in the keratin-oxidizing agent (fixing solution) of the permanent waving treatment.
  • the use of the polymers according to the invention in fixing solutions is particularly preferred.
  • oxidizing agents e.g. As sodium bromate, potassium bromate, hydrogen peroxide, and the usual stabilizers for stabilizing aqueous hydrogen peroxide preparations.
  • the pH of such aqueous H 2 ⁇ 2 preparations which usually contain about 0.5 to 3.0% by weight of H2O2, is preferably 2 to 4; it is adjusted by inorganic acids, preferably phosphoric acid.
  • Bromate-based fixatives usually contain the bromates in concentrations of 1 to 10% by weight and the pH of the solutions is adjusted to 4 to 7.
  • Fixing agents based on enzymes (peroxidases) which contain no or only small amounts of oxidizing agents, in particular H 2 O 2 , are also suitable.
  • the pH of the agents according to the invention can be between 2-11, the person skilled in the art knowing the preferred pH ranges for the different agents.
  • the pH of the agents according to the invention provided they are hair care agents, is preferably between 2 and 7, with values from 3 to 5 being particularly preferred. Setting this pH can be convenient any acid used for cosmetic purposes can be used. Eating acids are usually used. Edible acids are understood to mean those acids that are ingested as part of normal food intake and have positive effects on the human organism. Edible acids are, for example, acetic acid, lactic acid, tartaric acid, citric acid, malic acid, ascorbic acid and gluconic acid. In the context of the invention, the use of citric acid and lactic acid is particularly preferred. Hair colorants are preferably formulated in a pH range of about 7 to 11.
  • the hair treatment compositions according to the invention can contain all the additives customary for the respective intended use.
  • these can be cosmetic additives which have a cleaning, nourishing or other effect on the external appearance of the hair.
  • Such additives which do not have a direct effect on the hair, but otherwise have a positive effect on the scalp or, for example, the hair follicles, can also be present in the preparation according to the invention.
  • customary constituents of the preparations according to the invention can be: anionic, zwitterionic, amphoteric and nonionic polymers such as, for example, vinyl acetate / crotonic acid copolymers, polydimethylsiloxanes, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers and maleinic acid copolymers, methyl vinyl ether thereof, methyl vinyl ether Esters, uncrosslinked and crosslinked with polyols, acrylic amidopropyl-trimethylammonium chloride / acrylate copolymers, octylacrylamide / - methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyvinylpyrrolidone,
  • dialkyl ethers with a total of between 12 to 36 carbon atoms, in particular 12 to 24 carbon atoms, for example di-n-octyl ether, di-n-decyl ether, di-n-nonyl ether, di-n- undecyl ether and di-n-dodecyl ether, n-hexyl-n-octyl ether, n-octyl-n-decyl ether, n-decyl-n-undecyl ether, n-undecyl-n-dodecyl ether and n-hexyl-n-undecyl ether as well as di- tert-butyl ether, di-iso-pentyl ether, di-3-ethyldecyl ether, tert-butyl-n-octyl ether, is
  • Thickeners such as gelatin or vegetable gums, for example agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays and layered silicates such as. B. bentonite or fully synthetic hydrocolloids such.
  • Refatting agents such as fatty acid alkanolamides, fatty acids, fatty acid esters such as isopropyl myristate, palmitate, oleate and stearate, optionally ethoxylated partial glycerides, wool wax derivatives, lecithin, perhydrosqualene,
  • Isopropyl adipate or the fatty substances described above structurants such as maleic acid, mono-, di- and oligosaccharides, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, dyes for coloring the agent,
  • Antidandruff active ingredients such as piroctone olamine, zinc omadine and climbazole, other substances for adjusting the pH, vitamins and vitamin precursors such as panthenol, its derivatives and biotin, plant and honey extracts, such as in particular extracts from oak bark, nettle, witch hazel, hops, chamomile, Burdock root, horsetail, linden flowers, almond, aloe vera, coconut, mango, apricot, lime, wheat, kiwi, melon, orange, grapefruit, sage, rosemary, birch, cuckoo flower, quendel, yarrow, squirrel, meristem, ginseng and ginger ginger ginger
  • active ingredients such as ceramides, allantoin, pyrrolidone carboxylic acids, and bisabolol, light stabilizers,
  • Consistency agents such as sugar esters, polyol esters or polyol alkyl ethers, fatty acid alkanolamides, physiologically compatible inorganic or organic acids, swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates,
  • Humectants such as sorbitol, lactic acid salts, glycerol or polysaccharide opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers, pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate, complexing agents such as EDTA, NTA, ß-alanine diacetic acid and phosphonic acid Reducing agents such as thioglycolic acid and its derivatives, thiolactic acid, cysteamine, thio malic acid and ⁇ -mercaptoethanesulfonic acid, oxidizing agents such as hydrogen peroxide, potassium bromate and sodium bromate, blowing agents such as propane-butane mixtures, N 2 0, dimethyl ether, CO 2 , N 2 and air and antioxidants.
  • pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate
  • complexing agents such
  • the agents can be packaged in the form of foam aerosols.
  • foam aerosols Both the formulation with a liquefied gas as a blowing agent and in the form of so-called pump sprays are possible, in which the pressure required for spraying is built up by mechanical pumping. Nitrogen, air, carbon dioxide, propane, butane, isobutane, pentane and dimethyl ether are preferred blowing agents.
  • chlorofluorocarbons and chlorinated hydrocarbons are excellent propellants with regard to the aerosol properties achieved, their use as propellants is in the Agents according to the invention are less preferred due to the known ozone problem.
  • Another object of the present invention is a method for setting hair, in which an inventive hair treatment agent, as described in the preceding text, is applied to the hair in an effective amount.
  • the agent can then be rinsed out again after a contact time or left on the hair until the next hair wash.
  • the agent is rinsed out again after an exposure time.
  • nonionic, crosslinked (meth) acrylate-containing polymers with an average particle diameter in the range from 50 to 500 nm in the hair treatment compositions described in the preceding text has advantages for both the manufacturer and the user of such compositions connected is.
  • the invention enables the formulation of combination preparations which, in addition to a first effect, such as, for example, hair cleaning or hair coloring, have hair fixation as a further effect. Separate post-treatment is no longer necessary for hair fixation, and the user saves one application step. At the same time, the packaging effort is reduced because one product is used less.
  • a first effect such as, for example, hair cleaning or hair coloring
  • Example 1 Preparation of a polymer starting from N-isopropylacrylamide (“P-N-IPAAm”)
  • the hydrogel particles thus synthesized had a diameter of approx. 200 to 300 nm in the swollen state at room temperature, ie. H. in the state of dispersion.
  • the particle size was determined by laser diffraction using the Malvern Mastersizer-RT.
  • the N-isopropylacrylamide was no longer detectable in the dispersion by means of HPLC ( ⁇ 1ppm).
  • the polymer dispersion thus prepared was then freeze-dried, the polymer being obtained in a non-swollen form as a white powder in a yield of 95%. It had a glass transition temperature of 152 ° C (measurement using modulated dynamic differential calorimetry, MDSC).
  • MDSC modulated dynamic differential calorimetry
  • the polymer can e.g. redisperse with water to a desired concentration.
  • the freeze-dried polymer was redispersed with water to a final concentration of 0.04% by weight, based on the total weight of the aqueous dispersion, corresponding to a concentration of 0.4 g / l of dispersion.
  • the polymer dispersion obtained in the aforementioned synthesis reaction can be separated from the main amount of the salts and water used in the preparation by centrifugation. In this case the polymer is obtained in a swollen state.
  • Example 2 Preparation of a polymer based on ethyl methacrylate and N-vinylpyrrolidone ("EMA-VP")
  • a dispersion was obtained, the viscosity of which was 5 MPas (20 ° C., 20 rpm).
  • the aqueous dispersion was then dialyzed to reduce the level of residual monomers, which is desirable for use in cosmetics.
  • the residual content of N-vinylpyrrolidone was 9 ppm and that of ethyl methacrylate was 16 ppm.
  • the hydrogel particles synthesized in this way had an average particle diameter of approximately 100 to 300 nm at room temperature. They showed no glass temperature below 90 ° C (measurement by MDSC).
  • Examples 3.1-3.23 Preparation of further polymers
  • the crosslinked polymers 3.1 to 3.23 were prepared in a manner analogous to that in Example 2 (cf. Table 1), 5 parts by weight of N, N-methylene bisacrylamide being added to 100 parts by weight of the monomers listed in Table 1 were used for the polymerization reaction.
  • Table 1
  • Example 4 Investigation of the effectiveness of the polymers according to the invention on hair from an aqueous dispersion
  • the work for combing wet strands of hair was measured. Before the zero measurement, the hair was medium-blonded and then combed in the wet state, the combing forces required thereby being recorded. After the zero measurement, the strands of hair were treated once with the respective formulation (10 minutes, 0.5 g Formulation per g of hair) and then rinsed for 1 minute with a total of 1 liter of water at 38 ° C. Each measurement was made with 20 strands of hair. In each case, 10 comb values of a strand of hair were determined and compared before application and after application of the formulations in the wet state.
  • the measurements were carried out in a constant climate (25% relative humidity, 30 ° C); the hair strands were conditioned for 24 hours.
  • the work for combing dry strands of hair was measured.
  • the hair was medium-blonded before the zero measurement and then combed in the dry and conditioned state, the combing forces required being recorded.
  • the strands of hair were treated once with the respective formulation (10 minutes, 0.5 g of formulation per g of hair) and then rinsed for 1 minute with a total of 1 liter of water at 38 ° C. and then dried. Each measurement was made with 20 strands of hair.
  • the sensory assessment was determined using an expert panel.
  • the strands of hair used were initially 30 min. pre-cleaned with a 12% Texapon NSO solution (pH 6.5) and 5 min. rinsed with water.
  • the strands were then treated with the respective formulations (0.5 g formulation per g hair, 5 min exposure time, 1 min rinsing time) and at 20% rel. Humidity in the climate box dried overnight.
  • the tests were carried out in a climate room at 22 ° C and approx. 45% relative humidity with standard daylight lighting. Each subject received new strands of hair.
  • the recipe was assigned to the individual attributes and evaluated against the corresponding reference.
  • the tested attribute lies in the property tested in each case.
  • the panel consisted of 11 experts whose judgments were averaged.
  • the application on strands of hair was standardized using a dipping process. Standard European hair was used, which had been pre-cleaned, rinsed and dried. The hair was then immersed in the aqueous polymer dispersions prepared according to Examples 1 and 2 at a concentration of 0.4 g / l. Depending on the application as rinse-off or leave-on products, the strands of hair were then rinsed off if necessary. The samples were then at 25% rel. Humidity and 30 ° C in the air.
  • the hair gloss was determined by means of light reflection.
  • 5 strands of hair were pretreated according to b) in the form of a leave-on treatment and additionally provided with a gloss-reducing film. It became the Measure the gloss intensity of the untreated strands of hair and then the strands of hair treated with the polymers according to the invention and determine the difference. The measurements were carried out at 25 ° C and 40% rel. Moisture carried out.
  • the volume was determined analytically by casting shadows on the strands of hair.
  • the strands of hair were pretreated in the form of a leave-on treatment.
  • the area of 10 of the untreated and then of the treated strands of hair was determined and compared in each case.
  • Example 5 Investigation of the effectiveness of the polymers according to the invention on hair from a shampoo formulation
  • the polymers according to the invention led to a significant increase in combing work, which is an indication of hair setting and improved hair styling.
  • the polymers according to the invention likewise led to a significant increase in combing forces, which is to be understood as an increased styling effect.
  • the polymer from Example 1 showed a stronger styling effect than the polymer from Example 2.
  • Formulations 5.1a and 5.2b showed a tendency or significantly increased stylability compared to comparative formulation 5.0.

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Abstract

L'invention concerne l'utilisation de polymères non ioniques à réticulation transversale, contenant du (méth)acrylate, présentant un diamètre moyen de particules compris entre 50 et 500 nm, pour fixer des fibres kératiniques. L'invention concerne également des produits de soins capillaires contenant lesdits polymères.
PCT/EP2003/009939 2002-09-17 2003-09-08 Produit de soin capillaire a effet fixateur Ceased WO2004026269A1 (fr)

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AU2003264277A AU2003264277A1 (en) 2002-09-17 2003-09-08 Hair treatment agent having strengthening properties

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DE2002143037 DE10243037A1 (de) 2002-09-17 2002-09-17 Haarbehandlungsmittel mit festigenden Eigenschaften
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CN103917624B (zh) 2011-09-13 2018-11-23 路博润高级材料公司 表面活性剂响应性分散体聚合的微凝胶
JP6162121B2 (ja) 2011-09-13 2017-07-12 ルブリゾル アドバンスド マテリアルズ， インコーポレイテッド 界面活性剤応答性エマルジョン重合ミクロゲル

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0288012A2 (fr) * 1987-04-21 1988-10-26 Kao Corporation Composition cosmétique pour les cheveux
US6126921A (en) * 1994-04-26 2000-10-03 Henkel Kommanditgesellschaft Auf Aktien Hair treatment formulations containing a water-insoluble polymer having a glass transition temperature of -20° C. to 70° C.
EP1092417A1 (fr) * 1999-10-14 2001-04-18 Henkel Kommanditgesellschaft auf Aktien Shampoings contenant un fixateur
WO2002056853A1 (fr) * 2001-01-18 2002-07-25 L'oreal Composition cosmetique irisee et ses utilisations

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0288012A2 (fr) * 1987-04-21 1988-10-26 Kao Corporation Composition cosmétique pour les cheveux
US6126921A (en) * 1994-04-26 2000-10-03 Henkel Kommanditgesellschaft Auf Aktien Hair treatment formulations containing a water-insoluble polymer having a glass transition temperature of -20° C. to 70° C.
EP1092417A1 (fr) * 1999-10-14 2001-04-18 Henkel Kommanditgesellschaft auf Aktien Shampoings contenant un fixateur
WO2002056853A1 (fr) * 2001-01-18 2002-07-25 L'oreal Composition cosmetique irisee et ses utilisations

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