WO2003051320A1 - Procede de mise en forme permanente de fibres keratiniques et agents - Google Patents

Procede de mise en forme permanente de fibres keratiniques et agents Download PDF

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Publication number
WO2003051320A1
WO2003051320A1 PCT/EP2002/013932 EP0213932W WO03051320A1 WO 2003051320 A1 WO2003051320 A1 WO 2003051320A1 EP 0213932 W EP0213932 W EP 0213932W WO 03051320 A1 WO03051320 A1 WO 03051320A1
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WO
WIPO (PCT)
Prior art keywords
preparation
acid
keratin
aqueous
agent
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PCT/EP2002/013932
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German (de)
English (en)
Inventor
Detlef Fischer
Swenja Kalischke
Burkhard Müller
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Henkel Kommanditgesellschaft Auf Aktien
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Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to AU2002361993A priority Critical patent/AU2002361993A1/en
Priority to EP02796590A priority patent/EP1463484A1/fr
Publication of WO2003051320A1 publication Critical patent/WO2003051320A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A61Q5/04—Preparations for permanent waving or straightening the hair

Definitions

  • the invention relates to a process for the permanent deformation of keratin fibers, in particular human hair, by reductive splitting and renewed oxidative formation of disulfide bonds in keratin, and the use of agents suitable for this process.
  • the permanent deformation of keratin fibers is usually carried out in such a way that the fiber is mechanically deformed and the deformation is determined by suitable aids.
  • the fiber Before and / or after this deformation, the fiber is treated with the aqueous preparation of a keratin-reducing substance and rinsed with water or an aqueous solution after an exposure time.
  • the fiber is then treated with the aqueous preparation of an oxidizing agent. After an exposure time, this is also rinsed out and the fiber is freed from the mechanical deformation aids (curlers, papillots).
  • the aqueous preparation of the keratin reducing agent is usually made alkaline, so that on the one hand a sufficient proportion of the thiol functions are deprotonated and on the other hand the fiber swells and in this way a deep penetration of the keratin-reducing substance into the fiber is made possible.
  • the keratin-reducing substance cleaves a part of the disulfide bonds of the keratin to -SH groups, so that the peptide cross-linking is loosened and the fiber deformation due to the mechanical deformation leads to a reorientation of the keratin structure.
  • a known method of this type is permanent wave treatment of human hair. This can be used both for producing curls and waves in straight hair and for straightening curly hair.
  • a negative side effect of the permanent waving of the hair that is carried out in this way is often embrittlement and dulling of the hair.
  • other properties such as wet and dry combability, grip, smoothness, softness, gloss and tear resistance are also influenced in an undesirable manner.
  • these negative side effects are influenced by the condition of the parent hair and essentially by the pH of the reducing solution.
  • a low pH generally leads to fewer undesirable effects, but the wave power and the durability of the perm are often not sufficient.
  • a higher pH value leads to a satisfactory wave output, but also to significantly increased negative side effects, especially on hair that has already been preloaded.
  • An optimally formulated permanent waving agent should therefore specifically enable a desired shaping performance while influencing the hair structure as little as possible.
  • Nourishing additives and film formers are often added to the permanent waving agent without, however, significantly improving the hair structure.
  • high-molecular polymers are used, for example, which attach to the top layer of skin and hair and there produce an external, subjectively perceptibly improved handle on the hair.
  • the structural damage to the inside of the hair which is caused by the reduction process in the case of perms, cannot be reduced, however, because the substances cannot penetrate the hair due to their size.
  • EP 723 772 describes that alkalizing agents such as basic amino acids together with cationic polymers in the waving agent cause the hair to swell more. On the one hand it leads to stronger shaping and longer durability of the perm, but on the other hand it also leads to the observed hair damage.
  • a method is described in which hair, skin or nails ⁇ first be treated with a reducing agent, which is then rinsed. Then an aqueous protein hydrolyzate, preferably with a molecular weight greater than 50,000 Daltons, is applied to the areas to be treated, after which the neutralization is carried out. Subjectively, the area treated in this way felt better, hair damage was reduced on the inside, however (due to the high
  • the object of the invention is to find a process for the permanent deformation of keratin fibers, in which not only the surface of the hair is improved, but also the damage inside the fibers is reduced, and in which the further undesirable side effects mentioned are also significantly reduced become.
  • the invention therefore relates to a process for the permanent deformation of keratin fibers, in which the fiber is treated with an aqueous preparation (A) of a keratin-reducing substance before and / or after mechanical deformation, rinsed out with water and / or an aqueous agent after an exposure time is then applied an aqueous preparation (B), then fixed after an exposure time with an aqueous preparation (C) of an oxidizing agent and optionally rinsed after an exposure time and optionally aftertreated, whereby preparation (B) at least one protein hydrolyzate and additionally one or more Contains amino acids.
  • Care product for the aqueous preparation (B) of protein hydrolyzate and additional amino acid
  • These agents are used in the course of a process for the permanent shaping of keratin fibers and can contain all the constituents customary for these agents.
  • the method according to the invention for the permanent deformation of keratin fibers is preferably used for perming or straightening human hair.
  • the preparation (B) used according to the invention contains at least one protein hydrolyzate.
  • Protein hydrolyzates are product mixtures that are obtained by acidic, basic or enzymatically catalyzed breakdown of proteins (proteins).
  • protein hydrolyzates is understood to mean “polymers also built up from amino acids and amino acid derivatives. These include, for example, polyalanine, polyasparagine, polyserine, polyglycine, etc. Total hydrolysates of proteins are not to be understood by the term protein hydrolysates in the sense of the invention.
  • the protein hydrolyzates are preferably contained in the preparation (B) used according to the invention in amounts of 0.01 to 10% by weight. Amounts of 0.1 to 4% by weight are particularly preferred.
  • the protein hydrolyzates can be of vegetable, animal, marine or synthetic origin.
  • the preparation (B) used according to the invention contains vegetable and / or animal protein hydrolyzates Origin.
  • vegetable uride / or animal protein hydrolyzates is the particularly good biological compatibility of the products. i
  • 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 brands Dehylan ® (Cognis), Promois ® (Interorgana), Collapuron ® (Cognis), Nutrilan ® (Cognis), Gelita-Sol ® (Deutsche Gelatine Fabriken Stoess & Co), Lexein ® (Inolex) and Kerasol ® (Croda).
  • Protein hydrolysates of plant origin come e.g. B. Soybean, almond, pea, potato and wheat protein hydrolyzates into consideration.
  • Such products are, for example, under the brand names Gluadin® ® (Cognis), DiaMin® ® (Diamalt) ® (Inolex), Hydrosoy ® (Croda), hydro Lupine ® (Croda), hydro-Sesame ® (Croda), hydro Tritium ® (Croda) and Orotein ® (Croda) available.
  • the care agent (B) contains keratin hydrolyzate.
  • Keratin hydrolyzate has the particular advantage that it is well absorbed on the hair and thereby helps to protect the hair and improve the structure.
  • the molecular weight of the protein hydrolyzates that can be used is between 500 and 200,000 daltons.
  • the molecular weight is preferably 1000 to 50,000 and very particularly preferably 1000 to 10,000 Daltons.
  • amino acid mixtures obtained in some other way can optionally be used in their place. It is also possible to use 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), Lexein ® (Inolex), Crolastin ® (Croda) or crotein ® (Croda).
  • the amino acid additionally contained in the care product (B) used according to the invention can be used both as a free amino acid and as a salt, e.g. B. as hydrochloride or alkali or ammonium salt.
  • the amino acid can be in both D and L form.
  • the content of additional amino acids in preparation (B) is preferably 0.1 to 10% by weight, particularly preferably 0.5 to 4% by weight and in particular 1 to 2.5% by weight. %.
  • At least one of the amino acids additionally contained in preparation (B) is selected from histidine, arginine or lysine, in particular histidine.
  • these amino acids carry a further basic imidazolinium, guanidinium or ammonium group in the side chain.
  • the ratio of amino acid to protein hydrolyzate contained in preparation (B) in% by weight is 1: 0.01 to 1:10, with 1: 0.1 to 1: 3 being particularly preferred.
  • the hair structure of the cortex is less damaged compared to the values without care treatment or only with protein hydrolyzate.
  • the care agent (B) preferably has a pH between 3 and 9, and in particular from 4 to 7, e.g. 6.3, on.
  • the care product (B) used according to the invention can also be rinsed out of the hair after the exposure time before the fixative (C) is applied. i ' ,
  • fixative (C) after the contact time of the care product (B) is preferred.
  • preparation (B) is in the form of a concentrate or powder which is diluted with water or dissolved and / or suspended in water before use in order to obtain the ready-to-use preparation.
  • the preparations (A, B, C) used according to the invention can also be formulated as a cream, gel or liquid. Furthermore, it is possible to assemble the agent in the form of foam aerosols, which are mixed with a liquefied gas such. B. propane-butane mixtures, nitrogen, CO 2 , air, NO2, dimethyl ether, chlorofluorocarbon blowing agents or mixtures thereof are filled in aerosol containers with a foam valve.
  • the individual components of the method according to the invention are preferably used as a cream, gel or liquid.
  • All aqueous preparations of the process according to the invention can also be made from two different components, e.g. in the case of preparation (A) from a corrugated solution and a care component. Furthermore, the care product (B), the corrugation product (A) and / or the fixation (C) as such can already be in two or more phases.
  • Two-phase and multi-phase systems are systems in which there are at least two separate, continuous phases.
  • an aqueous phase and one or more e.g. two, non-miscible, non-aqueous phases are present separately from each other.
  • the aqueous and the non-aqueous phases lie in the agents used in the process according to the invention, the waving agent (A), the Care product (B) and the fixation (C), in proportions (based on the weight) of 1: 200 to 1: 1, preferably from 1:40 to 1: 5 and particularly preferably from 1:20 to 1:10. In cases where there are several non-aqueous phases, this information refers to the total of the non-aqueous phases.
  • the wave agents (A) used according to the invention contain the mercaptans known as keratin-reducing substances.
  • the keratin-reducing substances are " selected " from _ thioglycolic acid, thiolactic acid, thio malic acid, mercaptoethanesulfonic acid and their salts and esters, cysteamine, cysteine, multicolored salts and salts of sulfurous acid and mixtures thereof.
  • the alkali metal or ammonium salts of thioglycolic acid, thio malic acid and / or thiolactic acid are particularly suitable.
  • the keratin-reducing substances are preferably used in the waving agents (A) in concentrations of 0.3 to 2.0 mol / kg at a pH of 5 to 12, in particular from 7 to -9.5. Mixtures of salts of thioglycolic acid and salts of thiolactic acid can be preferred. To adjust this pH
  • the waving agents (A) usually contain alkalizing agents such as ammonia, alkali and ammonium carbonates and hydrogen carbonates or organic amines such as monoethanolamine.
  • the exposure time of the waving agents (A) to the hair is generally 5 to 40 minutes, the thickness of the hair to be treated, the condition of the hair, the desired degree of deformation, the size of the mechanical deformation aid used (hair roller) and the type of keratin reducing agent being further influencing factors are.
  • Heterocyclic compounds such as, for example, derivatives of imidazole, pyrrolidine, piperidine, dioxolane, dioxane, morpholine and piperazine can be used as further care substances in the aqueous wave agent (A).
  • suitable derivatives of these compounds such as, for example, the C 4 alkyl derivatives, C 1 hydroxyalkyl derivatives and C 1 -C 4 aminoalkyl derivatives.
  • Preferred substituents which can be positioned both on carbon atoms and on nitrogen atoms of the heterocyclic ring systems are methyl, ethyl, ⁇ -hydroxyethyl and ⁇ -aminoethyl groups. These derivatives preferably contain one or two of these substituents.
  • heterocyclic compounds preferred according to the invention are, for example, 1-methylimidazole, 2-methylimidazole, 4 (5) -methylimidazole, 1,2-dimethylimidazole, 2-ethylimidazole, 2-isopropylimidazole, N-methylpyrrolidone, 1-methylpiperidine, 4-methylpiperidine, 2- Ethyl piperidine, 4-methylmorpholine, 4- (2-hydroxyethyl) morpholine, 1-ethylpiperazine, 1- (2-hydroxyethyl) piperazine, 1- (2-aminoethyl) piperazine.
  • Imidazole derivatives which are further preferred according to the invention are biotin, hydantoin and benzimidazole.
  • the mono- and dialkylimidazoles, biotin and hydantoin are particularly preferred.
  • penetration aids and / or swelling agents are contained in the wave means (A).
  • these include, for example, urea and urea derivatives, guanidine and its derivatives, water glass, imidazole and its derivatives, benzyl alcohol, glycerol, glycol and glycol ethers, propylene glycol and propylene glycol ethers, for example propylene glycol monoethyl ether, carbonates, hydrogen carbonates, diols and triols, and in particular 1,2- Diols and 1, 3-diols as described for example below under the term polyols.
  • the penetration aids and swelling agents are contained in the preparations used according to the invention in amounts of 0.1 to 20% by weight. Amounts of 0.1 to 10% by weight are preferred.
  • the corrugating agents used according to the invention can contain corrugation-strengthening components, in particular urea, imidazole and the above-mentioned diols.
  • corrugation-strengthening components in particular urea, imidazole and the above-mentioned diols.
  • the waving power Compounds can be contained in the waving agents used according to the invention in amounts of 0.5 to 5% by weight, in particular 1 to 4% by weight.
  • the active substances described below can be used particularly advantageously within the scope of the invention as further constituents of both the corrugating agent (A) and the care agent (B) and / or the fixation (C).
  • the active substances are polyols, in particular glycerol and partial glycerol ether, 2-ethyl-1,3-hexanediol, 1,3-butanediol, 1,4-butanediol, 1,2-propanediol, 1,3-propanediol, pentanediols, for example 1,2 -Pentanediol, hexanediols, for example 1, 2-hexanediol or 1, 6-hexanediol, dodecanediol, in particular 1,2-dodecanediol, neopentyl glycol and ethylene glycol are suitable.
  • 2-ethyl-1,3-hexanediol, 1,2-propanediol, 1,3-propanediol and 1,3-butanediol have proven to be particularly suitable.
  • polyols are preferably contained in the waving agents used according to the invention in amounts of 1 to 10, in particular 2 to 10,% by weight.
  • alcohols in particular in multiphase systems, which are not more than 10% by weight soluble in water at 20 ° C., based on the mass of water.
  • Fatty substances such as fatty acids, fatty alcohols, natural and synthetic waxes, which can be present both in solid form and in liquid form in aqueous dispersion, and natural and synthetic cosmetic oil components can be used as further care substances.
  • Natural and synthetic cosmetic oil bodies which can be used according to the invention are in particular:
  • oils examples include sunflower oil, olive oil, soybean oil, rapeseed oil, almond oil, jojoba oil, wheat germ oil and the liquid components of coconut oil and triglyceride oils (for example the liquid components of beef tallow or synthetic triglyceride oils).
  • the compounds are available as commercial products 1, 3-di- (2-ethyl-hexyl) -cyclbhexan (Cetiol ® S), and di-n-octyl ether (Cetiol ® OE) may be preferred.
  • the amount of natural and synthetic cosmetic oil bodies used in the agents used according to the invention is usually 0.1 to 30% by weight, based on the total agent, preferably 0.1 to 20% by weight, and in particular 0.1 to 15% by weight .-%.
  • the total amount of oil and fat components in the agents used according to the invention is usually 0.1 to 75% by weight, based on the total agent. Amounts of 0.1 to 35% by weight are preferred.
  • polymers are advantageously used in the process according to the invention.
  • polymers are therefore added to the agents used according to the invention, both cationic, anionic, amphoteric and nonionic polymers having proven to be effective.
  • Cationic polymers are understood to mean polymers which have a group in the main and / or side chain and which have a cationic group as a function of or independently of the pH of the agent. Polymers in which the quaternary ammonium group is bonded via a C1-4 hydrocarbon group to a polymer main chain composed of acrylic acid, methacrylic acid or their derivatives have proven to be particularly suitable.
  • a particularly suitable homopolymer is that which may also be crosslinked, poly (methacryloyloxyethyltrimethylammonium chloride) with the INCI name Polyquaternium-37.
  • the crosslinking can be carried out with the aid of polyolefinically unsaturated compounds, for example divinylbenzene, tetraallyloxyethane, methylene bisacrylamide, diallyl ether, polyallylpolyglyceryl ether, or allyl ethers of sugars or sugar derivatives such as erythritol, pentaerythritol, Arabitol, mannitol, sorbitol, sucrose or glucose.
  • Methylene bisacrylahiide is a preferred cross-linking agent.
  • the homopolymer is preferably used in the form of a non-aqueous polymer dispersion which should not have a polymer content below 30% by weight.
  • Copolymers with monomer units of the formula (I) preferably contain, as nonionic monomer units, acrylamide, methacrylamide, C 4 alkyl acrylate and C 4 alkyl methacrylate.
  • nonionic monomers acrylamide is particularly preferred.
  • these copolymers can also be crosslinked.
  • a preferred copolymer is the crosslinked acrylamide-methacryloyloxyethyltrimethylammonium chloride copolymer, in particular in a weight ratio of about 20:80.
  • Celquat ® and Polymer JR ® Quaternized cellulose derivatives, as are commercially available under the names Celquat ® and Polymer JR ® .
  • the compounds Celquat ® H 100, Celquat ® L 200 and Polymer JR ® 400 are preferred quaternized cellulose derivatives,
  • - polysiloxanes with quaternary groups which are particularly preferred conditioning agents, such as the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized Trimethylsilylamo- dimethicone), Dow Corning ® 929 Emulsion (containing a hydroxylamino-modified Silicon, which is also known as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th. Goldschmidt), diquaternary polydimethylsiloxanes, quaternium -80)
  • Q2-7224 commercially available products
  • Dow Corning a stabilized Trimethylsilylamo- dimethicone
  • Dow Corning ® 929 Emulsion containing a hydroxylamino-modified Silicon, which is also known as amodimethicone
  • SM-2059 manufactured
  • polymeric dimethyldiallylammonium salts and their copolymers with esters and amides of acrylic acid and methacrylic acid for example Merquat ® 100 (poly (dimethyldiallylammonium chloride)) and Merquat ® 550 (dimethyldiallylammonium chloride-acrylamide copolymer), - Copolymers of vinyl pyrrolidone, in particular with quaternized derivatives of dialkylaminoalkyl acrylate and methacrylate, such as, for example, with
  • Polyquaternium 18, Polyquaternium 24 and Polyquaternium 27 known polymers with quaternary nitrogen atoms in the main polymer chain
  • the preferred anionic polymers predominantly contain carboxylate and / or sulfonate groups.
  • corresponding anionic monomers are acrylic acid, methacrylic acid, crotonic acid, maleic anhydride and 2-acrylamido-2-methylpropane sulfonic acid, which can be present in whole or in part as sodium, potassium, ammonium, mono- or triethanolammonium salt.
  • Preferred monomers are 2-acrylamido-2-r ⁇ ethylpropansulfonkla and acrylic acid (for example, as Rheotik ® 11-80 commercially available).,.
  • copolymers of at least one anionic monomer and at least one nonionic monomer are preferred.
  • anionic monomers reference is made to the substances listed above.
  • Preferred nonionic monomers are acrylamide, methacrylamide, acrylic acid ester, methacrylic acid ester, vinyl pyrrolidone, vinyl ether and vinyl ester.
  • Preferred anionic copolymers are acrylic acid-acrylamide copolymers and in particular polyacrylamide copolymers with monomers containing sulfonic acid groups. These copolymers can also be crosslinked, the crosslinking agents used preferably being polyolefinically unsaturated compounds such as tetraallyloxyethane, allyl sucrose, allylpentaerythritol and methylene bisacrylamide. Also preferred anionic homopolymers are uncrosslinked and crosslinked polyacrylic acids. Allyl ethers of pentaerythritol, sucrose and propylene can be preferred crosslinking agents (available under the Carbopol ® brand, for example).
  • Ampho-polymers are also suitable as conditioning agents.
  • amphoteric polymers are amphoteric polymers, i. H. Polymers which contain both free amino groups and free -COOH or SOaH groups in the molecule and are capable of forming internal salts are zwitterionic
  • An example of the present invention amphopolymer suitable is that available under the name Amphomer ® acrylic resin which is a copolymer of ethyl methacrylate tert-butylamino, N- (1, 1,3,3-tetramethylbutyl) -acrylamide and two or more monomers from the group Acrylic acid, methacrylic acid and their simple esters.
  • amphopolymers are composed of unsaturated carboxylic acids (e.g. acrylic and methacrylic acid), cationically derivatized unsaturated carboxylic acids (e.g. acrylamidopropyl-trimethyl-ammonium chloride) and optionally other ionic or nonionic monomers, as for example in German Laid-open specification 39 29 973 and the state of the art cited therein.
  • unsaturated carboxylic acids e.g. acrylic and methacrylic acid
  • cationically derivatized unsaturated carboxylic acids e.g. acrylamidopropyl-trimethyl-ammonium chloride
  • optionally other ionic or nonionic monomers as for example in German Laid-open specification 39 29 973 and the state of the art cited therein.
  • Terpolymers of acrylic acid, methyl acrylate and methacrylamidopropyltrimonium chloride as are commercially available under the name Merquat ® 2001 N and the commercial
  • Copolymers of maleic anhydride and methyl vinyl ether, especially those with crosslinks, are also very suitable polymers (for example Stabileze ® QM crosslinked with 1, 9-decadienes).
  • nonionic polymers can be contained in all aqueous preparations of the process according to the invention. It may be preferred to use this in the fixation (C). .
  • Suitable nonionic polymers are, for example:
  • Vinylpyrrolidone / Vinylester copolymers for example, Luviskol ® (BASF), cellulose ethers such as hydroxypropyl cellulose, hydroxyethyl cellulose and methyl hydroxypropylcellulose,
  • siloxanes are suitable, non-volatile siloxanes being understood to mean those compounds whose boiling point at normal pressure is above 200 ° C.
  • Preferred siloxanes are polydialkylsiloxanes, such as, for example, polydimethylsiloxane, polyalkylarylsiloxanes, such as, for example, polyphenylmethylsiloxane, ethoxylated polydialkylsiloxanes and polydialkylsiloxanes which contain amine and / or hydroxyl groups.
  • the preparations used contain several, in particular two different polymers of the same charge and / or each contain an ionic and an amphoteric and / or nonionic polymer.
  • the polymers are preferably present in the agents used according to the invention in amounts of 0.05 to 10% by weight, based on the total agent. Amounts from 0.1 to 5, in particular from 0.1 to 3% by weight are particularly preferred.
  • 2-pyrrolidinone-5-carboxylic acid and / or its derivatives can be used in the preparations of the process according to the invention.
  • Preferred are the sodium, potassium, calcium, magnesium or ammonium salts, in which the ammonium ion, in addition to hydrogen, has one to three C 1 -C 4 -alkyl groups wearing.
  • the sodium salt is very particularly preferred.
  • the amounts used in the agents used according to the invention are 0.05 to 10% by weight, based on the total agent, particularly preferably 0.1 to 5 and in particular 0.1 to 3% by weight.
  • vitamins, provitamins and vitamin precursors and their derivatives has also proven to be advantageous.
  • Vitamins, pro-vitamins and vitamin precursors which are usually assigned to groups A, B, C, E, F and H are preferred.
  • vitamin A includes retinol (vitamin Ai) and 3,4-didehydroretinol (vitamin A 2 ).
  • the ß-carotene is the provitamin of retinol.
  • Possible vitamin A components are, for example, vitamin A acid and its esters, vitamin A aldehyde and vitamin A ⁇ alcohol and its esters such as palmitate and acetate.
  • the preparations used according to the invention preferably contain the vitamin A component in amounts of 0.05 to 1% by weight, based on the overall preparation.
  • the vitamin B group or the vitamin B complex include u. a.
  • Vitamin B 2 (riboflavin)
  • nicotinic acid and nicotinamide are often listed under this name. According to the invention, preference is given to nicotinic acid amide, which is preferably present in the agents used according to the invention in amounts of 0.05 to 1% by weight, based on the total agent.
  • panthenol and / or pantolactone is preferably used.
  • Derivatives of panthenol which can be used according to the invention are, in particular, the esters and ethers of panthenol and cationically derivatized panthenols. Individual representatives are, for example, panthenol triacetate, the panthe- nolmonoethyl ether and its monoacetate and the cationic panthenol derivatives disclosed in WO 92/13829.
  • the compounds of the vitamin Bs type mentioned are preferably present in the agents used according to the invention in amounts of 0.05 to 10% by weight, based on the total agent. Amounts of 0.1 to 5% by weight are particularly preferred.
  • Vitamin B ⁇ (pyridoxine and pyridoxamine and pyridoxal),
  • Vitarnin C is preferably used in the agents used according to the invention in amounts of 0.1 to 3% by weight, based on the total agent.
  • Use in combination with tocopherols may also be preferred.
  • Tocopherols especially tocopherol.
  • Tocopherol and its derivatives which include in particular the esters such as acetate, nicotinate, phosphate and succinate, are preferably present in the agents used according to the invention in amounts of 0.05 to 1% by weight, based on the agent as a whole ,
  • vitamin F usually means essential fatty acids, in particular linoleic acid, linolenic acid and arachidonic acid.
  • Vitamin H is the compound (3aS, 4S, 6aR) -2-oxohexa- hydrothienol [3,4-d] imidazole-4-valeric acid, for which the trivial name biotin has now become established.
  • Biotin is contained in the agents used according to the invention preferably in amounts of 0.0001 to 1.0% by weight, in particular in amounts of 0.001 to 0.01% by weight.
  • the preparations used according to the invention preferably contain vitamins, provitamins and vitamin precursors from groups A, B, E and H.
  • Panthenol, pantolactone, pyridoxine and its derivatives as well as nicotinamide and biotin are particularly preferred.
  • plant extracts and mixtures thereof can be used in the preparations of the method according to the invention. Especially for them
  • the extracts from chamomile, witch hazel, green tea, almond, aloe vera, coconut, mango, apricot, lime, wheat, kiwi, linden flowers and melon are suitable for use in accordance with the invention.
  • the extracts are generally produced. by extracting individual parts of plants or the entire plant. Water, alcohols and mixtures thereof can be used as extractants. Among the alcohols, ethanol and isopropanol, but especially polyhydric alcohols such as ethylene glycol and propylene glycol, are preferred. Plant extracts based on water / propylene glycol in a ratio of 1:10 to 10: 1 have proven to be particularly suitable.
  • the plant extracts can be used both in pure and in diluted form.
  • aqueous preparations can be surface-active compounds, in particular those from the group of anionic, amphoteric, zwitterionic and / or nonionic surfactants.
  • surfactants is understood to mean surface-active substances which form adsorption layers on surfaces and interfaces or which can aggregate in volume phases to form micelle colloids or lyotropic mesophases.
  • Suitable anionic surfactants in preparations used according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by an anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 8 to 30 carbon atoms.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • anionic surfactants are, in each case in the form of the sodium, potassium and ammonium and the mono-, di- and trialkanolammonium salts with 2 to 4 carbon atoms in the alkanol group, - linear and branched fatty acids with 8 to 30 carbon atoms.
  • Atoms (soaps), Ether carboxylic acids of the formula R-0- (CH 2 -CH 2 0) x -CH 2 -COOH, in which R is a linear alkyl group with 8 to 30 C atoms and x 0 or 1 to 16
  • acyl sarcosides acyl taurides or acyl isethionates with 8 to 24 carbon atoms in the acyl group,
  • Alpha-sulfofatty acid methyl esters of fatty acids with 8 to 30 C atoms, alkyl sulfates and alkyl polyglycol ether sulfates of the formula R-0 (CH 2 -CH 2 0) x - OS0 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 addition products of about 2-15 molecules of ethylene oxide and / or propylene oxide onto fatty alcohols with 8 to 22 carbon atoms, alkyl and / or alkenyl ether phosphates of the formula, monoglyceride sulfates and monoglyceride ether sulfates of the formula (III)
  • R 8 CO stands for a linear or branched acyl radical with 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 stands for an alkali or alkaline earth metal.
  • 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 with sulfur trioxide or chlorosulfonic acid in the form of their sodium salts.
  • Monoglyceride sulfates of the formula (III) are preferably used, in which R 8 CO stands for a linear acyl radical having 8 to 18 carbon atoms.
  • R 7 CO (AlkO) n S ⁇ 3 M in which R 7 CO- for a linear or branched, aliphatic, saturated and / or unsaturated acyl radical with 6 to 22 carbon atoms, alk for CH 2 CH 2 , CHCH 3 CH 2 and / or CH 2 CHCH 3 , n is a number from 0.5 to 5 and M is a cation, as described in DE-OS 197 36 906.5,
  • 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, sulfosuccinic acid and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid monoalkyl polyoxyethyl esters with 8 to 18 C atoms in the alkyl group and 1 to 6 oxyethyl groups, monoglycer disulfates, alkyl and alkenyl ether phosphates and
  • Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one -COO H or -SOs ⁇ group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyl 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 acid amide derivative known under the INCI
  • Ampholytic surfactants are surface-active compounds which, in addition to a C 8 -C 24 -alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H group in the molecule and are capable of forming internal salts are.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkynaminopropionic acids and alkylamino acetic acids 8 with f ⁇ up to 24 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are the N-coconut alkyl aminopropionate, the coconut acylaminoethyl aminopropionate and the C 12 -C 8 -acyl sarcosine.
  • Nonionic surfactants contain e.g. a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether groups. Such connections are, for example
  • R 4 is an alkyl or alkenyl radical having 4 to 22 carbon atoms
  • G is a sugar radical having 5 or 6 carbon atoms
  • p is a number from 1 to 10 which can be obtained by the process known in the literature.
  • the alkyl and alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably from glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
  • the index number p in the general formula (VI) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10.
  • the value p for a certain alkyl oligoglycoside is an analytically determined arithmetic parameter, which usually represents a fractional number.
  • Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, preference is given to those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.
  • the alkyl or alkenyl radical R 15 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and their technical mixtures, which can be obtained as described above.
  • Alkyl oligoglucosides based on hardened Ci 2 / i 4 coco alcohol with a DP of 1 to 3 are preferred.
  • R 5 CO is an aliphatic acyl radical having 6 to 22 carbon atoms
  • R 6 is hydrogen
  • [Z] is a linear one or branched polyhydroxyalkyl radical having 3 to 12 carbon atoms and 3 to 10 hydroxyl groups.
  • the fatty acid N-alkyl polyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • the fatty acid N-alkylpolyhydroxyalkylamides are derived from reducing sugars with 5 or 6 carbon atoms, in particular from glucose.
  • the preferred fatty acid N-alkylpolyhydroxyalkylamides are therefore fatty acid N-alkylglucamides as represented by the formula (VII):
  • the preferred fatty acid N-alkylpolyhydroxyalkylamides used are glucamides of the formula (VII) in which R 8 is hydrogen or an alkyl group and R 7 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, Isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid or, erucic acid or their technical mixtures.
  • R 8 is hydrogen or an alkyl group
  • R 7 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, Isostearic acid, oleic acid, elaidic acid,
  • Fatty acid N-alkylglucamides of the formula (VII) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C12 / 14 coconut fatty acid or a corresponding derivative are particularly preferred.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • the branched alkyl radical R preferably contains 6 to 22 carbon atoms. Primary linear and methyl-branched aliphatic radicals in the 2-position are particularly preferred. Examples of such alkyl radicals are 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. 1-Octyl, 1-decyl, 1-lauryl, 1-myristyl are particularly preferred.
  • nonionic surfactants are the sugar surfactants. These can be in the agents used according to the invention preferably in amounts of 0.1 to 20% by weight. Amounts from 0.5 'to 15% by weight are preferred, and particularly preferably from 0.5 to 7.5% by weight.
  • the surfactants are used in amounts of 0.1 to 45% by weight, preferably 0.5 to 30% by weight and very particularly preferably 0.5 to 25% by weight.
  • Emulsifiers are preferably used in the preparations of the method according to the invention.
  • Emulsifiers cause water or oil-stable adsorption layers to form at the phase interface, which protect the dispersed droplets against coalescence and thus stabilize the emulsion.
  • An emulsion is to be understood as a droplet-like distribution (dispersion) of a liquid in another liquid with the expenditure of energy in order to create stabilizing phase interfaces by means of surfactants.
  • the selection of these emulsifying surfactants or emulsifiers is based on the substances to be dispersed and the particular external phase as well as the fine particle size of the emulsion.
  • Emulsifiers which can be used according to the invention are, for example
  • alkyl (oligo) glucosides for example the commercially available product Montanov ® 68,
  • Partial esters of polyols with 3 to 6 carbon atoms with saturated fatty acids with 8 to 22 C atoms, - sterols are understood to be a group of steroids which carry a hydroxyl group on the C atom 3 of the steroid structure and both from animal tissue (zoosterols such as lanosterol and cholesterol) and from vegetable fats (phytosterols, for example ergosterol, stigmasterol and sitosterol) be isolated. Sterols, the so-called mycosterols, are also isolated from fungi and yeasts.
  • glucose phospholipids include primarily the glucose phospholipids, e.g. as lecithins or phosphatidylcholines from e.g. Egg yolks or plant seeds (e.g. soybeans) are understood.
  • Fatty acid esters of sugars and sugar alcohols such as sorbitol
  • Polyglycerols and polyglycerol derivatives such as, for example, polyglycerol poly-12-hydroxystearate,
  • the agents used according to the invention preferably contain the emulsifiers in amounts of 0.1 to 25% by weight, in particular 0.1 to 3% by weight, based on the total agent.
  • compositions used according to the invention can preferably contain at least one nonionic emulsifier with an HLB value of 8 to 18, according to the 10th edition, Georg Thieme Verlag Stuttgart, New York, in Römpp Lexikon Chemie (Ed. J. Falbe, M. Regitz) , (1997), page 1764.
  • Nonionic emulsifiers with an HLB value of 10 to 15 can be particularly preferred according to the invention.
  • the fixing agents (C) used according to the invention contain oxidizing agents, for example sodium bromate, potassium bromate, hydrogen peroxide and the stabilizers customary for stabilizing aqueous hydrogen peroxide preparations.
  • oxidizing agents for example sodium bromate, potassium bromate, hydrogen peroxide and the stabilizers customary for stabilizing aqueous hydrogen peroxide preparations.
  • the pH of such aqueous H 0 2 preparations which usually contain about 0.5 to 15% by weight, usually about 0.5 to 3% by weight, H 2 O 2 ready for use, is preferably 2 to 6, in particular 2 to 4; it is adjusted by acids, preferably phosphoric acid, phosphonic acids and / or dipicolinic acid.
  • the method according to the invention is possible and it may be preferred to use a larger volume of the preparation (C) with comparatively lower H 2 0 2 concentrations, in particular in the range from 0.5 to 1.5% by weight, of the required amount of H 2 0 2 .-% to use.
  • 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. According to the invention, the use of fixative concentrates which are diluted with water before use can be particularly preferred.
  • oxidation with the aid of enzymes, where "the enzymes both to produce oxidizing per compounds are used as well as to enhance the effect of a small amount of oxidizing agents, or enzymes are used, the electrons from suitable developer Components (reducing agents) to atmospheric oxygen, preferably oxidases such as tyrosinase, ascorbate oxidase and laccase, but also glucose oxidase, uricase or pyruvate oxidase, and the procedure, the effect of small amounts (eg 1% and less) of hydrogen peroxide amplified by peroxidases.
  • oxidases such as tyrosinase, ascorbate oxidase and laccase, but also glucose oxidase, uricase or pyruvate oxidase
  • the fixatives can of course also be formulated as solids. They then contain the oxidizing agent in the form of a solid, e.g. Potassium or sodium bromate and water and / or nourishing ingredients are added shortly before use. It is also possible and preferred to formulate the oxidizing agent as a two-component system. The two components, one of which is preferably a hydrogen peroxide solution or an aqueous solution of another oxidizing agent and the other of which contains the other constituents, in particular caring substances and / or reducing agents, are then mixed only shortly before use.
  • hydroxycarboxylic acids and in particular the dihydroxy, trihydroxy and polyhydroxycarboxylic acids and also the dihydroxy, trihydroxy and polyhydroxydi, tri and polycarboxylic acids in the fixation (C). It has been shown that in addition to the Hydroxycarboxylic acids, the hydroxycarboxylic acid esters and the mixtures of hydroxycarboxylic acids and their esters as well as polymeric hydroxycarboxylic acids and their esters can be very particularly preferred.
  • Preferred hydroxycarboxylic acid esters are, for example, full esters of glycolic acid, lactic acid, malic acid, tartaric acid or citric acid.
  • hydroxycarboxylic acid esters are esters of ⁇ -hydroxypropionic acid, tartronic acid, D-gluconic acid, sugar acid, mucic acid or glucuronic acid.
  • Suitable alcohol components of these esters are primary, linear or branched aliphatic alcohols with 8-22 C atoms, for example fatty alcohols or synthetic fatty alcohols.
  • the esters of Ci 2 -C 5 fatty alcohols are particularly preferred. Esters of this type are commercially available, for example under the brand Cosmacol® ® EniChem, Augusta Industriale.
  • Particularly preferred polyhydroxy polycarboxylic acids are polylactic acid and poly-tartaric acid and their esters. ⁇
  • the fixing agents can contain, as surface-active compounds, cationic surfactants of the quaternary ammonium compound, esterquat and amidoamine type.
  • 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 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.
  • Esterquats 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.
  • the alkylamidoamines are usually produced by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
  • the stearamidopropyldimethylamine available as Tegoamid ® S 18 is particularly suitable.
  • the agents used according to the invention preferably contain the cationic surfactants in amounts of 0.05 to 10% by weight. Amounts of 0.1 to 5% by weight are particularly preferred.
  • Suitable conditioning agents in all agents used according to the invention are: silicone oils and silicone gums, in particular dialkyl and alkylarylsiloxanes, such as, for example, dimethylpolysiloxane and methylphenylpolysiloxane, and their alkoxylated and quaternized analogs.
  • silicones are the Dow Corning under the names DC 190, DC 200 and DC 1401 products sold and the commercial product Fancorsil ® LIM first
  • a suitable anionic silicone oil is the product Dow Corning ® 1784.
  • Thickeners such as 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 such. B. bentonite or fully synthetic hydrocolloids such.
  • Solvents and intermediates such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol,
  • active ingredients that improve fiber structure in particular mono-, di- and oligosaccharides, such as, for example, glucose, galactose, fructose, fructose and lactose, quaternized amines such as methyl 1-alkylamidoethyl-2-alkylimidazolinium methosulfate,
  • anti-dandruff agents such as piroctone olamine, zinc omadine and climbazol
  • ⁇ - complexing agents such as EDTA, NTATß-alaninediacetic acid and phosphonic acids
  • - opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers
  • Pearlescent agents such as ethylene glycol mono- and distearate and PE, G-3 distearate,
  • a second object of the invention is the use of at least one protein hydrolyzate and additionally one or more amino acids in a "preparation (B) in the inventive process for the permanent deformation of keratinous fibers.
  • the invention further relates to a kit for use in a method according to the invention, which comprises at least one keratin-reducing preparation (A), one fixing preparation (C) and one preparation (B) which contains at least one protein hydrolyzate and additionally one or more amino acids, exists, the preparations being packed separately.
  • the hair cross sections for 40 moistened individual hairs (type: Natural dark brown; code # 6634, Alkinco) were determined. The gradient was then measured in the Hook range up to 1% elongation of the untreated hair. The tensile strain measurements were carried out with a fully automatic MTT 670 from Dia Stron.
  • the waving agent A was then applied to the hair. After a contact time of 20 minutes, the hair was rinsed thoroughly with tap water for 5 minutes.
  • the care product (B) was applied to damp hair and after a contact time of 10 minutes, fixative C was applied to the hair. The hair was fixed for 10 minutes and then the hair was rinsed with water for 5 minutes. The same measurements were then carried out on the treated hair as before on the untreated hair.
  • the percentage given above indicates the percentage probability with which the series of measurements are distinguished. If the value is> 95%, the series of measurements can be regarded as significantly different.

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Abstract

L'invention concerne un procédé de mise en forme permanente de fibres kératiniques, consistant à traiter la fibre à l'aide d'une préparation aqueuse (A) d'une substance réduisant la kératine avant et/ou après une mise en forme mécanique. Après un temps de pose, la fibre est rincée à l'eau et/ou à l'aide d'un agent aqueux. Une préparation aqueuse (B) est appliquée. Après un temps de pose, ladite fibre est fixée à l'aide d'une préparation aqueuse (C) d'un agent d'oxydation, éventuellement rincée après un temps de pose et éventuellement retraitée, ladite préparation (B) contenant au moins un hydrolysat de protéines ainsi qu'un ou plusieurs acides aminés.
PCT/EP2002/013932 2001-12-18 2002-12-09 Procede de mise en forme permanente de fibres keratiniques et agents WO2003051320A1 (fr)

Priority Applications (2)

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AU2002361993A AU2002361993A1 (en) 2001-12-18 2002-12-09 Method for the permanent deformation of keratin fibres, and agent
EP02796590A EP1463484A1 (fr) 2001-12-18 2002-12-09 Procede de mise en forme permanente de fibres keratiniques et agents

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DE10162143.4 2001-12-18
DE2001162143 DE10162143A1 (de) 2001-12-18 2001-12-18 Verfahren zur dauerhaften Verformung keratinischer Fasern und Mittel

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Publication number Priority date Publication date Assignee Title
WO2008006721A1 (fr) * 2006-07-14 2008-01-17 Unilever Plc Composition de soins capillaires
WO2012027369A3 (fr) * 2010-08-23 2013-03-21 Diversapack Of California, Llc Système et procédé de lissage ou de mise en forme des cheveux
FR3009785A1 (fr) * 2013-08-22 2015-02-27 Marcel Georges Cohen Composition cosmetique de lissage, ensemble et utilisation associes.

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GB2160419A (en) * 1984-06-08 1985-12-24 Crestol Ltd Treatment of hair, skin and nails
EP0186025A2 (fr) * 1984-12-17 1986-07-02 Henkel Kommanditgesellschaft auf Aktien Préparations cosmétiques contenant un hydrolysat de protéine d'amandes
WO1993000882A1 (fr) * 1991-07-08 1993-01-21 R.M. Walker Healthcare Products, Inc. Produit de rinçage neutralisant et procede ameliore d'assouplissement chimique des cheveux
DE19633112A1 (de) * 1996-08-16 1998-02-19 Goldwell Gmbh Dauerwellmittel und Fixiermittel für Dauerwellen
WO1998051265A1 (fr) * 1997-05-16 1998-11-19 L'oreal Composition pour traitement capillaire
WO1999058099A2 (fr) * 1999-07-03 1999-11-18 Hans Schwarzkopf Gmbh & Co. Kg Procede pour l'ondulation permanente de fibres keratiniques, et produits
DE19835327A1 (de) * 1998-08-05 2000-02-10 Henkel Kgaa Haarbehandlungsmittel

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DE4436065A1 (de) * 1994-10-10 1996-04-11 Henkel Kgaa Mittel und Verfahren zur dauerhaften Verformung von Keratinfasern
JPH08301732A (ja) * 1995-05-08 1996-11-19 Hoyu Co Ltd パーマネントウェーブ用剤組成物
DE19855606A1 (de) * 1998-12-02 2000-06-08 Schwarzkopf Gmbh Hans Mittel zur dauerhaften Verformung keratinischer Fasern

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GB2160419A (en) * 1984-06-08 1985-12-24 Crestol Ltd Treatment of hair, skin and nails
EP0186025A2 (fr) * 1984-12-17 1986-07-02 Henkel Kommanditgesellschaft auf Aktien Préparations cosmétiques contenant un hydrolysat de protéine d'amandes
WO1993000882A1 (fr) * 1991-07-08 1993-01-21 R.M. Walker Healthcare Products, Inc. Produit de rinçage neutralisant et procede ameliore d'assouplissement chimique des cheveux
DE19633112A1 (de) * 1996-08-16 1998-02-19 Goldwell Gmbh Dauerwellmittel und Fixiermittel für Dauerwellen
WO1998051265A1 (fr) * 1997-05-16 1998-11-19 L'oreal Composition pour traitement capillaire
DE19835327A1 (de) * 1998-08-05 2000-02-10 Henkel Kgaa Haarbehandlungsmittel
WO1999058099A2 (fr) * 1999-07-03 1999-11-18 Hans Schwarzkopf Gmbh & Co. Kg Procede pour l'ondulation permanente de fibres keratiniques, et produits

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008006721A1 (fr) * 2006-07-14 2008-01-17 Unilever Plc Composition de soins capillaires
WO2012027369A3 (fr) * 2010-08-23 2013-03-21 Diversapack Of California, Llc Système et procédé de lissage ou de mise en forme des cheveux
FR3009785A1 (fr) * 2013-08-22 2015-02-27 Marcel Georges Cohen Composition cosmetique de lissage, ensemble et utilisation associes.

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AU2002361993A1 (en) 2003-06-30
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