WO1999018917A2 - Agent de coloration pour fibres a base de keratine, a teneur en acide dehydroascorbique - Google Patents

Agent de coloration pour fibres a base de keratine, a teneur en acide dehydroascorbique Download PDF

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Publication number
WO1999018917A2
WO1999018917A2 PCT/EP1998/006310 EP9806310W WO9918917A2 WO 1999018917 A2 WO1999018917 A2 WO 1999018917A2 EP 9806310 W EP9806310 W EP 9806310W WO 9918917 A2 WO9918917 A2 WO 9918917A2
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WIPO (PCT)
Prior art keywords
amino
acid
hydroxy
group
compounds
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PCT/EP1998/006310
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German (de)
English (en)
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WO1999018917A3 (fr
Inventor
Hinrich Möller
Horst Höffkes
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Henkel Kommanditgesellschaft Auf Aktien
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Priority to AU11500/99A priority Critical patent/AU1150099A/en
Priority to EP98954334A priority patent/EP1028695A1/fr
Priority to JP2000515555A priority patent/JP2001519372A/ja
Publication of WO1999018917A2 publication Critical patent/WO1999018917A2/fr
Publication of WO1999018917A3 publication Critical patent/WO1999018917A3/fr

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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
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/62—Three oxygen atoms, e.g. ascorbic acid
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/14—Wool
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts

Definitions

  • the invention relates to an agent for dyeing keratin-containing fibers, which contains dehydroascorbic acid in combination with reactive components, the use of this agent for dyeing keratin-containing fibers and a method for dyeing keratin-containing fibers.
  • keratin fibers e.g. B. hair, wool or fur
  • direct dyes or oxidation dyes which are formed by oxidative coupling of one or more developer components with one another or with one or more coupler components
  • Coupler and developer components are also referred to as oxidation dye precursors.
  • Primary aromatic amines with a further free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and their derivatives are usually used as developer components.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components.
  • Suitable coupler substances are in particular ⁇ -naphthol, 1, 5-, 2,7- and 1, 7-dihy- droxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4-diaminophenoxyethanol, 1-phenyl-3-methyl-pyrazolone-5, 2,4-dichloro- 3-aminophenol, 1,3-bis (2,4-diaminophenoxy) propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol and 5-me- thylresorcino
  • oxidation dyes can be achieved with oxidation dyes, but the development of the color generally takes place under the influence of oxidizing agents such as H 2 O 2 , which in some cases can damage the fibers. Furthermore, some oxidation dye precursors or certain mixtures of oxidation dye precursors can sometimes have a sensitizing effect on people with sensitive skin. Direct dyes are applied under gentler conditions, but their disadvantage is that the dyeings often have inadequate fastness properties.
  • the object of the present invention is to provide colorants for keratin fibers, in particular human hair, which are qualitatively at least equivalent in terms of color depth, gray coverage and fastness properties to conventional oxidation hair colorants, but without being dependent on oxidizing agents such as H 2 O 2 .
  • Another object of the present invention is to provide colorants with which a wide variety of color shades can be obtained. Staining of the skin areas should be avoided if possible.
  • the colorants may have no or only a very low sensitization potential.
  • combinations of dehydroascorbic acid and at least one other component are outstandingly suitable for dyeing fibers containing keratin.
  • the agents result in colorations with excellent brilliance and depth of color and lead to a variety of color nuances.
  • the use of oxidizing agents is not necessary, but should not be excluded in principle.
  • the present invention accordingly relates to an agent for dyeing keratin-containing fibers
  • a primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, ⁇ - to ⁇ -amino acids, oligopeptides and aromatic hydroxy compounds composed of 2 to 9 amino acids, and / or at least one CH active connection.
  • Keratin-containing fibers are wool, furs, feathers and in particular human hair.
  • the colorants according to the invention can also be used to dye other natural fibers, such as cotton, jute, sisal, linen or silk, modified natural fibers such as regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose and synthetic fibers such as polyamide, Polyacrylonitrile, polyurethane and polyester fibers can be used.
  • the compositions according to the invention preferably contain the compounds of components A and B in an amount of 0.03 to 65, in particular 1 to 40 mmol, in each case based on 100 g of the total colorant.
  • the present invention also includes those embodiments which contain reaction products of the individual components A and B.
  • dehydroascorbic acid contained as component A is a known compound, the preparation of which is described in the literature and which is commercially available.
  • Suitable compounds with a primary or secondary amino group as component B are, for example, primary aromatic amines such as N, N-dimethyl, N, N-diethyl, N- (2-hydroxyethyl) -N-ethyl, N, N-bis - (2-hydroxyethyl) -, N- (2-methoxyethyl-), 2,3-, 2,4-, 2,5-dichloro-p-phenylenediamine, 2-chloro-p-phenylenediamine, 2,5-dihydroxy -4-morpholinoaniline dihydrobromide, 2-, 3-, 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, o-, p-phenylenediamine, o-toluenediamine, 2, 5-diaminotoluene, phenol, phenethole, 4-amino-3-methylphenol, 2- (2,5-diaminophenyl)
  • R 1 represents a hydroxyl or an amino group which may be substituted by C M alkyl, C 1-4 hydroxy alkyl or C ⁇ alkoxy-C ⁇ alkyl,
  • R 2 , R 3 , R 4 , R 5 and R 6 represent hydrogen, a hydroxy or an amino group, which are substituted by a C 1-4 alkyl, C 1-4 hydroxyalkyl, C 1-4 aminoalkyl or C ⁇ -alkoxy-C M -alkyl group can be substituted, represent a carbon or sulfonic acid group, and
  • Z for a direct bond, a saturated or unsaturated carbon chain with 1 to 4 carbon atoms, optionally substituted by hydroxy groups, a carbonyl, sulfonyl or imino group, an oxygen or sulfur atom, or a group with the
  • Y is a direct bond, a CH 2 or CHOH group
  • Suitable nitrogen-containing heterocyclic compounds are e.g. 2-, 3-, 4-amino, 2-amino-3-hydroxy, 2,6-diamino, 2,5-diamino, 2,3-diamino, 2-dimethylamino-5-amino, 2-methylamino-3-amino-6-methoxy-, 2,3-diamino-6-methoxy-, 2,6-dimethoxy-3,5-diamino-, 2,4,5-triamino-, 2,6- Dihydroxy-3,4-dimethylpyridine, 2,4-dihydroxy-5,6-diamino-, 4,5,6-triamino-, 4-hydroxy-2,5,6-triamino-, 2-hydroxy-4,5 , 6-triamino-, 2,4,5,6-tetraamino-, 2-methylamino-4,5,6-triamino-, 2,4-, 4,5-diamino-, 2-amino-4-methoxy- 6-
  • Preferred amino acids are all naturally occurring and synthetic ⁇ -amino acids, e.g. obtained by hydrolysis from vegetable or animal proteins, e.g. Collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein, accessible amino acids. Both acidic and alkaline amino acids can be used. Preferred amino acids are arginine, histidine, tyrosine, phenylalanine, DOPA (dihydroxyphenylalanine), omithin, lysine and tryptophan. But also other amino acids, e.g. 6-aminocaproic acid can be used.
  • the oligopeptides can be naturally occurring or synthetic oligopeptides, but also the oligopeptides contained in polypeptide or protein hydrolyzates, provided that they have sufficient water solubility for use in the colorants according to the invention.
  • examples include glutathione or those in the hydrolysates of collagen, keratin, casein, elastin, soy protein, wheat gluten or To name almond protein contained oligopeptides.
  • Use together with compounds having a primary or secondary amino group or with aromatic hydroxy compounds is preferred.
  • Suitable aromatic hydroxy compounds are e.g. 2-, 4-, 5-methylresorcinol, 2,5-dimethylresorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucin, hydroxyhydroquinone, 2-, 3-, 4-methoxy, 3-dimethylamino, 2- (2-hydroxyethyl) -, 3,4-methylenedioxyphenol, 2,4-, 3,4-dihydroxybenzoic acid, -phenylacetic acid, gallic acid, 2,4,6-trihydroxybenzoic acid, -acetophenone, 2-, 4-chlororesorcinol , 1-naphthol, 1, 5-, 2,3-, 2,7-dihydroxynaphthalene, 6-dimethylamino-4-hydroxy-2-naphthalenesulfonic acid, 3,6-dihydroxy-2,7-naphthalenesulfonic acid.
  • CH-active compounds which may be mentioned are 1, 2,3,3-tetramethyl-3H-indolium iodide, 1, 2,3,3-tetramethyl-3H-indolium-p-toluenesulfonate, 1,2,3,3-tetrams - 3H-indolium methanesulfonate, Fischer's base (1,3,3-trimethyl-2-methyleneindoline), 2,3-dimethyl-benzothiazolium iodide, 2,3-dimethyl-benzothiazolium p-toluenesulfonate, rhodanine, rhodanine -3-acetic acid, 1-ethyl-2-quinaldinium iodide, 1-methyl-2-quinaldinium iodide, barbituric acid, thiobarbituric acid, 1, 3-dimethylthiobarbituric acid, diethylthiobarbituric acid, oxindole, 3-
  • coloring substances can also be used together in all coloring agents; Likewise, several different components from the groups of compounds having a primary or secondary amino group, nitrogen-containing heterocycles, aromatic hydroxy compounds or amino acids can also be used together.
  • alkali metal salts or ammonium salts of C Ce carboxylic acids or C Ce hydroxy carboxylic acids and carbonic acid to the agent according to the invention.
  • Examples of such salts are formate, acetate, propionate, butyrate, valerate, capronate, glycolate, lactate and carbonate.
  • Hydroxyalkylammonium cations can also be used as ammonium cations.
  • the presence of oxidizing agents, for example H 2 O 2 can be dispensed with when using dehydroascorbic acid according to the invention.
  • Oxidizing agents are generally used in an amount of 0.01 to 6% by weight, based on the application solution.
  • a preferred oxidizing agent for human hair is H 2 O 2 .
  • the colorants according to the invention result in a wide range of color shades in the range from yellow to yellow-brown, orange, brown-orange, medium brown, dark brown, violet, dark violet to black; the fastness properties are excellent, the sensitization potential is very low.
  • the colorants according to the invention contain, in addition to the compounds contained according to the invention, customary direct dyes, e.g. from the group of nitrophylenediamines, nitroaminophenols, anthraquinones or indophenols, such as e.g.
  • HC Yellow 2 under the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 6, Basic Yeliow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16 and Basic Brown 17 known compounds as well as picramic acid, 2-amino-6-chloro-4-nitrophenol, 4-amino-2-nitro- diphenylamine-2'-carboxylic acid, 6-nitro-1, 2,3,4-tetrahydroquinoxaline, 4-N-ethyl-1, 4-bis (2'-hydroxyethylamino) -2-nitrobenzene hydrochloride and 1-methyl-3 -nitro-4- (2'-hydroxyethyl) aminobenzene.
  • the agents according to the invention in accordance with this embodiment preferably contain the substantive dyes in an amount of 0.01 to 20% by weight, based on the total colorant.
  • the colorants according to the invention can also contain naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, sapwood, sage, blue wood, madder root, catechu, Sedre and alkanna root. It is not necessary that the oxidation dye precursors or the optional direct dyes each represent uniform compounds. Rather, in the colorants according to the invention, due to the production processes for the individual dyes, further components may also be present in minor amounts, provided that these do not adversely affect the coloring result or must be excluded for other reasons, for example toxicological reasons.
  • naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, sapwood, sage, blue wood, madder root, catechu, Sedre and alkanna root.
  • the colorants according to the invention produce intensive colorations even at physiologically tolerable temperatures of below 45 ° C. They are therefore particularly suitable for dyeing human hair.
  • the colorants can usually be incorporated into a water-containing cosmetic carrier.
  • Suitable water-containing cosmetic carriers are e.g. Creams, emulsions, gels or also surfactant-containing foaming solutions such as Shampoos or other preparations that are suitable for use on the keratin fibers. If necessary, it is also possible to incorporate the colorants into anhydrous carriers.
  • the colorants according to the invention can contain all active ingredients, additives and auxiliaries known in such preparations.
  • the colorants contain at least one surfactant, both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants being suitable in principle. In many cases, however, it has proven advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.
  • Suitable anionic surfactants in preparations 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 10 to 22 carbon atoms.
  • anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • 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 with 8 to 22 carbon atoms.
  • 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 in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one - COO () - or -SO 3 () 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-dimethyl ammonium glycinates, for example the cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group, and the cocoacylaminoethylhydroxyethyl carboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the CTFA name
  • Ampholytic surfactants are surface-active compounds which, in addition to a C 8-18 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.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12-18 acyl 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
  • cationic surfactants which can be used in the hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds.
  • Prefers are ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylmonium chloride and trialkylmethylammonium chlorides, e.g. B. cetyltrimethylammonium chloride, stearylrimethylammonium chloride, distearyldimethylammonium chloride,
  • the quaternized protein hydrolyzates are further cationic surfactants which can be used according to the invention.
  • cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), 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, Quaterium-80).
  • alkylamidoamines especially fatty acid amidoamines such as the stearylamidopropyldimethylamine available under the name Tego Amid®S 18, are characterized in particular by their good biodegradability.
  • quaternary sugar derivative that can be used as a cationic surfactant is the commercial product Glucquat®100, according to the CTFA nomenclature a "lauryl methyl gluceth-10 hydroxypropyl dimonium chloride".
  • the compounds with alkyl groups used as surfactants 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.
  • the surfactants which are addition products of ethylene and / or propylene oxide onto fatty alcohols or derivatives of these addition products
  • 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.
  • 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 polymers such as, for example, vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes
  • cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary polymer groups, dimethyldiallylammononyl amide , Acrylamide-dimethyl-diallylammonium chloride copolymers, with diethyl sulfate quaternized dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium-methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers / such as acrylamido-methacrylate-methylene-acrylate-methacrylate-
  • 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 dex trine, clays such as B. bentonite or fully synthetic hydrocolloids such as polyvinyl alcohol,
  • Structurants such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins, and silicone oils,
  • Protein hydrolyzates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolyzates, their condensation products with fatty acids and quaternized protein hydrolyzates, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol,
  • Anti-dandruff agents such as piroctone olamine and zinc omadine, other substances for adjusting the pH value,
  • Active ingredients such as panthenol, pantothenic acid, allantoin, pyrrolidone carboxylic acids and their salts, plant extracts and vitamins, cholesterol, light stabilizers,
  • Consistency generators such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as walrus, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters, fatty acid alkanolamides,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates, imidazoles, tannins, pyrrole, opacifiers such as latex,
  • Pearlescent agents such as ethylene glycol mono- and distearate
  • Blowing agents such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air as well as antioxidants.
  • the constituents of the water-containing carrier are used to produce the colorants according to the invention in amounts customary for this purpose;
  • emulsifiers are used in concentrations of 0.5 to 30% by weight and thickeners in concentrations of 0.1 to 25% by weight of the total colorant.
  • concentrations of 0.5 to 30% by weight are used in concentrations of 0.1 to 25% by weight of the total colorant.
  • thickeners are used in concentrations of 0.1 to 25% by weight of the total colorant.
  • ammonium or metal salts to the coloring agents.
  • Suitable metal salts are, for example, formates, carbonates, halides, sulfates, butyrates, valerates, capronates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates of alkali metals, such as potassium, sodium or lithium, alkaline earth metals, such as magnesium, Caicium, strontium or barium, or of aluminum, manganese, iron, cobalt, copper or zinc, with sodium acetate, lithium bromide, calcium bromide, calcium gluconate, zinc chloride, zinc sulfate, magnesium chloride, magnesium sulfate, ammonium carbonate, chloride and acetate being preferred.
  • These salts are preferably present in an amount of 0.03 to 65, in particular 1 to 40 mmol, based on 100 g of the total colorant.
  • the pH of the ready-to-use coloring preparations is usually between 2 and 11, preferably between 5 and 9.
  • the present invention further relates to the use of dehydroascorbic acid of the formula (I)
  • Another object of the present invention relates to a process for dyeing keratin fibers, in which a colorant containing dehydroascorbic acid and the above-mentioned compounds of component B are used as coloring components.
  • the colorants are generally applied to the hair in the presence of a water-containing cosmetic vehicle in an amount of 100 g, left there for about 30 minutes and then rinsed out or washed out with a commercially available hair shampoo.
  • the compounds of components A and B can either be applied to the hair simultaneously or in succession, it being irrelevant which of the components is applied first.
  • the optionally contained ammonium or metal salts can be added to the first or the second component. There may be an interval of up to 30 minutes between the application of the first and the second component. Pretreatment of the fibers with the saline solution is also possible.
  • Components A and B of the agents according to the invention can either be stored separately or together, either in a liquid to pasty preparation (aqueous or anhydrous) or as a dry powder. If the components are stored together in a liquid preparation, this should be largely anhydrous to reduce a reaction of the components. When stored separately, the reactive components are only intimately mixed with one another immediately before use. In dry storage, a defined amount of warm (50 to 80 ° C) water is usually added before use and a homogeneous mixture is produced.
  • a slurry of 10 mmoles of dehydroascorbic acid, 10 mmoles of a component B compound, 10 mmoles of sodium acetate and a drop of a 20% fatty alkyl ether sulfate solution in 100 ml of water was prepared.
  • the slurry was briefly heated to about 80 ° C and filtered after cooling, the pH was then adjusted to 6.
  • a strand of 90% gray, untreated human hair was placed in this coloring solution at 30 ° C. for 30 minutes.
  • the colored streak was then rinsed for 30 seconds with lukewarm water, dried in a warm (30-40 ° C.) air stream and then combed out. The colorations were then assessed visually in daylight.
  • the color depth was rated on the following scale:
  • Component B Color shade color ti «

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Abstract

L'invention concerne un agent de coloration pour fibres à base de kératine, qui contient des acides déhydroascorbiques de la formule (I) et au moins un composé ayant un groupe amino primaire ou secondaire ou un groupe hydroxy, sélectionné parmi des amines aliphatiques ou aromatiques primaires ou secondaires, des composés hétérocycliques contenant de l'azote, des aminoacides α à φ, des oligopeptides composés de 2 à 9 aminoacides et des composés hydroxy aromatiques, et/ou au moins un composé CH-actif.
PCT/EP1998/006310 1997-10-14 1998-10-05 Agent de coloration pour fibres a base de keratine, a teneur en acide dehydroascorbique WO1999018917A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU11500/99A AU1150099A (en) 1997-10-14 1998-10-05 Agent for dyeing fibers containing keratin with a concentration of dehydroascorbic acid content
EP98954334A EP1028695A1 (fr) 1997-10-14 1998-10-05 Agent de coloration pour fibres a base de keratine, a teneur en acide dehydroascorbique
JP2000515555A JP2001519372A (ja) 1997-10-14 1998-10-05 ケラチン含有繊維を染色するためのデヒドロアスコルビン酸含有組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1997145354 DE19745354A1 (de) 1997-10-14 1997-10-14 Mittel zum Färben von keratinhaltigen Fasern mit einem Gehalt an Dehydroascorbinsäure
DE19745354.6 1997-10-14

Publications (2)

Publication Number Publication Date
WO1999018917A2 true WO1999018917A2 (fr) 1999-04-22
WO1999018917A3 WO1999018917A3 (fr) 1999-06-24

Family

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PCT/EP1998/006310 WO1999018917A2 (fr) 1997-10-14 1998-10-05 Agent de coloration pour fibres a base de keratine, a teneur en acide dehydroascorbique

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Country Link
EP (1) EP1028695A1 (fr)
JP (1) JP2001519372A (fr)
AU (1) AU1150099A (fr)
DE (1) DE19745354A1 (fr)
WO (1) WO1999018917A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009010686A2 (fr) * 2007-07-09 2009-01-22 L'oreal Procede de maquillage de la peau, des levres ou des ongles utilisant un colorant obtenu par reaction d'une amine avec l'acide dehydroascorbique ou un derive monomere, polymere ou isomere
WO2011084762A2 (fr) * 2009-12-21 2011-07-14 E. I. Du Pont De Nemours And Company 2,4,5-triaminophénols et composés apparentés
WO2011084810A2 (fr) * 2009-12-21 2011-07-14 E. I. Du Pont De Nemours And Company 2,4,5-triaminophénols et composés associés
FR2967683A1 (fr) * 2010-11-24 2012-05-25 Oreal Nouveaux colorants directs a motif derive de l'acide ascorbique, composition de teinture les comprenant et procede de coloration des matieres keratiniques humaines a partir de ces colorants

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19852611C1 (de) * 1998-11-14 2000-09-07 Wella Ag Verwendung von Dehydroascorbinsäure in Fixiermitteln sowie Mittel und Verfahren zur dauerhaften Haarverformung
DE10045856A1 (de) 2000-09-14 2002-03-28 Henkel Kgaa Haarfärbemittel mit Indigoderivaten
DE10358878A1 (de) * 2003-12-16 2005-07-21 Wella Ag Mittel und Verfahren zum oxidativen Färben von Keratinfasern
JP4083702B2 (ja) * 2004-04-09 2008-04-30 ホーユー株式会社 酸化染毛剤組成物

Citations (2)

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Publication number Priority date Publication date Assignee Title
FR1338063A (fr) * 1962-10-25 1963-09-20 Interpal S A Teinture pour cheveux
US5203875A (en) * 1991-03-28 1993-04-20 L'oreal Dyeing composition for keratinous fibers, containing oxidation dye precursors and hydroxybenzofurane used as couplers, and dyeing process using these compositions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1338063A (fr) * 1962-10-25 1963-09-20 Interpal S A Teinture pour cheveux
US5203875A (en) * 1991-03-28 1993-04-20 L'oreal Dyeing composition for keratinous fibers, containing oxidation dye precursors and hydroxybenzofurane used as couplers, and dyeing process using these compositions

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009010688A3 (fr) * 2007-07-09 2009-04-23 Oreal Composition de coloration de la peau comprenant un autobronzant et un colorant obtenu par reaction d'une amine avec l'acide dehydroascorbique ou l'un de ses derives monomeres, polymeres ou isomeres
US10173080B2 (en) 2007-07-09 2019-01-08 L'oreal Dehydroascorbic acid or monomeric, polymeric or isomeric derivative thereof and an amine for artificially coloring the skin
WO2009010688A2 (fr) * 2007-07-09 2009-01-22 L'oreal Composition de coloration de la peau comprenant un autobronzant et un colorant obtenu par reaction d'une amine avec l'acide dehydroascorbique ou l'un de ses derives monomeres, polymeres ou isomeres
WO2009010686A3 (fr) * 2007-07-09 2009-04-16 Oreal Procede de maquillage de la peau, des levres ou des ongles utilisant un colorant obtenu par reaction d'une amine avec l'acide dehydroascorbique ou un derive monomere, polymere ou isomere
WO2009010684A3 (fr) * 2007-07-09 2009-04-16 Oreal Procede de coloration des matieres keratiniques humaines utilisant un ortho-diphenol et l'acide dehydroascorbique ou l'un de ses derives monomeres, polymeres ou isomeres
WO2009010685A3 (fr) * 2007-07-09 2009-04-23 Oreal Procede de coloration de la peau utilisant l'acide dehydroascorbique ou l'un de ses derives monomeres, polymeres ou isomeres et une amine
WO2009010684A2 (fr) * 2007-07-09 2009-01-22 L'oreal Procede de coloration des matieres keratiniques humaines utilisant un ortho-diphenol et l'acide dehydroascorbique ou l'un de ses derives monomeres, polymeres ou isomeres
US20100221203A1 (en) * 2007-07-09 2010-09-02 L'oreal Dehydroascorbic acid or monomeric, polymeric or isomeric derivative thereof and an amine for artificially coloring the skin
WO2009010686A2 (fr) * 2007-07-09 2009-01-22 L'oreal Procede de maquillage de la peau, des levres ou des ongles utilisant un colorant obtenu par reaction d'une amine avec l'acide dehydroascorbique ou un derive monomere, polymere ou isomere
WO2011084762A2 (fr) * 2009-12-21 2011-07-14 E. I. Du Pont De Nemours And Company 2,4,5-triaminophénols et composés apparentés
WO2011084762A3 (fr) * 2009-12-21 2011-10-06 E. I. Du Pont De Nemours And Company 2,4,5-triaminophénols et composés apparentés
WO2011084810A3 (fr) * 2009-12-21 2011-10-13 E. I. Du Pont De Nemours And Company 2,4,5-triaminophénols et composés associés
WO2011084810A2 (fr) * 2009-12-21 2011-07-14 E. I. Du Pont De Nemours And Company 2,4,5-triaminophénols et composés associés
FR2967683A1 (fr) * 2010-11-24 2012-05-25 Oreal Nouveaux colorants directs a motif derive de l'acide ascorbique, composition de teinture les comprenant et procede de coloration des matieres keratiniques humaines a partir de ces colorants
WO2012069476A1 (fr) * 2010-11-24 2012-05-31 L'oreal Nouveaux colorants directs contenant une unité à base d'acide ascorbique, composition de colorant comprenant ces derniers et procédé de coloration d'éléments humains à base de kératine à l'aide de ces colorants

Also Published As

Publication number Publication date
WO1999018917A3 (fr) 1999-06-24
JP2001519372A (ja) 2001-10-23
AU1150099A (en) 1999-05-03
DE19745354A1 (de) 1999-04-15
EP1028695A1 (fr) 2000-08-23

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