WO2000015183A1 - Produit de coloration de fibres contenant de la keratine - Google Patents

Produit de coloration de fibres contenant de la keratine Download PDF

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Publication number
WO2000015183A1
WO2000015183A1 PCT/EP1999/006525 EP9906525W WO0015183A1 WO 2000015183 A1 WO2000015183 A1 WO 2000015183A1 EP 9906525 W EP9906525 W EP 9906525W WO 0015183 A1 WO0015183 A1 WO 0015183A1
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amino
group
acid
hydroxy
methyl
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PCT/EP1999/006525
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German (de)
English (en)
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Hinrich Möller
Horst Höffkes
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Henkel Kommanditgesellschaft Auf Aktien
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Priority to AU57454/99A priority Critical patent/AU5745499A/en
Priority to JP2000569768A priority patent/JP2002524483A/ja
Priority to EP99944605A priority patent/EP1112055A1/fr
Publication of WO2000015183A1 publication Critical patent/WO2000015183A1/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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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

Definitions

  • the invention relates to an agent for dyeing keratin-containing fibers, in particular human hair, which contains 5-arylpenta-2,4-dienylcarbonyl compounds, the use of 5-arylpenta-2,4-dienylcarbonyl compounds as a coloring component in hair dye compositions and a process for dyeing fibers containing keratin, especially human hair.
  • 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 derivatives thereof are usually used as developer components.
  • Special representatives are, for example, p-phenylenediamine, p-toluenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2- (2.5 Diaminophenyl) ethanol, 2- (2,5-diaminophenoxy) ethanol, 1-phenyl-3-carboxyamido-4-amino-pyrazolon-5, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triamino-4-hydroxypyrimidine.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol dehvates, pyrazolones and m-aminophenols are generally used as coupler components.
  • Suitable coupler substances are, in particular, ⁇ -naphthol, 1, 5-, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinomino methyl ether, m-phenylenediamine, 2,4 -diaminophenoxyethanol, 1-phenyl-3- methyl-pyrazolon-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-methylresorcinol.
  • 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 at least equivalent in quality to the usual oxidation hair colorants in terms of color depth, gray coverage and fastness properties, but without being dependent on oxidizing agents such as H 2 O 2 .
  • the colorants may have no or only a very low sensitization potential.
  • the invention relates to an agent for dyeing keratin-containing fibers, in particular human hair, containing 5-arylpenta-2,4-dienylcarbonyl compounds having the formula I or their physiologically tolerable salts,
  • R 1 represents a hydrogen atom or a Crd alkyl group
  • R 2 and R 3 can be the same or different and represent a hydrogen atom, a halogen atom, a C 1 -C 4 alkyl group, C r C 4 alkoxy group, hydroxy-C r C 4 alkoxy group, a hydroxy group, nitro group, ⁇ mino group, which can be substituted by C 1 -C 4 alkyl groups or can be part of a heterocycle, or can be a C d-acyl group, it also being possible for two of the radicals together to form a fused-on benzene ring.
  • 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, e.g. Regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose and synthetic fibers such as e.g. Polyamide, polyacrylonitrile, polyurethane and polyester fibers can be used.
  • the compounds with the formula I can be used as ice and alstrans isomers.
  • the compounds of the formula I are preferably selected from the Group of the following 5-arylpenta-2,4-dienylcarbonyl compounds: 4-
  • the abovementioned 5-arylpenta-2,4-dienylcarbonyl compounds having the formula I are preferably used in the agents according to the invention in an amount of 0.03 to 65 mmol, in particular from 1 to 40 mmol, based on 100 g of the entire colorant. They can be used as substantive colorants or in the presence of oxidation dye precursors.
  • Coloring agents which contain the 5-arylpenta-2,4-dienylcarbonyl compounds having the formula I alone as the coloring component are preferably used for dyeing in the brown area. Colorings with even greater brilliance and improved fastness properties (light fastness, wash fastness, rub fastness), especially in the yellow, orange, violet, brown and black range, are achieved if the compounds of the formula I used according to the invention together with at least one further component (hereinafter referred to as component B), selected from compounds having a primary or secondary amino group or hydroxyl group, selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides and aromatic hydroxy compounds composed of 2 to 9 amino acids, and / or CH-active compounds can be used.
  • component B further component selected from compounds having a primary or secondary amino group or hydroxyl group, selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides and aromatic hydroxy compounds composed of 2
  • the above-mentioned compounds of component B can be used 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.
  • reaction products of 5-arylpenta-2,4-dienylcarbonyl compounds of the formula I with the compounds of component B mentioned, as substantive colorants.
  • reaction products can e.g. can be obtained by briefly heating the two components in stoichiometric amounts in aqueous alkali metal hydroxides, in which case they either precipitate out of the solution as a solid or are isolated therefrom by evaporation of the solution.
  • the reaction products can also be used in combination with other dyes or dye precursors.
  • 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 , - phenethol, 4-amino-3-methylphenol, 2- (2,5-dia
  • Hydroxyalkyl, C alkoxy or C 1-4 alkoxyC 1-4 alkyl groups may be substituted
  • R 4 , R 6 , R 7 , R 8 and R 9 represent hydrogen, a hydroxy or an amino group
  • C M alkyl, C 1-4 hydroxyalkyl, C 1-4 alkoxy, C 1-4 aminoalkyl or C ⁇ alkoxy-C ⁇ alkyl groups may be substituted, and
  • X 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 formula
  • R 10 is hydrogen, a C M alkyl or a hydroxyC 1-4 alkyl group, the group O- (CH 2 ) p -NH or NH- (CH 2 ) p '-O, where p and p' are 2 or 3, and o is a number from 1 to 4, such as 4,4'-diaminostilbene, 4,4'-diaminostilbene-2, 2'-disulfonic acid mono- or di-Na salt, 4-amino-4'-dimethylaminostilbene, 4,4'-diaminodiphenylmethane, -sulfide, -sulfoxide, -amine, 4,4'-diaminodiphenylamine-2-sulfonic acid , 4,4'-diaminobenzophenone, - diphenyl ether, 3,3 ', 4,4'-tetraaminodipheny
  • the abovementioned compounds can be used both in free form and in the form of their physiologically tolerable salts, in particular as salts of inorganic acids, such as hydrochloric or sulfuric acid.
  • Suitable nitrogen-containing heterocyclic compounds are, for example, 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-, 2nd -Hydroxy-4,5,6-triamino-, 2,4,5,6-tetraamino-, 2-methylamino-4,5,6-triamino-, 2,4-, 4,5-diamino-, 2-
  • Suitable aromatic hydroxy compounds are, for example, 2-, 4-, 5-methylresorcinol, 2,5-dimethylresorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucinol, 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-dihydroxynaphthal
  • CH-active compounds examples include 1,2,3,3-tetramethyl-3H-indolium iodide, 1, 2,3,3-tetramethyl-3H-indolium-p-toluenesulfonate, 1, 2,3,3-tetramethyl - 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-quinal dinium iodide, 1-methyl-2-quinal dinium iodide barbituric acid, thiobarbituric acid, 1,3-dimethylthiobarbituric acid, diethylthiobarbituric acid, oxindole, 3-in
  • 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), ornithine, 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 and the oligopeptides contained in the hydrolyzates of collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein.
  • Agents which contain the compounds of the formula I together with compounds having a primary or secondary amino group or with aromatic hydroxy compounds are preferred.
  • the compounds of component B are particularly preferably selected from the group consisting of N- (2-hydroxyethyl) -N-ethyl-, 2-chloro-p-phenylenediamine, N, N- bis (2-hydroxyethyl) -p-phenylenediamine, 4-aminophenol, p-phenylenediamine, 2- (2,5-diaminophenyl) ethanol, 2,5-diaminotoluene, 3,4-methylenedioxyaniline, 3-amino-2,4-dichloro, 2-methyl-5-amino -, 3-methyl-4-amino-, 2-methyl-5- (2-hydroxyethylamino) -, 2-methyl-5-amino-4-chloro, 6-methyl-3-amino-2-chloro, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 3,4-methylenedioxyphenol, 3,4-diaminobenzoic acid, 2,5-di
  • Oxidizing agents for example H 2 O 2
  • 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 contain, in addition to the compounds contained according to the invention, customary direct dyes, for example from the group of the nitrophenylenediamines, nitroaminophenols, anthraquinones or indophenols, such as those under the international names or trade names HC Yellow, for further modification of the color shades 2, HC Yellow 4, HC Yellow 6, Basic Yellow 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-nitrodiphenylamine-2'-carboxylic acid, 6-nitro-1, 2,3,4-tetrahydroquinoxaline, 4-N-ethyl-1,4-bis (2'-hydroxyethylamino) -2-nitrobenzen
  • 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 for other reasons, e.g. toxicological, must be excluded.
  • 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 water-free 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.
  • glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups can be in the molecule be included.
  • suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group,
  • Ether carboxylic acids of the formula RO- (CH 2 -CH 2 O) x -CH 2 -COOH, in which R is a linear alkyl group with 10 to 22 C atoms and x 0 or 1 to 16, acyl sarcosides with 10 to 18 C- Atoms in the acyl group, acyl taurides with 10 to 18 C atoms in the acyl group, acyl isethionates with 10 to 18 C atoms in the acyl group,
  • Mono and dialkyl sulfosuccinic acid with 8 to 18 carbon atoms in the alkyl group and mono alkyl polyoxyethyl sulfosuccinate with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkane sulfonates with 12 to 18 carbon atoms, linear alpha-olefin sulfonates with 12 to 18 carbon atoms, alpha-sulfofatty acid methyl ester of fatty acids with 12 to 18 carbon atoms, alkyl sulfates and alkyl polyglycol ether sulfates of the formula RO (CH 2 -CH 2 O) x -SO 3 H, in which R is a preferably linear alkyl group with 10 to 18 C atoms and x 0 or 1 to 12,
  • Esters of tartaric acid and citric acid with alcohols the addition products of about 2 to 15 molecules of ethylene oxide and / or propylene oxide to 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 the cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyl-dimethylammonium glycinate, and 2-alkyl -3-carboxymethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethyl-hydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine.
  • 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 C. 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
  • Examples of the cationic surfactants which can be used in the hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds.
  • Ammonium halides 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.
  • 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, Quaternium-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.
  • esterquats such as those sold under the trademark Stepantex ® methylhydroxyalkyldialkoyloxyalkylammonium.
  • 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 usually preferred at Production of these substances from natural vegetable or animal raw materials, so that mixtures of substances with different alkyl chain lengths depending on the respective raw material are obtained.
  • both products with a "normal” homolog distribution and those with a narrowed homolog distribution can be used.
  • “Normal” homolog distribution is understood to mean mixtures of homologs which are obtained as catalysts from the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates.
  • narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides,
  • hydroxides or alcoholates can be used as catalysts.
  • the use of products with a narrow homolog distribution can be preferred.
  • nonionic polymers such as vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes
  • cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium, dimethyldiallylammonium methyldiallylammonium chloride copolymers, diethyl sulfate-quaternized dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone
  • Imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as, for example, acrylamidopropyltrimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate / tert.-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyacrylic acids, for example, anionic polymers, such as anionic polymers , Vinyl acetate / crotonic acid copolymers, vinyl pyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / N-tert.-butylacrylamide terpolymers, Thickeners such as
  • Cellulose derivatives e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amylopectin and
  • Dextrins clays such as e.g. B. bentonite or fully synthetic hydrocolloids such as e.g.
  • Structurants such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin,
  • Protein hydrolyzates especially elastin, collagen, keratin, milk protein,
  • 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,
  • Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as whale, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether,
  • 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
  • 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.
  • Suitable metal salts are e.g. 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, calcium, 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.
  • Another object of the present invention relates to the use of 5-arylpenta-2,4-dienylcarbonyl compounds having the formula I or their physiologically tolerable salts
  • R 1 represents a hydrogen atom or a CrC ⁇ alkyl group
  • R 2 and R 3 may be the same or different and, for a hydrogen atom, a halogen atom, a C r C 4 alkyl group, C r C 4 alkoxy group, hydroxy-C r C 4 alkoxy group, a hydroxy group, nitro group, amino group, the can be substituted by C 1 -C 4 alkyl groups or can be part of a heterocycle, or can be a CC ⁇ acyl group, where two of the radicals together can form a fused-on benzene ring, as a coloring component in oxidation hair dyes.
  • Yet another object of the present invention relates to a process for dyeing keratin-containing fibers, in particular human hair, in which a colorant containing
  • R 1 represents a hydrogen atom or a CrC alkyl group
  • R 2 and R 3 may be the same or different and represent a hydrogen atom, a halogen atom, a C 1 -C 4 -alkyl group, CrOralkoxy group, hydroxy-C 1, -
  • C r C 4 alkyl groups may be substituted or may be part of a heterocycle, or may be a C C acyl group, it also being possible for two of the radicals together to form a fused-on benzene ring,
  • Hydroxyl group selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds,
  • Amino acids, oligopeptides and aromatic hydroxy compounds composed of 2 to 9 amino acids, and / or at least one CH-active
  • the 5-arylpenta-2,4-dienylcarbonyl compounds of the formula I and the compounds of component B can either be applied to the hair simultaneously or in succession, it being irrelevant which of the two components is applied first.
  • the optionally contained ammonium or metal salts can be added to the first or the second component. Between application the first and second components can be up to 30 minutes apart. Pretreatment of the fibers with the saline solution is also possible.
  • the 5-arylpenta-2,4-dienylcarbonyl compounds of the formula I and the compounds of component B 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 millimoles of a 5-arylpenta-2,4-dienylcarbonyl compound of Formula I, 10 millimoles of an oxidation dye precursor, 10 millimoles of sodium acetate, and a drop of a 20 percent fatty alkyl ether sulfate solution in 100 milliliters of water were 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 tress was then rinsed with lukewarm water for 30 seconds, dried with warm air and then combed out.
  • the color depth was rated on the following scale:
  • Component B pH value Color shade Color depth

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  • Cosmetics (AREA)

Abstract

L'invention concerne un produit permettant de colorer des fibres contenant de la kératine, notamment des cheveux humains. Ce produit contient des composés 5-arylpenta-2,4-diénylcarbonyle de la formule (I) où R1 représente un atome d'hydrogène ou un groupe alkyle C¿1?-C4; R?2 et R3¿ qui sont identiques ou différents, représentent un atome d'hydrogène, un atome d'halogène, un groupe alkyle C¿1?-C4, un groupe alcoxy C1-C4, un groupe hydroxy-C1-C4-alcoxy, un groupe hydroxy, un groupe nitro ou un groupe amino qui peut être substitué par un groupe alkyle C1-C4 ou faire partie intégrante d'un hétérocycle, ou un groupe alkyle C1-C4. Deux des restes peuvent former ensemble un noyau benzène fusionné. L'invention concerne également les sels physiologiquement compatibles de ces composés de la formule (I).
PCT/EP1999/006525 1998-09-15 1999-09-04 Produit de coloration de fibres contenant de la keratine WO2000015183A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU57454/99A AU5745499A (en) 1998-09-15 1999-09-04 Agents for dyeing fibres containing keratin
JP2000569768A JP2002524483A (ja) 1998-09-15 1999-09-04 ケラチン含有繊維用の染色製剤
EP99944605A EP1112055A1 (fr) 1998-09-15 1999-09-04 Produit de coloration de fibres contenant de la keratine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19842070.6 1998-09-15
DE1998142070 DE19842070A1 (de) 1998-09-15 1998-09-15 Mittel zum Färben von keratinhaltigen Fasern

Publications (1)

Publication Number Publication Date
WO2000015183A1 true WO2000015183A1 (fr) 2000-03-23

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/006525 WO2000015183A1 (fr) 1998-09-15 1999-09-04 Produit de coloration de fibres contenant de la keratine

Country Status (5)

Country Link
EP (1) EP1112055A1 (fr)
JP (1) JP2002524483A (fr)
AU (1) AU5745499A (fr)
DE (1) DE19842070A1 (fr)
WO (1) WO2000015183A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001034106A1 (fr) * 1999-10-23 2001-05-17 Henkel Kommanditgesellschaft Auf Aktien Agent pour colorer des fibres a base de keratine

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE60331512D1 (de) 2002-09-13 2010-04-15 Kao Corp Haarfärbezusammensetzung enthaltend Methinfarbstoff

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1576453A (fr) * 1967-04-19 1969-08-01
GB1263075A (en) * 1968-04-17 1972-02-09 Ici Ltd New dyestuffs
WO1996022077A1 (fr) * 1995-01-18 1996-07-25 Henkel Kommanditgesellschaft Auf Aktien Arylcetones pour colorer des fibres contenant de la keratine
JPH10265340A (ja) * 1997-03-26 1998-10-06 Shiseido Co Ltd メチレンジオキシベンゼン環−脂肪族化合物含有頭部用組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1576453A (fr) * 1967-04-19 1969-08-01
GB1263075A (en) * 1968-04-17 1972-02-09 Ici Ltd New dyestuffs
WO1996022077A1 (fr) * 1995-01-18 1996-07-25 Henkel Kommanditgesellschaft Auf Aktien Arylcetones pour colorer des fibres contenant de la keratine
JPH10265340A (ja) * 1997-03-26 1998-10-06 Shiseido Co Ltd メチレンジオキシベンゼン環−脂肪族化合物含有頭部用組成物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 199850, Derwent World Patents Index; AN 1998-589626, XP002125793, "Composition for cephalic application - contains methylenedioxybenzene ring-aliphatic compound(s) and prevents depilation" *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001034106A1 (fr) * 1999-10-23 2001-05-17 Henkel Kommanditgesellschaft Auf Aktien Agent pour colorer des fibres a base de keratine
EP1235549A1 (fr) * 1999-10-23 2002-09-04 Henkel Kommanditgesellschaft auf Aktien Agent pour colorer des fibres a base de keratine
US6790239B1 (en) 1999-10-23 2004-09-14 Henkel Kommanditgesellschaft Auf Aktien Agent for coloring keratin containing fibers

Also Published As

Publication number Publication date
JP2002524483A (ja) 2002-08-06
EP1112055A1 (fr) 2001-07-04
AU5745499A (en) 2000-04-03
DE19842070A1 (de) 2000-03-16

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