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WO2000038632A1 - Procede permettant de colorer les fibres de keratine au moyen de derives de l'acide 2-oxocarboxylique associes a des nucleophiles - Google Patents

Procede permettant de colorer les fibres de keratine au moyen de derives de l'acide 2-oxocarboxylique associes a des nucleophiles Download PDF

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Publication number
WO2000038632A1
WO2000038632A1 PCT/EP1999/009907 EP9909907W WO0038632A1 WO 2000038632 A1 WO2000038632 A1 WO 2000038632A1 EP 9909907 W EP9909907 W EP 9909907W WO 0038632 A1 WO0038632 A1 WO 0038632A1
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Prior art keywords
amino
acid
group
hydroxy
methyl
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PCT/EP1999/009907
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German (de)
English (en)
Inventor
Hinrich Möller
Horst Höffkes
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Henkel Kommanditgesellschaft Auf Aktien
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Priority to AU16587/00A priority Critical patent/AU1658700A/en
Publication of WO2000038632A1 publication Critical patent/WO2000038632A1/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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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

Definitions

  • the invention relates to a process for dyeing fibers containing keratin, in particular human hair, in which 2-oxocarboxylic acid derivatives are used in combination with nucleophiles or the reaction product thereof as a coloring component.
  • 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.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components.
  • Suitable coupling substances are, in particular, ⁇ -naphthol, 1, 5-, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl 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, 2nd -Chlor-6-methyl-3-aminophenol, 2-methylresorcinol and 5-methylresorcinol.
  • oxidation dyes intensive dyeings can be achieved with good fastness properties, but the development of the color is usually done under the influence of oxidizing agents such. B. H 2 0 2 , which in some cases can result in damage to the fiber. Furthermore, some oxidation dye precursors or certain mixtures of oxidation dye precursors can sometimes be found in people with sensitive skin act sensitizing. 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 to the usual oxidation hair colorants in terms of color depth, gray coverage and fastness properties, but without necessarily relying on oxidizing agents such as e.g. B. H 2 O 2 to be instructed.
  • the colorants may have no or only a very low sensitization potential.
  • the present invention accordingly relates to a process for dyeing fibers containing keratin, in particular human hair, in which (A) 2-oxocarboxylic acid derivatives having the formula (I)
  • R represents a hydrogen atom, a C r C 4 alkyl group, a carboxyl radical, a carboxylate radical, an aryl, benzyl or heteroaryl group, which can be substituted by one or more C r C 4 alkyl, C r C 4 alkoxy, C r C 4 hydroxyalkoxy, hydroxy, carboxy, sulfo or nitro group (s), X for O " , OH, a C r C 4 alkoxy or an NR 2 R 3 group in which R 2 and R 3 are the same or different and hydrogen, C r C 4 alkyl or hydroxy-C 2 -C 4 -alkyl, where, when X is NR 2 R 3 , the radicals R 2 and R 3 can also form a heterocyclic ring together with the nitrogen atom, in combination with
  • a primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, from 2 to 9 amino acids and oligopeptides and aromatic hydroxy compounds, and / or at least one CH-active compound, or the reaction product from components A and B are applied to the fiber as a coloring component.
  • Another object of the present invention is an agent for dyeing keratin fibers, in particular human hair, which contains as a coloring component
  • Keratin-containing fibers are wool, furs, feathers and in particular human hair.
  • the colorants according to the invention can also be used for dyeing other natural fibers, such as, for. As cotton, jute, sisal, linen or silk, modified natural fibers, such as. B. regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose and synthetic fibers such as.
  • B. polyamide, polyacrylonitrile, -, polyurethane and polyester fibers can be used.
  • the 2-oxocarboxylic acid derivatives of the formula I used according to the invention are preferably selected from the group consisting of pyruvic acid, glyoxylic acid, mesoxalic acid, phenylglyoxylic acid, 2-
  • the above-mentioned 2-oxocarboxylic acid derivatives with the formula I are preferably used in the process 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.
  • the 2-oxocarboxylic acid derivatives with the formula I are used as the only colorant in the process according to the invention, colorations in the brown range are obtained. Colorings with further increased brilliance and improved fastness properties (light fastness, wash fastness, rub fastness), especially in the yellow, orange, brown and black range, are achieved if the Compounds with the formula I are used together with the compounds referred to as component B. On the one hand, these are compounds which, on their own, only weakly dye keratin-containing fibers and only give brilliant colors together with the 2-oxocarboxylic acid derivatives of the formula I. On the other hand, there are also compounds that are already used as oxidation dye precursors.
  • the 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.
  • Suitable compounds with primary or secondary amino group as component B are e.g. B. primary aromatic amines such as N, N-dimethyl, N, N-diethyl, N- (2-hydroxyethyl) -N-ethyl, N, N-bis (2-hydroxyethyl) -, N- (2nd -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-diaminophen
  • R 4 represents a hydroxy or an amino group which may be substituted by C 1-4 alkyl, C 1-4 hydroxyalkyl, C 1-4 alkoxy or C 1-4 alkoxy-C 1-4 alkyl groups,
  • R 5 , R 6 , R 7 , R 8 and R 9 represent hydrogen, a hydroxy or an amino group
  • C 1 . 4 -Alkyl-, C ⁇ -hydroxyalkyl, C ⁇ -alkoxy-, C M -aminoalkyl- or C ⁇ -alkoxy-C ⁇ - alkyl groups can be substituted, and
  • Y for a direct bond, a saturated or unsaturated carbon chain with 1 to 4 carbon atoms, optionally substituted by hydroxyl groups, a Car- bonyl, sulfonyl or imino group, an oxygen or sulfur atom, or a group with the formula III
  • an NR 10 group in which R 10 is hydrogen, a C 1-4 alkyl or a hydroxy-C 1-4 alkyl group, the group 0- (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 and its hydrochloride, 4,4'- Diamino-stilbene-2,2'-disulfonic acid mono- or di-Na salt, 4-amino-4'-dimethylaminostilbene, 4-amino-4'-dimethylaminostilbene dihydrochloride, 4,4'-diaminodiphenylmethane, -sulfide, -sulfoxide, -amine, 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenz
  • 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 e.g. B. 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-a
  • Suitable aromatic hydroxy compounds are e.g. B. 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 -Chlorresorcin, 1-naphthol, 1, 5-, 1, 6-, 1, 7-, 2,3-, 2,6-, 2,7-dihydroxynaphthalene, 2-naphthol-3,6-disulfonic acid Na- Salt, 6-dimethylamino-4-hydroxy-2-n
  • the oligopeptides can be naturally occurring or synthetic oligopeptides, but also the oligopeptides contained in polypeptide or protein hydrolyzates, provided they have sufficient water solubility for use in the colorants according to the invention.
  • the oligopeptides contained in polypeptide or protein hydrolyzates are e.g. As glutathione or the oligopeptides contained in the hydrolyzates of collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein.
  • Use together with compounds having a primary or secondary amino group or with aromatic hydroxy compounds is preferred.
  • 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-tetramethyl-3H-indolium methanesulfonate, Fischer's base (1,3,3-trimethyl-2-methyleneindoline) (as a salt of a strong acid), 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, diethylthiobiouric acid 3-
  • the compounds of component B are particularly preferably selected from the group consisting of N- (2-hydroxyethyl) -N-ethyl-, 2-chloro-p-phenylene-diamine, 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-amino, 2-hydroxymethyl-4-amino, 2-amino-4- (2-hydroxyethylamino) -, 3,4
  • Oxidizing agents e.g. B. H 2 0 2
  • Oxidizing agents are usually 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 .
  • customary direct dyes e.g. B. from the group of nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred direct dyes are those with the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, HC Blue 12, 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 4-amino-2-nitrodipheny-lamin- 2'-carboxylic acid, 6-nitro-1, 2,3,4-tetrahydroquinoxaline, hydroxyethyl-2-nitro-toluidine, picramic acid, 2-amino-6-chloro-4-nitrophenol, 4-ethylamino-3-nitrobenzoic acid and 2-chloro-6-ethylamino-1-hydroxy-4-nitrobenzene.
  • 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
  • preparations 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, rotten bark, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, rotten bark, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • oxidation dye precursors or the optional direct dyes each represent uniform compounds. Rather, in the present invention, due to the manufacturing process for the individual dyes, additional components can be used in minor amounts, provided that these are not Adversely affect the coloring result or for other reasons, e.g. B. toxicological, must be excluded.
  • the agent according to the invention produces intensive colorations even at physiologically tolerable temperatures of below 45 ° C. It is therefore particularly suitable for dyeing human hair.
  • the individual components are usually worked into a water-containing cosmetic carrier.
  • Suitable water-containing cosmetic carriers are e.g. B. creams, emulsions, gels or surfactant-containing foaming solutions such.
  • B. shampoos or other preparations that are suitable for use on the keratin fibers. If necessary, it is also possible to incorporate the components into anhydrous carriers.
  • 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.
  • 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, linear fatty acids with 10 to 22 carbon 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 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, sulfosuccinic acid and dialkyl esters with 8 to 18 C atoms in the alkyl group and sulfosuccinic acid mono-alkyl polyoxyethyl ester with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkanesulfonates with 12 to 18 carbon atoms, linear alpha-olefin sulfonates with 12 to 18 carbon atoms, methyl al
  • 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 -S0 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 cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine.
  • Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a C 8 . 18 -alkyl or -acyl group in the molecule contain at least one free amino group and at least one -COOH or -S0 3 H group and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylamino-butyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylamino acetic acids each about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-coconut alkyl aminopropionate, coconut acylaminoethyl aminopropionate 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 processes 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 polydimethylsiloxane, Quaternium-80).
  • alkylamidoamines especially fatty acid amidoamines such as the stearylamidopropyldimethylamine available under the name Tego Amid ® S 18, are notable for their good biodegradability. Also very good biodegradability are quaternary Estertellen, so-called “esterquats”, such as those sold under the trademark Stepantex ® methylhydroxyalkyldialkoyloxyalkylammonium.
  • a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to 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.
  • 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 homologues which are obtained as catalysts when fatty alcohol and alkylene oxide are reacted 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.
  • non-ionic polymers such as vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone ⁇ / inylacetate copolymers and polysiloxanes
  • cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers, dimethyldiallyl amide sulfonated polymers, acrylated amidyl amide sulfonated polymers, acrylated amidoxysulfonated polymers, acrylated amidoxylated copolymers, Dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers,
  • Vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as, for example, acrylamidopropyl trimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate / tert.-butylaminoethyl methacrylate / 2-hydroxypropyl acrylate polymers, for example polyacrylate, 2-hydroxypropyl acrylate polymers, crosslinked polyacrylic acids, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / inyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / N-tert.-butyl acrylamides
  • Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. As methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as. B. bentonite or fully synthetic hydrocolloids such.
  • 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,
  • Complexing agents such as EDTA, NTA and phosphonic acids, 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 0, dimethyl ether, CO 2 and air, and antioxidants.
  • constituents of the water-containing carrier are used for the production of the agents used in the process according to the invention in amounts customary for this purpose, e.g.
  • 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. B. 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, whereby sodium acetate, lithium bromide, calcium bromide , Calcium gluconate, zinc chloride, zinc sulfate, magnesium chloride, magnesium sulfate, ammonium carbonate, chloride and acetate are 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 used.
  • the pH of the ready-to-use coloring preparations is usually between 2 and 11, preferably between 5 and 9.
  • the components and customary cosmetic ingredients are usually applied to the fibers containing keratin, left on the fiber for some time, usually about 30 minutes, and then rinsed out or washed out with a shampoo.
  • the 2-oxocarboxylic acid derivatives of the formula I and the compounds of component B are applied to the hair in one process step, ie. H. the components are applied together or in succession, but without pretreatment of the fiber by one of the components.
  • the optionally contained ammonium or metal salts can be added to the first or the second component. Pretreatment of the fibers with the saline solution is not excluded.
  • the 2-oxocarboxylic acid derivatives of the formula I and the compounds of component B are preferably stored separately, 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 only intimately mixed with one another immediately before use. In dry storage, a defined amount of warm (30 to 80 ° C) water is usually added before use and a homogeneous mixture is produced.
  • a slurry of 10 mmol of a 2-oxocarboxylic acid derivative of the formula I, if appropriate 10 mmol of an oxidation dye precursor, 10 mmol of sodium acetate and a drop of a 20% strength fatty alkyl ether sulfate solution in 100 ml of water was prepared.
  • the slurry was heated to about 30 ° C and the pH was 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:

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  • Cosmetics (AREA)

Abstract

L'invention concerne un procédé permettant de colorer les fibres de kératine, notamment les cheveux, au moyen d'agents colorants pouvant être appliqués sur les cheveux. Lesdits agents colorants comprennent: A) des dérivés de l'acide 2-oxocarboxylique de formule (I), dans laquelle R1 représente un atome d'hydrogène, un groupe alkyle C¿1?-C4, un résidu carboxyle, un résidu carboxylate ou bien un groupe aryle, benzyle ou hétéroaryle, pouvant être substitué par un ou plusieurs groupes alkyle C1-C4, alcoxy C1-C4, hydroxyalcoxy C1-C4, hydroxy, carboxy, sulfo ou nitro; X représente O?-¿, OH, un groupe alcoxy C¿1?-C4 ou NR?2R3, où R2 et R3¿, identiques ou différents, représentent hydrogène, alkyle C¿1?-C4 ou hydroxyalkyle C2-C4, à condition que quand X représente NR?2R3, R2 et R3¿ puissent, avec l'atome d'azote, former un noyau hétérocyclique; lesdits dérivés étant associés à B) au moins un composé renfermant un groupe amino ou hydroxy primaire ou secondaire, choisi parmi les amines aliphatiques ou aromatiques primaires ou secondaires, les composés hétérocycliques azotés, les oligopeptides constitués de 2 à 9 acide aminés et les composés hydroxy aromatiques et/ou au moins un composé à CH actif.
PCT/EP1999/009907 1998-12-23 1999-12-14 Procede permettant de colorer les fibres de keratine au moyen de derives de l'acide 2-oxocarboxylique associes a des nucleophiles WO2000038632A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU16587/00A AU1658700A (en) 1998-12-23 1999-12-14 Method for dying keratin fibers using 2-oxocarboxylic acid derivatives in conjunction with nucleophiles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1998159722 DE19859722A1 (de) 1998-12-23 1998-12-23 Verfahren zum Färben von keratinhaltigen Fasern unter Verwendung von 2-Oxocarbonsäurederivaten in Kombination mit Nucleophilen
DE19859722.3 1998-12-23

Publications (1)

Publication Number Publication Date
WO2000038632A1 true WO2000038632A1 (fr) 2000-07-06

Family

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PCT/EP1999/009907 WO2000038632A1 (fr) 1998-12-23 1999-12-14 Procede permettant de colorer les fibres de keratine au moyen de derives de l'acide 2-oxocarboxylique associes a des nucleophiles

Country Status (3)

Country Link
AU (1) AU1658700A (fr)
DE (1) DE19859722A1 (fr)
WO (1) WO2000038632A1 (fr)

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FR2986794A1 (fr) * 2012-02-09 2013-08-16 Oreal Composition cosmetique comprenant un compose apte a liberer un motif hc(o)-c(o)-, compose et procede de traitement cosmetique
JP2016518397A (ja) * 2013-05-10 2016-06-23 花王株式会社 毛髪を一段階でカラーリング及び直毛化するためのプロセス

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DE10343236A1 (de) * 2003-09-17 2005-04-14 Henkel Kgaa Mittel zur Verminderung der Kopfhautanfärbung
FR2986704B1 (fr) 2012-02-09 2015-08-21 Oreal Procede de traitement cosmetique et composition comprenant un ester d'acide glyoxylique
WO2013117771A2 (fr) 2012-02-09 2013-08-15 L'oreal Procédé de traitement cosmétique et composition comprenant un dérivé d'acide glyoxylique
FR2986706B1 (fr) * 2012-02-09 2015-09-18 Oreal Composition comprenant un (thio)acetal ou un hemi(thio)acetal d'acide glyoxylique et procede de traitement cosmetique
FR2986791B1 (fr) * 2012-02-09 2014-02-21 Oreal Composition comprenant un derive d'acide glyoxylique et procede de traitement cosmetique
FR2997848B1 (fr) 2012-11-09 2015-01-16 Oreal Composition comprenant un derive dicarbonyle et procede de lissage des cheveux a partir de cette composition
FR2997846B1 (fr) 2012-11-09 2023-10-20 Oreal Composition comprenant un derive dicarbonyle et un acide, le procede de lissage des fibres keratiniques a partir de cette composition
FR2997851B1 (fr) 2012-11-09 2014-11-28 Oreal Composition comprenant un derive dicarbonyle et procede de lissage des cheveux a partir de cette composition
FR2997849B1 (fr) 2012-11-09 2015-01-16 Oreal Composition comprenant un derive dicarbonyle et procede de lissage des cheveux a partir de cette composition
FR2997850B1 (fr) 2012-11-09 2015-10-23 Oreal Composition comprenant un derive dicarbonyle et procede de lissage des cheveux a partir de cette composition
FR2997847B1 (fr) 2012-11-09 2015-06-19 Oreal Composition comprenant de l'acide glyoxylique et une silicone aminee, procede de lissage des cheveux a partir de cette composition
FR2997844B1 (fr) 2012-11-09 2014-12-05 Oreal Composition comprenant un compose dicarbonyle et procede de lissage des cheveux a partir de cette composition
EP2883535A1 (fr) 2013-12-13 2015-06-17 Alfa Parf Group S.p.a. Compositions et procédés simultanés de coloration directe et de reformage des cheveux
US11179312B2 (en) 2017-06-05 2021-11-23 Momentive Performance Materials Inc. Aqueous compositions for the treatment of hair
US11090255B2 (en) 2018-12-04 2021-08-17 Momentive Performance Materials Inc. Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair

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JPS548731A (en) * 1977-06-18 1979-01-23 Sunstar Inc Hair dyeing agent
DE4216667A1 (de) * 1992-05-20 1993-11-25 Wella Ag Haarbehandlungsmittel
DE4417546A1 (de) * 1994-05-19 1995-11-23 Henkel Kgaa 2-Oxoessigsäurederivate zum Färben keratinhaltiger Fasern

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JPS548731A (en) * 1977-06-18 1979-01-23 Sunstar Inc Hair dyeing agent
DE4216667A1 (de) * 1992-05-20 1993-11-25 Wella Ag Haarbehandlungsmittel
DE4417546A1 (de) * 1994-05-19 1995-11-23 Henkel Kgaa 2-Oxoessigsäurederivate zum Färben keratinhaltiger Fasern

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DATABASE WPI Week 197909, Derwent World Patents Index; AN 1979-16902B, XP002133268 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2986794A1 (fr) * 2012-02-09 2013-08-16 Oreal Composition cosmetique comprenant un compose apte a liberer un motif hc(o)-c(o)-, compose et procede de traitement cosmetique
JP2016518397A (ja) * 2013-05-10 2016-06-23 花王株式会社 毛髪を一段階でカラーリング及び直毛化するためのプロセス
US10874185B2 (en) 2013-05-10 2020-12-29 Kao Corporation Process for one-step colouring and straightening hair

Also Published As

Publication number Publication date
AU1658700A (en) 2000-07-31
DE19859722A1 (de) 2000-06-29

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