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WO2000038636A1 - Agent permettant de colorer les fibres de keratine - Google Patents

Agent permettant de colorer les fibres de keratine Download PDF

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Publication number
WO2000038636A1
WO2000038636A1 PCT/EP1999/009998 EP9909998W WO0038636A1 WO 2000038636 A1 WO2000038636 A1 WO 2000038636A1 EP 9909998 W EP9909998 W EP 9909998W WO 0038636 A1 WO0038636 A1 WO 0038636A1
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WIPO (PCT)
Prior art keywords
amino
group
acid
hydroxy
alkyl group
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PCT/EP1999/009998
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German (de)
English (en)
Inventor
Hinrich Möller
Doris Oberkobusch
Horst Höffkes
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Priority to AU19806/00A priority Critical patent/AU1980600A/en
Publication of WO2000038636A1 publication Critical patent/WO2000038636A1/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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • 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
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the invention relates to an agent for dyeing keratin-containing fibers, in particular human hair, which contains nitroisatine in combination with oxidation dye precursors, the use of this combination as a coloring system in hair dye compositions and a process for dyeing keratin-containing fibers, in particular 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-aminopyrazoIone 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, m-aminophenols and substituted pyridine derivatives are generally used as coupler components.
  • coupler substances are ⁇ -naphthol, 1, 5-, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4-diaminophenoxyethanol , 2-Amino-4- (2-hydroxyethylamino) anisole (Lehmanns Blau), 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, 5-methylresorcinol, 3-amino-6-methoxy-2-methylamino-pyridine and 3,5-diamino-2,6-dimethoxypyridine.
  • European patent applications 502 783 and 502 784 describe processes for dyeing keratin-containing fibers, in which a combination of isatin and pyridine derivatives or aniline derivatives are used as coloring components.
  • 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 0 2 to be instructed.
  • the colorants may have no or only a very low sensitization potential.
  • a combination of the nitroisatins and oxidation dye precursors shown in the formula I is particularly suitable for dyeing keratin-containing fibers, even in the absence of oxidizing agents. They result in colors with excellent brilliance and depth of color and lead to a wide range of shades.
  • the use of oxidizing agents should not be excluded in principle. It was also found that the colorations are significantly more intense compared to the unsubstituted isatin.
  • the invention relates to an agent for dyeing keratin-containing fibers, in particular human hair, comprising A) nitroisatine with the formula I,
  • R 1 is hydrogen, a CC 4 -alkyl group, C 1 -C 4 -alkenyl group, CC 4 -alkoxy group, hydroxy-C C 4 -alkyl group, amino-C C 4 -alkyl group, which can be substituted on nitrogen, a optionally substituted AryI-C C 4 alkyl group
  • R 2 and R 3 represent hydrogen, halogen, CrC ⁇ alkyl group, C r C 4 alkenyl group, CC 4 alkoxy group, hydroxy-C 1 -C 4 alkyl group, a hydroxyl, carboxy, sulfo, nitro or amino group, which can be substituted by one or two C 1 -C 4 alkyl group (s), or a C.-O, - acyl group, with two of the radicals can together form a fused aromatic ring
  • 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, 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 compounds having the formula I are preferably selected from the group of the following nitroisatins: 5-nitroisatin, 1-methyl-5-nitroisatin, 1-benzyl-5-nitroisatin, 1- (4-chlorobenzyl) -5-nitroisatin, 7-chlorine -5-nitroisatin, 5-chloro-7-nitroisatin, 5-bromo-5-nitroisatin, 5-methoxy-7-nitroisatin, 5,7-dinitroisatin, 6-nitroisatin and any mixtures thereof.
  • nitroisatins 5-nitroisatin, 1-methyl-5-nitroisatin, 1-benzyl-5-nitroisatin, 1- (4-chlorobenzyl) -5-nitroisatin, 7-chlorine -5-nitroisatin, 5-chloro-7-nitroisatin, 5-bromo-5-nitroisatin, 5-methoxy-7-nitroisatin, 5,7-dinitroisatin, 6-nitroisatin and any mixtures thereof.
  • the compounds of component B are, on the one hand, compounds which, on their own, only weakly dye keratin-containing fibers and only give brilliant colorations together with the nitroisatins of the formula I. On the other hand, there are also compounds that are already used as oxidation dye precursors.
  • nitroisatins of the formula I can also be used together in all colorants; Likewise, several different compounds of component B can also be used together.
  • the subject of the present invention also includes the use of such substances which are reaction products of nitroisatins of the formula I with the compounds of component B mentioned as direct colorants.
  • 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 -Methoxye- ethyl-), 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-diamin
  • R 4 represents a hydroxyl or an amino group which may be substituted by C 1-4 alkyl, C 1-4 hydroxy alkyl, C 1-4 alkoxy or C 1-4 alkoxy-C 1-4 alkyl groups ,
  • R 4 , R 6 , R 7 , R 8 and R 9 represent hydrogen, a hydroxy or an amino group
  • Y is a direct bond, a CH 2 or CHOH group
  • an NR 10 group wherein R 10 is hydrogen, a C 1-4 alkyl or a hydroxy-C ,.
  • 4 - alkyl group means 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 for example 4,4'-diaminostilbene and its hydrochloride, 4,4'-diamino-stilbene-2,2'-disulfonic acid mono- or di-Na salt, 4-amino-4'-dimethylaminostilbene and its hydrochloride, 4 , 4'-diaminodiphenylmethane, - sulfide, -sulfoxide, -amine, 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone
  • 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-amino
  • 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-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-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-methyl-2-quinaldinium iodide, 1-ethyl-2-quinaldinium iodide, 1, 4-dimethylquinolinium iodide, barbituric acid, thiobarbituric acid, 1, 3-dimethylthiobarbituric acid, 1, 3-diethylthi
  • Preferred amino acids are all naturally occurring and synthetic ⁇ -amino acids, e.g. B. by hydrolysis of vegetable or animal proteins, e.g. B. collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein, accessible amino acids. Both acidic and alkaline amino acids can be be set. Preferred amino acids are arginine, histidine, tyrosine, phenylalanine, DOPA (dihydroxyphenylalanine), ornithine, lysine and tryptophan. But also other amino acids, such as. B. 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 are e.g. B. 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, 2-amino-4- (2-hydroxyethylamino) anisole, 2- (2.4-
  • Diaminophenoxy) ethanol 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 -Diamino benzoic acid, 2,5-diamino-, 2-dimethylamino-5-amino-, 3-amino-2-methylamino-6-methoxy-, 2,3-diamino-6-methoxy-, 3,5 -Diamino-2,6-dimethoxy-, 2,6-dihydroxy-3,4-dimethylpyridine, 2-hydroxy-4,5,6-triamino-, 4-hydroxy-2,5,6-triamino-, 2, 4,5,6-tetraamino, 2-methyla
  • Oxidizing agents e.g. B. H 2 O 2l can be omitted. However, it can It may be desirable to add hydrogen peroxide or other oxidizing agents to the agents according to the invention to achieve the shades which are lighter than the keratin-containing fiber to be colored. 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, for further modification of the color shades.
  • customary direct dyes for example, for further modification of the color shades.
  • B. from the group of nitrophenylenediamines, nitroaminophenols, anthraquinones or indophenols, such as. B.
  • HC Yellow 2 under the international names or trade names HC Yellow 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-nitrodiphe - nylamine-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 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.
  • the oxidation dye precursors or the optional direct dyes each represent uniform compounds.
  • further components may be present in minor amounts, provided that these do not adversely affect the coloring result or for other reasons, e.g. B. 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. B. creams, emulsions, gels or surfactant-containing foaming solutions such.
  • 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.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • 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 R-0- (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, 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 alpha
  • 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 also the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide
  • 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.
  • 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, Quatemium-80).
  • Q2-7224 commercially available products
  • Dow Corning a stabilized trimethylsilylamodimethicone
  • Dow Corning 929 emulsion containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone
  • SM-2059 manufactured by General Electric
  • SLM-55067 Manufacturer
  • alkylamidoamines especially fatty acid amidoamines such as the stearylamidopropyldimethylamine available under the name Tego Amid ® S 18, are notable for their good biodegradability.
  • 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.
  • nonionic polymers such as, for example, vinylpyrrolidone ⁇ / inylacrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone ⁇ / inylacetate copolymers and polysiloxanes
  • cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallyl polymers, dimethyldiallyl -Dimethyldiallylammonium chloride copolymers, dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers quaternized with diethyl sulfate,
  • 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, cross-linked polyacrylic acids, 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 terpoly
  • 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 O, dimethyl ether, CO 2 and air, and antioxidants.
  • the constituents of the water-containing carrier are used to produce the colorants according to the invention in amounts customary for this purpose; z. B. are emulsifiers in concentrations of 0.5 to 30 wt .-% and Thickeners are used 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, 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 A) one or more nitroisatins of the formula I,
  • R 1 for hydrogen, a C r C 4 alkyl group, C 1 -C 4 alkenyl group, C ⁇ -C ⁇ alkoxy group, hydroxy-C C 4 alkyl group, amino-C., - C 4 - alkyl group, the can be substituted on the nitrogen, an optionally substituted aryl-C 1 -C 4 -alkyl group, R 2 and R 3 are hydrogen, halogen, C r C 4 alkyl group, C r C 4
  • Yet another object of the present invention relates to a process for dyeing fibers containing keratin, in particular human hair, in which a colorant comprising A) at least one nitroisatin of the formula I,
  • R 1 for hydrogen, a CC 4 -alkyl group, C r C 4 -alkenyl group, CC 4 -alkoxy group, hydroxy-C C 4 -alkyl group, amino-C, - ⁇ - alkyl group, which may be substituted on the nitrogen, a optionally substituted aryl-C r C 4 -alkyl group, R 2 and R 3 for hydrogen, halogen, CC 4 alkyl group, CC 4 alkenyl group, C r C 4 alkoxy group, hydroxy-C C 4 alkyl group, a hydroxy, carboxy, sulfo, nitro or Amino group, which can be substituted by one or two C 1 -C 4 alkyl group (s), or a CC 4 - acyl group, where two of the radicals together can form a fused aromatic ring, and B) at least one compound selected from Compounds with primary or secondary amino group or hydroxy group, selected from primary or secondary ali
  • the nitroisatins of the formula I and the compounds of component B can either be applied to the hair simultaneously or else 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. 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.
  • nitroisatins of 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 largely reduce the reaction of the components be anhydrous. When stored separately, the reactive components are 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 5 mmol of nitroisatin with the formula I, 5 mmol of an oxidation dye precursor of component B and 5 mmol of sodium acetate and a drop of a 20% fatty alkyl ether sulfate solution in 50 ml of water at 60 ° C. were prepared.
  • the slurries were mixed together at 30 ° C. and adjusted to a pH of 6 using dilute sodium hydroxide solution or hydrochloric acid.
  • 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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Abstract

L'invention concerne un agent permettant de colorer les fibres de kératine, notamment les cheveux, qui contient: A) une nitro-isatine de formule (I), dans laquelle R1 représente hydrogène, alkyle C¿1?-C4, alcényle C1-C4, alcoxy C1-C4, hydroxyalkyle C1-C4, amino-alkyle C1-C4 pouvant être substitué au niveau de l'azote ou aryle C1-C4 éventuellement substitué; R?2 et R3¿ représentent hydrogène, halogène, alkyle C¿1?-C14, alcényle C1-C4, alcoxy C1-C4, hydroxyalkyle C1-C4, hydroxy, carboxy, sulfo, nitro, amino pouvant être substitué par un ou deux groupes alkyle C1-C4 ou acyle C1-C4, deux desdits résidus pouvant former ensemble un noyau aromatique condensé; et B) au moins un composé choisi parmi les composés comportant un groupe amino ou hydroxy primaire ou secondaire, choisi parmi les amines aliphatiques ou aromatiques primaires ou secondaires, les composés hétérocycliques azotés, les acides aminés, les oligopeptides constitués de 2 à 9 acides aminés et les composés hydroxy aromatiques et/ou les composés à CH actif.
PCT/EP1999/009998 1998-12-23 1999-12-16 Agent permettant de colorer les fibres de keratine WO2000038636A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU19806/00A AU1980600A (en) 1998-12-23 1999-12-16 Agent for dying keratin fibers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19859723.1 1998-12-23
DE1998159723 DE19859723A1 (de) 1998-12-23 1998-12-23 Mittel zum Färben von keratinhaltigen Fasern

Publications (1)

Publication Number Publication Date
WO2000038636A1 true WO2000038636A1 (fr) 2000-07-06

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PCT/EP1999/009998 WO2000038636A1 (fr) 1998-12-23 1999-12-16 Agent permettant de colorer les fibres de keratine

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Country Link
AU (1) AU1980600A (fr)
DE (1) DE19859723A1 (fr)
WO (1) WO2000038636A1 (fr)

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US7964343B2 (en) 2003-05-13 2011-06-21 Ibis Biosciences, Inc. Method for rapid purification of nucleic acids for subsequent analysis by mass spectrometry by solution capture
US8017358B2 (en) 2001-03-02 2011-09-13 Ibis Biosciences, Inc. Method for rapid detection and identification of bioagents
US8026084B2 (en) 2005-07-21 2011-09-27 Ibis Biosciences, Inc. Methods for rapid identification and quantitation of nucleic acid variants
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
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DE19932567A1 (de) * 1999-07-13 2001-01-18 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern

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DE2716671A1 (de) * 1977-04-15 1978-10-19 Henkel Kgaa Haarfaerbemittel
EP0873745A2 (fr) * 1997-04-24 1998-10-28 Henkel Kommanditgesellschaft auf Aktien Agent de teinture de fibres kératiniques
DE19717282A1 (de) * 1997-04-24 1998-10-29 Henkel Kgaa Verwendung von 1-substituierten Isatinen zum Färben von keratinhaltigen Fasern

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DE2716671A1 (de) * 1977-04-15 1978-10-19 Henkel Kgaa Haarfaerbemittel
EP0873745A2 (fr) * 1997-04-24 1998-10-28 Henkel Kommanditgesellschaft auf Aktien Agent de teinture de fibres kératiniques
DE19717282A1 (de) * 1997-04-24 1998-10-29 Henkel Kgaa Verwendung von 1-substituierten Isatinen zum Färben von keratinhaltigen Fasern

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DE19859723A1 (de) 2000-06-29

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