[go: up one dir, main page]

WO1999020597A1 - Nouveaux derives d'aminophenol et leur utilisation pour colorer des fibres a base de keratine - Google Patents

Nouveaux derives d'aminophenol et leur utilisation pour colorer des fibres a base de keratine Download PDF

Info

Publication number
WO1999020597A1
WO1999020597A1 PCT/EP1998/006447 EP9806447W WO9920597A1 WO 1999020597 A1 WO1999020597 A1 WO 1999020597A1 EP 9806447 W EP9806447 W EP 9806447W WO 9920597 A1 WO9920597 A1 WO 9920597A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
aminophenol
alkyl group
aminophenol derivatives
oxidation
Prior art date
Application number
PCT/EP1998/006447
Other languages
German (de)
English (en)
Inventor
David Rose
Bernd Meinigke
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to AU11525/99A priority Critical patent/AU1152599A/en
Publication of WO1999020597A1 publication Critical patent/WO1999020597A1/fr

Links

Classifications

    • 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
    • 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
    • A61K8/415—Aminophenols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom

Definitions

  • the invention relates to new aminophenol derivatives, their use for dyeing keratin fibers and dyes containing these compounds.
  • oxidation colorants For dyeing keratin fibers, especially human hair, the so-called oxidation colorants play a preferred role because of their intense colors and good fastness properties.
  • colorants contain oxidation dye precursors, so-called developer components and coupler components.
  • developer components form the actual dyes under the influence of oxidizing agents or atmospheric oxygen with one another or under coupling with one or more coupler components.
  • Good oxidation dye precursors must first of all meet the following requirements: they must develop the desired color shades with sufficient intensity and authenticity in the oxidative coupling. They must also have a good ability to draw onto the fiber, whereby there must be no noticeable differences between stressed and freshly regrown hair, especially with human hair (leveling ability). They should be resistant to light, heat and the influence of chemical reducing agents, e.g. B. against perm fluids. After all, if they are used as a hair dye, they should not stain the scalp too much, and above all they should be harmless from a toxicological and dermatological point of view.
  • Preferred developer components are p-phenylenediamine, p-toluenediamine, p-aminophenol, 1 - ( ⁇ -hydroxyethyl) -2,5-diaminobenzene, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2- ( 2,5-diaminophenoxy) ethanol, 4,5-diamino-1 - (2-hydroxyethyl) pyrazole, l-phenyl-3-carboxyamido-4-amino-pyrazolone-5, 4-amino-3-methylphenol, 2 - On nomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 2-aminomethyl-4-aminophenol, 2,4,5,6-tetraaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy 2,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diammopyrr
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components.
  • 1-Naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinomino methyl ether, m-phenylenediamine, l-phenyl are particularly suitable as coupler substances -3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, l, 3-bis (2,4-diaminophenoxy) propane, 2-chloro-resorcinol, 4-chloro-resorcinol, 2-chloro -6-methy 1-3 -aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylresorcino
  • a first subject of the present invention are therefore aminophenol derivatives of the general formula (I)
  • R 1 and R 2 are (a) an alkyl group with 1 to 4 carbon atoms or (b) an alkoxy group with 1 to 4 carbon atoms, with the proviso that in each case exactly one substituent from the group (a ) and exactly one substituent from group (b) is represented and R 3 stands for
  • R 5 , R 6 , R 7 , R 8 , R 10 and R 11 are independently hydrogen, a C M alkyl group, a C hydroxy alkyl group and R 5 and R 6 , R 7 and R 8 as well as R 10 and R 11 each together with the nitrogen atom carrying them can also be part of a morpholino, piperidino or pyrrolidino radical and R 5 can also represent a group -SO 2 -CH 3 with the proviso that R 6 stands for hydrogen, and R 9 stands for hydrogen or a C M alkyl group, and their water-soluble salts.
  • R 1 is a substituent selected from group (a) and R 2 is a substituent selected from group (b).
  • Aminophenol derivatives of the formula (I) in which R 3 represents a C r to C 4 alkyl group, in particular hydrogen, are particularly preferred.
  • aminophenol derivatives according to formula (I) in which R 1 represents a methyl group and R 2 represents a methoxy group.
  • Particularly preferred compounds for the purposes of the present invention are 6-methoxy-2-methyl-3-aminophenol and 6-methoxy-2-methyl-3- ( ⁇ -hydroxyethylamino) phenol.
  • a second object of the present invention is the use of the aforementioned aminophenol derivatives as a coupler component in oxidation hair colorants.
  • a third object of the present invention are oxidation coloring agents for dyeing keratin fibers containing coupler components and developer components in a water-containing carrier, which contains one of the aforementioned aminophenol derivatives as the coupler component.
  • Keratin fibers in the sense of the present application are to be understood as furs, wool, feathers and in particular human hair.
  • the oxidation colorants according to the invention are primarily suitable for dyeing keratin fibers, there is in principle nothing to prevent their use in other areas, particularly in color photography.
  • the oxidation colorants according to the invention can contain one or more developer components and, if desired, further coupler components in addition to the coupler components according to the invention.
  • further developer and coupler components reference is made to the substances listed at the beginning of the description, which are preferred further dye components.
  • developer components are 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 1 - ( ⁇ -hydroxyethyl) -2,5-diaminobenzene, p-phenylenediamine, p-toluenediamine, p-aminophenol, 3-methyl-p-aminophenol, 2- Hydroxy-methyl-p-aminophenol and 2-aminomethyl-p-aminophenol.
  • 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinomino methyl ether, m-phenylenediamine, l-phenyl are particularly suitable as coupler components -3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, l, 3-bis (2,4-diaminophenoxy) propane, 2-chloro-resorcinol, 4-chloro-resorcinol, 2-chloro -6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylresorcinol o-aminophenol, 2,5-dimethylresorcinol, 2,6-dihydroxypyridine, 2,6-diaminopyridine, 2, 6-dihydroxy-3,4-dimethylpyridine, 2,6-
  • the hair colorants according to the invention preferably contain both the developer components and the coupler components in an amount of 0.005 to 20% by weight, preferably 0.1 to 5% by weight, in each case based on the total oxidation colorant.
  • Developer components and coupler components are generally used in approximately molar amounts to one another. If the molar use has also proven to be expedient, a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components can be present in a molar ratio of 1: 0.5 to 1: 2.
  • the hair colorants according to the invention contain, in addition to the oxidation dye precursors, customary direct dyes, for example from the group of nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols, such as, for example, under the international names or trade names HC, in addition to the oxidation dye precursors 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 4-amino-2-nitrodiphenylamine-2 '-carboxylic acid, 6-nitro-1 , 2,3, 4-tetrahydroquinoxaline, hydroxyethyl 1-2-nitro-toluidine, picramic acid, 2-amino-6-chloro-4-nitrophenol
  • 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 hair 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 oxidation dye precursors are incorporated into a suitable water-containing carrier.
  • suitable water-containing carrier are, for example, creams, emulsions, gels or also surfactant-containing foaming solutions, for example shampoos, aerosols or other preparations which are suitable for use on the hair.
  • 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,
  • Esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols with 8 to 22 carbon atoms.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one -COO - or -SO 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 coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the coconut acylaminopropyldimethyl ammonium 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 derivative known under the CTFA name
  • Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a C g . lg - alkyl or acyl group in the molecule contain at least one free amino group and at least one -COOH or -SO H group and
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylamino propionate and C -acylsarcosine.
  • Nonionic surfactants contain z as a hydrophilic group.
  • B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
  • Such connections are, for example
  • cationic surfactants which can be used in the hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds.
  • Ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B.
  • cetyltrimethylammonium chloride cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride, methyl l-alkylamidoemyl-2-alkylimidazolium -nium methosulfate and tricetylmethylammonium chloride.
  • the quaternized protein hydrolysates 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 Abü ® -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 ® are methyl hydroxyalkyldialkoyloxyalkyl-methosulfates.
  • An example of 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 are used as catalysts. The use of products with a narrow homolog distribution can be preferred.
  • Anionic, zwitterionic, amphoteric and non-ionic polymers such as, for example, vinyl acetate / crotonic acid copolymers, polydimethylsiloxanes, vinyl pyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic acid and anhydride polyesters, non-crosslinked polymers, non-copolymerized copolymers, non-copolymerized copolymers Acryl amidopropyl trimethylammonium chloride / acrylate copolymers, octylacrylamide / methyl memacrylate / tert-butyl.arninoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, Vinylpyrrolidone
  • Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, gelatin, pectins, 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 as e.g. Polyvinyl alcohol and polyacrylamide structurants such as maleic acid, mono-, di- and oligosaccharides, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, dyes for coloring the agent,
  • Anti-dandruff agents such as piroctone olamine, zinc omadine and climbazol, other substances for adjusting the pH, animal and vegetable protein hydrolysates, in particular elastin, collagen, keratin, milk protein, soy protein, almond protein and wheat protein hydrolysates, and their fatty acid condensation products and quaternized derivatives,
  • Vitamins and vitamin precursors such as panthenol, its derivatives and biotin, plant and honey extracts, such as in particular extracts from oak bark, nettle, witch hazel, hops, chamomile, burdock root, horsetail, linden flowers, almond, aloe vera, coconut, mango, apricot, lime, Wheat, Kiwi, melon, orange, grapefruit, sage, rosemary, birch, cuckoo flower, quendel, yarrow, hake, meristem, ginseng and ginger root, other active ingredients such as ceramides, allantoin, pyrrolidone carboxylic acids, and bisabolol, light stabilizers,
  • Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as walrus, beeswax, montan wax and paraffins, fatty acid alkanolamides,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates,
  • Opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers, pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate, complexing agents such as EDTA, NTA, ß-alanine diacetic acid and phosphonic acids, reducing agents and stabilizers such as e.g. Thioglycolic acid and its derivatives, thiolactic acid, cysteamine, thio malic acid and ⁇ -mercaptoethanesulfonic acid, as well as ascorbic acid, sulfites and dithionites,
  • pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate
  • complexing agents such as EDTA, NTA, ß-alanine diacetic acid and phosphonic acids
  • reducing agents and stabilizers such as e.g. Thioglycolic acid and its derivatives, thiolactic acid
  • Blowing agents such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 , N 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.
  • the oxidative development of the coloring can take place with atmospheric oxygen.
  • a chemical oxidizing agent is preferably used, especially when, in addition to the coloring, a lightening effect on human hair is desired.
  • Persulfates, chlorites and in particular hydrogen peroxide or their adducts with urea, melamine and potassium and sodium borate are suitable as oxidizing agents. It is also possible to carry out the oxidation with the aid of enzymes.
  • the enzymes can be used to transfer atmospheric oxygen to the developer component or to enhance the effect of small amounts of oxidizing agents present.
  • An example of an enzymatic process is the procedure to increase the effect of small amounts (eg 1% by weight and less, based on the total agent) of hydrogen peroxide by peroxidases.
  • the preparation of the oxidizing agent is expediently mixed with the preparation from the oxidation dye precursors immediately before hair coloring.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 10. It is particularly preferred to use the hair dye in a weakly alkaline environment.
  • the application temperatures can range between 15 and 40 ° C. After an exposure time of approx. 30 minutes, the hair dye is removed from the hair to be colored by rinsing. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. a coloring shampoo was used.
  • Cetylstearyl alcohol with approx. 20 mol EO (CTFA name: Ceteareth-20) (HENKEL)
  • Coupler component 7.5 mmol Na SO (inhibitor) 1.0
  • the ingredients were mixed together in order. After the oxidation dye precursors and the inhibitor had been added, the pH of the emulsion was first adjusted to 10 using concentrated ammonia solution, and the mixture was then made up to 100 g with water.
  • the oxidative development of the color was carried out using 3% by weight hydrogen peroxide solution as the oxidation solution.
  • 100 g of the emulsion were mixed with 50 g of hydrogen peroxide solution (3% by weight) and mixed.
  • the coloring cream was applied to approx. 5 cm long strands of standardized, 90% gray, but not specially pretreated human hair and left there at 32 ° C for 30 minutes. After the dyeing process was completed, the hair was rinsed, washed with a conventional shampoo and then dried.
  • the following coupler and developer components were used for the coloring:

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne de nouveaux dérivés d'aminophénol de la formule générale (I), dans laquelle R1 et R2 désignent (a) un groupe alkyle ayant entre 1 et 4 atomes de C ou (b) un groupe alcoxy ayant entre 1 et 4 atomes de C, sous réserve que dans chaque cas, il y ait précisément un substituant du groupe (a) et précisément un substituant du groupe (b) qui soient représentés et R3 désigne de préférence hydrogène ou un groupe alkyle C¿1?-C4. L'invention concerne également l'utilisation de ces dérivés pour colorer des fibres à base de kératine, ainsi que des colorants contenant lesdits composés.
PCT/EP1998/006447 1997-10-20 1998-10-12 Nouveaux derives d'aminophenol et leur utilisation pour colorer des fibres a base de keratine WO1999020597A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU11525/99A AU1152599A (en) 1997-10-20 1998-10-12 Novel aminophenol derivatives and the use thereof for dyeing keratin fibres

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1997146249 DE19746249A1 (de) 1997-10-20 1997-10-20 Neue Aminophenol-Derivate und deren Verwendung
DE19746249.9 1997-10-20

Publications (1)

Publication Number Publication Date
WO1999020597A1 true WO1999020597A1 (fr) 1999-04-29

Family

ID=7846027

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/006447 WO1999020597A1 (fr) 1997-10-20 1998-10-12 Nouveaux derives d'aminophenol et leur utilisation pour colorer des fibres a base de keratine

Country Status (3)

Country Link
AU (1) AU1152599A (fr)
DE (1) DE19746249A1 (fr)
WO (1) WO1999020597A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19927073A1 (de) * 1999-06-15 2000-12-21 Henkel Kgaa Neue Kupplerkomponenten für Oxidationshaarfarben

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4125601A (en) * 1976-04-21 1978-11-14 L'oreal Substituted nitroaminophenols, process for their preparation and dyeing compositions in which they are present
EP0410471A2 (fr) * 1989-07-28 1991-01-30 Kao Corporation 2-alkyl-4-methoxy-5-aminophénol ou sel de ce dernier, ou 2-alkyl-4-methoxy-5-substitué aminophénol ou sel de ce dernier, et composition tinctoriale pour fibres kératiniques le contenant
WO1993000066A1 (fr) * 1991-06-26 1993-01-07 L'oreal Meta-aminophenols, leur utilisation en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques, compositions et procede de teinture

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4125601A (en) * 1976-04-21 1978-11-14 L'oreal Substituted nitroaminophenols, process for their preparation and dyeing compositions in which they are present
EP0410471A2 (fr) * 1989-07-28 1991-01-30 Kao Corporation 2-alkyl-4-methoxy-5-aminophénol ou sel de ce dernier, ou 2-alkyl-4-methoxy-5-substitué aminophénol ou sel de ce dernier, et composition tinctoriale pour fibres kératiniques le contenant
WO1993000066A1 (fr) * 1991-06-26 1993-01-07 L'oreal Meta-aminophenols, leur utilisation en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques, compositions et procede de teinture

Also Published As

Publication number Publication date
AU1152599A (en) 1999-05-10
DE19746249A1 (de) 1999-04-22

Similar Documents

Publication Publication Date Title
EP0966449B1 (fr) Derives de 1,4-diazacycloheptane et leur utilisation dans des colorants capillaires d'oxydation
EP1233744B1 (fr) Agent pour colorer des fibres a base de keratine
WO2000038631A1 (fr) Agents permettant de colorer les fibres de keratine
DE10144226A1 (de) Neue verbrückte p-Phenylendiamine
EP1041955B1 (fr) Utilisation de complexes de metaux de transition pour teindre des fibres keratiniques
EP0832640B1 (fr) Composition de teinture d'oxydation des fibres kératiniques
EP1037592B1 (fr) Nouvelles combinaisons d'agents de developpement pour colorants d'oxydation
WO2000038629A1 (fr) Produits de coloration de fibres keratiniques
EP1044185A2 (fr) Nouveuax derives de p-aminophenol et leur utilisation
EP1200048B1 (fr) Nouvelles associations generateur/copulant
EP1139991B1 (fr) Agent pour la coloration de fibres keratiniques
WO1999065891A1 (fr) Nouveaux derives de 2,4-diaminophenol et leur utilisation
WO1999020597A1 (fr) Nouveaux derives d'aminophenol et leur utilisation pour colorer des fibres a base de keratine
EP0971681B1 (fr) Produit et procede pour teinter et colorer des fibres de keratine
EP0873987B1 (fr) Dérivés perfluoroacylés de 3-Aminophénol et leur utilisation pour la teinture des cheveux
EP0979064B1 (fr) Colorants d'oxydation
EP1210060A2 (fr) Nouvelles combinaisons developpeur-coupleur
WO1999020231A2 (fr) UTILISATION D'α-NAPHTOLS SUBSTITUES POUR COLORER DES FIBRES A BASE DE KERATINE
WO1999065865A1 (fr) Nouveaux derives de 3,4-diaminophenol et leur utilisation
EP1185234A1 (fr) Agents de couplage pour colorations de cheveux a oxydation
EP1218344A2 (fr) Produits de depart colorants d'oxydation
EP1229891A1 (fr) Agent pour colorer des fibres a base de keratine

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU JP US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase