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WO1997030968A1 - Nouveaux derives d'aminophenol et leur utilisation - Google Patents

Nouveaux derives d'aminophenol et leur utilisation Download PDF

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Publication number
WO1997030968A1
WO1997030968A1 PCT/EP1997/000650 EP9700650W WO9730968A1 WO 1997030968 A1 WO1997030968 A1 WO 1997030968A1 EP 9700650 W EP9700650 W EP 9700650W WO 9730968 A1 WO9730968 A1 WO 9730968A1
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Prior art keywords
group
aminophenol
alkyl group
hydrogen
stands
Prior art date
Application number
PCT/EP1997/000650
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German (de)
English (en)
Inventor
David Rose
Bernd Meinigke
Horst Höffkes
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Filing date
Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to AU17246/97A priority Critical patent/AU1724697A/en
Publication of WO1997030968A1 publication Critical patent/WO1997030968A1/fr

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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
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
    • C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/32—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using oxidation dyes

Definitions

  • the invention relates to new ammophenol derivatives, their use for dyeing keratin fibers and dyes containing these compounds
  • oxidation colorants For dyeing keratin fibers, in particular 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
  • oxidation dye precursors must first of all meet the following requirements. You have to develop the desired color shades with sufficient intensity and fastness in the oxidative coupling. You also have to have a good ability to draw on the fiber, whereby especially with human hair there may be no noticeable differences between stressed and newly regrown hair (leveling ability). They should be resistant to light, heat and the influence of chemical reducing agents, for example permanent fluids. Finally, if they are used as hair colorants, they should not stain the scalp too much and, above all, they should be harmless in toxicological and dermatological terms
  • p ⁇ mare aromatic amines are usually used with other free or sub-positions in the para or ortho position.
  • tuie ⁇ en hydroxyl or amino group diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives used.
  • 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, l-phenyl-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-methyl-resorcinol and 5-methyl-resorcinol.
  • a first subject of the present invention are therefore aminophenol derivatives of the general formula (I)
  • R 2 stands for fluorine, chlorine or bromine
  • R 3 stands for
  • R 5 , R 6 , R 7 , R 8 , R 10 and R 11 independently of one another represent hydrogen, a C 1 -C 4 -alkyl group, a C M -hydroxyalkyl group and R 5 and R 6 , R 7 and R 8 and R 10 and R 1 ', together with the nitrogen atom carrying them, can also be part of a morpholino, piperidino or pyrrolidino radical and R 5 also for a group -S0 2 -CH 3 can be provided that then R 6 stands for hydrogen, and R 9 stands for hydrogen or a C H alkyl group, and R 4 stands for hydrogen, a C M alkyl group or one of the groups mentioned under R 3 , and their water-soluble salts
  • R 1 represents a C 1.3 alkyl group or an allyl group.
  • Compounds with R 1 equal to methyl have proven to be very particularly suitable.
  • Halogenated C M alkyl groups in particular with a terminal trifluoromethyl group, are particularly suitable as substituents R 3 .
  • 2-chloro-6-methyl-3-N-ß-hydroxyethylaminophenol has particularly good properties.
  • a second subject of the present invention is the use of the abovementioned aminophenol derivatives as a coupler component in oxidation hair colorants.
  • a third object of the present invention are oxidation colorants for dyeing keratin fibers containing coupler components and developer components in a water-containing carrier, which contains one of the aforementioned aminophenol derivatives as a coupler component.
  • Keratin fibers are to be understood here 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.
  • Particularly preferred developer components are 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triarnmopyrimidine, l- ( ⁇ -hydroxyemyl) -2,5-diaminobenzene, p-phenylenediamine, p-toluenediamine, p- Aminophenol, 3-methyl-p-aminophenol and 2-an ⁇ nomethyl-p-aminophenol.
  • 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, based in each case on the entire 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 dye compositions according to the invention contain, in addition to the oxidation dye precursors, customary direct dyes, e.g. from the group of nitrophenylenediamines, nitroaminophenols, anthraquinones or indophenols, such as e.g.
  • 4-Amino-2-nifro-diphenylamine-2'-carboxylic acid, 6-nitro-1,2,3,4-tetrahydroquinoxaline, Rodol 9 R and HC Red BN are particularly preferred direct dyes according to the invention.
  • the hair colorants according to the invention can also contain further components in subordinate amounts, insofar as these are not adversely affect the coloring result or must be excluded for other reasons, e.g. toxicological.
  • the oxidation dye precursors are incorporated into a suitable water-containing carrier.
  • suitable water-containing carrier e.g. Creams, emulsions, gels or also surfactant-containing foaming solutions, e.g. Shampoos, aerosols or other preparations that 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, with 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 addition products of about 2-15 molecules of ethylene oxide and / or propylene oxide onto 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 C8-C22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one -COO - or -S0 3 group in the molecule.
  • Particularly suitable secondary surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyl-dimethylammomum glycinate, N-acyl-ammopropyl-N, N-dimethylammonium glycinate, for example the cocoacylammopropyl-dimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazoIine each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoemylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C 8 -C 8 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-coconut alkyl aminopropionate, coconut acylaminoethyl aminopropionate and C -
  • 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 Addition products of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles
  • Adducts of 5 to 60 moles of ethylene oxide with castor oil and hardened castor oil Adducts of 5 to 60 moles of ethylene oxide with castor oil and hardened castor oil
  • 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 trimethylammonium chlorides, diaucyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B. cetyltrimethylammonium chloride, stearyltrimethylammomum chloride, disteatyldmethylammonium chloride, lauryldimemylammonium chloride, lauryldimethylbenzylammomum chloride and
  • 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) will), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th. Gold ⁇ schmidt; diquaternary polydimethylsiloxanes, Quaternium-80).
  • Alkylaimdoamines in particular fatty acid amidoamines such as the stearylamidopropyldimethylamine available under the name Tego Amid ® S 18, are characterized not only by a good conditioning effect but also by their good biodegradability.
  • Glucquat ® 100 is, 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, vinylpy ⁇ olidone / vinyl acrylate copolymers, polyvinylpy ⁇ olidone and vinylpy ⁇ olidone / vinyl acetate copolymers and polysiloxanes
  • cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallyl polymers, dimethyldiallyl -Dimethyldiallylammonium chloride copolymers, dimethylammoemytaethacrylate-vinylpy ⁇ olidone copolymers quaternized with diethyl sulfate,
  • Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as. B.
  • hydrocolloids such as polyvinyl alcohol, structurants such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins, and silicone oils, protein hydrolyzates, in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolyzates, their condensation products with fatty acids and quaternized protein hydrolysates, perfume and cyclodextrins,
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol, dyes for coloring the preparations, 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, py ⁇ olidone 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 glycerin, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates, 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 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; For example, 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 if, 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 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 (e.g. 1% 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.
  • 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, such as a coloring shampoo, has been used.
  • 3rd stage 2-chloro-6-memyl-3-N- ⁇ -hydroxyethylaminophenol 6.8 g (0.03 mol) of the product from stage 2 were introduced at 70 ° C. in 20 ml of 5N NaOH solution. After 30 minutes at this temperature, the mixture was cooled to 0 ° C. and neutralized with concentrated acetic acid. The product was dried under vacuum at 60 ° C in a vacuum; it had a melting point of 104 ° C. 1.2. 2-chloro-6-methyl-3-N-carbethoxyaminophenol fK2)
  • Cetylstearyl alcohol with approx. 20 mol EO (CTFA name: Ceteareth-20) (HENKEL)
  • 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 solution was then made up to 100 g with water.
  • the oxidative development of the color was carried out using a 3% hydrogen peroxide solution as the oxidation solution.
  • 100 g of the emulsion were mixed with 50 g of hydrogen peroxide solution (3%) 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 had ended, the hair was rinsed, washed with a customary shampoo and then dried.

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Abstract

Dérivés d'aminophénol de formule (I), dans laquelle R1 représente un groupe alkyle C¿1-4?, un groupe hydroxyalkyle C1-4, un groupe alcoxy C1-4, ou un groupe allyle; R?2¿ représente fluor, chlore ou brome; R3 représente un groupe dihydroxyalkyle C¿3-4?, un groupe méthyle comportant en tant que substituants 1 à 3 atomes d'halogène, notamment des atomes de fluor, un groupe alkyle C1-4, comportant en tant que substituants au maximum 1 à 4 atomes d'halogène, notamment des atomes de fluor, un groupe -(CH2)x-B (dans lequel B représente un groupe hydroxy, un groupe NR?5R6¿ ou un groupe CO-NR7R8 et x représente un nombre compris entre 1 et 4), un groupe -COOR9 ou un groupe -CO-NR?10R11; R5, R6, R7, R8, R10 et R11¿ représentent indépendamment l'un de l'autre hydrogène, un groupe alkyle C¿1-4?, un groupe hydroxyalkyle, et R?5 et R6, R7 et R8, R10 et R11¿ peuvent, avec l'atome d'azote qu'il comporte, faire également partie respectivement d'un radical morpholino, pipéridino ou pyrrolidino, et R5 peut également représenter un groupe -SO¿2?-CH3, à condition que R?6¿ représente hydrogène, et R9 représente hydrogène ou un groupe alkyle C¿1-4?, et R?4¿ représente hydrogène, un groupe alkyle C¿1-4? ou un des groupes désignés par R?3¿. Lesdits dérivés et leurs sels hydrosolubles se prêtent particulièrement bien à des applications en tant que constituants d'agents de couplage dans des colorants d'oxydation pour les cheveux. En fonction des composants de développement sélectionnés, ils offrent une gamme exceptionnellement étendue de teintes brillantes.
PCT/EP1997/000650 1996-02-22 1997-02-13 Nouveaux derives d'aminophenol et leur utilisation WO1997030968A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU17246/97A AU1724697A (en) 1996-02-22 1997-02-13 Novel aminophenol derivatives and their use

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP19606644.1 1996-02-22
DE1996106644 DE19606644A1 (de) 1996-02-22 1996-02-22 Neue Aminophenol-Derivate und deren Verwendung

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WO1997030968A1 true WO1997030968A1 (fr) 1997-08-28

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003087034A1 (fr) * 2002-04-18 2003-10-23 Wella Aktiengesellschaft Derives de 3-aminophenol substitues en position 2 et colorants contenant lesdits composes

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19717293A1 (de) * 1997-04-24 1998-10-29 Henkel Kgaa Perfluoracylierte 3-Aminophenol-Derivate und deren Verwendung in Haarpflegemitteln
US6040482A (en) * 1999-03-05 2000-03-21 Milliken & Company Oxyalkylene-substituted aminophenol intermediate
DE19936442A1 (de) * 1999-08-03 2001-02-08 Henkel Kgaa Neue Entwickler-Kuppler-Kombinationen
ATE456965T1 (de) * 2005-08-12 2010-02-15 Procter & Gamble Haarfärbemittel enthaltent m-aminophenolderivate

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Publication number Priority date Publication date Assignee Title
EP0023257A1 (fr) * 1979-06-15 1981-02-04 Henkel Kommanditgesellschaft auf Aktien Dichloro-hydroxyéthylaminophénols, procédé pour leur préparation, leur utilisation et compositions tinctoriales pour cheveux les contenant
EP0039030A1 (fr) * 1980-04-25 1981-11-04 Henkel Kommanditgesellschaft auf Aktien Composants copulants pour la teinture oxydante des cheveux, leur préparation et leur application ainsi que les compositions tinctoriales les contenant
DE3524329A1 (de) * 1985-07-08 1987-01-08 Henkel Kgaa Neue aminophenole und deren verwendung in oxidationshaarfaerbemitteln
EP0269914A1 (fr) * 1986-12-04 1988-06-08 Wella Aktiengesellschaft Composition et procédé de teinture oxydative pour cheveux à base de dérivés 3-(2',2',2'-trifluoréthyl)amino-phényle et dérivés 3-(2',2',2'-trifluoréthyl)amino-phényle

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0023257A1 (fr) * 1979-06-15 1981-02-04 Henkel Kommanditgesellschaft auf Aktien Dichloro-hydroxyéthylaminophénols, procédé pour leur préparation, leur utilisation et compositions tinctoriales pour cheveux les contenant
EP0039030A1 (fr) * 1980-04-25 1981-11-04 Henkel Kommanditgesellschaft auf Aktien Composants copulants pour la teinture oxydante des cheveux, leur préparation et leur application ainsi que les compositions tinctoriales les contenant
DE3524329A1 (de) * 1985-07-08 1987-01-08 Henkel Kgaa Neue aminophenole und deren verwendung in oxidationshaarfaerbemitteln
EP0269914A1 (fr) * 1986-12-04 1988-06-08 Wella Aktiengesellschaft Composition et procédé de teinture oxydative pour cheveux à base de dérivés 3-(2',2',2'-trifluoréthyl)amino-phényle et dérivés 3-(2',2',2'-trifluoréthyl)amino-phényle

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A. P. KOZIKOWSKI ET AL.: "EFFECT OF ALTERATION OF THE HETEROCYCLIC NUCLEUS OF ILV ON ITSISOFORM SELECTIVITY FOR PKC. PALLADIUM-CATALYZED ROUTE TO BENZOFURAN ANALOGUES OF ILV.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 117, 1995, WASHINGTON, D.C., pages 6666 - 6672, XP002030322 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003087034A1 (fr) * 2002-04-18 2003-10-23 Wella Aktiengesellschaft Derives de 3-aminophenol substitues en position 2 et colorants contenant lesdits composes
US7033401B2 (en) 2002-04-18 2006-04-25 Wella Ag 3-Aminophenol derivatives substituted in the 2-position, and dyes containing these compounds

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DE19606644A1 (de) 1997-08-28
AU1724697A (en) 1997-09-10

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