EP1768971A1 - Nouveaux derives de o-aminophenol, et colorants contenant ces composes - Google Patents

Nouveaux derives de o-aminophenol, et colorants contenant ces composes

Info

Publication number
EP1768971A1
EP1768971A1 EP05745013A EP05745013A EP1768971A1 EP 1768971 A1 EP1768971 A1 EP 1768971A1 EP 05745013 A EP05745013 A EP 05745013A EP 05745013 A EP05745013 A EP 05745013A EP 1768971 A1 EP1768971 A1 EP 1768971A1
Authority
EP
European Patent Office
Prior art keywords
amino
phenol
thienyl
group
methyl
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP05745013A
Other languages
German (de)
English (en)
Inventor
Laurent Chassot
Hans-Jürgen BRAUN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Deutschland GmbH
Original Assignee
Wella GmbH
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 Wella GmbH filed Critical Wella GmbH
Publication of EP1768971A1 publication Critical patent/EP1768971A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • 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
    • A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Definitions

  • the invention relates to novel o-aminophenol derivatives and agents containing these compounds for dyeing keratin fibers
  • oxidation dyes have gained substantial importance.
  • the coloration is formed by reaction of certain developer substances with certain coupler substances in the presence of a suitable oxidizing agent.
  • developers in particular 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenoi, 1, 4-diaminobenzene and 4,5-diamino-1- (2-hydroxyethyl) pyrazole are used, while as couplers, for example, resorcinol, 2 methyl-resorcinol, 1-naphthol, 3-aminophenol, m-phenylene diamine, 2-amino-4- (2 'hydroxyethyl) -amino-anisole, 1, 3-diamino-4- (2' - hydroxyethoxy) benzene and 2,4-diamino-5-fluoro-toluene are mentioned.
  • the dyes must be harmless from a toxicological and dermatological point of view, and the hair colorings obtained should have good fastness to lightfastness, durability, rubbing fastness and stability to shampooing, as well as sufficient resistance to perspiration.
  • a particular problem in the nuancing of lighter shades is the uniform dye uptake from the hairline to the tips of the hair and the durability of the nuances compared to a permanent wave treatment.
  • the use of substantive yellowing aromatic nitro dyes together with oxidative hair color precursors can solve the problems, in part,
  • the stability of the stains is often unsatisfactory over a period of several weeks.
  • DE-OS 28 33 989 proposes the use of 6-amino-3-methylphenol as oxidative yellowing agent in oxidative hair dyes.
  • This compound should have a good suitability as Nuancierfarbstoff for the production of light blond shades and gold tones, but the requirements are not fully met, especially with regard to the resistance of the hair dye to the action of permanent wave agents.
  • o-aminophenol derivatives according to the general formula (I) fulfill the requirements placed on color components to a particularly high degree.
  • the present invention therefore relates to o-aminophenol derivatives of the general formula (I) or their physiologically compatible, water-soluble salts,
  • X is oxygen, sulfur, or N-R4;
  • R 1, R 2, R 3 may be identical or different and independently of one another denote hydrogen, a halogen atom, a cyano group, a C 1 -C 4 -alkoxy group, a C 1 -C 6 -alkyl group, a C 1 -C 4 -alkyl thioether group, a mercapto group , a nitro group, a trifluoromethane group , a -C (O) H group, a -C (O) CH3 group, a
  • R 4 is hydrogen, a C 1 -C 6 -alkyl group, a C 1 -C 4 -hydroxyalkyl group, a phenyl group or an acetyl group.
  • Examples of compounds of the formula (I) which may be mentioned are the following compounds: 2-amino-5- (3-thienyl) phenol, 2-amino-5- (3-furyl) phenol, 2-amino-5- (pyrrole) 3-yl) phenol, 2-amino-5- (2-chloro-3-thienyl) phenol, 2-amino-5- (2-cyano-3-thienyl) phenol, 2-amino-5- (2-ethyl 3-thienyl) phenol, 2-amino-5- (2-formyl-3-thienyl) phenol, 2-amino-5- (2-methyl-3-thienyl) phenol, 2-amino-5- (2- trifluoromethyl-3-thienyl) phenol, 2-amino-5- (4-chloro-3-thienyl) phenol, 2-amino-5- (4-cyano-3-thienyl) phenol, 2-amino-5- (4-ethyl-3-thienyl) phenol
  • the compounds of the formula (I) can be present both as free bases and in the form of their physiologically tolerable salts with inorganic or organic acids, such as, for example, hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid or citric acid.
  • inorganic or organic acids such as, for example, hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid or citric acid.
  • the preparation of the o-aminophenol derivatives of the formula (I) according to the invention can be carried out using known synthesis methods; for example, by a palladium (O) -catalyzed coupling of a substituted benzene of the formula (II)
  • Rb is halogen and Rd is B (OH) 2 or Rb is B (OH) 2 and Rd is halogen;
  • Ra represents a protecting group as described, for example, in the chapter “Protective Groups” in Organic Synthesis, Chapter 3, Wiley Interscience, 1991, and X, R1, R2 and R3 have the meanings given in formula (I).
  • the compounds of the formula (I) according to the invention allow dyeings having excellent color fastness, in particular with regard to wash fastness and rubbing fastness, as well as to permanent wave fastness.
  • Another object of the present invention are therefore agents for the oxidative dyeing of keratin fibers, such as hair, furs, Feathers or wool, in particular human hair, containing at least one o-aminophenol derivative of the formula (I).
  • the o-aminophenol derivative of the formula (I) is contained in the colorant of the present invention in an amount of about 0.001 to 5% by weight, with an amount of about 0.005 to 2% by weight, and more preferably 0.01 to 1% by weight, being preferred.
  • the compounds of the formula (I) dye keratin fibers, in particular human hair, without the addition of further dyes in yellow shades.
  • one or more customary oxidative dyes for example developer substances or coupler substances, can be added alone or in a mixture with one another.
  • the developer substances are preferably 1,4-diaminobenzene (p-phenylenediamine), 1,4-diamino-2-methylbenzene (p-toluenediamine), 1,4-diamino-2,6-dimethylbenzene, 1, 4-diamino-3,5-diethylbenzene, 1,4-diamino-2,5-dimethylbenzene, 1,4-diamino-2,3-dimethylbenzene, 2-chloro-1,4-diaminobenzene, 1,4-diamino-2- (thiophen-2-yl) benzene, 1,4-diamino-2- (thiophen-3-yl) benzene, 4- (2,5-diaminophenyl) -2 - ((diethyl) amino) methyl) thiophene, 2-chloro-3- (2,5-diaminophenyl) thiophene, 2-
  • the total amount of the aforementioned developer substances and coupler substances in the composition according to the invention is about 0.01 to 12 percent by weight, in particular about 0.2 to 6 percent by weight.
  • the colorant according to the invention may additionally contain other color components, for example 4- (2,5-diamino-benzylamino) -aniline or 3- (2,5-diamino-benzylamino) -aniline, and also conventional natural, nature-identical or synthetic substantive dyes from the A group of anionic (acidic) and cationic (basic) dyes containing triarylmethane dyes, nitro dyes, disperse dyes and azo dyes, for example natural dyes such as indigo or henna, triphenylmethane dyes such as 4 - [(4'-amino-phenyl) - ( 4 I imino-2 ", 5" -cyclohexadien-1 "-ylidene) -methyl] -2-methyl-aminobenzene monohydrochloride (CI 42 510) and 4 -.
  • anionic (acidic) and cationic (basic) dyes containing triarylmethane dyes,
  • aromatic nitro dyes such as 4- (2'-hydroxyethyl) amino-nitrotoluene, 2-amino-4,6-dinitrophenol, 2-amino-5- (2'-hydroxyethyl) amino-nitrobenzene, 2-chloro-6- (ethylamino) -4-nitrophenol, 4-chloro-N- (2-hydroxyethyl) -2-nitroaniline, 5-chloro-2-hydroxy-4-nitroaniline, 2-amino-4-chloro-6-nitrophenol and 1 - [(2'-ureidoethyl) amino 4-nitrobenzene, azo dyes such as 6 - [(4'-amino-phenyl
  • the colorant preferably contains the aforementioned other color components in a total amount of about 0.1 to 4% by weight.
  • the coupler substances and developers and the other color components if they are bases, in the form of their physiologically acceptable salts with organic or inorganic acids such as hydrochloric acid or sulfuric acid, or - if they have aromatic OH groups - in Form of salts with bases, for example as Alkaliphenolate used.
  • the colorants if they are to be used for dyeing hair, other conventional cosmetic additives, such as antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite, and perfume oils, complexing agents, wetting agents, emulsifiers, thickeners and conditioners may be included.
  • the preparation form of the colorant according to the invention can be, for example, a solution, in particular an aqueous or aqueous-alcoholic solution, a paste, a cream, a gel, an emulsion or an aerosol preparation.
  • Their composition is a mixture of the dye components with the usual additives for such preparations.
  • Typical additives in solutions, creams, emulsions or gels are, for example, solvents such as water, lower aliphatic alcohols, for example ethanol, propanol or isopropanol, glycerols or glycols such as 1,2-propylene glycol, furthermore wetting agents or emulsifiers from the classes of anionic, cationic, amphoteric or nonionic surface-active substances such as fatty alcohol sulfates, ethoxylated fatty alcohol sulfates, alkyl sulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, alkylbetaines, ethoxylated fatty alcohols, ethoxylated nonylphenols, fatty acid alkanolamides and ethoxylated fatty acid esters, further thickeners such as higher fatty alcohols, starch, cellulose derivatives, petrolatum, paraffin oil and fatty acids, as well
  • constituents mentioned are used in the quantities customary for such purposes, for example the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight, the thickeners in an amount of about 0.1 to 30 percent by weight and the conditioners in a concentration of about 0.1 to 5 percent by weight.
  • the colorant of the invention may be slightly acidic, neutral or alkaline.
  • it has a pH of 6.5 to 11, 5, the basic setting preferably with ammonia or organic amines, for example monoethanolamine and triethanolamine, or else amino acids or inorganic bases such as sodium hydroxide and potassium hydroxide.
  • ammonia or organic amines for example monoethanolamine and triethanolamine
  • amino acids or inorganic bases such as sodium hydroxide and potassium hydroxide.
  • inorganic or organic acids for example phosphoric acid, acetic acid, citric acid or tartaric acid come into consideration.
  • the above-described coloring agent is mixed with an oxidizing agent immediately before use and a sufficient amount for the hair dyeing treatment, depending on hairiness, generally about 60 to 200 grams, of this mixture on the hair.
  • the oxidizing agent for the development of hair coloring are mainly hydrogen peroxide or its addition compounds of urea, melamine, sodium borate or sodium carbonate in the form of a 3- to 12prozentigen, preferably ⁇ prozentigen, aqueous solution, but also atmospheric oxygen into consideration.
  • a ⁇ prozentige hydrogen peroxide solution is used as the oxidizing agent, the weight ratio between hair dye and oxidizing agent is 5: 1 to 1: 2, but preferably 1: 1. Larger amounts of oxidizing agent, especially at higher dye concentrations in Haarfetzbe ⁇ medium, or if at the same time a greater bleaching of the hair is intended used.
  • the mixture is allowed to act on the hair at 15 to 50 degrees Celsius for about 10 to 45 minutes, preferably 30 minutes, then the hair is rinsed with water and dried.
  • a Washed shampoo and rinsed if necessary with a weak organic acid, such as citric acid or tartaric acid. Then the hair is dried.
  • hair colorants according to the invention containing o-aminophenol derivatives of the formula (I) enable hair colorations with excellent color fastness, in particular with regard to light fastness, wash fastness and rubbing fastness, and also permanent wave fastness.
  • hair colorants according to the invention depending on the nature and composition of the color components, offer a wide range of different color shades, ranging from blond to brown, purple, violet and even blue and black shades.
  • the compounds of formula (I) with 4- (2,5-diaminobenzylamino) -aniline it is possible to achieve blonde to brown hair dyeings.
  • the shades are characterized by their special color intensity and a good color balance between damaged and undamaged hair.
  • the very good dyeing properties of the hair dyeing compositions according to the present application are further demonstrated by the fact that these compositions enable the dyeing of graying, chemically undamaged hair without problems and with good hiding power.
  • reaction mixture is poured into 50 ml of ethyl acetate, the organic phase extracted with dilute sodium hydroxide solution and then dried with magnesium sulfate.
  • the solvent is distilled off on a rotary evaporator and the residue was purified on silica gel with hexane / ethyl acetate (9: 1).
  • the product thus obtained is heated to 50 ° C. in 20 ml of ethanol.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Abstract

L'invention concerne des dérivés de o-aminophénol correspondant à la formule générale (I), ou bien leurs sels hydrosolubles physiologiquement compatibles. Dans ladite formule (I): X représente oxygène, soufre ou N-R4; R1, R2, R3 peuvent être identiques ou différents et représentent hydrogène, un atome d'halogène, un groupe cyano, un groupe alcoxy C<sub
EP05745013A 2004-07-20 2005-05-18 Nouveaux derives de o-aminophenol, et colorants contenant ces composes Withdrawn EP1768971A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004035164A DE102004035164A1 (de) 2004-07-20 2004-07-20 Neue o-Aminophenol-Derivate und diese Verbindungen enthaltende Färbemittel
PCT/EP2005/005380 WO2006007896A1 (fr) 2004-07-20 2005-05-18 Nouveaux derives de o-aminophenol, et colorants contenant ces composes

Publications (1)

Publication Number Publication Date
EP1768971A1 true EP1768971A1 (fr) 2007-04-04

Family

ID=34968249

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05745013A Withdrawn EP1768971A1 (fr) 2004-07-20 2005-05-18 Nouveaux derives de o-aminophenol, et colorants contenant ces composes

Country Status (10)

Country Link
US (1) US7641702B2 (fr)
EP (1) EP1768971A1 (fr)
JP (1) JP2008506726A (fr)
CN (1) CN1997637A (fr)
AU (1) AU2005263355A1 (fr)
BR (1) BRPI0513490A (fr)
CA (1) CA2572753A1 (fr)
DE (1) DE102004035164A1 (fr)
MX (1) MX2007000462A (fr)
WO (1) WO2006007896A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016132776A (ja) * 2015-01-22 2016-07-25 ホーユー株式会社 芳香族化合物の安定性向上剤及び芳香族化合物の安定性向上方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2833989A1 (de) 1978-08-03 1980-02-21 Wella Ag Mittel zum faerben von haaren
DE10022828A1 (de) * 2000-05-10 2001-11-22 Wella Ag Neue p-Aminophenole und diese Verbindungen enthaltende Färbemittel
DE10141723A1 (de) * 2001-08-25 2003-03-06 Wella Ag m-Aminophenol-Derivate und diese Verbindung enthaltende Färbemittel
DE10251106A1 (de) * 2002-11-02 2004-05-19 Wella Ag 4-Amino-biphenyl-3-ol-Derivate enthaltende Mittel zum Färben von Keratinfasern

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006007896A1 *

Also Published As

Publication number Publication date
US7641702B2 (en) 2010-01-05
BRPI0513490A (pt) 2008-05-06
DE102004035164A1 (de) 2006-02-09
CN1997637A (zh) 2007-07-11
CA2572753A1 (fr) 2006-01-26
MX2007000462A (es) 2007-03-29
US20080235882A1 (en) 2008-10-02
JP2008506726A (ja) 2008-03-06
AU2005263355A1 (en) 2006-01-26
WO2006007896A1 (fr) 2006-01-26

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