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EP1353640A1 - Nouveaux copulants pour colorants d'oxydation - Google Patents

Nouveaux copulants pour colorants d'oxydation

Info

Publication number
EP1353640A1
EP1353640A1 EP02715451A EP02715451A EP1353640A1 EP 1353640 A1 EP1353640 A1 EP 1353640A1 EP 02715451 A EP02715451 A EP 02715451A EP 02715451 A EP02715451 A EP 02715451A EP 1353640 A1 EP1353640 A1 EP 1353640A1
Authority
EP
European Patent Office
Prior art keywords
group
amino
alkyl
bis
hydroxy
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Withdrawn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
EP02715451A
Other languages
German (de)
English (en)
Inventor
David Rose
Horst Höffkes
Bernd Meinigke
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1353640A1 publication Critical patent/EP1353640A1/fr
Withdrawn legal-status Critical Current

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
    • A61K8/49—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
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings

Definitions

  • Good oxidation dye precursors are primarily intended to meet the following requirements: They have to 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, with no noticeable differences between stressed and freshly regrown hair, especially with human hair (leveling ability). They should be resistant to light, heat, friction and the influence of chemical reducing agents, e.g. Perm liquids. 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. Furthermore, the coloration obtained should be easily removed from the hair again by bleaching, if it does not correspond to the individual wishes of the individual and should be reversed.
  • the color shades in the red and brown areas are of particular importance, since they are absolutely necessary to produce natural-looking hair colors.
  • Oxidation colorants in the red and brown areas such as those e.g. with the combination of 2,4,5,6-tetraaminopyrimidine with 2-methylresorcinol are not yet optimal with regard to the uniformity of the color coating.
  • Direct dyes are usually less washfast and therefore not so well suited for combination with oxidation dyes.
  • a first object of the invention is therefore an agent for dyeing keratin fibers, in particular human hair, which contains at least one developer component and at least one coupler component in a carrier suitable for dyeing, characterized in that it contains at least one compound of the formula I or the like as a coupler component contains appropriate physiologically compatible salt,
  • R 1 represents hydrogen, a C 1 -C 4 alkyl group, a C ⁇ -C 4 perfluoroalkyl group, a C 2 -C 4 monohydroxyalkyl group, a C 2 -C 5 polyhydroxyalkyl group, a C 2 -
  • Physiologically acceptable salts include salts of inorganic or organic acids, e.g. B. hydrochlorides, sulfates or hydrobromides understood.
  • R 1 represents hydrogen, a - C 4 alkyl group, a benzyl group, a C -C 4 alkenyl group or a C 2 -C 4 monohydroxyalkyl group.
  • G 1 represents a hydrogen atom, a C 1 -C 4 alkyl group, a C ⁇ -C 4 - monohydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a (C ⁇ -C) alkoxy (C -C 4! alkyl radical, a 4'-aminophenyl radical or a C 1 -C 4 -alkyl radical which is substituted by a nitrogen-containing group, a phenyl or a 4'-aminophenyl radical,
  • Examples of the C 1 -C 4 -alkyl radicals mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl are preferred alkyl radicals.
  • Preferred C 1 -C 4 alkoxy radicals according to the invention are, for example, a methoxy or an ethoxy group.
  • Further preferred examples of a C 1 -C 4 monohydroxyalkyl group are a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group. A 2-hydroxyethyl group is particularly preferred.
  • An example of a preferred C 2 -C 4 polyhydroxyalkyl group is the ⁇ , ⁇ -dihydroxyethyl group.
  • halogen atoms according to the invention are F, Cl or Br atoms, Cl atoms are very particularly preferred.
  • the other terms used are derived from the definitions given here.
  • nitrogen-containing groups of formula (II) are especially the amino groups, C ⁇ -C4 monoalkylamino, C ⁇ -C 4 dialkylamino, C ⁇ -C 4 - trialkylammonium, C ⁇ -C 4 -Monohydroxyalkylamino phenomenon, imidazolinium and ammonium.
  • the bridge Y stands for an alkylene group with 1 to 14 carbon atoms, such as a linear or branched alkylene chain or an alkylene ring which is interrupted or terminated by one or more nitrogen-containing groups and / or one or more heteroatoms such as oxygen, sulfur or nitrogen atoms may be and may be substituted by one or more hydroxyl or -CC 8 alkoxy groups, or a direct bond,
  • the developer component can be selected from o-aminophenol and its derivatives, such as, for example, 2-amino-4-methylphenol or 2-amino-4-chlorophenol.
  • the developer component can be selected from heterocyclic developer components, such as, for example, the pyridine, pyrimidine, pyrazole, pyrazole-pyrimidine derivatives and their physiologically tolerable salts.
  • heterocyclic developer components such as, for example, the pyridine, pyrimidine, pyrazole, pyrazole-pyrimidine derivatives and their physiologically tolerable salts.
  • pyrimidine or pyrazole derivatives are preferred.
  • Methoxyethyl amino-3-amino-6-methoxy-pyridine and 3,4-diamino-pyridine.
  • a Cj-C 4 - aminoalkyl radical which can optionally be protected by an acetyl-ureide or sulfonyl radical, a (-C-C 4 ) alkylamino (dC 4 ) alkyl radical, a di - [(dC 4 ) - alkyl] - (dC 4 ) aminoalkyl radical, where the dialkyl radicals optionally form a carbon cycle or a heterocycle with 5 or 6 chain links, a d- C 4 -monohydroxyalkyl- or a di- (-C-C 4 ) - [hydroxyalkyl] - (C 1 -C 4 ) aminoalkyl radical, the X radicals are each independently a hydrogen atom, a dC 4 - alkyl group, an aryl group, a C ⁇ -C 4 monohydroxyalkyl radical, a C 2 -C 4 - polyhydroxyalkyl group, a C ⁇ -C 4 aminoalkyl radical
  • dialkyl radicals optionally having a carbon cycle or a heterocycle with 5 or Form 6 chain links, a C 1 -C 4 monohydroxyalkyl or a di (C) -C 4 - hydroxyalkyl) aminoalkyl radical, an amino radical, a C ! -C 4 - alkyl or di (dC 4 - hydroxyalkyl) amino radical, a halogen atom, a carboxylic acid group or a sulfonic acid group, i has the value 0, 1, 2 or 3,
  • n has the value 0, and the groups NG 17 G 18 and NG 19 G 20 occupy positions (2,3); (5,6); (6,7); (3.5) or (3.7);
  • pyrazole [1,5-a] pyrimidines of the above formula (E4) can be prepared as described in the literature by cyclization starting from an aminopyrazole or from hydrazine.
  • m-phenylenediamine derivatives naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are used in particular as further coupler components.
  • m-aminophenol and its derivatives such as 5-amino-2-methylphenol, N-cyclopentyl-3-aminophenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 2 , 6-Dimethyl-3-aminophenol, 3-trifluoroacetylamino-2-chloro-6-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5- (2 ' -Hydroxyethyl) amino-2-methylphenol, 3- (diethylamino) phenol, N-cyclopentyl-3-aminophenol, 1,3-dihydroxy-5- (methylamino) benzene, 3-ethylamino-4-methylphenol and 2, 4-dichloro-3-aminophenol, o-aminophenol and its derivatives, m-diaminobenzene and its derivatives such as
  • R 5 stands for one of the groups mentioned under R 4 , as well as physiologically tolerable salts of these compounds with an organic or inorganic acid.
  • aqueous-alcoholic solutions are to be understood as meaning aqueous solutions containing 3 to 70% by weight of a dC 4 alcohol, in particular ethanol or isopropanol.
  • the agents according to the invention can additionally contain other organic solvents, such as methoxy butanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol. All water-soluble organic solvents are preferred.
  • Ether carboxylic acids of the formula RO- (CH 2 -CH 2 O) x -CH 2 -COOH, in which R is a linear one
  • Ampholytic surfactants are also particularly suitable as co-surfactants.
  • 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 3 H group in the molecule and are capable of forming internal salts are.
  • Anti-dandruff agents such as piroctone olamine, zinc omadine and climbazole, light stabilizers, in particular derivatized benzophenones, cinnamic acid derivatives and triazines.
  • Opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate, pigments,
  • the coloring cream obtained after 1 was used without additional oxidizing agent (air oxidation) or the coloring cream obtained after 1 was mixed in a ratio of 2: 1 with a 1% or 9% H 2 O 2 solution and was 5 cm long Strands of standardized, 80% gray, but not specially pretreated human hair (Kerling) applied. After an exposure time of 30 minutes at 32 ° C., the hair was rinsed, washed out with a customary shampoo and then dried.
  • Table II speak received received received received speak

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (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 des dérivés de 1,2,3,4-tétrahydroquinoléine de formule (I) dans laquelle R<1> représente hydrogène, un groupe alkyle C1-C4, un groupe perfluoralkyle C1-C4, un groupe monohydroxyalkyle C2-C4, un groupe polyhydroxyalkyle C2-C5, un groupe alcényle C2-C4, un groupe aminoalkyle C2-C4, un groupe benzyle, un groupe pipéridinoalkyle ou un groupe morpholinoalkyle ; R<2>, R<3>, R<4> et R<5> représentent indépendamment les uns des autres hydrogène ou un groupe C1-C4-alkyle ou perfluoralkyle ; R<6> et R<8> représentent indépendamment l'un de l'autre hydrogène, halogène, un groupe alcoxy C1-C4, un groupe C1-C4-alkyle ou perfluoralkyle, un groupe C2-C4-monohydroxyalkyle ou un groupe C1-C5 Polyhydroxyalkyle ; R<7> représente hydrogène, halogène ou un groupe alcoxy C1-C4, A un groupe hydroxy, un groupe NR<9>R<10>, formule dans laquelle R<9> et R<10> représentent indépendamment l'un de l'autre hydrogène, un groupe alkyle C1-C4 ou un groupe monohydroxyalkyle C2-C4. Ces dérivés de 1,2,3,4-tétrahydroquinoléine et leurs sels physiologiquement acceptables sont utilisés comme copulants dans la production de colorants d'oxydation à teneur en révélateurs ou copulants classique dans un support approprié à la coloration. Pour la coloration, p. ex. de cheveux, on obtient des nuances de couleur résistantes au lavage et à la lumière intensive, dans la gamme du rouge au bleu.
EP02715451A 2001-01-27 2002-01-18 Nouveaux copulants pour colorants d'oxydation Withdrawn EP1353640A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10103657 2001-01-27
DE2001103657 DE10103657A1 (de) 2001-01-27 2001-01-27 Neue Kupplerkomponente für Oxidationsmittel
PCT/EP2002/000470 WO2002058652A1 (fr) 2001-01-27 2002-01-18 Nouveaux copulants pour colorants d'oxydation

Publications (1)

Publication Number Publication Date
EP1353640A1 true EP1353640A1 (fr) 2003-10-22

Family

ID=7671924

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02715451A Withdrawn EP1353640A1 (fr) 2001-01-27 2002-01-18 Nouveaux copulants pour colorants d'oxydation

Country Status (3)

Country Link
EP (1) EP1353640A1 (fr)
DE (1) DE10103657A1 (fr)
WO (1) WO2002058652A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7504508B2 (en) 2002-10-04 2009-03-17 Millennium Pharmaceuticals, Inc. PGD2 receptor antagonists for the treatment of inflammatory diseases
EA011385B1 (ru) 2002-10-04 2009-02-27 Миллениум Фармасьютикалз, Инк. Антагонисты рецептора pgd2 для лечения воспалительных заболеваний
EP1861372A1 (fr) 2005-02-24 2007-12-05 Millennium Pharmaceuticals, Inc. Antagonistes de recepteur de pgd2 pour le traitement des maladies inflammatoires
CN1907253A (zh) * 2006-08-23 2007-02-07 苏建华 用于毛发染色的含有氨基杂环化合物的组合物及染色方法
FR2957346B1 (fr) * 2010-03-12 2012-06-15 Oreal Nouvelles 7-amino-1,2,3,4-tetrahydroquinoleines cationiques, composition tinctoriale comprenantune 7-amino-1,2,3,4- tetrahydroquinoleine cationique, procedes et utilisations
FR2984318B1 (fr) 2011-12-16 2014-06-27 Oreal Coupleur de structure 7 amino-1,2,3,4-tetrahydroquinoleines cationiques, composition tinctoriale en comprenant, procedes et utilisations
FR2984323B1 (fr) * 2011-12-16 2019-08-30 L'oreal Coupleur de structure 7 amino-1,2,3,4-tetrahydroquinoleines, composition tinctoriale en comprenant, procedes et utilisations

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2441895A1 (de) * 1974-09-02 1976-03-11 Henkel & Cie Gmbh Haarfaerbemittel
DE2714955A1 (de) * 1977-04-02 1978-10-12 Henkel Kgaa Haarfaerbemittel
DE4314317A1 (de) * 1993-04-30 1994-11-03 Henkel Kgaa Isatinhaltige Mittel zum Färben von keratinhaltigen Fasern
DE4319646A1 (de) * 1993-06-14 1994-12-15 Henkel Kgaa 8-Amino-1,2,3,4-tetrahydrochinoline als Kuppler in Färbemitteln

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02058652A1 *

Also Published As

Publication number Publication date
DE10103657A1 (de) 2002-08-01
WO2002058652A1 (fr) 2002-08-01

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