EP0868165A1 - Moyens et procede de teinture de fibres keratiniques - Google Patents

Moyens et procede de teinture de fibres keratiniques

Info

Publication number
EP0868165A1
EP0868165A1 EP97909331A EP97909331A EP0868165A1 EP 0868165 A1 EP0868165 A1 EP 0868165A1 EP 97909331 A EP97909331 A EP 97909331A EP 97909331 A EP97909331 A EP 97909331A EP 0868165 A1 EP0868165 A1 EP 0868165A1
Authority
EP
European Patent Office
Prior art keywords
straight
chain
branched
carbon atoms
hair
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Withdrawn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
EP97909331A
Other languages
German (de)
English (en)
Inventor
Hans-Jürgen Dr. 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 EP0868165A1 publication Critical patent/EP0868165A1/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Withdrawn legal-status Critical Current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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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

Definitions

  • the present invention relates to a composition for coloring keratin fibers, in particular human hair.
  • These compositions contain at least one p-aminophenol, one m-aminophenol and one m-phenylene diamine.
  • the dyeings of the keratin fibers are carried out by the above-mentioned composition with an oxidizing agent mixed, applied to the keratin fibers and washed out with water and a shampoo after a certain exposure time
  • compositions which are able to dye hair in copper-colored, maroon to red shades are able to dye hair in copper-colored, maroon to red shades.
  • This demand is satisfied today by offering hair colorants with a content of certain oxidation dye precursors, for example in DE-OS 36 10 396 to produce neutral red shades the use of a combination of 5-amino-2-methylphenol, 4-amino-3-methylphenol and 1,4-diminobenzene and / or 2,5-diminotoluene specified in EP-OS 0 634 162 examples are given for the combination of 5-amino-2-methylphenol and its N-substituted derivatives, 4-amino-2-methylphenol, 4-amino-3-methylphenol or 4-amino-2-hydroxymethylphenol and certain m-phenylenediamine phenates
  • the resistance of the hair dyeings obtained according to the prior art to the effects of light, washing out, weather influences, sweat and other hair treatments is insufficient.
  • R 1 and R 2 are independently hydrogen, a straight-chain or branched alkyl radical, a straight-chain or branched hydroxyalkyl radical, a straight-chain or branched aminoalkyl radical, a straight-chain or branched mono- or dialkylaminoalkyl radical, a straight-chain or branched acylaminoalkyl radical, a straight-chain or branched aryl Alkylsulfonylaminoalkyl radical, a straight-chain or branched carbamidoalkyl radical, an acyl radical, an aryl radical, a straight-chain or branched alkylsulfonyl radical or a carbamoyl radical, where the alkyl radical in each case has 1 to 4 carbon atoms, or through R 1 and R 2 a heterocyclic non-aromatic Matic five- or six-membered ring, which may additionally have an oxo group, or the salts of the compounds mentioned;
  • radical R represents hydrogen, a straight-chain or branched alkyl group having 1 to 4 carbon atoms, a straight-chain or branched hydroxyalkyl group having 2 to 4 carbon atoms or a straight-chain or branched polyhydroxyalkyl group having 3 to 4 carbon atoms, and
  • R and R 2 independently of one another are a hydrogen atom, a straight-chain or branched alkyl group having 1 to 4 carbon atoms, a straight-chain or branched hydroxyalkyl group having 2 to 4 carbon atoms. atoms or a straight-chain or branched polyhydroxyalkyl group with 3 to 4 carbon atoms
  • R 3 denotes a hydrogen atom, a straight-chain or branched alkyl group with 1 to 6 carbon atoms, a straight-chain or branched alkoxy group with 1 to 4 carbon atoms, a straight-chain or branched hydroxyalkyl group with 2 means up to 4 carbon atoms or a straight-chain or branched polyhydroxyalkyl group with 3 to 4 carbon atoms, and
  • R 4 independently of R 1 t R 2 and R 3 is a hydrogen atom, a straight-chain or branched alkyl group having 1 to 6 carbon atoms, a straight-chain or branched alkoxy group having 1 to 4 carbon atoms, a straight-chain or branched hydroxyalkyl group having 2 to 4 carbon atoms or a straight-chain or branched polyhydroxyalkyl group having 3 to 4 carbon atoms.
  • Preferred derivatives according to general formula (I) are the compounds 4-amino-2-aminomethylphenol, 4-amino-2 - [(2'-hydroxyethyl) amino] phenol and 4-amino-2- (dimethylamino) phenol .
  • Preferred derivatives according to general formula (II) are the compounds 5-amino-2-methylphenol, 5-methylamino-2-methylphenol and 5 - [(2'-hydroxyethyl) amino] -2-methylphenol.
  • Preferred derivatives according to general formula (III) are the compounds 2,4-diamino-1- (2'-hydroxyethoxy) benzene, 2,4-diamino-1- (2 ', 3'-dihydroxypropoxy) benzene, 1, 3- Bis (2 ', 4'-diaminophenoxy) propane, 2-amino-4 - [(2'-hydroxyethyl) amino] anisole, 1, 5-bis (2'-hydroxyethoxy) -2,4-diaminobenzene and m-phenylenediamine .
  • the hair dye can contain further oxidation dye precursors, for example derivatives of p-phenylenediamine such as 2- (2 ', 5'-diaminophenyl) ethanol, resorcinol derivatives such as resorcinol or 4-chlororesorcinol, amino and hydroxy derivatives of 1 , 3-benzodioxole such as 5-hydroxy-1, 3-benzodioxole or 5 - ((2'-hydroxyethyl) amino) -1, 3-benzodioxole, naphthalene derivatives such as 1-hydroxynaphthalene, 1, 5-dihydroxynaphthalene or 1, 7-dihydroxynaphthalene as well as substantive dyes such as 2-amino-4,6-dinitrophenol, 2-ethylamino-4,6-dinitrophenol, 2 - [(2'-hydroxyethyl) amino] -4,6-dinitrophenol, 2-
  • the subject of the present application therefore also relates to an agent for the oxidative dyeing of hair, which is produced by mixing a colorant with an oxidizing agent immediately before use.
  • the paint carrier composition according to the invention contains the combinations of oxidative hair dyes and optionally direct dyes according to the invention described above as such or in the form of physiologically acceptable salts, for example hydrochloride or sulfates or in the case of phenols as alkali phenolates
  • the total concentration of dye precursors is 0.1 to 10 percent by weight, preferably 0.2 to 6 percent by weight.
  • concentration of the individual hair dyes is 0.01 to 5 percent by weight, preferably 0.1 to 4 percent by weight
  • customary cosmetic additives for example antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite, perfume oils, complexing agents, wetting agents, emulsifiers, thickeners, care substances and others, may also be present in the color carrier mass
  • the preparation form for the color carrier composition and for the ready-to-use oxidation hair dye can be, for example, a solution, in particular an aqueous or water-alcoholic solution.
  • the particularly preferred preparation forms are, however, a cream, a gel or an emulsion.
  • Their composition is a mixture of the dye components with those for them Preparations are common additives
  • Usual additives in solutions, creams, emulsions or gels are, for example, solvents such as water, lower aliphatic alcohols, for example ethanol, n-propanol and isopropanol or glycols such as glycerin and 1,2-propylene glycol, and also wetting agents or emulsifiers from the Classes of anionic, cationic, amphoteric or non-ionic surface-active substances such as fatty alcohol sulfates, ethoxylated fatty alcohol sulfates, alkyl sulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, alkylbetaines, oxyethylated fatty alcohols, oxethylated nonylphenols, fatty acid alkanolamides, oxyethylamides, oxyethylamides, ethoxylated fatty acid ethers, oxyethylamides,
  • constituents mentioned are used in the amounts customary for such purposes, for example the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight (based on the ink vehicle), the thickeners in an amount of about 0.1 to 25 percent by weight ( based on the ink carrier) and the care substances in a concentration of about 0.1 to 5.0 percent by weight (based on the ink carrier).
  • the ready-to-use hair dye according to the invention is produced by mixing the color carrier composition with a liquid oxidizing agent immediately before use.
  • the ink carrier mass and the oxidizing agent are mixed here in a weight ratio of 5: 1 to 1: 3, a weight ratio of 1: 1 to 1: 2 being particularly preferred.
  • the pH value of the ready-to-use hair colorant according to the invention is established when the color carrier composition, which is preferably made alkaline, is mixed with the oxidizing agent, which is usually made acidic a pH value which is influenced by the amounts of alkane in the paint carrier and the amounts of acid in the oxidizing agent and by the mixing ratio.
  • the pH of the finished hair dye can be 3 to 11, preferably 5 to 9
  • organic and inorganic acids such as phosphoric acid, ascorbic acid and lactic acid, or alkalis such as monoethanolamine, tetrahanolamine, 2- Am ⁇ no-2-methyl-1-propanol, ammonia, sodium hydroxide solution, potassium hydroxide solution or Tr ⁇ s (hydroxymethyl) -am ⁇ no-methane can be used.
  • alkalis such as monoethanolamine, tetrahanolamine, 2- Am ⁇ no-2-methyl-1-propanol, ammonia, sodium hydroxide solution, potassium hydroxide solution or Tr ⁇ s (hydroxymethyl) -am ⁇ no-methane
  • the above-described color carrier composition is mixed with an oxidizing agent immediately before use and an amount sufficient for the hair color treatment, depending on the amount of hair, is generally applied to the hair from about 60 to 200 grams of the ready-to-use oxidizing hair dye
  • the main oxidizing agents are hydrogen peroxide or its addition compounds with urea, melamine or sodium bromate in the form of a 1 to 12 percent, preferably 6 percent, aqueous solution, hydrogen peroxide being particularly preferred
  • the hair colorant according to the invention 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. If necessary, after this rinse, wash with a shampoo and, if necessary, rinse with a weak organic acid, such as citric acid or tartaric acid. The hair is then dried
  • this hair dye Shortly before use, 50 g of this hair dye is mixed with 50 ml of hydrogen peroxide solution (6 percent) and the mixture is left to 30 Soak in blonde human hair for minutes. Then rinse with water and then dry. An exceptionally intense, glowing red glow is obtained
  • the pH of the ink carrier composition is adjusted to 6.8 with dilute phosphoric acid or a dilute ammonia solution

Abstract

L'invention concerne une substance porteuse de teinture pour cheveux contenant au moins un dérivé de p-aminophénol selon la formule générale (I), au moins un dérivé de 5-amino-2-méthylphénol selon la formule générale (II), et au moins un dérivé de m-phénylènediamine selon la formule générale (III). L'invention concerne également une teinture pour les cheveux contenant cette substance porteuse de teinture ainsi qu'un procédé de coloration utilisant cette teinture pour cheveux.
EP97909331A 1996-10-18 1997-09-29 Moyens et procede de teinture de fibres keratiniques Withdrawn EP0868165A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19643060 1996-10-18
DE19643060A DE19643060A1 (de) 1996-10-18 1996-10-18 Mittel und Verfahren zur Färbung von keratinischen Fasern
PCT/EP1997/005342 WO1998017235A1 (fr) 1996-10-18 1997-09-29 Moyens et procede de teinture de fibres keratiniques

Publications (1)

Publication Number Publication Date
EP0868165A1 true EP0868165A1 (fr) 1998-10-07

Family

ID=7809135

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97909331A Withdrawn EP0868165A1 (fr) 1996-10-18 1997-09-29 Moyens et procede de teinture de fibres keratiniques

Country Status (6)

Country Link
US (1) US6224856B1 (fr)
EP (1) EP0868165A1 (fr)
JP (1) JP2000502368A (fr)
BR (1) BR9706882A (fr)
DE (1) DE19643060A1 (fr)
WO (1) WO1998017235A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19936442A1 (de) 1999-08-03 2001-02-08 Henkel Kgaa Neue Entwickler-Kuppler-Kombinationen
EP1331918A4 (fr) * 2000-08-30 2010-08-11 Clairol Inc Intermediaires primaires destines a des colorations capillaires d'oxydation
FR2830188B1 (fr) * 2001-09-28 2005-01-28 Oreal Composition tinctoriale contenant un compose para-aminophenol ou para-phenylene diamine substitue par un radical silanique
US20030217418A1 (en) * 2002-05-24 2003-11-27 Addi Fadel Hair dye composition and method for producing same

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1063979A (en) * 1965-09-23 1967-04-05 Gillette Industries Ltd Dyeing of hair and other keratinous materials and diaminobenzene compounds therefor
FR2430932A1 (fr) * 1978-07-12 1980-02-08 Oreal Metaphenylenediamines et compositions tinctoriales les contenant
DE3543345A1 (de) 1985-12-07 1987-06-11 Wella Ag Oxidationshaarfaerbemittel auf der basis von 4-amino-2-aminomethyl-phenolen
DE3610396A1 (de) 1986-03-27 1987-10-01 Wella Ag Mittel und verfahren zur oxidativen faerbung von haaren
US5279620A (en) * 1988-09-12 1994-01-18 L'oreal Tinctorial compositions for keratin fibres containing precursors of oxidation colorants and indole couplers, and dyeing processes using these compositions
FR2659228B1 (fr) * 1990-03-08 1994-10-14 Oreal Procede de teinture des fibres keratiniques avec des 6 ou 7-monohydroxy-indoles a ph acide et compositions mises en óoeuvre.
US5540738A (en) * 1991-11-26 1996-07-30 Chan; Alexander C. Oxidative hair coloring composition and process for dyeing human keratinous fibers
FR2707487B1 (fr) * 1993-07-13 1995-09-08 Oreal Composition de teinture d'oxydation des fibres kératiniques comprenant un para-aminophénol, un méta-aminophénol et une métaphénylènediamine, et procédé de teinture utilisant une telle composition.
DE4409143A1 (de) * 1994-03-17 1995-09-21 Henkel Kgaa Isatinderivate zum Färben von keratinhaltigen Fasern
FR2735685B1 (fr) * 1995-06-21 1997-08-01 Oreal Compositions pour la teinture des fibres keratiniques comprenant un ortho-diamino pyrazole et un sel de manganese procede de teinture mettant en oeuvre ces compositions
DE19545837A1 (de) * 1995-12-08 1997-06-12 Wella Ag Oxidationshaarfärbemittel

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9817235A1 *

Also Published As

Publication number Publication date
JP2000502368A (ja) 2000-02-29
US6224856B1 (en) 2001-05-01
BR9706882A (pt) 2000-01-25
DE19643060A1 (de) 1998-04-23
WO1998017235A1 (fr) 1998-04-30

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