WO1995007068A1 - Colorants d'oxydation contenant, comme substances copulantes, des derives de 2-hydroxy-4-amino-benzene et, comme substances developpeuses, des dihydroxydiaminopyrimidines - Google Patents

Colorants d'oxydation contenant, comme substances copulantes, des derives de 2-hydroxy-4-amino-benzene et, comme substances developpeuses, des dihydroxydiaminopyrimidines Download PDF

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Publication number
WO1995007068A1
WO1995007068A1 PCT/EP1994/002929 EP9402929W WO9507068A1 WO 1995007068 A1 WO1995007068 A1 WO 1995007068A1 EP 9402929 W EP9402929 W EP 9402929W WO 9507068 A1 WO9507068 A1 WO 9507068A1
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WO
WIPO (PCT)
Prior art keywords
hydroxy
dihydroxy
diaminopyrimidine
triaminopyrimidine
hair
Prior art date
Application number
PCT/EP1994/002929
Other languages
German (de)
English (en)
Inventor
David Rose
Edgar Lieske
Horst Höffkes
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
Publication of WO1995007068A1 publication Critical patent/WO1995007068A1/fr

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Classifications

    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • 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
    • 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

Definitions

  • OXIDATION PAINT CONTAINING 2-HYDR0XY-4-AMIN0-BENZ0L DERIVATIVES AS COUPLING SUBSTANCES AND HYDROXYTRIAMINOPYRIMIDINE OR DIHYDROXYDIAMINO-PYRIMIDINE AS DEVELOPING SUBSTANCES.
  • compositions for dyeing keratin-containing fibers, in particular human hair which contain a specially substituted aminophenol as developer component and a hydroxytriaminopyrimidine and / or dihydroxydiaminopyrirnidine as coupler component.
  • oxidation hair colorants play a preferred role for dyeing hair because of their intense colors and good fastness properties.
  • hair dyes contain oxidation dye precursors in a cosmetic carrier.
  • Developer substances and coupler substances are used as oxidation dye precursors.
  • the 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 have the desired color shades in sufficient intensity and fastness in the oxidative coupling form. They must also have a good ability to draw on human hair, with no noticeable differences between damaged and freshly regrown hair. They should be resistant to light, heat and the influence of chemical reducing agents, e.g. B. against perm fluids. After all, they should not stain the scalp too much, and above all they should be harmless from a toxicological and dermatological point of view.
  • a certain developer substance can form very different shades of color when combined with different couplers. Nevertheless, it is often not possible to achieve the multitude of natural hair color shades with the help of a single developer substance. In practice, therefore, a combination of different developer components and coupler components is usually required in order to obtain a single, natural-looking hair color. There is therefore a constant need for new, improved coupler / developer combinations.
  • Primary aromatic amines with a further free or substituted hydroxy or amino group in para or ortho position, tetraaminopyrimidines, hydroxytriaminopyrimidines, dihydroxydiaminopyrimidines, diaminopyridine derivatives, heterocyclic hydrazone derivatives or 4-aminopyrazolone derivatives are usually used as developer components.
  • M-Phenylenediamine derivatives, m-aminophenol derivatives, naphthols, resorcinol derivatives and pyrazolones are used as so-called coupler components.
  • German patent application DE 34 21 694 AI describes hair colorants which contain substituted 3,4-dihydroxyilines as coupler components.
  • German published patent application DE 31 45 811 A1 discloses hair dye compositions which also contain substituted 3,4-dihydroxyanilines, for example 1- (2'-hydroxyethoxy) -2-hydroxy-4-aminobenzene, in combination with tetraaminopyrimidine as the developer component.
  • coupler components as disclosed in DE 31 45 811 AI can be combined in an ideal manner with hydroxytriaminopyrimidines and dihydroxydiaminopyrimidines and thus provide oxidation hair colorants which have the properties disclosed in DE 31 45 811 AI in terms of dyeing-relevant properties, e.g. Wash fastness, light fastness, rubbing fastness, color winding, leveling behavior are superior.
  • the invention relates to compositions for dyeing keratin-containing fibers
  • R * and R ⁇ independently of one another are hydrogen, C1-C4-alkyl or C2 ⁇ C4-hydroxyalkyl groups,
  • At least one developer component selected from the group 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 5-hydroxy-2,4,6-triaminopyrimidine, 2,4-dihydroxy -5,6-di-aminopyrimidine, 2,5-dihydroxy-4,6-diaminopyrimidine, 4,5-dihy- droxy-2,6-diaminopyrimidine and 4,6-dihydroxy-2,5-diaminopyrimidine,
  • Keratin-containing fibers are hair, furs, wool or feathers.
  • the coupler and developer components can be used both as free bases and in the form of their inorganic or organic salts, e.g. the hydrochloride or hydrobromide.
  • Preferred colorants are those in which the developer component is selected from 4-hydroxy-2,5,6-triaminopyrimidine and 2,4-dihydroxy-5,6-diaminopyrimidine or in those in the coupler component of the formula IR * and R ⁇ represent hydrogens.
  • the colorants according to the invention provide a broad spectrum of oxidation colors which are of interest in terms of application technology, in the range from red to ruby shades, which are suitable for dyeing human hair, owing to their brilliance, good leveling ability and good fastness properties.
  • a further subject of the invention is therefore hair dyes
  • At least one coupler component of the formula I in an amount of 0.05 to 20 mmol, preferably 1 to 10 mmol,
  • At least one developer component selected from the group 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 5-hydroxy-2,4,6-triaminopyrimidine, 2,4-dihydroxy -5,6-di-aminopyrimidine, 2,5-dihydroxy-4,6-diaminopyrimidine, 4,5-dihy- droxy-2,6-diaminopyrimidine and 4,6-dihydroxy-2,5-diaminopyrimidine, in an amount of 0.05 to 20 mmol, preferably 1 to 10 mmol, in each case based on 100 g of the total hair dye,
  • the hair dye according to the invention can in addition to the above.
  • Developer components optionally other customary developer components e.g. from the group of primary aromatic amines with a further free or substituted hydroxy or amino group in the p or o position, diaminopyridine derivatives, tetraaminopyrimidine derivatives, heterocyclic hydrazone derivatives or 4-aminopyrazolone derivatives.
  • coupler components of formula I they can also contain other conventional coupler components, e.g. from the group of m-phenylenediamine derivatives, naphthols, resorcinols and pyrazolones.
  • direct dyes e.g. from the group of nitrophenylene diamines, nitroa inophenols, anthraquinones or indophenols.
  • 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 oxidation dye precursors are incorporated in 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 water-containing carrier usually contains wetting and emulsifying agents, such as anionic, nonionic or ampholytic surfactants, for example fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, alkyl glycosides, ethylene oxide addition products on fatty alcohols, on fatty acids, on sorbitan fatty acids, on alkylphenols, on Fatty acid partial glycerides and fatty acid alkanolamides; Thickeners, e.g. B.
  • anionic, nonionic or ampholytic surfactants for example fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, alkyl glycosides, ethylene oxide addition products on fatty alcohols, on fatty acids, on sorbitan fatty acids, on alky
  • fatty alcohols fatty acids, paraffin oils, fatty acid esters and other fat components in emulsified form
  • water-soluble polymeric thickeners such as natural gums, e.g. B. gum arabic, karaya gum, guar gum, locust bean gum, linseed gums and pectin, biosynthetic gums, for example xanthan gum i and dextrans, synthetic gums, e.g. B. agar-agar and algin, starch fractions and derivatives such as amylose, amylopectin and dextrins, modified cellulose molecules, eg. As methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, clays such as. B.
  • natural gums e.g. B. gum arabic, karaya gum, guar gum, locust bean gum, linseed gums and pectin
  • biosynthetic gums for example xanthan gum i
  • the constituents of the water-containing carrier are used for the production of the hair 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 color can in principle be carried out with atmospheric oxygen.
  • a chemical oxidizing agent is preferably used, especially when a lightening effect on the hair is desired in addition to the coloring.
  • Particularly suitable oxidizing agents are hydrogen peroxide or its adducts with urea, melamine or sodium borate and mixtures of such hydrogen peroxide adducts with potassium peroxide disulfate.
  • 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 be in a 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 color shesha poo was used.
  • Hair dyes according to the invention were produced in the form of a hair dye emulsion with the following composition:
  • 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 9.5 with concentrated ammonia solution, and the mixture was then made up to 100 g with water.
  • the oxidative development of the color was carried out with 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 strands approx. 5 cm long, 90% gray but not specially pretreated, and left there for 30 minutes at 27 ° C. After the dyeing process had ended, the hair was rinsed, washed with a conventional shampoo and then dried.

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  • 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 agents permettant de colorer des fibres contenant de la kératine, notamment des cheveux, qui contiennent, comme constituant développeur, un composé choisi dans le groupe 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 5-hydroxy-2,4,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5-dihydroxy-4,6-diaminopyrimidine, 4,5-dihydroxy-2,6-diaminopyrimidine, et 4,6-dihydroxy-2,5-diaminopyrimidine, et, comme constituants copulateurs, une 3,4-dihydroxyaniline substituée de manière spéciale.
PCT/EP1994/002929 1993-09-10 1994-09-02 Colorants d'oxydation contenant, comme substances copulantes, des derives de 2-hydroxy-4-amino-benzene et, comme substances developpeuses, des dihydroxydiaminopyrimidines WO1995007068A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4330711.6 1993-09-10
DE19934330711 DE4330711A1 (de) 1993-09-10 1993-09-10 Oxidationsfärbemittel

Publications (1)

Publication Number Publication Date
WO1995007068A1 true WO1995007068A1 (fr) 1995-03-16

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ID=6497371

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1994/002929 WO1995007068A1 (fr) 1993-09-10 1994-09-02 Colorants d'oxydation contenant, comme substances copulantes, des derives de 2-hydroxy-4-amino-benzene et, comme substances developpeuses, des dihydroxydiaminopyrimidines

Country Status (2)

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DE (1) DE4330711A1 (fr)
WO (1) WO1995007068A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004029797A1 (de) * 2004-06-19 2006-06-08 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2282858A1 (fr) * 1973-11-29 1976-03-26 Henkel & Cie Gmbh Teintures pour cheveux contenant des tetraaminopyrimidines
DE3145811A1 (de) * 1981-11-19 1983-05-26 Wella Ag, 6100 Darmstadt Neue 2-hydroxy-4-aminobenzole, verfahren zu deren herstellung und diese verbindungen enthaltende haarfaerbemittel
EP0467026A1 (fr) * 1990-07-17 1992-01-22 Goldwell Aktiengesellschaft Composition de teinture des cheveux et son application
WO1992019220A1 (fr) * 1991-05-08 1992-11-12 Henkel Kommanditgesellschaft Auf Aktien Agent de teinture pour les cheveux

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2282858A1 (fr) * 1973-11-29 1976-03-26 Henkel & Cie Gmbh Teintures pour cheveux contenant des tetraaminopyrimidines
DE3145811A1 (de) * 1981-11-19 1983-05-26 Wella Ag, 6100 Darmstadt Neue 2-hydroxy-4-aminobenzole, verfahren zu deren herstellung und diese verbindungen enthaltende haarfaerbemittel
EP0467026A1 (fr) * 1990-07-17 1992-01-22 Goldwell Aktiengesellschaft Composition de teinture des cheveux et son application
WO1992019220A1 (fr) * 1991-05-08 1992-11-12 Henkel Kommanditgesellschaft Auf Aktien Agent de teinture pour les cheveux

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Publication number Publication date
DE4330711A1 (de) 1995-03-16

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