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WO1993000883A1 - Utilisation de 1,9-dihydro-pyrazolo [4,3-b] [1,4]-benzoxazines comme copulants pour colorants d'oxydation - Google Patents

Utilisation de 1,9-dihydro-pyrazolo [4,3-b] [1,4]-benzoxazines comme copulants pour colorants d'oxydation Download PDF

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Publication number
WO1993000883A1
WO1993000883A1 PCT/EP1992/001424 EP9201424W WO9300883A1 WO 1993000883 A1 WO1993000883 A1 WO 1993000883A1 EP 9201424 W EP9201424 W EP 9201424W WO 9300883 A1 WO9300883 A1 WO 9300883A1
Authority
WO
WIPO (PCT)
Prior art keywords
oxidation
formula
hydrogen
dihydro
benzoxazines
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.)
Ceased
Application number
PCT/EP1992/001424
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German (de)
English (en)
Inventor
David Rose
Edgar Lieske
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 WO1993000883A1 publication Critical patent/WO1993000883A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds

Definitions

  • the invention relates to the use of 1,9-dihydropyrazolo [4,3-b] [1,4] benzoxazines as oxidation dye precursors of the coupler type in oxidation colorants containing conventional developer compounds for coloring keratin fibers, in particular human hair.
  • Oxidation paints are produced by oxidatively coupling one or more developer components (or oxidation bases) with one another or with one or more coupler components (color modifier).
  • these oxidation dye precursors are incorporated into a cosmetic carrier suitable for use on the hair, which enables the dyes to be easily applied and distributed on the hair.
  • Such carriers are e.g. B. creams, emulsions, gels, shampoos, aerosols or other, preferably aqueous preparations.
  • Primary aromatic amines with a further hydroxyl or amino group in para or ortho position are usually used as developer substances, which form ortho and parachinoid structures under the influence of an oxidizing agent can react further to dye molecules.
  • Other compounds suitable as developers or oxidation bases are e.g. B. Diaminopyrid ⁇ ne, heterocyclic hydrazones, 4-aminopyrazolones, 2,4,5,6-tetraaminopyrimidines and 6-hydroxy-2,4,5-triaminopyrimidines.
  • the dyes available through this oxidative self-coupling are mostly unsatisfactory.
  • oxidation hair dye precursors must first of all meet the following requirements: they must develop the desired color shades with sufficient intensity in the oxidative coupling. They also need to be easy to draw on human hair without staining the scalp too much. The color winding should also be uniform, i. H. the more heavily used hair tips should not be colored more than the little damaged hairline. The dyeings produced in this way must have a high stability against heat, light and chemicals used in permanent waving. After all, the oxidation hair dye precursors should be harmless from a toxicological and dermatological point of view.
  • 1,9-Dihydro-pyrazolo [4,3-b] [1,4] -benzoxazines are known from EP-A 85 881 as lipoxygenase inhibitors.
  • the invention relates to the use of 1,9-dihydro-pyrazolo [4,3-b] [1,4] benzoxazines of the formula I.
  • R 1 , R 2 and R 3 are independently hydrogen, halogen or alkyl groups with 1 to 4 carbon atoms and R 4 are hydrogen, alkyl groups with 1 to 4 carbon atoms or hydroxyalkyl groups with 2 to 4 carbon atoms or the like Salts as coupler components in oxidation colorants containing conventional developer compounds for coloring keratin fibers, especially human hair.
  • the 1,9-dihydro-pyrazolo [4,3-b] [1,4] benzoxazines suitable according to the invention can be prepared from known precursors by the process described in EP-A 85881.
  • the preparation of compounds of the formula I which are not known from the literature is described in the preparation examples C1 and K2.
  • the new coupler components are suitable for color modification for all known oxidation vases (developer compounds). Some particularly suitable developer components are listed in Example 2 (application example) as E1 to E17.
  • hair colorants containing oxidation dye precursors in a cosmetic carrier are hair colorants containing oxidation dye precursors in a cosmetic carrier, the 1,9-dihydropyrazolo [4,3-b] [1,4] benzoxazines of the formula I according to Claim 1 or their salts as couplers in an amount of Remove 0.05 - 10 millimoles per 100 g of the hair dye as well as the usual developer components and, if necessary, the usual coupler components.
  • the 1,9-dihydropyrazolo [4,3-b] [1,4] -benzoxazines of the formula I are preferably in free form, but optionally also in the form of their salts, e.g. B. as hydrochlorides, sulfates, phosphates, acetates, propionates, lactates or citrates.
  • the hair colorants according to the invention can also contain other known coupler substances which are required for modifying the color nuances and for producing natural shades. Such usual coupler connections are e.g. B.
  • m-phenylenediamines for example 2,4-diaminophenyl-2-hydroxyethyl ether, or phenols, resorcinols, m-aminophenols, naphthols or pyrazolones.
  • developer components oxidation bases
  • substantive dyes can be used to further modify the color shades.
  • direct dyes are e.g. B. nitrophenylenediamines, nitroaminophenols, anthraquinone dyes 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 substances and coupler substances can be present in a molar ratio of 1: 0.5 to 1: 2.
  • the oxidation dye precursors are incorporated into a suitable cosmetic carrier.
  • suitable cosmetic carriers are e.g. B. creams, emulsions, gels or surfactant-containing, foaming solutions, eg. B. shampoos, aerosols or other preparations that are suitable for use on the hair.
  • - Wetting and emulsifying agents such as anionic, nonionic or ampholytic surfactants, e.g. B. fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, Ethylene oxide adducts on fatty alcohols, on fatty acids, on alkylphenols, on sorbitan fatty acid esters, on fatty acid partial glycerides and on fatty acid alkanolamides,
  • anionic, nonionic or ampholytic surfactants e.g. B. fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, Ethylene oxide adducts on fatty alcohols, on fatty acids, on alkylphenols, on sorbitan fatty acid esters, on
  • Thickeners such as B. fatty alcohols, fatty acids, paraffin oils, fatty acid esters and other fat components in emulsified form,
  • Water-soluble, polymeric thickeners such as. B. methyl or hydroxyethyl cellulose, starch, vegetable gums, water-soluble synthetic polymers, water-soluble biopolymers (e.g. xanthan gum),
  • - Hair care additives such as. B. water-soluble, cationic polymers, protein derivatives, pantothenic acid, vitamins, plant extracts, cholesterol and sugar,
  • - Reducing agent to stabilize the dye e.g. As sodium sulfite or ascorbic acid.
  • the constituents of the cosmetic carriers are used to produce the hair colorants according to the invention in amounts customary for this purpose; z.
  • 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.
  • a cream emulsion (oil-in-water emulsion) with a content of 1-25% by weight of an emulsified is particularly suitable as a carrier Fat component and 0.5 to 30% by weight of an emulsifier from the group of anionic, nonionic, ampholytic or zwitterionic surfactants or a gel with a content of 1 to 20% by weight of a soap, preferably ammonium oleate.
  • the oxidation dye precursors are mixed into the carrier in amounts of 0.2-5% by weight, preferably 1-3% 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 the hair is desired.
  • 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 of oxidation dye precursors and carrier immediately before hair coloring.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range of 6-10. 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, e.g. B. a coloring shampoo was used.
  • the following examples are intended to explain the subject of the invention in more detail, but without restricting it thereto.
  • the compound was obtained analogously to Kl starting from 2-hydroxy-4-methylaniline. 7-methyl-4Hbenz (1,4) oxazin-3-one (beige leaflet, melting point 197-198 ° C.) was isolated as an intermediate. The coupler was obtained in the form of light brown crystals with a melting point of 200-221 ° C. (with decomposition).
  • Hair colorants according to the invention were produced in the form of a hair color cream emulsion of the following composition:
  • Coupler component (component K) 7.5 mmol
  • 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 oxidizing agent.
  • 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 out with a customary 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

Des 1,9-dihydro-pyrazolo [4,3-b] [1,4]-benzoxazines de formule (I) conviennent comme copulants dans des colorants d'oxydation à base de composés développeurs connus, par exemple d'amines aromatiques ayant un autre groupe hydroxy ou amino se trouvant en position para ou ortho, pour l'obtention de teintures d'oxydation brillantes dans la zone des nuances rouge, jaune et bleue. De préférence, des composés de formule (I) dans laquelle R1, R2 et R3 sont un hydrogène, un chlore ou des groupes méthyle, et R4 est un hydrogène, un groupe méthyle ou un groupe hydroxyéthyle, sont utilisés dans des colorants d'oxydation pour teintures pour cheveux.
PCT/EP1992/001424 1991-07-03 1992-06-24 Utilisation de 1,9-dihydro-pyrazolo [4,3-b] [1,4]-benzoxazines comme copulants pour colorants d'oxydation Ceased WO1993000883A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4122035.8 1991-07-03
DE19914122035 DE4122035A1 (de) 1991-07-03 1991-07-03 Die verwendung von 1,9-dihydro-pyrazolo(4,3-b) (1,4)-benzoxazinen als kuppler fuer oxidationsfaerbemittel

Publications (1)

Publication Number Publication Date
WO1993000883A1 true WO1993000883A1 (fr) 1993-01-21

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/001424 Ceased WO1993000883A1 (fr) 1991-07-03 1992-06-24 Utilisation de 1,9-dihydro-pyrazolo [4,3-b] [1,4]-benzoxazines comme copulants pour colorants d'oxydation

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DE (1) DE4122035A1 (fr)
WO (1) WO1993000883A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19717222A1 (de) * 1997-04-24 1998-10-29 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0085881A2 (fr) * 1982-02-06 1983-08-17 Bayer Ag Pyrazolooxazines, -thiazines et -quinoléines, procédé pour leur préparation et leur utilisation comme médicament
WO1991007394A1 (fr) * 1989-11-22 1991-05-30 Bristol-Myers Squibb Company Teintures au benzoxazine

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0085881A2 (fr) * 1982-02-06 1983-08-17 Bayer Ag Pyrazolooxazines, -thiazines et -quinoléines, procédé pour leur préparation et leur utilisation comme médicament
WO1991007394A1 (fr) * 1989-11-22 1991-05-30 Bristol-Myers Squibb Company Teintures au benzoxazine

Also Published As

Publication number Publication date
DE4122035A1 (de) 1993-01-07

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