EP0423181A1 - Produit pour teindre les cheveux - Google Patents

Produit pour teindre les cheveux

Info

Publication number
EP0423181A1
EP0423181A1 EP89907751A EP89907751A EP0423181A1 EP 0423181 A1 EP0423181 A1 EP 0423181A1 EP 89907751 A EP89907751 A EP 89907751A EP 89907751 A EP89907751 A EP 89907751A EP 0423181 A1 EP0423181 A1 EP 0423181A1
Authority
EP
European Patent Office
Prior art keywords
hair
oxidation
pct
hair dye
coupler
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.)
Pending
Application number
EP89907751A
Other languages
German (de)
English (en)
Inventor
David Rose
Horst Höffkes
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 EP0423181A1 publication Critical patent/EP0423181A1/fr
Pending legal-status Critical Current

Links

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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • 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

  • the invention relates to hair dyes based on oxidation dyes.
  • hair dyes contain oxidation dye precursors in a cosmetic carrier.
  • Developer substances and coupler substances which form dyes under the influence of oxidizing agents or atmospheric oxygen are used as oxidation dye precursors.
  • Creams, emulsions, gels, shampoos, foam aerosols or other preparations which are suitable for use on the hair serve as cosmetic carriers for the oxidation dye precursors.
  • oxidation colors which result from the oxidative coupling of one or more developer components with one another or with one or more coupler components, play a preferred role for dyeing hair because of their intense colors and good fastness properties.
  • Primary aromatic amines with a further free or substituted hydroxy or amino group in para or ortho position, furthermore diamino-pryidine derivatives, heterocyclic hydrazone derivatives, 4-aminopyrazo-ion derivatives and tetraaminopyrimidines are usually used as developer substances.
  • M-Phenylenediamine derivatives, naphthols, resorcinol derivatives and pyrazolones are used as so-called coupler substances.
  • oxidation hair dye precursors must first of all meet the following requirements: In oxidative coupling, they must have the desired color shades in sufficient intensity. did train. You must also have good absorption on human hair without staining the scalp too much. The color should also be applied evenly, ie the hair tips that are more heavily used should not be colored more than the little damaged hairline. The dyeings produced must have a high stability against heat, light and the chemicals used in the permanent waving of the hair. Finally, the oxidation hair dye precursors should be harmless from a toxicological and dermatological point of view.
  • 3-aminophenols are oxidation dye precursors such. B. from DE-AS 11 43 605, DE-AS 1 1 51 900, DE 24 47 017 C2 and DE 30 16 882 AI already known.
  • the hair colorants that can be produced with these products and known developer components are unsatisfactory in terms of the fastness properties. of the hair staining that can be achieved with it.
  • the known 3-amirophenols are obtained. no brown shades of satisfactory naturalness, brilliance and depth of color.
  • hair colorants containing oxidatron dye precursors in a carrier which as oxidation dye precursors are N-cycloalkyl 3-aminophenols of the formula (1)
  • n is an integer from 4 to 8 and R 1, R2 and R 3 independently of one another are hydrogen, methyl groups or chlorine, or their salts as coupler substances and those in oxidation hair colorants contain customary developer substances that meet the requirements to a high degree.
  • N-cycloalkyl-3-aminophenols of the formula I are used in which
  • R 1, R2 and R 3 are hydrogen and the group
  • Coupled component K2 and K3 is a cyclopentyl or cyclohexyl group optionally substituted by 1 or 2 methyl groups.
  • the compounds listed as examples (coupling components K2 and K3) are particularly preferred.
  • R is hydrogen
  • R is methyl groups or chlorine, can be analog
  • Suitable aminophenols are in addition to the 3-aminopheno! z.
  • B 5- chloro-3-aminophenol, 5-chloro-6-methyl-3-aminophenol, 4-chloro-3-aminophenol, 5-methyl-3-aminophenol, 6-methyl! -3-aminophenol, 2-methyl-6 -aminophenol and 2, 6-dimethyl-3-aminophenoI.
  • Suitable cycloalkanones are e.g. B.
  • N-cycloalkyl-3-amrnophenols of the formula I are valuable coupler compounds which, with a large number of customary developer components, form intense oxidation colors of high light, heat and cold wave fastness, predominantly in the range of brown and blue-violet shades.
  • developer substances are, for example, p-phenyldiamine, p-toluenediamine, N, N-diethy i-2-methy Ip-pheny len-d ⁇ am ⁇ n, N-ethyl-N-C2-hydroxylethyI) -p-phenyIendiam ⁇ n, chloro-p-phenylenediamine , N, N-bis- [2-hydroxylethyl) -p-phenylenediamine, N, N-dimethyl-p-phenylenediamine, methoxy-p-phenylenediamine, 2,6-dichloro-p-phenylenediamine, 2-chloro-6 -bromo-p-phenylene diamine, 2-chlorine -6-methy ip-phenylene diamine, 6-methoxy-3-methylene-p-phenylene diamine, 2, 5-D'aminoanisoI, N- (2-
  • P-Phenylenediamine, p-toluenediamine or derivatives of these compounds or their salts are preferably used as developer substances.
  • the N-cycloalkyl-3-aminophenols of the formula I to be used according to the invention and the p-phenylenediamine or p-toluenediamine derivatives suitable as developer components can either be used as such or in the form of their salts with inorganic or organic acids, for example can be used as chloride, sulfate, phosphate, acetate, propionate, lactate or citrate.
  • 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 color tones.
  • coupler connections are e.g. B. other m-phenylenediamines, e.g. B. 2, 4-diaminophenyl-2-hydroxyethyl ether, or phenols, resorcinols, m-aminophenols, naphthols or pyrazones.
  • substantive dyes can also be used to further modify the color shades.
  • Such substantive dyes are e.g. B. Nitrophenylenediamines, nitroaminophenols, anthraquinone dyes or indophenols.
  • N-cycloalkyl-3-aminophenoies of the formula (I) and the known coupler substances which may additionally be present are generally used in approximately molar amounts, based on the developer substances used, for the hair colorants according to the invention. 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.
  • N-cycloalkyl-3-aminophenols of the formula (I) and the oxidation dye precursors or dyes which are otherwise present in the hair dye compositions represent uniform chemical compounds. Rather, these can also be mixtures of the coupler or developer substances to be used according to the invention.
  • 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, meiamin or sodium borate and mixtures of such hydrogen peroxide adducts with potassium peroxide disulfate.
  • the oxidation dye precursors are incorporated into a suitable cosmetic carrier.
  • suitable cosmetic carrier are e.g. B. Creams, emulsions, gels or surfactant-containing, foaming solutions, e.g. B. Sha poos or other preparations which are suitable for use on the hair.
  • Common components of such cosmetic preparations are e.g. B. Wetting and emulsifying agents such as anionic, nonionic or ampholytic surfactants, e.g. B.
  • fatty alcohol sulfates alkane sulfonates, alpha-olefin sulfonates, fatty alcohol polyglycol ether sulfates, ethylene oxide addition products with fatty alcohols, with fatty acids and with alkylphenols, sorbitan fatty acid esters and fatty acid partial glycerides, fatty acid alkanoiamides and thickeners such as, for. B. Methyl or hydroxyethyl cellulose. Starch, fat components such as B. Fatty alcohols. Paraffin oils or fatty acid esters also perfume and hair care additives such. B. water soluble cationic polymers, protein derivatives, pantothenic acid and cholesterol.
  • the constituents of the cosmetic carriers are used for the production of the hair colorants according to the invention in amounts customary for these purposes, e.g. B. are emulsifiers concentrated trations of 0.5-30% by weight and thickeners in concentrations of 0.1-25% by weight of the total colorant.
  • An oil-in-water emulsion with a content of 0.1-25% by weight of a fat component and 0.5-30% by weight of an emulsifier from the group of anionic, nonionic or ampholytic surfactants is particularly suitable as a carrier .
  • 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 content of N-cycioalkyl-3-aminophenols of the formula (I) in the hair colorants according to the invention can be about 0.05-10 millimoles per 100 g of the hair colorant.
  • the use of the hair dye according to the invention can, regardless of the type of cosmetic preparation, for. B. as a cream, gel or shampoo, preferably in a weakly alkaline environment.
  • the hair colorants are preferably used in a pH range of 6-10.
  • the application temperatures can be in a range between 15 ° C. and 40 ° C.
  • the hair dye is rinsed off the hair to be dyed.
  • the hair is then washed with a mild shampoo and dried. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. B. a coloring shampoo was used.
  • Hair colorants according to the invention were produced in the form of a hair coloring cream emulsion of the following composition:
  • the ingredients were mixed together in order. After addition of the oxidation coloring agent precursors and the inhibitor, 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 was mixed with 50 g of hydrogen peroxide solution (3%) and mixed.
  • the coloring cream was standardized on approx. 5 cm long strands, 90% gray, but not specially pretreated human hair and left there at 27 ° C. for 30 minutes. After the dyeing process was completed, the hair was rinsed, washed out with a customary shampoo and then dried.
  • the following N-cyanoalkyI-3-aminophenols were used as the coupler component (component K):

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

Produits pour teindre les cheveux contenant, en tant qu'ingrédients de colorant d'oxydation du type copulateur, des N-cycloalkyl-3-aminophénols correspondant à la formule (I), où n est un nombre entier compris entre 4 et 8, et R1, R2 et R3 représentent, indépendamment les uns des autres, hydrogène, des groupes méthyle ou chlore, ou leurs sels, outre les substances habituelles de développement dans un support. Ces nouvelles compositions d'accouplement produisent, avec les substances de développement habituelles, par exemple du type des dérivés de p-phénylène-diamine, des teintes brunes très solides.
EP89907751A 1988-07-01 1989-06-23 Produit pour teindre les cheveux Pending EP0423181A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3822365 1988-07-01
DE3822365A DE3822365A1 (de) 1988-07-01 1988-07-01 Haarfaerbemittel

Publications (1)

Publication Number Publication Date
EP0423181A1 true EP0423181A1 (fr) 1991-04-24

Family

ID=6357790

Family Applications (2)

Application Number Title Priority Date Filing Date
EP89907751A Pending EP0423181A1 (fr) 1988-07-01 1989-06-23 Produit pour teindre les cheveux
EP89111507A Expired - Lifetime EP0348849B1 (fr) 1988-07-01 1989-06-23 Composition de coloration des cheveux

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP89111507A Expired - Lifetime EP0348849B1 (fr) 1988-07-01 1989-06-23 Composition de coloration des cheveux

Country Status (9)

Country Link
US (1) US5104412A (fr)
EP (2) EP0423181A1 (fr)
JP (1) JPH03505460A (fr)
KR (1) KR900701245A (fr)
AT (1) ATE81448T1 (fr)
DE (2) DE3822365A1 (fr)
DK (1) DK302390D0 (fr)
ES (1) ES2052823T3 (fr)
WO (1) WO1990000046A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5430930A (en) * 1993-10-12 1995-07-11 Italimpianti Of America, Inc. Method of manufacturing hot strip
JPH11228364A (ja) * 1997-11-19 1999-08-24 Bristol Myers Squibb Co 染毛組成物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2447017C2 (de) * 1974-10-02 1987-05-07 Henkel Kgaa, 4000 Duesseldorf Haarfärbemittel
JPS61100551A (ja) * 1984-10-23 1986-05-19 Kanzaki Paper Mfg Co Ltd シクロアルキルアミノフエノ−ル誘導体の製造法
DE3524329A1 (de) * 1985-07-08 1987-01-08 Henkel Kgaa Neue aminophenole und deren verwendung in oxidationshaarfaerbemitteln

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9000046A1 *

Also Published As

Publication number Publication date
EP0348849A1 (fr) 1990-01-03
DK302390A (da) 1990-12-20
WO1990000046A1 (fr) 1990-01-11
JPH03505460A (ja) 1991-11-28
US5104412A (en) 1992-04-14
ES2052823T3 (es) 1994-07-16
DE3822365A1 (de) 1990-01-04
EP0348849B1 (fr) 1992-10-14
DK302390D0 (da) 1990-12-20
ATE81448T1 (de) 1992-10-15
DE58902449D1 (de) 1992-11-19
KR900701245A (ko) 1990-12-01

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