Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2001-08-15
2003-01-07
Gupta, Yogendra N. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S401000, C008S405000, C008S406000, C008S408000, C564S099000, C564S443000
Reexamination Certificate
active
06503282
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention concerns a composition for coloring keratin fibers, particularly human hair, said composition containing 3-(2,4-diaminophenoxy)-1-propanol and at least one p-phenylenediamine derivative, 4,5-diamino-1H-pyrazole derivative or p-aminophenol derivative, and a method for coloring keratin fibers.
Oxidation dyes have attained essential importance in the field of hair coloring. The color is created by reaction of certain developers with certain couplers in the presence of an oxidant.
Oxidation dyes intended to be used for coloring human hair must meet numerous special requirements. Said dyes must be toxicologically and dermatologically harmless and non-sensitizing and they must produce colors of the desired intensity.
The hair colors must remain stable for at least four to six weeks. It is also expected that the hair colorations will remain stable when other cosmetic treatments are applied, such as shampooing or hair restyling. The hair colors should also be resistant to external effects such as light and weather as well as to perspiration and mechanical abrasion.
It is also necessary to be able to create a wide range of different color shades by combining appropriate developers and couplers.
The preparation of stable blue and reddish color shades presents a particular problem. Blue-coloring hair dye couplers together with yellow and red color components are needed for producing natural-looking hair colorations. Fashionable reddish hair colors, on the other hand, are created by use of an excess of the red color component.
The stability of the hair colors in both the blue and the red range, however, still leaves much to be desired, particularly as regards the action of organic acids and perspiration.
SUMMARY OF THE INVENTION
Surprisingly, we have now found that with a combination consisting of the coupler 3-(2,4-diamino-phenoxy)-1-propanol and at least one developer selected from the group consisting of certain p-phenylenediamine derivatives, 4,5-diamino-1H-pyrazole derivatives and p-aminophenol derivatives, it is possible to prepare hair colorants which, compared to the prior art, present substantially improved resistance to organic acids and perspiration besides outstanding washing and light fastness.
The preparation of 3-(2,4-diaminophenoxy)-1-propanol dihydrochloride and the use thereof in hair colorants are known from U.S. Pat. Nos. 4,259,261 and 4,329,504.
The object of the present invention is a composition for coloring keratin fibers, particularly human hair, based on a developer-coupler combination, characterized in that it contains as the coupler 3-(2,4-diaminophenoxy)-1-propanol and as the developer
a p-phenylenediamine derivative monosubstituted on the benzene ring and having general formula (I)
wherein m equals 0 or 1 and R
1
is a straight-chain or branched C
3
-C
6
-alkyl group, a straight-chain or branched monohydroxy-(C
1
-C
6
)-alkyl group or a polyhydroxy-(C
2
-C
6
)-alkyl group, a straight-chain or branched mono-(C
2
-C
6
)-alkoxy-(C
2
-C
6
)-alkyl group or poly-(C
2
-C
6
)-alkoxy-(C
2
-C
6
)-alkyl group or a carbocyclic or heterocyclic, substituted or unsubstituted aromatic compound; and/or
a 4,5-diamino-1H-pyrazole derivative of general formula (II)
wherein R
2
, R
4
and R
6
independently of each other denote a hydrogen atom or a straight-chain or branched C
2
-C
6
-alkyl group, a straight-chain or branched monohydroxy-(C
1
-C
6
)-alkyl group or a polyhydroxy-(C
2
-C
6
)-alkyl group or an unsubstituted benzyl group or a benzyl group substituted on the benzene ring, and R
3
denotes a straight-chain or branched C
1
-C
6
-alkyl group, a straight-chain or branched monohydroxy-(C
1
-C
6
)-alkyl group or polyhydroxy-(C
2
-C
6
)-alkyl group, a straight-chain or branched mono-(C
2
-C
6
)-alkoxy-(C
2
-C
6
)-alkyl group or poly-(C
2
-C
6
)-alkoxy-(C
2
-C
6
)-alkyl group, or a carbocyclic or heterocyclic, substituted or unsubstituted aromatic compound; and/or
a p-aminophenol derivative of general formula (III)
wherein R
6
is a straight-chain or branched C
1
-C
6
-alkyl group, a straight-chain or branched monohydroxy-(C
1
-C
6
)-alkyl group or polyhydroxy-(C
2
-C
6
)-alkyl group, a straight-chain or branched mono-(C
2
-C
6
)-alkoxy-(C
2
-C
6
)-alkyl group or poly-(C
2
-C
6
)-alkoxy-(C
2
-C
6
)-alkyl group, a straight-chain or branched amino-(C
2
-C
6
)-alkyl group or a carbocyclic or heterocyclic, substituted or unsubstituted aromatic compound.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Preferred p-phenylenediamine derivatives of formula (I) are 2-propyl-p-phenylenediamine, 2-(hydroxymethyl)-p-phenylenediamine, 2-(1-hydroxyethyl)-p-phenylenediamine, 2-(2-hydroxyethyl)-p-phenylenediamine, 2-(3-hydroxypropyl)-p-phenylenediamine, 2-(1,2-dihydroxyethyl)-p-phenylenediamine, 2-(methoxymethyl)-p-phenylenediamine, 2-(2-methoxyethyl)-p-phenylenediamine, 2-(2-hydroxyethoxy)-p-phenylenediamine, 2,5-diaminobiphenyl, 2-(2-thienyl)-p-phenylenediamine, 2-(3-thienyl)-p-phenylenediamine and 3-(2,5-diaminophenyl)pyridine.
Preferred pyrazole derivatives of formula (II) are 4,5-diamino-1-methyl-1H-pyrazole, 4,5-diamino-1-(2-hydroxyethyl)-1H-pyrazole, 4,5-diamino-1-(1-methylethyl)-1H-pyrazole, 4,5-diamino-1-(phenylmethyl)-1H-pyrazole, 4,5-diamino-1-[(4-methylphenyl)methyl]-1H-pyrazole, 4,5-diamino-1-(2-hydroxyethyl)-3-methyl-1H-pyrazole and 4,5-diamino-1-methyl-3-phenyl-1H-pyrazole.
Preferred p-aminophenol derivatives of formula (III) are 3-methyl-p-aminophenol, 2-aminomethyl-p-aminophenol, 2-hydroxymethyl-p-aminophenol, 3-hydroxymethyl-p-aminophenol, 2-phenyl-p-aminophenol, 2-(2-thienyl)-p-aminophenol, 2-(3-thienyl)-p-aminophenol, 3-(2-thienyl)-p-aminophenol and 3-(3-thienyl)-p-aminophenol.
To complete the coloring treatment and to create special color effects, other developers and/or couplers as well as direct dyes can be added to the combinations of the invention.
Suitable developers are, for example, the following compounds: 1,4-diaminobenzene, 1,4-diamino-2-methylbenzene, 1,4-diamino-2,6-dimethylbenzene, 2,5-diamino-1,3-diethylbenzene, 1,4-diamino-2,5-dimethylbenzene, 1,4-diamino-2,3-dimethylbenzene, 2-chloro-1,4-diaminobenzene, 1-(aminomethyl)-2,5-diaminobenzene, 2-[2-(acetylamino)ethoxy]-1,4-diaminobenzene, 4-phenylaminoaniline, 4-dimethylaminoaniline, 4-(dipropylamino)aniline, 4-diethylaminoaniline, 4-[ethyl(2-hydroxyethyl)amino]aniline, 4-[di(2-hydroxyethyl)amino]aniline, 4-[di(2-hydroxyethyl)amino]-2-methylaniline, 4-[(2-methoxyethyl)amino]aniline, 4-[(3-hydroxypropyl)amino]aniline, 4-[(2,3-dihydroxypropyl)amino]aniline, 1,3-bis-[(4-aminophenyl)(2-hydroxyethyl)amino]-2-propanol, 1,4-di[(4-aminophenyl)amino]butane, 1,8-bis-(2,5-diaminophenoxy)-3,6-dioxaoctane, 4-aminophenol, 4-amino-3-fluorophenol, 4-methylaminophenol, 4-amino-2-(aminomethyl)phenol, 4-amino-2-(hydroxymethyl)phenol, 4-amino-2-fluorophenol, 4-amino-2-[(2-hydroxyethyl)amino]methylphenol, 4-amino-2-methylphenol, 4-amino-2-(methoxymethyl)phenol, 4-amino-2-(2-hydroxyethyl)phenol, 5-aminosalicylic acid, 2,5-diaminopyridine, 2,4,5,6-tetraaminopyrimidine and 2,5,6-triamino-4(1H)-pyrimidone.
Suitable couplers are, for example, the following compounds: 2,6-diaminopyridine, 2-amino-4-[(2-hydroxyethyl)amino]anisole, 2,4-diamino-1-fluoro-5-methylbenzene, 2,4-diamino-1-methoxy-5-methylbenzene, 2,4-diamino-1-ethoxy-5-methylbenzene, 2,4-diamino-1-(2-hydroxyethoxy) -5-methylbenzene, 2,4-di[(2-hydroxyethyl)amino]-1,5-dimethoxybenzene, 2,3-diamino-6-methoxypyridine, 3-amino-6-methoxy-2-(methylamino)pyridine, 2,6-diamino-3,5-dimethoxypyridine, 3,5-diamino-2,6-dimethoxypyridine, 1,3-diaminobenzene, 2,4-diamino-1-(2-hydroxyethoxy)benzene, 2,4-diamino-1,5-di(2-hydroxyethoxy)benzene, 1-(2-aminoethoxy)-2,4-diaminobenzene, 2-amino-(2-hydroxyethoxy)-4-methylaminobenzene, 2,4-diaminophenoxyacetic acid, 3-[di(2-hydroxyethyl)amino]aniline, 4-amino-2-di[(2-hydroxyethyl)amino]-1-ethoxybenzene, 5-methyl-2-(1-methylethyl)phenol, 3-&ls
Elhilo Eisa
Gupta Yogendra N.
Striker Michael J.
Wella Aktiengesellschaft
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