2-hydroxy-5-amino-biphenyl-derivatives and oxidative hair...

Details 2-hydroxy-5-amino-biphenyl-derivatives and oxidative hair... 2-hydroxy-5-amino-biphenyl-derivatives and oxidative hair...

2002-01-30

2004-06-15

Mruk, Brian P. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S406000, C008S421000, C564S305000, C564S306000, C564S307000, C564S308000

Reexamination Certificate

active

06749644

ABSTRACT:

The present invention relates to unsymmetrical 2-hydroxy-5-aminobiphenyl derivatives and to colorants for oxidative dyeing of keratin fibers, particularly human hair, based on a developer/coupler combination containing a 2-hydroxy-5-aminobiphenyl derivative as the developer.
In the area of keratin fiber dyeing, particularly hair dyeing, oxidation dyes have attained substantial importance. In this case, the coloration is produced by reaction of certain developers with certain couplers in the presence of an appropriate oxidant. Suitable developers are, in particular, p-phenylenediamines and p-aminophenol, and suitable couplers are, for example, resorcinols, 1-naphthol, 3-aminophenols and m-phenylenediamine.
The oxidation dyes used for dyeing human hair must meet numerous requirements in addition to that of being able to produce colorations of the desired intensity. For example, these dyes must be harmless from a toxicological and dermatological standpoint, and the obtained hair colorations must have good light fastness, resistance to permanent waving, acid fastness and rubbing fastness. In any case, however, such colorations must remain stable over a period of at least 4 to 6 weeks in the absence of exposure to light, rubbing and chemical agents. Moreover, by combination of appropriate developers and couplers, it must be possible to create a wide range of different color shades.
The use of certain symmetrical diaminodihydroxydiphenyls in oxidative hair colorants is known from German Unexamined Patent Application [DE-OS] 25 18 393. These colorants, however, produce only olive-brown to green-gray colorations. Hence, a need continued to exist for novel developers capable of producing a broader range of color shades.
We have now found that blond to red shades can be obtained by coupling a 2-hydroxy-5-aminobiphenyl derivative of general formula (I) with a common coupler.
Hence, the object of the present invention is a colorant for oxidative dyeing of keratin fibers, for example wool, furs, feathers or hair, particularly human hair, based on a developer-coupler combination containing as the developer a 2-hydroxy-5-aminobiphenyl derivative of general formula (I) or a physiologically tolerated water-soluble salt thereof
wherein
R1 denotes hydrogen, a halogen atom, C
1
-C
4
-alkyl group a C
1
-C
4
-hydroxyalkyl group, C
1
-C
4
-alkoxy group or a C
1
-C
4
-hydroxyalkoxy group;
R2, R3, R4, R5, R6 can be equal or different and independently of each other denote hydrogen, a halogen atom, a cyano group, a hydroxyl group, a C
1
-C
4
-alkoxy group, a C
1
-C
4
-hydroxyalkoxy group, a C
1
-C
6
-alkyl group, a C
1
-C
4
-alkyl thioether group, a mercapto group, a nitro group, an amino group (NH
2
), an alkylamino group, a dialkylamino group, a trifluoromethyl group, a —C(O)H group, a —C(O)CH
3
group, a —C(O)CF
3
group, an —Si(CH
3
)
3
group, a C
1
-C
4
-hydroxyalkyl group, a C
3
-C
4
-dihydroxyalkyl group, a —CH═CHR7 group, a —(CH
2
)
p
—CO
2
R8 group or a —(CH
2
)
p
R9 group, with p=1,2,3 or 4, a —C(R10)=NR11 group, or a C(R12)H—NR13R14 group, or two adjacent R2 to R6 groups form an —O—CH
2
—O— bridge;
R7 denotes hydrogen, a hydroxyl group, a nitro group, an amino group, a —CO
2
R12 group or a —C(O))CH
3
group;
R8, R10 and R13 can be equal or different and independently of each other denote hydrogen or a C
1
-C
4
-alkyl group;
R9 denotes an amino group or a nitrile group;
R11, R14 and R15 can be equal or different and independently of each other denote hydrogen, a hydroxyl group, a C
1
-C
4
-alkyl group, a C
1
-C
4
-hydroxyalkyl group, a C
3
-C
4
-dihydroxyalkyl group or a radical of formula
R12 denotes hydrogen, an amino group or a hydroxyl group, provided that the compound of formula (I) does not present a center of symmetry.
Suitable compounds of formula (I) are, for example:
2-hydroxy-3-chloro-5-aminobiphenyl; 2-hydroxy-3-methyl-5-aminobiphenyl; 2-hydroxy-4-chloro-5-aminobiphenyl; 2-hydroxy-4-methyl-5-aminobiphenyl; 2,2′-dihydroxy-5-aminobiphenyl; 2,3′-dihydroxy-5-aminobiphenyl; 2,4′-dihydroxy-5-aminobiphenyl; 2,5′-dihydroxy-5-aminobiphenyl; 2,6′-dihydroxy-5-aminobiphenyl; 2-hydroxy-5,2′-diaminobiphenyl; 2-hydroxy-5,3′-diaminobiphenyl; 2-hydroxy-5,4′-diaminobiphenyl; 2-hydroxy-5,5′-diaminobiphenyl; 2-hydroxy-5,6′-diaminobiphenyl; 2,2′,3′-trihydroxy-5-aminobiphenyl; 2,2′,4′-trihydroxy-5-aminobiphenyl; 2,2′,5′-trihydroxy-5-aminobiphenyl; 2,2′,6′-trihydroxy-5-aminobiphenyl; 2,3′,4′-trihydroxy-5-aminobiphenyl; 2,3′,5′-trihydroxy-5-aminobiphenyl; 2-hydroxy-5,2′,3′-triaminobiphenyl; 2-hydroxy-5,2′,4′-triaminobiphenyl; 2-hydroxy-5,2′,5′-triaminobiphenyl; 2-hydroxy-5,2′,6′-triaminobiphenyl; 2-hydroxy-5,3′,4′-triaminobiphenyl; 2-hydroxy-5,3′,5′-triaminobiphenyl; 2-hydroxy-5,3′,4′-triaminobiphenyl; 2-hydroxy-5,3′,5′-triaminobiphenyl, 2,2′-dihydroxy-5,3′-diaminobiphenyl; 2,2′-dihydroxy-5,4′-diaminobiphenyl; 2,2′-dihydroxy-5,6′-diaminobiphenyl; 2,3′-dihydroxy-5,4′-diaminobiphenyl; 2,3′-dihydroxy-5,5′-diaminobiphenyl; 2,3′-dihydroxy-5,6′-diaminobiphenyl; 2-hydroxy-5-amino-2′-aminomethylbiphenyl; 2-hydroxy-5-amino-2′-chlorobiphenyl; 2-hydroxy-5-amino-2′-cyano biphenyl; 2-hydroxy-5-amino-2′-fluorobiphenyl; 2-hydroxy-5-2′-methoxybiphenyl; 2-hydroxy-5-amino-2′-methylbiphenyl; 2-hydroxy-5-amino-2′-methylsulfanylbiphenyl; 2-hydroxy-5-amino-2′-nitrobiphenyl; 2-hydroxy-5-amino-3′-aminomethylbiphenyl; 2-hydroxy-5-amino-3′-chlorobiphenyl; 2-hydroxy-5-amino-3′-cyanobiphenyl; 2-hydroxy-5-amino-3′-flurobiphenyl; 2-hydroxy-5-amino-3′-methoxybiphenyl; 2-hydroxy-5-amino-3′-methylbiphenyl; 2-hydroxy-5-amino-3′-methylsulfanylbiphenyl; 2-hydroxy-5-amino-3′-nitrobiphenyl; 2-hydroxy-5-amino-4′-aminomethylbiphenyl; 2-hydroxy-5-amino-4′-chlorobiphenyl; 2-hydroxy-5-amino-4′-cyanobiphenyl; 2-hydroxy-5-amino-4′-fluorobiphenyl; 2-hydroxy-5-amino-4′-methoxybiphenyl; 2-hydroxy-5-amino-4′-methylbiphenyl; 2-hydroxy-5-amino-4′-methylsulfanylbiphenyl; 2-hydroxy-5-amino-4′-nitrobiphenyl; 2-hydroxy-5-amino-5′-aminomethylbiphenyl; 2-hydroxy-5-amino-5′-chlorobiphenyl; 2-hydroxy-5-amino-5′-cyanobiphenyl; 2-hydroxy-5-amino-5′-fluorobiphenyl; 2-hydroxy-5-amino-5′-methoxybiphenyl; 2-hydroxy-5-amino-5′-methyl-biphenyl; 2-hydroxy-5-amino-5′-methylsulfanybiphenyl; 2-hydroxy-5-amino-5′-nitrobiphenyl; 2-hydroxy-5-amino-6′-amino-methylbiphenyl; 2-hydroxy-5-amino-6′-chlorobiphenyl; 2-hydroxy-5-amino-6′-cyanobiphenyl; 2-hydroxy-5-amino-6′-fluorobiphenyl; 2-hydroxy-5-amino-6′-methoxybiphenyl; 2-hydroxy-5-amino-6′-methylbiphenyl; 2-hydroxy-5-amino-6′-methylsulfanylbiphenyl; 2-hydroxy-5-amino-6′-nitrobiphenyl; 2,2′-dihydroxy-5-amino-3′-methylbiphenyl; 2,2′-dihydroxy-5-amino-4′-methylbiphenyl; 2,2′-dihydroxy-5-amino-5′-methylbiphenyl; 2,2′-dihydroxy-5-amino-6′-methylbiphenyl; 2,3′-dihydroxy-5-amino-4′-methylbiphenyl; 2,3′-dihydroxy-5-amino-5′-methylbiphenyl; 2-hydroxy-5-amino-2′,3′-dimethoxybiphenyl; 2-hydroxy-5-amino-2′,3-dimethylbiphenyl; 2-hydroxy-5-amino-2′,4′-dimethoxybiphenyl; 2-hydroxy-5-amino-2′,4′-dimethylbiphenyl; 2-hydroxy-5-amino-2′,5′-dimethoxybiphenyl; 2-hydroxy-5-amino-2′,5′-dimethylbiphenyl; 2-hydroxy-5-amino-2′,6′-dimethoxybiphenyl; 2-hydroxy-5-amino-2′,6′-dimethylbiphenyl; 2-hydroxy-5-amino-3′,4′-dimethoxybiphenyl; 2-hydroxy-5-amino-3′,4′-dimethylbiphenyl; 2-hydroxy-5-amino-3′,5′-dimethoxybiphenyl; 2-hydroxy-5-amino-3′,5′-dimethylbiphenyl; 2-hydroxy-5-amino-2′-met

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