Substituted 1,4 diaminobenzene compounds and oxidation dye...

Details Substituted 1,4 diaminobenzene compounds and oxidation dye... Substituted 1,4 diaminobenzene compounds and oxidation dye...

2000-11-03

2003-08-05

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S405000, C008S407000, C008S408000, C008S409000, C008S416000, C564S050000

Reexamination Certificate

active

06602302

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to new substituted 2,5-diamino-1-aminomethylbenzene compounds and oxidation dye precursor compositions for dyeing keratin fibers, especially human hair, containing these compounds.
2. Prior Art
Oxidation dyes have been important in the field of dyeing keratin fibers, especially human hair, for a long time. Dyeing occurs by reaction of certain developer substances alone or with certain coupler substances in the presence of a suitable oxidizing agent. It is known from DE-PS 47349 that keratin fibers can be dyed in bright blond to bluish-black color tones by p-phenylenediamine according to the oxidizing agent used. Blue color tones are produced however by a combination of p-phenylenediamine and its derivative compounds with certain coupler substances. Since only compounds that have specifications or properties that, on the one hand, protect the user sufficiently and, on the other hand, produce a stable resistant color that lasts for a sufficient time can be employed, the selection of suitable developer and coupler substances is limited.
SUMMARY OF THE INVENTION
It has now been surprisingly found that certain p-phenylenediamine derivative compounds permit dyeing of keratin fibers, especially human hair, an intense blue color, even without addition of a coupler substance.
Thus intense colors, which are extraordinarily light-fast and wash-fast, are obtained when these p-phenylenediamine derivative compounds are used in an oxidizing medium
According to the present invention these p-phenylenediamine derivative compounds are substituted 2,5-diamino-1-aminomethylbenzene compounds of formula (I), or their physiologically compatible water-soluble salts,
wherein
R1, R2, R3, R4, R5, R6 and R7, independently of each other, each represent H, a C
1
- to C
6
-alkyl group, a C
1
- to C
4
-hydroxyalkyl group, a C
2
- to C
4
-dihydroxyalkyl group or a C
1
- to C
4
-alkoxy-(C
1
- to C
2
-)alkyl group or R1 and R2 and/or R3 and R4 and/or R5 and R6 together with the N atom form a four-member to eight-member aliphatic ring, with the proviso that at least two of the groups R1 to R6 each represent hydrogen;
R8 represents hydrogen, a halogen atom, a C
1
- to C
4
-alkyl group, a C
1
- to C
4
-hydroxyalkyl group or a C
1
- to C
4
-alkoxy group;
R9 represents a hydrogen, a halogen atom, a cyano group, a hydroxy group, a C
1
- to C
4
-alkoxy group, a C
1
- to C
4
-hydroxyalkoxy group, a C
1
- to C
6
-alkyl group, a C
1
- to C
4
-alkylthioether group; a mercapto group; an amino group, a C
1
- to C
4
-alkylamino group, a C
1
- to C
4
-hydroxyalkylamino group, a di(C
1
- to C
4
-alkyl)amino group, a di(C
1
- to C
4
-hydroxyalkyl)amino group, a {dihydroxy(C
2
- to C
4
)-alkyl}amino group, a (C
1
- to C
4
-hydroxyalkyl)-C
1
-C
4
-alkylamino group, a trifluoromethane group, a C
1
-C
4
-hydroxyalkyl group or a C
3
-C
4
dihydroxyalkyl group; and
R10 represents hydrogen or a C
1
- to C
6
-alkyl group.
For example, the following compounds of formula (I) can be named as examples: 2-((2-amino-phenylamino)-methyl)-1,4-diaminobenzene; 2-((2-bis(hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene; 2-((2-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene; 2-((3-aminophenylamino)methyl)-1,4-diaminobenzene; 2-((3-bis(hydroxyethyl)aminophenylamino)methyl)-1,4-diaminobenzene; 2-((3-dimethylaminophenylamino)-methyl)-1,4-diaminobenzene; 2-((4-amino-phenylamino)methyl)-1,4-diaminobenzene; 2-((4-bis-(hydroxyethyl)aminophenylamino)methyl)-1,4-diaminobenzene; 2-((4-dimethylamino-phenylamino)methyl)-1,4-diaminobenzene; N
1
,N
1
-bis(hydroxyethyl)-2-((2-aminophenylamino)methyl)-1,4-diaminobenzene; N
1
,N
1
-bis(hydroxyethyl)-2-((2-bis(hydroxyethyl)aminophenylamino)-methyl)-1,4-diaminobenzene; N
1
, N
1
-bis-(hydroxyethyl)-2-((2-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
,N
1
-bis(hydroxyethyl)-2-((3-amino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
,N
1
-bis(hydroxyethyl)-2-((3-bis(hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
,N
1
-bis(hydroxyethyl)-2-((3-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
,N
1
-bis(hydroxyethyl)-2-((4-amino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
,N
1
-bis(hydroxyethyl)-2-((4-bis(hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
,N
1
-bis(hydroxyethyl)-2-((4-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
-dihydroxypropyl-2-((2-amino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
-dihydroxypropyl-2-((2-bis(hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
-dihydroxypropyl-2-((2-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
-dihydroxypropyl-2-((3-amino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
-dihydroxypropyl-2-((3-bis-(hydroxyethyl)aminophenylamino)-methyl)-1,4-diaminobenzene; N
1
-dihydroxypropyl-2-((3-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
-dihydroxypropyl-2-((4-amino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
-dihydroxypropyl-2-((4-bis(hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
-dihydroxypropyl-2-((4-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
-hydroxyethyl-2-((2-aminophenylamino)-methyl)-1,4-diaminobenzene; N
1
-hydroxyethyl-2-((2-bis(hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
-hydroxyethyl-2-((2-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
-hydroxyethyl-2-((3-amino-phenylamino)-methyl)-1,4-diaminobenzene; N
1
-hydroxyethyl-2-((3-bis(hydroxyethyl)amino-phenylamino)methyl)1,4-diaminobenzene; N
1
-hydroxyethyl-2-((3-dimethylamino-phenylamino)methyl)-1,4-diaminobenzene; N
1
-hydroxyethyl-2-((4-aminophenylamino)-methyl)-1,4-diaminobenzene; N
1
-hydroxyethyl-2-((4-bis(hydroxyethyl)-aminophenylamino)-methyl)-1,4-diaminobenzene; N
1
-hydroxyethyl-2-((4-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene; N
4
,N
4
-bis(hydroxyethyl)-2-((2-amino-phenylamino)-methyl)-1,4-diaminobenzene; N
4
,N
4
-bis-(hydroxyethyl)-2-((2-bis(hydroxyethyl)aminophenylamino)-methyl)-1,4-diaminobenzene; N
4
,N
4
-bis(hydroxyethyl)-2-((2-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene; N
4
,N
4
-bis(hydroxyethyl)-2-((3-aminophenylamino)-methyl)-1,4-diaminobenzene; N
4
,N
4
-bis(hydroxyethyl)-2-((3-bis(hydroxyethyl)aminophenylamino)-methyl)-1,4-diaminobenzene; N
4
,N
4
-bis(hydroxyethyl)-2-((3-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene; N
4
,N
4
-bis(hydroxyethyl)-2-((4-amino-phenylamino)-methyl)-1,4-diaminobenzene; N
4
,N
4
-bis-(hydroxyethyl)-2-((4-bis(hydroxyethyl)aminophenylamino)-methyl)-1,4-diaminobenzene; N
4
,N
4
-bis(hydroxyethyl)-2-((4-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene; N
4
-dihydroxypropyl-2-((2-aminophenylamino)-methyl)-1,4-diaminobenzene, N
4
-dihydroxypropyl-2-((2-bis(hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene; N
4
-dihydroxypropyl-2-((2-dimethylamino-phenylamino)methyl)-1,4-diaminobenzene; N
4
-dihydroxypropyl-2-((3-amino-phenylamino)-methyl)-1,4-diaminobenzene; N
4
-dihydroxypropyl-2-((3-bis-(hydroxyethyl)aminophenylamino)-methyl)-1,4-diaminobenzene; N
4
-dihydroxypropyl-2-((3-dimethylaminophenylamino)-methyl)-1,4-diaminobenzene; N
4
-dihydroxypropyl-2-((4-amino-phenylamino)-methyl)-1,4-diaminobenzene; N
4
-dihydroxypropyl-2-((4-bis(hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene; N
4
-dihydroxypropyl-2-((4-dimethylaminophenylamino)-methyl)-1,4-diaminobenzene; N
4
-hydroxyethyl-2-((2-aminophenylamino)methyl)-1,4-diaminobenzene, N
4
-hydroxyethyl-2-((2-bis(hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene; N
4
-hydroxyethyl-2-((2-dimethylamino-phenylamino)-methy)-1,4-diaminobenzene; N
4
-hydroxyethyl-2-((3-amino-phenylamino)-methyl)-1,4-diaminobenzene-N
4
-hydroxyethyl-2-((3-bis(hydroxy-ethyl)amino-phenylamino)methyl)-1,4-diaminobenzene; N
4
-hydroxyethyl-2-((3-dimethylaminophenylamino)methyl)-1,4-diaminobenzene; N
4
-hydroxyethyl-2-((4-aminophenylamino)-methyl)-1,4-diaminobenzene; N
4
-hydroxyethyl-2-((4-aminophenylamino)-methyl)-1,4-diaminobenzene; N
4
-hydroxyethyl-2-((4-bis(hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene; N
4
-hyd

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