P-diaminobenzene derivatives and dyes containing said compounds

Details P-diaminobenzene derivatives and dyes containing said compounds P-diaminobenzene derivatives and dyes containing said compounds

2001-11-09

2004-03-02

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S410000, C008S411000, C008S412000, C008S421000, C564S305000, C564S330000

Reexamination Certificate

active

06699296

ABSTRACT:

The invention relates to novel p-diaminobenzene derivatives and to colorants for dyeing keratin fibers and containing these compounds.
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, 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol, 4-amino-3-methylphenol and 1,4-diaminobenzene, and suitable couplers are, for example, resorcinol, 4-chlororesorcinol, 1-naphthol, 3-aminophenol, 5-amino-2-methylphenol and derivatives of m-phenylenediamine. Moreover, Unexamined German Patent Application [DE-OS] 198 22 041 describes colorants containing as developers p-phenylenediamines substituted in the 2-position.
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 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 color shades.
Currently used colorants, however, do not meet all aspects of the aforesaid requirements.
Hence, there continues to exist a need for novel developers capable of meeting the aforesaid requirements to a very high degree.
Surprisingly, in this regard, we have now found that p-diaminobenzene derivative of general formula (I) meet the requirements placed on developers to a particularly high degree. For example, the use of these developers in combination with known couplers produces intense color shades that are unusually light-fast and wash-fast.
The object of the present invention are therefore p-diaminobenzene derivatives of general formula (I) or physiologically tolerated, water-soluble salts thereof
wherein R1, R2, R3, R4, R5, R6 and R7
independently of each other denote hydrogen, a C
1
-C
6
-alkyl group, a C
1
-C
4
-hydroxyalkyl group, a C
2
-C
4
-dihydroxyalkyl group or a C
1
-C
4
-alkoxy-(C
1
-C
4
)-alkyl group, or R1 and R2 or R3 and R4 or R5 and R6 form a four-membered to eight-membered aliphatic ring, and at least two of the R1 to R7 groups denote hydrogen;
R8 stands for hydrogen or a C
1
-C
4
-alkyl group; and
R9, R10 independently of each other denote hydrogen, a hydroxyl group, a halogen atom, a C
1
-C
4
-alkyl group, a C
1
-C
4
-hydroxyalkyl group, a C
1
-C
4
-aminoalkyl, group, an amino group, a C
1
-C
2
-alkylamino group or a C
1
-C
4
-alkoxy group.
Suitable compounds of formula (I) are, for example:
4-[3-(2,5-diaminophenyl)allylamino]aniline; 4-[3-(2,5-diaminophenyl)allylamino]-2-(2-hydroxyethyl)-aniline; 4-[3-(2,5-diaminophenyl)allylamino]-5-(2-hydroxyethyl)aniline; 4-[3-(2,5-diaminophenyl)allylamino]-2-chloroaniline; 4-[3-(2,5-diaminophenyl)allylamino]-2-methylaniline; 4-[3-(2,5-diaminophenyl)allylamino]-3-(2-hydroxyethyl)aniline; 4-[3-(2,5-diaminophenyl)allylamino]-3-chloroaniline; 4-[3-(2,5-diaminophenyl)allylamino]-3-methylaniline; 4-{3-[2,5-diamino-3-(2-hydroxyethyl)phenyl]allylamino}-aniline; 4-[3-(2,5-diamino-3-chlorophenyl)allylamino]aniline; 4-[3-(2,5-diamino-3-methylphenyl)allyl]-amino]aniline; 4-[3-(2,5-diamino-6-methylphenyl)allylamino]aniline; 4-{3-[2,5-diamino-4-(2-hydroxyethyl)phenyl]allylamino}aniline; 4-[3-(2,5-diamino-4-chlorophenyl)allylamino]aniline; 4-[3-(2,5-diamino-4-methylphenyl)allylamino]aniline; 4-[3-(N
2
,N
2
-bis-methyl-2,5-diaminophenyl)allylamino]-2-aniline; 4-{3-[N
2
,N
2
-bis-(2-hydroxyethyl)-2,5-diaminophenyl]allylamino}-2-aniline; 4-[3-(N
5
,N
5
-bis-methyl-2,5-diaminophenyl)allylamino]-2-aniline; 4-{3-[N
5
,N
5
-bis-(2-hydroxyethyl)-2,5-diaminophenyl]-allylamino}-2-aniline; 4-[3-(2,5-diaminophenyl)allylamino]-2-N,N′-bis-methylaniline; 4-[3-(2,5-diaminophenyl)allylamino]-2-N,N′-bis-(2-hydroxyethyl)aniline or a physiologically tolerated salt thereof.
Preferred are compounds of formula (I) wherein (i) at least one of groups R8 to R10 denotes hydrogen, and/or (ii) R1 and R2 or R3 and R4 or R5 and R6 or all R1 to R4 or R1 to R7 groups denote hydrogen. Also preferred are compounds of formula (I) wherein R8 denotes hydrogen and R5 and R6 independently of each other denote hydrogen, a C
1
-C
4
-alkyl group, a C
1
-C
4
-hydroxyalkyl group or a C
2
-C
4
-dihydroxyalkyl group.
Particularly preferred p-diaminobenzene derivatives of formula (I) are 4-[3-(2,5-diaminophenyl)-allylamino]aniline; 4-[3-(2,5-diaminophenyl)allylamino]-2-(2-hydroxyethyl)aniline; 4-[3-(2,5-diaminophenyl)allylamino]-2-methylaniline; 4-[3-(2,5-diaminophenyl)allylamino]-3-methylaniline; 4-[3-(2,5-diaminophenyl)allylamino]-3-(2-hydroxyethyl)aniline; 4-[3-(2,5-diaminophenyl)allylamino]-2-N,N′-bis-methylaniline; 4-[3-(2,5-diaminophenyl)allylamino]-2-N,N′-bis-(2-hydroxyethyl)aniline or physiologically tolerated salts thereof.
The compounds of formula (I) can be used either as free bases or in the form of their physiologically tolerated salts of inorganic or organic acids, for example hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid or citric acid.
The p-diaminobenzene derivatives of formula (I) can be prepared by known methods of synthesis. For example, the synthesis of the compounds of the invention can be carried out as follows:
By reductive amination of a substituted benzene of formula (II)
wherein Ra denotes a suitable protective group described, for example, in Organic Synthesis, Chapter 7 “Protection for the Amino Group”, page 309 ff., Wiley Interscience, 1991; Rb has the meaning of NR1Ra or NR1R2, with an amine of formula (III)
wherein Rc has the meaning of Ra or R6, R5, R6, R7, R8, R9 and R10 having the same meaning as in formula (I), followed by elimination of the protective group.
The p-diaminobenzene derivatives of formula (I) of the invention are readily water-soluble and give colorations of high color intensity and excellent color fastness, particularly in terms of light fastness, wash fastness and rubbing fastness. The compounds of formula (I) also have excellent storage stability, particularly as constituents of the colorants described in the following.
Hence, another object of the present invention are compositions for oxidative dyeing of keratin fibers, for example hair, furs, feathers or wool, particularly human hair, based on a developer-coupler combination, said compositions containing as the developer at least one p-diaminobenzene derivative of formula (I).
The p-diaminobenzene derivatives of formula (I) are contained in the colorants of the invention in a total amount of about 0.005 to 20 wt. %, an amount from about 0.01 to 5.0 wt. % and particularly from 0.1 to 5 wt. % being preferred.
Preferred couplers are 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-methyl-benzene, 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-1-(2-hydroxyethoxy)-4-methylaminobenzene, 2,4-diaminopheno

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