N-benzyl-p-phenylenediamine-derivatives containing coloring...

Details N-benzyl-p-phenylenediamine-derivatives containing coloring... N-benzyl-p-phenylenediamine-derivatives containing coloring...

2002-01-01

2004-02-10

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S411000, C008S412000, C008S416000, C544S180000, C544S182000, C548S561000, C540S001000

Reexamination Certificate

active

06689174

ABSTRACT:

The present invention relates to agents for oxidatively dyeing keratin fibers, especially human hair, on the basis of a combination of a developer and coupler, which contains N-benzyl-p-phenylenediamine derivatives as developer, as well as to new N-benzyl-p-phenylenediamine derivatives.
In the field of dyeing keratin fibers, especially of dyeing hair, oxidation dyes have achieved considerable importance. The dyeing results here from the reaction of certain developers with couplers in the presence of a suitable oxidizing agent. As developers, especially 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol and 1,4-diaminobenzene are used here, while as couplers, resorcinol, 4-chlororesorcinol, 1-naphthol, 3-aminophenol and derivatives of m-phenylenediamine, for example, are named.
Oxidation dyes, which are used for dyeing human hair, must satisfy numerous requirements, in addition to dyeing in the desired intensity. For example, the dyes must be safe from a toxicological and dermatological point of view and the hair dyeings achieved must have good light fastness, permanent waving fastness, acid resistance and crocking fastness. In any case, such dyeings must remain stable for a period of at least 4 to 6 weeks without the action of light, rubbing and chemical agents. In addition, it is necessary that a broad range of different color nuances can be produced by combining suitable developers and couplers.
From the German Offenlegungsschrift 34 32 214, agents, which contain a particular N-benzyl-p-phenylenediamine, such as N-benzyl-p-phenylenediamine, N4-benzyl-1,4-diamino-2-methylbenzene and 2-(((4-aminophenyl)amino)methyl)-4,6-dichloro-phenol, are already known for dyeing hair. However, these compounds do not fulfill the requirements, which must be met by dyes for oxidation dyes, in every respect. There is therefore a continuing need for further, suitable, new dyes.
It has now been found that, if N-benzyl-p-phenylenediamine derivatives of the general Formula (I) are used, intensive brown, blue and red color nuances are obtained.
The object of the present invention therefore is an agent for oxidatively dyeing keratin fibers, such as wool, fur, feathers or hair, especially human hair, on the basis of a combination of developer and coupler, which contains, as developer, at least one N-benzyl-p-phenylenediamine derivative of Formula (I),
in which
R1 R1 is hydrogen, a (C
1
-C
4
) alkyl group or a hydroxy-(C
1
-C
4
) alkyl group,
R2 is hydrogen, a halogen atom (F, Cl, Br, I), a cyano group, a (C
1
-C
4
) alkoxy group, a hydroxy (C
1
-C
4
) alkoxy 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, a (C
1
-C
4
) alkylamino group, a di-(C
1
-C
4
) alkylamino group, a di-(hydroxy-(C
1
-C
4
)-alkyl) amino group, a (hydroxy-(C
1
-C
4
)-alkyl) amino group, a trifluoromethane group, a —C(O)CH
3
group, a —C(O)CF
3
group, an —Si(CH
3
)
3
group, a hydroxy-(C
1
-C
4
) alkyl group, a dihydroxy-(C
3
-C
4
) alkyl group or a morpholino group
R3, R4 independently of one another are hydrogen, a halogen atom, a hydroxy group, a (C
1
-C
4
) alkoxy group, a hydroxy-(C
1
-C
4
) alkoxy group, a (C
1
-C
6
) alkyl group, a (C
1
-C
4
) alkyl thioether group, a mercapto group, an amino group, a (C
1
-C
6
) alkylamino group, a di-(C
1
-C
6
) alkylamino group, a di-(hydroxy-(C
1
-C
4
)-alkylamino group, a hydroxy-(C
1
-C
4
) alkylamino group, a trifluoromethane group, an acetamido group, a —C(O)CH
3
group, a —C(O)CF
3
group, an —Si(CH
3
)
3
group, a hydroxy-(C
1
-C
4
) alkyl group or a dihydroxy-(C
3
-C
4
) alkyl group or R3 and R4 together form an —O—CH2—O— bridge and
R5 is hydrogen, a hydroxy group or a (C
1
-C
6
) alkyl group,
with the proviso that
(i) at least one of the R2 to R5 groups is different from a hydrogen and
(ii) R1 is not hydrogen or a (C1-C4) alkyl group when R2=R4=R5=hydrogen and R3=chlorine.
The following, for example, can be mentioned as examples of compounds of Formula (I): N-((2-aminophenyl)methyl)-1,4-diaminobenzene, N-((3-aminophenyl)-methyl)-1,4-diaminobenzene, N-((3-hydroxyphenyl)methyl)-1,4-diaminobenzene, N-((4-aminophenyl)methyl)-1,4-diaminobenzene, N-((4-hydroxyphenyl)methyl)-1,4-diaminobenzene, N-((2-(1-hydroxyethoxy)-phenyl)-methyl)-1,4-diaminobenzene, N-((2-methoxyphenyl)methyl)-1,4-diaminobenzene, N-((3-(1-hydroxyethoxy)-phenyl)methyl)-1,4diaminobezene, N-((3-methoxyphenyl)methyl)-1,4-diaminobenzene, N-((4-hydroxy-3,5-dimethyl-phenyl)methyl)-1,4-diaminobenzene, N-((4-(1-hydroxyethoxy)-phenyl)methyl)-1,4-diaminobenzene, N-((4-methoxyphenyl)methyl)-1,4-diaminobenzene, N-((2-(2-hydroxyethylamino)-phenyl)methyl)-1,4-diaminobenzene, N-((2-(bis-(2-hydroxyethyl)amino)-phenyl)methyl)-1,4-diaminobenzene, N-((2-dimethylamino-phenyl)methyl)-1,4-diaminobenzene, N-((2-pyrrolidino-phenyl)methyl)-1,4-diaminobenzene, N-((3-(2-hydroxyethylamino)-phenyl)methyl)-1,4-diaminobenzene, N-((3-(bis-(2-hydroxyethyl)amino)-phenyl)methyl)-1,4-diaminobenzene, N-((3-dimethylaminophenyl)methyl)-1,4-diaminobenzene, N-((3-pyrrolidino-phenyl)methyl)-1,4-diaminobenzene, N-((4-(2-hydroxyethylamino)-phenyl)methyl)-1,4-diaminobenzene, N-((4-(bis-(2-hydroxyethyl)amino)-phenyl)methyl)-1,4-diaminobenzene, N-((4-dimethylamino-phenyl)methyl)-1,4-diaminobenzene, N-((4-pyrrolidino-phenyl)methyl)-1,4-diaminobenzene, N-benzo[1,3]dioxol-5-ylmethyl-1,4-diaminobenzene, N-benzo[1,3]dioxol-6-ylmethyl-1,4-diaminobenzene, N-{2-[(4-amino-phenylamino)-methyl]-phenyl}-acetamide, N-{3-[(4-amino-phenylamino)-methyl]-phenyl}-acetamide, N-{4-[(4-amino-phenylamino)-methyl]-phenyl}-acetamide, N-((2,3-diaminophenyl)methyl)-1,4-diaminobenzene, N-((2,3-dihydroxyphenyl)methyl)-1,4-diaminobenzene, N-((2,4-diaminophenyl)methyl)-1,4-diaminobenzene, N-((2,4-dihydroxyphenyl)methyl)-1,4-diaminobenzene, N-((2,5-diaminophenyl)methyl)-1,4-diaminobenzene, N-((2,5-dihydroxyphenyl)methyl)-1,4-diaminobenzene, N-((2,6-diaminophenyl)methyl)-1,4-diaminobenzene, N-((2,6-dihydroxyphenyl)methyl)-1,4-diaminobenzene, N-((2-hydroxy-3-aminophenyl)methyl)-1,4-diaminobenzene, N-((2-hydroxy-4-aminophenyl)methyl)-1,4-diaminobenzene, N-((2-hydroxy-5-aminophenyl)methyl)-1,4-diaminobenzene, N-((3-hydroxy-4-aminophenyl)methyl)-1,4-diaminobenzene, N-((3-hydroxy-5-aminophenyl)methyl)-1,4-diaminobenzene, N-((2-amino-3-hydroxyphenyl)methyl)-1,4-diaminobenzene, N-((2-amino-4-hydroxyphenyl)methyl)-1,4-diaminobenzene, N
1
-((2-aminophenyl)methyl)-2-(2-hydroxyethyl)-1,4-diaminobenzene, N
1
-((2-aminophenyl)methyl)-2-methyl-1,4-diaminobenzene, N
1
-((3-aminophenyl)methyl)-2-(2-hydroxyethyl)-1,4-diaminobenzene, N
1
-((3-aminophenyl)methyl)-2-methyl-1,4-diaminobenzene, N
1
-((3-hydroxyphenyl)methyl)-2-(2-hydroxyethyl)-1,4-diaminobenzene, N
1
-((3-hydroxyphenyl)methyl)-2-methyl-1,4-diaminobenzene, N
1
-((4-aminophenyl)methyl)-2-(2-hydroxyethyl)-1,4-diaminobenzene, N
1
-((4-aminophenyl)methyl)-2-methyl-1,4-diaminobenzene, N
1
-((4-hydroxyphenyl)methyl)-2-(2-hydroxyethyl)-1,4-diaminobenzene, N
1
-((4-hydroxyphenyl)methyl)-2-methyl-1,4-diaminobenzene, N
4
-((2-aminophenyl)methyl)-2-(2-hydroxyethyl)-1,4-diaminobenzene, N
4
-((2-aminophenyl)methyl)-2-methyl-1,4-diaminobenzene, N
4
-((3-aminophenyl)methyl)-2-(2-hydroxyethyl)-1,4-diaminobenzene, N
4
-((3-aminophenyl)methyl)-2-methyl-1,4-diaminobenzene, N
4
-((3-hydroxyphenyl)methyl)-2-(2-hydroxyethyl)-1,4-diaminobenzene, N
4
-((3-hydroxyphenyl)methyl)-2-methyl-1,4-diaminobenzene, N
4
-((4-aminophenyl)methyl)-2-(2-hydroxyethyl)-1,4-diaminobenzene, N
4
-((4-aminophenyl)methyl)-2-methyl-1,4-diaminobenzene, N
4
-((4-hydroxyphenyl)methyl)-2-(2-hydroxyethyl)-1,4-diaminobenzene, N
4
-((4-hydroxyphenyl)methyl)-2-methyl-1,4-diaminobenzene.
Compounds of Formula (I) are preferred in which
(i) R1 and one of the groups R2 to R5 is hydrogen and/or
(ii) three of the R1 to R5 groups are hydrogen and the two remaining groups, independently of one another, represent hydrogen, a methoxy group, a hydroxy group or an amino group or, in the case of R3 and R4, jointly form an

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