Oxidizing hair coloring agents containing...

Details Oxidizing hair coloring agents containing... Oxidizing hair coloring agents containing...

2000-03-14

2002-12-31

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S405000, C008S406000, C008S407000, C008S409000, C008S410000, C008S411000

Reexamination Certificate

active

06500213

ABSTRACT:

The present invention relates to agents for oxidative coloring of keratin fibers, particularly human hair, based on a developer/coupler combination and which contain as the developer a 2,5-diamino-1-phenylbenzene derivative and to novel 2,5-diamino-1-phenylbenzene derivatives.
Oxidation dyes have become very important for the coloring of keratin fibers, particularly in the field of hair coloring. In this case, the color is created by reaction of certain developers with certain couplers in the presence of an appropriate oxidant. Suitable developers for this purpose are, in particular, 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol and 1,4-diaminobenzene. Suitable couplers are, for example, resorcinol 4-chlororesorcinol, 1-naphthol, 3 aminophenol and derivatives of m-phenylenediamine.
Oxidation dyes used for coloring human hair must meet many special requirements besides producing colorations of a desired intensity. The dyes must be toxicologically and dermatologically harmless, and the resulting hair colors must have good light, permanent wave, acid and rubbing resistance. The hair colors must also remain stable for a period of at least four to six weeks in the absence of light, rubbing and chemicals. In addition, it must be possible, by means of a combination of appropriate developers and couplers, to create a wide range of different color shades.
Currently used coloring agents, however, do not meet the aforesaid requirements in all respects.
Hence, a need continues to exist for novel developers which will meet the aforesaid requirements to a high degree.
In this regard, we have now found that 1,4-diaminobenzene derivatives of general formula (I) meet the requirements placed on developer components to an unusually high degree. Thus, by use of such developer components together with known coupler components, intense color shades are obtained which are unusually resistant to light and washing.
The object of the present invention are agents for oxidative coloring of keratin fibers, for example wool, furs, feathers or hair, particularly human hair, based on a developer-coupler combination containing as the developer a 2,5-diamino-1-phenylbenzene derivative of general formula (I)
wherein
R1, R2, R3 and R4 independently of each other denote hydrogen, a C
1
-C
6
alkyl, C
1
-C
4
hydroxyalkyl, C
2
-C
4
dihydroxyalkyl or C
1
-C
4
alkoxy-(C
1
-C
4
)alkyl group, or R1 and R2 or R3 and R4 form a four-membered to eight-membered aliphatic ring, with at least two of the R1 to R4 groups denoting hydrogen;
R5 denotes hydrogen, a hydroxyl group, a halogen atom or a C
1
-C
4
alkyl, C
1
-C
4
hydroxyalkyl or C
1
-C
4
alkoxy group;
R6, R7, R8, R9 and R10 independently of each other denote hydrogen, a halogen atom or a cyano, hydroxyl, C
1
-C
4
alkoxy, C
1
-C
8
alkyl, C
1
-C
4
alkyl thioether, mercapto, nitro, amino, alkylamino, dialkylamino, trifluoromethane, —C(OH), —C(O)CH
3
, —C(O)CF
3
, —Si(CH
3
)
3
, C
1
-C
4
hydroxyalkyl, C
1
-C
4
dihydroxyalkyl, —CH═CHR11 or —(CH
2
)
p
—CO
2
R12 group or a —(CH
2
)
p
—R13 group, where p=1, 2, 3 or 4, or a —C(R14)═NR15 group or a C(R17)H—NR18R19 group, or two adjacent R6 to R10 groups form a —O—CH
2
—O bridge;
R11 denotes hydrogen, a hydroxyl, nitro, amino, CO
2
R12 or —C(O)CH
3
group;
R12, R14 and R17 independently od each other denote hydrogen or a C
1
-C
4
alkyl group;
R13 denotes an amino or nitrile group;
R15, R18 and R19 independently of each other denote hydrogen, a hydroxyl, C
1
-C
4
alkyl, C
1
-C
4
hydroxyalkyl or C
3
-C
4
dihydroxyalkyl group or a radical of formula
R16 denotes hydrogen, an amino group or a hydroxyl group,
or containing a the physiologically tolerated, water-soluble salt thereof.
Suitable compounds of formula (I) are, for example:
2,5-diamino-1-phenylbenzene; 2,5-diamino-1-(4-bromophenyl)benzene; 2,5-diamino-1-phenyl-1-(4-ethenylphenyl)benzene; 2,5-diamino-1-(2,3,4-trimethoxyphenyl)benzene; 2,5-diamino-1-[2,4-di(2-hydroxyethyl)aminophenyl]benzene; 2,5-diamino-1-(2,4-diaminophenyl)benzene; 2,5-diamino-1-(2,4-dihydroxyphenyl)benzene; 2,5-diamino-1-(2,4-dimethylaminophenyl)benzene; 2,5-diamino-1-(2,4-methoxyphenyl)benzene; 2,5-diamino-1-[2,5-di(2-hydroxyethyl)aminophenyl]benzene; 2,5-diamino-1-(2,5-diaminophenyl)benzene; 2,5-diamino-1-(2,5-dihydroxyphenyl)benzene; 2,5-diamino-1-(2,5-dimethoxyphenyl)benzene; 2,5-diamino-1-(2,5-dimethylaminophenyl)benzene; 2,5-diamino-1-[2,6-di(2-hydroxyethyl)aminophenyl; 2,5-diamino-1-(2,6-diaminophenyl]benzene; 2,5-diamino-1-(2,6-dihydroxyphenyl)benzene; 2,5-diamino-1-(2,6-dimethoxyphenyl)benzene; 2,5-diamino-1-(2,6-dimethylaminophenyl)benzene; 2,5-diamino-1-[2-(bromomethyl)phenyl]benzene; 2,5-diamino-1-(2-amino-5-hydroxyphenyl)-benzene; 2,5-diamino-1-(2-aminophenyl)benzene; 2,5-diamino-1-(2-carboxyphenyl)benzene; 2,5-diamino-1-(2-chlorophenyl)benzene; 2,5-diamino-1-[2-di(2-hydroxyethyl)aminophenyl]benzene; 2,5-diamino-1-(2-dimethylaminophenyl)benzene; 2,5-diamino-1-(2-fluorophenyl)benzene; 2,5-diamino-1-(2-formylphenyl)benzene; 2,5-diamino-1-(2-hydroxy-4-aminophenyl)benzene; 2,5-diamino-1-(2-hydroxy-5-aminophenyl)benzene; 2,5-diamino-1-(2-hydroxyphenyl)benzene; 2,5-diamino-1-(2-methoxyphenyl)benzene; 2,5-diamino-1-(2-methylphenyl)benzene; 2,5-diamino-1-(2-nitrophenyl)benzene; 2,5-diamino-1-(2-trifluoromethylphenyl)benzene; 2,5-diamino-1-[3,5-di(2-hydroxyethyl)aminophenyl]benzene; 2,5-di-amino-1-(3,5-diaminophenyl)benzene; 2,5-diamino-1-(3,5-dihydroxyphenyl)benzene; 2,5-diamino-1-(3,5-dihydroxyphenyl)benzene; 2,5-diamino-1-(3,5-dimethylaminophenyl)benzene; 2,5-diamino-1-(3-aminophenyl)benzene; 2,5-diamino-1-(3-bromophenyl)benzene; 2,5-diamino-1-(3-carboxyphenyl)benzene; 2,5-diamino-1-(3-chlorophenyl)benzene; 2,5-diamino-1-[3-di(2-hydroxyethyl)aminophenyl]benzene; 2,5-diamino-1-(3-dimethylaminophenyl)benzene; 2,5-diamino-1-(3-fluorophenyl)benzene; 2,5-diamino-1-(3-formylphenyl)benzene; 2,5-diamino-1-(3-hydroxy-5-aminophenyl)benzene; 2,5-diamino-1-(3-hydroxy-phenyl)benzene; 2,5-diamino-1-(3-methoxyphenyl)benzene; 2,5-diamino-1-(3-nitrophenyl)benzene; 2,5-diamino-1-(3-fluoromethylphenyl)benzene; 2,5-diamino-1-[4-(dimethylamino)phenyl]benzene; 2,5-diamino-1-[4-(hydroxymethyl)phenyl]benzene; 2,5-diamino-1-[4-(methylthio)phenyl]benzene; 2,5-diamino-1-[4-(trifluoromethyl)phenyl]benzene; 2,5-diamino-1-[4-(trimethylsilyl)phenyl]benzene; 2,5-diamino-1-(4-acetylphenyl)benzene; 2,5-diamino-1-(4-aminophenyl)benzene; 2,5-diamino-1-(4-carboxyphenyl)benzene; 2,5-diamino-1-(4-chlorophenyl)benzene; 2,5-diamino-1-[4-(di(2-hydroxyethyl)aminophenyl]benzene; 2,5-diamino-1-(4-dimethylaminophenyl)benzene; 2,5-diamino-1-(4-ethoxyphenyl)benzene; 2,5-diamino-1-(4-fluorophenyl)benzene; 2,5-diamino-1-(4-formylphenyl)benzene; 2,5-diamino-1-(4-hydroxyphenyl)benzene; 2,5-diamino-1-(4-methoxyphenyl)benzene; 2,5-diamino-1-(4-methylphenyl)benzene; 2,5-diamino-1-phenylbenzene; 2,5-diamino-4-chloro-1-phenylbenzene; 2,5-diamino-4-methoxy-1-phenylbenzene; 2,5-diamino-4-methyl-1-phenylbenzene; 2-amino-5-(2,3-dihydroxypropyl)amino-1-(2,3,4-trimethoxyphenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)amino-1-(2,4-dihydroxyphenyl)-benzene; 2-amino-5-(2,3-dihydroxypropyl)amino-1-(2,5-diaminophenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)amino-1-(2,6-dimethoxyphenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)amino-1-(2-amino-5-hydroxyphenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)amino-1-(2-aminophenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)amino-1-(2-hydroxy-4-aminophenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)amino-1-(2-hydroxy-5-aminophenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)amino-1-(2-hydroxyphenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)-1-(2-methoxyphenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)amino-1-(2-methylphenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)-amino-1-(3,5-diaminophenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)amino-1-(3,5-dihydroxy-phenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)amino-1-(3-aminophenyl)benzene; 2-amino-5-(2,3-dihydroxypropyl)amin

Affiliated with

Also associated with

Rating

Oxidizing hair coloring agents containing... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Oxidizing hair coloring agents containing..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Oxidizing hair coloring agents containing... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2978119