Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2002-06-26
2004-11-02
Gupta, Yogendra N. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S408000, C008S410000, C008S411000, C008S412000, C008S416000, C008S423000, C008S574000, C008S577000, C548S563000, C548S577000, C549S200000
Reexamination Certificate
active
06811573
ABSTRACT:
The invention relates to agents for oxidative dyeing of keratin fibers, particularly human hair, based on a developer/coupler combination containing as the coupler a 1,3-diamino-4-heteroarylbenzene derivative, as well as to novel 1,3-diamino-4-heteroarylbenzene derivatives.
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, 1,4-diaminobenzene and 4,5-diamino-1-(2′-hydroxyethyl)pyrazole and suitable couplers are, for example, resorcinol, 2-aminoresorcinol, 1-naphthol, 3-aminophenol, m-phenylenediamine, 2-amino-4-(2′-hydroxyethyl)aminoanisole, 1,3-diamino-4-(2′-hydroxyethoxy)benzene and 2,4-diamino-5-fluorotoluene.
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 obtained must have good light fastness, resistance to permanent waving, acid fastness and rubbing fastness. In any case, however, in the absence of exposure to light, rubbing and chemicals such colorations must remain stable over a period of at least 4 to 6 weeks. Moreover, by combining appropriate developers and couplers, it must be possible to create a wide range of different color shades.
Attempts have already been made to improve the properties of m-phenylenediamines by introduction of substituents. In this respect, the reader is referred to German Unexamined Patent Application DE-OS 30 28 131 which, among other things, describes colorants containing as couplers special m-phenylenediamines alkyl-substituted in the 4-position.
The hitherto known colorants, however, do not fully meet all requirements placed on colorants. Hence, a need continued to exist for novel couplers capable of meeting the aforecited requirement to a major extent.
We have now found that by use of 1,3-diamino-4-heteroarylbenzene derivatives of general formula (I) it is possible to achieve intense, stable blue color shades in addition to natural, purple or violet ones.
Hence, the object of the present invention is an agent 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 coupler at least one 1,3-diamino-4-heteroarylbenzene derivative of formula (I) or a physiologically tolerated salt thereof,
wherein
X1 denotes sulfur, oxygen, C—R3 or N—R2;
X2 denotes nitrogen or C—R4;
X3 denotes sulfur, nitrogen, oxygen, CR—5 or N—R2;
R1, R3, R4 and R5 can be equal or different and independently of each other denote hydrogen, a halogen atom (fluorine, chlorine, bromine or iodine), a cyano group, a C
1
-C
4
-alkoxy group, a C
1
-C
6
-alkyl group, a C
1
-C
4
-alkylthioether group, a mercapto group, a nitro group, an amino group, a C
1
-C
4
-monoalkylamino group, a di(C
1
-C
4
)alkylamino group, a di(C
1
-C
4
-hydroxyalkyl)amino group, a C
1
-C
4
-hydroxyalkylamino group, a trifluoromethane 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 or a C
3
-C
4
-dihydroxyalkyl group;
R2 denotes hydrogen, a C
1
-C
6
-alkyl group, a C
2
-C
4
-hydroxyalkyl group, a phenyl group or an acetyl group;
wherein at least one and at the most two X1 to X3 groups denote C—R3, or C—R4 or C—R5, and at the most one of the X1 to X3 groups denotes sulfur, oxygen or N—R2.
Compounds of formula (I) are, for example:
1,3-diamino-4-(2-thiophenyl)benzene, 1,3-diamino-4-(3-thiophenyl)benzene, 1,3-diamino-4-(1-methyl-1H-2-pyrrolyl)benzene, 1,3-diamino-4-(2-pyrrolyl)benzene, 1,3-diamino-4-(2-furyl)benzene, 1,3-diamino-4-(2-thiazolyl)benzene, 1,3-diamino-4-(1H-2-imidazolyl)benzene, 1,3-diamino-4-(3-furyl)benzene, 1,3-diamino-4-(3-amino-2-thiophenyl)benzene, 1,3-diamino-4-(3-chloro-2-thiophenyl)benzene, 1,3-diamino-4-(3-methyl-2-thiophenyl)benzene, 1,3-diamino-4-(3-nitro-2-thiophenyl)-benzene, 1,3-diamino-4-(4-amino-2-thiophenyl)benzene, 1,3-diamino-4-(4-chloro-2-thiophenyl)benzene, 1,3-diamino-4-(4-methyl-2-thiophenyl)benzene, 1,3-diamino-4-(4-nitro-2-thiophenyl)benzene, 1,3-diamino-4-(5-amino-2-thiophenyl)benzene, 1,3-diamino-4-(5-chloro-2-thiophenyl)benzene, 1,3-diamino-4-(5-methyl-2-thiophenyl)benzene, 1,3-diamino-4-(5-nitro-2-thiophenyl)benzene, 1,3-diamino-(2-amino-3-thiophenyl)benzene, 1,3-diamino-(2-chloro-3-thiophenyl)benzene, 1,3-diamino-(2-methyl-3-thiophenyl)benzene, 1,3-diamino-(2-nitro-3-thiophenyl)benzene, 1,3-diamino-(4-amino-3-thiophenyl)benzene, 1,3-diamino-(4-chloro-3-thiophenyl)benzene, 1,3-diamino-(4-methyl-3-thiophenyl)benzene, 1,3-diamino-(4-nitro-3-thiophenyl)benzene, 1,3-diamino-(5-amino-3-thiophenyl)benzene, 1,3-diamino-(5-chloro-3-thiophenyl)benzene, 1,3-diamino-(5-methyl-3-thiophenyl)benzene and 1,3-diamino-(5-nitro-3-thiophenyl)benzene.
Preferred compounds of formula (I) are those wherein (i) X1 or X3 denotes sulfur, X2 denotes C—R4 and X3 denotes C—R5 or X1 denotes C—R3; or (ii) X1 or X3 stands for sulfur, X2 stands for C—R4 and X3 stands for C—R5 or X1 stands for C—R3, and at least two of the R1, R3, R4 and R5 groups denote hydrogen.
Particularly preferred are the following 1,3-diamino-4-heteroarylbenzene derivatives: 1,3-diamino-4-(2-thiophenyl)benzene, 1,3-diamino-4-(3-thiophenyl)benzene and the physiologically tolerated salts thereof.
The compounds of formula (I) can be used as free bases or in the form of their physiologically tolerated salts with inorganic or organic acids, for example hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid or citric acid.
The 1,3-diamino-4-heteroarylbenzene derivatives of formula (I) are contained in the colorant of the invention in a total amount of about 0.005 to 20 wt. %, an amount of about 0.01 to 5 wt. % and particularly 0.1 to 2.5 wt. % being preferred.
Suitable developers are all developers known to be used for such colorants, for example 1,4-diaminobenzene (p-phenylenediamine), 1,4-diamino-2-methylbenzene (p-toluylenediamine), 1,4-diamino-2,6-dimethylbenzene, 1,4-diamino-3,5-diethylbenzene, 1,4-diamino-2,5-dimethylbenzene, 1,4-diamino-2,3-dimethylbenzene, 2-chloro-1,4-diaminobenzene, 1,4-diamino-2-(2-thiophenyl)benzene, 1,4-diamino-2-(3-thiophenyl)benzene, 1,4-diamino-2-(3-pyridinyl)benzene, 2,5-diaminobiphenyl, 1,4-diamino-2-methoxymethylbenzene, 1,4-diamino-2-aminomethylbenzene, 1,4-diamino-2-hydroxymethylbenzene, 1,4-diamino-2-(2-hydroxyethoxy)benzene, 1-(2,5-diaminophenyl)-ethanol, 2-[2-(acetylamino)ethoxy]-1,4-diaminobenzene, 4-phenylaminoaniline, 4-dimethylaminoaniline, 4-diethylaminoaniline, 4-dipropylaminoaniline, 4-[ethyl-(2-hydroxyethyl)amino]aniline, 4-[di(2-hydroxyethyl)amino]aniline, 4-[di(2-hydroxyethyl)-amino]-2-methylaniline, 4-[(2-methoxyethyl)amino]aniline, 4-[(3-hydroxypropyl)amino]-aniline, 4-[(2,3-dihydroxypropyl)amino]aniline, 1,4-diamino-2-(2-hydroxyethyl)benzene, 1,4-diamino-2-(1-methylethyl)benzene, 1,3-bis[(4-aminophenyl)(2-hydroxyethyl)amino]-2-propanol, 1,4-bis[(4-amino-phenyl)amino]butane, 1,8-bis(2,5-diaminophenoxy)-3,6-dioxaoctane, 4-aminophenol, 4-amino-3-methylphenol, 4-amino-3-(hydroxymethyl)phenol, 4-amino-3-fluorophenol, 4-methylaminophenol, 4-amino-2-(aminomethyl)phenol, 4-amino-2-(hydroxymethyl)phenol, 4-amino-2-fluorophenol, 4-amino-2-[(2-hydroxyethyl)amino]methylphenol, 4-amino-2-methylphenol, 4-amino-2-methoxymethyl)phenol, 4-amino-2-(2-hydroxyethyl)phenol, 5-aminosalicylic acid, 2,5-diaminopyridine, 2,4,5,6-tetraaminopyrimidine, 2,5,6-triamino-4-(1H)-pyrimidone, 4,5-diamino-1-(2-hydroxyethyl)-1H-pyrazole, 4,5-diamino-1-(1-methylethyl)-1H-pyrazole, 4,5-diamino-1-[(4-methylphenyl)methyl]-1H-pyrazole, 1-[(4-chlorophenyl)methy
Braun Hans-Juergen
Chassot Laurent
Elhilo Eisa
Gupta Yogendra N.
Striker Michael J.
Wella Aktiengesellschaft
LandOfFree
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