Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Patent
1996-08-12
1998-05-19
Lieberman, Paul
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
8406, 8407, 8423, 8567, A61K 713
Patent
active
057529841
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to the use of 1,2,3,4-tetrahydroquinoxalines as oxidation dye precursors in oxidative coloring formulations for coloring keratin fibers, more especially human hair. The 1,2,3,4-tetrahydroquinoxalines are particularly suitable for use a secondary intermediates in conjunction with primary intermediates.
Oxidative coloring formulations normally contain oxidation dye precursors in a water-containing carrier. Primary intermediates and secondary intermediates are used as oxidation dye precursors. The primary intermediates form the actual dyes with one another or by coupling with or more secondary intermediates under the influence of oxidizing agents or atmospheric oxygen.
2. Discussion of Related Art
1,2,3,4-Tetrahydroquinoxalines have never been described as oxidation dye precursors. By contrast, the use of nitro-substituted 1,2,3,4-nitroquinoxalines as substantive dyes is known from DE-A-38 25 212 and from DE-A-42 06 537. It has now been found that specifically substituted 1,2,3,4-tetrahydroquinoxalines are particularly suitable as oxidation dye precursors in oxidative coloring formulations for keratin fibers because they satisfy the requirements oxidation dye precursors are expected to meet (high color intensity of the colors obtained, fastness to light, fastness to washing, fastness to rubbing) particularly effectively. They act as secondary intermediates and differ from conventional secondary intermediates in their orthodiamino functional unit. Secondary intermediates are normally meta-disubstituted aromatic compounds.
DESCRIPTION OF THE INVENTION
The present invention relates to the use of 1,2,3,4-tetrahydroquinoxalines corresponding to formula I: ##STR2## in which R.sup.1, R.sup.2 and R.sup.3 independently of one another represent hydrogen, C.sub.1-4 alkyl groups, benzyl groups, 2-phenylethyl groups or C.sub.2-4 hydroxyalkyl groups and X, Y and Z represent hydrogen, fluorine, chlorine, bromine or iodine atoms, C.sub.1-4 alkyl groups or NR.sup.4 R.sup.5 groups, where R.sup.4 and R.sup.5 independently of one another represent hydrogen, C.sub.1-4 alkyl groups and C.sub.2-4 hydroxyalkyl groups, although at least one of the groups X, Y and Z is hydrogen, as oxidation dye precursors in oxidative coloring formulations for coloring keratin fibers. Keratin fibers in the context of the invention are pelts, wool or feathers, but especially human hair.
Particularly preferred 1,2,3,4-tetrahydroquinoxalines corresponding to formula I are those in which R.sup.2 and Z are hydrogen, R.sup.1 and R.sup.3 are hydrogen or C.sub.2-4 hydroxyalkyl groups and X and Y are methyl groups, chlorine atoms or NH.sub.2 groups. 5-Methyl- and 6-methyl-1,2,3,4-tetrahydroquinoxaline are particularly preferred.
The invention includes the salts of 1,2,3,4-tetrahydroquinoxalines corresponding to formula I, the hydrochlorides, hydrobromides and sulfates being mentioned in particular.
Some of the 1,2,3,4-tetrahydroquinoxalines corresponding to formula I are compounds known from the literature which may be synthesized in accordance with the model of the literature references cited in the Examples. Others are new substances which may be obtained from the corresponding quinoxalines or nitroquinoxalines by catalytic hydrogenation. A more detailed description is given in the Examples.
Accordingly, the present invention relates to new 1,2,3,4-tetrahydroquinoxalines corresponding to formula I, at least one of the groups R.sup.1 and R.sup.3 being a C.sub.2-4 hydroxyalkyl group.
The present invention also relates to new 1,2,3,4-tetrahydroquinoxalines corresponding to formula I, in which X and Y are both C.sub.1-4 alkyl groups.
In conjunction with typical primary intermediates, the 1,2,3,4-tetrahydroquinoxalines corresponding to formula I provide a broad spectrum of interesting oxidation dyes ranging from yellow to dark brown in color which, by virtue of their brilliance and favorable fastness properties, are particularly suitable for coloring human hair.
Typical developer co
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A. Nose et al., Yakugaku Zasshi 99 (1979) 1240 No Date Available.
"N-Alkylation of Aromatic Amines by Means of Alcohol IV," Miyano et al., Chem. Phar. Bull., vol. 20, pp. 1328-1331, 1972.
"Effects of Structure on the Ease of Electron Removal from o-Phenylenediamines," Nelsen et al, J. Org. Chem., vol. 46, pp. 283-289, 1981.
Hoeffkes Horst
Knuebel Georg
Meinigke Bernd
Rose David
Dusheck Caroline L.
Grandmaison Real J.
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Lieberman Paul
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