Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Patent
1992-10-09
1993-09-21
Lieberman, Paul
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
8406, 8408, 8409, 8410, 8412, 8414, 8416, 8421, 8423, 424 70, A61K 713
Patent
active
052464660
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention relates to the use of 1,3-disubstituted 2-nitrobenzenes for the production of oxidation dyes, more particularly for the production of hair dyes.
STATE OF THE INVENTION
Oxidation dyes contain oxidation dye precursors in a suitable carrier. The oxidation dye precursors used are primary intermediate compounds which form intensive colors by oxidative coupling with one another or with one or more color modifiers in the presence of atmospheric oxygen. Suitable primary intermediate compounds are, for example, primary aromatic amines containing another free or substituted hydroxy or amino group in the para position or ortho position and also diaminopyridines, heterocyclic hydrazone derivatives, 4-aminopyrazolone derivatives and tetraaminopyrimidines.
The dyes obtainable by coupling of the primary intermediate components with one another are generally unsatisfactory. However, colors of high intensity and brilliance can often be obtained by coupling with phenols or aromatic amines.
Suitable color modifiers are, for example, m-phenylene diamines, m-aminophenols, resorcinols, naphthols and pyrazolones.
One of the most important applications of oxidation dyes is in the coloring of hair. Good oxidation hair dye precursors have to satisfy above all the following requirements: they must produce the required tints in sufficient intensity in the oxidative coupling reaction. In addition, they must be readily absorbable by human hair without excessively staining the scalp. In addition, the dye should be absorbed uniformly, i.e. the more seriously damaged hair ends should not be colored to a greater extent than the less damaged hair roots. The colors produced should show high stability to heat, light and the chemicals used for permanent waving. Finally, the oxidation hair dye precursors should be toxicologically and dermatologically safe.
Although nitrophenols and nitroanilines have certain coloring properties for keratin fibers, they are not normally suitable as color modifiers because the nitro group deactivates the aromatic core for the coupling reaction. The use of resorcinol as a color modifier is known from DEPSS 162 625 and 276 761. However, the light stability properties of oxidation hair colors obtainable with resorcinol are only moderate. m-Phenylenediamine and m-tolylenediamine have also long been used as color modifiers.
DESCRIPTION OF THE INVENTION
However, these color modifiers do not provide natural brown tones with the usual primary intermediate components.
SUMMARY OF THE INVENTION
It has now been found that 1,3-disubstituted nitrobenzenes corresponding to general formula I: ##STR2## in which X is a hydroxyl group or an amino group and R.sup.1 is hydrogen or a C.sub.1-4 alkyl group, and salts thereof are suitable as color modifiers together with known primary intermediate compounds for producing intensive oxidation colors.
The oxidation colors obtainable in this way are readily absorbed by hair and other keratin fibers and show high stability to light and heat.
DESCRIPTION OF PREFERRED EMBODIMENTS
Accordingly, the present invention also relates to hair dyes containing oxidation dye precursors in a carrier, 1,3-disubstituted nitrobenzenes corresponding to formula I or salts thereof as color modifiers and one or more primary intermediate components typically encountered in oxidation dyes being present as the oxidation dye precursors.
The 1,3-disubstituted nitrobenzenes corresponding to general formula I are compounds known from the literature or may be synthesized by methods known from the literature. 2-Nitroresorcinol is described, for example, in J. Org. Chem. 16 (1951), 611 while 2-nitro-m-phenylene diamine is described in J. Chem. Soc. Perkin Trans. I (1988), 1940-1941. They are suitable as color modifiers for a number of known primary intermediate compounds and produce intensive colors in the form of brown tones. Suitable primary intermediate components are, for example, aromatic amines or phenols containing one or more other NH.sub.2 groups, NHR groups or N
REFERENCES:
patent: 4330291 (1982-05-01), Bugaut et al.
patent: 4473374 (1984-09-01), Bugaut et al.
patent: 4797129 (1989-01-01), Junino et al.
Jounal of Organic Chemistry, vol. 16, 1951, p. 611.
J. Chem. Soc. Perkin Trans. I, 1988, pp. 1940-1941.
Hoeffkes Horst
Lieske Edgar
Rose David
Henkel Kommanditgelsellschaft auf Aktien
Jaeschke Wayne C.
Lieberman Paul
Parks William S.
Szoke Ernest G.
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