Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Patent
1988-08-24
1990-05-08
Lieberman, Paul
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
8407, 8408, 8421, 564442, 564443, A61K 713, C07C 8760
Patent
active
049234790
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to an agent and a process for the oxidative dyeing of hair based on a combination of a developer substance and a coupling substance, wherein a 3-(2',2',2'-trifluorethyl)aminophenol derivative is used as well as to the novel 3,-(2',2',2'-trifluoroethyl)aminophenol derivatives per se.
In hair dyeing practice oxidation dyes have gained substantial importance. In oxidative dyeing the dyes are produced by oxidative coupling of developer substances and coupling substances in the hair shaft. This results in very intensive hair colorations with very good color fastness. Furthermore, different color shades can be produced by the combination of suitable developer substances and coupling substances.
Usually 1,4-diamino-benzene, 2,5-diamino toluene, 2,5-diamino-anisole and 4-aminophenol are used as developer substances. 2,5-diamino-benzyl alcohol and 2-(2',5'-diamino) phenyl-ethanol have also gained some importance.
These developer substances together with suitable coupling substances under the action of an oxidizing agent result in the hair colorations. Thus, for example, with the coupling substances resorcinol, 2-methyl resorcinol or 4-chloro resorcinol natural blond to light brown hair colors are obtained.
By combining the developer substances 1,4-diamino-benzene or 4-aminophenol with the coupling substances 5-amino-2-methylphenol and 1,3-diamino-benzene derivatives such as 2,4-diamino-anisole red hair colors can also be obtained.
Blue to blue-violet color shades are produced with 1,4-diamino-benzene or its derivatives, as for example, 2,5-diamino-toluene, or developer substance, requiring the use of 1,3-diamino-benzene derivatives as coupling substances.
Black hair colors can be obtained by combining the above-mentioned developer substances and coupling substances with further suitable coupling substances. However, the 1,3-diamino-benzene derivatives are considered to be toxicologically objectionable so there exists a need of a substitute for these substances in a hair dye.
Several attempts have been made to replace the 1,3-diamino-benzene derivatives by the 3-aminophenol derivatives, which are generaly regarded as being toxicologically more suitable. However, with the conventional coupling substances 3-aminophenol and 5-amino-2-methylphenol only red hair colors can be produced. Furthermore, with the coupling substance described in DE-OS 2,429,780, i.e., 5-amino-2-aminophenol, in combination with the developer substance 2,5-aminophenol a reddish violet shade is obtained. Therefore, the 5-amino-2-chlorophenol is not completely suitable as a substitute for 1,3-diamino-benzene.
Therefore, the present invention provides a hair dye based on a combination of a developer substance and a coupling substance, wherein the coupling substance is toxicologically more favorable than 1,3-diamino-benzene and has better dyeing properties than the conventional 3-aminophenol derivatives.
It has now been found that an agent for the oxidative dyeing of hair based on a combination of developer substance and coupling substance which contains as coupling substance a 3-(2',2',2'-trifluoro-ethyl)aminophenol derivative having the formula I ##STR2## wherein the radical R represents an alkyl radical containing 1 to 4 carbon atoms, a mono- or polyhydroxy-alkyl radical containing 1 to 4 carbon atoms and up to 3 hydroxyl groups, an alkoxy radical containing 1 to 4 carbon atoms, a mono- or polyhydroxy alkoxy radical containing 1 to 4 carbon atoms and up to 3 hydroxyl groups or a halogen atom or its physiologically compatible salt, is excellent for this purpose.
The radical R in the formula (I) can be in an ortho, meta or para position relative to the (2',2',2'-trifluoroethyl) amino radical, the para position relative to the (2',2',2'-trifluoroethyl)radical being preferred. Chlorine is preferred as the halogen atom.
As physiologically compatible salt with inorganic or organic acids, for example, the chloride, the sulphate, the phosphate, the acetate, the propionate, the lactate and the citrate may be mentioned.
As comp
REFERENCES:
patent: 3811831 (1974-05-01), Bugaut et al.
patent: 4395262 (1983-07-01), Konrad et al.
patent: 4543425 (1985-09-01), Konrad et al.
"Synthesis of Some Trifluoroethyl-Substituted Derivatives of Aniline", by Eugene R. Bissell and Rosalind W. Swansiger; Journal of Fluorine Chemistry, 12 (1978), pp. 293-305.
Lieberman Paul
Skaling Linda A.
Striker Michael J.
Wella Aktiengesellschaft
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