Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Patent
1983-07-18
1986-05-13
Warren, Charles F.
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
8405, 8406, 564413, 564418, 564443, 564441, A61K 713, C07L 9140
Patent
active
045884102
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The subject invention relates to novel 2-hydroxy-4-aminobenzenes of the general formula ##STR2## wherein R is a hydrogen atom, a methyl group or a hydroxyethyl group.
The subject invention relates also to the salts formed by the compounds of the general formula with anorganic or organic acids like, the hydrochlorides, hydrobromides or sulfates or the corresponding phenolates.
SUMMARY OF THE INVENTION
The novel compounds in accordance with the invention are produced based on a 4-nitro-1,2-methylene dioxybenzene, in that it is heated in a solution of sodium in dry ethyl glycol (a), or diethyl glycol (b), or 2-methoxyethanol (c) for a few hours, in particular for 3 hours, to a temperature of 120.degree. C., the generated solution is then absorbed in water after cooling, then it is filtered, the filtrate is acidified and the precipitated purified 2-hydroxy-4-nitrobenzene derivative of the formula ##STR3## wherein R is a hydrogen atom, a methyl group or a hydroxyethyl group which is hydrated in the presence of a catalyst, preferably palladium in a known manner to 1-(2'-hydroxyethoxy)-2-hydroxy-4-aminobenzenes (a), or 1-(hydroxy-bis-ethoxy)-2-hydroxy-4-aminobenzenes (b), or 1-(2'-methoxy-ethoxy)-2-hydroxy-4-aminobenzenes (c).
The novel compounds in accordance with the invention represent oxidative color preliminary steps which are very well suited for coloring hair.
The so-called oxydation colors for coloring hair which are created by an oxidative coupling of a developer component with a coupler component play a preferred role because of their intensive colors and their very good fast characteristics. Customarily, 2,5-diaminotoluene, 4-aminophenol and the 1,4-diaminotoluene are used as the developer substances; however 2,5-diaminotoluene, 3-methyl-4-aminophenol, 2,5-diaminobenzylalcohol and 2(.beta.-hydroxyethyl)-1,4-diaminotoluene have attained a certain importance. Also, the tetraaminopyrimidin may be used as a developer.
Resorcin, 4-chlorresorcin, m-aminophenol, 5-amino-2-methylhenol, 1-naphthol as well as derivatives of the m-phenyldiamine, for example, 2-amino-4-(.beta.-hydroxyethylamino)anisole or 2,4-diaminophenoxyethanol are known as preferably used coupler substances.
A number of particular requirements are made with respect to oxydation colors which are used for coloring human hair. From the toxicological and the dermatological point of view they must be unobjectionable and enable the attainment of colorings in the desired intensity. Furthermore, it is a requirement that a wide spectrum of different color shades can be generated by combining suitable developers and coupler components. Furthermore, a good light, permanent, acid and friction fastness is required for the attainable hair colorings. In any case, such hair colorings must remain stable for at least 4-6 weeks without influence of light, chemical agents and friction.
Colors which can be directly absorbed by the hair are also of importance, besides the mentioned preliminary colors. With these directly absorbed colors, in particular aromatic nitrocolors, yellow, orange, red and violet colors are attained.
Preferably, resorcin and m-aminophenol as a coupler in conjunction with p-phenyldiamines or 2,5-diaminotoluene are used as a developer for generating natural color tones. The yellow coloring caused by resorcin is covered by adding m-aminophenol and in this manner the color tone is adjusted as a whole to a warmer color tone.
However, if one would like to create fashionable tones, the use of m-aminophenol is less suitable since it generates only a very weak color tone together with the p-aminopenol and does not result in a red tone but rather a violet tone with the customary p-diamines like, for example, the 2,5-diaminotoluene or the 2,5-diaminobenzene alcohol.
It is therefore an object of the invention to make available novel color effective compounds as coupler substances which substantially eliminate the disadvantages of the m-aminophenol and result in cooling agents which meet the requirements in an optimum mann
REFERENCES:
patent: 3052722 (1972-09-01), Ashley et al.
patent: 3834866 (1974-09-01), Pum
Braun Hans-Jurgen
Konrad Eugen
Mager Herbert
Sopp John A.
Striker Michael J.
Warren Charles F.
Wella Aktiengesellschaft
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