Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1998-11-03
2001-05-08
Travers, Russell (Department: 1618)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S405000, C008S407000, C008S408000, C008S409000, C008S410000, C008S411000, C564S306000, C564S418000
Reexamination Certificate
active
06228130
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to 1-(2,5-diaminophenyl)ethylene glycol (1), to a process for preparing same and to its use in compositions for dyeing human hair.
BACKGROUND OF THE INVENTION
Compositions for the oxidative dyeing of hair comprise primary intermediates (such as p-phenylenediamine, p-toluenediamine, p-aminophenol, 4-amino-3-methylphenol) and couplers (such as resorcinol, 2-methylresorcinol, 3-aminophenol, 5-amino-2-methylphenol). A majority of shades have been produced with dyes based on p-phenylenediamine. However, as noted in U.S. Pat. Nos. 5,599,353 and 5,538,516, the use of p-phenylenediamine is being questioned for toxicological reasons, mainly due to its sensitization potential.
Because of the supposed toxicological issues attendant to its use, the art has been looking for substitutes for p-phenylenediamine.
EP 400,330 B1 (GB 2,239,265 A) describes the use of 2-(2-hydroxyethyl)-p-phenylenediamine as a replacement for p-phenylenediamine.
Pyrimidine derivatives, such as tetraaminopyrimidine, have been also suggested as alternatives to p-phenylenediamine (see U.S. Pat. No. Re. 30,199 [U.S. Pat. No. 4,003,699]). However, GB 2,239,265 A, points out that although the use of pyrimidine derivatives as developers has reduced toxicological problems, the pyrimidine derivatives are not completely satisfactory with respect to coloring performance.
U.S. Pat. No. 5,421,833 discloses hair dye compositions asserted to be without sensitizing potential. The dye compositions are disclosed to possess improved dyeing properties for all shades. The compositions comprise only 2-(2′-hydroxyethyl)amino-5-aminotoluene in combination with the usual coupling agents (with the exclusion of 1-methoxy-2,4-diaminobenzene and 1-ethoxy-2,4-diaminobenzene).
The object of the present invention was to develop a p-phenylenediamine alternative having less sensitization potential. This proved to be a difficult task. Since the structure-sensitization relationship is not known, it is difficult to predict whether a hair dye molecule will exhibit much lower potential for sensitization than p-phenylenediamine. Surprisingly and unexpectedly, we have found that 1-(2,5-diaminophenyl)ethylene glycol is a much weaker sensitizer than p-phenylenediamine.
SUMMARY OF THE INVENTION
The present invention provides the novel compound, 1-(2,5-diaminophenyl)ethylene glycol, a process for preparing same, its use as a primary intermediate in oxidative hair dyeing, and hair dye compositions containing same.
In contrast to p-phenylenediamine, 1-(2,5-diaminophenyl)ethylene glycol was surprisingly found to be a weak sensitizer.
Current technology generally requires p-phenylenediamine or p-toluenediamine for producing red and black shades (see U.S. Pat. No. 5,538,516).
The present invention enables one skilled in the art to formulate a natural black shade and dark red shade through the use of 1-(2,5-diaminophenyl)ethylene glycol without relying on p-phenylenediamine (see Table 2).
Advantageously, the shades obtained through use of 1-(2,5-diaminophenyl)ethylene glycol have good wash and light fastness.
The process for the preparation of the 1-(2,5-diaminophenyl)ethylene glycol is new and commercially feasible. The synthesis of the compound
1
requires three steps: (1) ring-opening of 5-nitroisatin with sodium hydroxide, (2) borane reduction of the keto acid, and (3) hydrogenation.
1-(2,5-Diaminophenyl)ethylene glycol has excellent solubility in water. Four grams of 1-(2,5-diaminophenyl)ethylene glycol sulfate salt completely dissolves in 100 ml of water at room temperature. The p-toluenediamine sulfate salt is partially soluble under the same conditions. Water solubility is important because hair dye formulations employed for hair coloring are in large part water.
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Lim Mu'Ill
Pan Yuh-Guo
Stasaitis Linas R.
Wong Michael Y. M.
Bristol--Myers Squibb Company
Travers Russell
Wang Shengjun
Zeller Charles J.
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