Substituted 1,4-diaminobenzene compounds and oxidation dye precursor compositions containing same
AssigneeWella Aktiengesellschaft
InventorsLaurent Chassot, Hans-Juergen Braun
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AssigneeWella Aktiengesellschaft
InventorsLaurent Chassot, Hans-Juergen Braun
Estimating the term…
New substituted 2,5-diamino-1-aminomethylbenzene compounds of formula (I), or physiologically compatible water-soluble salts thereof, are described as well as methods for preparing them. In addition, oxidation dye precursor compositions for dyeing keratin fibers, especially human hair, which each contain from 0.005 to 20 percent by weight of at least one of the new substituted 2,5-diamino-1-aminomethylbenzene compounds of formula (I), or their physiologically compatible water-soluble salts, are described. Methods for dyeing hair with ready-to-apply dye mixtures made by mixing these oxidation dye precursor compositions with an oxidizing agent, such as hydrogen peroxide solution, are also described.
A substituted 2,5-diamino-1-aminomethylbenzene compound of formula (I), or a physiologically compatible water-soluble salt thereof,
A substituted 2,5-diamino-1-aminomethylbenzene compound selected from the group consisting of 2-((2-amino-phenylamino)-methyl)-1,4-diaminobenzene;
An oxidation dye precursor composition for dyeing keratin fibers, said oxidation dye precursor composition containing at least one substituted 2,5-diamino-1-aminomethylbenzene compound of formula (I), or a physiologically compatible water-soluble salt thereof,
Dependencies are inferred from the claim text.
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Amines: aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
Preparations for care of the hair: preparations for permanently dyeing the hair
With at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton: phenylenediamines
Compounds containing amino and hydroxy groups bound to the same carbon skeleton: having amino groups bound to carbon atoms of six-membered…
Term ended 3 Nov 2020 (estimated)
1. Field of the Invention
The present invention relates to new substituted 2,5-diamino-1-aminomethylbenzene compounds and oxidation dye precursor compositions for dyeing keratin fibers, especially human hair, containing these compounds.
2. Prior Art
A. Synthesis of 2,5-bis-tert.-butyloxycarbonylaminobromobenzene
15.65 g (0.07 mol) bromo-p-phenylenediamine hydrochloride and 32.7 g (0.15 mol) di-tert-butyl dicarbonate are dissolved in a mixture of 250 ml 2N sodium hydroxide solution and 250 ml trifluorotoluene and the mixture is heated at 45° C. The reaction mixture is stirred for 3 days. Additional 30 g (0.14 mol) di-tert.-butyl dicarbonate are added gradually.
Subsequently the organic layer is separated and the aqueous phase is extracted twice with 100 ml of dichloromethane. The combined extracts are evaporated to form a residue and the residue is taken up in 200 ml of hexane The precipitate is separated by filtration and washed with 50 ml hexane. 18.6 g (82% of theoretical) of 2,5-bis-tert.-butyloxycarbonylaminobromobenzene were obtained with a melting point of 130° C.