Hydroxyethylated 2-nitro-p-phenylenediamines and use thereof for

Details Hydroxyethylated 2-nitro-p-phenylenediamines and use thereof for Hydroxyethylated 2-nitro-p-phenylenediamines and use thereof for

1994-12-07

1996-05-14

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

8415, A61K 713, C07C21516

Patent

active

055169422

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of application PCT/FR93/00571, filed Jun. 15, 1993.
The present invention relates to novel nitrobenzene dyes of 2-nitro-p-phenylenediamine type, which are intended for dyeing keratin fibers and in particular human hair.
In the field of hair dyeing, the use of direct dyes is very widespread since they have certain advantages with respect to oxidation dye precursors and, in particular, a reduction in the potential risks of allergy and the absence of sensitization of the hair caused by the oxidative process.
Nitrobenzene derivatives feature among the most commonly used direct dyes, which derivatives, on the one hand, have a high affinity for hair, and which, on the other hand, due to the variety of possible substitutes, make it possible to cover a wide spectrum of shades ranging from yellow to blue and including red.
Among the blue or blue-purple nitro dyes used, there may be mentioned 1-.beta.-hydroxyethylamino-4-N,N-bis(.beta.-hydroxyethyl)amino-2-nitrobenz ene described in French Patent 1 101 904, 1-.beta.-hydroxyethylamino-4-(N-methyl-N-.beta.-hydroxyethyl)amino-2-nitro benzene described in Canadian Patent 900 490, and 1-.beta.-hydroxy-ethylamino-4-(N-ethyl-N-.beta.-hydroxyethyl)amino-2-nitro benzene described in Patent EP-0 184 061.
However, the formulation of these nitro dyes poses problems on account of their resistance to washing, which is not satisfactory.
The Applicant has thus sought other nitrobenzene dyes which have shades graduating from blue to purple and which have good solubility in water, in water/alcohol mixtures and more generally in the usual dye supports, and which lead, on hair, to dyes which are wash-fast and light-fast, weatherproof and sweat-resistant.
As a result of this research, the Applicant has discovered novel 2-nitro-p-phenylenediamines having the formula: ##STR1## in which R represents a linear or branched alkyl radical containing 3 or 4 carbon atoms.
Among the alkyl radicals R, there may be mentioned n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl radicals, the preferred radicals being n-propyl and isobutyl.
The compounds of formula (I) may be used in free base form or in the form of a base salified with acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, etc. They may thus be found in the form of a hydrochloride, a hydrobromide, a sulfate, etc.
The present invention thus relates to the novel compounds of formula (I) and to the cosmetically acceptable salts thereof.
The compounds of formula (I) are prepared by a standard alkylation process which consists in reacting, in an aqueous medium and at a temperature between room temperature and the reflux temperature of the medium, 1,4-di(.beta.-hydroxyethylamino)-2-nitrobenzene with a haloalkane such as a bromo-, iodo- or chloroalkane, in the presence of calcium carbonate, optionally followed by purification of the compound obtained.
The invention also relates to a dye composition for the direct dyeing of keratin fibers and in particular human hair, which composition contains, in an aqueous, alcoholic or aqueous-alcoholic vehicle, at least one compound of formula (I) or one of the cosmetically acceptable salts thereof.
The Applicant has observed that the combination of a blue to purple nitrobenzene dye of formula (I), in compositions for direct dyeing, with yellow or green-yellow dyes and optionally with orange or red dyes, leads to the production of natural shades which are wash-fast, light-fast, weatherproof and sweat-resistant.
In a preferred embodiment, the dye composition according to the invention thus contains a compound of formula (I), or one of the cosmetically acceptable salts thereof, in combination with one or more yellow or green-yellow nitrobenzene dyes, which give, on gray hair containing 90% white hairs, a shade or "hue" of between 2.5 Y and 2.5 GY on the Munsell circle (see Official Digest publication, April 1975, page 375, figure 2).
In a more particularly preferred embodiment of the present invention, the compound of formula (I) is combined with yellow or green-yellow

REFERENCES:
patent: 3555584 (1971-01-01), Kalopissi et al.
patent: 4007228 (1977-02-01), Kalopissi et al.
patent: 4921504 (1990-05-01), Clausen et al.

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