4-(2,4-diaminophenoxymethyl)-1,3-dioxolane secondary intermediat

Details 4-(2,4-diaminophenoxymethyl)-1,3-dioxolane secondary intermediat 4-(2,4-diaminophenoxymethyl)-1,3-dioxolane secondary intermediat

1998-05-13

1999-10-05

Liott, Caroline D.

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

8406, 8416, 8423, 8576, 8618, 8624, 549451, A61K 713, C07D31700

Patent

active

059616687

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

This invention relates to new substituted 4-(2,4-diaminophenoxymethyl)-1,3-dioxolanes corresponding to general formula (I): ##STR2## to processes for their production and to their use as hair colorants.
So-called oxidation dyes are used for coloring keratin fibers because they ultimately provide extremely fast intensive colors. Under boundary in-use conditions (low coloring temperature, short coloring time), they give fast, intensive colors. The actual dyes are formed by the oxidative coupling of a primary intermediate and a secondary intermediate during the coloring process. Numerous primary and secondary intermediates for obtaining various color tones, hereinafter referred to as hair dye intermediates, are described in the literature (K. Venkataraman, The Chemistry of Synthetic Dyes, Vol. V, Academic Press, 1971; F. Brody and M. S. Burns, J. Soc. Cosmet. Chem. 19, 361-379, 1968; H. Husemeyer, J. Soc. Cosmet. Chem. 25, 131-138, 1974).
Although in principle the oxidative coupling reaction, i.e. development of the color, can be carried out with atmospheric oxygen, it is generally too slow and/or provides uneven coloring results, so that chemical oxidizing agents are normally used. Preferred oxidizing agents are based on hydrogen peroxide and, besides hydrogen peroxide itself, on addition compounds thereof with urea, melamine or alkali metal perborate.
The use of 1-alkoxysubstituted 2,4-diaminobenzene derivatives as secondary intermediates is well known from the literature. Thus, DE-PS 38 06 237 and DE-OS 32 44 517 describe substituted 2,4-diaminoanisoles while DE-OS 27 37 138 describes substituted .beta.-hydroxy-2,4-diaminophenetols. The colors described therein produced an intensive blue color tone, but with a distinct red component which is visible in particular in lighter shades. Where it is desired to obtain natural shades combining adequate depth of color with an adequate grey-masking effect, the red component is a disadvantage. Accordingly, there was an urgent need to develop new secondary intermediates which would give intensive colors in the clear blue range. It has now surprisingly been found that the compounds of general formula (I) described in the present invention satisfy this requirement particularly effectively.


DESCRIPTION OF THE INVENTION

Accordingly, the present invention relates to the use of compounds corresponding to formula (I): ##STR3## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another may represent a hydrogen atom, a (C.sub.1-4) alkyl group, a hydroxy (C.sub.2-3) alkyl group, an alkoxy (C.sub.2-3) alkyl group, an amino (C.sub.2-3) alkyl group or a 2,3-dihydroxypropyl group and R.sub.5 and R.sub.6 independently of one another may represent hydrogen or a (C.sub.1-4) alkyl group, to processes for their production and to salts thereof with inorganic or organic acids.
The secondary intermediates according to the invention are prepared by reacting 2,4-dinitrohalobenzenes corresponding to formula (II), where X=flourine, chlorine, bromine or iodine, with 4-hydroxymethyl-1,3-dioxolanes corresponding to formula (III), where R.sub.5 and R.sub.6 are as defined above, in an alkaline reaction medium, optionally in the presence of phase transfer catalysts, to form 4-(2,4-dinitrophenoxymethyl)-1,3-dioxolanes corresponding to formula (IV) and reducing the compounds (IV) to form the compounds of formula (I) according to the invention: ##STR4##
The compounds corresponding to formula (III) are already known and may be obtained by reaction of glycerol with carbonyl compounds (see, for example, E. Fischer, Ber. Dtsch. Chem. Ges. 28 1169 (1895); H. S. Hill, E. C. Hill and H. Hibbert, J. A. Chem. Soc. 50, 2246 (1928); M. S. Newman and M. Renoll, ibid 67, 1621 (1945)).
In another process, the secondary intermediates corresponding to formula (I) may be obtained by reacting 4-halo-3-nitranilines or 2-halo-5-nitranilines with 4-hydroxymethyl-1,3-dioxolanes in a first step to form a compound corresponding to formula (Va): ##STR5## or formula (Vb): ##STR6#

REFERENCES:
patent: 2769808 (1956-11-01), Tenebaum
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Chemical Abstracts vol. 113, No. 21, Abs. No. 191208H, p. 710 (1990).
Chemistry of Synthetic Dyes, vol. V, Chap. VIII, pp. 475-533 (1971).
J. Soc. Cosmet. Chem 19: 361-79 (May 1968), Brody et al.
J. Soc. Cosmet. Chem 25: 131-138, Husemeyer (Mar. 1974).
Ber Dtsch. Chem. Ges. 28: 1167-1170 (1895).
J. Am. Chem Soc. 50: 2242-2249, Hill et al (Aug. 1928).
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