Coupler for use in oxidative hair dyeing

Details Coupler for use in oxidative hair dyeing Coupler for use in oxidative hair dyeing

2001-11-16

2004-01-06

Hardee, John (Department: 1751)

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

Organic compounds

Amino nitrogen containing

Reexamination Certificate

active

06673966

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to novel couplers for use in hair coloring compositions comprising one or more oxidative hair coloring agents in combination with one or more oxidizing agents. The invention also relates to hair coloring compositions of these novel couplers and to coloring or dyeing of hair using compositions containing these couplers.
BACKGROUND OF THE INVENTION
Coloration of hair is a procedure practiced from antiquity employing a variety of means. In modern times, the most extensively used method employed to color hair is to color hair by an oxidative dyeing process employing hair coloring systems utilizing one or more oxidative hair coloring agents in combination with one or more oxidizing agents.
Most commonly a peroxy oxidizing agent is used in combination with one or more oxidative hair coloring agents, generally small molecules capable of diffusing into hair and comprising one or more primary intermediates and one or more couplers. In this procedure, a peroxide material, such as hydrogen peroxide, is employed to activate the small molecules of primary intermediates so that they react with couplers to form larger sized compounds in the hair shaft to color the hair in a variety of shades and colors.
A wide variety of primary intermediates and couplers have been employed in such oxidative hair coloring systems and compositions. Among the primary intermediates employed there may be mentioned p-phenylenediamine, p-toluenediamine, p-aminophenol, 4-amino-3-methylphenol, and as couplers there may be mentioned resorcinol, 2-methylresorcinol, 3-aminophenol, and 5-amino-2-methylphenol. A majority of the shades have been produced with dyes based on p-phenylenediamine.
DE 4422603 describes oxidative hair dyes based on 4,5-diamininopyrazoles and m-phenylenediamine derivatives. Especially (3-dimethylamino-phenyl)-urea couples with 4,5-diaminopyrazole to provide a blue color. However, the intensity of the blue is not very strong probably due to the solubility of the compound. Therefore, there is a need for new couplers for use in oxidative hair dyeing compositions and systems to increase dye-uptake, resulting in strong blue coloration.
BRIEF SUMMARY OF THE INVENTION
This invention provides novel couplers of the formula (1):
wherein X is selected from halogen and R
5
SO
4
where the halogen is preferably Cl, Br or I; R, R
1
, R
2
and R
5
are each individually selected from C
1
to C
22
alkyl and C
1
to C
22
mono or dihydroxyalkyl and R
3
and R
4
are each individually selected from C
1
to C
6
alkyl, C
1
to C
6
hydroxyalkyl, C
1
to C
6
alkoxy, C
1
to C
6
aminoalkyl or R
3
and R
4
together form a C
1
to C
5
alkylene group. Preferably X is Cl, Br, I and R
5
SO
4
where R
5
is C
1
to C
4
alkyl, more preferably methyl; and preferably R, R
1
, R
2
, R
3
and R
4
are each individually C
1
to C
4
alkyl, and more preferably methyl. These novel couplers are used to provide coloration to hair in which there is good dye uptake by the hair and provides shades or colors which are stable over a relatively long period of time. The novel couplers provide for dyeing of hair that provides color or shades that possess good wash fastness and do not undergo the significant changes on exposure to light or shampooing.
DETAILED DESCRIPTION OF THE INVENTION
Preferred coupler compounds of this invention are those of formula (1)
wherein X is selected from Cl, Br I and R
5
SO
4
where R
5
is C
1
to C
3
alkyl; and R, R
1
, R
2
, and R
5
are each individually a C
1
to C
3
alkyl group, preferably methyl groups; and R
3
and R
4
are individually selected from C
1
to C
3
alkyl groups, preferably methyl groups.
Especially preferred couplers of this invention are the following compounds:
quatererized N-[2-(trimethylamino)ethyl]N′-[3-(dimethylamino)phenyl]urea iodide, chloride, bromide and methyl sulfate salts;
The novel coupler compounds of formula (1) of this invention are readily prepared according to the following reaction sequence where X, R, R
1
, R
2
, R3, R
4
and R
5
are as defined hereinbefore:
As a example of such synthesis an aminobenzoic acid of formula (2) is subjected to a Curtius rearrngement with diphenylphosphoryl azide (DPPA) and triethylamine (Et
3
N) in toluene to give the isocyanate of formula (3). Reaction of this isocyanate with a disubstituted ethylene diamine (H
2
N—CH
2
—CH
2
—N—R
1
,R
2
) produces the urea compound of formula (4). Reaction of this urea compound with the quaternization reagent R-X produces the quaternized urea compounds of formula (1).


REFERENCES:
patent: 4065255 (1977-12-01), Andrillon et al.
patent: 2101999 (1972-08-01), None
patent: 0 667 143 (1996-10-01), None
patent: 0 634 165 (1997-09-01), None

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