Couplers for use in oxidative hair dyeing

Details Couplers for use in oxidative hair dyeing Couplers for use in oxidative hair dyeing

2002-01-18

2004-06-15

Raymond, Richard L. (Department: 1624)

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

Organic compounds

Chalcogen in the nitrogen containing substituent

C544S108000, C546S186000, C546S194000, C546S208000, C546S229000, C548S517000, C548S577000, C548S578000, C548S950000, C548S954000, C564S287000

Reexamination Certificate

active

06750337

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.
Recently, 2-(4,5-diamino-1H-pyrazol-1-yl)ethanol has been extensively used for providing fashionable red coloration. This primary intermediate couples with conventional couplers to produce a coloration ranging from orange to red. Due to the limitation of color range derived from the pyrazole, there is need to develop a coupler or couplers to generate 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
, and R
2
are each individually selected from C
1
to C
22
alkyl and C
1
to C
22
mono or dihydroxyalkyl, or two of R, R
1
and R
2
together with the nitrogen atom to which they are attached form a C
3
to C
6
, preferably C
4
to C
6
, saturated or unsaturated ring optionally containing in the ring one or more additional hetero atoms selected from O, S and N atoms; 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
2
to C
5
alkylene group; and R
5
is selected from C
1
to C
22
alkyl and C
1
to C
22
mono or dihydroxyalkyl. 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
3
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 to impart color or shades that possess good wash fastness, good selectivity and do not undergo significant changes on exposure to light, perspiration or shampooing.
DETAILED DESCRIPTION OF THE INVENTION
The coupler compounds of this invention are those of 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
, and R
2
are each individually selected from C
1
to C
22
alkyl and C
1
to C
22
mono or dihydroxyalkyl, or two of R, R
1
and R
2
together with the nitrogen atom to which they are attached form a C
3
to C
6
, preferably C
4
to C
6
, saturated or unsaturated ring optionally containing in the ring one or more additional hetero atoms selected from O, S and N atoms; 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
2
to C
5
alkylene group; and R
5
is selected from C
1
to C
22
alkyl and C
1
to C
22
mono or dihydroxyalkyl. 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
3
alkyl, and more preferably methyl.
Preferably X is selected from Cl, Br I and R
5
SO
4
where R
5
is C
1
to C
3
alkyl, preferably a methyl group; R, R
1
, and R
2
are each individually selected from a C
1
to C
3
alkyl group, preferably methyl groups; a piperazinium or imidazolium group 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: [2-(3-dimethylamino-phenoxy)-ethyl]-trimethyl-ammonium; bromide; 1-[2-(3-dimethylamino-phenoxy)-ethyl]-1,4-dimethyl-piperazin-1-ium; bromide; and 1-[2-(3-dimethylamino-phenoxy)-ethyl]-3-methyl-3H-imidazol-1-ium; bromide.
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
, R
3
, R
4
and R
5
are as defined hereinbefore:
In this synthesis an aminophenol (2) is reacted with a 2-haloethanol, such as 2-bromoethanol, in the presence of potassium carbonate in dimethylformarnide to produce the alcohol compound (3). Transformation of this alcohol compound (3) into a compound (4) is carried out by treatment of the alcohol compound with triphenylphosphine and a halo-succinimide, such as bromosuccinimide (NBS). Treatment of compound (4) with a quaternization reagent (NRR
1
R
2
) produces a compounds of formula (1) of this invention.


REFERENCES:
patent: 3755287 (1973-08-01), Hegar et al.
patent: 5919608 (1999-07-01), Haque et al.
Coleman et al, “Nicotine-Like Stimulant Actions of Several Substituted Phenylcholine Ethers” The Journal of Pharmacology and Experimental Therapeutics, vol. 148(1), pp. 66-70 (1965).*
Organic Chemistry, Paula Yurkanis Bruice, © 1995 Prentice Hall, pp. 588-591.

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