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

2003-06-03

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S405000, C008S406000, C008S410000, C008S412000, C008S421000, C546S249000, C546S329000, C546S334000

Reexamination Certificate

active

06572665

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 complunds 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.
For providing an orange coloration to hair 2-methyl-5-aminophenol has been extensively used in combination with p-aminophenol as a primary intermediate. However, the resulting orange color on hair undergoes significant changes on exposure to light or shampooing. U.S. Pat. No. 4,065,255 and EP patent publications EP 634165 A1 and EP 667143 A1 suggest the use of 2-methyl-5-N-hydroxyethylaminophenol, 2-methyl-5-alkylaminophenol and 2-methyl-5-aminophenol as couplers. Therefore, there is a need for new orange couplers for use in oxidative hair dyeing compositions and systems.
BRIEF SUMMARY OF THE INVENTION
This invention provides novel couplers of formula (1):
wherein X is selected from halogen or R
2
SO
4
, where the halogen is preferably Cl, Br or I; R
3
is selected from C
1
to C
2
alkyl and hydroxyethyl; R
2
is selected from C
1
to C
22
alkyl or C
1
to C
22
mono or dihydroxyalkyl; and R is selected from C
1
to C
16
alkyl, C
1
to C
10
hydroxyalkyl, C
1
to C
6
alkoxyalkyl and benzyl. 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 as experienced with 2-methyl-5-aminophenol.
DETAILED DESCRIPTION OF THE INVENTION
Preferred coupler compounds of this invention are of formula (1)
wherein R
3
is a methyl group; R is C
1
to C
3
alkyl, most preferably methyl, C
1
to C
3
hydroxyalkyl, C
1
to C
4
alkoxyalkyl and benzyl; and X is selected from Cl, Br, and R
2
SO
4
where R
2
is C
1
to C
3
alkyl.
Especially preferred couplers of this invention are the following compounds:
3-[(3-hydroxy-4-methyl-phenylamino)-methyl]-1-methyl-pyridinium iodide;
3-[(3-hydroxy-4-methyl-phenylamino)-methyl]-1-benzyl-pyridinium chloride;
3-[(3-hydroxy-4-methyl-phenylamino)-methyl]-1-ethoxyethyl-pyridinium chloride;
3-[(3-hydroxy-4-ethyl-phenylamino)-methyl]-1-methyl-pyridinium chloride;
3-[(3-hydroxy-4-ethyl-phenylamino)-methyl]-1-ethyl-pyridinium chloride;
3-[(3-hydroxy-4-hydroxyethyl-phenylamino)-methyl]-1-methyl-pyridinium chloride;
3-[(3-hydroxy-4-methyl-phenylamino)-methyl]-1-methyl-pyridinium bromide;
3-[(3-hydroxy-4-methyl-phenylamino)-methyl]-1-methyl-pyridinium methyl sulfate; and
3-[(3-hydroxy-4-hydroxyethyl-phenylamino)-methyl]-1-methyl-pyridinium propyl sulfate.
The novel coupler compounds of formula (1) of this invention are readily prepared according to the following reaction sequence:
In the reaction sequence reductive amination reaction of an aminophenol of formula (2) with an appropriate pyridine carboxaldehyde of formula (3) in the presence of a suitable reducing agent, such as sodium triacetoxyborohydride or sodium borohydride in 1% acetic acid in 1,2-dichloroethane, produces compound (4). Compound (4) is treated with a suitable blocking or protecting agent, such as di-t-butyl dicarbonate (Boc
2
O) to produce compound (5) which is reacted with quaternization reagent R-X, such as methyl iodide, to result in the formation of compound (6). Deprotection of compound (6) by treatment with an acid, such as HCl, produces a compound of formula (1) of the invention.


REFERENCES:
patent: 4065255 (1977-12-01), Andrillon et al.
patent: 6383230 (2002-05-01), Genet et al.
patent: 0 667 143 (1996-10-01), None
patent: 0 634 165 (1997-09-01), None

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