Hair dye composition

Details Hair dye composition Hair dye composition

2001-03-15

2003-04-15

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S405000, C008S406000, C008S409000, C008S426000

Reexamination Certificate

active

06547834

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a hair dye composition featuring markedly high dyeing power, less color fade over time and a smaller color tone change of the dye even after storage.
BACKGROUND ART
Hair dyes can be classified by the dye to be used therefor, or whether they have bleaching action of melanin or not. Typical examples include a two-part permanent hair dye composed of a first part containing an alkali agent, an oxidation dye and a direct dye such as nitro dye and a second part containing an oxidizing agent; and one-part semi-permanent hair dye containing an organic acid or an alkali agent, and a direct dye such as acid dye, basic dye or nitro dye.
The above-described permanent hair dye is however accompanied with the drawbacks that color tone imparted by an oxidation dye is not so vivid and the color of the hair dyed with a vivid-color producing nitro dye ordinarily employed as a direct dye markedly fades over time and becomes dull soon even if the color tone rightly after dyeing is very vivid (Japanese Patent Application Laid-Open (Kokai) No. Hei 6-271435).
Recently, hair dyes containing as a direct dye a so-called cationic dye having a cation group contained in their conjugate system have been reported (Japanese Language Laid-Open Publication (PCT) No. Hei 8-507545, 8-501322 or 10-502946, or Japanese Patent Application Laid-Open (Kokai) No. Hei 10-194942). They have been found to involve drawbacks that intended dyeing effects are not available owing to decomposition of them caused by mixing, upon hair dyeing, with hydrogen peroxide ordinarily employed as an oxidizing agent; and that when the cation group is incorporated in an azo(—N═N)-based conjugated system, they are unstable to an alkali agent or a reducing agent essentially contained in a permanent hair dye.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a hair dye composition featuring high hair dyeing power, less color fade over time and excellent storage stability to permit only a smaller color tone change of the dye after storage.
The present inventors have found that a hair composition containing a cationic dye represented by the below-described formula (1) which is disclosed as a dye for dyeing or printing fiber materials therewith in Japanese Patent Application Laid-Open (Kokai) No. Hei 7-166079, Japanese Patent Application Laid-Open (Kokai) No. Sho 54-111526, Japanese Patent Application Laid-Open (Kokai) No. Sho 49-10215, Japanese Patent Application Laid-Open (Kokai) No. Sho 48-923, Japanese Patent Application Laid-Open (Kokai) No. Sho 56-76457, Japanese Patent Application Laid-Open (Kokai) No. Sho 56-145952, Japanese Patent Application Laid-Open (Kokai) No. Hei 7-3177, U.S. Pat. No. 4,600,776, Japanese Patent Application Laid-Open (Kokai) No. Hei 9-12914, German Offenlegungsschrift DE-3149047, German Offenlegungsschrift DE-3205647, Japanese Patent Publication No. Sho 51-35405, Japanese Patent Publication No. Sho 49-4531, Japanese Patent Publication No. Sho 49-4530, Japanese Patent Application Laid-Open (Kokai) No. Sho 50-5683 or Japanese Patent Application Laid-Open (Kokai) No. Sho 54-149731; which is known as C.I. 48010, C.I. 48015 (Basic Red 13), C.I. 48020 (Basic Violet 7), C.I. 48030 (Basic Violet 21), C.I. 48035 (Basic Orange 21), C.I. 48040 (Basic Orange 22), C.I. 48055 (Basic Yellow 11), C.I. 48060 (Basic Yellow 21), C.I. 48065 (Basic Yellow 12), C.I. 48100 (Basic Yellow 23), C.I. 48016 (Basic Red 14) or C.I. 48056(Basic Yellow 13); or which is described in “Liebigs Ann. Chem. 107-121(1981)” can dye the hair with high dyeing power without causing decomposition of the dye upon hair dying, exhibits excellent light resistance, washing resistance, perspiration resistance, friction resistance and weather resistance, and causes a smaller change in color tone of the dye after storage as compared with that rightly after preparation because the dye exists in the composition stably.
In one aspect of the present invention, there is thus provided a hair dye composition comprising, as a direct dye, a compound represented by the following formula (1):
[wherein, R
1
and R
2
each independently represents a hydrogen atom or a C
1-6
alkyl group which may have a substituent,
A represent a group of the following formula (2):
(in which, R
3
, R
4
and R
5
each independently represents a C
1-6
alkyl group which may have a substituent, or R
4
and R
1
may be coupled together to form a cyclic structure, and benzene ring a
1
may have a substituent other than a sulfonic acid group or may be condensed with an aromatic ring), or a group of the following formula (3):
(in which, W represents an aralkyl group, a carbamoylalkyl group or a group —T—NR
6
R
7
(in which R
6
and R
7
each independently represents a C
1-6
alkyl group which may have a substituent, an aromatic group which may have a substituent or a heterocyclic group which may have a substituent, or R
6
and R
7
may form a heterocyclic ring together with the adjacent nitrogen atom, and T represents a divalent linear C
1-4
hydrocarbon group which may have a substituent), and pyridine ring a
2
may be condensed with an aromatic ring),
B represents a group represented by the formula —Z
1
, —NR
8
—Z
1
or —CH═Z
2
(in which Z
1
represents an aromatic or heterocyclic aromatic group which may have a substituent, R
8
represents a hydrogen atom, a C
1-4
alkyl group which may have a substituent or an aromatic group which may have a substituent or R
8
and Z
1
may be coupled together to form a nitrogen-containing heterocyclic group which may have a substituent, and Z
2
represents a divalent group obtained by removing two hydrogen atoms from the methylene group on the ring of a heterocyclic aromatic compound which may have a substituent,
with the proviso that when A is a group of the formula (2), B represents the group −Z
1
, and Z
1
represents an aromatic group or, when A is a group of the formula (2), B represents the group —CH═Z
2
, Z
2
represents an indolinidene group and n does not stand for 0, the aromatic or indolinidene group has at least one substituent represented by the formula: —NR
9
R
10
(in which R
9
represents a C
1-4
alkyl group having as a substituent a chlorine atom or a cyano, acylamino, alkoxy, monoalkylamino, dialkylamino or trimethylammoniumyl group, or a phenyl group which may have a substituent and R
10
represents a C
1-6
alkyl group which may have a substituent),
n stands for an integer of 1 to 3 when B represents the group —Z
1
or group —NR
8
—Z
1
and n stands for an integer of 0 to 3 when B represents the group —CH═Z
2
; and
Y
31
represents an anion.
BEST MODE FOR CARRYING OUT THE INVENTION
In the formula (1), examples of the C
1-6
alkyl group represented by R
1
or R
2
include methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl and isopentyl groups. R
1
and R
2
may be the same or different. Examples of the substituent which may be possessed by them include cyano group, chlorine atom, hydroxyl group, amino group, methoxy group and diethylamino group. When B stands for the group —Z
1
or —NR
8
—Z
1
, particularly preferred as n is 1, while when B stands for the group —CH═Z
2
, 0 or 1 is particularly preferred. When B stands for the group —CH═Z
2
, 0 is most preferred as n because of stability to an oxidizing agent, particularly to hydrogen peroxide.
In the formula (1), when A represents a group of the formula (2), examples of the C
1-6
alkyl group represented by R
3
, R
4
or R
5
include methyl ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl and isopentyl groups. R
3
, R
4
and R
5
may be the same or different. R
4
and R
1
may form a cyclic structure together with two adjacent carbon atoms and as such a cyclic structure, 5— to 7-membered ones are preferred. R
3
, R
4
or R
5
may have, as a substituent, a sulfonic acid group or salt thereof, cyano group, chlorine atom, hydroxyl group, amino group, alkoxy group, monoalkylamino group, dialkylamino group, trimethylammoniumyl group, oxo group, carbamoyl group

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