Hair dye composition

Details Hair dye composition Hair dye composition

2001-06-26

2004-02-10

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S425000, C008S423000, C008S451000, C008S455000, C008S454000

Reexamination Certificate

active

06689173

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a hair dye composition having markedly high dyeing power, can strongly impart the hair with an extremely vivid red color, has less color fade over time and undergoes a small change in the color tone 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 cationic group is contained in an azo-based (—N═N—) 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 which has high hair dyeing power, less color fade over time, and excellent storage stability to permit only a small change in color tone of the dye after storage.
The present inventors have found that when the below-described compound which is known, in Offenlegungsschrift DE-3531774, as a cationic dye for dyeing or printing therewith fiber materials, paper or leather, is used as a hair dye, the resulting hair dye composition can strongly impart the hair with an extremely vivid red color without decomposing the dye upon hair dyeing, exhibits excellent light resistance, washing resistance, perspiration resistance, friction resistance and heat resistance, and undergoes a small change in the 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
, R
2
, R
3
and R
4
each independently represents a C
1-6
alkyl group which may have a substituent, an alkenyl group which may have a substituent or an aryl group which may have a substituent, or R
3
and R
4
, when taken together with the adjacent carbon atom, form a 5- to 12-membered ring,
R
5
represents a hydrogen atom, a C
1-6
alkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an acyl group,
X
1
and X
2
each independently represents a hydrogen atom or a halogen atom,
Y
1
and Y
2
each independently represents a hydrogen atom, a C
1-6
alkyl group which may have a substituent, an alkenyl group which may have a substituent, a C
1-6
alkoxy group which may have a substituent or a halogen atom,
Z
1
and Z
2
represents a hydrogen atom, a C
1-6
alkyl group which may have a substituent, an alkenyl group which may have a substituent, a C
1-6
alkoxy group which may have a substituent, a nitro group or a halogen atom, and
A
−
represents an anion.
In another aspect of the present invention, there is also provided a method for dyeing the hair with the above-described hair dye composition.
BEST MODE FOR CARRYING OUT THE INVENTION
In the formula (1), examples of the C
1-6
alkyl group represented by R
1
, R
2
, R
3
, R
4
, R
5
, Y
1
, Y
2
, Z
1
or Z
2
include methyl, ethyl, propyl, isopropyl and cyclohexyl groups, each of which may be substituted by an aryl group, alkoxy group, amino group, mono-or di-(C
1-4
alkyl)-substituted amino group, tri(C
1-4
alkyl)-substituted ammoniumyl group, acyl group, hydroxy group, cyano group or halogen atom.
Examples of the C
1-6
alkoxy group represented by Y
1
, Y
2
, Z
1
or Z
2
include methoxy, ethoxy, propoxy and isopropoxy and groups, each of which may be substituted by an aryl group, alkoxy group, amino group, mono- or di-(C
1-4
alkyl)-substituted amino group, tri(C
1-4
alkyl)-substituted ammoniumyl group, acyl group, hydroxy group, cyano group or halogen atom.
Examples of the alkenyl group represented by R
1
, R
2
, R
3
, R
4
, R
5
, Y
1
, Y
2
, Z
1
or Z
2
include vinyl and allyl groups, each of which may be substituted by an aryl group, an alkoxy group, amino group, mono- or di-(C
1-4
alkyl)-substituted amino group, tri(C
1-4
alkyl)-substituted ammoniumyl group, acyl group, hydroxy group, cyano group or halogen atom.
Examples of the aryl group represented by R
1
, R
2
, R
3
, R
4
or R
5
include phenyl and naphthyl groups, each of which may be substituted by an alkyl group, aryl group, alkoxy group, amino group, hydroxy group, cyano group, nitro group, trifluoromethyl group or halogen atom, more specifically, methyl group, ethyl group, methoxy group, ethoxy group, chlorine atom or bromine atom.
Examples of the 5- to 12-membered ring formed by R
3
and R
4
when they are taken together with the adjacent carbon atom include cyclopentane and cyclohexane rings.
Examples of the anion represented by A
−
in the formula (1) include chloride ions, bromide ions, iodide ions, trichlorozincic acid ions, tetrachlorozincic acid ions, sulfuric acid ions, hydrosulfuric acid ions, methyl sulfate ions, phosphoric acid ions, formic acid ions and acetic acid ions.
Specific examples of the direct dye (1) to be used in the present invention.
As a direct dye, at least one of these direct dyes (1) can be used or another direct dye can be used in combination therewith. In particular, combination with yellow and blue dyes makes it possible to dye the hair with a deep and highly lustrous dark brown or black color.
Examples of the direct dye other than the direct dyes (1) include Basic Blue 7 (C.I. 42595), Basic Blue 26 (C.I. 44045), Basic Blue 99 (C.I. 56059), Basic Violet 10 (C.I. 45170), Basic Violet 14 (C.I. 42515), Basic Brown 16 (C.I. 12250), Basic Brown 17 (C.I. 12251), Basic Red 2 (C.I. 50240), Basic Red 22 (C.I. 11055), Basic Red 76 (C.I. 12245), Basic Red 118 (C.I. 12251:1) and Basic Yellow 57 (C.I. 12719); and basic dyes as described in Japanese Patent Publication No. Sho 58-2204, Japanese Patent Application Laid-Open No. Hei 9-118832, Japanese Language Laid-Open Publication (PCT) No. Hei 8-501322 or Japanese Language Laid-Open Publication (PCT) No. Hei 8-507545.
The direct dye (1) is preferably added in an amount of 0.01 to 20 wt. %, more preferably 0.05 to 10 wt. %, especially 0.1 to 5 wt. % based on the whole composition (after mixture of all the component parts when the hair dye composition is a two part or three part type; this will apply equally hereinafter). When another direct dye is added in combination, the content of it in total with the direct dye (1) preferably ranges from 0.05 to 10 wt. %, especially 0.1 to 5 wt. %.
The hair dye composition of the present invention is preferably adjusted to pH 6 to 11, with pH 8 to 11 being especially preferred. Examples of the alkali agent to be used for pH adjustment include ordinarily employed ones such as ammonia, organic amines and salts thereof. The alkali agent is preferably added in an amount of 0.01 to 20 wt. %, more pr

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