Hair dye composition

Details Hair dye composition Hair dye composition

2001-03-16

2002-09-17

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S405000, C008S406000, C008S407000, C008S416000, C008S423000

Reexamination Certificate

active

06451069

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a hair dye composition having markedly high dyeing power, can impart the hair with a vivid and deep color shade ranging from red to blue, has less color fade over time and undergoes a smaller 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 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 smaller change in color tone of the dye after storage.
The present inventors have found that when the below-described cationic dye which is known (Japanese Patent Application Laid-Open (Kokai) No. Sho 49-24224, Sho 49-24228 or Hei 6-192582) to dye therewith polyacrylonitrile fibers, or polyester or polyamide fibers having an acid residue as a dyeing site is used as a hair dye, the resulting dye composition can impart the hair with a vivid and deep color tone ranging from red to blue without decomposing the dye upon hair drying, exhibits excellent light resistance, washing resistance, perspiration resistance, friction resistance and weather resistance, and undergoes a smaller 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, B
1
and B
2
are the same or different and each independently represents a group of the following formula (2), (3), (4) or (5):
(in which, A represents a phenylene group which may have an unionizable substituent, or a naphthylene group; R
3
and R
4
are the same or different and each independently represents a hydrogen atom, a C
1-4
alkyl group which may have a substituent, an aralkyl group or a phenyl group, X
1
represents an oxygen atom, an imino group or a methylene group, X
2
represents an ethylene or trimethylene group which may have a substituent, Y represents a C
1-4
alkyl group or aralkyl group which may have a substituent, R
5
represents a C
1-4
alkyl group, or an aryl group, R
6
represents a hydrogen atom or a C
1-4
alkyl group and R
7
represents a hydrogen atom or an unionizable group),
R
1
and R
2
are the same or different and each independently represents a C
1-4
alkyl group, a carbamoylethyl group, a 2-carbamoylpropyl group, a benzyl group or a group of the following formula (6) or (7):
(in which, X
3
represents a hydroxyl group, an amino group or a thiol group, R
8
represents a hydrogen atom, a halogen atom, a C
1-4
alkyl group which may have a substituent, a C
1-4
alkoxy group or a phenoxy group, and R
9
represents a hydrogen atom or a phenyl group which may have a substituent), and
X
−
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
Compound (1) is known as a dye for specific synthetic fibers and described in Japanese Patent Application Laid-Open (Kokai) No. Sho 49-24224, Sho 49-24228 or Hei 6-192582. In the present invention, a vivid and deep color shade ranging from red to blue can be imparted to the hair by using this Compound (1) as a direct dye of the hair dye.
In B
1
or B
2
of the formula (1), examples of A in the formula (2) or (3) include phenylene, chlorophenylene, acetylaminophenylene, methylphenylene, methoxyphenylene and naphthylene. Examples of R
3
or R
4
in the formula (2) include hydrogen atom, methyl group, ethyl group, cyanoethyl group, hydroxyethyl group, benzyl group, phenyl group, methoxyethyl group and chloroethyl group. Examples of X
2
in the formula (4) include trimethylene, 2-hydroxy-trimethylene, 2-chlorotrimethylene, 2-methoxytrimethylene, propylene and 1,1,2-trimethylethylene, while examples of Y in the formula (4) include methyl, butyl, bromoethyl and benzyl. Examples of R
5
in the formula (5) include methyl, ethyl, phenyl and tolyl, while those of R
6
include hydrogen atom, methyl group and ethyl group. Those of R
7
include methyl group, chlorine atom and methoxy group.
Examples of the C
1-4
alkyl group of R
1
or R
2
in the formula (1) include methyl and ethyl groups, while those of R
8
in the formula (6) include a methyl group, a phenoxy group, a chlorine atom, a methacryloyloxy group, a butoxy group, an ethoxy group and a bromine atom.
Examples of the anion represented by X
−
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 include the following compounds:
These direct dyes (1) can be used either singly or in combination with another direct dye. In particular, combination with a yellow dye 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 parts when a two part or three part composition is employed; this will apply equally hereinafter). When another direct dye is added in combination, the content of it 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 th

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