Hair dye composition

Details Hair dye composition Hair dye composition

2003-04-10

2004-06-08

Mruk, Brian P. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S407000, C008S409000, C008S410000, C008S411000, C008S426000, C008S437000

Reexamination Certificate

active

06746493

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a hair dye composition which has markedly high dyeing power, can impart the hair with a vivid color ranging from yellow to orange, 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 when a cationic group is contained 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 which has high hair dyeing power, has less color fade over time, and undergoes only a smaller change in color tone of the dye after storage, therefore has excellent stability.
The present inventors have found that a hair dye composition containing the below-described compound—which is known as a cationic dye for dying or printing therewith fiber materials, paper or leather and is, for example, described in Japanese Patent Application Laid-Open (Kokai) No. Sho 53-12931, Sho 54-7425, Sho 54-127433 or Sho 56-76457 is named as Basic Yellow 21 or Basic Yellow 28—can impart the hair with a vivid color ranging from yellow to orange without decomposing the dye upon hair drying, exhibits excellent light resistance, washing resistance, perspiration resistance, friction resistance and heat 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):
A—CR
1
═N—NR
2
—B X
−
  (1)
[wherein, A represents a group of the following formula (2) or (3):
(in which, R
3
, R
4
and R
5
each independently represents a C
1-6
alkyl group which may have a substituent, ring C may have a substituent or may be cyclocondensed with an aromatic ring, R
6
and R
7
each independently represents a C
1-6
alkyl group which may have a substituent, or may be coupled to form a heterocycle together with the adjacent nitrogen atom, Z represents a C
1-4
divalent linear hydrocarbon group which may have a substituent and ring D may be cyclocondensed with an aromatic ring).
B represents an aromatic group which may have a substituent,
R
1
represents a hydrogen atom or a C
1-6
alkyl group which may have a substituent,
R
2
represents a hydrogen atom or a C
1-6
alkyl group which may have a substituent or an aromatic group which may have a substituent, or may form a heterocycle together with the carbon atom of the aromatic ring B, and
X
−
represents an anion.]
In another aspect of the present invention, there is also provided a hair dyeing method which comprises applying the above-described hair dye composition to the hair.
BEST MODE FOR CARRYING OUT THE INVENTION
In the formulas (1), (2) and (3), examples of the C
1-6
alkyl group as R
1
, R
2
, R
3
, R
4
, R
5
, R
6
or R
7
include methyl, ethyl, propyl, isopropyl and cyclohexyl groups, which may each be substituted with an aryl, alkoxy, amino, hydroxyl or cyano group, or a halogen atom.
In the formula (1), examples of the substituent for the aromatic group as B or R
2
or for the ring C include alkyl, aryl, alkoxy, amino, dialkylamino, hydroxyl, cyano and nitro groups and halogen atoms, more specifically, methyl, ethyl, methoxy, ethoxy and diethylamino groups and chlorine and bromine atoms. The substituent for B may be cationic and a trimethylammonium ethoxy group may be mentioned as an example.
In the formula (3), examples of the C
1-4
divalent linear hydrocarbon group represented by Z include methylene, ethylene, trimethylene, propylene and butylene groups, which may each be substituted by an aryl, alkoxy, amino, hydroxyl or cyano group, or a halogen atom.
In the formula (1), examples of the anion as X
−
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:
As the direct dye (1), one or more can be used. Alternatively, another direct dye can be used in combination. Combination of the direct dye (1) with red 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 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 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 preferably 0.1 to 10 wt. %, especially 0.5 to 5 wt. % based on the whole composition.
In the hair dye composition of the present invention, an oxidizing agent can be incorporated. In this case, hair dyeing and bleaching can be carried out simultaneously, which facilitates more vivid hair dyeing. Ordinarily employed oxidizing agents, for example, hydrogen peroxide, persulfates such as ammonium persulfate, potassium persulfate and sodium persulfate, perborates such as sodium perborate, percarbonates such as sodium percarbonate and bromates such as sodium bromate and potassium bromate are usable. Out of them, hydroge

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