Hair dye composition

Details Hair dye composition Hair dye composition

2001-06-25

2003-08-19

Kopec, Mark (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S471000, C008S531000, C008S922000, C008S924000, C534S753000

Reexamination Certificate

active

06607563

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 color ranging from yellow, red, purple to blue, 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 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, as a dye for dyeing and printing therewith fiber materials, paper or leather, in Offenlegungsschrift DE-1569648, UK Patent Application GB 2054630, Japanese Patent Application Laid-Open (Kokai) Nos. Hei 7-224230, Sho 51-109024 and Sho 56-134280, Offenlegungsschrift DE 2347756, Japanese Patent Applications Laid-Open Nos. Sho 49-54685, Sho 49-54686 and Sho 49-54687, or as Basic Blue 16 and Basic Black 2 is used as a hair dye, the resulting dye composition can strongly impart the hair with a vivid color ranging from yellow, red, purple to blue 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):
A—D═D—B  (1)
wherein, A represents a group of the following formula (2), (3), (4), (5), (6), (7) or (8):
(in which, R
1
and R
6
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, R
2
and R
3
each independently represents 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 R
2
and R
3
, when taken together with the adjacent carbon atom, form a 5- to 7-membered cycloalkane ring, R
4
represents a hydrogen atom, 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, 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, an acyl group, an alkoxycarbonyl group, a carbamoyl group, an alkylsulfonyl group or an arylsulfonyl group, Q represents a nitrogen atom or a group CR′ (in which R′ represents a hydrogen atom, 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), R
7
represents an aralkyl group which may have a substituent or a group CH
2
—CH(OH)—CH
2
—OR″ (in which R″ 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), R
8
and R
9
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 or an aryl group which may have a substituent, or R
8
and R
9
, when taken together with the adjacent nitrogen atom, form a nitrogen-containing heterocycle, X
−
represents an anion, and rings C, E, F, G, H and I may each independently have a further substituent or may be cyclocondensed with another aromatic ring),
D represents a nitrogen atom or a group CR′″ (in which R′″ represents a hydrogen atom or a C
1-6
alkyl group which may have a substituent), and
B represents the residue of a phenol, aniline, acylacetoarylamide, pyridone, quinoline, isoquinoline, pyrazole, indole, diphenylamine, aminopyridine, pyrimidine, pyrimidone, naphthol, naphthylamine, aminothiazole, thiophene or hydroxypyridine type coupling component.
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
Examples of the C
1-6
alkyl group represented by R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
8
, R
9
, R′, R″ or R′″ include methyl, ethyl, propyl, isopropyl and cyclohexyl groups; those of the alkenyl group include vinyl, allyl and isobutenyl groups; and those of the aryl group include phenyl and naphthyl groups, each of which may be substituted by an aryl group, cyano group, halogen atom, hydroxyl group, C
1-4
alkoxy group, C
1-4
hydroxyalkoxy group, alkoxycarbonyl group, heterocyclic group, group NR
10
R
11
(in which R
10
and R
11
each independently represents a hydrogen atom, a C
1-6
alkyl group which may have a substituent or an aryl group which may have a substituent).
Examples of the cycloalkane ring formed by R
2
and R
3
when they are taken together with the adjacent carbon atom include cyclopentane, cyclohexane and cycloheptane rings.
Examples of the acyl group represented by R
5
include formyl, acetyl and propionyl groups, those of the alkoxycarbonyl group include methoxycarbonyl and ethoxycarbonyl groups; those of the alkylsulfonyl group include methanesulfonyl group; and those of the arylsulfonyl group include benzenesulfonyl and toluenesulfonyl groups.
Examples of the aralkyl group represented by R
7
include benzyl and phenethyl groups.
Examples of the nitrogen-containing heterocycle formed by R
8
and R
9
when they are taken together with the adjacent nitrogen atom include pyrrolidine, piperidine, morpholine and piperazine rings, each of which may be substituted by an alkyl group.
Examples of the substituent which an aralkyl group represented by R
7
or the ring C, E, F, G or H may have include alkyl groups, aryl groups, alkoxy groups, amino group, mono- or di-alkylamino groups, hydroxy group, cyano group, nitro group, acylamino groups, halogen atoms and alkoxycarbonyloxy groups, more specifically, methyl, ethyl, methoxy, ethoxy, chlorine and bromine. As another aromatic ring with which the above-described ring may be cyclocondensed, the benzene ring may be given as an example.
Examples of the anion represented by X
−
include chloride ions, bromide ions, iodide ions, trichloroz

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