Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2002-03-14
2004-08-31
Gupta, Yogendra N (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S662000, C008S677000, C008S678000, C008S690000, C008S691000, C008S692000
Reexamination Certificate
active
06783558
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a hair colouring method using a composition that comprises at least one specific direct dyestuff, which can impart a vivid and durable colour to the hair and is stable to oxidizing agents. In addition, the present invention also relates to the hair colouring composition.
BACKGROUND ART
Hair colouring compositions which comprise several anionic or cationic direct dyestuffs are well-known and, contrary to the permanent hair colouring compositions comprising oxidative dye intermediates, require no coupling reaction by oxidizing agents. This type of direct colouring composition is often applied to the hair in the form of a so-called tinting shampoo together with surface-active components, or is applied in the form of a lotion, emulsion or thickened solution such as a gel.
This direct hair colouring composition should, however, be improved in its colour durability and in particular colour intensity as well as uniformity of resulting colour and colour gloss. Additionally, the above-described direct dyestuffs generally have the drawback that they are not compatible with alkaline peroxides, so the direct hair colouring compositions are generally applied to the hair without peroxide. Accordingly, the direct hair colouring composition has no bleaching effect on the hair.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a hair colouring method using a composition, on the basis of direct dyestuffs, which shows excellent dyeing characteristics and gives to the hair a durable and vivid colour over time and which can be applied to the hair in the form of a lotion, emulsion, solution, gel, suspension or also an aerosol by adding propellants.
Another object of the present invention is to provide a hair colouring method using a composition that also supplies hair bleaching power coupled with the above-described performance, based on the direct dyestuffs.
The solution to these objects is a hair colouring method using a composition comprising at least one specific direct dyestuff that has good hair colouring performance and compatibility with peroxides.
The present inventors have found that when the below-described ring-fused heterocycle direct dyes are used as a hair dyes, surprisingly, the resulting hair colouring composition can impart the hair with more vivid and durable colour than general oxidative hair colouring compositions.
In addition, the present inventors have found that the below-described ring-fused heterocycle direct dyestuffs have excellent stability against alkaline peroxide, and that the hair colouring effect of the composition comprising at least one of the below-described direct dyestuffs can be further improved when one applies this composition comprising at least one peroxide and preferably having a pH value of 6.5 to 12.5, together with at least one ring-fused heterocycle direct dyestuff, because hair bleaching power derived from alkaline peroxide serves more vividness to the hair.
In one aspect of the present invention, there is thus provided a hair colouring method by using a composition comprising at least one direct dyestuff represented by the general formula (1) or a salt thereof:
wherein B represents a heterocyclic group of the following formula (B-1), (B-2), (B-3) or (B-4):
(wherein each of Za, Zb, Zc, Z
1
, Z
2
and Z
3
independently represents a nitrogen atom or a group —C(R
5
)═, at least one of Zb and Zc is the group —C(R
5
)═ and at least one of Z
1
, Z
2
and Z
3
is a nitrogen atom.
R
1
, R
4
and R
5
independently represent a hydrogen atom; a halogen atom; a C
1-5
alkyl group which may be optionally substituted by one or more of halogen atom(s), hydroxy group(s), alkoxy group(s), aryloxy group(s), amino group(s), alkylamino group(s), hydroxyalkylamino group(s), acyl group(s), acylamino group(s) or alkylsulfonylamino group(s); a C
1-4
alkoxy group; a C
1-4
alkylthio group; an arylthio group; a heteroarylthio group; a benzylthio group; an acyl group which may be optionally substituted by one or more of hydroxy group(s) or amino group(s); an acylamino group; an alkylsulfonylamino group; an acyloxy group; a carbamoyl group; an alkylaminocarbonyl group; a dialkylaminocarbonyl group; a phenyl group which may be optionally substituted by one or more of halogen atom(s), nitro group(s), sulfo group(s), alkylsulfonyl group(s), C
1-4
alkyl group(s), C
1-4
alkoxy group(s), C
1-3
fluoroalkyl group(s), amino group(s), alkylamino group(s), hydroxyalkylamino group(s) or alkylsulfonylamino group(s); an alkoxycarbonyl group which may be optionally substituted by one or more of hydroxy group(s); an aryloxycarbonyl group; a heteroaryloxycarbonyl group; a cyano group; a nitro group; a dialkylphosphinyl group; an alkylsulfinyl group; an arylsulfinyl group; a sulfamoyl group; an alkylaminosulfonyl group; a dialkylaminosulfonyl group; a carboxy group; a sulfo group; an aryloxy group which may be optionally substituted by one or more of alkoxy group(s); an heteroaryloxy group; a C
1-4
alkylamino group; an ureido group; a sulfamoylamino group; an alkoxycarbonylamino group; an aryloxycarbonylamino group; or a phosphonyl group),
each of R
2
and R
3
independently represents a hydrogen atom, a C
1-5
alkyl group, an acylamino group, an alkylsulfonylamino group or an electron withdrawing group,
and * represents the position which binds to the nitrogen atom in the formula (1).
In another aspect of the present invention, there is thus provided the above-described hair colouring composition.
BEST MODE FOR CARRYING OUT THE INVENTION
A group of the following formula (B-1-1) or (B-1-2) which has pyrazolotriazole structure:
(wherein each of R
1
, R
5
and * has the same meanings as described above) is preferred as the group (B-1).
A group of the following formula (B-2-1), (B-2-2) or (B-2-3) which has imidazoloazole structure:
(wherein each of R
1
, R
5
and * has the same meanings as described above) is preferred as the group (B-2).
A group of the following formula (B-3-1) or (B-3-2) which has pyrroloazole structure:
(wherein each of R
1
, R
4
, R
5
and * has the same meanings as described above) is preferred as the group (B-3).
A group of the following formula (B-4-1) or (B-4-2) which has pyrroloazole to structure:
(wherein each of R
1
, R
4
, R
5
and * has the same meanings as described above) is preferred as the group (B-4).
Above all, the groups (B-1-1) and (B-1-2) which have pyrazolotriazole structure are most preferable in the light of vividness and durability of the resulting colour.
As the group represented by R
1
, R
4
or R
5
, hydrogen atom; C
1-5
alkyl group which may be optionally substituted by one or more of hydroxy group(s), alkoxy group(s), amino group(s), alkylamino group(s) or alkylsulfonylamino group(s); a C
1-4
alkoxy group; or phenyl group which may be optionally substituted by one or more of halogen atom(s), C
1-4
alkyl group(s), C
1-4
alkoxy group(s), amino group(s), alkylamino group(s) or alkylsulfonylamino group(s); are in particular preferred in the light of hair colouring intensity. Of these, C
1-5
alkyl group, which has no substituent, is most preferable in the light of hair colouring intensity.
The compound of formula (1) preferably has a pKa value of 2.5 to 9, in particular 3 to 8, most preferably 3.5 to 7 in the light of hair colouring ability and durability of the resulting colour. The hydroxy group on the benzene ring is dissociative. For this reason, an electron withdrawing group is preferable as each of R
2
and R
3
. Dyes having dissociative group are called dissociative dyes.
The dissociative dye represents the dye that can release a proton and be anionic above a certain pH value. The pKa value can be determined by the following method: The sample is dissolved in a solution of a DMF/water (1/1) volume ratio to a final concentration of 2×10
−5
mol/l. After the resulting solution is adjusted to pH 2, using 1.0 mol/l hydrochloric acid, the solution is titrated with aqueous 1.0 mol/l sodium hydroxide solution. Recording the change of the vi
Kawagishi Toshio
Pratt Dominic
Gupta Yogendra N
Kao Corporation
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