JP2002220329A - Hair dye composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a hair dye composition having uniform dyeing property and excellent color fastness. SOLUTION: The hair dye composition contains at least one cationic direct dye having a predetermined chemical formula and at least one specified surfactant in a medium suitable for dyeing.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention relates to a hair dye composition containing at least one cationic direct dye of a predetermined formula and at least one specific surfactant in a medium suitable for dyeing. About.

[0002]

2. Description of the Related Art In the so-called direct dyeing, such as semi-permanent dyeing or temporary dyeing of hair, a dye capable of imparting a color change to the hair that can withstand several to more than ten shampoos (hair washing). Use These dyes are mainly used without using an oxidizing agent, because the dyes themselves have a color, unlike so-called oxidation dyes that develop color by oxidative polymerization. Of course, it can be used together with an oxidizing agent, but in this case, the oxidizing agent is used in combination for the purpose of bleaching the hair. And hair can be dyed with a vivid color close to the primary color. Conventionally, acidic dyes and nitro dyes have been used as these direct dyes.

[0003]

However, these dyes,
In particular, since acidic dyes are easily dyed and hardly fall off when they adhere to the skin, a technique for applying the dye so that it does not adhere to the skin or a special application tool was required for the treatment. In addition, even if it is dyed with great care, the pigment is washed away several times at the earliest and the color of the hair is restored to its original color. Although this feature has the advantage that the color of hair can be easily changed, it has been a source of dissatisfaction for customers who expect color durability.

[0004] In recent years, new cationic direct dyes have been developed to replace these dyes.
No. 1322 and JP-T-08-507545. Since this dye is difficult to be dyed even if it adheres to the skin, the treatment can be performed very easily. However, with these dyes, on the other hand, the coloring is too selective,
Since the degree of dyeing varies depending on the surface condition of the hair, it is difficult to obtain a uniform hair dyeing power, and it is also satisfactory in resistance to various external factors that the hair may suffer, such as sunlight (ultraviolet rays) and hair washing. It has not become a thing.

[0005]

As a result of intensive studies on this problem, the present inventors have combined at least one conventionally known cationic direct dye with at least one specific surfactant. By doing so, it is possible to obtain a hair dye composition that shows good resistance to various external factors that the hair may suffer and can obtain coloring power with almost no selectivity. I found it.

That is, the present invention provides a medium suitable for dyeing,
(I) a composition comprising at least one cationic direct dye having a structure corresponding to the following formula,
i) A hair dye composition further comprising at least one specific surfactant.

[0007]

DETAILED DESCRIPTION OF THE INVENTION The cationic direct dyes which can be used according to the invention correspond to the following formulas (I), (II) and (III):

[0008]

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In the above formula, X is -O-, -S- or -N
R³Y represents -CH =, -CR ³= Or -N =
And R¹Is a hydrogen atom, C₁~ C₄Alkyl group, nitro
B group, amino group, C₁~ C₄Monoalkylamino group or
Is Di-C₁~ C₄R represents an alkylamino group;²And R³
Are each independently unsubstituted or OH-, C₁~
C₄Alkoxy-, halogen-, CN-, amino-, C
₁~ C₄Monoalkylamino- or di-C₁~ C₄A
Alkylamino-substituted C₁~ C₄Represents an alkyl group. K
Is the residual aniline or phenolic coupling component
Represents a group or a residue of a heterocyclic coupling component,
Is -N (CH₃)-, Y is -N = and R¹And R²But it
In the case of each methyl group, K is N, N-dimethylaniline
Residue. R⁴Is hydrogen atom, halogen
Atom, C₁~ C₄Alkyl group or C₁~ C₄Alkoki
Represents a group. R⁵, R⁶, R⁷, R⁸Are independent of each other
A hydrogen atom or C₁~ C₄An alkyl group, provided that
At least one of these four substituents is C₁~ C₄
Alkyl and all four are ethyl
But R⁹And R¹⁰Are independently a hydrogen atom, C₁
~ C₄Alkyl group or C₁~ C₄Table showing alkoxy groups
You. A- represents an anion. Compounds indicated by｝
Selected from things.

The cationic direct dyes of the formulas (I), (II) and (III) which can be used in the dyeing composition of the present invention are known compounds.
01322 and JP-T-08-507545.

The cationic direct dye of the formula (I) which can be used in the dyeing composition of the present invention includes, for example,
The following structures (I-1) to (I-41):

[0012]

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[0013]

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[0014]

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[0015]

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[0016]

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[0017]

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[0018]

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[0019]

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The compounds corresponding to the structures (I-1), (I-2) and (I-
Compounds corresponding to 3) or (I-19) are particularly preferred.

The cationic direct dyes of the formula (II) which can be used in the dyeing composition of the present invention include, in particular, the following structures (II-1) to (II-4):

[0022]

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The compounds corresponding to the structure (II-1) are particularly preferable.

The cationic direct dye of the formula (III) which can be used in the dyeing composition of the present invention includes, in particular, the following structures (III-1) to (III-9):

[0025]

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[0026]

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The compounds corresponding to the structures (III-1), (III-2) and (III-3) are particularly preferable.

The cationic direct dye used in the present invention accounts for 0.001 to 10% by weight, preferably 0.005 to 5% by weight, based on the total weight of the hair dye composition.

Specific surfactants in the present invention include higher fatty acid diethylaminoethylamide, alkyldimethylaminoacetic acid betaine, fatty acid amidopropyldimethylaminoacetic acid betaine, and N-acylaminoethyl-N-2-
Hydroxyethyl glycine salt and N- [3-alkyl (12,14) oxy-2-hydroxypropyl] -L
-One or more selected from arginine hydrochloride.

The higher fatty acid diethylaminoethylamide includes diethylaminoethylamide stearate and diethylaminopropylamide palmitate.

Examples of the betaine alkyldimethylaminoacetate include betaine decyldimethylaminoacetate, betaine lauryldimethylaminoacetate, betaine myristyldimethylaminoacetate, betaine cetyldimethylaminoacetate, betaine stearyldimethylaminoacetate, betaine oleyldimethylaminoacetate, and behenyldimethylamino. Betaine acetate, coconut oil alkyldimethylamino betaine and salts thereof, and the like.

Examples of the fatty acid amidopropyldimethylaminoacetic acid betaine include coconut oil fatty acid amidopropyldimethylaminoacetic acid betaine, palm oil fatty acid amidopropyldimethylaminoacetic acid betaine, lauric acid amidopropyldimethylaminoacetic acid betaine, and ricinoleic acid amidopropyldimethylaminoacetic acid betaine. And salts thereof.

Examples of N-acylaminoethyl-N-2-hydroxyethylglycine salts include undecyl-N-hydroxyethyl-N-carboxymethylimidazolinium betaine and coconut fatty acid acyl-N-hydroxyethyl-N-carboxymethyl. Examples include imidazolinium betaine and salts thereof.

Among them, diethylaminoethylamide stearate, betaine lauryldimethylaminoacetate, betaine laurateamidopropyldimethylaminoacetate, undecyl-N-hydroxyethyl-N-carboxymethylimidazolinium betaine and salts thereof, and N -[3-alkyl (12,14) oxy-2
-Hydroxypropyl] -L-arginine hydrochloride is preferred.

These surfactants in the dyeing composition of the present invention are used in an amount of 0.1 to 40 with respect to the total weight of the hair dye composition.
%, Preferably 0.5 to 20% by weight.

Suitable media for dyeing comprise at least a mixture of water and at least one surfactant as described above.
To dissolve compounds that are not sufficiently soluble in the medium,
Surfactants other than the surfactants used in the present invention, organic solvents, and the like can be contained. Other surfactants include alkyl sulfate, polyoxyethylene alkyl / alkyl allyl ether sulfate, sulfosuccinate, N-acyl sulfonate, alkylbenzene sulfonate, α-olefin sulfonate, N-acyl amino acid Salts, anionic surfactants such as polyoxyethylene (hereinafter abbreviated as POE) alkyl ether phosphoric acid and salts thereof, cationic surfactants such as quaternary ammonium salts, POE alkyl ethers, POE alkyl phenyl ethers, Nonionic surfactants such as POE / POP alkyl ethers and POE sorbitan fatty acid esters are exemplified.

As the organic solvent, for example, ethyl alcohol, isopropyl alcohol, butyl alcohol, benzyl alcohol, 2-phenylethyl alcohol, cinnamon alcohol, phenylpropanol, α-methylbenzyl alcohol, dimethylbenzylcarbinol, 2-benzyl Monohydric alcohols such as oxyethanol, phenoxyethanol, phenethyl alcohol, p-anisyl alcohol, 2-benzyloxy alcohol, ethylene glycol, propylene glycol, 1,
Examples include polyhydric alcohols such as 3-butylene glycol, isoprene glycol, glycerin, diglycerin, and dipropylene glycol, and N-alkylpyrrolidones such as N-methylpyrrolidone.

The pH of the dyeing composition of the present invention is generally 2 to 11, preferably 5 to 10. This pH, using the acid or alkali agent used in ordinary cosmetics,
It can be adjusted to a desired value.

Examples of the acid include an inorganic acid and an organic acid, such as hydrochloric acid, orthophosphoric acid, sulfuric acid, and carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.

Examples of the alkaline agent include aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamine and derivatives thereof, sodium hydroxide, potassium hydroxide and the like.

The dyeing composition of the present invention may contain other direct dyes in addition to the above-described cationic direct dyes as long as the effects of the present invention are not impaired. Other direct dyes include nitrobenzene dyes and acid dyes having an anionic group in the molecule. Preferably, nitrobenzene dyes include nitro-p-phenylenediamine, p-nitroorthophenylenediamine, p- Nitro-m-phenylenediamine, N1, N4, N4-tris (2-hydroxyethyl) -2-nitroparaphenylenediamine (HC Blue # 2), 1- (2-aminoethyl) amino-4- (2-hydroxy Ethyl) oxy-2-nitrobenzene (HC Orange # 2), N
1- (2-hydroxyethyl) -2-nitroparaphenylenediamine (HC Red # 3), 2-amino-5
(2-hydroxyethylamino) nitrobenzene (HC
Red # 7), N- (2-hydroxyethyl) -2-
Nitroaniline (HC Yellow # 2), 2-
[[2- (2-Hydroxyethoxy) -4-nitrophenyl] amino] ethanol (HC Yellow #
4), N1- (2-hydroxyethyl) -4-nitroorthophenylenediamine (HC Yellow # 5),
1-γ-hydroxypropylamino-2-nitro-4-
Bis (β-hydroxyethyl) aminobenzene (HC
Violet # 2) and their salts. The acid dye is preferably an acid dye selected from dyes (so-called legal dyes) specified by "Ministerial Ordinance for Specifying Tar Dyes that can be Used in Pharmaceuticals and the like" (notified in 1966, Ministry of Health and Welfare).

The dyeing composition of the present invention may contain various additives conventionally used in hair coloring compositions, such as antioxidants, as long as the effects of the present invention are not impaired.
It may further contain a penetrant, a sequestering agent, a fragrance, a buffer, a dispersant, other surfactants, a film forming agent, ceramides, a preservative and the like.

The hair dye composition of the present invention can be in various forms, such as liquids, shampoos, creams or gels, or any other form suitable for dyeing hair.

An example of a dyeing method according to the present invention is to apply at least one of the hair dye compositions described above to the hair and leave it for a time sufficient for the desired color to develop, then rinse and optionally shampoo it. And then rinsed again and dried. The standing time is generally 3 to 60 minutes, preferably 5 to 30 minutes.

In addition, it can be used as a temporary coloring agent that does not soot after being applied to hair.

[0046]

EXAMPLES Next, examples of the present invention will be illustrated, but they do not limit the scope of the present invention.

Example 1 wt% cationic direct dye of formula (III-1) 0.2 cationic direct dye of formula (I-1) 0.4 N- [3-alkyl (12,14) oxy-2 -Hydroxypropyl] -L-arginine hydrochloride 10.0 Monoethanolamine Adjust pH to 9 Purified water qs

The above hair dye composition is prepared by a conventional method,
It was applied to a hair bundle of a person containing 90% of gray hair and left for 30 minutes.
The tress was then rinsed, washed with normal shampoo and dried. The hair was uniformly dyed dark maroon.

The N- [3-alkyl (12,1
4) Instead of oxy-2-hydroxypropyl] -L-arginine hydrochloride, hair was similarly dyed using the composition of Comparative Example 1 in which sodium polyoxyethylene (2) lauryl sulfate was blended. became. In addition, 50
Washing fastness was evaluated using a method of immersion in a 1% sodium lauryl sulfate solution at 15 ° C. for 15 minutes, but Example 1 clearly had better color retention than the Comparative Example.

Example 2 wt% Cationic Direct Dye of Formula (I-2) 0.5 Cationic Direct Dye of Formula (II-1) 0.1 Amidopropyldimethylamino laurate laurate betaine 10.0 2-amino -2-Methylpropanol Adjust the pH to 9 Purified water qs

The above hair dye composition is prepared by a conventional method,
It was applied to a human hair bundle of black hair and left for 30 minutes. The tress was then rinsed, washed with normal shampoo and dried. The hair was uniformly dyed dark red. Example 2
The same hair dyeing was carried out using the composition of Comparative Example 2 in which polyoxyethylene (15) cetyl ether was blended in place of the betaine laurate amidopropyldimethylaminoacetate, but uneven dyeing was obtained. Further, the washing fastness was evaluated in the same manner as in Example 1. However, Example 2 clearly had better color retention.

[0052]

According to the present invention, a hair dye composition having uniform dyeing properties and excellent fastness can be provided.

Continued on front page F-term (reference) 4C083 AC542 AC581 AC582 AC641 AC711 AC712 AC851 AC852 AC862 BB24 CC36 EE26 4H057 AA01 BA03 CA12 CB18 CB19 CC02

Claims (5)

[Claims] 1. In a medium suitable for dyeing: (i)-the following formulas (I), (II) and (III):ＸIn the above formula, X is -O-, -S- or -NR³-
Y is -CH =, -CR ³= Or -N =, R
¹Is a hydrogen atom, C₁~ C₄Alkyl group, nitro group, amino
No group, C₁~ C₄Monoalkylamino group or di-C₁
~ C₄R represents an alkylamino group;²And R³Are each
Unsubstituted or OH-, C₁~ C₄Arco
Xy-, halogen-, CN-, amino-, C₁~ C₄Mo
Noalkylamino- or di-C₁~ C₄Alkylam
No-substituted C₁~ C₄Represents an alkyl group. K is aniline
Or the residue or compound of a phenolic coupling component
Represents a residue of a cyclic coupling component, wherein X is -N (C
H₃)-, Y is -N = and R¹And R²Is methyl
In the case of a group, K is the residue of N, N-dimethylaniline.
Never. R⁴Is a hydrogen atom, a halogen atom, C₁
~ C₄Alkyl group or C₁~ C₄Table showing alkoxy groups
You. R⁵, R⁶, R⁷, R⁸Are independent of each other
Child or C₁~ C₄Alkyl group, provided that these 4
At least one of the substituents is C₁~ C₄Alkyl
And all four are not ethyl groups,
R⁹And R¹⁰Are independently a hydrogen atom, C₁~ C₄A
Alkyl group or C₁~ C₄Represents an alkoxy group. ;
A- represents an anion. ｝; At least selected from
Also one cationic direct dye, and (ii) higher fatty acids
Diethylaminoethylamide, alkyldimethylamino
Betaine acetate, fatty acid amidopropyl dimethylamino vinegar
Betaine acid, N-acylaminoethyl-N-2-hydro
Xyethylglycine salt and N- [3-alkyl (12,
14) Oxy-2-hydroxypropyl] -L-argi
At least one surfactant selected from nin hydrochloride
A hair dye composition characterized by being blended. 2. The hair dye composition according to claim 1, which comprises 0.001 to 10% by weight of a cationic direct dye of the formula (I), (II) or (III). 3. The hair dye composition according to claim 1, comprising 0.1 to 40% by weight of the surfactant. 4. The hair dye composition according to claim 1, further comprising a direct dye. 5. The hair dye composition according to claim 1, wherein the pH is 2 to 11.