KR100789560B1 - Composition for oxidative dyeing of hair containing 4-amino pyridine azo derivatives - Google Patents

Abstract

The present invention relates to an oxidative dyeing hair dye composition containing an oxidized dye precursor and a coupler, characterized by containing a 4-amino pyridine azo derivative represented by the following general formula (1) and / or general formula (2). In the dyeing composition for oxidation dyeing of the present invention containing 4-amino pyridine azo derivative, not only the color of yellow and orange is sufficiently developed when hair is dyed, but also the stability is high so that no dye precipitates or discolors and color persistence against water drainage. Very good.

4-amino pyridine azo derivatives * oxidation dyes * hair dyes

Description

Composition for oxidative dyeing of hair containing 4-amino pyridine azo derivatives}

The present invention relates to an oxidative dyeing hair dye composition containing an oxidized dye precursor and a coupler, and more particularly, yellow and orange colors are sufficiently developed during dyeing, and also have high stability, so that dyes do not precipitate or discolor and do not fade. It also relates to a hair dye composition for oxidation dyeing with very good color persistence.

The dyeing agent composition for oxidation dyeing typically contains at least one oxidation dye precursor and at least one coupler which are oxidized to form a dye. The dyeing agent composition for oxidation dyeing consists of a hydrogen peroxide solution or the like diluted immediately before application to hair. Dyeing is carried out by mixing with. The purpose of the hair dye is to dye the hair as completely as possible, and to maintain the hair dye effect for a long time.

However, the disadvantage that the combination of the oxidizing dyes contained in the conventional hair dye composition for oxidation dyeing cannot develop a sufficient yellow or orange color (Ito Takashi, Arai Genji: 色 材 74 (8), 412-417 (2001)). have. Therefore, a method of adding a nitro direct dye such as N-methyl-p-phenylenediamine has been proposed to compensate for this disadvantage. However, since the nitro direct dyes have low solubility in solvents for hair dyes, they have poor stability, such as reprecipitation as crystals in the hair dye compositions or discoloration of colors during long-term storage, as well as low color persistence due to water drainage. There is this.

Accordingly, the technical problem to be achieved by the present invention is to solve the above problems, not only yellow and orange colors are sufficiently developed during dyeing, but also have high stability, so that dyes do not precipitate or discolor and color persistence against water drainage is very good. It is to provide a hair dye composition.

In order to achieve the above technical problem, the present invention is any one selected from the group consisting of a compound represented by the following formula (1), a compound represented by the following formula (2), and mixtures thereof in a hair dye composition containing an oxidized dye precursor and a coupler It provides a hair dye composition for oxidation dyeing comprising a 4-amino pyridine azo derivative of;

<Formula 1>

<Formula 2>

In Formulas 1 and 2, R is independently an alkyl group having 1 to 4 carbon atoms, a hydroxy alkyl group, a carboxyl group-containing alkyl group or a sulfonyl group-containing alkyl group.

In the dyeing agent composition for oxidation dyeing according to the present invention, the content of 4-amino pyridine azo derivative is preferably 0.001 to 10% by weight based on the total weight of the dyeing agent composition. Even better

Hereinafter, the hair dye composition for oxidation dyeing according to the present invention will be described in detail.

The dyeing agent composition for oxidation dyeing of the present invention is characterized by containing any one of 4-amino pyridine azo derivatives selected from the group consisting of a compound represented by the following formula (1), a compound represented by the following formula (2), and mixtures thereof.

<Formula 1>

<Formula 2>

In Formulas 1 and 2, R is independently an alkyl group having 1 to 4 carbon atoms, a hydroxy alkyl group, a carboxyl group-containing alkyl group or a sulfonyl group-containing alkyl group.

Such 4-amino pyridine azo derivative dyes have a sulfonyl group in the dye molecule and thus exhibit sufficient solubility in purified water and commonly used solvents for hair dyes. Therefore, even if stored for a long time on the hair dye base there is no problem such as precipitation or discoloration is excellent in stability. In addition, since the molecular weight is greater than that of the nitro-based dyes, the color persistence against water drainage is superior to that of the nitro-based dyes.

The amount of 4-amino pyridine azo derivative dye contained in the dyeing agent composition for oxidation dyeing of the present invention is preferably 0.001 to 10% by weight, more preferably 0.05 to 4% by weight, in consideration of color development, stability and solubility.

The dyeing agent composition for oxidation dyeing of the present invention contains an oxidized dye precursor and a coupler, and preferably contains two or more oxidized dye precursors and a coupler.

Oxide dye precursors and couplers can use most of the currently known oxide dye intermediates and couplers. Such oxidizing dye precursors include o-aminophenol, p-aminophenol, toluene-2,5-diamine hydrochloride, p-phenylenediamine hydrochloride, toluene-2,5-diamine, p-phenylenediamine, and p- sulfate Methylaminophenol, sulfate o-aminophenol, sulfate p-aminophenol, toluene-2,5-diamine sulfate, p-phenylenediamine sulfate, etc. are mentioned, and the compounding quantity of an oxide dye precursor is 0.05-5 weight% ( When present as a salt, it is preferable as a free base, More preferably, it is 0.25 to 1.5 weight%. Couplers include 2-methyl-5-hydroxyethyl aminophenol, p-amino-o-cresol, m-aminophenol, 2,4-diaminophenoxyethanol hydrochloride, m-phenylenediamine hydrochloride, m- Phenylenediamine, N-methyl-p-phenylenediamine, p-amino-o-cresol sulfate, 4-ethoxy-m-phenylenediamine sulfate, m-phenylenediamine sulfate, α-naphthol, resorcy Knoll, 2-methylsorbinol, etc. are mentioned.

In addition, the dyestuff composition for oxidation dyeing of the present invention may be further added to the dyes commonly used within the range that does not impair the object of the present invention, such as arianol dye, p-nitro -o-phenylenediamine, nitro-p-phenylenediamine, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, nitro-p-phenylenediamine hydrochloride, picramic acid and other vegetable dyes (Henna) and the like.

 The dyeing agent composition for oxidation dyeing of the present invention can be used in the pH range of neutral to alkali, and it is particularly effective to use in alkaline conditions.

In the dyeing agent composition for oxidation dyeing of the present invention, components commonly used in hair dyeing agents can be used within a range not impairing the effects of the present invention. For example, ammonia, monoethanolamine and aminomethylpropanol may be used as the alkali agent, and nonionic surfactants or alkyldieethanolamides may be used as thickeners, and as surfactants, cationic, anionic or nonionic surfactants may be used. Can be used. Moreover, quaternary ammonium salt, a quaternization polymer, etc. can be used as a conditioning agent. Such hair dye compositions are prepared in suitable formulations, such as creams, gels, liquids, etc. using appropriate ingredients.

The hair dye composition for oxidation dyeing of the present invention thus prepared is mixed with an oxidizing agent such as, for example, 6% hydrogen peroxide immediately before dyeing, and applied to the hair, and after 20 to 40 minutes of treatment, it is rinsed with a conventional shampoo and water. Dyeing can be performed. Such methods are described in detail in Keith C. Brown and Stanley Pohl, "Permanent Hair Dyes (1996, Society of Cosmetic Chemists)".

Hereinafter, the present invention will be described in detail with reference to Examples. However, embodiments according to the present invention can be modified in many different forms, the scope of the present invention should not be construed as limited to the embodiments described below. Embodiments of the present invention are provided to more completely explain the present invention to those skilled in the art.

Examples 1-3 and Comparative Examples 1-2

According to the composition ratio shown in Table 1, dye, propylene glycol, sodium sulfite, EDTA.4Na, dimethicone copolyol, oleic acid, and oleyl alcohol were added to purified water, and the mixture was emulsified by heating to 80 ° C. Subsequently, the mixture was cooled to 40 ° C., monoethanolamine, strong ammonia water (28%), and a flavoring agent were added and mixed uniformly to prepare a dye-dye composition for oxidation dyeing.

Ingredient Name (wt%) Comparative example Example One 2 One 2 3 Oleic acid 21.00 21.00 21.00 21.00 21.00 Sodium Lauryl Sulfate 2.00 2.00 2.00 2.00 2.00 Oleyl alcohol 10.00 10.00 10.00 10.00 10.00 Strong ammonia water (28%) 5.50 5.50 5.50 5.50 5.50 Isopropyl Alcohol 10.00 10.00 10.00 10.00 10.00 Propylene glycol 5.00 5.00 5.00 5.00 5.00 Sodium sulfite 0.70 0.70 0.70 0.70 0.70 Monoethanolamine 3.20 3.20 3.20 3.20 3.20 EDTA.4Na 0.20 0.20 0.20 0.20 0.20 Dimethicone Copolyol 0.50 0.50 0.50 0.50 0.50 p-nitro-o-phenylenediamine - 0.20 - - - 4-amino pyridine azo derivative dye ¹⁾ - - 0.20 - 0.10 4-amino pyridine azo derivative dye ²⁾ - - - 0.20 0.10 p-phenylenediamine 0.070 0.070 0.070 0.070 0.070 P-toluenediamine sulfate 0.095 0.095 0.095 0.095 0.095 Resorcinol 0.250 0.250 0.250 0.250 0.250 p-aminophenol 0.325 0.325 0.325 0.325 0.325 p-amino-o-cresol 0.295 0.295 0.295 0.295 0.295 2-methyl-5-hydroxyethylaminophenol 0.150 0.150 0.150 0.150 0.150 Purified water to 100 to 100 to 100 to 100 to 100 pH 10.5 10.4 10.3 10.3 10.4

In Table 1, R of 4-amino pyridine azo derivative dye ¹⁾ of Formula 1 is C ₂ H _5, and R of 4-amino pyridine azo derivative dye ²⁾ of Formula 2 is CH ₃ .

Yellow and orange color development, stability, and color persistence due to water fall by the oxidation dyeing hair dye compositions prepared according to Examples and Comparative Examples were evaluated through the following test.

<Evaluation of color persistence by yellow and orange color development, stability and water drop>

The hair dye composition for dyeing oxide prepared according to the above Examples and Comparative Examples was mixed 1: 1 with 6% hydrogen peroxide solution and then applied to experimental human hair, and after 30 minutes, washed with shampoo and dried. The difference in color development power on the hair for yellow and orange after drying was evaluated by seven expert panelists according to the following criteria and the results are shown in Table 2.

In addition, the dyeing agent composition for oxidation dyeing of Examples and Comparative Examples was left in a 50 ℃ thermostat and observed for 2 months to evaluate the stability with high temperature according to the following criteria and the results are shown in Table 2.

(Evaluation standard)

* Color development

◎: excellent color development ability ○: good color development ability, △: color development power slightly weak, X: color development power weak

 *stability

◎: No dye precipitation or discoloration, ○: No discoloration, but dye slightly precipitated, △: Dye precipitation severe, X: Dye precipitation and dye color discoloration

Comparative Example 1 Comparative Example 2 Example 1 Example 2 Example 3 Yellow and orange color development △ ◎ ◎ ◎ ◎ stability ◎ X ◎ ◎ ◎

In addition, the dyeing composition for the oxidation dyeing dye of the Examples and Comparative Examples was dyed in hair and wool for shampoo fastness test, and then put in a 40% SLES 1% aqueous solution and stirred for 20 minutes, and this process was repeated twice and shampoo fastness (water Omission). Differences in hair color before and after dripping were evaluated according to the following criteria by 7 professional panelists, and the color difference of wool was measured using a color and color difference meter (model 1000DPS, Nippon denshoku kogyo Co., LTD). Table 3 shows.

(Evaluation standard)

◎: less color difference after drowning, ○: some color difference, △: severe color difference, X: very severe color difference

 division Comparative Example 1 Comparative Example 2 Example 1 Example 2 Example 3 The color difference of hair ○ △ ○ ○ ◎ L ** -15.7 -14.8 -11.2 -12.3 -10.5 a ** 7.8 6.9 4.2 3.8 2.5 b ** -0.2 -5.2 -2.3 -1.5 -0.8 △ E ** 17.2 17.1 12.1 13.0 10.8

In Table 3, ** indicates the difference between the color values before and after the water drainage (the value obtained by subtracting the value after the water draining).

L **: Brighter and darker, the higher the value, the brighter

a **: Green to red, the bigger the red group

b **: Blue to yellow, the bigger the yellow group.

ΔE **: transition energy, ΔE = [(Δa) ² + (Δb) ² + (ΔL) ² ] ^1/2

Referring to Tables 2 and 3 above, when dyed with a dyeing agent composition for oxidation dyeing containing 4-amino pyridine azo derivative of the present invention, it is not only excellent in long-term stability and color persistence due to water drop, but also yellow or orange The color developing power of was found to be comparably good as in Comparative Example 2 containing p-nitro-o-phenylenediamine which is a nitro-based direct dye.

On the other hand, the hair dye composition of Comparative Example 1, which does not contain the 4-amino pyridine azo derivative of the present invention, the stability and color persistence due to water drainage during dyeing is good, but it can be seen that the color development ability against yellow and orange is weak. have. In addition, the hair dye composition of Comparative Example 2 containing p-nitro-o-phenylenediamine, which is a nitro-based direct dye, has good yellow or orange color development ability, but it has been found to have poor stability over time and color persistence due to water drainage. .

As such, the dyeing agent composition for oxidation dyeing of the present invention containing 4-amino pyridine azo derivative not only sufficiently develops yellow and orange colors to obtain a desired color, but also has high stability over time, causing dyes to precipitate or discolor even when stored for a long time. This does not happen. In addition, the color persistence against water drainage is also very good, so that the dyeing effect can be maintained for a long time.

Claims (3)

A hair dye composition containing an oxidized dye precursor and a coupler, comprising any one of 4-amino pyridine azo derivatives selected from the group consisting of a compound represented by the following formula (1), a compound represented by the following formula (2), and mixtures thereof A hair dye composition for oxidation dyeing, characterized in that; <Formula 1>

<Formula 2>

In Formulas 1 and 2, R is independently an alkyl group having 1 to 4 carbon atoms, a hydroxy alkyl group, a carboxyl group-containing alkyl group or a sulfonyl group-containing alkyl group. According to claim 1, wherein the content of the 4-amino pyridine azo derivative is 0.001 to 10% by weight based on the total weight of the hair dye composition, hair dye composition for oxidation dyeing. The hair dye composition for oxidation dyeing according to claim 1, wherein the hair dye composition is alkaline.