KR20060014315A - Composition for permanent oxidative dyeing of hair - Google Patents

Abstract

The present invention relates to an oxidative permanent hair dye composition containing an oxidized dye precursor and a coupler, wherein the hair dye composition according to the present invention contains a quaternary ammonium compound and an anionic surfactant. The oxidative permanent hair dye composition of the present invention is excellent in the conditioning effect of hair after dyeing, and effectively removes contaminants such as dye solution remaining in hair, scalp, skin, etc., and also has excellent color persistence.

Oxidation permanent hair dye * Quaternary ammonium compound * Anionic surfactant

Description

Composition for permanent oxidative dyeing of hair

The present invention relates to an oxidative permanent hair dye composition containing an oxidized dye precursor and a coupler, and more particularly, excellent in the conditioning effect of hair after dyeing, and effectively removing contaminants such as dye solution remaining in hair, scalp, skin, and the like. In addition, the present invention relates to an oxidative permanent hair dye composition having excellent color sustainability.

The oxidative permanent hair dye composition typically contains at least one oxide dye precursor and at least one coupler which oxidizes to form a dye, which is mixed with an oxidizing agent, such as a hydrogen peroxide solution or the like diluted just before application to the hair. Dyeing is performed. 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, when dyeing using oxidative permanent hair dyes currently on the market, hair damage easily occurs due to the components of the hair dye. In order to prevent such hair damage, compounds having a cation such as a cationic surfactant have been mainly used. These cationic compounds are adsorbed on damaged hair to reduce friction, increase the hair adsorption of other water-insoluble conditioning materials, and also change the electrical properties of the hair to reduce static electricity.

However, as the amount of these cationic compounds increases, the formation of precipitates or storage stability is reduced by interacting with anionic or nonionic surfactants in the hair dye, and the hair deposition rate of the dye is increased, thereby increasing the scalp or skin. Contamination is easily achieved, and unreacted dyes are not washed well after dyeing, which causes problems such as stiff hair and poor treatment effect.

Therefore, the technical problem to be achieved by the present invention is to solve the problems as described above, it is excellent in the conditioning effect of the hair after dyeing, as well as effectively remove contaminants such as dye solution remaining in the hair, scalp, skin, etc. In addition, the present invention provides an oxidative permanent hair dye composition having excellent color sustainability.

In order to achieve the above technical problem, the present invention in the hair dye composition containing an oxidized dye precursor and a coupler, an oxidative permanent hair dye composition comprising a quaternary ammonium compound represented by the formula (1) and an anionic surfactant to provide.                     

In Formula 1, R ₁ is any one selected from the group consisting of a straight alkyl group having 12 to 18 carbon atoms, a branched alkyl group, and an alkenyl group, R ₂ and R ₃ are independently an alkyl group having 1 to 3 carbon atoms, R ₄ is (CH ₂ CHOHCH ₂ O) _n H, n is 1 to 10, and X is any one selected from the group consisting of a halogen group element, a sulfate group and an acetate group.

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

The oxidative permanent hair dye composition of the present invention simultaneously contains a quaternary ammonium compound and an anionic surfactant.

The quaternary ammonium compound and the anionic surfactant form a mixed micelle that is usually soluble in an aqueous solution called pseudo-nonionic complex surfactant. These pseudo-nonionic composite surfactants, like conventional nonionic surfactants, have more hydrophilic groups, so that their solubility in water increases. These pseudo-nonionic complex surfactants improve the disadvantage that the effect of each component is not exhibited by forming precipitates when cationic compounds such as quaternary ammonium compounds are used simultaneously with nonionic surfactants or anionic surfactants. give. If conditions such as structure and mixing concentration of the anionic surfactant and cationic compound forming the pseudo-nonionic complex surfactant are well controlled, the surfactant activity, for example, solubilizing power, cleaning power, emulsifying power, dispersing power, surface Excellent effect can be obtained in the ability to lower tension and low cmc concentration.

In the present invention, the quaternary ammonium compound is a structure of Chemical Formula 1 described above, in which all four substituents of ammonium ions are composed of alkyl groups and the like. These quaternary ammonium compounds adsorb to damaged hair to reduce friction, increase hair adsorption of other water-insoluble conditioning materials, and reduce hair static.

In the present invention, the quaternary ammonium compound has one or more hydrophilic groups in the substituent, and the hydrophilic group is a structure in which one or more glyceryl groups are condensed and repeated, and the number of repeating units is 1 to 10.

Here, the number of repeating units represents the number of moles of the added glyceryl group, and is selected by adjusting the number of added moles according to the use thereof.

In the hair dye composition according to the present invention, the content of the quaternary ammonium compound is preferably 0.01 to 20% by weight, more preferably 0.1 to 10% by weight based on the total weight of the composition. This is because, when the content is less than 0.01% by weight, the conditioning effect is insignificant, and when the content is more than 20% by weight, there is no obvious effect increase.

The hair dye composition according to the present invention includes an anionic surfactant together with the quaternary ammonium compound. Such anionic surfactant is not particularly limited as long as it can be used to form a pseudo-nonionic complex surfactant with the quaternary ammonium compound as commonly used in hair dyes. That is, the anionic surfactant may be generally applied to all widely used anionic surfactant compounds, carboxylate compounds such as soap, higher alcohols, higher alkyl ethers, sulfate esters of sulfates (olefins) ( sulfuric ester) salt compounds, sulfate compounds containing alkylbenzensulfonate, phosphate compounds phosphorylated with higher alcohols, and the like. More specifically, sodium lauryl sulfate (hereinafter referred to as 'SLS'), sodium lauryl ether sulfate (SLES), linear alkylbenzenesulfonate (LAS), monoalkyl phosphate (MAP), acyl isethio At least one selected from the group consisting of acyl isethionate (SCI), alkyl glyceryl ether sulfonate (AGES), acyl glutamate, acyl taurate, and fatty acid metal salts. It is preferable, but not limited thereto. It is more preferable to use SLS, SLES, LAS, or SCI among these. Here, carboxylate compounds such as soap are composed of alkyl chains of C12 to C18.

The content of the anionic surfactant is preferably 0.01 to 20% by weight, more preferably 0.1 to 10% by weight based on the total weight of the composition.

In the present invention, it is preferable that the mixing ratio of the quaternary ammonium compound and the anionic surfactant is 0.01: 1 to 1: 1 by weight. This is because when the ratio is less than 0.01: 1, it is difficult to see the effects of conditioning and detergency, and mixing more than 1: 1 decreases the feeling of use and physical properties.

The oxidative permanent hair dye composition of the present invention contains a conventional oxidized dye precursor and coupler used in the oxidized permanent hair dye composition, and preferably contains two or more oxidized dye precursors and couplers.

Oxide dye precursors and couplers may use most of the known oxide dye precursors 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, o-aminophenol sulfate, p-aminophenol sulfate, toluene-2,5-diamine sulfate, p-phenylenediamine sulfate, and the like, but are not limited thereto. These can be used individually or in mixture of 2 or more types.

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, resorcin, 2-methyl sorbinol, etc. are mentioned, It is not limited to this. They are used in admixture with the oxidizing dye precursors above and can exhibit a variety of shades in the hair.

The content of the mixture of the oxidized dye precursor and the coupler is preferably used by 0.05 to 10% by weight, more preferably 0.1 to 5.0% by weight based on the total weight of the composition.

In the oxidative permanent hair dye composition of the present invention, a direct dye commonly used within a range that does not impair the object of the present invention may be further added. Such direct dyes include azo dyes, anthraquinone dyes, and nitro derivatives of benzene groups. , Indamine, indoaniline, indophenol, and the like.

The hair dye composition of the present invention can be used within the range that does not impair the effects of the present invention, components commonly used in hair dyes. For example, solvents, antioxidants, thickeners, alkalis, metal sequestrants, oxidants, and fragrances are used.

As a water-soluble solvent which can be used in this invention, ethanol, propyl alcohol, isopropyl alcohol, glycol, and glycol ether, such as propylene glycol, hexylene glycol, and dieglycol, can be used individually or in mixture. Usable content is from 0.01 to 20% by weight, more preferably from 0.5 to 15% by weight, based on the total weight of the composition.

The alkali agent is not particularly limited as long as it can be used for the hair dye as having a pH of 6 or more, for example, sodium hydroxide, potassium hydroxide, ammonia water, monoethanolamine, aminomethylpropanol and the like. Such alkaline agents more preferably have a pH in the range of 6-12.

In addition, the antioxidant is not particularly limited as long as it can be commonly used in hair dyes, for example, ascorbic acid, erythorbic acid, cysteine hydrochloride, sodium sulfite and the like. The preferred content is 0.01 to 10% by weight, more preferably 0.1 to 3% by weight, based on the total weight of the composition.

The metal containment agent is not particularly limited as long as it can be commonly used in hair dyes, and examples thereof include, but are not limited to, idieti, tetrasodium idieti, pentasodium pentate, and the like. The preferred content is 0.01 to 5% by weight, more preferably 0.05 to 1% by weight, based on the total weight of the composition.

Such hair dye compositions can be formulated into suitable formulations such as cream, gel, liquid, aerosol, etc. using appropriate ingredients.

As the oxidizing agent to be mixed with the composition according to the present invention, hydrogen peroxide water (35%) is generally used.

How to use the hair dye composition according to the present invention is as follows. The hair dye composition of the present invention is mixed with an oxidizing agent containing peroxide, for example 6% hydrogen peroxide immediately before use, applied to the hair, treated for 5 to 20 minutes, and then rinsed with conventional shampoo and water. Their details are detailed in the literature, such as "Permanent Hair Dyes" by Keith C. Brown and Stanley Pohl (1996, Society of Cosmetic Chemists).

As described above, the hair dye composition according to the present invention forms quasi-nonionic complex surfactant by using the quaternary ammonium compound together with an anionic surfactant, which is excellent in the conditioning effect and remains on the scalp or scalp after dyeing. Not only can the skin contaminants such as hair dye solution be easily removed, but the color lasting power of hair dye is also excellent.

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 fully describe the present invention to those skilled in the art.

Synthesis Example

As a quaternary ammonium compound to change the physical properties of the anionic surfactant in a mixed system with an anionic surfactant, a mono-type including one quaternary ammonium group was synthesized in the following manner. The following examples are intended to illustrate the invention in detail, but these examples do not limit the technical scope of the invention.

Synthesis of N, N-Dimethyl-N-Monoglyceryl Lauryl Ammonium Chloride

Isopropyl alcohol (IPA; 120 g), dodecyl dimethylamine (315 g, 1.4 mol), 1-chloro-2,3-propanediol (166 g, 1.47 mol) were added to a three-necked flask, and sodium iodide was used as a catalyst. (sodium iodide) (2.4 g) was added followed by reflux. The reaction progress was checked by measuring the amine%. The reaction proceeded for 95 hours after raising the temperature of the reactor to 120 ° C. for 10 hours. The reaction product was poured into acetone, cooled and recrystallized. Since the result was hygroscopic, the result obtained through the manure after recrystallization was immediately dried in vacuo.

Synthesis of N, N-Dimethyl-N-Diglyceryl Lauryl Ammonium Chloride

In order to synthesize the diglyceryl compound in which two glyceryl groups were substituted, the glyceryl group was further introduced in the monoglyceryl compound.

Isopropyl alcohol (IPA; 140 g), a monoglyceryl compound (227 g, 0.7 mol) and glycidol (61 g, 96%, 0.7 mol) were added to a three-necked flask, followed by stirring at 50 ° C. for 1 hour. Completed. Isopropyl alcohol was removed from the mixture by distillation under reduced pressure. Since the result was hygroscopic, the result was stored as a 50% solution in distilled water.

Comparative Examples 1 to 6 and Examples 1 to 6

In the following Table 1 (Comparative Examples 1 to 6) and 2 (Examples 1 to 6), a hair dye composition was prepared in the same manner as the components.

Steatimonium chloride and polyquaternium were used as a conventional cationic compound in the hair dye composition of Table 1 as a comparative example. In addition, as a quaternary ammonium compound contained in the hair dye composition of Table 2 as an example, N, N, N-dimethyl (tetraglyceryl) dodecylammonium chloride (DTDAC), which is a cationic compound of Formula 2, was used. As the anionic surfactant, sodium lauryl sulfate and sodium laurate were used.

In Chemical Formula 2, R is C ₁₂ H ₂₅ .

The hair dye compositions of Table 1 and Table 2 are prepared by dissolving raw materials 1 to 7 at about 75 to 80 ° C. with an oil phase and warming and dissolving raw materials 8 to 15 and 19 at about 75 to 80 ° C. by mixing the aqueous phase and the oil phase at the same temperature. Emulsification was performed, and the mixture was cooled to about 45 ° C., and the remaining raw materials 16 to 18 were added thereto, followed by mixing and stirring to complete the preparation.                     

On the other hand, the oxidizing agent as the second agent, according to the ingredients and contents shown in Table 3, the raw materials 1 to 7 are heated and dissolved in about 75 ~ 80 ℃ in the oil phase and the raw materials 8, 11 by about 75 to 80 ℃ heated dissolved in the water phase and oil phase The mixture was emulsified at the same temperature, cooled to about 45 ℃ to add the remaining raw materials 9, 10 and uniformly mixed and stirred to complete the production.

Test Example 1: Hair Conditioning and Staining Effects

50 women were randomly selected and divided into 10 groups of 5 people each. After dyeing with the compositions according to the examples and comparative examples prepared above, the conditioning effect of the hair was observed and the persistence of the dyed color was observed after 1 month. For dyeing, the hair dye composition according to Tables 1 to 2 and the oxidizing agent of Table 3 were mixed at the same content ratio, applied to the hair, left for about 30 minutes, and then rinsed out the mixed solution in running water. Observation of the conditioning effect and duration of staining of the hair was assessed sensory by a randomly selected 5 expert group.

Evaluation criteria for the conditioning effect is shown in Table 4 below, and the evaluation results are shown in Table 5 below.

Wet grade Dry Very smooth 5 Very smooth Smooth 4 Smooth is average 3 is average Slightly jammed 2 crudity Severely jammed One Very rough

division Comparative example Example One 2 3 4 5 6 One 2 3 4 5 6 Wet 3.4 3.5 2.8 2.9 2.8 3.0 3.9 4.0 4.2 3.9 4.0 4.3 Dry 3.2 3.3 2.9 2.9 2.9 2.9 3.8 3.9 4.0 3.7 4.0 4.0

Referring to Table 5, compared to Comparative Examples 1 to 6 when the conventional cationic compound is used alone, in Examples 1 to 6 using the quaternary ammonium compound represented by Formula 2 and an anionic surfactant The conditioning effect rose further. In addition, in the Examples, the effect of the quaternary ammonium compound represented by the formula 2 was increased, the results were further increased. On the other hand, Comparative Examples 3 to 6, in which a conventional cationic compound was mixed with an anionic surfactant, showed that the conditioning effect was further reduced.

On the other hand, the results of the dyeing sustainability evaluation test after about one month is shown in Table 6.

division Comparative example Example One 2 3 4 5 6 One 2 3 4 5 6 Dying ○ ○ △ △ △ △ ○ ◎ ◎ ○ ◎ ◎

(Evaluation standard)                     

◎: less color difference after dripping

○: some color differences

△: severe color difference

Referring to Table 6, the colors of Examples 1 to 6 remain more vivid, and as the content of the quaternary ammonium compound represented by Formula 2 increases, the color remains even more vivid. Indicated.

Test Example 2: Detergency Test

The washing power was compared for the hair dye. Here, the cleaning power means that the mixed solution of the first and second hair dyes remaining on the hair after dyeing is rinsed well and the oxidative dye remaining on the surface of the hair is removed well.

The composition according to the examples and comparative examples prepared in Table 1 or Table 2 and the content according to the ratio of the same content as well as the ratio of the oxidizing agent of Table 3 well dyed in wool, after 30 minutes 1 Rinse well for a minute and colorize. Subsequently, a shampoo test was conducted for the purpose of the detergency test as follows. Soak in 1% solution of Sodium Lauryl Sulfate (SLES) at 40 ° C and leave for 10 minutes, take it out, rinse well in flowing water, put it in the dryer, and dry it using a colorimeter to measure color (L, a, b, ΔE). It was. The difference in the actual color difference was interpreted as the value of ΔE.

The procedure was repeated five times. The colorimetry was performed three times each, and the average value was obtained.                     

(Difference in hair color before and after dripping)

◎: less color difference after dripping

○: some color differences

△: severe color difference

×: very different color difference

Referring to Table 7, the hair dye composition including the quaternary ammonium compound represented by the formula (2) and the anionic surfactant as in Examples 1 to 6, compared with the case of using the conventional cationic compounds of Comparative Examples 1 to 6 There was less difference in color in the initial one run.

These test results indicate that when using the quaternary ammonium compound represented by the formula (2) and anionic surfactant, when washing the mixed solution after dyeing, unreacted dyes remaining on the surface of the wool cloth and dyes that did not penetrate to the inside of the wool It is easily rinsed, and thus, when the shampoo solution is tested, the difference in color difference between before and after the test is small. On the other hand, Comparative Examples 3 to 6, in which a common cationic compound was mixed with an anionic surfactant, were dyed well after dyeing, as compared to the case of using a cationic compound alone as in Comparative Examples 1 to 2 of the Comparative Examples. In the shampoo test, the initial one-time test resulted in less color difference.

In addition, the experimental results of Table 7 were observed to further retain the color in the hair dye composition containing the quaternary ammonium compound represented by the formula (2) and anionic surfactant as in Examples 1 to 6.

Test Example 3 Skin Contamination Reduction

In the hair dye, the effect of reducing skin contamination was performed. A mixed solution of 1, 2 drugs was prepared, and 20 minutes after the mixed solution was applied to the arm of five arbitrarily selected panelists, the skin was washed twice with soap for sensory evaluation of skin contamination. Some of the comparative examples and the examples were selected and carried out. The evaluation results are shown in Table 8 below.

division Comparative Example 1 Comparative Example 2 Example 1 Example 2 Example 3 Skin Contamination Reduction △ △ ◎ ◎ ◎

(Evaluation standard)

◎: Easily erased, ○: Somewhat remaining, △: Not easily erased

Test evaluation results Comparative Examples 1 to 2 containing a conventional cationic compound are not easily cleared, but Examples 1 to 3 containing a quaternary ammonium compound represented by the formula (2) and an anionic surfactant are easily erased. Indicated.

As described above, the hair dye composition according to the present invention includes a quaternary ammonium compound represented by Chemical Formula 2 and an anionic surfactant, thereby imparting excellent conditioning effect and long-lasting effect on dyeing hair after dyeing. Excellent cleaning power effectively removes dyes remaining on the surface of hair and dyes on the scalp after dyeing.

The oxidative permanent hair dye composition according to the present invention contains a quaternary ammonium compound and an anionic surfactant, which is excellent in conditioning the hair after dyeing, and effectively removes contaminants such as dye solution remaining on the hair, scalp, skin, and the like. It also has excellent color persistence.

Claims (5)

An hair dye composition comprising an oxidized dye precursor and a coupler, comprising: a quaternary ammonium compound represented by the following formula (1) and an anionic surfactant; <Formula 1>

In Formula 1, R ₁ is any one selected from the group consisting of a straight alkyl group having 12 to 18 carbon atoms, a branched alkyl group, and an alkenyl group, R ₂ and R ₃ are independently an alkyl group having 1 to 3 carbon atoms, R ₄ is (CH ₂ CHOHCH ₂ O) _n H, n is 1 to 10, and X is any one selected from the group consisting of halogenated elements, sulfate groups, and acetate groups. The method of claim 1, wherein the anionic surfactant is sodium lauryl sulfate (SLS), sodium lauryl ether sulfate (SLES), linear alkylbenzenesulfonate (LAS), monoalkyl phosphate (MAP), acyl isethionate (acyl) isethionate, SCI), alkyl glyceryl ether sulfonate (AGES), acyl glutamate, acyl taurate, and at least one selected from the group consisting of fatty acid metal salts. Oxidation permanent hair dye composition. The oxidative permanent hair dye composition according to claim 1, wherein the content of the quaternary ammonium compound is 0.01 to 20% by weight, and the content of the anionic surfactant is 0.01 to 20% by weight. The oxidative permanent hair dye composition according to claim 1, wherein the mixing ratio of the quaternary ammonium compound and the anionic surfactant is 0.01: 1 to 1: 1 by weight. The oxidative permanent hair dye composition of claim 1, wherein the mixture of the oxidized dye precursor and the coupler is 0.05 to 10 wt% based on the total weight of the composition.