JP3190792B2 - Hair deformant composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hair deforming composition which is excellent in high moisture resistance, can be straightened without damaging curly hair, has an excellent sustaining effect, and is useful as a shampoo, a hair treatment and the like. .

[0002]

2. Description of the Related Art Permanent wave (hereinafter referred to as "perm") is widely used as a method for straightening and straightening curly hair. By applying a composition containing a reducing agent such as thioglycolic acid or cysteine to the hair, the perm cleaves the S--S bond of the hair keratin protein under alkaline conditions, and then oxidizes sodium bromoate or the like. The hair is semi-permanently deformed by being recombined by applying an agent.

[0003] On the other hand, as a method of temporarily straightening the curly hair, a method using a commercially available hair care agent for the curly hair,
There is a blow method by a hairdresser. The hair care agent for curly hair is a method that uses a mild reducing agent, oxidizing agent, etc., and the blow method temporarily cuts hydrogen atom bonds in hair and then forcibly forms other hydrogen atom bonds by blowing Is the way.

[0004]

However, since the hair setting mechanism in perm cleaves and recombines the S--S bond of keratin protein in the hair, this treatment weakens the keratin protein in the hair. I will. Such weakened hair is easily damaged by physical external forces such as brushing. On the other hand, the hair care agent for hazy hair uses a mild reducing agent and an oxidizing agent, so that a sufficient straightening effect cannot be obtained. Further, the blow method cannot be easily performed at home, and the set is easily broken under high humidity.

Accordingly, the present invention solves the above-mentioned problems, has excellent high humidity resistance, can be deformed without damaging the curly hair,
Moreover, it is an object of the present invention to provide a hair deforming composition capable of maintaining the deformation for a long period of time.

[0006]

Means for Solving the Problems As a result of intensive studies, the present inventors have found that a combination of a specific organic acid and a sulfonic acid is combined, and that both components are penetrated into the hair by an organic solvent used in combination, so that the curly hair deforming action (set Power), and found that there was no damage to the hair in that case, and also found that the deformation effect was not lost even by humidity or repeated washing, and the present invention was completed.

That is, the present invention relates to (a) organic acids of benzoic acid, hexanoic acid, heptanoic acid, 2-hydroxyhexanoic acid, salicylic acid, naphthalene carboxylic acid, naphthalenedicarboxylic acid, and pyrrolidone carboxylic acid, and salts thereof. Or more, (b) 1-pentanesulfonic acid, 1-
Hexanesulfonic acid, 1-heptanesulfonic acid, 1-octanesulfonic acid, isethionic acid, 3-hydroxypropanesulfonic acid, 4-hydroxybutanesulfonic acid, 5
-Hydroxypentanesulfonic acid, 6-hydroxyhexanesulfonic acid, 7-hydroxyheptanesulfonic acid,
Benzenesulfonic acid, o-toluenesulfonic acid, m-toluenesulfonic acid, p-toluenesulfonic acid, 1- or 2-naphthalenesulfonic acid, 2,7-naphthalenedisulfonic acid, 1,5-naphthalenedisulfonic acid, 2,6 -Naphthalenedisulfonic acid, 1,3,6-naphthalenetrisulfonic acid, 1-naphthol-2-sulfonic acid, 1-naphthol-4-sulfonic acid, 2-naphthol-6-sulfonic acid, 2-naphthol-7-sulfone Acid, 1-naphthol-3,6-disulfonic acid, 2-naphthol-6,8-
Disulfonic acid, 2,3-dihydroxynaphthalene-6
Sulfonic acid, 1,7-dihydroxynaphthalene-3-sulfonic acid, 4,5-dihydroxynaphthalene-2,7-
An object of the present invention is to provide a hair deforming composition comprising at least one selected from sulfonic acids of disulfonic acid and salts thereof, and (c) an organic solvent, which is acidic.

[0008]

[0009]

[0010]

[0011]

[0012]

[0013]

[0014]

[0015]

[0016]

[0017]

[0018]

[0019]

[0020]

[0021]

Further, in the present invention, the organic solvent (c) is represented by the following general formula (c-1):

[0023]

Embedded image

(Wherein, R ⁵¹ represents a hydrogen atom, a methyl group or a methoxy group, R ⁵² and R ⁵³ represent a hydrogen atom or a hydroxyl group, and p, q and r are each an integer of 0-5. (Except when p = q = r = 0 and R ⁵² = R ⁵³ and p = q = r = 0, except when R ⁵¹ is a hydrogen atom and R ⁵² is a hydroxyl group). A hair deforming agent composition having a content of 5 to 50% by weight in the hair deforming agent composition.

The salts of organic acids used in the present invention include alkali metal salts, alkaline earth metal salts, ammonium salts, mono-, di- or tri-C ₁ -C ₆ alkyl ammonium salts,
Mono-, di- or tri C ₁ -C ₆ alkanol ammonium salts and the like can be mentioned, and more preferred salts can be mono or disodium salts, mono or di potassium salts, mono or di ammonium salts and the like. These organic acids or salts thereof can be used alone or in combination of two or more. When used in combination of two or more, hexanoic acid, heptanoic acid, pyrrolidone carboxylic acid,
A combination of two or more selected from 1-naphthalenecarboxylic acid and 2-naphthalenecarboxylic acid is preferred.

The sulfonic acid salt used in the present invention includes an alkali metal salt, an alkaline earth metal salt, an ammonium salt,
Mono-, di- or tri-C ₁ -C ₆ alkyl ammonium salts, mono-, di- or tri-C ₁ -C ₆ alkanol ammonium salts and the like, and more preferred salts are mono or disodium salts, mono or Examples include dipotassium salts, mono- or diammonium salts, and the like. These organic acids or salts thereof can be used alone or in combination of two or more. When two or more kinds are used in combination, 1-hexanesulfonic acid, 1-heptanesulfonic acid, isethionic acid, 3-hydroxypropanesulfonic acid, 4-hydroxybutanesulfonic acid, 5-hydroxypentanesulfonic acid, 6-hydroxy Hexanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid,
1,5-naphthalenedisulfonic acid, 2,6-naphthalenedisulfonic acid, 1,3,6-naphthalenetrisulfonic acid, 1-naphthol-2-sulfonic acid, 1-naphthol-4-sulfonic acid, 2-naphthol-6 Preferred is a combination of two or more selected from -sulfonic acid and 2-naphthol-7-sulfonic acid.

The above organic acids and sulfonic acids have optical isomers due to the presence of an asymmetric carbon atom. In the present invention, both optically active isomers and racemic isomers can be used.

The amount of each of the organic acid or its salt (a) and the sulfonic acid or its salt (b) is preferably 0.1% by weight or more, more preferably 1% by weight or more, in the hair deforming composition. Further, the addition of 1.0 to 20% by weight is preferable because the high humidity resistance is improved and the hair can be deformed with a long lasting effect without damaging the curly hair. The mixing ratio of the organic acid or its salt (a) to the sulfonic acid or its salt (b) is not particularly limited, but is 10: 1 to 1: 1 by weight.
0 is preferred.

The organic solvent (c) used in the present invention is not particularly limited as long as the organic acid or its salt (a) and the sulfonic acid or its salt (b) can penetrate the hair. Those represented by the general formula (c-1) can be mentioned. Examples of such an organic solvent (c) include ethanol, isopropanol, 1-propanol, 1,3-butanediol, hexylene glycol, and the like. These may be used alone or in combination of two or more. it can. When two or more kinds are used in combination, a combination of ethanol and 1-propanol is preferable.

The amount of the organic solvent (c) is preferably 5 to 50% by weight, more preferably 10 to 50% by weight in the hair deforming composition.
-40% by weight, more preferably 20-30% by weight, is preferred because the organic acid or its salt (a) and the sulfonic acid or its salt (b) can penetrate the hair well, and their effects can be sufficiently exhibited.

[0031] In addition to the above-mentioned components, known components of hair cosmetics can be added to the hair deforming composition of the present invention. Such components include surfactants such as alkylbenzene sulfonates, alkyl ether sulfates, olefin sulfonates, α-sulfofatty acid esters, amino acid surfactants, phosphate ester surfactants, and succinic acid esters. Anionic surfactants such as sulfonic acid type surfactants, betaine type surfactants, alkylamine oxides, imidazoline type surfactants, etc .; polyoxyethylene alkyl ethers, polyoxyethylenes Nonionic surfactants such as alkylphenyl ethers, alkanolamides and alkylene oxide adducts thereof, esters of polyhydric alcohols and fatty acids, sorbitan fatty acid esters, alkyl saccharide surfactants; mono- or di-linear long-chains Alkyl quaternary ammonium Unsalted, can be mentioned cationic surfactants such as mono- or di-branched linear long chain alkyl quaternary ammonium salts, they may be used alone or in combination. Among them, when the composition of the present invention is a shampoo, an amino acid-based surfactant, a phosphate ester-based surfactant, and a sufosuccinate-based surfactant are used in consideration of irritation to the skin and hair. It is preferable to use a combination of an imidazoline type surfactant and an alkyl saccharide type surfactant.

The amount of these surfactants is preferably 0.01 to 40.0% by weight, more preferably 0.5 to 20.0% by weight in the hair deforming composition.

In addition, a cationic polymer can be blended to improve the feel of hair and skin. Examples of the cationic polymer include a cationized cellulose derivative, a cationized starch, a cationized guar gum derivative, a diallyl quaternary ammonium salt / acrylamide non-mixture,
Quaternized polyvinylpyrrolidone derivative, polyglycol /
Examples thereof include polyamine condensates, and these can be used alone or in combination of two or more. More specific examples of these cationic polymers include cationized cellulose having a molecular weight of about 100,000 to 3,000,000, cationized starch having a cationization degree of about 0.01 to 1, and a cationization degree of about 0.1 to 1. Cationized guar gum of 01 to 1 (manufactured by Mayhall, Inc .: jaguar, etc.), molecular weight 3
0000 to 2,000,000 diallyl quaternary ammonium salt / acrylamide copolymer, molecular weight 10,000
A polyvinylpyrrolidone / dimethylaminoethyl methacrylate copolymer 4 having a cationic nitrogen content in the vinyl polymer of 1.8 to 2.4% at 0 to 2,000,000
Quaternized polyvinylpyrrolidone derivative such as quaternized product, polyglycol-polyamine condensate having an alkyl group having 6 to 20 carbon atoms, adipic acid / dimethylaminohydroxypropyldiethylenetriamine copolymer (manufactured by Sandos:
Cartaletin, etc.), JP-A-53-139934, page 14, upper left column, line 18 to page 33, lower left column, 2 lines, and JP-A-60-36407, page 8, upper right column, page 17 to upper right column, line 6 And the cationic polymers described in (1).

The amount of the cationic polymer is preferably 0.05 to 20.0% by weight, particularly preferably 0.1 to 10.0% by weight, in the hair deforming composition.

Further, a silicone derivative can be blended to improve the feel of hair and skin. Examples of the silicone derivative include dimethylpolysiloxane, methylphenylpolysiloxane, amino-modified silicone, alcohol-modified silicone, aliphatic alcohol-modified silicone, polyether-modified silicone, epoxy-modified silicone, fluorine-modified silicone, cyclic silicone, and alkyl-modified silicone. Silicone derivatives can be mentioned, and these can be used alone or in combination of two or more. Also, these silicone derivatives,
JP-B-56-38609 (page 1, lower right column, line 10-
(Page 2, upper left column, line 11) can be used as a latex composition emulsion-polymerized by the method described in the above. Among these silicone derivatives, dimethylpolysiloxane having a polymerization degree of 500 or more, polyether-modified silicone, amino-modified silicone, and cyclic silicone are preferable because they can impart a good feeling to hair.

The amount of the silicone derivative is preferably 0.01 to 20.0% by weight, more preferably 0.05 to 10.0% by weight, in the hair deforming composition.

Further, the hair deforming composition of the present invention contains other components which are usually blended in hair cosmetics, for example, higher fatty acid salts having a longer chain than lauric acid, alkylamine oxides, fatty acid alkanolamides, squalane , Lanolin, α-monoisostearyl glyceryl ether, cholesteryl sulfate, etc .; feel improvers; humectants, such as urea; viscosity modifiers, such as methylcellulose, carboxyvinyl polymer, hydroxyethylcellulose, polyoxyethylene glycol distearate; Perfume; pigment; ultraviolet absorber; antioxidant; triclosan;
Fungicides such as trichlorocarban; anti-inflammatory agents such as potassium glycyrrhizinate and tocopherol acetate; anti-dandruff agents such as zinc pyrithione and octopirox; preservatives such as methyl paraben and butyl paraben; A carboxylic acid derivative or the like can be blended within a range that does not impair the purpose of the present invention.

[0038] The dosage form of the hair deforming composition of the present invention is not particularly limited, and it can be made into a desired dosage form such as an aqueous solution, ethanol solution, emulsion, suspension, gel, liquid crystal, aerosol, etc. ,rinse,
It can be applied as a hair treatment, conditioner, blowing agent, foam, lotion, hair cream and the like.

The hair deforming composition of the present invention is acidic, and its pH is preferably adjusted to 2 to less than 7 and particularly adjusted to 2.5 to 6 with an acid or alkali (pH adjuster). Is preferred. When the hair deforming agent composition of the present invention is in the neutral or alkaline region, the deforming effect, the high humidity resistance and the effect of maintaining deformation of the curly hair are reduced.

[0040]

Industrial Applicability The hair deforming composition of the present invention is excellent in the effect of straightening curly hair and does not damage the hair at that time. Also, once the straightened curly hair is left in a high humidity atmosphere and when the hair is washed, the straightened state is not impaired at all, and the hair deforming agent composition of the present invention has excellent high moisture resistance and It also has a lasting effect.

[0041]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the invention is limited thereto.

Examples 1 to 11 and Comparative Examples 1 to 5 Hair deforming compositions having the compositions shown in Table 1 were produced according to a conventional method, and were subjected to the following performance evaluation tests. The results are shown in Table 1.

(Degree of Correction of Curly Hair) 20 curly hairs of a Japanese woman who has never performed cold perm (15c
m), and apply each composition to the hair.
Warmed for hours. Then, it was rinsed with running water and the degree of straightening after drying was evaluated according to the following criteria. ◎: Very good. ：: Excellent. Δ: Neither can be said. X: Inferior.

(High Humidity Resistance) A hair bundle subjected to the same treatment as the correction degree of the habit was transferred to a case where the relative humidity was adjusted to 90% and left for 1 hour. Thereafter, the hair was taken out of the case, and the degree of correction of the habit was measured, and the high-humidity resistance (the degree of change compared to the hair state before being put in the case) was evaluated according to the following criteria. ◎: Very good. ：: Excellent. Δ: Neither can be said. X: Inferior.

(Washing resistance) A hair bundle treated in the same manner as the degree of straightening of a habit was washed with a commercially available shampoo.
Measures the degree of correction of the habit when air dried and the wash resistance (the degree of change compared to the hair condition before shampoo)
Was evaluated. ◎: Very good. ：: Excellent. Δ: Neither can be said. X: Inferior.

[0046]

[Table 1]

As shown in Table 1, in Examples 1 to 11, the curly hair was straightened, and it was kept as it was when left in a high humidity atmosphere and when it was washed. On the other hand, in Comparative Examples 1 to 3, which did not contain any of benzoic acid, benzenesulfonic acid or the organic solvent, the curly hair was hardly corrected, and the slightly corrected portion was left in a high humidity atmosphere. And, when washed, it easily returned to the state before correction. Comparative Example 4 containing benzoic acid and benzenesulfonic acid, but having a content of the organic solvent lower than the lower limit of the preferred amount of the present invention, and Comparative Example 5 in which the pH was not in the acidic region were obtained in Comparative Example 1. 3 was good, but inferior to Examples 1 to 11.

Examples 12 to 67 and Comparative Examples 6 to 26 Ethanol was added to combinations of organic acids and sulfonic acids shown in Table 2 to obtain a hair deforming composition of the present invention. The amounts of the organic acid and the sulfonic acid were 5.0% by weight, the amount of the ethanol was 20% by weight, and the balance was water. The pH was adjusted to 3.0 with an aqueous sodium hydroxide solution. The same test as in Example 1 was performed for each of these hair deformative compositions, and comprehensively evaluated according to the following evaluation criteria. Table 2 shows the results. Table 2 also shows the evaluation results of Comparative Examples 6 to 26 using acetic acid, glycolic acid or 2-hydroxybutyric acid as the organic acid. ◎: Very good. ：: Excellent. Δ: Neither can be said. X: Inferior.

[0049]

[Table 2]

In Examples 12 to 67, the curly hair was straightened, and was kept as it was when left in a high humidity atmosphere and when it was washed.

Example 68 (Shampoo composition) A shampoo composition having the following composition was produced by a conventional method.

Table 3 (Composition) (% by weight) Polyoxyethylene (EO = 2.5) 15.0 Lauryl ether sulfate sodium salt Palm oil fatty acid diethanolamide 3.0 Pyrrolidone carboxylic acid 6.0 1-Naphthalene sulfonic acid 3.5 Ethanol 20.0 Cationic cellulose (molecular weight about 200,000) 0.5 Amino-modified silicone 0.5 (SM8702C; manufactured by Toray Silicone Co., Ltd.) Fragrance 0.2 Dye Trace amount Sodium hydroxide (pH adjuster) Appropriate amount Purified water Balance meter 100.0 This shampoo was excellent in the effect of correcting curly hair by repeated use.

Example 69 (Hair treatment composition) A hair treatment composition having the following composition was produced by a conventional method.

(Composition) (% by weight) Di (2-hexadecyl) dimethylammonium chloride 2.0 Cetyltrimethylammonium chloride 2.5 Lauryltrimethylammonium chloride 2.0 (Myristoylaminoethyl-N-hydroxyethyl) amino- 2-hydroxypropyltrimethylammonium 1.0 pyrrolidonecarboxylic acid 2.0 2,7-dinaphthalenesulfonic acid 2.5 ethanol 15.0 stearic acid 5.0 polyoxyethylene (EO = 5) oleyl ether 0.4 dimethylpoly Siloxane (degree of polymerization 1000) 0.5 1 mol adduct of pentaerythritol glyceryl / isostearyl glycidyl ether 0.1 benzyloxyethanol 0.3 diethylene glycol monoethyl ether 5.0 hydroxyethyl Cellulose (1% aqueous solution; viscosity 8000 cP) 0.3 Methylparaben 0.2 Perfume 0.2 Sodium hydroxide (pH adjustment agent) qs Purified water Balance Total 100.0 The hair treatment composition is excellent straightening effect of habit In addition, smoothness and flexibility could be imparted to the hair, and the oily feeling was also small, so that the hair could be made moist.

Example 70 Instead of ethanol of Example 9, isopropanol was used.
A hair treatment composition was obtained in the same manner as in Example 9, except that the same amount of 1-propanol, 1,3-butanediol or hexylene glycol was used. This hair treatment composition was excellent in the effect of straightening the curly hair, was able to impart smoothness and flexibility to the hair, was less oily, and was able to give the hair a moist touch.

────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-5-43425 (JP, A) JP-A-5-320029 (JP, A) JP-A-6-340523 (JP, A) JP-A-6-340523 298625 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) A61K ^7/ 00-7/50

Claims (3)

(57) [Claims] 1. (a) at least one selected from organic acids of benzoic acid, hexanoic acid, heptanoic acid, 2-hydroxyhexanoic acid, salicylic acid, naphthalenecarboxylic acid, naphthalenedicarboxylic acid and pyrrolidonecarboxylic acid and salts thereof,
(B) 1-pentanesulfonic acid, 1-hexanesulfonic acid, 1-heptanesulfonic acid, 1-octanesulfonic acid, isethionic acid, 3-hydroxypropanesulfonic acid, 4-hydroxybutanesulfonic acid, 5-hydroxypentanesulfonic acid 6-hydroxyhexanesulfonic acid, 7-hydroxyheptanesulfonic acid, benzenesulfonic acid, o-toluenesulfonic acid, m-toluenesulfonic acid, p-toluenesulfonic acid, 1- or 2-naphthalenesulfonic acid, 2,7- Naphthalenedisulfonic acid, 1,
5-naphthalenedisulfonic acid, 2,6-naphthalenedisulfonic acid, 1,3,6-naphthalenetrisulfonic acid, 1
-Naphthol-2-sulfonic acid, 1-naphthol-4-
Sulfonic acid, 2-naphthol-6-sulfonic acid, 2-naphthol-7-sulfonic acid, 1-naphthol-3,6-
Disulfonic acid, 2-naphthol-6,8-disulfonic acid, 2,3-dihydroxynaphthalene-6-sulfonic acid, 1,7-dihydroxynaphthalene-3-sulfonic acid, 4,5-dihydroxynaphthalene-2,7-disulfone A hair deformative composition comprising at least one selected from acid sulfonic acids and salts thereof, and (c) an organic solvent, and exhibiting acidity. 2. The organic solvent (c) is represented by the following general formula (c-
1); (In the formula, R ⁵¹ represents a hydrogen atom, a methyl group or a methoxy group, R ⁵² and R ⁵³ represent a hydrogen atom or a hydroxyl group, and p, q and r each represent an integer of 0 to 5, provided that ,
When p = q = r = 0 and R ⁵² = R ⁵³ , p = q =
(R = 0, R ⁵¹ is a hydrogen atom and R ⁵² is not a hydroxyl group), and its content is 5 to 50% by weight in the hair deforming composition. Hair deforming composition. 3. The method according to claim 1, wherein the pH is less than 2 to 7.
A hair deforming composition according to the above.