JPH0454113A - Hair cosmetic - Google Patents

Abstract

PURPOSE:To obtain a hair cosmetic providing the hair with excellent flexibility, feeling of moisture and excellent smoothness, containing a guanidine derivative and a 1-hydroxy-2-pyridone salt. CONSTITUTION:A hair cosmetic base is blended with 0.05-10wt.% based on the whole amount of a guanidine derivative shown by the formula I (R<1> is 1-22C alkyl or alkenyl; A is 1-10C alkylene or alkenylene; m is 0 or 1; n is 1-5) containing an amide group in the molecule) or salt thereof and 0.05-3wt.% 1-hydroxy-2pyridone salt shown by formula II (R<2> is 1-11C alkyl, alkenyl, 5-8C cycloalkyl, cycloalkenyl or heterocyclic derivative group; X is organic group or inorganic cation). The blend is properly mixed with conventional components such as liquid paraffin, surfactant, humectant, perfume, etc., to give the objective substance. The objective substance is applicable to hair rinse, hair conditioner, hair lotion, hair treatment, etc.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a hair cosmetic that not only imparts softness and moistness to the hair, but also has an excellent effect in imparting smoothness to the hair. .

[Problems to be solved by conventional techniques and inventions] Usually,
Hair is covered with sebum and other substances secreted from the hair itself, but washing with soap, synthetic detergent, etc. or perm treatment removes more of these oil and fat components than necessary. As a result, the hair after washing loses its smoothness and feels dry and stiff, making it difficult to comb through the hair, making it more likely to cause split ends and split ends.

In order to eliminate these inconveniences, various hair cosmetics have been developed as hair treatment agents, representative examples include di-long-chain di-short-chain alkyl ammonium salts such as dialkyldimethylammonium chloride, and alkyltrimethylammonium chloride. Hair cosmetics containing quaternary ammonium salts such as mono-long-chain alkyl tri-short-chain alkyl ammonium salts as a main active ingredient are known.

However, these quaternary ammonium salts are not only irritating to the hair and scalp, but also have a sterile effect due to the fact that the charged nitrogen atom, which is the center of adsorption, is covered with long-chain and short-chain alkyl groups and alkenyl groups. Due to this disorder, the adsorption power to the hair is weak, and it is easy to detach from the hair when rinsing or the like.

For this reason, hair cosmetics containing quaternary ammonium salts as active ingredients have difficulty adsorbing the active ingredients to the hair, so there is still room for improvement in terms of imparting softness and smoothness to hair after washing. Previously, oil was used in combination with this, but if used in an amount that would give smoothness, it lacked a moist feeling and became dry, but on the other hand, if the amount used was increased, an improvement in the moist feeling could be seen. However, there was a problem in that it became sticky and lacked softness.

The present invention was made in view of the above circumstances, and an object of the present invention is to provide a hair cosmetic that is moist, soft, and smooth.

[Means and effects for solving the problem] The present inventors,
As a result of intensive studies to achieve the above objective, we found the following general formula (1) (wherein R1 is a branched or straight-chain alkyl group or alkenyl group having 1 to 22 carbon atoms, and A is a carbon Number 1~
10 branched or linear alkylene groups or alkenylene groups, and m is O or 1. Further, n is an integer of I to 5. ) and one or more selected from guanidine derivatives having an amide group in the molecule and their salts, and the following general formula (2) (wherein R2 is an alkyl group having 1 to 11 carbon atoms or one type of 1-hydroxy-2-pyridone salt represented by an alkenyl group, a cycloalkyl group or cycloalkenyl group having 5 to 8 carbon atoms, or a heterocyclic derivative group, where X represents an organic base or an inorganic cation; It has been found that by using two or more types in combination, a hair cosmetic can be obtained that can impart flexibility and a moist feel to the hair, as well as impart smoothness to the hair.

That is, the mono-N-substituted guanidine derivative has a guanidine group, which is a strongly basic group, in its molecule, and this group has a strong guanidine group that can form a strong twinning ion with a resonant monovalent anion species such as a carboxy anion. Because it has a strong electrostatic effect and hydrogen bonding ability, it has an extremely good affinity for protein fibers such as keratin that have resonant monovalent anion species in their terminal side chains.
Moreover, since it forms a twin ion with the above anion species, its adsorption power is strong. The compound has a very strong affinity with protein fibers such as keratin, and can be adsorbed well to the hair, giving it excellent flexibility, and the introduction of an amide group improves the ability of water molecules to stick to the hair. It also has an excellent moisturizing effect on hair, and due to its molecular structure, it has a high ability to adsorb to hair that has become hydrophilic due to perms, etc., so it is not only good for normal hair after washing but also for hair that has become hydrophilic due to perms. It also adsorbs well to damaged hair, imparting flexibility and moisturizing properties, and satisfactorily solves the inconveniences associated with excessive removal of sebum after washing or perming hair. Therefore, it is highly effective as an active ingredient in hair cosmetics, and in view of this, the applicant has developed hair that has a high adsorption of active ingredients to the hair and provides excellent flexibility and moisturizing properties to the hair. As a cosmetic, a hair cosmetic containing the compound of general formula (1) as an active ingredient was proposed (Japanese Patent Application No. 320075/1983).

As a result of further investigation into this proposal, the present inventors found that the compound of general formula (1) has 1-
By using hydroxy-2-pyridone salt in combination, 1
- It is possible to obtain a hair cosmetic that can more effectively express the effects of hydroxy-2-pyridone salt, can impart smoothness to hair, and has flexibility, moist feeling, and smoothness as described above. This discovery led to the present invention.

The present invention will be explained in more detail below.

The hair cosmetic of the present invention contains, as an active ingredient, a guanidine derivative having an amide group in the molecule represented by the following general formula (1) or a salt thereof as a first essential ingredient.

Here, the substituent R1 in formula (1) has 1 to 22 carbon atoms,
Preferably it is a 11-19 branched or straight-chain alkyl group or alkenyl group, for example C++t(z+-+
C+2Hzs-+ CI:lH2? -I Cl4829
-ICl5H:ll-ICl6)1:+3-, Cl
Jzs-+(CeH+t)zC)I-+ 4-CzHs
C+sHx.

Groups such as are suitable.

Further, substituent A has 1 to 10 carbon atoms, preferably 2 to 6 carbon atoms.
A branched or linear alkylene group or alkenylene group, such as a methylene group, ethylene group, propylene group, butylene group, pentylene group, hexylene group, isopropylene group, 2-pentenyl group, 2-ethylbutylene group, etc. m is 1 or 0.

Note that n is an integer of 1 to 5.

Furthermore, the guanidine derivative of formula (1) is usually formulated in the form of a salt, specifically inorganic acid salts such as hydrochloride, organic acids such as glycolate, acetate, citrate, and acidic amino acid salts. It can be used as a salt, but from the viewpoint of solubility in water, hydrochloride is preferable when using an inorganic acid salt, and glycolate is preferable when using an organic acid salt.

In this case, the guanidine derivative of formula (1) and its salt are:
One type may be blended alone, or two or more types may be used in combination.
In addition, the blending amount is not particularly limited, but the total amount is 0.0
It is preferably 5 to 10% (by weight, hereinafter the same), particularly 0.7 to 5%. If the amount is less than 0.05%, the softening effect may not be sufficient, and if it exceeds 10%, it is not only economically disadvantageous, but also may result in a sticky and heavy finish.

On the other hand, the second essential component of the present invention is a 1-hydroxy-2-pyridone salt represented by the following general formula (2).

(However, in the formula, R1 represents an alkyl group or alkenyl group having 1 to 11 carbon atoms, a cycloalkyl group or cycloalkenyl group having 5 to 8 carbon atoms, or a heterocyclic derivative group, and X represents an organic base or an inorganic cation. .

Here, the alkyl group and the like may be linear or branched, and may be unsubstituted or may have a hydrogen atom substituted with a halogen atom or the like.

Pyridone constituting the above 1-hydroxy-2-pyridone salt includes the following compounds.

1-hydroxy-2-pyridone, 1-hydroxy-4-
Methyl-2-pyridone, 1-hydroxy6-methyl-2
-Pyridone, 1-hydroxy-4,6-dimethyl-2-pyridone, 1-hydroxy-4-methyl-6-hebutyl-
2-pyridone, 1-hydroxy-4-methyl-6-(1
-ethylpentyl)-2-pyridone, 1-hydroxy-
4methyl-6-(2,4,4-)limethylpentyl)-
2-pyridone, 1-hydroxy-4-methyl-6-undecyl-2-pyridone, 1-hydroxy-4-methyl-6-bropenyl-2-pyridone, 1-hydroxy-4-methyl-6-octenyl-2-pyridone, 1-hydroxy- 4-
Methyl-6-(2,2-dibutyl-vinyl)-2-pyridone, 1-hydroxy-4-methyl-6-(cyclohexenylidene-methyl)-2-pyridone, l-hydroxy-4-methyl-6 -cyclohexyl-2-pyridone, 1
-Hydroxy-4-methyl-6-(methyl-cyclohexyl)-2-pyridone, 1-hydroxy-4-methyl-
6-(2-(dimethylcyclohexyl)-propyl)-
2-Pyridone, 1hydroxy-4-methyl-6-(4-
Methyl-phenyl)-2-pyridone, 1-hydroxy-
4-methyl-6-(3-methyl-phenyl)-2-pyridone, 1-hydroxy-4-methyl-6-(4-tert-butyl-phenyl)-2-pyridone, 1-hydroxy-4-methyl-6- (3-methyl-4-10roofenyl)-2
-pyridone, 1-hydroxy-4-methyl-6-(3,
5-dichloro-phenyl)-2-pyridone, l-hydroxy-4-methyl-6-(3-7'rom-4-chloro-
phenyl)-2-pyridone, 1-hydroxy-4-methyl-6-(4-methoxystyryl)-2-pyridone, 1
-Hydroxy-4-methyl-6-[1(4-nitrophenoxy)-butyl]-2-pyridone, 1-hydroxy-
4-Methyl-6-(4cyanophenoxymethyl)-2-
Pyridone, 1-hydroxy-4-methyl-6-(phenylsulfonylmethyl)-2-pyridone, 1-hydroxy-
4-Methyl-6-[1-(4-chlorophenylsulfonyl)-butyl]-2-pyridone, 1-hydroxy-4-
Methyl-6-hensyl-2-pyridone, 1-hydroxy-4-methyl-6-(2,4-dimethylbenzyl)-2
-pyridone, 1-hydroxy-4-methyl-6-(secondary
butyl-benzyl)2-pyridone, 1-hydroxy-4
-Methyl 6-(2-chlorobenzyl)-2-pyridone, 1-hydroxy-4-methyl-6-(4-chlorobenzyl)-2-pyridone, 1-hydroxy-4methyl-6
-(2,5-dichloro-benzyl)-2-pyridone, 1
-Hydroxy-4-methyl-6(4-7” lomo-benzyl)-2-pyridone, 1hydroxy-4-methyl-6-
(phenoxymethyl)-2-pyridone, 1-hydroxy-4-methyl-6-(3-methylphenoxy-methyl)
-2-pyridone, 1-hydroxy-4-methyl-6-(
4-Sec-butylphenoxy-methyl)-2pyridone, 1
-hydroxy-4-methyl-6(2,4,5-trichlorophenoxy-methyl)-2pyridone, 1-hydroxy-4-methyl-6-(4-bromphenoxy-methyl)
-2-pyridone, l-hydroxy-4-methyl-6-(
4-Chlorphenylmercapto-methyl)-2-pyridone, 1-hydroxy-4-methyl-6-(4-methylphenylmercapto-methyl)-2-pyridone, 1-hydroxy-4-methyl-6-(2- naphthyl)-2-pyridone, 1-hydroxy-4-methyl-6-penzhydryl-2-pyridone, 1-hydroxy-4-methyl-6-furyl-2-pyridone, 1-hydroxy-4-methyl-6-
styryl-2-pyridone, etc.

The above compounds are used as organic base salts or inorganic salts, and examples of organic bases include ethanol, amines,
jetanolamine, N-ethylethanolamine, N
-Methyl-getanolamine, triethanolamine, diethylamino-ethanol, 2-amino-2-methyl-n-propanol, dimethylamitubrobanol,
2-amino-2-methyl-propanediol, triisopropanediol, ethylenediamine, hexamenediamine, morpholine, piperidine, cyclohexylamine, tributylamine, dodecylamine, N,N
-dimethyl-dodecylamine, stearylamine, oleylamine, benzylamine, dibenzylamine, N-
Ethylhensylamine, dimethylstearylamine, N
-Methyl-morpholine, N-methylbiperazine, 4-methylcyclohexylamine, N-hydroxyethyl-morpholine, and the like.

Examples of inorganic salts include alkali metal salts such as sodium salts and potassium salts, alkaline earth metal salts such as magnesium salts and calcium salts, and ammonium salts. It can be used in the form of a cation or a tetravalent cation.

The blending amount of 1-hydroxy-2-pyridone salt is 0.05
-3% is preferred, particularly preferably in the range of 0.1-2%. If it is less than 0.05%, the ends of the hair may become dry, and if it exceeds 3%, it may become sticky.

In addition to the above-mentioned essential ingredients, the hair cosmetic composition of the present invention may contain the following optional ingredients as long as they do not affect the effects of the present invention. That is, optional components include hydrocarbons such as liquid paraffin, vaseline, solid paraffin, squalane and olefin oligomers; isopropyl myristate, isopropyl palmitate, stearyl stearate, octyldodecyl myristate, octyldodecyl oleate, and 2-ethyl Esters such as hexanoic acid triglyceride; Emulsifiers such as polyoxyethylene cetyl ether, polyoxyethylene stearate, and polyoxyethylene sorbitan monolaurate; benzalkonium chloride, cetyltrimethylammonium chloride, cetostearyltrimethylammonium chloride, stearyltrimethyl chloride Ammonium, behenyltrimethylammonium chloride, distearyldimethylammonium chloride, N-
Cationic surfactants such as cocoyl arginine ethyl ester salt; N-(2-hydroxyethyl)-N-[bis(
Ampholytic surfactants such as 2-carboxyethyl)aminoethylcholaurylamide disodium salt, 2-cocoyl-N-carboxymethyl-N-hydroxyethylimidazolium betaine; higher alcohol sulfates, alcohol ether sulfates, α-olefin sulfonates, etc. Anionic surfactants such as higher alcohols such as nilauryl alcohol, heptyl alcohol, stearyl alcohol, and hehenyl alcohol; higher fatty acids such as valmitic acid, stearic acid, and behenic acid; ethylene glycol, propylene glycol, 1,3-butylene glycol, Humectants such as glycerin and sorbitol; and other small amounts of ingredients such as solvents, preservatives, and fragrances.

The hair cosmetic composition of the present invention can be used in various applications such as hair rinse agents, spray-type or dispenser-type hair conditioners, hair lotions, and hair treatments.

〔Effect of the invention〕

The hair cosmetic of the present invention provides excellent flexibility and moisturizing feeling to the hair, as well as excellent smoothness, by using the above-mentioned No. 1.2 essential ingredient in combination.

[Examples] The present invention will be specifically described below with reference to Examples and Comparative Examples, but the present invention is not limited to the Examples below.

In addition, in the following examples, all percentages are percentages by weight.

Furthermore, prior to explaining each side, the evaluation method used on each side will be explained.

Sample 0 on shampoo-treated hair bundle (5g, 20cm)
．． Apply 5g directly, spread evenly by hand, and heat at 25°C.
The hair was dried in an atmosphere of 165% RH, and after being left for day and night, a panel of 20 people evaluated the softness, moistness, and smoothness of the hair bundle.

In this case, a sample consisting of 1.0% by weight stearyltrimethylammonium chloride, 3% by weight cetyl alcohol, 10% by weight propylene glycol, and water (the balance) was used as a standard sample, and the following was compared with this standard sample. The above performance was evaluated on a seven-point scale.

7: Very good 6: Good 5: Slightly good 4: Equal 3: Slightly inferior 2: Inferior 1: Very inferior <Examples 1 to 6, Comparative Examples 1 to 4> Hair rinse agent composition shown in Table 1 below were prepared and their performance was evaluated.

In addition, in Table 1, *1 guanidine derivative salt 1,
*2 Guanidine derivative salt 2, *3 1-hydroxy-2
-Pyridone salt 1, *4 Hydroxy-2 Pyridone salt 2 has the following structural formula.

*2H As is clear from Table 1, the hair cosmetic of the comparative example that does not contain the first and second essential ingredients of the present invention has poor hair flexibility, moisturizing, and smoothness. It is recognized that when both essential components are used together, a hair cosmetic that satisfies all of these properties can be obtained.

<Example 7> Hair treatment compositions shown in Table 2 below were prepared and their performance was evaluated.

In Table 2, guanidine derivative salt 1''51-hydroxy-2-pyridone salt 2''6 has the following structural formula.

<Example 8> Hair lotion shown in Table 3 below and evaluated its performance.

In addition, in Table-3 *7 2 *81-hydroxy It has the following structural formula.

Preparation of guanidine derivative salt 2-pyridone salt 3 composition (Example 9) Hair brushing compositions shown in Table 4 below were prepared and their performance was evaluated.

In addition, in Table-4 *9 Guanidine derivative salt 3 *
101-hydroxy-2-pyridone salt 4 has the following structural formula.

*10 <Example 10> Hair rinse compositions shown in Table 5 below were prepared and their performance was evaluated.

In addition, in Table 5 *11 Guanidine derivative salt 3
*12 1-Hydroxy-2-pyridone hydrochloride 1 has the following structural formula.

*11 *12 <Example 11> A hair treatment composition shown in Table 6 below was prepared,
Its performance was evaluated.

In addition, in Table 6 *13 Guanidine derivative salt 4
*14 1-Hydroxy-2-pyridonate 5 has the following structural formula.

*I4 <Example 12> A hair treatment composition shown in Table 7 below was prepared,
Its performance was evaluated.

In addition, in Table 7 *15 Guanidine derivative salt l
*16 Guanidine derivative salt 5 *17 1-Hydroxy-2-pyridonate 6 has the following structural formula.

*16 H *17

Claims (1)

[Claims] 1. The following general formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(1) (However, in the formula, R^1 is a branched or straight chain having 1 to 22 carbon atoms. is an alkyl group or alkenyl group, and A has 1 carbon number.
~10 branched or linear alkylene groups or alkenylene groups, and m is 0 or 1. Also, n is 1 to 5
is an integer. ) and one or more selected from guanidine derivatives having an amide group in the molecule and their salts, and the following general formula (2) ▲Mathematical formulas, chemical formulas, tables, etc.▼...(2) (In the formula, R^2 represents an alkyl group or alkenyl group having 1 to 11 carbon atoms, a cycloalkyl group or cycloalkenyl group having 5 to 8 carbon atoms, or a heterocyclic derivative group, and X represents an organic base or an inorganic cation. 1. A hair cosmetic comprising one or more 1-hydroxy-2-pyridone salts represented by the following formulas: