JPS628107B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to hair cosmetics that are more effective in imparting "combability" to hair than conventional cationic surfactants. Normally, hair is covered with animal and vegetable oils such as hair creams and hair oils, as well as sebum secreted from the hair itself, but when hair is washed with soap or synthetic detergents, these oils and fats are removed more than necessary. Put it away. As a result, the hair after washing loses its smoothness, feels dry and stiff, and becomes difficult to comb, making it more likely to cause split ends and split ends. In order to eliminate such inconveniences, various hair cosmetics have been developed and used as hair treatment agents after hair washing. These hair cosmetics contain quaternary ammonium salts such as dialkyldimethylammonium chloride and alkyltrimethylammonium chloride as the main active ingredient. There are two types of ammonium salts: those that are poorly soluble in water and those that are easily soluble in water.Therefore, hair cosmetics are divided into ``rinsing type'' and ``non-rinsing type''. This makes their usage patterns different. In order to prevent hair from squeaking and tangling after washing, etc., and to improve the finish when dry, the above ammonium salt must be adsorbed to the hair. In addition, with the recent trend towards natural products, there is a growing trend to seek safer products. In light of this situation, we conducted various studies and found that certain choline derivatives are highly safe, have surface activity, and are highly adsorbed to hair.
The present invention has now been completed. The hair cosmetic of the present invention exhibits excellent smoothness when applied to both "rinsing type" and "non-rinsing type". The purpose of the present invention is to provide a hair cosmetic that has an excellent effect on imparting "combability" to hair.
This purpose is to contain 0.1 to 3.0% by weight of a quaternary ammonium salt represented by the following general formula () and 0.1 to 10% by weight of an amino acid, and the weight ratio of the quaternary ammonium salt/amino acid is 1/9 to 9. /1. General formula: (In the formula, R ¹ is an alkyl group having 11 to 23 carbon atoms,
R ² , R ³ and R ⁴ each represent an alkyl group or hydroxyalkyl group having 1 to 3 carbon atoms, and X represents a halogen atom or an alkyl sulfate group having 1 or 2 carbon atoms in the alkyl group, respectively. ) The quaternary ammonium salt represented by the above general formula (), which is the first essential component of the present invention, is a compound also called acylated choline. The amount of the acylated choline blended is 0.1 to 3.0% by weight, preferably 0.1 to 2.0% by weight, based on the total hair cosmetic composition of the present invention. If it is less than 0.1% by weight, the effect of the present invention will not be exhibited, and if it exceeds 3.0% by weight, the stickiness and weight of the hair will increase, which is not preferable. What is particularly important in the present invention is shown in the above general formula.
R ¹ is a C _11-23 alkyl group, and R ¹ is
If C is less than ₁₁ , water solubility increases, adsorption to hair decreases, and safety also deteriorates, which is not preferable.
If R ¹ exceeds C ₂₃ , the oil solubility increases and adsorption to hair decreases, which is not preferable. Particularly preferred R ¹ is a C _15-21 alkyl group. Specific examples of acylated choline preferably used in the present invention are shown below. Choline stearyl ester halide
(R ¹ = C ₁₇ alkyl) Choline palmityl ester halide
(R ¹ = C ₁₅ alkyl) Choline myristyl ester halide
(R ¹ = C ₁₃ alkyl) Choline lauryl ester halide
(R ¹ = C ₁₁ alkyl) Corintaroyl ester halide
(R ¹ = C _15-17 alkyl) Choline stearyl ester sulfate
(R ¹ = C ₁₇ alkyl) Cholineeicosyl ester halide
(R ¹ = C ₁₉ alkyl) Cholindocosanyl ester halide
(R ¹ = C ₂₁ alkyl) Choline tetracosanyl ester halide
(R ¹ = C ₂₃ alkyl) Choline eicosyl ester sulfate
(R ¹ = C ₁₉ alkyl) Cholindocosanyl ester sulfate
(R ¹ =C ₂₁ alkyl) A method for synthesizing choline stearyl ester halide (stearoylcholine chloride), which is an example of acylated choline used in the present invention, is shown below. Laboratory-scale synthesis Stearic acid obtained by hydrolyzing hydrogenated beef tallow is reacted with thionyl chloride to obtain stearic acid chloride (C ₁₇ H ₃₅ COCl). (Reaction formula A) Ethylene oxide is added to dimethylamine to form dimethylethanolamine (HOCH ₂ CH ₂ N
(CH ₃ ) ₂ ) is obtained. (Reaction formula B) The stearic acid chloride is reacted with twice the mole of dimethylethanolamine (DME) in the absence of a solvent and catalyst to obtain stearoyldimethylethanolamine (C ₁₇ H ₃₅ COOCH ₂ CH ₂ N(CH ₃ ) ₂ ). (Reaction formula C) After the stearoyldimethylethanolamine is extracted with ether, it is quaternized using methylene chloride to obtain the desired stearoylcholine chloride (C ₁₇ H ₃₅ COOCH ₂ CH ₂ N(CH ₃ ) ₃ Cl). (Reaction formula D) Industrial-scale synthesis method Stearic acid is dissolved at high temperature (approximately 180°C), DME is added dropwise into the solution, and after the reaction is completed, water is removed under reduced pressure to produce stearoyldimethylethanolamine (C ₁₇ H ₃₅ COOCH ₂ CH _2N ( _CH3 ) ₂ ) is obtained. (Reaction formula E) Stearoyldimethylethanolamine is quaternized with methylene chloride to obtain the desired stearoylcholine chloride. (Reaction formula F) The amino acid, which is the second essential component of the present invention, can be blended in an amount of 0.1 to 10.0% by weight, preferably 0.1 to 5.0% by weight, based on the entire hair cosmetic composition of the present invention. If it is less than 0.1% by weight, the effect of the present invention will not be exhibited.
If it exceeds 10.0% by weight, the hair becomes sticky and heavy, which is undesirable. Representative examples of the amino acids of the present invention include glycine, L-valine, L-isoleucine, L-serine, L-threonine, L-phenylalanine, L-
- tryptophan, L-cysteic acid, L-proline, L-aspartic acid, L-glutamic acid,
They are L-histidine, L-arginine, and L-lysine, and it is possible to use one or more selected from these. Particularly preferably,
Glycine, L-isoleucine, L-proline, L
- Histidine, L-arginine, L-lysine,
L-cysteic acid. What is particularly important about the hair cosmetics of the present invention is that
The weight ratio (()/amino acid) of the quaternary ammonium salt of the above general formula () to the amino acid is 1/9 to 9/
It is necessary to be within the range of 1. A particularly preferred range is 3/7 to 7/3. If the ( )/amino acid ratio is less than 1/9, the effects of the present invention cannot be obtained, and if the ratio exceeds 9/1, the combability deteriorates, which is not preferable. It is possible to incorporate other optional ingredients into the hair cosmetic composition of the present invention within a range that does not affect the effects of the present invention. Such optional ingredients include the following substances: stearyltrimethylammonium chloride,
Mono- or dialkyl-type quaternary ammonium salts such as hydrogenated beef tallow alkyltrimethylammonium chloride, eicosyltrimethylammonium chloride, heneicosyltrimethylammonium chloride; alginate propylene glycol ester, sodium alginate, algecolloid, lecithin, pyroglutamic acid Monostearin, monoolein pyroglutamic acid, higher fatty acids, oxycarboxylic acids, and the following general-purpose ingredients can also be blended. Hydrocarbons such as petrolatum and olefin oligomers; esters such as isopropyl myristate, isopropyl palmitate, stearyl stearate, octyldodecyl myristate, octyldodecyl oleate and 2-ethylhexanoic acid triglyceride; cetanol, stearyl alcohol, cetostearyl alcohol, Higher alcohols such as behenyl alcohol and hexyldecanol; emulsifiers such as glyceryl monostearate, sorbitan monopalmitate, polyoxyethylene cetyl ether, polyoxyethylene stearate and polyoxyethylene sorbitan monolaurate; methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose and cellulose derivatives such as cationized cellulose; thickeners such as natural polymers; humectants such as ethylene glycol, propylene glycol, 1,3-butylene glycol, glycerin and sorbitol; and other solvents, disinfectants, fragrances, etc. It is a minor component. The hair cosmetic composition of the present invention can be used in various hair treatment applications such as a hair rinse, a spray-type or dispenser-type hair conditioner, and a hair lotion. Next, Examples and Comparative Examples of the present invention will be shown to explain the effects of the present invention more specifically. Before explaining each example, the test method adopted in each example will be explained. Test method: Apply 0.5g of the sample directly to a shampooed hair bundle (5gr, 20cm), spread it evenly by hand, dry it in an atmosphere of 25℃, 65% RH, and check the smoothness of the hair bundle after leaving it overnight. Sensory evaluation was conducted by 20 panelists. The evaluation criteria is a five-level evaluation based on the evaluation obtained from a sample consisting of 1.0% by weight of stearyltrimethylammonium chloride, 5.0% by weight of propylene glycol, and water (the balance). Evaluation criteria ◎: Good 〇: Fairly good △: (Standard) equivalent ×: Slightly inferior ××: Poor In addition, in each test example, all compounding amounts are weight%
It is indicated by. Test Example 1 Four types of hair cosmetics having the compositions shown in Table 1 below were prepared and their performance (combability) was tested. The results are shown in the same table.

Table 1 clearly shows the combined effect of the acylated choline and amino acids of the present invention. Test Example 2 Eleven types of hair cosmetics were prepared with varying weight ratios of acylated choline and amino acids, and their performance was tested. The results are shown in Table-2.

[Table] As is clear from Table 2, excellent combability can be imparted to hair when the weight ratio of acylated choline to amino acid is within the range of 1/9 to 9/1. Test Example 3 Various acylated cholines were blended into hair cosmetics,
The combability of these hairs was tested. The results are shown in Table 3 below.

【table】

[Table] As is clear from Table 3, the compositions of Comparative Examples 7 and 8 containing acylated choline in which R ¹ is outside the range of C _{11 to 23} cannot satisfy smoothness. Test Example 4 Ten types of hair cosmetics of the present invention having different types of amino acids were prepared as shown in Table 4, and their performance was tested. As is clear from Table 4, Examples 16 to 25
All of the compositions exhibited good combability.

【table】

[Table] Test Example 5 Two types of hair rinse compositions having the formulation shown in Table 5 below were prepared and their performance was evaluated. Performance rating is 40
The experiment was carried out by directly applying 0.5 g of the hair rinse composition at °C to a shampoo-treated hair bundle (5 g, 20 cm), spreading it evenly by hand, rinsing it, and then drying it.

【table】

Table 5 clearly shows the combined effect of acylated choline and amino acids.

Claims (1)

[Claims] 1 Contains 0.1 to 3.0% by weight of a quaternary ammonium salt represented by the following general formula () and 0.1 to 10% by weight of an amino acid, and the weight ratio of the quaternary ammonium salt/amino acid is 1 A hair cosmetic characterized by being 9/9 to 9/1. General formula: (In the formula, R ¹ is an alkyl group having 11 to 23 carbon atoms,
R ² , R ³ and R ⁴ each represent an alkyl group or hydroxyalkyl group having 1 to 3 carbon atoms, and X represents a halogen atom or an alkyl sulfate group having 1 or 2 carbon atoms in the alkyl group, respectively. ) 2 Amino acids are glycine, L-valine, L-isoleucine, L-serine, L-threonine, L-
A patent for one or more selected from phenylalanine, L-tryptophan, L-proline, L-aspartic acid, L-glutamic acid, L-histidine, L-arginine, L-lysine, and L-cysteic acid. A hair cosmetic according to claim 1.