JPS628106B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to hair cosmetics that are more effective in imparting "smoothness" 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. . 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 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. Also, with the recent trend towards natural products, there is a growing trend towards products with a higher degree of safety. In light of this situation, we conducted various studies and found that certain choline derivatives are highly safe, have surface activity, and are highly adsorbent to hair.
The present invention has now been completed. The hair cosmetics of the present invention are available in "rinsing type" and "non-rinsing type".
It exhibits excellent smoothness no matter which type it is applied to. The purpose of the present invention is to provide a hair cosmetic that has an excellent effect on imparting "smoothness" to hair, and this purpose aims to provide a hair cosmetic that has an excellent effect on imparting "smoothness" to hair, and this purpose aims to provide a hair cosmetic that has 0.1 to 3.0% by weight of a quaternary ammonium salt represented by the following general formula () and Contains 0.1 to 10% by weight of animal or vegetable oil, and the weight ratio of the quaternary ammonium salt/animal or vegetable oil is 1/
This is achieved by a hair cosmetic composition characterized by a hair ratio of 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 above general formula (1) which is the first essential component of the present invention
The quaternary ammonium salt represented by is a compound also called acylated choline. The amount of the above-mentioned acylated choline is 0.1 to 3.0% by weight based on the entire hair cosmetic of the present invention.
Preferably it is 0.1 to 2.0% by weight. 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 that R ¹ shown in the above general formula is a C _11-23 alkyl group, and R ¹
If it is less than C 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 above 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 and stearoyldimethylethanolamine (C ₁₇ H ₃₅ COOCH ₂ CH ₂ N(CH ₃ ) ₂ ) is obtained.
(Reaction formula E) Stearoyldimethylethanolamine is quaternized with methylene chloride to obtain the desired stearoylcholine chloride. (Reaction formula F) The animal and vegetable oils that are the second essential component of the present invention include liquid paraffin, pristane, squalane, mink oil, lanolin, olive oil, grapeseed oil, wheat germ oil, camellia oil, jojoba oil,
sunflower oil, sasanqua oil, corn oil,
One or more selected from linseed oil, avocado oil, cholestearyl oleate, and cholestearyl isostearate, and particularly preferred are squalane camellia oil, jojoba oil, sasanquan oil, linseed oil, and avocado oil. The amount of the second essential component to be blended is 0.1 to 10.0% by weight, preferably 0.1 to 5.0% by weight, based on the total hair cosmetic composition of the present invention. If the amount is less than 0.1% by weight, the effect of the present invention will not be exhibited, and if it exceeds 10.0% by weight, the stickiness and weight of the hair will increase, which is not preferable. What is particularly important in the hair cosmetic of the present invention is the weight ratio of the quaternary ammonium salt of the above-mentioned general formula () to animal and vegetable oils (()/animal and vegetable oils)
must be in the range of 1/9 to 9/1. A particularly preferred range is 3/7 to 7/3. ()/Animal and vegetable oils and fats of less than 1/9 are undesirable because adsorption to hair deteriorates and smoothness is not achieved. Furthermore, if the above ratio exceeds 9/1, the hair will become sticky and the hair will not be smooth. 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: Mono- or dialkyl-type quaternary ammonium salts such as stearyltrimethylammonium chloride, hydrogenated tallow alkyltrimethylammonium chloride, eicosyltrimethylammonium chloride, heneicosyltrimethylammonium chloride; alginate propylene glycol ester, sodium alginate, algae Colloids, lecithin, monostearin pyroglutamate, monoolein pyroglutamate, 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; ethylene glycol, propylene glycol, 1,3-
Humectants such as butylene glycol, glycerin, and sorbitol; and other small amounts of ingredients such as solvents, disinfectants, and fragrances. 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: Directly apply 0.5g of the sample to a shampooed hair bundle (5gr, 20cm), spread it evenly with the hair, dry in an atmosphere of 25℃, 65% RH, and leave it overnight to smooth the hair bundle. Sensory evaluation will be conducted by 20 panelists. Evaluation criteria: 1.0% by weight stearyltrimethylammonium chloride
This is a 5-level evaluation based on the evaluation obtained from a sample consisting of 5.0% by weight of propylene glycol and water (the balance). ◎: Good 〇: Slightly good △: (Standard) equivalent ×: Slightly inferior XX: Inferior In addition, in each test example, all blending amounts are expressed in weight %. Test Example 1 Eight types of hair cosmetics having the compositions shown in Table 1 below were prepared and their performance (smoothness) was tested. The results are shown in the same table.

[Table] Table 1 clearly shows the combination effect of the acylated choline of the present invention and animal and vegetable oils and fats. Test Example 2 Five types of hair cosmetics with varying weight ratios of acylated choline and animal and vegetable oils and fats were prepared and tested for performance. The results are shown in Table-2.

[Table] As is clear from Table 2, excellent smoothness can be imparted to hair when the weight ratio of acylated choline to oil is within the range of 1/9 to 9/1. Test Example 3 Eight types of hair cosmetics with different types of acylated choline were prepared and their performance was tested. The results are shown in Table 3 below.

[Table] As is clear from Table 3, Comparative Example 6 contains acylated choline in which R ¹ is outside the range of C ₁₁ to C ₂₃
Compositions No. 7 and 7 do not satisfy smoothness. Test Example 4 A hair rinse composition having the composition shown in Table 4 below was prepared and its performance was evaluated. Performance evaluation is 40℃
0.5 g of the hair rinse composition was applied directly to a shampoo-treated hair bundle (5 g, 20 cm), spread evenly by hand, rinsed, and dried.

[Table] The hair rinse composition of the present invention was able to impart unprecedented smoothness to hair. Test Example 5 Hair cream compositions having the formulation shown in Table 5 below were prepared and evaluated for smoothness.

【table】

[Table] The hair cream composition of the present invention had unprecedented smoothness.

Claims (1)

[Claims] 1. 0.1 to 3.0% by weight of a quaternary ammonium salt represented by the following general formula () and 0.1% by weight of animal or vegetable oil or fat.
A hair cosmetic containing 1 to 10% by weight of the quaternary ammonium salt and having a weight ratio of 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. )