JPS628105B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to hair cosmetics that are more effective in imparting flexibility 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. I end up. 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.
There are ``no-rinse type'' types, and each type has a different usage pattern. 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, as a result of various studies, it was discovered that a specific choline derivative is highly safe, has surface activity, and has high adsorption to hair, leading to the completion of the present invention. . The hair cosmetic composition of the present invention exhibits excellent hair flexibility when applied to both "rinsing type" and "non-rinsing type". The object of the present invention is to provide a hair cosmetic having an excellent effect in imparting flexibility, and the object is to add 0.1 to 5.0% by weight of a quaternary ammonium salt represented by the following general formula (). This is achieved by a hair cosmetic containing %. 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 () is a compound also called acylated choline. The amount of acylated choline to be blended is 0.1 to 5.0% 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 flexibility-imparting effect of the present invention will not be exhibited, and if it exceeds 5.0% by weight, the stickiness and weight of the hair will increase, and the flexibility-imparting effect will also decrease. 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 deteriorates, which is not preferable. When R ¹ exceeds C ₂₃ , 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 extracting the above stearoyldimethylethanolamine 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 hair cosmetic of the present invention may contain other optional ingredients 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 tallow alkyltrimethylammonium chloride, eicosyltrimethylammonium chloride, heneicosyltrimethylammonium chloride; liquid paraffin;
Hydrocarbons such as petrolatum, solid paraffin, squalane and olefin oligomers; esters such as isopropyl myristate, isopropyl palmitate, stearyl stearate, octyldodecyl myristate, octyldodecyl oleate and 2-ethylhexanoic acid triglyceride;
Higher alcohols such as cetanol, stearyl alcohol, cetostearyl alcohol, behenyl alcohol and hexyldecanol; emulsifiers such as glyceryl monostearate, sorbitan monopalmitate, polyoxyethylene cetyl ether, polyoxyethylene stearate and polyoxyethylene sorbitan monolaurate ; Cellulose derivatives such as methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose and cationized cellulose; Thickeners such as natural polymers; ethylene glycol, propylene glycol, 1,3-butylene glycol,
Humectants such as glycerin and sorbitol; and other minor components 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: Apply 0.5g of the sample directly to a shampoo-treated hair bundle (5gr, 20cm), spread it evenly by hand, dry in an atmosphere of 25℃, 65% RH, and leave it overnight for flexibility of the hair bundle. Sensory evaluation was conducted by 20 panelists. Evaluation criteria are 1.0% by weight stearyltrimethylammonium chloride, 3.0
This is a five-point evaluation based on the evaluation obtained with a sample consisting of cetostearyl alcohol (a 1:1 mixture of cetyl alcohol and stearyl alcohol) at % by weight, propylene glycol at 5.0% by weight, and water (the balance). Evaluation criteria ◎: Good 〇: Slightly good △: (Standard) equivalent ×: Slightly inferior XX: Inferior In each test example, all blending amounts are expressed in weight %. Test Example 1 Six types of hair cosmetics having the compositions shown in Table 1 below were prepared and their performance (softness) was tested. The results are shown in the same table.

[Table] As is clear from Table 1, acylated choline, which is an essential component of the present invention, satisfies the flexibility within 0.1 to 5% by weight. Test Example 2 Various acylated cholines were blended into hair cosmetics,
The flexibility imparted by these acylated cholines to hair was tested. The results are shown in Table 2 below.
is shown.

【table】

[Table] As is clear from Table 2, compositions containing acylated choline within the scope of the present invention (Examples 3 to 3)
8) all satisfy hair flexibility, whereas
The compositions of Comparative Examples 5 and 6 containing acylated choline in which R ¹ is outside the range of C _{11 to} C ₂₃ have poor flexibility. Test Example 3 A hair cream composition having the composition shown in Table 3 below was prepared and its performance was evaluated.

【table】

[Table] The above composition of the present invention exhibited unprecedented hair flexibility.

Claims (1)

[Scope of Claims] 1. A hair cosmetic containing 0.1 to 5.0% by weight of a quaternary ammonium salt represented by the following general formula (). 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. )