JPS6228765B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a hair styling product. Hair styling products currently on the market include liquid hair liquids, hair tonics, paste pomades, solid sticks, and emulsified creams. Its components include a base component that has so-called hair-styling properties, a solvent, a fragrance, additives, and the like. Conventionally, various animal and vegetable oils and fats and mineral oils have been used as base components having hair styling properties, but in recent years, synthetic oils such as polyalkylene glycol compounds have been used. Among polyalkylene glycol compounds, polypropylene glycol and its derivatives are widely used. The physical properties required for a hair styling product base material are that it has excellent hair styling ability, that it does not corrode celluloid and synthetic resins used as combs for glasses, and that it can be easily washed off when washing hair.
It is important that there is no irritation to the hair or scalp. However, among these physical properties, base materials with excellent hair styling properties have the disadvantage that they are difficult to remove when hair is washed, and base materials with good hair washing properties have poor hair styling properties, so a base material that satisfies all physical properties is desired. ing. Vegetable oils such as castor oil, camellia oil, and Japanese wax, and mineral oils such as liquid paraffin have good hair styling properties, but are difficult to wash off. Polyalkylene glycol base materials that have been used in recent years can be made by changing the degree of polymerization.
A base material having an arbitrary viscosity can be obtained, and by changing the type of alkylene oxide and the number of moles added, it is possible to obtain a desired base material from water-soluble to water-insoluble. However, no compound has been obtained that satisfies all of the properties of hair styling ability, celluloid erosion properties, and hair washing properties. The present inventors synthesized polyoxyalkylene glycols with different types and molar addition ratios of base alcohol and alkylene oxide,
As a result of intensive research, we have come up with the invention of a hair styling product base material that can simultaneously satisfy the above three properties. The hair styling composition of the present invention has the formula [-O(R'O) _a (C ₃ H ₆ O) _b H] _c () (wherein R is a C ₂ to _{C 4} hydrocarbon residue, R' is butylene oxide, or a group in which butylene oxide and propylene oxide are randomly polymerized, a
and b are numbers from 1 to 3 and 1 to 4, respectively, and are determined so that the weight ratio of butylene oxide and propylene oxide is 80:20 to 40:60 and the molecular weight is less than 500, and c is a number of 2 or 3. It is characterized by containing one or more phosphoric acid esters of polyols represented by (integer). The polyol represented by the above formula () is produced by adding butylene oxide and propylene oxide to a polyol such as ethylene glycol, propylene glycol, butanediol, glycerin, diethylene glycol, or the like. The polyol () of the present invention has a molecular weight of 500
If it exceeds this, the viscosity will increase, which is not preferable. In addition, the lower limit of molecular weight is determined by the selection of hydrocarbon residues, but in practical terms 300
The above is desirable. Also, the weight ratio of butylene oxide and propylene oxide is 80:20-40:
It must be between 60 and 60%. Too much butylene oxide will result in poor hair washing properties, and too much propylene oxide will result in poor hair styling properties and celluloid erosion properties. The reaction between the polyhydric alcohol and alkylene oxide described above may be carried out at 90°C to 150°C under an inert gas atmosphere under increased pressure or normal pressure using an alkali catalyst such as potassium hydroxide or sodium hydroxide. The phosphoric acid esterification of the above compound () may be carried out by reacting a phosphoric acid esterifying agent such as phosphorus pentoxide, polyphosphoric acid, or phosphorus oxychloride by a conventional method. The phosphoric acid esters of the present invention are used alone or as a mixture of two or more in the hair styling product base material. It may also be mixed with other types of hair styling material base materials. Other base materials to be mixed include the compound of the above formula () or the formula RO(R′O) _a (C ₃ H ₆ O) _b H (wherein R is a C ₁ to C ₁₈ alkyl group, R′O is butylene oxide or a group in which butylene oxide and propylene oxide are randomly polymerized, a and b are a group in which the weight ratio of butylene oxide and propylene oxide is 10:90 to 90:10, and the molecular weight is 500 to 500.
polyoxyalkylene monoalkyl ether, or its phosphate tester or the formula R[-O(R'O) _a -(C ₃ H ₆ O) _b H] _c R is a C ₂ to C ₈ hydrocarbon residue, R′O is butylene oxide or a group in which butylene oxide and propylene oxide are randomly polymerized, a
and b has a weight ratio of butylene oxide and propylene oxide of 10:90 to 90:10 and a molecular weight of 800 to
5000, c is an integer from 2 to 8), or phosphoric acid esters. A high-quality hair styling product can be produced by blending water, ethanol, etc. with the hair styling product base material of the present invention. When used, the hair styling product of the present invention satisfies all of hair styling properties, celluloid erosion properties, and hair washing properties. Hereinafter, representative examples of the present invention will be explained in more detail with reference to Production Examples, Examples, and Comparative Examples. Production example 1 3 Glycerin in a stainless steel autoclave
Add 276 g (3.0 mol) and 2.89 g of potassium hydroxide, replace the gas phase with nitrogen gas, and heat to 110°C. 648g (9.0mol) of butylene oxide to 100g
C. to 120.degree. C. under the conditions of 6.5 kg/ ^cm.sup.2 G or less, further 522 g (9.0 mol) of propylene oxide was fed under the same conditions, and after the feeding, stirring was performed under the same conditions for 2 hours. The reaction product was taken out, the catalyst was removed, and low-boiling substances were removed while blowing nitrogen under the conditions of 90°C to 100°C and 1.0 mmHg to obtain 1330 g of a pale yellow transparent viscous liquid. The hydroxyl value of the obtained compound was 40.8 mgKOH/g. 3 Put the above compound (molecular weight
458) 916 g (2.0 mol) was added, and 142 g (1.0 mol) of phosphorus pentoxide was added little by little at 30°C to 40°C under a nitrogen atmosphere over 1 hour. After further stirring at the same temperature for 1 hour, add 36 g (2 moles) of water and mix at 70℃~
Raise the temperature to 80℃ and heat and stir for 1 hour to perform hydrolysis. Next, at the same temperature, the pressure was reduced to 30 mmHg and degassed for 2 hours under nitrogen blowing to obtain 1090 g of a pale yellow viscous liquid. In the evaluation, 1.2 mol of triethanolamine was added per 1 mol of the compound obtained above in the form of a salt. Production Examples 2 to 4 The following phosphorus residual ester compounds were produced according to the method of Production Example 1. 2 C ₂ H ₄ [O(C ₄ H ₈ O) ₂ (C ₃ H ₆ O) ₁ H] Phosphate ester of ₂ 3 C ₂ H ₄ [O(C ₄ H ₈ O/C ₃ H ₆ O) ₂ (C ₃ H ₆ O) ₁ H〕 ₂
Phosphate ester of 4 C ₄ H ₈ [O(C ₄ H ₈ O) ₁ (C ₃ H ₆ O) ₁ H] Phosphate ester of ₂ Examples 1 to 4 Compounds obtained in Production Examples 1 to 4 above The mixture was tested for ceroid erosion properties, hygroscopicity, hair styling properties, and hair washing properties. The results are shown in Table 1. The evaluation method is as follows: (1) Celluloid erosivity Take 70 ml of a test solution containing the compound of the present invention: ethanol: water at a weight ratio of 15:50:35 into a 100 ml sample bottle, and add 20 mm x 50 mm x
After soaking a 0.6 mm celluloid plate at 23±1℃ for 96 hours, the weight change of the celluloid plate was measured.
Observe the appearance. In Table 1, the mark ○ indicates good appearance with almost no change, and the mark x indicates poor appearance (deformation). (2) Hygroscopicity Weigh accurately 7g of the compound of the present invention in a 100ml beaker and place it in a desiccator (23±1°C, 80%RH) containing a saturated ammonium sulfate solution for 96 hours.The increase in weight is taken as the amount of moisture absorbed. (3) Hair styling property Compound of the present invention: Ethanol: Water weight ratio: 15:
A man's hair was treated with a 55:35 sample, dried with a hair dryer, and then conditioned at 23°C and 80% RH for 24 hours to observe changes. ○ marks in Table 1 indicate good hair styling properties.
An x mark indicates poor hair styling properties. (4) Hair washability The sample tested for hair styling properties is immersed in a 5% aqueous solution of sodium salt of polyoxyethylene lauryl sulfate and stirred at 25°C for 5 minutes. Next, it was soaked in water and stirred at 25°C for 5 minutes, then washed with water three times and dried. This sample was immersed in ethanol for extraction and compared with an extract from untreated hair. 1st
In the table, ○ indicates good hair washability, ×
The mark indicates poor hair washability. Comparative Examples 1 to 4 The following compounds were manufactured by a method similar to the manufacturing method of the manufacturing example, and their performance was evaluated by the method described above. The results are shown in Table 1. 1 C ₃ H ₅ [O(C ₃ H ₆ O) ₃ H] Phosphate ester of ₃ 2 C ₂ H ₄ [O(C ₄ H ₈ O) ₁₀ (C ₃ H ₆ O) ₃ H] Phosphorus of ₂ Acid ester 3 C ₃ H ₆ [O(C ₄ H ₈ O) ₂ (C ₂ H ₄ O) ₁ ] Phosphate ester of ₂ C ₃ H ₅ [O(C ₄ H ₈ O) ₂ H] ₃ Regarding phosphoric acid ester 4, the phosphoric acid esterification reaction did not proceed and no product that could be put to practical use could be obtained. 【table】

Claims (1)

[Claims] 1 Formula R[O(R'O)a(C ₃ H ₆ O) bH]c (wherein R is a C ₂ to _{C 4} alkyl group, R'O is butylene oxide or butylene oxide A group in which and propylene oxide are randomly polymerized, a
and b are numbers from 1 to 3 and 1 to 4, respectively, and are determined so that the weight ratio of butylene oxide and propylene oxide is 80:20 to 40:60 and the molecular weight is less than 500, and c is 2 or 3. A hair styling composition comprising one or more phosphoric acid esters of polyols represented by the following integer: