JPS6228764B2 - - 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 fats and oils and mineral oils have been used as base components containing hair styling products, 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 as a base material for hair styling products are that it has excellent hair styling ability, does not corrode celluloid and synthetic resins used as combs for glasses, and 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 have a desired viscosity by changing the degree of polymerization.
Further, by changing the type of alkylene oxide and the number of moles added, it is possible to obtain a desired water-soluble or water-insoluble product. However, hair styling ability,
No compound has been obtained that satisfies both celluloid erosion properties and hair washing properties. The present inventors synthesized polyoxyalkylene glycols with different types of base alcohol and alkylene oxide and the ratio of added moles, and conducted intensive research, and found that they simultaneously satisfied the above three properties. This led to the invention of a hair styling product base material that can be used as a hair styling product. The hair styling product of the present invention has the formula RO(R'O) _a (C ₃ H ₆ O) _b H (wherein R is a C ₈ to _{C 18} alkyl group, and R'O is butylene oxide or butylene oxide and propylene oxide). A group in which a is randomly polymerized, a
and b are numbers from 1 to 124 and from 1 to 154, respectively, and are determined such that the weight ratio of butylene oxide and propylene oxide is 10:90 to 90:10 and the molecular weight is 500 to 10,000) It is characterized by containing one or more types of phosphoric esters of alkylene monoalkyl ethers. The polyoxyalkylene oxide monoalkyl ether represented by the above formula () includes octanol, lauryl alcohol, cetyl alcohol, 2
-ethylhexanol, stearyl alcohol,
Butylene oxide is added to a C ₈ to _{C 18} alcohol such as isostearyl alcohol, and then propylene oxide is added, or butylene oxide and propylene oxide are randomly added to the C ₈ to C ₁₈ alcohol, and then propylene is added. Synthesized by adding oxide. The polymerization ratio of butylene oxide and propylene oxide is 10:90 to 90:10, preferably 30:70 to 70:30. The reaction between the above-mentioned monohydric alcohol and alkylene oxide may be carried out at 90 to 150° C. under an inert gas atmosphere at normal or increased pressure using an alkali catalyst such as potassium hydroxide or sodium hydroxide. Phosphoric acid esterification of the compound of the above formula () may be carried out by reacting a phosphoric acid esterifying agent such as phosphorus pentoxide, polyphosphoric acid, or phosphorus oxychloride by a conventional method. Conventionally, several types of polyoxyalkylene monoalkyl ether phosphate esters have been used as hair styling products, with different types of alkylene oxides constituting the polyether.
Each type has its advantages and disadvantages, and it has not yet been possible to obtain a truly excellent hair styling product. For example, phosphoric acid esters having ethylene oxide at the polyether end have poor hydrolytic stability and poor hygroscopicity. In the case of a single adduct of butylene oxide or a polyether having butylene oxide at the end, 70 to 80% of the resulting phosphoric acid esterification reaction ends up unreacted. Similarly, phosphoric acid esters of polyethers to which ethylene oxide and propylene oxide are added in blocks cannot provide satisfactory effects on hair styling and hygroscopicity. However, the phosphoric acid ester of the polyether of the present invention which has a butylene oxide group in the chain and a propylene oxide group at the end, when the weight proportion of butylene oxide in the total alkylene oxide is lower than 10%, Hair styling properties and celluloid erosion properties are poor (propylene oxide single adduct is the worst), and when it is higher than 90%, hair washing properties are poor (butylene oxide single adduct is the worst), but when it is between 10 and 90%. teeth,
It is stable and has the most desirable properties as a base material for hair styling products. Further, in order to obtain satisfactory physical properties, the molecular weight of the polyether needs to be between 500 and 10,000. If the molecular weight is less than 500, the viscosity is too low and it is unsuitable for use as a hair conditioner;
If it is greater than 10,000, the viscosity is too high and it is unsuitable for use as a hair conditioner. The polyoxyalkylene monoalkyl ether phosphate 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 as a base material for other types of hair styling products. Other base materials to be mixed include the compound of the above formula () or the formula R[-O(R'O) _a -(C ₃ H ₆ O) _b H] _c (wherein R is C ₂ to C ₈ R'O is a saturated hydrocarbon residue of 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. molecular weight
A number determined to be 800 to 5000, c is 2 to
Examples include polyalkylene oxide polyols represented by (an integer of 8) or phosphoric acid esters of the above polyols. By blending water, ethanol, etc. with the hair styling product base material of the present invention, a high quality hair styling product can be produced. The hair styling product of the present invention satisfies all of hair styling properties, celluloid erosion properties, and hair washing properties when used. Hereinafter, representative examples of the present invention will be explained in more detail with reference to production examples and examples. Production example 1 (phosphoric acid ester of comparative example 1) 3 Put 148 g (2.0 mol) of n-butanol and 4.8 g of potassium hydroxide into a stainless steel autoclave, replace the gas phase with nitrogen gas, and heat to 110°C. . Butylene oxide 1440g ((20.0mol)
was fed under the conditions of 100 to 120° C. and 6.5 kg/cm ² G or less, and further 812 g (14.0 mol) of propylene oxide was fed under the same conditions, followed by heating and stirring for 2 hours under the same conditions. The reaction product was taken out, the catalyst was removed, and low-boiling substances were removed while blowing nitrogen under conditions of 90-100°C and 10 mmHg to obtain 2280 g of a pale yellow transparent viscous liquid. The hydroxyl value of the obtained compound was 48.6 mgKOH/g. 3 Put 2300 g (1.0 mol) of polyoxypropylene polyoxybutylene glycol monobutyl ether (molecular weight 2300) into a flask, and add 71.0 g (0.5 mol) of phosphorus pentoxide in small portions over 1 hour at 30 to 40°C under a nitrogen atmosphere. . After stirring for another hour at the same temperature, add 18 g (1 mol) of water and add 70 to 80 g.
Raise the temperature to ℃ and heat and stir for 60 minutes to perform hydrolysis. Next, at the same temperature, the pressure was reduced to 30 mmHg or less under nitrogen blowing, and deaeration was performed for 2 hours to form a pale yellow viscous liquid.
Obtained 2370g. 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 10 The following phosphoric ester compounds were produced according to the method of Production Example 1 (Production Examples 2 to 5 and 7 to
Ten). A mixture was also produced by blending (Production Example 6) 1 C ₄ H ₉ O (C ₄ H ₈ O) ₁₀ (C ₃ H ₆ O) ₇ H phosphate ester 2 C ₄ H ₉ O (C ₄ H ₈ O) ₈₅ (C ₃ H ₆ O) ₄₀ H〃 3 C ₈ H ₁₇ O (C ₄ H ₈ O) ₂₀ (C ₃ H ₆ O) ₅₀ H〃 4 C ₁₂ H ₂₅ O (C ₄ H ₈ O) ₂₀ (C ₃ H ₆ O) ₁₀ H〃 5 C ₁₈ H ₃₇ O {(C ₄ H ₈ O) ₁₀ (C ₃ H ₆ O) ₃₀ }
Phosphate ester of (C ₃ H ₆ O) ₂₀ H 6 Weight ratio of compounds in Production Example 1 and Production Example 2 1:
Phosphate ester of mixture of 1 7 C ₄ H ₉ O (C ₃ H ₆ O) ₇₀ H〃 8 C ₁₂ H ₂₅ O (C ₄ H ₈ O) ₂₀ (C ₂ H ₄ ) ₁₀ H〃 9 C ₄ H ₉ O (C ₂ H ₄ O) ₄₀ (C ₃ H ₆ O) ₂₀ H〃 10 C ₈ H ₁₇ O (C ₄ H ₈ O) ₂₀ H First of all, we could not obtain anything that could be put to practical use. Examples 1 to 3, Comparative Examples 1 to 7 The compounds and mixtures obtained in Production Examples 1 to 10 above were tested for celluloid erosion properties, hygroscopicity, hair styling properties, hair washing properties, and combability. However, production example 3,
The phosphoric acid esters obtained in Examples 4 and 5 were those of Example 1,
2 and 3, the phosphoric acid esters obtained in Production Examples 1, 2, and 6 to 10 were used in Comparative Examples 1, 2, and 3 to 3, respectively.
It is 7. 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 a 0.6 mm celluloid plate is immersed at 23±1°C for 96 hours, the change in weight of the celluloid plate is measured and the appearance is observed. In Table 1, the mark ○ indicates that the appearance is good and there is almost no change, and the mark x indicates that there is a defect (deformation, etc.). (2) Hygroscopicity Weigh accurately 7g of the compound of the present invention in a 100ml beaker, and place it in a desiccator containing a saturated ammonium sulfate solution (23±1°C, 80%RH) for 96 hours.The increase in weight is defined 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. In Table 1, the ○ mark indicates that the hair styling property is good, and the x mark indicates that the hair styling property is poor. (4) The sample tested for hair washing and 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, and × indicates poor hair washability. (5) Combability Take 2g of the test compound and use a real boxwood comb to
A sensory test was conducted by 10 examiners. The ○ mark in Table 1 indicates good combability, and the × mark indicates good combability.
A mark indicates a defect. 【table】

Claims (1)

[Claims] 1 Formula RO(R'O) _a (C ₃ H ₆ O) _b H (wherein R is a C ₈ to _{C 18} alkyl group, R'O is butylene oxide or butylene oxide and propylene oxide) A group in which a and are randomly polymerized, a
and b are numbers from 1 to 124 and from 1 to 154, respectively, and are determined so that the weight ratio of butylene oxide and propylene oxide is 10:90 to 90:10 and the molecular weight is 500 to 10,000). A hair styling product characterized by containing one or more phosphate esters of oxyalkylene monoalkyl ether.