JPS5929055B2 - Neopentyl alcohol ester and cosmetics containing it - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula R(CH2OCR')n(I) (wherein R is neopentyl glycol, trimethyl30-
R' is an alkyl residue of 3,5,5-trimethylhexanoic acid, and n is an integer of 2 to 6. ) Neopen 35 tyl alcohol ester and a skin or hair cosmetic containing this ester.

Cosmetics are generally used on the human skin and hair, so it is desirable to use ingredients and properties that are as similar to human sebum as possible for the oil base, which is the main raw material, so that it is gentle on the skin. The absence of irritation is most important.

One possible way to make it similar to human sebum is to introduce a compound with unsaturated bonds, but unsaturated bonds are extremely unstable to light, air, etc. and easily oxidize.

Oxidized compounds are undesirable because they cause strong irritation and toxicity to the skin. The object of the present invention is to provide an oily base that is liquid at room temperature and is stable against oxidation and hydrolysis, has properties similar to human sebum, is non-irritating to the skin, has an excellent feel, and is stable against oxidation and hydrolysis. do.

As a result of various studies, the present inventor has found the above general formula (1
) was found to meet this purpose, and the present invention was completed.

The ester of general formula (1) is neopentyl alcohol and 3
- It can be obtained by esterifying 5,5-trimethylhexanoic acid.

As the above neopentyl alcohol, neopentyl glycol, trimethylolethane, trimethylolpropane, ditrimethylolpropane, pentaerythritol, dipentaerythritol, etc. are used.

A known method can be used for the esterification reaction, and a catalyst may or may not be used.

After the esterification reaction is completed, the reaction mixture is washed with an alkali according to a conventional method, if necessary, decolorized with a decolorizing agent, deodorized and purified by steam distillation, or purified by vacuum distillation.

The obtained esters of the present invention are colorless and odorless, exhibit a liquid state at room temperature, have excellent oxidation stability and alkali hydrolysis resistance, and are non-irritating.

This ester can be used in combination with various cosmetics, such as skin cosmetics such as nutritional creams, milky lotions, bath oils, and lipsticks, and hair cosmetics such as hair oils and hair rinses. That is, in the production of cosmetics by conventional methods, a part of the conventional oily base is used in place of the ester of the present invention.
The cosmetic composition thus obtained has extremely excellent properties for the skin and hair.

Table 1 shows the results of examining the oxidation stability of various esters according to the present invention by an AOM (Active OxygenMethOd) test. As is clear from the table, the ester according to the present invention has very good oxidation stability compared to conventional oil bases for cosmetics such as olive oil. In addition,
In the AOM test, 20 ml of a sample is placed in a blowing tube for AOM measurement, and air is blown into the oil solution at 97.8 ± 0.2°C at a rate of 2.3 ml/sec. Samples are taken at regular intervals, and the peroxide It measures prices of goods (POV).

Table 2 shows the test results of the alkali hydrolysis resistance of various esters according to the present invention.

As is clear from the same table, the ester according to the present invention has excellent alkali hydrolysis resistance compared to conventional oil bases for cosmetics such as olive oil. For the alkali hydrolysis resistance, approximately 27 samples and 25 ml of potassium N/3 ethanol were placed in a flask for saponification value measurement, and a cooling tube was attached to the flask and heated at 85°C.
Measure the saponification value of the sample at regular intervals, and calculate the value separately.
The decomposition rate is determined by dividing by the saponification value when reacting with N ethanol potash at 85° C. for 3 hours.

Table 3 shows the test results of the primary skin irritation test and eye mucosal irritation test for various esters according to the present invention.

As is clear from the table, the ester according to the present invention is non-irritating and is extremely suitable as an oily base for cosmetics. For the skin stimulation test, three male rabbits weighing approximately 3 kg were used, and the hair on the back was removed with clippers, and the sample was
．． Apply 1 ml each and check the degree of redness (erythema), edema, etc. at the application site after 3, 24, and 48 hours.
Judgment is made using a judgment table, where 0 represents no stimulation at all.

In addition, for the eye mucosa test, three female rabbits weighing approximately 2k9 were used, and the sample was given an O. The eye drops were administered in 0.5 ml doses, observed 3 hours, 24 hours, and 48 hours later, and judged with reference to the Draize evaluation table, where 0 indicates no irritation at all. Examples 1 to 6 below show production examples of various esters according to the present invention and analytical values of the products. Example 1 Synthesis of neopentyl glycol di-3,5,5-trimethylhexanate 1.3 mol of neobentyl glycol was placed in a 1' four-tube flask equipped with a stirrer, a thermometer, a nitrogen gas blowing tube, and a water separator. 2.86 mol of 3,5,5-trimethylhexanoic acid and para-toluenesulfonic acid as an esterification catalyst were added at O. 3% and xylene were added at 5% based on the total amount charged, and the reaction was carried out at 160-260°C until the calculated amount of water accumulated in the water separator.

The reaction time required 5 hours. After the reaction was completed, deoxidation was carried out in a conventional manner, followed by decolorization using a decolorizing agent, followed by deodorization under reduced pressure by blowing in water vapor to obtain a colorless and odorless target product. Example 2 Synthesis of trimethylolethane-tri-3,5,5-trimethylhexanate 1 mole of trimethylolethane, 3,5,5-trimethylhexanoic acid 3 in the same manner as in Example 1
．． 3 moles were reacted to obtain a colorless and odorless target product.

Example 3 Synthesis of trimethylolpropane-tri-3,5,5-trimethylhexanate 0.9 mol of trimethylolpropane and 2.97 mol of 3,5,5-trimethylhexanoic acid were reacted in the same manner as in Example 1. A colorless and odorless target product was obtained.

Example 4 Synthesis of pentaerythritate tetra-3,5,5-trimethylhexanate 0.7 mol of pentaerythritate and 3.08 mol of 3,5,5-trimethylhexanoic acid were reacted in the same manner as in Example 1. A colorless and odorless target product was obtained.

Example 5 Ditrimethylolpropane-tetra-3.5
- Synthesis of 5-trimethylhexanate Ditrimethylolpropane O. 7 moles, 3.5.5
-trimethylhexanoic acid 3. A colorless and odorless target product was obtained by reacting 8 moles of O.

Example 6 Dipentaerythritol hexa-3, 5, 5
-Synthesis of trimethylhexanate Dipentaerythritol 1. O mol and 6.6 mol of 3,5,5-trimethylhexanoic acid were reacted to obtain a colorless and odorless target product.

Table 4 shows the analytical values of the above various esters. Examples of cosmetics according to the present invention are shown in Examples 7 to 12 below. Example 7 W/0 type nutritional cream The ingredients in (1) above were heated to 50 to 60°C, stirred and mixed to dissolve, then the ingredients in (2) were added and mixed, and then (
Component 3) was added.

Example 8 After heating and dissolving each component of emulsion (1) at 60 to 80°C, (2
) were added and mixed, and then the fragrance was added and dispersed while cooling.

Example 9 bath oil The above components were heated and stirred at 40 to 50°C.

Example 10 After heating and melting the components of lipstick (1) and mixing them, component (2) was added and well dispersed, to which component (3) was added and molded using a molding machine.

Example 11 hair oil The above components were mixed at 40°C and uniformly dissolved.

Example 12 Each component of transparent oil rinse (1) was heated and fused at 60°C and added to water at 60°C, cooled while mixing, and perfume was added.

Claims (1)

[Claims] 1. General formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ Neopentyl alcohol ester represented by an alkyl residue, R' is an alkyl residue of 3,5,5-trimethylhexanoic acid, and n is an integer from 2 to 6. 2 Neopentyl glycol, trimethylolethane,
trimethylolpropane, ditrimethylolpropane,
Pentaerythritol or dipentaerythritol and 3.
A general formula characterized by an esterification reaction with 5,5-trimethylhexanoic acid ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R is neopentyl glycol, trimethylolethane, trimethylolpropane, ditrimethylolpropane) , each alkyl residue of pentaerythritol or dipentaerythritol, R' is an alkyl residue of 3,5,5-trimethylhexanoic acid, and n represents an integer from 2 to 6). Method. 3 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R is each alkyl residue of neopentyl glycol, trimethylolethane, trimethylolpropane, ditrimethylolpropane, pentaerythritol or dipentaerythritol, R' is an alkyl residue of 3,5,5-trimethylhexanoic acid, and n is an integer from 2 to 6) A skin or hair cosmetic containing one or more neopentyl alcohol esters. .