JPS6020361B2 - skin cosmetics - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to skin cosmetics, and the gist of the present invention is to incorporate N-lower acyl acidic amino acid gester into a cosmetic base as an active ingredient. The purpose of this invention is to obtain various kinds of IQ salmon materials having the following properties.

Cosmetics are originally applied or sprayed for the purpose of directly replenishing moisture, oil, etc. to various parts of the human body for health and hygiene purposes, so sufficient consideration must be given to the selection and formulation of raw materials. is required.

Conventional N- lower acyl acidic amino acid gester
Acetyl aspartate di-n-butyl ester, N-
There are acetylglutamic acid di-n-phthyl esters, etc., and these known N-lower acyl acidic amino acid lower alkyl esters are used in hair cosmetics because they have no toxicity or skin irritation and have the ability to prevent dust adhesion. The present inventor investigated the use of the above esterified products in skin cosmetics such as emulsified and solubilized products and aerosol products, and found that
Satisfactory results were not obtained in terms of the stability, appearance, feel of the emulsified and solubilized products, and the dispersibility of Freon gas.

The present inventors have conducted extensive research to improve the drawbacks of such N-lower acyl acidic amino acid lower alcohol esters, and have found that N-lower acyl acidic amino acids can be converted into higher alcohols, particularly polyoxyalkylene glycol higher alcohol ethers, as described below. Something shaped like a gestal,
Emulsified and solubilized products have extremely excellent performance in terms of stability, appearance, flexibility, emollient properties, opalescence, smoothness, and dispersibility of Freon gas, and are also free of toxicity and skin irritation. It has been found that it is suitable as a skin cosmetic in the perfumery field because of its extremely low content.

That is, the present invention uses an N-lower acyl acidic amino acid gester having an acyl group having 1 to 7 carbon atoms as an active ingredient, and the ester portion of this gester is a higher alcohol (however, the N-lower acyl acidic amino acid ester having an acyl group having 7 carbon atoms) is used as an active ingredient. The present invention is a skin cosmetic containing an N-lower acyl acidic amino acid diester in a form derived from an alcohol selected from the group consisting of amino acid diester) and polyoxyalkylene glycol higher alcohol ether.

The skin cosmetics of the present invention have little change in elevation when used in cosmetics, are extremely irritating to the skin, and have good spreadability, emollient properties, and gloss and opalescence of emulsified products. Very good.

Furthermore, since the dispersibility of Freon gas is extremely improved, it is possible to produce a wide variety of one-component (unseparated, homogeneous liquid) aerosol cosmetics that are not available in other conventional products.

In addition, the dispersibility of the pigment is extremely good and the affinity with the skin is good, so it can be used as an extremely excellent makeup product.

In addition, baby oil has very little toxicity and skin irritation.
Excellent skin ingredient as a base for lipstick, ointment, suppositories, etc.
It is a hoko fee.

In producing the skin cosmetics of the present invention, N-lower acyl acidic amino acids, higher alcohols, and polyoxyalkylene higher alcohol ethers are esterified using known esterification methods, such as heating (normal pressure, reduced pressure) dehydration condensation. reaction, ■ester exchange reaction, ■azeotropic dehydration condensation reaction, etc., but azeotropic dehydration condensation reaction is particularly optimal in terms of reaction conditions, product yield, and purity. .

For example, the following conditions are appropriate. 2.0 to 2.2 mol of higher alcohol or polyoxyalkylene higher alcohol and 10 to 50% of a non-sacrificial solvent such as benzene or toluene per 1 mol of N-lower acyl acidic amino acid (
N-lower acyl acidic amino acid and alcohol (volume % based on the charged amount) were charged into a reactor, mixed thoroughly, and then 0.01 to 0.1 mole of acidic catalyst was added,
Heat at oo for 1 to 1 hour. At this time, water produced as a by-product during the reaction is removed as much as possible to promote the reaction. Of course, even if this method is not used, the acidic amino acid is first reacted with the above-mentioned alcohol under an acidic catalyst to form the corresponding acidic amino acid gester, and then this is reacted with a lower fatty acid halide under an alkali catalyst to perform the so-called Schotten-Bauman reaction. As a result, N-lower acylation is performed by N-
Any method may be used as long as it leads to a lower acyl acidic amino acid gester.

The N-lower acyl acidic amino acid gester synthesized by this method changes from liquid to solid due to the difference in the alkyl group or the number of moles added to the alkyl group and polyoxyalkylene of the higher alcohol, polyoxyalkylene higher alcohol ether. Depending on the purpose of use, the viscosity can be varied from low to high viscosity, and from low to high HLB values.

Of course, during esterification, alcohols may be used as a single component or as a mixture of different types.
Physical property values and HLB for representative examples of skin cosmetics of the present invention
The values and solubility are as shown in Table 1 and Table 2.

Table I Physical properties and HLB value KA of N-lower acyl acidic amino acid gestel: N-cuff.

Loyl-L-glutamic acid *: Liquid at room temperature AA: N-acetyl-L-glutamic acid
※※: Value P in D Kyo 8. ○. 8. :Polyoxyethylene Table-2 Solubility of N-lower asol acidic amino acid gester (2.0*concentration, 40°C) KA: N-cuff.

Loyl-L-glutamic acid 1: Insoluble AA: N-
Acetyl-L-glutamic acid D: Dispersion P. 0
．． 8. Polyoxyethylene S: Soluble N
- Solubility of the lower alcohol esters of long-chain acylglutamic acid and N-lower acylglutamic acid and the higher alcohol ester of N-lower acylglutamic acid of the present invention in various non-gutter organic solvents often used in skin cosmetics. Tested. The results are shown in Table-3. Table -
3 Concentration approximately 2.0, 40°C A: AG-IS: N-acetyl-L-glutamic acid-di-isostearyl ester B: AG-OD: N-acetyl-L-glutamic acid-di-2-octyl dodecyl ester STER 0: KA-OD: N-cabroyl-L-glutamic acid-di-2-octyl dodecyl ester D: AG-
Bt: N-acetyl-L-glutamic acid/dibutyl ester E: AG-Bu: N-acetyl-L-glutamic acid/dibutyl ester F; OG-Me; N-2-ethyl-
Hexanoyl-L-glutamic acid dimethyl ester G
:LG-Ht: N-lauroyl-L-glutamic acid/jetyl ester 1: insoluble, S: soluble As shown in Table 3 above, N-lower acylglutamic acid/higher alcohol ester (A, B, C) of the present invention are N-lower acylglutamic acid/lower alcohol esters (D, E) and N-long chain acylglutamic acid/lower alcohol esters (F, G).
), the solubility in the above-mentioned non-polluting solvents was completely in contrast.

The N-lower acyl acidic amino acid moieties of the N-lower acyl acidic amino acid gester which is the active ingredient of the skin cosmetic of the present invention are N-lower acylasbalagic acid and N-acylglutamic acid, and the lower acyl group has 1 to 1 carbon atoms. Acyl groups derived from saturated and unsaturated fatty acids of No. 7, and may be acyl groups of single composition fatty acids or mixed fatty acids such as acetic acid, butyric acid, caproic acid, etc.

The acidic amino acid component may be either an optically active form or a racemic form. The alcohol used for esterification is selected from higher alcohols and polyoxyalkylene higher alcohol ethers, and the higher alcohols include natural or synthetic aliphatic alcohols having 8 to 30 carbon atoms, such as lauryl alcohol, myristyl alcohol, and cetyl alcohol. In addition to linear alcohols such as alcohol and stearyl alcohol, 2-hexyldecyl alcohol,
Branched chain alcohols such as 2-octyldodecyl alcohol can be mentioned.

Polyoxyalkylene higher alcohol ethers include polyoxyethylene higher alcohol ether, polyoxypropylene higher alcohol ether, polyoxybutylene higher alcohol ether, and polyoxyethylene higher alcohol ether.
Examples include polyoxypropylene and higher alcohol ethers, whose higher alcohol component has a carbon number of 8 to 30.
The number of oxyalkylene added is 1.
~20 mol is suitable. As the acidic catalyst, sulfuric acid, p-toluenesulfonic acid, hydrogen chloride, weakly acidic ion exchange resin, etc. are used.

The N-lower acyl acidic amino acid gester of the present invention has almost no toxicity, no skin irritation, and is extremely stable in itself. Furthermore, it provides flexibility, lubricity, and emollient properties to the skin, so it is particularly suitable for use in cosmetics. It is useful as a residence fee.

Next, examples of the use of cosmetics using the skin cosmetics of the present invention will be shown.

Usage example 1 Cold cream〈Method〉 ■80 qo, ■flood to 85℃, gradually add ■ while stirring ■, add 60 qo while mixing with water cooling.
Obtain ■ by joining at ℃.

<Features> By blending N-caproyl-L-glutamic acid dicetyl ester, a cold cream with strong emulsifying properties, gloss, and strong water repellency can be obtained.

Next, in the above recipe, N-caproyl-L-glutamic acid di-n-butyl ester (B) was added instead of N-caproyl-L-glutamic acid dicetyl ester (A).
) and an additive-free version (C) of both were prepared and subjected to blind sensory tests on a total of 40 adults aged 18 to 25, 20 boys and 20 girls.

The results are shown in the table below.

*The numbers in the table indicate the number of people who judged it to be the best.

Among B and C, B gave considerably better results than C in terms of wettability, but many people judged it to be inferior in terms of spreadability and feeling of use. Regarding the study item, A gave the best results. Furthermore, we will show the results of testing the change over time for the three samples. Emulsion stability (40°C) Emulsion stability △-. A: Separation and deterioration were observed. As a result, A had good stability, C had good stability, and B had poor stability.

As seen in the various tests above, N-Kapro-L
It can be seen that the cold cream containing dicetyl glutamate is far superior as a cosmetic to that containing di-n-butyl ester of N-capro-L-glutamate.

Usage example 2 Emolientoku IJum <Method> ■ 80 o'clock, ■ Heat up to 890, gradually add ■ while stirring ■, and mix with water-cooled oysters.
Obtained by adding ■ to Pi○.

Features> The combination of 2-hexyldecyl N-cabroyl-L-glutamic acid gester provides softness, sliminess, and emollient properties to the skin.

Usage example 3: Emulsion for oily skin <Method> ■ Fill up to 8p0, ■8p0, add ■ while stirring ■, add ■ to 600p after cooling with water. obtain.

<Features> When N-caproyl-L-glutamic acid di-2-decyl dodecyl ester is added, an emulsion with strong opalescence and gloss is obtained, and an emulsion with an extremely light feeling on use is obtained.

Usage example 4 Deodorant lotion <Method> ■ 35:00, ■
3020 to dissolve it uniformly, and add ① while stirring ① to obtain.

<Characteristics> N-caproyl-L-glutamic acid polyoxyethylene (10 mol) oleyl ether diester is extremely excellent as a solubilizer for fragrances, and provides cosmetics with little skin irritation, flexibility, and emulsion properties.
Usage Example 5 Bath Agent <Method> Each component is added and mixed and heated to a temperature of 35 to 4000°C.

Features> N-Caproyl-L-Glutamic Acid Gestel has good affinity with the skin and makes the skin soft, emollient and smooth.

Usage Example 6 Lipstick Brightener <Method> The ingredients of ① are mixed, heated to a temperature of 80°C to 90 qo, the ingredients of ① are added and mixed, and then molded using a lipstick molding machine.

<Characteristics> By using N-capro-L-glutamic acid gester, a glossy lipstick with low toxicity is obtained.

Usage Example 7 Vitamin-containing aerosol lotion <base emulsification><Method> ■ 4000, ■ 35 pm until midnight, add ■ while stirring ■, and then add ■ to obtain.

<Aerosol method> Approximately 10% of the base emulsion amount of fleon gas is added to obtain a one-component milky white liquid. Features > ■ Using N-caproyl-L-glutamic acid gester, a one-component aerosol product can be obtained.

■Since it is one-component, there is no need to shake it before use.

Next, a reference example of the synthesis of N-lower acyl acidic amino acid gester is given. Reference Example 1 Synthesis of N-caproylglutamic acid di-2-hexyldecyl ester 1 mol of N-caproylglutamic acid, 2.1 mol of 2-hexyldecyl alcohol, and 200 ml of benzene as a solvent were charged into a reactor and Catalyst day 2SQO after mixing fly Azusa. Add 015 mol and heat from 80℃ to 125oo
In between, the heated prayer ceremony is held for about 3 hours.

At this time, water produced as a by-product during the reaction is sufficiently removed. After the reaction was completed, the mixture was neutralized with an aqueous solution of caustic soda, and the solvent benzene was recovered to obtain the target product, N-cabroylglutamic acid di-2-hexyldecyl ester. Yield = 98%, specific gravity D* = 0.9
1.A. V. =1.20,S. V. =150.21, P
．． Day. (1.0%)=6.3 Reference example 2N-acetylglutamic acid P. 0. E. (2 mol) oleyl ether diester N-acetylglutamic acid 1 mol and P. 0. E
．． Charge 2.2 moles of oleyl alcohol ether (2 moles) and 300 moles of benzene as a solvent into a reactor, mix thoroughly, add 0.06 moles of catalyst p-toluenesulfonic acid, and add 0.06 moles of catalyst p-toluenesulfonic acid. Heat Toazusa for about 2 hours in between.

Claims (1)

[Claims] 1 An N-lower acyl acidic amino acid diester having an acyl group having 1 to 7 carbon atoms is used as an active ingredient, and the ester portion of this diester is a higher alcohol (however, in the case of an N-lower acyl acidic amino acid diester having an acyl group having 7 carbon atoms) A skin cosmetic containing one or more N-lower acyl acidic amino acid diesters in a form derived from alcohols selected from the group consisting of