JPS61129187A - Esterification product and cosmetic containing same - Google Patents

Abstract

PURPOSE:A novel esterification product that is formed from a dimethylpoly- siloxand=ediol and a dibasic acid, thus being suitable for use in cosmetics, because it has good compatibility with other components and excluding defects of silicone oil such as freeness from stickiness. CONSTITUTION:(A) A dimethylpolysiloxanediol of the formula (n is 0, integer of 1 or more; R is preferably alkyl) and (B) a dibasic acid, preferably of the formula: HOOC (CH2)mCOOH (m is 0-18) a saturated dicarboxylic acid and/or malic or tartaric acid, are subjected to esterification reaction under normal to reduced pressure, when needed, in the presence of a catalyst to give the objective product.

Description

DETAILED DESCRIPTION OF THE INVENTION (a) Industrial Field of Application The present invention relates to a novel esterification product of dimethylpolysiloxane diol and a dibasic acid, and a cosmetic composition containing the same.

(b) Conventional technology Silicone oil has excellent durability, weather resistance, water repellency, rust prevention/corrosion prevention, and lubricity, and is used as a wax additive, a surfactant for car washes, a water repellent for mortar, etc., and rust prevention. It is used in a wide range of applications, including additives for cosmetics, mold release agents for painters, and antifoaming for engine oil.

Generally, silicone oil is commonly dimethylpolysiloxane, and other silicone oils include methylphenylpolysiloxane, methylhydrodienepolysiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane,
Dimethylpolysiloxane polyethylene glycol copolymer, dimethylpolysiloxane polypropylene glycol copolymer, etc. are commercially available, but in recent years organosilicon monomers having two or more different reactive groups in the molecule and these have been used as silane coupling agents. derivatives, as well as various modified silicone oils such as amino-modified, polyether-modified, olefin-modified, epoxy-modified, fluorine-modified, alcohol-modified, and fatty acid-modified silicone oils are commercially available.

Such silicone oils are often used as oils for cosmetics, but their main purpose is to provide a lightweight, refreshing feel and to prevent makeup from fading due to their water-repellent properties. However, when used as a cosmetic oil, it has the characteristics of silicone oil, has a high viscosity, and is not sticky.
Furthermore, it is required to have excellent compatibility with other components.

However, conventionally, to increase the viscosity of silicone oil,
It was common practice to increase the molecular weight, but these highly viscous silicone oils have very poor compatibility with oils and solvents, and when used in emulsifying systems, they are difficult to emulsify.
, and the ta water content was very high, but it was very sticky and had an oily shine, showing physical properties that were unfavorable depending on the purpose of use.

(C) Problems to be Solved by the Invention The purpose of the present invention is to eliminate the above-mentioned drawbacks of silicone oil and to produce a new silicone-based esterified product that has excellent properties that cannot be obtained with conventional silicone oils. The purpose is to obtain used cosmetics.

(d) Means for Solving the Problems The present invention provides an esterification product of a diol having an aliphatic alcoholic hydroxyl group at both ends of a dimethylpolysiloxane represented by the general formula (I) and a dibasic acid; It pertains to cosmetics containing the

(n: an integer of 1 or more) R in the general formula (1) is an alkyl group, and the molecular weight of the general formula (1) is preferably 300 or more and 2,000 or less.

As the dibasic acid, any dibasic acid such as saturated, unsaturated, hydroxy, aromatic etc. can be used, but from the viewpoint of compatibility with oils and solvents, oxidation stability, safety, etc., oxalic acid, malon Acid, succinic acid, glutamic acid, adipic acid, pimelic acid, speric acid, azelaic acid, sebacic acid, dodecanedicarboxylic acid, tetradecanedicarboxylic acid, hexadecanedicarboxylic acid, octadecanedicarboxylic acid, eicosadicarboxylic acid and other fats with carbon atoms of 20 or less Preferred are malic acid and tartaric acid, which are group saturated dibasic acids and hydroxy dibasic acids.

The dimethylpolysiloxane diol and dibasic acid shown above can each be used singly or in a mixture of two or more.

The esterification reaction is carried out without a catalyst or in the presence of a catalyst under normal pressure or reduced pressure according to a conventional method.

Since a product with a low acid value is usually preferable, dimethylpolysiloxanediol is reacted in molar excess, and esterification is carried out until there is almost no decrease in acid value.After the esterification is completed, decolorization is performed using a decolorizing agent according to a conventional method, and then deodorization is performed using steam. Perform purification.

Various cosmetics are prepared by appropriately blending commonly used ingredients and optional ingredients with the obtained esterified product. That is, it is prepared by a conventional method by replacing all or part of conventional oil agents, emollients, etc. with the esterified product of the present invention. Although the proportion of the esterified product cannot be specified in part, it is generally from 0.001 to 30% by weight.

There are no particular restrictions on the type of cosmetics (creams such as cold cream, vanishing cream, emulsion, lotion, pack agent, shampoo, conditioner, hair treatment, hair liquid, pomade, lipstick, rouge, powder cake, eyelash cream, etc.) It can be applied to shadows, etc.

Example 1 Preparation of Esterified Product Dimethylpolysiloxane diol (average molecular weight approximately 700
, viscosity 40CPS/25℃, degree of polymerization n=approx. 5) 400
g and 80 g of succinic anhydride were charged into a 1 liter tetra-Solo flask equipped with a stirrer, a thermometer, a nitrogen gas blowing tube, and a water separator, and 0.3% of the total amount of tin chloride was added as a catalyst, and 5% of kijirole was used as a refluxing solvent. (based on the total amount charged) was added together, stirred well, and the mixture was reacted at 160 to 250°C for 8 hours. After the reaction was completed, the catalyst was filtered off, decolorized using activated clay, and deodorized by blowing steam under reduced pressure to obtain the desired product (sample N11L1).

The esterification products shown in Table 1 were obtained in the same manner.

Example 3 Stability test of esterified product The primary irritation to the human body was investigated by a closed batch test as follows.

That is, remove the dead skin and sebum on the epidermis of the front or side of the upper arm layer, apply the sample to a 1-inch square lint cloth, apply this to the skin surface, cover with oiled paper, and cover all sides with paper bandages. Then press the top with a wire belt. This test was conducted on 20 healthy people, and judgments were made after 24 hours, 48 hours, and 1 week, and all of the esterified products (sample magnets 1 to 8) were found to be completely irritating. It is useful as a cosmetic oil.

Furthermore, an odor test after application was carried out as follows.

That is, about 0.2 g of a sample was applied to a 2-inch square area on the front side, and the odor was determined by smell after 10 minutes, 20 minutes, 30 minutes, 1 hour, 4 hours, and 8 hours. This test was conducted on 20 healthy people, and none of the esterification products (sample magnets 1 to 8) had any odor.

Example 4 Formulation example (1) Emollient cream sample Hiro 1 2.0 Glyceryl monostearate 2.5 Propylene glycol 10. O〃Preservatives, antioxidants, fragrances
Total amount 100X with appropriate amount of purified water
(2) Emollient lotion microcrystalline wax 1.0χ sample 3
'2. O Beeswax
2.0 Liquid paraffin
30. O Aluminum stearate
0.2〃Glycerin 8.0χ
Preservatives, antioxidants, fragrances in appropriate amounts with purified water
Total amount 100χ (3) Foundation (oil-based ointment type) Liquid paraffin 2
4゜Ox Isopropyl palmitate 15゜O〃
Silanone alcohol 2°O〃Sample 11
kL5 5゜0〃Microcrystalline wax 5.0〃Kyandelilla wax
130 Osikelite
8.0 Titanium oxide 15
．． 0〃Kaolin 15.0
“Talc 6.0゜Coloring pigment 4.0〃Preservative, antioxidant, fragrance Appropriate amount (4) Foundation (cake type) Liquid paraffin゛10.O! Sorbitan sesquioleate 3.5〃Sample 11h2
3. Q〃Titanium oxide
10.0X colloidal kaolin
25.0 Talc 45.
1 Red iron 0.8 Yellow iron oxide 2.5 Black iron oxide
0.1〃Preservatives, fragrances
Appropriate amount (5) Lipstick Candelilla wax 10.0χ Carnauba wax 4.0 Ceresin
3. O〃Microcrystalline wax 3.0〃Sample 11m8
10.0 Liquid paraffin 10.0
〃Diisostearyl malate 20.0〃Red 2
No. 02 Appropriate amount red No. 226
Appropriate amount Yellow No. 4 aluminum lake Appropriate amount Black iron oxide Appropriate amount Fragrance, antioxidant Appropriate amount (6) Hair liquid sample 11 kL 2.0〃
Ethanol 64. O〃Fragrance, pigment 1.0〃Purified water
15.0 (7) Cream rinse 1.3 Butylene glycol 3.0 χ cetanol 1.5 Squalane
1.0 Sample floor 5
0.2〃Preservatives, fragrances Appropriate amount Purified water Total amount 100χ Example 5
Evaluation of Cosmetics The various cosmetics shown in the formulation examples all have a good texture.
It was found to be excellent as a cosmetic, as it does not have a sticky feel, has good emulsifying properties, and does not easily smudge.

The sensual superiority and inferiority of the foundation and lipstick shown in formulation examples (3) and (5), commercially available product A (creamy foundation), and commercially available product B (lipstick) were determined by having 30 women use the products continuously for two weeks (recovery rate). 90%) from Table 3, it can be seen that the sensory evaluation of the foundation and lipstick according to the present invention is very excellent.

(e) Effects of the invention The esterification product according to the invention is light-colored and odorless, and the type of dimethylpolysiloxane diol and dibasic acid,
By changing the charging amount (molar excess) and the degree of esterification (degree of polymerization), it is possible to freely change lubricity, viscosity, feel, compatibility, and other various physical properties. In addition, even when the viscosity is increased, there is very little sticky feeling when compared to silicone oil of the same viscosity. It is retained as is.

It is a highly stable substance that does not irritate the skin, has excellent affinity and texture to the skin, and has emulsifying, moisturizing, and emollient properties. A variety of excellent cosmetics can be obtained.

Claims (6)

[Claims] (1) An esterification product of dimethylpolysiloxane diol represented by general formula (I) and a dibasic acid. ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(I) (n: 0 or an integer greater than or equal to 1) (2) The esterified product according to claim 1, wherein R in the general formula (I) is an alkyl group and has a total molecular weight of 300 to 2,000. (3) The dibasic acid has the general formula HOOC(CH_2)_mCO
The esterification product according to claim 1, which is a saturated dibasic acid represented by OH (m=0 or an integer from 1 to 18) and/or malic acid or tartaric acid. (4) A cosmetic comprising an esterification product of dimethylpolysiloxane diol represented by general formula (I) and a dibase. ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(I) (n: 0 or an integer greater than or equal to 1) (5) The cosmetic according to claim 4, wherein R in the general formula (I) is an alkyl group and has a molecular weight of 300 to 2,000. (6) Dibasic acid has the general formula HOOC(CH_2)_mCO
5. The cosmetic according to claim 4, which is a saturated dibasic acid represented by OH (m=0 or an integer of 1 to 18) and/or malic acid or tartaric acid.