JPH07106968B2 - Cosmetics containing an esterified product - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION (a) Field of Industrial Application The present invention relates to a cosmetic composition comprising a novel esterification product of dimethylpolysiloxane-modified diol and a saturated or unsaturated, linear or side chain fatty acid. Pertain.

(B) Conventional technology Silicone oil has the following properties: viscosity stability, thermal oxidation stability, lubricity,
It has excellent water repellency, glossiness, rust and corrosion resistance, and is widely applied to anti-vibration oil for instruments, lubricating oil for machinery, water repellent for glass containers, wax additive, defoaming agent, cosmetic additive, etc. Has been done.

Usually, dimethylpolysiloxane is generally used as silicone oil, and other methylphenylpolysiloxane, methylhydrogenpolysiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane,
Dimethyl polysiloxane polyethylene glycol copolymers, dimethyl polysiloxane polypropylene glycol copolymers, etc. are known, but recently, as a silane coupling agent, an organosilicon monomer having two or more different reactive groups in the molecule and These derivatives, as well as various modified silicone oils such as methylstyrene modified, olefin modified, polyether modified, alcohol modified, fluorine modified, hydrophilic special modified, amino modified, mercapto modified, epoxy modified, carboxyl modified, higher fatty acid modified, etc. Yes, these are Shin-Etsu Chemical Co., Ltd., Chisso Corporation,
It is commercially available from Torre Silicone Co., Ltd.

Such silicone oil is also often used as an oil agent for cosmetics, but its main purpose is its foundation that is resistant to makeup makeup and lipstick that spreads easily due to its excellent water repellency, non-adhesiveness, lubricity, etc. Is to get.

However, when it is used as a cosmetic oil, it is required to have the characteristics of silicone oil, high viscosity, no stickiness, and excellent compatibility with other components.

However, conventionally, in order to increase the viscosity of silicone oil such as dimethylpolysiloxane, it has been common to increase the molecular weight, but these high-viscosity silicone oils have very poor compatibility with polar solvents such as ethanol, When it is used in an emulsified system, it is difficult to emulsify, and although it has very high water repellency, it has stickiness and oily luster, and exhibits unfavorable physical properties depending on the purpose of use. Furthermore, highly polar silicone oils such as dimethylpolysiloxane diol have a very high solubility in polar solvents, but on the contrary, have a very poor compatibility with oil agents such as petrolatum, lanolin and vegetable oils.

Tokkai Sho 61-129187 discloses an esterification product of a dimethylpolysiloxane-modified diol and a dibasic acid, which solves the above-mentioned drawbacks.

(C) Problems to be Solved by the Invention The object of the present invention is to eliminate the above-mentioned drawbacks of silicone oil by means other than the method described in JP-A-61-129187, and to eliminate the conventional silicone. It is intended to obtain a cosmetic using a novel silicone-based esterification product having excellent properties that cannot be obtained with oil.

(D) Means for Solving the Problems The present invention is a diol represented by the general formula (I) and having an aliphatic alcoholic hydroxyl group at both ends of dimethylpolysiloxane and having a molecular weight of 300 or more and 7,000 or less (dimethylpolysiloxane-modified). The present invention relates to a cosmetic containing an esterification product of a diol and a fatty acid.

(However, R is a fatty acid residue having 1 to 17 carbon atoms, m is an integer value of 1 to 24, n is 0 or an integer value of 1 to 92) Fatty acids are saturated or unsaturated, straight chain or side chain fatty acids are used. , Considering its compatibility with oils, solvents, etc., oxidation stability, safety, etc., caprolic acid, myristoleic acid, palmitooleic acid, oleic acid, linoleic acid, linolenic acid, caproic acid Fatty acids having 2 to 18 carbon atoms such as caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, isooctylic acid, and isostearic acid are preferable.

The above-mentioned dimethylpolysiloxane-modified diol and fatty acid can be used alone or in combination of two or more.

The esterification reaction is carried out according to a conventional method without catalyst or in the presence of a catalyst under normal pressure or reduced pressure. Then, the esterification is proceeded until the acid value is hardly reduced, and after the completion of the esterification, decolorization with a decoloring agent is performed according to a conventional method, and then deodorization with steam is performed.

Various kinds of cosmetics are prepared by appropriately blending the obtained esterified product with conventional components and optional components. That is, all or part of conventional oil agents, emollient agents and the like are replaced by the esterification product of the present invention and prepared by a conventional method. The amount of the esterification product to be compounded cannot be specified unconditionally, but is generally 0.1 to 30% by weight.

There are no particular restrictions on the type of cosmetics, including cold creams, vanishing creams, creams, lotions, packs, shampoos, conditioners, hair treatments, hair liquids, pomades, lipsticks, blushers, powder cakes, eye shadows, etc. Can be applied.

(E) Example Example 1 Preparation of esterification product Dimethylpolysiloxane modified diol (average molecular weight: about
1,000, viscosity: 33.1 cps / 25 ° C, average degree of polymerization n: about 10) 360 g and caproic acid 104 g were charged into a one-necked flask equipped with a stirrer, a thermometer, a nitrogen gas blowing tube, and a water separator. Add 0.5% of tin chloride as a catalyst and 5% of xylol as a reflux solvent (relative to the total amount of charge) together, stir well,
The mixture was reacted at 160-250 ° C for 11 hours. After the reaction,
The catalyst was filtered off, then decolorized with activated clay, and deodorized by blowing steam under reduced pressure to obtain the desired product (Sample No. 1).

Similarly, the esterification products shown in Table 1 were prepared using dimethylpolysiloxane-modified diols having an average molecular weight of 1,000 (polymerization degree n: about 10 or about 5) and 3,200 (polymerization degree n: about 37). Obtained.

Example 2 Properties of Esterification Product Table 1 shows compatibility of various esterification products shown in Table 1 in Table 1 with solvents and oils.

The compatibility of the dimethylpolysiloxane-modified diol, which is a raw material for the esterification product, is shown in Sample No. 6.

Example 3 Stability Test of Esterification Product Primary irritation to human body was examined by the occlusive patch test as follows.

That is, the sample is applied to a 1-inch square lint cloth excluding the keratin of the anterior arm or the lateral arm epidermis and the sebum on the epidermis, and this is applied to the skin surface, covered with oil paper, and spread on all four sides with a paper bandage. Stop and press on this with a bandage. This test was carried out on 20 healthy persons, and after 24 hours, 48 hours, and 1 week, the judgments were made. The esterification products of the present invention (Sample Nos. 1 to 5) were not found at all. It is not irritating and is useful as a cosmetic oil.

Further, the odor test after coating was carried out as follows. That is, about 0.2 g of the sample was applied to the front arm portion in a size of 2 inches square, and after 10 minutes, 20 minutes, 30 minutes, 1 hour, 4 hours, and 8 hours, the odor was determined by the sense of smell. This test was conducted on 20 healthy people, and the esterification product of the present invention (Sample N
No odor was detected in any of o.1 to 5).

Example 4 Formulation example (1) Foundation (oil-based ointment type) Liquid paraffin 24.0 (%) Isopropyl palmitate 15.0 Lanolin alcohol 2.0 Sample No.1 5.0 Microcrystalline wax 5.0 Candelilla wax 1.0 Ozokelite 8.0 Titanium oxide 15.0 Kaolin 15.0 Talc 6.0 Coloring Pigment 4.0 Preservatives, Antioxidants, Fragrances (2) Mascara Sample No.2 52.0 (%) Carnauba wax 5.0 Candelilla wax 3.0 Microcrystalline wax 9.0 Cholesterol 1.0 Sorbitan monostearate 1.0 Dialkyl ditallow ammonium cellulose derivative 3.0
Aluminum Stearate 1.0 Purified water 5.0 Talc 8.0 Iron oxide black 12.0 Fragrance Suitable amount (3) Blusher Sample No.5 65.0 (%) Carnauba wax 1.0 Microcrystalline wax 5.0 Sorbitan sesquioleate 1.0 Organically modified bentonite 3. Ethanol 5.0 Mica 10.0 Herringdon Pink 5.0 Iron oxide Red 3.0 Iron oxide yellow 2.0 Fragrance (4) Lipstick Candelillo 10.0 (%) Carnauba wax 4.0 Ceresin 3.0 Microcrystalline wax 3.0 Sample No.3 10.0 Liquid paraffin 10.0 Tri-2-ethylenehexanoate glycerin 40.0 Malate diisolate Stearyl 20.0 Red No. 202 Appropriate amount Red No. 226 Appropriate amount Yellow No. 4 Aluminum Lake Appropriate amount Example 5 Evaluation of Cosmetics All of the various cosmetics shown in the formulation examples have good feel, no sticky feeling, good emulsifying properties, and good makeup. Excellent in cosmetics, such as not easily crumbled It was recognized that

The results obtained by continuously applying the sensory superiority and inferiority of the foundation, the lipstick and the commercial product A (Creamy foundation), and the commercial product B (lipstick) shown in Formulation Examples (1) and (4) to 30 women for two weeks. 90%) is shown in Table 3.

(F) Effect of the Invention The esterification product according to the present invention is wavy and odorless, and by changing the types of dimethylpolysiloxane-modified diol and fatty acid, lubricity, viscosity, feel, compatibility, and various other physical properties. Can be changed freely. In addition, even if the viscosity is increased, the feeling of stickiness is extremely low, and when compared to silicone oil of the same viscosity, it has less greasy luster, is non-sticky, and retains the unique slipperiness, water repellency, and gloss of silicone oil. Has been done. It is a highly stable substance that does not irritate the skin and has excellent affinity and feel to the skin, emulsifying properties, moisturizing properties and emollient properties. Various cosmetics can be obtained.

Claims (2)

[Claims] 1. A cosmetic comprising an esterification product of a dimethylpolysiloxane-modified diol having a molecular weight of 300 or more and 7,000 or less represented by the general formula (I) and a fatty acid. (However, R is a fatty acid residue having 1 to 17 carbon atoms, m is 1 to 244
Value, n is 0 or an integer value from 1 to 92) 2. The cosmetic according to claim 1, wherein the fatty acid is at least one kind of saturated straight chain, unsaturated straight chain, saturated side chain and unsaturated side chain.