JPS6043042B2 - Novel esterification products and cosmetics and external preparations containing them - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel polyether polyol-fatty acid monodicarboxylic acid esterification product and cosmetics and external preparations containing the same as an oil agent.

In cosmetic oils, liquid oils generally include liquid paraffin, hydrocarbons such as squalane, animal and vegetable oils, and synthetic oils (e.g. isopropyl myristate), and waxes include wood wax, beeswax, carnauba wax, Lanolin and its derivatives, petrolatum, etc. are used.

However, hydrocarbons such as liquid paraffin are non-polar oils, and when applied to the skin, they affect breathing and normal health.
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Although Γ vegetable oil and synthetic oil are polar oils, they have poor hydrophilicity. Furthermore, since common natural waxes are natural products, it is difficult to stably supply them with a certain quality, and furthermore, they have poor color and odor. Furthermore, there are few oils themselves that are hydrophilic, with the animal oil lanolin and its derivatives being representative examples. However, since lanolin is a natural product, it is difficult to supply it in a stable and constant quality.Furthermore, it has a poor color and odor, and is paste-like or highly viscous, making it uncomfortable to the touch and limiting its range of use. limited. In addition, skin irritation has become a problem in recent years. An object of the present invention is to provide a synthetic oil of an esterified product that is hydrophilic, has excellent compatibility with other oils, has excellent gelation, and is highly stable to the skin. Another object of the present invention is to provide an oil agent suitable for cosmetics and external preparations, which has excellent gloss, oiliness, spreadability, and good affinity for the skin.

J The present invention relates to (i) a polyether polyol obtained by adding an alkylene oxide to a trivalent or higher polyol;
i) at least one selected from saturated linear fatty acids, saturated side chain fatty acids, hydroxy fatty acids, unsaturated fatty acids, and resin acids; and (iii) fatty acid saturated dicarboxylic acids, fatty acid unsaturated dicarboxylic acids, and fatty acid oxydicarboxylic acids. The present invention relates to cosmetics and external preparations containing as an oil agent a synthetic oil consisting of a polyether polyol-fatty acid-dicarboxylic acid esterification product obtained by esterifying at least one selected from the following. In the present invention, synthetic oil has a wide range of viscosity, from liquid oil to paste and wax.
Includes those having a melting point.

The polyether polyol in the present invention is a trihydric or higher polyhydric alcohol (polyol) such as glycerin, diglycerin, trimethylolpropane, pentaerythritol, dipentaerythritol, sorbitol, sucrose, or a mixture thereof. It is a product obtained by adding one or more types of oxides, such as ethylene oxide and propylene oxide, and is prepared by a conventional addition reaction.

The amount of alkylene oxide added is preferably 3 to 0 moles per mole of polyol. It is also possible to use polyether polyols having a similar structure, which are commercially available as raw materials for polyols of various urethane resins or polyester resins. When different types of alkylene oxides are added, either block polymerization or random polymerization may be used. The saturated straight chain fatty acid preferably has 8 to n carbon atoms, and includes, for example, octanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, and behenic acid. The saturated side chain fatty acid is preferably a fatty acid having an alkyl group having 8 to 2 carbon atoms in its side chain, for example 2-. These include ethylhexanoic acid, isomyristic acid, isopalmitic acid, and isostearic acid. As an unsaturated fatty acid, the number of carbons is 16
-22, examples of which include oleic acid, isooleic acid, and linoleic acid.

The hydroxy fatty acid preferably has 12 to 22 carbon atoms, and includes, for example, 12-hydroxystearic acid and ricinoleic acid. For example, rosin acid is used as the resin acid. Next, the fatty acid saturated dicarboxylic acid preferably has 2 to 20 carbon atoms, and examples thereof include malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and dodecanedicarboxylic acid. .

Saturated dicarboxylic acids having alkyl side chains, such as isopropylsuccinic acid, may also be used. The fatty acid unsaturated dicarboxylic acid preferably has 4 carbon atoms, and includes, for example, maleic acid and fumaric acid. Furthermore, examples of oxydicarboxylic acids include malic acid,
Tartaric acid is used. The polyether polyol, fatty acid, and dicarboxylic acid shown above can be used individually or in a mixture of two or more.

In order to produce the esterified product according to the present invention, a polyether polyol, a fatty acid, and a dicarboxylic acid may be reacted simultaneously, or a polyether polyol and a fatty acid or a polyether polyol and a dicarboxylic acid may be reacted first and then a polyether polyol and a dicarboxylic acid may be reacted. may be reacted with dicarboxylic acid or fatty acid.

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. Esterification is continued until there is almost no decrease in acid value, and after the esterification reaction is completed, decolorization using a decolorizing agent and deodorizing purification by steam distillation are carried out in accordance with conventional methods. The esterified product thus obtained is light-colored and odorless, does not irritate the skin, has excellent affinity and texture to the skin, and is suitable as an oil for cosmetics and external preparations (e.g., ointments). It has the following characteristics.

In addition, the esterified product of the present invention is characterized by the type of polyether polyol, the type of alkylene oxide, the number of moles added,
Depending on the type and combination of fatty acids, the type of dicarboxylic acid, etc., oils with various physical properties can be obtained, from liquid oils to pastes and waxes.

Synthetic oils with hydrophilicity, lubricity, gelling power, compatibility, viscosity, melting point, etc. adjusted arbitrarily can be obtained, and various cosmetics can be prepared using this as an oil agent by appropriately blending common ingredients and optional ingredients. and external preparations can be prepared. It is prepared by a conventional method by replacing all or part of conventional oils, waxes, emollients, gelling agents, etc. with the above esterified product. Although the amount of the esterified product cannot be absolutely specified, it is generally 0.2 to 60% by weight. The present invention will be explained by examples.

Example 1 Preparation of esterified products and their properties 1-1 Preparation of polyether polyol In an autoclave with a capacity of 5e, 2 mol of glycerin and caustic soda as a catalyst were added at a rate of 0.0 mol per glycerin charge. After adding 1% of slag and replacing the atmosphere with nitrogen gas, 1
00~150℃, 1~5k9/C! A predetermined amount of alkylene oxide such as ethylene oxide, propylene oxide, etc. was added in 1 liter and an addition reaction was carried out, and the catalyst was removed to obtain a polyether polyol in which a predetermined amount of alkylene oxide was added to glycerin.

Various polyether polyols were obtained in the same manner using the formulations shown in Table 1.

1-2 A predetermined amount of various polyether polyols obtained in esterification reaction 1-1 was charged into a 4-tube flask equipped with a stirrer, a thermometer, a nitrogen gas blowing tube, and a water separator, and the fatty acids and dicarboxylic acids shown in Table 1 were added. Add a predetermined amount of the mixture, add 0.3% of the total amount of tin chloride as a catalyst, and 5% of the total amount of xylol as a reflux solvent, stir well, and make the mixture
The reaction was carried out at 0°C until the calculated amount of water collected in the water separator.

The time required was approximately 8 hours. After the reaction was completed, the catalyst was separated, decolorized using activated clay, and deodorized by blowing steam under reduced pressure to obtain the desired esterified products shown in Table 1. 1-3 Properties of Esterified Product When the acid value, saponification value, hydroxyl value, viscosity, melting point, etc. of the esterified product shown in Table-1 were measured, the results shown in Table-2 were obtained.

Furthermore, the water-holding power, compatibility with various oils, and gelling power of each sample were measured, and the results shown in Table 3 were obtained. According to the present invention, it is possible to obtain synthetic oil in various forms from liquid to paste and wax as needed, and the type of polyhydric alcohol, the number of added moles of alkylene oxide, the type of fatty acid, the type of dicarboxylic acid, It is possible to obtain oils having various properties such as hydrophilicity, gelling power, and lubricity by changing the blending ratio.

In addition, the presence or absence of skin irritation and odor of the esterified product was also investigated.

First, the primary irritation to the human body was investigated using a closed batch test as follows. That is, remove the dead skin and sebum on the epidermis of the forearm or flexor side of the upper arm, apply the sample to a 1-inch square Lynch cloth, apply this to the skin surface, cover it with oiled paper, and cover it with a paper bandage on all sides. Attach it to the crossbeam and press the top with a woven belt. This test was conducted on 20 healthy people, and evaluations were made after 2 hours, after 1 week, and after 1 week, all of the esterified products (Nos. 1 to 18) were found to be completely irritating. It is useful as a base for cosmetics. Further, an odor test after application was conducted as follows.

That is, approximately 0.2 g of the sample was applied to a 2 inch square area on the front binding part, and after 1 coat, after 2 coats, after 3 coats, after 1 hour, after 4 hours, and after 8 hours.
After a period of time, the odor was determined based on the sense of smell. healthy person 2
This test was conducted on 0 people, but this esterification product (
No. No odor was detected in any of samples 1 to 18). Example 2 Preparation of cosmetics and ointments Cosmetics and ointments were prepared by blending the above ester products with conventional ingredients.

Samples 1 to 18 were used as esterified products and other ingredients were appropriately blended to produce cosmetics of Formulation Examples 1 to 9 and ointments of Formulation Example 10, but all of them had good permeability. Indicated.

Claims (1)

[Claims] 1(i) (polyether polyol obtained by adding alkylene oxide to a trivalent or higher polyol, (ii) saturated linear fatty acid, saturated side chain fatty acid, hydroxy fatty acid,
Polyether polyol-fatty acid obtained by esterifying at least one selected from unsaturated fatty acids and resin acids and (iii) at least one selected from fatty acid saturated dicarboxylic acids, fatty acid unsaturated dicarboxylic acids, and fatty acid oxydicarboxylic acids. - Cosmetics and external preparations containing synthetic oils made of dicarboxylic acid esterification products as oil agents.