TW200301708A - Ester-containing oils and external preparations for skin and cosmetics containing the oils - Google Patents

Abstract

An oil which contains an ester of a branched fatty acid of the general formula (I) wherein R1 and R2 are each a hydrocarbon group and a mono- or polyhydrie alcohol and is excellent in stability to acid or alkaline hydrolysis; high-viscosity oils are also provided, which are excellent in stability to acid or alkaline hydrolysis, feelings in application to the skin, gloss, moisture permeability, shape retention, dispersion of pigment, and so on; and external preparations for skin and cosmetics, containing the same are additionally provided.

Description

200301708 Intellectual Property Bureau of the Ministry of Economic Affairs a (Industrial and Consumer Cooperation Ti India ¾ A7 B7 V. Description of the Invention (1) Technical Field of the Invention The present invention relates to an oil agent containing an ester compound composed of a specific branched fatty acid and a mono or polyhydric alcohol, and Skin external preparations and cosmetics using this oil. More specifically, it has excellent acid or alkali hydrolysis stability, good skin feel, gloss, water vapor permeability, etc., shape retention, and dispersibility such as pigments. Excellent high-viscosity oil, and skin external preparations and cosmetics using the oil. Previous technology Today, oils containing ester compounds are used for various applications. For example, isostearates that have been marketed or contain isostear There are many types of fatty acid oils depending on the structure of the ester compound, and their applications range from industrial products to pharmaceuticals, cosmetics, and food. As the type of isostearic acid in oils, there are the following chemical formulas Emersoll875Isosteraric Acid [Chemical Formula (II)] by Kegonis Corporation, PRISORINE ISAC3 5 05 by Youkuya Corporation [ There are many types such as Chemical Formula (II)] and [Chemical Formula (ΠΙ)] produced by Mitsubishi Chemical Corporation, and their structures are diverse. Isostearate-containing oils are mainly used for skin external preparations when used in pharmaceuticals. When used in cosmetics, it can improve the effect of isostearic acid, water vapor permeability, and antioxidant properties, so it can be used in cosmetics, facial cleansers, soaps, skin cleansers, etc. Oils containing isostearate It is also used in dishwashing or household or household detergents. For example, in oils that are frequently used in cosmetics, ester compounds made from branched fatty acid isostearic acid, such as triisostearyl Diglyceride (please read the precautions on the back before filling in this page), 11-line paper size applies Chinese National Standard (CNS) A4 (210X 297 mm) -5-200301708 A7 B7 V. Invention Explanation f) An ester has excellent functions in terms of usability, shape retention, moisturizing effect, emollient effect, etc. However, the ester compound is a compound (11) or (III) shown below

CI-i2) mCH (CH2) ftCO〇H CH3 (II) [where m and n 値 are m + n = 1 4]

CH3 (CHJ gCHCOOH (Please read the precautions on the back before filling in this page-the ester compound formed by fatty acids and alcohols with the structure of c h2 (ch2) 5ch3 (III), and containing the following formula (I), * =% »R i-ch2 r2-ch (ch3)〉

CHCOOH line [In the formula, I and R2 represent hydrocarbon groups] The 4th Bureau of the Ministry of Economic Affairs, Zhi Cong Cai: Printed by the Shellfish Consumer Cooperative,% 1 The oil of ester compounds composed of multi-branched fatty acids and alcohols with specific structures is unknown until now. On the other hand, until now, fatty acid ester compounds have been used in the manufacturing process for acid or alkali, and the final product has been stored at high temperature or for a long time. The acid or alkali can hydrolyze the ester bond and increase the acid value. There are problems such as skin irritation and odor. However, in the past, from the aspect of quality management, oils with high stability to acids or bases have been expected in various fields. This paper size is applicable to China National Standard (CNS) A4 (210x 297 mm) -6-200301708 A7 B7 fatty acid ester can be used for a wider range of purposes. 5. Description of invention f) Also, because of the high stability invention Therefore, the object of the present invention is to provide an oil agent having acid hydrolysis resistance or alkali hydrolysis resistance, and skin external preparations and makeup mouths containing the oil agent. In view of the above-mentioned situation, the details of the present inventors Investigating results' An oil agent containing a branched fatty acid represented by the aforementioned chemical formula (I) and an ester compound composed of a monohydric or polyhydric alcohol was found and obtained. The oil agent has an acid hydrolysis resistance or an alkali hydrolysis resistance. Use as a skin external preparation or cosmetic. That is, the present invention provides an oil agent containing an ester compound composed of a branched fatty acid represented by the following chemical formula (I) and a monovalent or polyhydric alcohol (please read the precautions on the back before filling this page)- R 1- ch2 R 2 ~ Ch (ch3) >

C H c O OH (I) line Ministry of Economic Affairs smart money / i ^ 7a: Industrial and consumer cooperation Ti Incineration [wherein Ri and R2 represent hydrocarbon groups]. The oil agent provided by the present invention is preferably an ester compound composed of a branched fatty acid represented by the general formula (1), a fatty acid other than the branched fatty acid represented by the general formula (I), and a polyhydric alcohol. In the oil agent provided by the present invention, it is preferable that the fatty acid other than the branched fatty acid represented by the general formula (1) is one or more kinds selected from linear saturated or unsaturated fatty acids, branched saturated or unsaturated fatty acids, And the size of this paper is applicable to China National Standard Soap (CNS) A4 specification (210X 297 mm) -7-200301708 A7 Printed by the Industrial and Commercial Consumers ’Cooperative of the Bureau of Intellectual Property 1 of the Ministry of Economy 5. Saturation or Unsaturation Groups of fatty acids. The oil agent provided by the present invention is preferably a branched hydrocarbon group in which one or both of R1 and R2 of the branched fatty acid represented by the general formula (I) are branched. The above-mentioned oil agent provided by the present invention is preferably the general formula (I), Ri and R2 may be the same or different from each other, and the straight or branched chain or cyclic carbons of 1 to 12 are saturated or unsaturated. Alkyl. The above-mentioned oil agent provided by the present invention is preferably a general formula (wherein Ri is (CH3) 3CCH2CH (CH3) CH2 group, and R2 is (ch3) 3cch2 group.) The above-mentioned oil agent provided by the present invention, Preferably, the monohydric alcohol is one or more members selected from the group consisting of isooctanol, isotetradecanyl alcohol, isopalmityl alcohol, isostearyl alcohol, isicosanol, isosicosanol, and the polyhydric alcohol is one or more members selected from Glycerol, diglycerin, diglycerin, polyglycerol, ethylene glycol, diethylene glycol, 1,3-butanediol, 3-methyl-1,3-butanediol, propylene glycol, dipropylene glycol, Tripropylene glycol, polyethylene glycol, hexanediol, erythritol, pentaerythritol, dipentaerythritol, trimethylolpropane, ditrimethylolpropane, sorbitol, ethyl cellosolve, butyl cellosolve, ethylcarbitol and Groups of butyl carbitol. The other oil agent provided by the present invention, the hydroxyl value of the oil agent is preferably 0 to 400, more preferably 値 in the range of 0 to 80. The present invention provides In addition, the above-mentioned oil agent is preferably one containing the above-mentioned ester compound that is resistant to acid hydrolysis or alkali hydrolysis. (Please read the note on the back first Please fill in this page again)-Binding and binding The paper size is applicable to China National Standard (CNS) A4 (210X 297 mm) · 8-200301708 A7 B7 V. Description of the invention () The present invention also provides an oil containing the aforementioned oil The present invention preferably provides the aforementioned cosmetic product containing tincture. The present invention more preferably provides the aforementioned cosmetic material in the form of lipstick, bright lipstick, lipstick, eye shadow, blush, lotion or lotion. The present invention also provides the use of the aforementioned oil agent in the manufacture of an external preparation for skin. The present invention further provides the use of the aforementioned oil agent in the manufacture of cosmetics. Embodiments Hereinafter, an oil agent containing the ester compound of the present invention will be described first. The present invention is an oil agent, an acid hydrolysis-resistant oil agent or an alkali-hydrolysis-resistant oil agent containing an ester compound composed of a branched fatty acid having a specific structure and a monovalent or polyhydric alcohol. The branched fatty acid constituting the ester compound will be described. The branched fatty acid It is represented by the following chemical formula (I). That is, the fatty acid branched at the carbon site at the α position, and A branched branched fatty acid. The carbon at the α or 0 position is the carbon indicated by the index in the following chemical formula. Buttons-(Please read the precautions on the back before filling this page) Thread Bureau of Wisdom and Finance, Ministry of Economic Affairs

[In the formula, ι and r2 represent a hydrocarbon group]. This paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) -9-200301708 A7 B7 The Smart Finance Bureau of the Ministry of Economic Affairs a: Industry 4 Fee Cooperative Cooperative Printing 5. Description of the invention () For the above branched fatty acids, In other words, Rp R2 represents a branched hydrocarbon group on either or both sides. As the hydrocarbon group, Ri and the same or different from each other may be used. The number of carbons is preferably 1 to 12, and more preferably 3 to 8 straight or branched. Chain-like saturated or unsaturated hydrocarbon group. The position of the side chain is not particularly limited. Ri represents a branched saturated hydrocarbon group having 1 to 12 carbon atoms, preferably 3 to 8, and R 2 represents 1 to 12 carbon atoms. A branched saturated hydrocarbon group of 3 to 8 is preferred. As such a branched fatty acid, I of the chemical formula (I) may be a CH3 (CH2) 2CH (CH3) CH2 group, and R2 may be a branch of a CH3 (CH2) 2 group. Fatty acids are preferred. Examples of such branched fatty acids include isododecanoic acid [trade name: isotetradecanoic acid] made by Nissan Chemical Co., Ltd., and Ri is represented by the formula (I) as (CH3) 3CCH2CH ( ch3) ch2 group, r2 represents the branched fatty acid of (ch3) cch2 group is the best. Examples of such branched fatty acids include isostearic acid (trade name: isostearic acid) made by Nissan Chemical (Trade) Co., Ltd. When synthesizing the ester compound used in the present invention, a compound of general formula (I) can be used alone A branched fatty acid represented by the formula, or a combination of two or more types. As the branched fatty acid represented by the general formula (I) used in the present invention, a commercially available one can be used, or it can be produced by chemical synthesis. The monohydric or polyhydric alcohol of the compound will be described. The monohydric compound constituting the aforementioned ester compound refers to an alcohol having one hydroxyl group in one molecule. The position of the hydroxyl group is not particularly limited. The carbon number of the monohydric alcohol is preferably 1 to 26. , Preferably from 8 to 26. Examples of such a monohydric alcohol include methanol, ethanol, n-propanol, n-butanol, n-hexanol, phenol, benzyl alcohol, n-octanol, n-nonanol, n-decanol, Lauryl alcohol, methyl tetradecanol, (Please read the precautions on the back before filling out this page)

'1T paper size is applicable to Chinese National Standard (CNS) A4 specification (210X 297 mm) -10-200301708 A7 B7 V. Description of invention () (Please read the notes on the back before filling this page) Palm alcohol , Alcohol, Stearyl alcohol, Stearyl alcohol, Oleyl alcohol, and Behenyl alcohol, isopropyl alcohol, isobutanol, isoamyl alcohol, isohexanol, isoheptanol, isooctanol Alcohols, isononyl alcohol, isodecanol, isoundecyl alcohol, isotetradecanyl alcohol, isopalmityl alcohol, isostearyl alcohol, isoicosanol and isohexacosanol, and branched alcohols Various cyclic alcohols such as propanol, cyclobutanol, cyclopentanol, and cyclohexanol. Among them, branched alcohols, particularly branched alcohols having 8 to 26 carbon atoms, and more particularly one or more selected from the group consisting of isooctanol, isododecanol, isopalmityl alcohol, isostearyl alcohol, isicosanol, Isohexacosanol is preferred because it can produce an ester compound having excellent resistance to acid hydrolysis or alkali hydrolysis. The polyhydric alcohol constituting the aforementioned ester compound by the Ministry of Economic Affairs, the Intellectual Property Bureau of Finance, Xiao Gong Consumer Cooperative, refers to having two or more hydroxyl groups in one molecule, preferably having 2 to 6, and most preferably having 3 to 4 Of alcohol. The number of hydroxyl groups is not particularly limited as long as it is only 2 or more. The carbon number of the polyol is preferably 2 to 30, and more preferably 2 to 12. Examples of such a polyol include glycerol, diglycerol, diglycerol, polyglycerol, ethylene glycol, diethylene glycol, 1,3-butanediol, and 3-methyl-1,3 -Butanediol, propylene glycol, dipropylene glycol, tripropylene glycol, polyethylene glycol, hexanediol, erythritol, pentaerythritol, dipentaerythritol, trimethylolpropane, ditrimethanolpropane, sorbitol, ethyl cellosolve, Butyl cellosolve, aliphatic polyalcohols such as ethyl carbitol and butyl carbitol, monosaccharides such as glucose, fructose, mannose, galactose, xylose, arabinose, and ribose, disaccharides such as maltose, lactose, and sucrose Sugars, sugar alcohols such as mannitol, sorbitol, and maltitol. Among them, the aliphatic polyol is particularly an aliphatic polyol having 2 to 12 carbon atoms and 2 to 6 hydroxyl groups, and glycerin and diglycerol are particularly preferable. As the ester compound of the present invention, for one molecule of polyhydric alcohol, in addition to the paper size, the Chinese National Standard (CNS) Λ4 specification (210X 297 mm) is applicable. -11-200301708 Consumption cooperation T1 ¾ A7 _B7 V. Description of the invention () As a fatty acid, one or more molecules other than the branched fatty acid represented by the general formula (I) can be used in combination with the branched fatty acid represented by the general formula (I) Produced by fatty acids. By using a fatty acid other than the branched fatty acid represented by the general formula (I) in combination, it is preferable to control the viscosity of the oil agent or change the feel. Examples of fatty acids other than the branched fatty acids represented by the general formula (I) include linear fatty acids, branched fatty acids, saturated fatty acids, unsaturated fatty acids, and the like, and for example, hexanoic acid, caprylic acid, capric acid, lauric acid, Alkanoic acid, palmitic acid, stearic acid, behenic acid, isoheptanoic acid, isooctanoic acid, isodecanoic acid, isoundecanoic acid, isododecanoic acid, isopalmitic acid, linoleic acid, linolenic acid, and Erucic acid and so on. Within the range of the branched fatty acids represented by the general formula (I), the carbon number and side chain position of these fatty acids are not particularly limited. Among them, linear saturated or unsaturated fatty acids, branched saturated or unsaturated acids, or cyclic saturated or unsaturated fatty acids are preferred. Fatty acids other than the branched saturated acid represented by the general formula (I) can be used alone or in combination of two or more kinds. As for the fatty acid constituting the ester compound of the present invention, the molar ratio of the branched fatty acid represented by the aforementioned general formula (I) to other fatty acids is 1: 0 to 1: 9 and preferably 1: 0 to 1 · 4 . Such a comparison is preferable because it has characteristics such as the hydrolytic stability of the branched fatty acid represented by the formula (I), and also provides the viscosity adjustment function of a fatty acid in combination. The ester compound composed of the aforementioned branched fatty acid and mono- or polyhydric alcohol which can be used in the present invention is a compound in which the aforementioned branched fatty acid is ester-bonded to a mono- or polyhydric alcohol having 1 or 2 or more hydroxyl groups. In the oil of the present invention, it is preferable to mix two or more of these ester compounds. One yuan or more (please read the note on the back to fill in this page first)-The size of the binding gauze paper is applicable to the Chinese National Standard (CNS) A4 (210X 297 mm) -12-200301708 A7 B7 V. Description of the invention () When the number of fatty acids that are ester-bonded to the alcohol is defined as follows due to the hydroxyl value, an oil agent having better resistance to acid hydrolysis and alkali hydrolysis can be obtained. The preferred hydroxyl value of the oil of the present invention is in the range of 0 to 400, more preferably 0 to 200, and most preferably 0 to 80. When the hydroxyl value of the oil agent is within such a range, it is excellent because it has excellent acid hydrolysis resistance and hydrolytic resistance. The content of an ester compound composed of a branched fatty acid having a specific structure in the oil agent of the present invention, and a monovalent or polyhydric alcohol, and the content of the aforementioned ester compound in the acid hydrolysis-resistant or alkali-resistant hydrolysis oil agent of the present invention are preferred. It is i 0 mass% or more, preferably 30 mass% or more, more preferably 50 to 100 mass%, and particularly preferably 70 to 100 mass%. Particularly, if the content of the aforementioned ester compound in the oil agent of the present invention is 70% by mass or more, its viscosity is high (for example, when the triisostearic acid diglycidyl group represented by the general formula (I) is about 1 5000 ~ 3 000〇1 ^ &. 5/25 ° (:), excellent shape retention, dispersibility of pigments, etc. For the acid hydrolysis-resistant oil agent of the present invention, acid hydrolysis resistance refers to the ester compound in the acidic aqueous solution. The ester-bonded part is not easily decomposed by water and has stable properties. For example, the oil agent of the present invention is stable at pH 0.5 and 90 ° C after heating for 5 hours. The alkali-hydrolyzable oil agent of the present invention is also stable. Alkali hydrolysis resistance refers to those with stable properties in which the ester bond portion of the ester compound in the alkaline aqueous solution is not easily hydrolyzed. For example, the oil agent of the present invention is not hydrolyzed by heating at 85 ° C for 5 hours at pH 14 And the skin external preparations or cosmetics containing these acid hydrolysis resistance or alkali hydrolysis resistance, in the formulation or manufacturing process, even if there are citric acid or salicylic acid, this paper standard applies to Chinese National Standard (CNS) A4 specifications (210X 297mm) -13 -------- Installation-I (Please read the precautions on the back before filling out this page) Thread: Wisdom / i Bureau of the Ministry of Economic Affairs: Printing and Publishing Co., Ltd. of the Ministry of Economic Affairs Bone removal cooperation seal ^ A7 B7 JO-V. Description of the invention () In the presence of acidic substances or basic substances such as triethanolamine or aromatic amines, hydrolysis will not cause skin irritation or odor causes. Fatty acids are free and the system does not become unstable. It can also be used in products that have not been used in households other than cosmetics, car lotions, soaps, lubricants, oils and other products that are resistant to acid hydrolysis or must be alkaline. The use amount of the oil agent of the present invention in these products is not limited. Second, the production of the oil agent of the present invention can be produced, for example, by the following method, but is not limited thereto. That is, the general formula (I) When branched fatty acids are used in combination, fatty acids other than the fatty acids represented by the general formula (I) are injected with an appropriate amount of a monovalent or polyhydric alcohol, and in the absence of a catalyst or catalyst, the solvent is dehydrated at reflux or under reduced pressure. After the completion of the esterification reaction, if necessary, the reaction mixture is decolorized or deodorized by a decolorizing agent, and then purified by vacuum distillation to obtain the desired oil agent. Next, the product containing the oil agent of the present invention can be obtained. The skin external preparation will be described. Among them, the skin external preparation of the present invention can be used as a main medical person, and examples thereof include ointments or creams. As the oil for the skin external preparation, only the oil preparation of the present invention can be used, or A part of the oil agent and emollient in the skin external preparation can be replaced by the oil agent of the present invention. The content of the oil agent of the present invention contained in the skin external preparation is better for the overall quality of the skin external preparation It is 1 to 80% by mass, more preferably 20 to 60% by mass. When the content of the oil agent of the present invention in the skin external preparation is within the above range, the acid or alkali of the skin external preparation of the present invention is hydrolyzed and stable to the skin. The use feeling, color, water vapor permeability, shape (please read the precautions on the back before filling this page)

1. The paper size of the 1T line is applicable to the Chinese national standard (CNS) A4 size (210X 297 mm) -14-200301708 A7 B7 Printing by the Goods and Consumers Cooperative of the Intellectual Property Finance Bureau of the Ministry of Economic Affairs 5. Disclosure of the invention () Retention, It is better to improve the dispersibility of pigments and other effects. In addition, the residual portion is divided into arbitrary components. Among them, the effect on the skin is that it can be uniformly extended when the skin external preparation is applied. The water vapor permeability refers to the external water vapor permeability released from the skin through the skin external preparation when applied to the skin external preparation. Generally speaking, the water vapor permeability is 100% when there is no substance applied on the skin. If it is 10 to 60%, it indicates that the water vapor permeability effect is present, and 60% or more indicates that the water vapor permeability effect is high. The so-called shape-retaining effect refers to the effect that a solid skin external preparation or a solid cosmetic product, such as a medicinal lipstick or lipstick, can be stored for a long time without losing its shape. In addition, in terms of dispersibility such as pigments, for external preparations or cosmetics containing fine powders such as pigments, oily components such as pigments such as pigments do not cause aggregation or precipitation in oily components, and they have a stable and uniform dispersion effect. The skin external preparation of the present invention may suitably add generally added alcohols, fatty acids, fatty acid esters, flowing stone extracts, petrolatum, vegetable oils and fats, animal oils and fats, antioxidants, antiseptic and fungicides, emulsifiers, Surfactants, pigments, pigments, perfumes, waxes, UV absorbers, plant extracts and pigments. In addition, although the method for producing a skin external preparation containing the oil agent of the present invention is not particularly limited, a generally widely-used production method can be used. Next, the cosmetics containing the oil agent of the present invention will be described. Among them, the cosmetics of the present invention are mainly used by beauty users. Although the types of the cosmetics are not particularly limited, for example, red lipstick, bright lipstick, lipstick, eye shadow, Blush, lotion and lotion. As an oil in cosmetics, only use it (please read the precautions on the back before filling out this page) Gutter This paper size is applicable to China National Standard (CNS) A4 (210X 297 mm) -15 · 200301708 Α7 Β7 Ί〇- 5. Description of the invention () The oil agent of the present invention is sufficient, but a part of the oil agent and the emollient in cosmetics can be replaced by the oil agent of the present invention. The content of the oil agent of the present invention contained in a cosmetic is preferably 1 to 80% by mass, and more preferably 20 to 60% by mass based on the total mass of the cosmetic. When the oil agent of the present invention is contained in the above-mentioned range, the effects such as stability of acid or alkali hydrolysis, skin feeling, color, water vapor permeability, shape retention, and dispersibility of pigments and the like are improved. . And the residual part may be an arbitrary component. In the cosmetic of the present invention, generally added alcohols, fatty acids, fatty acid esters, flowing stone, vegetable fats, animal fats, antioxidants, preservatives, fungicides, emulsifiers, surfactants, Pigments, pigments, fragrances, tinctures, UV absorbers, plant extracts and pigments. In addition, the type of the cosmetic containing the oil agent of the present invention is not particularly limited, and examples thereof include hair cosmetics, shampoo cosmetics, lotions, emulsions, milky emulsions, face creams, foundations, white powders for powdering, lipsticks, Bright lipstick, lipstick, eyebrow cosmetics, eye shadow, blush, lotion, nail cosmetics, bath cosmetics, facial cleanser and soap. In particular, from the viewpoint of the dispersing function of oil pigments, it is excellent for the use of makeup cosmetics such as lipsticks and foundations. In addition, although the manufacturing method of the cosmetics containing the oil agent of this invention is not specifically limited, The manufacturing method generally used widely can be used. Implementation method Example This paper size is applicable to Chinese National Standard (CNS) M specification (210 × 297 mm) _ 16 (Please read the precautions on the back before filling this page)

Ministry of Economic Affairs, Zhicongcai / 1 Bureau: ^ Work 4 cost cooperation seal ^ 200301708 A7 B7 13 ----- V. Description of the invention () The following examples are used to explain the present invention in more detail, but the invention is not limited by these limit. Example 1 Preparation of glyceryl triisostearate First, 272 g of the above formula (I) is 1 (ch3) 3CCH2CH (ch3) ch2 group, and r2 is (st3) 3cch2 group isostearic acid [Nissan Chemical (Isostearic acid, made from stock) and 28 g of glycerin were put into a 500-ml four-necked conical flask equipped with a stirrer, thermometer, nitrogen blowing pipe, and water separating pipe, and 0.3% of tin chloride powder was used as the total amount. For the catalyst, 5% of the mixed xylene was used as a reflux solvent. After all the mixture was added, the mixture was reacted at 200 ~ 250 ° C for 15 hours while stirring. After the reaction was completed, the clay was decolorized with active clay and deodorized by a conventional method to obtain 2 1 g of an oil agent containing glyceryl triisostearate. The glyceryl triisostearate content in the oil agent was 78% by mass, and the hydroxyl value of the oil agent was 20. Example 2 Preparation of triisostearic acid diglyceride The same isostearic acid [made by Nissan Chemical Co., Ltd., isostearic acid] 25 4 g and 46 g of diglycerin were used to prepare The same esterification reaction as in Example i gave 2 1 Og of an oil agent containing diglyceryl triisostearate. The content of the diglyceryl triisostearate in the oil agent was 45 to 5% by mass, and the hydroxyl value of the oil agent was 45. Comparative Example 1 Preparation of diglyceryl triisostearate First, 254 g of the isotope made of the fatty acid of the above chemical formula (Π) was applied to the standard paper size of China National Standard Leather (CNS). (210 × 297 mm 4) ( Please read the notes on the back before filling out this page) -Installation-Wisdom Finance 4th Bureau of the Ministry of Economics and Economics: T1 Printing of Consumers' Cooperative ¾ -17- 200301708 Wisdom Finance / 4th Bureau of the Ministry of Economics: Printing and Printing of A7 B7 -Ϊ4 —- 5. Description of the invention () Fatty acid [made by U-Keya, PRISORINE ISAC3505] and 46 g of diglycerin, put in 500 ml with stirrer, thermometer, nitrogen blowing tube, water separation tube In a four-necked conical flask, 0.3% of tin chloride powder was used as a catalyst, and 5% of mixed xylene was used as a reflux solvent. After all the mixture was added, the mixture was stirred to 200 ~ 250. (: React for 20 hours. After the reaction is completed, decolorize with activated clay and deodorize in accordance with the usual method to obtain 210 g of an oil agent containing diglyceryl triisostearate. Triisostearic acid di in the oil agent The glyceride content was 40% by mass, and the hydroxyl value of the oil agent was 43. [Alkali hydrolysis resistance test of oil agent] The oil hydrolysis agent obtained in Examples 1 and 2 was subjected to an alkali hydrolysis resistance test by the following method. For comparison, with respect to the oil agent obtained from Comparative Example 1, [co mo 143], isopropyl myristate [ekisepallPM, manufactured by Kao Corporation], and tri-2-ethylhexanoate Acid glyceride [Nippon Oil & Gas Co., Ltd., TIO] etc. used the same test method to test the alkali hydrolysis resistance. The test results are shown in Table 1. As a method, each oil agent was sampled at each mass and added to 25ml KOH-ethanol solution of each concentration of about 8 (saponification decomposition reaction in a water bath of TC. It is determined that the time when the saponification decomposition rate reaches 100%. And the saponification decomposition rate is determined by (actually measured saponification value / theoretical saponification value) X 1 0 0 was obtained. As shown in Table 1, the saponification conditions of the examples Comparing the comparative products, although it is relatively easy to saponify and decompose, it takes a long time to reach a saponification decomposition rate of 100%. That is, the oil agent of the present invention has excellent resistance to hydrolysis by hydrolysis. (Please read the back first For the matters needing attention, please fill in this page again. Packing. The standard of 11-line paper method is applicable to China National Standard (CNS) A4 (210X29 * 7mm) -18-15200301708 A7 B7 V. Description of the invention (Saponification conditions for oil saponification) End of saponification decomposition time (h) Sampling quantity (g) KOH ethanol-solution concentration (N) Example 1 0.5 1 22 Example 2 0.5 1 20 Comparative example 1 1.5 0.5 0.5 Tetradecanoic acid isopropyl acid 2 0.5 0.5 Three 2-Ethylhexanoic acid glyceride 1.5 1 1.5 Application of lipsticks in Examples 3, 4 and Comparative Examples 2 to 4 Strip lipsticks with the composition shown in Table 2 were prepared by the following method, and the breaking strength and feeling of use were evaluated. Evaluation The results are shown in Table 2. τρ; (Please read the precautions on the back before filling out this page} • Binding and ordering [Manufacturing method of strip lipstick]

Step 1 · Each of the raw materials (1) to (7) in Table 2 is heated and dissolved with 120 ~ i3 (rC. Step 2: The raw material obtained in step 1 is added to (8) and uniformly mixed. Step 3: Step 2 After defoaming the obtained material, the raw materials (9) and (100) are added and mixed uniformly. Step 4: The obtained liquid obtained in step 3 is poured into a mold for lipstick formation, and then cooled and formed to obtain a strip-shaped lipstick. In Table 2, the structure of diglyceryl monoisostearate (5) and glyceryl trioctanoate (6) is as follows. The paper size applies to the Chinese National Standard (CNS) Λ4 specification (210X297)- 19- Wisdom / i Bureau of the Ministry of Line Economy: 200301708 A7 B7 -16 printed by S Industrial Consumer Cooperative Co., Ltd. 5. Description of the invention () (5) Monoisostearyl diglyceride CH2OCO (CH3) mCH (CH2) nCH.

CHOH I ch2och2 I CHOH I CH〇OH CH; [where m and n 値 are m + n = 14] (6) glyceryl tricaprylate (please read the precautions on the back before filling this page) CH2CH3 CH2OCOCH (CH2) 3CH3 ch2ch3

I CHOCOCH (CH2) 3CH3 ch2ch3

I CH2OCOCH (CH2) 3CH3 line [striped lipstick evaluation method] 1. Fracture strength evaluation: LeometerNRM-2002J (Ministry of Industry and Economics Zhicongcai / 1 Bureau of negative work ^ fee cooperation stove printed ^ C shares) company system) For measurement, those with sufficient shape retention were evaluated in three stages of 0, △, and X. 2. Evaluation of the feeling of use: 20 female evaluators were used as the target for the use test, and the extension and smoothness during the application were evaluated. The evaluation is based on a good extension and smooth coating. The number of judges is 0, △, and X. The paper is sufficient to evaluate the suitability of the paper. The Chinese national standard (CNS) A4 specification (210X 297 mm) -20- 200301708 A7 B7 Ϊ7 --- 5. Description of the invention () The evaluation criteria are shown in Table 3. The evaluation results of the lipstick obtained in Example 3 or 4 show that the strip lipstick of the oil agent containing the ester compound of the present invention prepared in Example 1 or Example 2 has high breaking strength, excellent shape retention, and is applied. In the case of stretching, smoothness, the feeling of use is good, and no discoloration or sweating is caused, and the molding state is also good. In this case, in the case where the oil agent of the present invention is not used, as shown in Comparative Examples 2 to 4, any one of the breaking strengths is not sufficient, and the use feeling is not satisfactory. (Please read the precautions on the back before filling this page) -Installation, -Ministry of Economy, Economics and Welfare / 1 Bureau: Only printed by the Consumers' Cooperative, the paper size is applicable to China National Standard (CNS) Α4 size (210 × 297) %) -21-200301708

AB 18 V. Description of the invention () Table 2 (mass%) Wisdom and Finance 1 Bureau of the Ministry of Economics: only labor and expenses cooperatives printed materials and evaluation items 1 g cases Comparative Example 3 4 2 3 4 (1) Microcrystalline wax 12 12 12 12 12 (2) Glyceryl triisostearate [prepared product of Example 1] 52 (3) Diglyceryl triisostearate [prepared product of Example 2] 52 (4) Diisostearate Glyceride [Comparative Example 1 Preparation] 52 (5) Diglyceryl monoisostearate 52 (6) Glyceryl tricaprylate 52 (7) Polybutene 10 10 10 10 10 (8) Tetradecanol octyl Dodecyl ester 20 20 20 20 20 (9) Colored pigment 5 5 5 5 5 (10) Fragrance 1 1 1 1 1 Breaking strength 〇〇〇Δ X Feeling 0 〇Δ X — (Please read the note on the back first (Fill in this page again)

This paper size is applicable to China National Standard Year (CNS) A4 size (210x 297 mm) -22-200301708 A7 B7 V. Description of the invention () Table 3 Ύ9 Evaluation of lipstick lipstick breaking strength evaluation Use evaluation 0 Good 1 or more △ Ordinary 5 to 14 people X Difficulty in molding and less than 4 people — The breaking strength is too low to evaluate the oil agent containing the specific ester compound of the present invention as described above, and it is more difficult to hydrolyze compared with the conventional ester oil agent, above 40 ° C Good stability under high temperature or long time. Therefore, products containing general ester compounds, such as skin external preparations or cosmetics, can be used without limiting the amount of ester compounds used, and can be used for applications that have not been able to be used with acid hydrolysis resistance or alkali hydrolysis resistance until now. , Can expand the use of ester compounds. In addition, the skin external preparation or cosmetics using the oil agent of the present invention can improve the storage stability of the oily substance contained therein, improve the use feeling on the skin, improve water vapor permeability, improve color, improve shape retention, and pigment. Improved dispersion. In addition, since the oil agent of the present invention has no problems such as skin irritation, safety, etc., it can be safely used for any product, and a product with high reliability can be obtained. (Please read the precautions on the reverse side before filling out this page) -Installation, \ = v > Printed by the Ministry of Economic Affairs, Congcai / i Bureau: Printed by Cooperative Co., Ltd. ^ This paper size applies Chinese National Standard (CNS) Α4 specifications ( 210X 297 public holiday) -23-

Claims (1)

200301708 CHCOOH A8 B8 C8 D8 6. Application scope of patent 1 1. An oil agent characterized by containing an ester compound composed of a branched fatty acid represented by chemical formula (I) and a mono- or polyhydric alcohol, R i-ch2 r2 -ch (ch3) [wherein l and R2 represent a hydrocarbon group]. 2. An oil agent characterized by containing a fatty acid other than the branched fatty acid represented by the general formula (I) in the first patent application scope and the branched fatty acid represented by the general formula (I) in the first patent application scope And ester compounds composed of polyhydric alcohols. 3. The oil agent according to item 2 of the patent application, wherein the fatty acid other than the branched fatty acid shown in the general formula (I) of the item 1 of the patent application is one or more selected from linear saturated or unsaturated fatty acids and branched chains Group of saturated or unsaturated fatty acids and cyclic saturated or unsaturated fatty acids. 4. For the oil agent of any one of the items 1 to 3 of the scope of the patent application, in which one or both of Ri and R2 of the branched fatty acid shown in the general formula (I) of the scope of the patent application is one or both Branched hydrocarbyl. 5. The oil agent according to any one of items 1 to 4 in the scope of patent application, wherein in the general formula (I), Ri and R2 may be the same or different from each other, and the linear or branched carbon number is 1 to 12. Chain or cyclic saturated or unsaturated hydrocarbon group. 6. The oil agent according to any one of items 1 to 5 in the scope of patent application, wherein in the general formula (I), 1 ^ is (CH3) 3CCH2CH (ch3) ch2 m, and R2 is the size of the paper and clothing. Applicable to China National Rubbing Standard (CNS) A4 Specification (210X297 Male Dust --------- ^ ------ II ------ Silk (Please read the precautions on the back before filling this page) Economy Printed by the Consumer Property Cooperation Bureau of the Ministry of Intellectual Property Bureau 24 200301708 A8 B8 C8 D8 Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs 6. Application for patent scope 2 (ch3) 3cch2 basis. 7. If the scope of patent application is 1st to 6th The oil agent of any one of clauses, wherein the monohydric alcohol is one or more members selected from the group consisting of isooctanol, isododecanol, isopalmityl alcohol, isostearyl alcohol, isicosanol, isohexacosanol, and Polyol is one or more selected from glycerol, diglycerol, diglycerol, polyglycerol, ethylene glycol, diethylene glycol, 1,3-butanediol, 3-methyl-1,3-butanediol Alcohol, propylene glycol, dipropylene glycol, tripropylene glycol, polyethylene glycol, hexanediol, erythritol, pentaerythritol, dipentaerythritol, trimethylolpropane, ditrimethanolpropane, sorbitan Alcohol, ethyl cellosolve, butyl cellosolve, ethylcarbitol and butylcarbitol. 8. If you apply for an oil agent in any one of items 1 to 7, Wherein the hydroxyl value of the oil agent is fluorene in the range of 0 to 400. 9. For the oil agent in the scope of application for item 8, the hydroxyl value of the oil agent is 値 in the range of 0 to 80. 1 0.1 -An oil agent characterized by containing an acid-resistant hydrolyzable ester compound as described in any one of claims 1 to 9. 1 1. An oil agent characterized by containing an alkali-hydrolyzing resistant agent such as Those who apply for an ester compound according to any one of the scope of patents Nos. 1 to 9. 1 2. An external skin preparation, which is characterized by containing an oil agent such as any of the scope of Nos. 1 to 9 of the patent scope 1 3. A skin external preparation such as those in the scope of patent application No. 12 which further contains Vaseline. 1 4. A cosmetic product characterized by containing any one of the scope of patent applications in No. 1 to 9 Oiler. ^-(Please read the notes on the back before filling this page), ^ 1 Silk paper size is applicable to China Furniture Standard (CNS) A4 Specification (210 × 297 mm) -25- 200301708 A8 B8 C8 D8 VI. Application for Patent Scope 3 15. If you apply for a cosmetic product under the scope of patent No. 14, it also contains 蠘. 16. If you apply for a patent Cosmetics in the scope of item I4 or item 15, wherein the cosmetics are in the form of lipstick, bright lipstick, lipstick, eye shadow, blush, lotion or lotion. 1 7.-Such as the scope of application for patents from item 1 to item 1 The use of the oil agent according to any one of 9 items, characterized in that it is used for the preparation of a skin external preparation. 18 · —The use of an oil agent according to any one of claims 1 to 9 of the scope of patent application, characterized in that it is used in the manufacture of cosmetics. (Please read the precautions on the back before filling this page) Printed by the Bone Cooperative of the Wisdom and Welfare Bureau of the Ministry of Economic Affairs -26- Ug furniture rate (CNS) A4iJ ^ (21QX297 public envy) 200301708 ( A), the designated representative of this case is: no (two), the representative symbols of the representative diagram of the brief description: no (three), if there is a chemical formula in this case, please reveal the chemical formula that can best show the characteristics of the invention: none-3-