Oil

Abstract

An object of the present invention is to provide a novel oil agent having excellent emulsion stability. 【Means for solving the problem】The means for solving the problem is an oil agent containing a fatty acid lower alkyl ester and a fatty acid glyceride, wherein the fatty acid lower alkyl ester and the fatty acid glyceride have a fatty acid composition derived from natural fats and oils, the content of the fatty acid lower alkyl ester in the oil agent is 40% by mass or more and 80% by mass or less, the content of the fatty acid glyceride in the oil agent is 3% by mass or more and 15% by mass or less as fatty acid triglyceride, 3% by mass or more and 25% by mass or less as fatty acid diglyceride, 8% by mass or more and 20% by mass or less as fatty acid monoglyceride, and it is an oil agent.

Description

Technical Field

[0001] The present invention relates to an oil agent containing fatty acid lower alkyl esters and fatty acid glycerides.

Background Art

[0002] Conventionally, oil agents mainly composed of fatty acid esters and fatty acid glycerides have been used in a wide range of fields such as cosmetics, detergents, foods, and industrial applications. Improvements have been made from the viewpoints of emulsifying properties, stability, and further moisture retention.

[0003] Patent Document 1 describes a detergent composition containing an oil agent that is a condensation product of an ester of diglycerin and a branched-chain monocarboxylic acid having 16 to 18 carbon atoms and a dicarboxylic acid having 6 to 10 carbon atoms. The oil agent has excellent water retention and emollient properties, is safe for the skin, and also functions as an emulsifying and dispersing aid, greatly contributing to the stability of the formulation. It is also described that it does not affect the foaming property of the surfactant.

[0004] Patent Document 2 describes an emulsified composition using a vegetable liquid oil as an oil component, in which an emulsifier and an aqueous phase component are blended. Further, as the vegetable liquid oil, at least three or more different types of hydrocarbon oils, ester oils, and triglyceride oils are blended. The emulsified composition is described as having excellent usability for the skin such as skin affinity, non-greasiness, and moist feeling, and also having excellent storage stability.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

[0006] Given the prior art described above, the object of the present invention is to provide a novel oil formulation with excellent emulsification stability. [Means for solving the problem]

[0007] The present invention, which solves the above problems, is as follows [1] to [7].

[0008] [1] An oily preparation comprising a lower alkyl ester of fatty acid and a fatty acid glyceride, The aforementioned lower alkyl fatty acid ester and the aforementioned fatty acid glyceride have a fatty acid composition derived from natural oils and fats. The amount of lower alkyl fatty acid ester in the oil is 40% by mass or more and 80% by mass or less. The amount of fatty acid glyceride contained in the aforementioned oil is 3% to 15% by mass as fatty acid triglycerides 3% to 25% by mass as fatty acid diglycerides, As fatty acid monoglycerides, 8% by mass or more and 20% by mass or less, It is an oil-based product.

[0009] [2] The oily agent according to [1], wherein the fatty acid lower alkyl ester and / or the fatty acid glyceride are enzymatically transesterified.

[0010] [3] The oily agent according to [1] or [2], wherein the total mass of linoleic acid and linolenic acid when the total mass of fatty acids contained in the fatty acid lower alkyl ester and the fatty acid glyceride is taken as 1 is 0.25 or less.

[0011] [4] The oily agent according to any one of [1] to [3], wherein the lower alkyl group of the fatty acid lower alkyl ester is an ethyl group.

[0012] [5] An oil for cosmetic use and / or for cleaning agents, as described in any of [1] to "4".

[0013] A composition containing the oil agent according to any one of [6][1] to [5].

[0014] [7] A method for producing an oil agent containing a fatty acid lower alkyl ester and a fatty acid glyceride, including a reaction step of enzymatically transesterifying natural fats and oils with a lower alkyl alcohol, the oil agent obtained after the reaction step is the fatty acid lower alkyl ester is 40% by mass or more and 80% by mass or less, and the fatty acid glyceride is as fatty acid triglyceride 3% by mass or more and 15% by mass or less, as fatty acid diglyceride 3% by mass or more and 25% by mass or less, as fatty acid monoglyceride 8% by mass or more and 20% by mass or less, A method for producing an oil agent containing.

Advantages of the Invention

[0015] According to the present invention, a novel oil agent excellent in emulsion stability can be obtained.

Modes for Carrying Out the Invention

[0016] Hereinafter, the present invention will be described in detail.

[0017] <Oil agent> In the present invention, the fatty acid lower alkyl ester means a lower alkyl ester compound of a fatty acid. The fatty acid lower alkyl ester in the present invention has a fatty acid composition derived from natural fats and oils. The fatty acid composition derived from natural fats and oils means the fatty acid composition when all the triglycerides of natural fats and oils are hydrolyzed into fatty acids and glycerin.

[0018] In the present invention, the fatty acid glyceride means an ester compound of a fatty acid and glycerin. The ester includes mono, di, and triesters. The fatty acid glyceride in the present invention has a fatty acid composition derived from natural fats and oils.

[0019] The fatty acid lower alkyl ester and fatty acid glyceride in the present invention are both characterized by having the same fatty acid composition of natural oils and fats. Here, since the fatty acid lower alkyl esters and fatty acid glycerides obtained from a plurality of different fatty acid sources do not have the same fatty acid composition of natural oils and fats, they are different from the fatty acid lower alkyl esters and fatty acid glycerides having the same fatty acid composition of natural oils and fats.

[0020] The fatty acid lower alkyl ester and fatty acid glyceride in the present invention may be obtained by enzymatic transesterification, or may be fatty acid lower alkyl esters and fatty acid triglycerides separately recovered by treating the same natural oil and fat.

[0021] The enzymatic transesterification reaction of reacting one natural oil and fat with a lower alkyl alcohol uses one natural oil and fat as a raw material, so there is no need to procure and mix a plurality of raw materials. As a result, the raw material procurement process is simplified and the procurement cost can be reduced. In addition, by performing the enzymatic transesterification reaction of reacting one natural oil and fat with a lower alkyl alcohol, fatty acid lower alkyl esters and fatty acid glycerides can be obtained simultaneously. In this step, since there is no need for a step of mixing different raw material components or a plurality of stepwise reaction steps, the manufacturing process can be simplified and the manufacturing time and energy cost can be reduced. Furthermore, by producing the fatty acid lower alkyl ester and fatty acid glyceride in the present invention using one natural oil and fat, the amount of by-products can be minimized. As a result, the burden of the post-treatment process (for example, liquid separation operation and filtration) can be reduced, the cost required for waste treatment can be reduced, and the environmental load in the entire manufacturing process can be reduced.

[0022] The oil agent of the present invention is produced by the method described in the <Method for Producing Oil Agent> described later.

[0023] In the present invention, the mass content of the fatty acid lower alkyl ester in the oil agent is 40% by mass or more and 80% by mass or less.

[0024] In the present invention, the lower limit of the fatty acid lower alkyl ester content in the oil is preferably 42% by mass or more, more preferably 44% by mass or more, more preferably 46% by mass or more, more preferably 48% by mass or more, more preferably 50% by mass or more, and even more preferably 52% by mass or more.

[0025] In the present invention, the upper limit of the fatty acid lower alkyl ester content in the oil is preferably 77% by mass or less, more preferably 74% by mass or less, more preferably 73% by mass or less, more preferably 70% by mass or less, more preferably 67% by mass or less, more preferably 63% by mass or less, and even more preferably less than 63% by mass. In the present invention, if the fatty acid lower alkyl ester content in the oil is less than 63% by mass, the oil becomes superior in terms of emulsification stability.

[0026] In the present invention, the amount of fatty acid glycerides in the oil is 3% by mass or more and 15% by mass or less as fatty acid triglycerides.

[0027] In the present invention, the lower limit of the fatty acid triglyceride content in the oil is preferably 3.5% by mass or more, more preferably 4% by mass or more, more preferably 4.5% by mass or more, more preferably 5% by mass or more, more preferably 5.5% by mass or more, and even more preferably 6% by mass or more. In the present invention, if the fatty acid triglyceride content in the oil is 6% by mass or more, the oil becomes superior in terms of emulsification stability.

[0028] In the present invention, the upper limit of the fatty acid triglyceride content in the oil is preferably 14% by mass or less, more preferably 13% by mass or less, more preferably 12% by mass or less, more preferably 11% by mass or less, more preferably 10% by mass or less, more preferably 9% by mass or less, and even more preferably 8% by mass or less.

[0029] In the present invention, the amount of fatty acid glycerides in the oil is 3% by mass or more and 25% by mass or less as fatty acid diglycerides.

[0030] In the present invention, the lower limit of the fatty acid diglyceride content in the oil is preferably 5% by mass or more, more preferably 7% by mass or more, more preferably 9% by mass or more, more preferably 11% by mass or more, more preferably 13% by mass or more, more preferably 15% by mass or more, and even more preferably 16% by mass or more.

[0031] In the present invention, the upper limit of the fatty acid diglyceride content in the oil is preferably 24% by mass or less, more preferably 23% by mass or less, more preferably 22% by mass or less, more preferably 21% by mass or less, more preferably 20% by mass or less, and even more preferably 19% by mass or less.

[0032] In the present invention, the amount of fatty acid glycerides in the oil is 8% by mass or more and 20% by mass or less as fatty acid monoglycerides.

[0033] In the present invention, the lower limit of the fatty acid monoglyceride content in the oil is preferably 8.5% by mass or more, more preferably 9% by mass or more, more preferably 10% by mass or more, more preferably 11% by mass or more, more preferably 11.5% by mass or more, more preferably 12.5% ​​by mass or more, and even more preferably 14% by mass or more.

[0034] In the present invention, the upper limit of the fatty acid monoglyceride content in the oil is preferably 19.5% by mass or less, more preferably 19% by mass or less, more preferably 18.5% by mass or less, more preferably 18% by mass or less, more preferably 17.5% by mass or less, more preferably 17% by mass or less, and even more preferably 16% by mass or less.

[0035] The oil formulation of the present invention, having the above configuration, has been confirmed to be an oil formulation with excellent emulsification stability. Therefore, the oil formulation of the present invention can maintain a uniform emulsified state for a long period of time without the need to add an emulsifier.

[0036] In the present invention, the mass ratio of fatty acid lower alkyl ester to fatty acid glyceride in the oil is preferably in the range of 1:0.15 to 1:1.5, more preferably 1:0.2 to 1:1.3, more preferably 1:0.4 to 1:1.2, more preferably 1:0.5 to 1:1, more preferably 1:0.6 to 1:1, more preferably 1:0.61 to 1:1, and even more preferably 1:0.62 to 1:1. In the present invention, when the mass ratio of fatty acid lower alkyl ester to fatty acid glyceride in the oil is within the range of 1:0.62 to 1:1, the oil becomes superior in terms of emulsification stability.

[0037] In the present invention, the mass ratio of fatty acid lower alkyl ester to fatty acid triglyceride in the oil is preferably within the range of 1:0.03 to 1:0.4, more preferably 1:0.05 to 1:0.35, more preferably 1:0.06 to 1:0.3, more preferably 1:0.065 to 1:0.25, more preferably 1:0.07 to 1:0.2, and even more preferably within the range of 1:0.095 to 1:0.15. In the present invention, when the mass ratio of fatty acid lower alkyl ester to fatty acid triglyceride in the oil is within the range of 1:0.095 to 1:0.15, the oil becomes superior in terms of emulsification stability.

[0038] In the present invention, the mass ratio of fatty acid lower alkyl ester to fatty acid diglyceride in the oil is preferably in the range of 1:0.03 to 1:0.65, more preferably 1:0.09 to 1:0.6, more preferably 1:0.15 to 1:0.55, more preferably 1:0.18 to 1:0.5, more preferably 1:0.2 to 1:0.45, and even more preferably 1:0.25 to 1:0.4.

[0039] In the present invention, the mass ratio of fatty acid lower alkyl ester to fatty acid monoglyceride in the oil is preferably within the range of 1:0.1 to 1:0.5, more preferably 1:0.12 to 1:0.46, more preferably 1:0.15 to 1:0.42, more preferably 1:0.18 to 1:0.38, more preferably 1:0.2 to 1:0.35, and even more preferably within the range of 1:0.25 to 1:0.35. In the present invention, when the mass ratio of fatty acid lower alkyl ester to fatty acid monoglyceride in the oil formulation is within the range of 1:0.25 to 1:0.35, the oil formulation exhibits superior emulsification stability.

[0040] In the present invention, the mass ratio of fatty acid triglycerides to fatty acid diglycerides in the oil is preferably within the range of 1:0.15 to 1:8.5, more preferably 1:0.45 to 1:7.2, more preferably 1:0.75 to 1:6, more preferably 1:1.1 to 1:5.5, more preferably 1:1.3 to 1:5, more preferably 1:1.5 to 1:3.5, more preferably 1:1.5 to 1:3, and even more preferably within the range of 1:1.5 to 1:2.9. In the present invention, when the mass ratio of fatty acid triglycerides to fatty acid diglycerides in the oil is within the range of 1:1.5 to 1:2.9, the oil becomes superior in terms of emulsification stability.

[0041] In the present invention, the mass ratio of fatty acid triglycerides to fatty acid monoglycerides in the oil is preferably within the range of 1:0.5 to 1:7, more preferably 1:0.75 to 1:6, more preferably 1:0.8 to 1:5, more preferably 1:0.9 to 1:4.5, more preferably 1:1 to 1:4, more preferably 1:1 to 1:3, and even more preferably 1:1 to 1:2.5. In the present invention, when the mass ratio of fatty acid triglycerides to fatty acid monoglycerides in the oil formulation is within the range of 1:1 to 1:2.5, the oil formulation exhibits superior emulsification stability.

[0042] In the present invention, the mass ratio of fatty acid diglycerides to fatty acid monoglycerides in the oil is preferably in the range of 1:0.3 to 1:7, more preferably 1:0.35 to 1:5, more preferably 1:0.4 to 1:3, more preferably 1:0.45 to 1:2, more preferably 1:0.5 to 1:1.1, and even more preferably 1:0.7 to 1:1.

[0043] The oil formulation of the present invention, having the above configuration, has been confirmed to be an oil formulation with excellent emulsification stability. Therefore, the oil formulation of the present invention can maintain a uniform emulsified state for a long period of time without the need to add an emulsifier.

[0044] In the present invention, the lower alkyl is preferably a C1-C5 alkyl, more preferably a C1-C3 alkyl, and even more preferably a C2 alkyl (ethyl).

[0045] In the present invention, examples of fatty acids include acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, behenic acid, erucic acid, ricinoleic acid, and the like. Alternatively, a blend of fatty acids derived from natural oils containing these fatty acids may also be used.

[0046] In this invention, natural oils and fats are used as the oils and fats. Examples of natural oils and fats include animal-derived natural oils and fat

[0047] Examples of natural oils derived from plants include palm oil, palm kernel oil, soybean oil, rapeseed oil, high-oleic rapeseed oil, sunflower oil, high-oleic sunflower oil, corn oil, coconut oil, palm olein oil, palm stearin oil, castor oil, peach kernel oil, sesame oil, olive oil, almond oil, avocado oil, jojoba oil, rice bran oil, safflower oil, high-oleic safflower oil, rice bran oil, cottonseed oil, linseed oil, perilla oil, grapeseed oil, chia seed oil, pumpkin seed oil, argan oil, walnut oil, macadamia nut oil, and shea butter. Modified oils obtained by fractionation, hydrogenation, transesterification, etc., and mixtures thereof may also be included. Both refined and unrefined versions of these oils can be used, but refined versions are preferred. Furthermore, in the present invention, it is preferable to use one or more selected from the above oils and fats.

[0048] In the present invention, it is preferable that the natural oil is one or more selected from palm oil, palm kernel oil, soybean oil, rapeseed oil, high oleic rapeseed oil, and sunflower oil.

[0049] Furthermore, the natural oils and fats in the present invention are not particularly limited by their fatty acid composition, but it is preferable that they contain a large amount of oleic acid. The lower limit of the mass percentage of oleic acid in the natural oils and fats relative to the total fatty acid composition mass is preferably 10% by mass or more, more preferably 35% by mass or more, more preferably 40% by mass or more, more preferably 50% by mass or more, and even more preferably 60% by mass or more.

[0050] In the present invention, it is preferable that the total mass of linoleic acid and linolenic acid, when the total mass of fatty acids contained in the fatty acid lower alkyl ester and fatty acid glyceride in the oil is set to 1, is 0.25 or less. By using the above configuration, the oxidative deterioration odor after one week of storage can be further suppressed.

[0051] In the present invention, the upper limit of the total content mass of linoleic acid and linolenic acid, when the total mass of fatty acids contained in the fatty acid lower alkyl ester and fatty acid glyceride in the oil is set to 1, is preferably 0.2 or less, more preferably 0.15 or less, more preferably 0.11 or less, and even more preferably 0.1 or less.

[0052] In the present invention, there is no particularly preferred lower limit for the total content of linoleic acid and linolenic acid when the total mass of fatty acids contained in the fatty acid lower alkyl ester and fatty acid glyceride in the oil is set to 1, but it may be 0.01 or more, or 0.03 or more.

[0053] In the present invention, the total mass of saturated fatty acids with C16 or higher, more preferably saturated fatty acids with C16 or higher and C22 or lower, when the total mass of fatty acids contained in the fatty acid alkyl ester is set to 1, is preferably 0.6 or less, more preferably 0.5 or less, more preferably 0.4 or less, and even more preferably 0.3 or less. The above configuration makes it possible to further suppress crystal precipitation during storage.

[0054] In the present invention, the glycerin content in the oil is preferably 5% by mass or less, more preferably 4.5% by mass or less, more preferably 4% by mass or less, more preferably 3.5% by mass or less, more preferably 3% by mass or less, more preferably 2.5% by mass or less, more preferably 2% by mass or less, more preferably 1.5% by mass or less, and more preferably less than 1% by mass.

[0055] The oil formulation of the present invention has excellent self-emulsifying properties. Self-emulsifying properties refer to the ability of the oil formulation itself to form a uniform emulsion in water without the need to add an emulsifier from an external source once added to the water. Due to these excellent self-emulsifying properties, the oil formulation of the present invention can be used as an oil formulation for cosmetics and an oil formulation for detergents. The oil formulation of the present invention eliminates the need for additional emulsifiers when manufacturing products such as cosmetics and detergents, thus simplifying formulation.

[0056] In this invention, cosmetics are classified into hair cosmetics, skin cosmetics, finishing cosmetics, perfumes / eau de colognes, and others (according to the Japan Fair Trade Council for Cosmetics website: https: / / www.cftc.jp / index.html), and are used on the skin, hair, etc. There are also quasi-drugs (so-called medicated cosmetics) which are cosmetics that contain active ingredients to achieve specific effects.

[0057] The base of cosmetics (basic components of cosmetics) consists of aqueous components, oily components, powdery components, and surfactants. In this specification, "oil for cosmetics" refers to "oily components" as a base for cosmetics. Oily components are oil-soluble and not water-soluble on their own.

[0058] In the present invention, the cleaning agent can include surfactants, disinfectants, solvents, chlorine-based oxidizing agents, oxygen-based oxidizing agents, ethanol preparations, chelating agents, abrasives, enzymes, soap, and the like. Among these, the inclusion of soap is preferred.

[0059] Furthermore, in the present invention, a composition containing the aforementioned oil agent can be obtained by mixing it with any other component.

[0060] <Manufacturing method for oil-based formulations> The oil formulation of the present invention can be produced by a manufacturing method that includes a transesterification reaction of natural oils and fats with lower alkyl alcohols. This transesterification reaction can be carried out by combining known methods.

[0061] In the present invention, a natural oil and fat can be mixed with a lower alkyl alcohol, and a transesterification reaction can be carried out using an enzyme or a basic compound as a catalyst.

[0062] In the present invention, the enzyme used as a catalyst is not particularly limited as long as it has the property of catalyzing the esterification or transesterification reaction of fatty acids. For example, lipases and esterases can be used.

[0063] In the present invention, lipases such as those derived from Thermomyces lanuginosus (e.g., Lipozyme TL IM), Candida antarctica (e.g., CALB), and Rhizomucor miehei (e.g., Lipozyme RM IM) can be used.

[0064] When producing the oil formulation of the present invention by enzymatic transesterification, the reaction temperature is preferably 40°C to 60°C.

[0065] When producing the oil formulation of the present invention by enzymatic transesterification, the lower limit of the reaction temperature is more preferably 42°C or higher, more preferably 44°C or higher, and even more preferably 45°C or higher.

[0066] When producing the oil formulation of the present invention by enzymatic transesterification, the upper limit of the reaction temperature is more preferably 58°C or lower, more preferably 56°C or lower, and even more preferably 55°C or lower.

[0067] Furthermore, when producing the oil formulation of the present invention by enzymatic transesterification, the reaction time is preferably 60 minutes or more and 360 minutes or less.

[0068] When producing the oil formulation of the present invention by enzymatic transesterification, the lower limit of the reaction time is more preferably 60 minutes or more, more preferably 70 minutes or more, more preferably 80 minutes or more, and even more preferably 90 minutes or more.

[0069] When producing the oil formulation of the present invention by enzymatic transesterification, the upper limit of the reaction time is more preferably 360 minutes or less, more preferably 330 minutes or less, more preferably 300 minutes or less, and even more preferably 270 minutes or less.

[0070] Enzymatic transesterification reactions can reduce the environmental impact compared to reactions using base catalysts.

[0071] When producing the oil formulation of the present invention using a base catalyst, the reaction temperature is preferably 20°C to 40°C.

[0072] Furthermore, when producing the oil formulation of the present invention using a base catalyst, the reaction time is preferably 10 minutes or more and 300 minutes or less.

[0073] Post-transesterification treatment can also be carried out as appropriate using conventional methods.

[0074] The recovered oil phase is vacuum-dried at a temperature between 60°C and 100°C to remove lower alcohols. The oil may also be further refined as needed. [Examples]

[0075] The present invention will be described in more detail below with reference to examples, but the scope of the present invention is not limited in any way to the descriptions in these examples.

[0076] [Example 1] High-oleic sunflower oil and ethanol (99.5%) were measured in a 1:3 molar ratio into a 500 mL round-bottom flask and stirred to prepare a homogeneous mixture. To this mixture, 8 wt% of enzyme (Lipozyme TL IM, manufactured by Novozymes) relative to the high-oleic sunflower oil was added, and the flask was sealed tightly. The ethanolylation reaction was carried out in a 50°C water bath for 240 minutes with stirring. The solution after the reaction was filtered and purified to obtain the oil formulation of the present invention. The obtained oil was subjected to gas chromatography (GC) analysis to determine the content ratio of fatty acid lower alkyl esters and fatty acid glycerides.

[0077] [Example 2]~[Example 6] For Examples 2 to 6, oil formulations were obtained using each raw material oil in the same manner as in Example 1.

[0078] [Comparative Example 1] High-oleic sunflower oil was prepared as the oiling agent.

[0079] [Comparative Example 2] 200 g of high-oleic sunflower oil was weighed into a 500 mL round-bottom flask. A solution of 2 g of potassium hydroxide dissolved in 62.75 g of ethanol (99.5%) was added to the flask, and the flask was sealed tightly. The flask was stirred in a 30°C water bath and the ethanolylesis reaction was carried out for 150 minutes. The resulting solution was transferred to a separatory funnel, and the aqueous phase was discarded after separation with 100 g of water. Another 100 g of water was added to the remaining oil phase, and the aqueous phase was discarded after separation. The remaining oil phase was transferred to a 300 mL round-bottom flask and vacuum-dried for 30 minutes while stirring in an 80°C water bath. Subsequently, the mixture was filtered and purified to obtain 185 g of oil (96.8% lower alkyl fatty acid ester).

[0080] [Reference example 1] An oily substance was obtained by mixing 53% by mass of reagent (ethyl oleate, fatty acid lower alkyl ester content 99.8% by mass), 32% by mass of reagent (monoolein, fatty acid monoglyceride content 52.1% by mass), and 15% by mass of reagent (glycerol dioleate, fatty acid diglyceride content 54.1%).

[0081] Tables 1 and 2 show the mass content of lower alkyl fatty acid esters and fatty acid glycerides in the oils in Examples 1-6, Comparative Examples 1-2, and Reference Example 1.

[0082] The self-emulsifying properties of the oils obtained in Examples 1-6, Comparative Examples 1-2, and Reference Example 1 were evaluated by the following method.

[0083] <Testing Method> 0.015 g of oil was added to a solution prepared by dissolving 0.020 g of xanthan gum in 4.465 g of water, 0.250 g of glycerin, and 0.250 g of propanediol, and the mixture was vigorously stirred for 1 minute using a vortex mixer. The stirred solution was then placed at 40°C and stored for 7 days. After storage, the appearance of the solution was observed, and the oil was evaluated according to the following evaluation criteria.

[0084] <Evaluation Criteria> ○: Emulsification is maintained. △: Although there is a slight separation of water and oil, the emulsification is maintained. ×: Emulsification is not maintained, and the water and oil have separated.

[0085] Furthermore, six evaluators specializing in oil development evaluated the initial aroma and the oxidative degradation odor after storing the oil formulations obtained in Examples 1-6, Comparative Examples 1-2, and Reference Example 1 at 50°C for 7 days. <Evaluation Criteria> ◎: No change 〇: Slightly detects an oxidative, deteriorated smell. △: Slightly detectable odor of oxidation and deterioration. ×: A strong odor of oxidation and deterioration is detected.

[0086] <Analysis method> (i) Constituent fatty acids Analysis was performed using the standard oil and fat analysis method (2.4.1.2-2013 Methyl esterification method (boron trifluoride-methanol method)) and 2.4.2.3-2013 Fatty acid composition (capillary gas chromatography method). (ii) Content ratio of lower alkyl esters and fatty acid glycerides The proportion of lower alkyl esters and fatty acid glycerides in the oil was calculated using a gas chromatograph. Specifically, approximately 100 mg of the oil was dissolved in 10 ml of hexane and introduced into the gas chromatograph. The GC measurement conditions were as follows:

[0087] Equipment: GC-2010 (manufactured by Shimadzu Corporation) Column: DB-1 1m × 0.25mm i.d. df = 0.25μm Temperature conditions: 50℃ (1 minute) ~ 10℃ / min ~ 320℃ (8 minutes) Carrier gas: Helium Constant linear velocity: 28.8cm / sec Split ratio: 100

[0088] The results are shown in Tables 1 and 2. Here, the value of "Linoleic acid + Linolenic acid" in Tables 1 and 2 represents the total amount of linoleic acid and linolenic acid when the total mass of fatty acids is set to 1.

[0089] [Table 1]

[0090] [Table 2]

[0091] [Consideration] The oil formulations in Examples 1-6 exhibited self-emulsifying properties because the fatty acid lower alkyl esters and fatty acid glycerides were derived from the same natural oils and fats, and because the fatty acid lower alkyl esters and fatty acid glycerides had specific compositions. The oil formulations in Examples 1-6 maintained their emulsified state even after 7 days of storage, demonstrating excellent emulsion stability. Furthermore, the oil formulations in Examples 1-3 showed even greater emulsion stability compared to Examples 4-6.

[0092] The oil in Comparative Example 1 had not undergone transesterification and contained a large amount of fatty acid triglycerides. The composition of the fatty acid lower alkyl ester and fatty acid glycerides differed from that of the Examples, and it did not exhibit self-emulsifying properties. Similarly, in Comparative Example 2, almost all of the high-oleic sunflower oil was replaced with fatty acid lower alkyl esters. The composition of the fatty acid lower alkyl ester and fatty acid glycerides differed from that of the Examples, and it did not exhibit self-emulsifying properties.

[0093] The oil formulation in Reference Example 1 was prepared by simply mixing several different oil components. Therefore, it did not exhibit self-emulsifying properties.

[0094] Furthermore, the oils of Examples 1-3 and 6, in which the total mass of linoleic acid and linolenic acid when the total mass of fatty acids contained in the fatty acid lower alkyl ester and fatty acid glyceride is set to 1, was 0.25 or less, exhibited excellent oxidative stability. [Industrial applicability]

[0095] Because the oil-based formulation of the present invention has excellent emulsification stability, it can be widely used in the cosmetics, detergent, and food industries, among others.

Claims

1. An oily preparation containing a lower alkyl ester of fatty acid and a fatty acid glyceride, The aforementioned lower alkyl fatty acid ester and the aforementioned fatty acid glyceride have a fatty acid composition derived from natural oils and fats. The amount of lower alkyl ester fatty acids in the oil is 40% by mass or more and 80% by mass or less. The amount of fatty acid glyceride contained in the aforementioned oil is 3% to 15% by mass as fatty acid triglycerides 3% to 25% by mass as fatty acid diglycerides As fatty acid monoglycerides, 8% by mass or more and 20% by mass or less, It is an oil-based product.

2. The oily agent according to claim 1, wherein the fatty acid lower alkyl ester and / or the fatty acid glyceride are enzymatically transesterified.

3. The oily agent according to claim 1 or 2, wherein the total mass of linoleic acid and linolenic acid, when the total mass of fatty acids contained in the fatty acid lower alkyl ester and the fatty acid glyceride is taken as 1, is 0.25 or less.

4. The oily agent according to claim 1 or 2, wherein the lower alkyl group of the fatty acid lower alkyl ester is an ethyl group.

5. The oily agent according to claim 1 or 2, which is an oily agent for cosmetics and / or an oily agent for cleaning agents.

6. A composition comprising the oil agent described in claim 1.

7. A method for producing an oil containing a lower alkyl ester of fatty acid and a fatty acid glyceride, The reaction step involves enzymatically transesterifying natural oils and fats with lower alkyl alcohols. The oil obtained after the reaction step is The aforementioned fatty acid lower alkyl ester is in an amount of 40% by mass or more and 80% by mass or less, The aforementioned fatty acid glyceride, 3% to 15% by mass as fatty acid triglycerides 3% to 25% by mass as fatty acid diglycerides As fatty acid monoglycerides, 8% by mass or more and 20% by mass or less, A method for manufacturing oils, including

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