JP7053977B1 - How to lower the pour point of fatty acid esters - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method capable of lowering a pour point of a fatty acid ester without using a pour point lowering agent. SOLUTION: The flow point of the obtained fatty acid ester mixture including the step of mixing two or more different fatty acid esters satisfying the following conditions (1) and (2) is set from the flow point of each fatty acid ester before the mixing step. Method of lowering: (1) The difference in the flow points of two or more different fatty acid esters is within 25 ° C, and (2) the total of the ester bonds of two or more different fatty acid esters is 5 or more. [Selection diagram] Fig. 1

Description

The present invention relates to a method of lowering the pour point of a fatty acid ester.

The pour point lowering agent is known to lower the pour point in a lubricating oil composition containing an ester-based base oil and widen the applicable temperature range of the lubricating oil composition (see, for example, Patent Document 1). .. However, in the method of lowering the pour point by adding a pour point lowering agent to the fatty acid ester, the performance other than the pour point may be adversely affected, and the pour point lowering agent reacts with other additives to form sludge. There was a risk of formation, and it was necessary to use different additives depending on the base oil.

Japanese Patent Application Laid-Open No. 2021-20993

An object of the present invention is to provide a method capable of lowering the pour point of a fatty acid ester without using a pour point lowering agent.

As a result of repeated trial and error and diligent research in order to solve the above problems, the present inventors unexpectedly lowered the flow point by mixing fatty acid esters that satisfy specific conditions. We found that it was possible to make it possible, and after repeated diligent research, we completed the present invention.

The present invention relates to the following inventions and the like.
[1] The pour point of the obtained fatty acid ester mixture, which comprises the step of mixing two or more different fatty acid esters satisfying the following conditions (1) and (2), is higher than the pour point of each fatty acid ester before the mixing step. How to descend:
(1) The difference between the pour points of two or more different fatty acid esters is within 25 ° C.
(2) The total number of ester bonds of two or more different fatty acid esters is 5 or more.
[2] The method according to [1], wherein each of two or more different fatty acid esters is contained in an amount of 5% by mass or more based on the total mass of the fatty acid ester mixture.

According to the method of the present invention, the pour point of a fatty acid ester can be lowered without using a pour point lowering agent.

FIG. 1 shows a graph showing the relationship between the mixing ratio of the fatty acid esters C and D used in the examples and the pour point of the mixture of the fatty acid esters C and D.

The present invention sets the pour point of the obtained fatty acid ester mixture from the pour point of each fatty acid ester before the mixing step, which comprises the step of mixing two or more different fatty acid esters satisfying the following conditions (1) and (2). Also provides a way to lower.
(1) The difference in the pour points of two or more different fatty acid esters is within 25 ° C. (2) The total sum of the ester bonds of two or more different fatty acid esters is 5 or more.

In the present invention, the fatty acid ester means an ester of an alcohol and a fatty acid.

The alcohol constituting the ester is, for example, a monohydric alcohol such as methanol, ethanol, normalpropanol, isopropanol, normalbutanol, isobutanol, 2-ethylhexanol, amyl alcohol, phenol; ethylene glycol, diethylene glycol, propylene glycol, neopentyl. Divalent alcohols such as glycol, trihydric alcohols such as glycerin, trimethylolethane and trimethylolpropane, tetrahydric alcohols such as pentaerythritol and diglycerin, pentahydric alcohols and hexahydric alcohols such as dipentaerythritol. Etc., Polyhydric alcohols; or combinations thereof. The molecular weight of these alcohols is preferably about 34 to 300, more preferably about 34 to 260. In the present disclosure, "about" is meant to include ± 2.

The fatty acid constituting the ester may be monovalent or polyvalent, may be saturated or unsaturated, may be linear or branched, and may be cyclic. May be. The number of unsaturated carbon bonds and the number of branches are not particularly limited. Unsaturated carbon bonds are double or triple bonds between carbons. The number of unsaturated carbon bonds is usually about 1 to 21.

Examples of preferred fatty acids are butanoic acid (butyric acid), pentanic acid (valeric acid), hexanoic acid (caproic acid), heptanic acid (enant acid), octanoic acid (capric acid), nonanoic acid (pelargonic acid), decanoic acid (decanoic acid). Capric acid), dodecanoic acid (lauric acid), tetradecanoic acid (myristic acid), pentadecanoic acid (pentadecic acid), hexadecanoic acid (palmitic acid), 9-hexadecenoic acid (palmitoleic acid), heptadecanoic acid (margaric acid), octadecanoic acid. (Stearic acid), cis-9-octadecenoic acid (oleic acid), 11-octadecenoic acid (vacenoic acid), cis, cis-9,12-octadecadienoic acid (linoleic acid), 9,12,15-octadecantrine Acids ((9,12,15) -linolenic acid), 6,9,12-octadecatorienic acid ((6,9,12) -linolenic acid), 9,11,13-octadecatriolic acid (eleo) Steeric acid), Eikosanoic acid (arachidic acid), 8,11-eikosadienoic acid, 5,8,11-eikosatrienic acid (mead acid), 5,8,11-eikosatetraenoic acid (arachidonic acid), docosan Acid (bechenic acid), tetracosanoic acid (lignoseric acid), cis-15-tetracosanoic acid (nervonic acid), hexacosanoic acid (serotinic acid), octacosanoic acid (montanoic acid), triacanthic acid (melicic acid), etc. Saturated or unsaturated, linear or branched fatty acids of ~ 30 (preferably 18-22) can be mentioned. "Branch" may be read as "iso".

In addition, examples of fatty acids include monomeric acid, dimer acid, trimer acid, or a combination thereof. Examples of fatty acids that are a combination of monomeric acid, dimer acid, and trimer acid are Tsunodim 205 (10% by mass of monomeric acid, 76% by mass of dimer acid, 14% by mass of trimer acid) and Tsunodim 216 manufactured by Tsukino Food Industry Co., Ltd. (7% by mass of monomeric acid, 77% by mass of dimer acid, 14% by mass of trimer acid), Tsunodim 228 (5% by mass of monomeric acid, 81% by mass of dimer acid, 14% by mass of trimer acid), Tsunodim 395 (3% by mass of monomeric acid). , 94% by mass of dimer acid, 3% by mass of trimer acid), tunodime 346 (2% by mass of monomeric acid, 28% by mass of dimer acid, 70% by mass of trimer acid) and the like.

The ester is produced by subjecting the alcohol to an esterification reaction with the fatty acid. Since such a reaction has been sufficiently established in the past, it may be followed in the present invention. Ester also purchases commercially available products such as TFE-30A (manufactured by Tsukino Food Industry Co., Ltd.), TFE-40A (manufactured by Tsukino Food Industry Co., Ltd.), and TFE-220A (manufactured by Tsukino Food Industry Co., Ltd.). It can also be obtained by doing.

Two or more different fatty acid esters Two or more different fatty acid esters satisfy the following conditions (1) and (2).
(1) The difference in the flow points of two or more different fatty acid esters is within 25 ° C. (2) The total number of ester bonds of two or more different fatty acid esters is 5 or more. The number of different fatty acid esters is 2 or more. For example, it may be 2 to 10, 2 to 8, 2 to 6, or 2 to 3.

Since the method for measuring the pour point has been sufficiently established in the past, it may be followed in the present invention. As a method for measuring the pour point, for example, the method described in Examples described later may be adopted. As a method for measuring the pour point, for example, an automatic pour point / cloud point tester mpc-6 type (manufactured by Tanaka Kagaku Kikai Seisakusho Co., Ltd.) may be used and the method described in the instruction manual may be followed. This measurement method complies with the American standard (ASTM D6749-02 (2018) standard test method for the pour point of petroleum products (automatic air pressure method)) and also the Japanese Industrial Standards (JIS 2269: 1987 for crude oil and petroleum products). It is a measurement method compatible with the pour point and petroleum product clouding point test method). Specifically, after putting various fatty acids up to the marked line in the measurement cell of the tester and preheating to 45 ° C, 4 ° C / min until the expected point + 40 ° C, and 1 ° C / min until the end of the test thereafter. It is preferable to cool at the rate of.

The difference in pour points of two or more different fatty acid esters is within 25 ° C, preferably within 20 ° C, more preferably within 16 ° C, still more preferably within 10 ° C, and particularly preferably within 6 ° C. Within.
When the number of different fatty acid esters is 3 or more, the fatty acid ester for which the difference in flow points is to be obtained may be, for example, two different fatty acid esters having the largest difference in flow points, and the difference in flow points is different. It may be the two smallest two different fatty acid esters, two randomly selected different fatty acid esters, or all the different fatty acid esters.

The sum of the ester bonds of two or more different fatty acid esters is the sum of the number of ester bonds of each fatty acid ester.
The sum of the ester bonds of two or more different fatty acid esters is 5 or more, for example, 5 to 30, 5 to 24, 5 to 18, 5 to 12 It may be 5-9.

Mass Ratio and Mass Ratio of Two or More Different Fatty Acid Esters The mass ratio and mass ratio of two or more different fatty acid esters are not particularly limited as long as the effects of the present invention are not lost. The mass ratio of the two or more different fatty acid esters is preferably 5% by mass or more and more preferably 10% by mass or more of each of the two or more different fatty acid esters with respect to the total mass of the fatty acid ester mixture. , 15% by mass or more is further preferable, 20% by mass or more is further preferable, and 25% by mass or more is particularly preferable.

When two or more different fatty acid esters are two different fatty acid esters A and B, the mass ratio (A: B) is preferably, for example, 1: (1/19 to 19), and 1: (1/3 to 1/3 to). 3) is more preferable, and 1: 1 is particularly preferable.
When two or more different fatty acid esters are three different fatty acid esters A, B and C, the mass ratio (A: B: C) is, for example, 1: (1/19-19) :( 1/19- 19) is preferable, 1: (1/3 to 3) :( 1/3 to 3) is more preferable, and 1: 1: 1 is particularly preferable.
When two or more different fatty acid esters are four different fatty acid esters A, B, C and D, the mass ratio (A: B: C: D) is, for example, 1: (1/19-19) :( 1/19 to 19): (1/19 to 19) is preferable, 1: (1/3 to 3) :( 1/3 to 3) :( 1/3 to 3) is more preferable, 1: 1: 1: 1 is particularly preferred.
When two or more different fatty acid esters are five different fatty acid esters A, B, C, D and E, the mass ratio (A: B: C: D: E) is, for example, 1: (1/19 to). 19): (1/19 to 19): (1/19 to 19): (1/19 to 19) is preferable, 1: (1/3 to 3): (1/3 to 3): (1 /). 3 to 3): (1/3 to 3) is more preferable, and 1: 1: 1: 1: 1 is particularly preferable.

When two or more different fatty acid esters are six different fatty acid esters A, B, C, D, E and F, the mass ratio (A: B: C: D: E: F) is, for example, 1: ( 1/19 to 19) :( 1/19 to 19) :( 1/19 to 19) :( 1/19 to 19): (1/19 to 19) is preferable, 1: (1/3 to 3) : (1/3 to 3) :( 1/3 to 3) :( 1/3 to 3): (1/3 to 3) is more preferable, and 1: 1: 1: 1: 1: 1 is particularly preferable. ..
When two or more different fatty acid esters are seven different fatty acid esters A, B, C, D, E, F and G, the mass ratio (A: B: C: D: E: F: G) is, for example, , 1: (1/19-19) :( 1/19-19) :( 1/19-19) :( 1/19-19) :( 1/19-19) :( 1/19-19) Is preferable, 1: (1/3 to 3) :( 1/3 to 3) :( 1/3 to 3) :( 1/3 to 3) :( 1/3 to 3) :( 1/3 to 3): 3) is more preferable, and 1: 1: 1: 1: 1: 1: 1 is particularly preferable.
When two or more different fatty acid esters are eight different fatty acid esters A, B, C, D, E, F, G and H, the mass ratio (A: B: C: D: E: F: G: H) ) Is, for example, 1: (1/19 to 19) :( 1/19 to 19) :( 1/19 to 19) :( 1/19 to 19) :( 1/19 to 19) :( 1 / 19 to 19): (1/19 to 19) is preferable, 1: (1/3 to 3) :( 1/3 to 3) :( 1/3 to 3) :( 1/3 to 3) :( 1/3 to 3) :( 1/3 to 3): (1/3 to 3) is more preferable, and 1: 1: 1: 1: 1: 1: 1: 1 is particularly preferable.

When two or more different fatty acid esters are nine different fatty acid esters A, B, C, D, E, F, G, H and I, the mass ratio (A: B: C: D: E: F: G) : H: I) is, for example, 1: (1/19 to 19) :( 1/19 to 19) :( 1/19 to 19) :( 1/19 to 19) :( 1/19 to 19). : (1/19 to 19): (1/19 to 19): (1/19 to 19) is preferable, 1: (1/3 to 3) :( 1/3 to 3) :( 1/3 to 3) 3) :( 1/3 to 3) :( 1/3 to 3) :( 1/3 to 3) :( 1/3 to 3): (1/3 to 3) is more preferable, 1: 1: 1: 1: 1: 1: 1: 1: 1 is particularly preferable.
When 2 or more different fatty acid esters are 10 different fatty acid esters A, B, C, D, E, F, G, H, I and J, the mass ratio (A: B: C: D: E: F) : G: H: I: J) is, for example, 1: (1 / 19-19) :( 1/19-19) :( 1/19-19) :( 1/19-19) :( 1 / 19-19) :( 1/19-19) :( 1/19-19) :( 1/19-19) :( 1/19-19) is preferable, 1: (1/3-3) :( 1/3 to 3) :( 1/3 to 3) :( 1/3 to 3) :( 1/3 to 3) :( 1/3 to 3): (1/3 to 3): (1 / 3 to 3): (1/3 to 3) is more preferable, and 1: 1: 1: 1: 1: 1: 1: 1: 1: 1 is particularly preferable.

The mixing conditions such as the temperature condition and the stirring condition in the step of mixing the different fatty acid esters of the mixing step 2 or more are not particularly limited, and it is preferable that the mixture is uniformly mixed as a result of the mixing. The temperature condition may be, for example, about 0 to 30 ° C. or about 0 to 25 ° C. A known stirrer (including laboratory-scale and factory-scale) may be used for stirring. The stirring time may be, for example, about 5 to 60 minutes or about 10 to 30 minutes.

Effect By the above mixing step, the pour point of the obtained fatty acid ester mixture can be lowered from the pour point of each fatty acid ester before the mixing step. By lowering the pour point of the obtained fatty acid ester mixture, for example, the fatty acid ester mixture has fluidity even in a low temperature environment, and workability is improved. In the present disclosure, the low temperature is, for example, −10 ° C. to 20 ° C., preferably −10 ° C. to 10 ° C., more preferably −10 to 5 ° C., and further preferably 0 to 3 ° C. .. The obtained fatty acid ester mixture is useful as, for example, lubricating oil, metal processing oil, rolling oil, metal cutting oil and the like.

The present invention includes various combinations of the above-mentioned configurations within the technical scope of the present invention as long as the effects of the present invention are exhibited.

Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples, and many modifications are made in the art within the technical idea of the present invention. It is possible by someone with normal knowledge.

1. 1. Raw materials for fatty acid esters The raw materials used for the production of fatty acid esters are as follows.
(alcohol)
2-Ethylhexanol (2EH); Brand name: 2-Ethylhexanol; Neopentyl glycol (NPG) manufactured by Mitsubishi Gas Chemical Company, Ltd .; Trimethylolpropane (TMP) manufactured by Mitsubishi Gas Chemical Company, Inc .; Pentaerythritol manufactured by Mitsubishi Gas Chemical Company, Inc. ( PE); Perstopp dipentaerythritol (DiPE); Perstopp (fatty acid)
Heptanoic acid (C7); Trade name: OLERIS (registered trademark) n-heptanoic acid; Octanoic acid (C8) manufactured by Alchema Co., Ltd .; Trade name: Lunac 8-98; Decanoic acid (C10) manufactured by Kao Co., Ltd .; Trade name: Lunac 10-98; Isononanoic acid (iC9) manufactured by Kao Co., Ltd .; Trade name: Kyowanoic N; Isostearic acid (iC18) manufactured by KH Neochem Co., Ltd .; The branched fatty acid contained in the monomeric acid (for example, TFA-45, manufactured by Tsukino Food Industry Co., Ltd.) produced by the polymerization of unsaturated fatty acid such as fatty acid, tall oil fatty acid, or tall oil fatty acid is separated. can get.
Oleic acid (OL); Product name: SINAR-OL; Trimmer acid manufactured by SOCI MAS; Product name: Td346; Manufactured by Tsukino Food Industry Co., Ltd.
(Commercially available fatty acid ester)
Ester of pentaerythritol and fatty acid (octanoic acid, decanoic acid); Product name: TFE-30A: Ester of pentaerythritol and fatty acid (octanoic acid, isononanoic acid, decanoic acid) manufactured by Tsukino Food Industry Co., Ltd .; Product name: TFE-40A; Ester of dipentaerythritol manufactured by Tsukino Food Industry Co., Ltd. and fatty acids (heptanic acid, octanoic acid, isononanoic acid, decanoic acid); Trade name: TFE-220A; Manufactured by Tsukino Food Industry Co., Ltd.

2. 2. Pour point measurement method Using an automatic pour point / cloud point tester mpc-6 type (manufactured by Tanaka Kagaku Kikai Seisakusho Co., Ltd.), the pour points of various fatty acid esters are measured and evaluated according to the method described in the instruction manual. Was done. This measurement method complies with the American standard (ASTM D6749-02 (2018) standard test method for the pour point (automatic air pressure method) of petroleum products), and also the Japanese industrial standard (JIS 2269: 1987 crude oil and petroleum). It is a measurement method that corresponds to the pour point of products and the pour point of petroleum products). Specifically, after putting various fatty acids up to the marked line in the measurement cell of the tester and preheating to 45 ° C, 4 ° C / min until the expected point + 40 ° C, and 1 ° C / min until the end of the test thereafter. Cooled at the speed of.

3. 3. Production of Fatty Acid Ester and Measurement of Flow Point Table 1 below shows the fatty acid ester obtained by subjecting the above raw material alcohol and the raw material fatty acid to an esterification reaction and the commercially available fatty acid ester used.

[Method for producing fatty acid esters of A and M]
569 g (2.00 mol) of isostearic acid, 91 g (0.87 mol) of neopentyl glycol, and tin oxide as a catalyst in a 1 L four-necked flask equipped with a stirrer, a thermometer, and a Dean-Stark tube with a condenser. Was charged in an amount of 0.05% by weight based on the total amount, and the temperature was raised to 230 ° C. in a nitrogen atmosphere. After reaching 230 ° C., the pressure was reduced, and the esterification reaction was carried out while removing the distilled water with a Dean-Stark tube. The reaction was terminated when the hydroxyl value became 5.0 mgKOH / g or less. After completion of the reaction, 0.2% by weight of activated carbon and activated clay were added to the crude esterified product, and the mixture was stirred at 80 ° C. for 30 minutes and then under reduced pressure for 1 hour. Then, the pressure was returned to normal pressure and filtered to remove them. Then, the excess acid and the low boiling point component of the obtained esterified filtrate were distilled off by a thin film distiller to obtain the fatty acid ester (esters A and M) of the present invention.

[Method for producing fatty acid esters of B and D]
Td346 424 g (0.50 mol), 2-ethylhexanol 260 g (2.00 mol) in a 1 L 4-neck flask equipped with a stirrer, thermometer, Dean-Stark tube with condenser, and tin oxide as a catalyst. Was charged in an amount of 0.1% by weight based on the total amount, and the temperature was raised to 230 ° C. in a nitrogen atmosphere. After reaching 230 ° C., the pressure was reduced, and the esterification reaction was carried out while removing the distilled water with a Dean-Stark tube. The reaction was terminated when the acid value became 1.0 mgKOH / g or less. After completion of the reaction, 0.2% by weight of activated carbon and activated clay were added, and the mixture was stirred at 80 ° C. for 30 minutes and then under reduced pressure for 1 hour. Then, the pressure was returned to normal pressure and filtered to remove them. Then, the excess alcohol and the low boiling point component of the obtained crude esterified product were removed by thin film distillation to obtain the fatty acid esters (esters B and D) of the present invention.

[Method for producing fatty acid ester of C]
The present invention is carried out by the same method as that for producing A, except that 78 g (0.58 mol) of trimethylolpropane was used instead of neopentyl glycol and 565 g (2.00 mol) of oleic acid was used instead of isostearic acid. A fatty acid ester (ester C) was obtained.

[Method for producing fatty acid esters of E and G]
The fatty acid ester (esters E and G) of the present invention was obtained by the same method as the method for producing A except that 78 g (0.58 mol) of trimethylolpropane was used instead of neopentyl glycol.

[Fatty acid ester production method of F]
110 g (0.81 mol) of pentaerythritol instead of neopentyl glycol, 198 g (1.37 mol) of octanoic acid instead of isostearic acid, 164 g (1.04 mol) of isononanoic acid, 237 g (1.38 mol) of decanoic acid The fatty acid ester (ester F) of the present invention was obtained by the same method as the production method of A except that the above was used.

[Method for producing fatty acid esters of H, J, L]
Dipentaerythritol 134 g (0.53 mol) instead of neopentyl glycol, heptanoic acid 37 g (0.29 mol), octanoic acid 33 g (0.23 mol), isononanoic acid 469 g (2.97 mol) instead of isostearic acid ), The fatty acid ester (ester H, J, L) of the present invention was obtained by the same method as the method for producing A except that 41 g (0.24 mol) of decanoic acid was used.

[Method for producing fatty acid ester of I]
Method for producing A except that 101 g (0.75 mol) of pentaerythritol was used instead of neopentyl glycol, 324 g (2.24 mol) of octanoic acid and 215 g (1.25 mol) of decanoic acid were used instead of isostearic acid. The fatty acid ester (ester I) of the present invention was obtained by the same method as above.

[Method for producing fatty acid ester of K]
The present invention was carried out by the same method as that for producing A, except that 121 g (0.48 mol) of dipentaerythritol was used instead of neopentyl glycol and 522 g (3.30 mol) of isononanoic acid was used instead of isostearic acid. A fatty acid ester (ester K) was obtained.

[Method for producing N fatty acid ester]
The fatty acid ester (ester N) of the present invention was obtained by the same method as the method for producing A except that 508 g (3.90 mol) of enanthic acid was used instead of isostearic acid.

4. Confirmation results of physical properties Table 2 below shows the pour point measurement results of the fatty acid ester mixture.

FIG. 1 shows changes in the pour point when the fatty acid esters C and D are mixed, including the cases of Examples 2a to 2c.

As is clear from Tables 1 and 2 and FIG. 1, in the examples, the difference in the flow points of the fatty acid esters used is within 25 ° C., and the total number of ester bonds is 5 or more, and the fatty acids. The flow point of the ester mixture was lower than any of the flow points of the fatty acid ester used. On the other hand, in the comparative example, the difference in the flow points of the fatty acid esters used is far more than 25 ° C., and the total number of ester bonds is 4, that is, less than 5, and the flow points of the fatty acid ester mixture. Was higher than the flow point of the fatty acid ester used.

By the method of the present invention, the pour point of the obtained fatty acid ester mixture can be lowered from the pour point of each fatty acid ester before the mixing step. By lowering the pour point of the obtained fatty acid ester mixture, for example, the fatty acid ester mixture has fluidity even in a low temperature environment, and workability is improved. The obtained fatty acid ester mixture is useful as, for example, lubricating oil, metal processing oil, rolling oil, metal cutting oil and the like.

Claims (2)

A method for lowering the flow point of the obtained fatty acid ester mixture from the flow point of each fatty acid ester before the mixing step, which comprises a step of mixing two or more different fatty acid esters satisfying the following conditions (1) and (2). The method, wherein the two or more different fatty acid esters contain any of the following (I)-(VI) :
(1) The difference between the pour points of two or more different fatty acid esters is within 25 ° C.
(2) The total number of ester bonds of two or more different fatty acid esters is 5 or more .
(I) (A) Esters of neopentyl glycol and isostearic acid and (B) Esters of 2-ethylhexanol and trimeric acid,
(II) (C) Ester of trimethylolpropane and oleic acid and (D) Ester of 2-ethylhexanol and trimeric acid,
(III) (E) Esters of trimethylolpropane and isostearic acid and (F) Esters of fatty acids consisting of pentaerythritol and octanic acid, isononanoic acid and decanoic acid,
(IV) (G) Esters of trimethylolpropane and isostearic acid and (H) Esters of fatty acids consisting of dipentaerythritol and heptanic acid, octanoic acid, isononanoic acid and decanoic acid,
(V) (I) Ester of pentaerythritol and fatty acid consisting of octanoic acid and decanoic acid and (J) Ester of dipentaerythritol and ester of fatty acid consisting of heptanic acid, octanoic acid, isononanoic acid and decanoic acid, or
(VI) (K) Ester of dipentaerythritol and isononanoic acid and (L) Ester of fatty acid consisting of dipentaerythritol and heptanic acid, octanoic acid, isononanoic acid and decanoic acid . The method according to claim 1, wherein each of two or more different fatty acid esters is contained in an amount of 5% by mass or more based on the total mass of the fatty acid ester mixture.

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