Composition

Abstract

An object of the present disclosure is to provide a novel composition. Preferably, an object of the present disclosure is to provide a water-soluble composition. Preferably, an object of the present disclosure is to provide a composition for preventing adhesion of asphalt mixtures. More preferably, an object of the present disclosure is to provide a composition that has high asphalt mixture adhesion prevention performance even at low concentrations when dissolved in water. More preferably, an object of the present disclosure is to provide a composition for preventing adhesion of asphalt mixtures that is excellent in safety and environmental friendliness, does not cause dissolution of asphalt, and causes little damage to rubber materials such as tires. The present disclosure provides a composition obtained by transesterifying an oil or fat composition with a polyalkylene glycol.

Description

[Technical Field]

[0001] The present disclosure relates to compositions. [Background technology]

[0002] Mineral oil and heavy oil were previously used as asphalt mixture anti-adhesion agents, but they had problems such as adverse effects on the surrounding environment, dissolution of asphalt on pavement surfaces, accelerated tire deterioration, and flammability. Anti-adhesion agents used by diluting with water have been developed as asphalt mixture anti-adhesion agents with performance equal to or better than that of mineral oil and heavy oil. Emulsion-type agents containing surfactants have been developed to improve miscibility with water, but to achieve good results, they required the inclusion of large amounts of animal and vegetable oils and terpene compounds. As a result, after dilution with water, oil-water separation occurred over time in the tank, creating a concentration gradient, which led to the problem of insufficient effectiveness. Furthermore, those containing vegetable oils or fats have problems such as dissolution of asphalt, discoloration, reduction in surface hardness, etc. To solve these problems, asphalt mixture anti-adhesion agents using polyalkylene glycol derivatives that do not contain oily components and have high affinity for water have been reported, but there is a problem that they are insufficiently effective at low concentrations.

[0003] Various compositions relating to anti-adhesion agents for asphalt mixtures are known (Patent Documents 1 to 26).

[0004] However, the above document does not disclose the specific compositions of some embodiments of the present disclosure. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 2019-6885 [Patent Document 2] Japanese Patent Application Laid-Open No. 2015-78297 [Patent Document 3] Japanese Patent Application Laid-Open No. 2015-52040 [Patent Document 4] Japanese Patent Application Laid-Open No. 2015-44901 [Patent Document 5] Japanese Patent Application Laid-Open No. 2014-185200 [Patent Document 6] Japanese Patent Application Laid-Open No. 2014-185199 [Patent Document 7] Japanese Patent Application Laid-Open No. 2014-156564 [Patent Document 8] International Publication No. 2014 / 024801 [Patent Document 9] Japanese Patent Application Laid-Open No. 2013-185018 [Patent Document 10] Japanese Patent Application Laid-Open No. 2013-91691 [Patent Document 11] Japanese Patent Application Laid-Open No. 2013-87164 [Patent Document 12] Japanese Patent Application Laid-Open No. 2013-79298 [Patent Document 13] Japanese Patent Application Laid-Open No. 2012-211248 [Patent Document 14] Japanese Patent Application Laid-Open No. 2011-63787 [Patent Document 15] Japanese Patent Application Laid-Open No. 2010-100731 [Patent Document 16] Japanese Patent Application Laid-Open No. 2009-144030 [Patent Document 17] Japanese Patent Application Laid-Open No. 2007-302710 [Patent Document 18] Japanese Patent Application Laid-Open No. 2007-231093 [Patent Document 19] Japanese Patent Application Laid-Open No. 2006-241409 [Patent Document 20] Japanese Patent Application Laid-Open No. 2006-182859 [Patent Document 21] Japanese Patent Application Laid-Open No. 2004-244548 [Patent Document 22] Japanese Patent Application Laid-Open No. 2002-47448 [Patent Document 23] Japanese Patent Application Laid-Open No. 2001-303021 [Patent Document 24] Japanese Patent Application Publication No. 11-315267 [Patent Document 25] Japanese Patent Application Publication No. 7-292346 [Patent Document 26] Japanese Patent Application Publication No. 7-90286 Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present disclosure is to provide a novel composition. Preferably, an object of the present disclosure is to provide a water-soluble composition. Preferably, an object of the present disclosure is to provide a composition for preventing adhesion of asphalt mixtures. More preferably, an object of the present disclosure is to provide a composition that has high asphalt mixture adhesion prevention performance even at low concentrations when dissolved in water. More preferably, an object of the present disclosure is to provide a composition for preventing adhesion of asphalt mixtures that is excellent in safety and environmental friendliness, does not cause dissolution of asphalt, and causes little damage to rubber materials such as tires. [Means for solving the problem]

[0007] As a result of extensive research, the present inventors have discovered a composition having several characteristics by transesterifying an oil or fat composition with a polyalkylene glycol.

[0008] The present disclosure relates to the following inventions, etc. [1] A composition obtained by transesterifying an oil or fat composition with a polyalkylene glycol. [2] The composition according to [1] above, wherein the polyalkylene glycol has a number average molecular weight of 200 to 4,000. [3] The composition according to [1] or [2] above, wherein the molar ratio of the oil or fat composition to the polyalkylene glycol is 3:1 to 1:9. [4] The composition according to any one of the above [1] to [3], wherein the polyalkylene glycol has an EO / PO (oxyethylene group / oxypropylene group) content ratio (number average molecular weight ratio) of 100 / 0 to 12.5 / 87.5. [5] An aqueous solution containing the composition according to any one of [1] to [4] above. [6] A lubricating composition comprising the aqueous solution of [5]. [7] The composition according to any one of [1] to [4] and [6], which is used to prevent adhesion of asphalt mixtures. [8] The composition according to [1] or [2] above, which is water-soluble. [9] The composition according to [1] or [2] above, wherein a mixture of water and the composition in a 1:1 mass ratio is homogeneous and transparent when left to stand for 5 minutes. [Effects of the Invention]

[0009] According to the present disclosure, a novel composition can be provided. According to the present disclosure, preferably, a water-soluble composition can be provided. According to the present disclosure, preferably, a composition for preventing adhesion of asphalt mixtures can be provided. According to the present disclosure, more preferably, a composition can be provided that has high asphalt mixture adhesion prevention performance even when dissolved in water at a low concentration (e.g., less than 10% by mass, less than 5% by mass, 0.5% by mass or more, etc.). According to the present disclosure, more preferably, a composition for preventing adhesion of asphalt mixtures that is excellent in safety and environmental friendliness, does not cause dissolution of asphalt, and causes little damage to rubber materials such as tires. [Brief explanation of the drawings]

[0010] [Figure 1] 1 shows a calibration curve of the peak height (μV) of the triacylglyceride (TAG) peak versus the amount of triacylglyceride (%) measured using canola oil and PEG-600. DETAILED DESCRIPTION OF THE INVENTION

[0011] <Composition> The present disclosure provides a composition obtained by transesterifying an oil or fat composition with a polyalkylene glycol (for example, mixing the oil or fat composition with a polyalkylene glycol and heating the mixture at a temperature above room temperature, for example, 40 to 250°C, in the presence of a catalyst such as an organometallic catalyst, an acid catalyst, or a base catalyst, or mixing the oil or fat composition with a polyalkylene glycol and heating the mixture at 40 to 230°C). The composition may contain several esters obtained by transesterifying the oil or fat composition with a polyalkylene glycol. The composition may or may not contain optional components other than the esters. The composition may contain glycerin and / or a polyalkylene glycol in addition to the esters. The composition may or may not contain a surfactant, but preferably does not contain one. In this case, however, the surfactant is preferably a surfactant other than a composition obtained by transesterifying an oil / fat composition with a polyalkylene glycol. Even if the composition does not contain a surfactant, it can have the characteristic of having high anti-adhesion performance for asphalt mixtures even at low concentrations (e.g., less than 10% by mass, less than 5% by mass, 0.5% by mass or more) when dissolved in water. The composition may or may not contain a silicone such as dimethylpolysiloxane, but preferably does not contain one. The composition may or may not contain an ether, but preferably does not contain one.

[0012] The composition can be used, for example, as a metalworking oil composition such as cutting oil, sliding surface oil, bearing oil, hydraulic equipment oil, engine oil, turbine oil, compressor oil, chain oil, gear oil, grease oil, rolling oil, or bearing oil, or as a lubricating composition such as a composition for preventing adhesion of asphalt mixtures. The metalworking oil composition can also be suitably used for heavy processing, processing of difficult-to-process materials, or processing of difficult-to-process materials. The type of metalworking is not particularly limited, but specific examples include cutting, grinding, rolling, forging, pressing, drawing, and rolling. The amount used may be the amount generally used for metalworking oil or lubricating oil. The present disclosure also encompasses lubricants, such as metal-working agents or asphalt mix anti-adhesion agents, that include the composition.

[0013] <Oil composition> The oil and fat composition used is an ester of a fatty acid and glycerin. The fatty acid may be an unsaturated fatty acid such as oleic acid, linoleic acid, or linolenic acid; a linear saturated fatty acid such as lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, or behenic acid; a branched saturated fatty acid such as isostearic acid, 2,2-dimethyloctanoic acid, or 3-methylbutanoic acid; a saturated fatty acid having 14 to 22 carbon atoms; or a saturated fatty acid having 16 to 18 carbon atoms; or may contain other various fatty acids or a combination thereof. For example, the oil and fat composition may contain at least palmitic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid. The oil and fat composition used may also contain triacylglyceride (TAG).

[0014] (Composition of fatty acids constituting the oil and fat composition used) When palmitic acid is included as a fatty acid constituting the oil-and-fat composition used, the ratio of palmitic acid to the total fatty acids constituting the oil-and-fat composition used may, for example, have a lower limit of 0.01%, 0.1%, 1.0%, 2.0%, 3.0%, 4.0%, or 4.5%, and an upper limit of 50%, 40%, 35%, 30%, 25%, 20%, 15%, or 12%, or may be a combination of the above lower and upper limits. Specifically, for example, the ratio is preferably 1 to 35%, more preferably 1 to 25%, and even more preferably 4 to 12%. In the present disclosure, when simply "%" is used, it may be "% by mass." When stearic acid is included as a fatty acid constituting the oil or fat composition used, the ratio of stearic acid to the total fatty acids constituting the oil or fat composition used may be, for example, a lower limit of 0.01%, 0.1%, 0.5%, 1.0%, 1.2%, 2.0%, 3.0%, or 3.5%, and an upper limit of 30%, 20%, 10%, 6.0%, 5.0%, 4.0%, or 3.6%, or a combination of the above lower and upper limits. Specifically, for example, the ratio is preferably 0.1 to 20%, more preferably 1 to 6%, and even more preferably 1 to 4%. When oleic acid is contained as a fatty acid constituting the oil-and-fat composition used, the ratio of oleic acid to all the fatty acids constituting the oil-and-fat composition used may be, for example, 1%, 7%, 10%, 20%, 30%, 40%, or 44% as a lower limit, or 95%, 90%, 85%, 80%, 70%, 67%, or 63% as an upper limit, or a combination of the above lower and upper limits. Specifically, for example, it is preferably 7 to 85%, more preferably 30 to 70%, and even more preferably 44 to 63%. When linoleic acid is contained as a fatty acid constituting the oil or fat composition used, the ratio of linoleic acid to the total fatty acids constituting the oil or fat composition used may be, for example, a lower limit of 0.1%, 1.5%, 5%, 10%, 15%, 18%, 20%, or 21%, or an upper limit of 60%, 55%, 50%, 40%, 35%, or 34%, or a combination of the above lower and upper limits. Specifically, for example, it is preferably 1.5 to 55%, more preferably 10 to 40%, and even more preferably 20 to 40%. When linolenic acid is included as a fatty acid constituting the oil or fat composition used, the ratio of linolenic acid to the total fatty acids constituting the oil or fat composition used may be, for example, a lower limit of 0%, 0.01%, 0.1%, 1.0%, 3.0%, 5.0%, or 6.0%, and an upper limit of 65%, 50%, 40%, 30%, 20%, 10%, 9.8%, or 9.6%, or a combination of the above lower and upper limits. Specifically, for example, it is preferably 0 to 65%, more preferably 3 to 20%, and even more preferably 6 to 10%.

[0015] In one embodiment, when palmitic acid and stearic acid are included as fatty acids constituting the oil and fat composition used, the ratio of palmitic acid to the total fatty acids constituting the oil and fat composition used is preferably higher than that of stearic acid (e.g., 2 times or more, 3 times or more, 3.3 times or more). In one embodiment, when stearic acid and oleic acid are included as fatty acids constituting the oil and fat composition used, the ratio of oleic acid to the total fatty acids constituting the oil and fat composition used is preferably higher than that of stearic acid (e.g., 10 times or more, 12 times or more). In one embodiment, when oleic acid and linoleic acid are included as fatty acids constituting the oil and fat composition used, the ratio of oleic acid to the total fatty acids constituting the oil and fat composition used is preferably higher than that of linoleic acid (e.g., 1.2 times or more, 1.3 times or more). In one embodiment, when linoleic acid and linolenic acid are included as fatty acids constituting the oil and fat composition used, the ratio of linoleic acid to the total fatty acids constituting the oil and fat composition used is preferably higher than that of linolenic acid (e.g., 2 times or more, 2.2 times or more). In one embodiment, when the fatty acids constituting the oil and fat composition used include palmitic acid and oleic acid, the ratio of oleic acid to the total fatty acids constituting the oil and fat composition used is preferably higher than that of palmitic acid (e.g., 3 times or more, 3.5 times or more). In one embodiment, when the fatty acids constituting the oil and fat composition used include palmitic acid and linoleic acid, the ratio of linoleic acid to the total fatty acids constituting the oil and fat composition used is preferably higher than that of palmitic acid (e.g., 2 times or more, 2.5 times or more). In one embodiment, when the fatty acids constituting the oil and fat composition used include stearic acid and linoleic acid, the ratio of linoleic acid to the total fatty acids constituting the oil and fat composition used is preferably higher than that of stearic acid (e.g., 9 times or more, 9.4 times or more). In one embodiment, when the fatty acids constituting the oil and fat composition used include stearic acid and linolenic acid, the ratio of linolenic acid to the total fatty acids constituting the oil and fat composition used is preferably higher than that of stearic acid (e.g., 1.3 times or more, 1.6 times or more).In one embodiment, when the fatty acids constituting the oil and fat composition used include oleic acid and linolenic acid, the ratio of oleic acid to the total fatty acids constituting the oil and fat composition used is preferably greater than that of linoleic acid (e.g., 6 times or more, 7 times or more). In the present disclosure, when the term "ratio" is used, it may be "mass ratio."

[0016] When the fatty acids constituting the oil and fat composition used as one embodiment include at least palmitic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid, the ratio of these fatty acids (palmitic acid:stearic acid:oleic acid:linoleic acid:linolenic acid) (mass ratio) when the total fatty acids constituting the oil and fat composition is taken as 100 is, for example, (1 to 12):(0.1 to 3.7):(35 to 44.3):(20 to 33.9):(3 to 6.1), (5 to 12):(1 to 3.7):( 40-44.3):(25-33.9):(4-6.1), (7-11.9):(3-3.6):(41-44.1):(27-33.7):(5-6), (1-4.5):(0.1-1.2):(40-62.9):(10-21.8):(1-9.6), (2-4.5):(0.5-1.2):(50-62.9):(15-21.8):(3-9.6), (3-4.5):(0.8-1.2):(45-62.9):(17-21.8):(5-9.6). The proportion of fatty acids constituting these oil and fat compositions can be calculated by a known method such as gas chromatography after hydrolyzing the oil and fat composition.

[0017] In one embodiment, when the fatty acids constituting the oil and fat composition used include oleic acid and linoleic acid, the proportion of oleic acid relative to the total fatty acids constituting the oil and fat composition used is preferably 40 to 65%, and the proportion of linoleic acid is preferably 20 to 40%. In one embodiment, the oil and fat composition preferably contains 11.9% palmitic acid, 3.6% stearic acid, 44.1% oleic acid, 33.7% linoleic acid, and 6.0% linolenic acid relative to the total fatty acids constituting the oil and fat composition (e.g., Refined No. 2 Oil (manufactured by Tsuno Oleochemicals Co., Ltd.)). In another embodiment, the proportion of palmitic acid relative to the total fatty acids constituting the oil or fat composition used is preferably 4.5%, stearic acid 1.2%, oleic acid 62.9%, linoleic acid 21.8%, and linolenic acid 9.6% (e.g., canola oil). The proportions of fatty acids constituting these oil and fat compositions can be calculated by known methods such as gas chromatography after hydrolysis of the oil and fat composition. In addition, by appropriately combining the preferred proportions of these various fatty acids, it is possible to apply the fatty acid composition within a preferred range in the oil and fat composition to be used.

[0018] (Specific examples of oil and fat compositions) In the present disclosure, examples of oil and fat compositions include edible vegetable oils such as rapeseed oil (e.g., canola oil), soybean oil, olive oil, sesame oil, grape oil, coconut oil, linseed oil, perilla oil, sunflower oil, corn oil, cottonseed oil, rice oil, palm oil, and wheat germ oil, as well as waste cooking oil and refined No. 2 oil (manufactured by Tsuno Oleochemicals Co., Ltd.), and these edible vegetable oils, waste cooking oils, refined No. 2 oils, etc. may be used alone or mixed in any desired ratio.

[0019] <Polyalkylene glycol> In the present disclosure, polyalkylene glycol refers to one having a degree of polymerization of 4 or more. In the present disclosure, polyalkylene glycol refers to a compound obtained by polymerizing or copolymerizing alkylene oxides such as ethylene oxide and propylene oxide. Examples of polyalkylene glycols include polypropylene glycol and polyethylene glycol. Specific examples of polyethylene glycols include PEG-2000 (manufactured by Sanyo Chemical Industries, Ltd.) and PEG-600 (manufactured by Aoki Oil & Fat Industries Co., Ltd.).

[0020] In the present disclosure, the copolymerization mode of polyalkylene glycol may be either random polymerization and / or block polymerization. In the present disclosure, the polyalkylene glycol may be a polyalkylene glycol obtained by addition polymerization of alkylene oxide. The polyalkylene glycol obtained by addition polymerization of alkylene oxide may be either a random copolymer or a block copolymer, but is preferably a block copolymer. Examples of block polymerization type polyalkylene glycol obtained by addition polymerization of alkylene oxide include diblock copolymers, triblock copolymers, and tetrablock copolymers.

[0021] Examples of polyalkylene glycols obtained by addition polymerization of alkylene oxide include polyethylene glycols obtained by addition polymerization of ethylene oxide (EO), and polypropylene glycols obtained by addition polymerization of propylene oxide (PO). Polypropylene glycol obtained by addition polymerization of ethylene oxide (EO) can be referred to as, for example, a polyoxyethylene polyoxypropylene block polymer, a block copolymer of ethylene oxide (EO) and propylene oxide (PO), or a Pluronic (registered trademark) type nonionic surfactant having a polyoxypropylene chain as a hydrophobic group in the center of the molecular chain and polyoxyethylene chains as hydrophilic groups at both ends of the molecular chain. The polypropylene glycol obtained by addition polymerization of ethylene oxide may be, for example, an ethylene oxide (EO)-propylene oxide (PO) block copolymer (EO / PO block copolymer) such as EO-PO-EO or PO-EO-PO block copolymer, or may be a random copolymer. Specific examples of polypropylene glycols obtained by addition polymerization of ethylene oxide (EO) include the Newpol PE series manufactured by Sanyo Chemical Industries, Ltd., such as Newpol PE-61, Newpol PE-62, Newpol PE-64, and Newpol PE-75, and Brownon P-106 (manufactured by Aoki Oil & Fat Industries Co., Ltd.).

[0022] (EO to PO ratio of polyalkylene glycol) The ratio of EO to PO (EO / PO) (number average molecular weight ratio) of the polyalkylene glycol may be (100 / 0) to (12.5 / 87.5), may be (100 / 0) to (57 / 43), or may be (100 / 0) to (60 / 40).

[0023] (Number average molecular weight of polyalkylene glycol) The number average molecular weight of the polyalkylene glycol may be, for example, 200 to 10,000, 200 to 4,000, 400 to 4,000, 600 to 3,500, 600 to 2,500, 600 to 1,900, or 2,400 to 3,500.

[0024] (Preferable combination of type and number average molecular weight) When the polyalkylene glycol is polyethylene glycol, the number average molecular weight may be 4000 or less, less than 4000, less than 2000, 200 or more, 200 or more but less than 2000, or 400 or more and 1000 or less. When the polyalkylene glycol is an EO-PO-EO block copolymer, the number average molecular weight may be 4,000 or less, less than 4,000, more than 2,400 and less than 2,500, 2,400 or more and less than 3,500, or 2,500 or more and less than 3,100.

[0025] The polyalkylene glycol used in the transesterification reaction may be one type or two or more types.

[0026] (Molar ratio of fat / oil composition to polyalkylene glycol in transesterification reaction) The molar ratio of the oil / fat composition to the polyalkylene glycol in the transesterification reaction may be (3:1) to (1:9), may be (3:1) to (1:6), may be (1:1) to (1:3), may be (1:1) to (1:9), may be (1:3) to (1:6), or may be (1:4) to (1:6).

[0027] (Preferable combination of molar ratio of oil / fat composition to polyalkylene glycol and number average molecular weight of polyalkylene glycol in transesterification reaction) When the molar ratio of the oil / fat composition to the polyalkylene glycol in the transesterification reaction is 1:3, the number average molecular weight of the polyalkylene glycol is preferably, for example, 200 or more and 2,500 or less, 2,400 or more but less than 4,000, or 2,500 or more and 4,000 or less. When the molar ratio of the oil / fat composition to the polyalkylene glycol in the transesterification reaction is 1:1, the number average molecular weight of the polyalkylene glycol is preferably, for example, 200 or more and 2,500 or less, 2,400 or more but less than 4,000, or 2,500 or more and 4,000 or less.

[0028] (Ingredients contained in the composition) The composition may contain, for example, two or more components selected from glycerin (hereinafter also referred to as "GOL"), monoacylglyceride (hereinafter also referred to as "MAG"), diacylglyceride (hereinafter also referred to as "DAG"), triacylglyceride (hereinafter also referred to as "TAG"), polyalkylene glycol (hereinafter also referred to as "PAG"), monoester of polyalkylene glycol (hereinafter also referred to as "ME"), and diester of polyalkylene glycol (hereinafter also referred to as "DE"). The composition of the present disclosure preferably contains, for example, all of the above seven components; the components of the above seven components excluding GOL (the six components of MAG, DAG, TAG, PAG, ME, and DE); the components of the above components excluding TAG (the six components of GOL, MAG, DAG, PAG, ME, and DE); etc. The composition of the present disclosure may contain one or more of each of the above components.

[0029] The proportion of glycerin (GOL) in the entire composition in the present disclosure may be 0 to 7 mol %, 0 to 6 mol %, or 6 to 7 mol %.

[0030] The proportion of monoacylglyceride (MAG) in the entire composition in the present disclosure may be 2 to 20 mol%, 6 to 15 mol%, 6 to 8 mol%, or 10 to 15 mol%.

[0031] The proportion of diacylglyceride (DAG) in the entire composition in the present disclosure may be 1 to 30 mol %, 1 to 6 mol %, or 6 to 30 mol %.

[0032] The proportion of triacylglyceride (TAG) in the entire composition of the present disclosure may be 0 to 5% by mass, or may be 0.1 to 5% by mass.

[0033] The proportion of polyalkylene glycol (PAG) in the entire composition in the present disclosure may be 5 to 60 mol %, 5 to 54 mol %, or 30 to 54 mol %.

[0034] In the present disclosure, the proportion of polyalkylene glycol monoester (ME) relative to the entire composition may be 25 to 40 mol %, 29 to 38 mol %, or 30 to 38 mol %.

[0035] In the present disclosure, the proportion of the polyalkylene glycol diester (DE) relative to the entire composition may be 2 to 20 mol %, 2 to 15 mol %, or 2 to 7 mol %.

[0036] The molar ratio of GOL to MAG (GOL:MAG) in the composition of the present disclosure may be (0-7):(2-20), (0-6):(6-15), or (6-7):(6-12).

[0037] The molar ratio of GOL to DAG (GOL:DAG) in the composition of the present disclosure may be (0-7):(1-30), (0-6):(1-6), or (6-7):(6-30).

[0038] The molar ratio of GOL to TAG (GOL:TAG) in the composition of the present disclosure may be (0-7):(0.1-5), (0-6):(0.1-0.3), or (6-7):(0-5).

[0039] The molar ratio of GOL to PAG (GOL:PAG) in the composition of the present disclosure may be (0-7):(5-60), (0-6):(5-54), or (6-7):(30-54).

[0040] The molar ratio of GOL to ME (GOL:ME) in the composition of the present disclosure may be (0-7):(25-40), (0-6):(29-38), or (6-7):(30-38).

[0041] The molar ratio of GOL to DE (GOL:DE) in the composition of the present disclosure may be (0-7):(2-20), (0-6):(2-15), or (6-7):(2-7).

[0042] The molar ratio of MAG, DAG, TAG, ME, and DE (MAG:DAG:TAG:ME:DE) in the composition of the present disclosure may be (2-20):(1-30):(0-5):(25-40):(2-20), or may be (6-15):(1-6):(0.1-5):(29-38):(2-15), or may be (6-8):(6-30):(0.1-0.3):(30-38):(2-7).

[0043] (water soluble) In some embodiments of the present disclosure, the composition of the present disclosure is water-soluble. In some embodiments, the present disclosure provides an aqueous solution containing the composition of the present disclosure. In some embodiments, the composition of the present disclosure may be water-soluble after a certain time has elapsed since the start of the transesterification reaction between the oil or fat composition of the present disclosure and the polyalkylene glycol (e.g., 4 hours, 5 hours, 6 hours, 7 hours, etc.). The composition that has become water-soluble after the certain time has elapsed may maintain its water solubility thereafter. Before the start of the transesterification reaction (i.e., in the state of a simple mixture of the oil or fat composition and the polyalkylene glycol without the transesterification reaction), the composition is not water-soluble. In some embodiments of the present disclosure, the start of the transesterification reaction refers to the time point when the transesterification step begins. In this step, the oil or fat composition and the polyalkylene glycol are mixed, and the mixture is heated (for example, to 40 to 230°C) with or without a catalyst, if necessary (for example, alkoxytitanium, sodium methoxide, paratoluenesulfonic acid, sodium hydroxide, an enzyme, etc.).

[0044] How to check water solubility For example, if a mixture obtained by mixing a composition and water in a 1:1 ratio (by mass) is shaken well and allowed to stand for about 5 minutes, and the mixture is uniform and transparent, it is judged to be "water soluble (◯)," whereas if it is cloudy or the oil and water layers are separated, it is judged to be "not water soluble (×)." In some embodiments of the present disclosure, a composition is provided in which a mixture of water and a composition in a 1:1 mass ratio is uniform and transparent after being allowed to stand for 5 minutes.

[0045] (oil / water separation) In some embodiments of the present disclosure, the compositions of the present disclosure do not undergo oil-water separation when mixed with water.

[0046] How to check oil-water separation For example, a 50% aqueous solution obtained by mixing the composition and water in a 1:1 ratio (by mass) is shaken well, and the state of separation of the oil and water layers in the aqueous solution is checked after one month. If there is no separation, it is judged as "oil-water separation does not occur," and if there is separation, it is judged as "oil-water separation occurs."

[0047] (For preventing adhesion of asphalt mixture) In some embodiments of the present disclosure, the compositions herein are useful for preventing adhesion of asphalt mixtures.

[0048] How to check the amount of asphalt mixture adhered For example, a scoop dipped in a 0.5% aqueous solution obtained by mixing the composition and water in a ratio (mass ratio) of 0.5:99.5 is drained 10 times, and after removing the excess aqueous solution, the scoop is inserted and removed 10 times into an asphalt mixture preheated to 150°C, and the weight change before and after is measured to determine the amount of asphalt mixture adhesion. If the amount of asphalt mixture adhesion determined in this way is less than the amount of asphalt mixture adhesion determined when the composition is replaced with a conventional asphalt mixture anti-adhesion agent (e.g., Tolex TR-110 (trade name) manufactured by Tsuno Oleochemicals Co., Ltd.), the composition can be determined to have an excellent effect of preventing adhesion of asphalt mixtures.

[0049] (Attacking rubber) In some embodiments of the present disclosure, the composition of the present disclosure does not attack (e.g., damage) rubber. A composition that does not attack rubber does not cause degradation of the rubber even when it comes into contact with the rubber.

[0050] How to check the attack on rubber For example, a piece of natural rubber is placed in a 5% aqueous solution obtained by mixing the composition and water in a 5:95 ratio (by mass), and after leaving it at room temperature for 3 hours, the presence or absence of swelling of the rubber piece is determined by measuring the rate of change in mass and volume (length x width x depth), thereby evaluating its attack on rubber. If the rate of change in volume or mass thus determined is, for example, less than 1%, it is determined that the rubber has no attack, and if either rate is 1% or more, it is determined that the rubber has attack on rubber.

[0051] (Solubility of asphalt mixture) In some embodiments of the present disclosure, the composition of the present disclosure does not dissolve asphalt mixtures. When a composition that does not dissolve asphalt mixtures is brought into contact with an asphalt mixture, there is no risk of dissolving the asphalt mixture.

[0052] Method for confirming the solubility of asphalt mixtures (cutback test) For example, pieces of asphalt mixture can be placed in a 5% aqueous solution obtained by mixing the composition and water in a ratio of 5:95 (by mass), and the solution is left standing at room temperature for one week. After that, the presence or absence of a change in the color of the liquid can be confirmed (visually). For example, if the color of the liquid remains unchanged, it can be determined that the asphalt mixture is "not soluble," and if the color of the liquid changes, it can be determined that the asphalt mixture is "soluble."

[0053] (pour point) In some embodiments of the present disclosure, the composition of the present disclosure has a pour point below freezing, preferably below −5° C. Such a composition is less likely to solidify, especially in winter, and does not require heating equipment, which leads to improved work efficiency in asphalt mixtures and in work using the composition.

[0054] How to check the pour point The pour point can be measured, for example, in accordance with JIS K-2269. For example, the upper limit of the pour point of a 5 to 50% aqueous solution obtained by mixing the composition and water in a ratio (mass ratio) of 5:95 to 50:50 is, for example, preferably 0° C. or lower, more preferably −5° C. or lower, and even more preferably −7° C. or lower. The lower limit of the pour point is, for example, preferably −60° C. or higher, more preferably −50° C. or higher.

[0055] (stability) In some embodiments of the present disclosure, the composition of the present disclosure has excellent stability. The stability may be storage stability or stability against high heat (e.g., 30°C or higher, 60°C or higher).

[0056] How to check stability (mgKOH / g) For example, the stability of a composition can be confirmed by storing a 50% aqueous solution obtained by mixing the composition and water in a 1:1 ratio (by mass) at 60°C for two weeks and determining the increase in acid value. For example, the lower the increase in acid value, the more stable the composition can be determined. The increase in acid value is preferably less than 1 mgKOH / g, and more preferably less than 0.5 mgKOH / g. The acid value can be measured, for example, according to JIS K 0070-1992.

[0057] (additives) The composition of the present disclosure may contain additives, such as known additives, for example, phenolic antioxidants, metal deactivators such as benzotriazole, thiadiazole, and dithiocarbamate, acid scavengers such as epoxy compounds and carbodiimides, phosphorus-based extreme pressure agents, and pour point depressants such as polyalkyl methacrylates (e.g., Aclub 132 and Aclub 146).

[0058] When the composition of the present disclosure contains an additive, the upper limit of the content of the additive is preferably 30% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less, based on the total mass of the composition.

[0059] The composition of the present disclosure may be substantially free of additives, or may consist essentially of transesterification products (e.g., five or more products selected from the group consisting of GOL, MAG, DAG, TAG, PAG, ME, and DE). The term "substantially free of additives" in a composition means, for example, that the total content of additives is less than 5% by mass. The term "substantially consisting of transesterification products" in a composition means, for example, that the content of transesterification products is 95% by mass or more. The composition of the present disclosure also encompasses cases in which a product of a transesterification reaction (e.g., five or more products selected from the group consisting of GOL, MAG, DAG, TAG, PAG, ME, and DE) is contained without substantially being accompanied by a transesterification reaction (e.g., a composition comprising a mixture of five or more components selected from the group consisting of GOL, MAG, DAG, TAG, PAG, ME, and DE).

[0060] [Method of producing the composition] The composition according to the present disclosure can be produced, for example, by a production method including a transesterification reaction step in which an oil or fat composition and a polyalkylene glycol are subjected to a transesterification reaction.

[0061] The method for producing the composition may further include, after the transesterification step, a step of removing low-boiling components from the resulting ester to obtain a crude esterified product (hereinafter also referred to as a "low-boiling component removal step"). Alternatively, the method may further include, after the low-boiling component removal step, a step of treating the resulting crude esterified product with a treating agent (hereinafter also referred to as a "treatment step"). Each step will be described below.

[0062] (Interesterification process) In this step, the oil or fat composition and the polyalkylene glycol are mixed, and a catalyst (e.g., alkoxytitanium, sodium methoxide, paratoluenesulfonic acid, sodium hydroxide, enzymes, etc.) may be added as needed, or a catalyst may be used without adding the mixture, and the mixture is heated (e.g., 40 to 230°C, etc.) to carry out a transesterification reaction.

[0063] The equivalent ratio of the polyalkylene glycol component to the oil / fat composition component is preferably 0.1 to 2.0 moles of carboxyl groups in the oil / fat composition component per mole of hydroxyl groups in the polyalkylene glycol component, and from the viewpoints of production efficiency and economy, more preferably 0.2 to 1.7 moles, and particularly preferably 0.25 to 1.5 moles. The number of moles of hydroxyl groups in the polyalkylene glycol component can be calculated by measuring the hydroxyl value (JIS K0070).

[0064] Examples of the catalyst include metal catalysts, acid catalysts, and base catalysts. Specific examples include acid catalysts such as sulfuric acid, methanesulfonic acid, and paratoluenesulfonic acid, organometallic catalysts, and metal catalysts containing elements such as titanium, zirconium, hafnium, tin, and zinc. The amount of catalyst used is preferably 0.01 to 10% by mass, and more preferably 0.05 to 1% by mass, based on the total amount of the polyalkylene glycol component and the oil / fat composition component. It may be catalyst-free.

[0065] The lower limit of the temperature for the transesterification reaction is preferably 40° C. or higher, and may be 100° C. or higher. The upper limit of the temperature for the esterification reaction may be, for example, 250° C. or lower, 240° C. or lower, or 235° C. or lower, and preferably 230° C. or lower.

[0066] The transesterification reaction may be carried out under normal pressure or under reduced pressure, but is preferably carried out under reduced pressure in order to shorten the reaction time and remove as much water as possible from the system. The lower limit of the pressure under reduced pressure is, for example, 0.1 Torr or more, preferably 10 Torr or more, and more preferably 100 Torr or more. The upper limit of the pressure under reduced pressure is, for example, 400 Torr or less, preferably 300 Torr or less.

[0067] The lower limit of the transesterification reaction time is preferably 10 minutes or more, more preferably 30 minutes or more, even more preferably 1 hour or more, and particularly preferably 2 hours or more, and the upper limit of the transesterification reaction time is preferably 24 hours or less, more preferably 18 hours or less, even more preferably 12 hours or less, and particularly preferably 8 hours or less.

[0068] The transesterification reaction is preferably carried out while measuring the composition of the reaction solution by GC, for example. The end point of the transesterification reaction can be confirmed, for example, by GC measurement. For example, by tracking the decrease in the peak of triacylglyceride of the oil and fat composition from the GC analysis of the reaction solution, it can be considered that the oil and fat composition has been used in the transesterification reaction when the peak area (height) no longer changes (for example, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 12 hours, etc. after the start of the reaction).

[0069] The composition of the present disclosure and a mixture of a simple oil / fat composition and polyalkylene glycol without transesterification can be distinguished by GC measurement based on the difference in the peak area (height) of triacylglycerides. In GC measurement, the solids concentration in the analytical sample is kept constant. The solids refer to the composition of the present disclosure or the mixture of the oil / fat composition and polyalkylene glycol, and can be analyzed by diluting it to 0.04% by mass with a solvent such as THF. In some embodiments, when the peak area (height) of the composition of the present disclosure is compared with that of a mixture of a simple oil / fat composition and polyalkylene glycol without transesterification, the peak area (height) of the former is smaller.

[0070] As described above, in some embodiments of the present disclosure, the composition of the present disclosure is water-soluble. For example, the composition of the present disclosure may be water-soluble from a time (for example, 4 hours, 5 hours, 6 hours, 7 hours, etc. after the start of the reaction) before the time (for example, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 12 hours, etc. after the start of the reaction) when the peak area (height) of the triacylglyceride stops changing in GC measurement. Furthermore, the composition of the present disclosure may be water-soluble when the reaction rate is, for example, 86% or more, 88% or more, 90% or more, 91% or more, 92% or more, 93% or more, 95% or more, etc., when the peak area (height) of the triacylglyceride before the transesterification reaction is defined as 0% reaction rate and the peak area (height) of the triacylglyceride at the time (for example, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 12 hours after the start of the reaction) when the peak area (height) stops changing is defined as 100%. The composition of the present disclosure may be water-soluble, for example, after 5 hours or more (e.g., 5 hours, 6 hours, or 7 hours) have elapsed since the start of the transesterification reaction. The conditions for achieving water solubility described above may be used alone or in combination. Specifically, for example, the reaction rate may be 94.5% or more 6 hours or more after the start of the transesterification reaction, 93.4% or more 5 hours or more after the start of the transesterification reaction, 90.9% or more 5 hours or more after the start of the transesterification reaction, 95.8% or more 5 hours or more after the start of the transesterification reaction, or 91.8% or more 5 hours or more after the start of the transesterification reaction, and the like, and the product may be water-soluble. In some embodiments of the present disclosure, the compositions of the present disclosure may have a reaction rate of, for example, 86% or more, 88% or more, 90% or more, 91% or more, 92% or more, 93% or more, or 95% or more.

[0071] (Processing process) In this step, the obtained crude esterified product is treated with a treating agent.

[0072] Examples of the treating agent include activated carbon, activated clay, etc. The amount of the treating agent used is usually 0.01 to 5% by mass, and preferably 0.1 to 1% by mass, based on the esterified crude product.

[0073] Examples of the treatment method include adding a treatment agent to the esterified crude product, stirring at 50°C to 100°C for about 10 minutes to 2 hours, and then stirring under reduced pressure for about 10 minutes to 2 hours, and then filtering off the treatment agent.

[0074] In this disclosure, the term "degree" is intended to encompass, for example, small deviations, including within the experimental error inherent in standard methods used to measure and / or quantify a given value or range.

[0075] The present disclosure includes various combinations of the above-described configurations within the technical scope of the present disclosure, as long as the effects of the present disclosure are achieved. [Example]

[0076] Next, some embodiments of the present disclosure will be described in more detail using examples, but the embodiments of the present disclosure are not limited to these examples in any way, and many modifications can be made by a person having ordinary skill in the art within the technical spirit of the present disclosure.

[0077] (Experimental conditions) The experiments were carried out using the following raw materials and measuring instruments. In the examples, the raw materials, instruments, measuring instruments, etc. used were commercially available products unless otherwise specified.

[0078] (raw materials) Refined No. 2 oil: Tsuno Oleochemicals Co., Ltd. Canola oil: Nisshin Oillio Group Co., Ltd. PEG-600: Aoki Oil & Fat Industries Co., Ltd. Brownon P-106: Aoki Oil & Fat Industries Co., Ltd. TREX TR-110: Manufactured by Tsuno Oleochemicals Co., Ltd. Triethylene glycol (TEG): Nippon Shokubai Co., Ltd. (Measuring equipment) Gas chromatograph detector SHIMADZU GC-2014 (Measurement conditions) Column: Inertcap 1HT (length: 5.0 m, inner diameter: 0.53 mm, liquid phase film thickness: 0.25 μm) Carrier gas: Nitrogen Injection volume: 1 μL Injector temperature: 380℃ Detector (FID) temperature: 380℃ Injection mode: Split Control mode: Pressure (Pressure: 3 kPa, Total flow rate: 16.4 mL / min, Column flow rate: 26.8 mL / min, Linear velocity: 25.1 cm sec, Purge flow rate: 0.3 mL / min, Split ratio: 5.0) Column temperature rise conditions: After holding at 100°C for 1 minute, heat to 350°C at 20.0°C / min and hold for 20 minutes.

[0079] (Calculation of triacylglyceride amount) Using the gas chromatograph detector, five samples for GC were prepared by mixing canola oil and PEG-600 in the amounts (g) shown in the table below and diluting the mixture with tetrahydrofuran (THF) to a concentration of 0.04% by mass. For each sample, the peak height (μV) of the triacylglyceride (TAG) peak was measured, and a calibration curve for the amount of triacylglyceride (mass%) was created (Figure 1).

[0080] [Table 1]

[0081] <Production of Composition> Tables 2 and 3 show the blending ratios of the raw materials used in the examples and comparative examples, and the performance of the compositions produced.

[0082] The ratio of raw materials, whether or not a reaction is carried out, and water solubility [Table 2]

[0083] About the performance of the composition [Table 3]

[0084] [Example 1] A 1-L four-neck flask was charged with 176 g of refined No. 2 oil (Tsukuno Oleochemicals Co., Ltd.) and 480 g of PEG-600 (EO type, number-average molecular weight: 600, EO / PO (number-average molecular weight ratio) = 100 / 0, Aoki Oil & Fat Industries Co., Ltd.) (molar ratio of refined No. 2 oil to PEG-600 = 1:4). The mixture was heated to 230°C under a nitrogen atmosphere while stirring at 250 rpm. After reaching 230°C, the pressure was reduced to 100-300 torr and the mixture was allowed to react until no change in the peak area of ​​triacylglycerides derived from refined No. 2 oil was observed by GC analysis, yielding the composition (solid) of Example 1. The composition of refined No. 2 oil was 11.9 wt% palmitic acid, 3.6 wt% stearic acid, 44.1 wt% oleic acid, 33.7 wt% linoleic acid, and 6.0 wt% linolenic acid.

[0085] [Example 2] The composition (solid) of Example 2 was obtained in the same manner as in Example 1, except that 88 g of refined No. 2 oil (manufactured by Tsuno Oleochemicals Co., Ltd.) and 360 g of PEG-600 (EO type, number average molecular weight: 600, EO / PO (number average molecular weight ratio) = 100 / 0, manufactured by Aoki Oil & Fat Industries Co., Ltd.) (molar ratio of refined No. 2 oil:PEG-600 = 1:6) were used.

[0086] [Example 3] The composition (solid) of Example 3 was obtained in the same manner as in Example 1, except that 168 g of refined No. 2 oil (manufactured by Tsuno Oleochemicals Co., Ltd.) and 480 g of Braunon P-106 (EO-PO-EO type, number average molecular weight: 2500, EO / PO (number average molecular weight ratio) = 60 / 40, manufactured by Aoki Oil & Fat Industries Co., Ltd.) (molar ratio of refined No. 2 oil:P-106 = 1:1) were used.

[0087] [Example 4] The composition (solid) of Example 4 was obtained in the same manner as in Example 1, except that 52.8 g of refined No. 2 oil (manufactured by Tsuno Oleochemicals Co., Ltd.) and 450 g of Brownon P-106 (EO-PO-EO type, number average molecular weight: 2500, EO / PO (number average molecular weight ratio) = 60 / 40, manufactured by Aoki Oil & Fat Industries Co., Ltd.) (molar ratio of refined No. 2 oil:P-106 = 1:3) were used.

[0088] [Example 5] The composition (solid) of Example 5 was obtained in the same manner as in Example 1, except that 53.4 g of canola oil (manufactured by Nisshin Oillio Group, Ltd.) and 450 g of Braunon P-106 (EO-PO-EO type, number average molecular weight: 2500, EO / PO (number average molecular weight ratio) = 60 / 40, manufactured by Aoki Oil & Fat Co., Ltd.) (molar ratio of canola oil:P-106 = 1:3) were used. The composition of the canola oil was 4.5 mass% palmitic acid, 1.2 mass% stearic acid, 62.9 mass% oleic acid, 21.8 mass% linoleic acid, and 9.6 mass% linolenic acid.

[0089] [Comparative Example 1] When checking the adhesion effect of the asphalt mixture, the amount of asphalt mixture adhered was checked without putting anything on the shovel (without using any anti-adhesion agent).

[0090] Comparative Example 2 The amount of asphalt mixture adhered to the scoop was checked using only water. Tests were also conducted to see how much water attacks the rubber and how well the asphalt dissolves.

[0091] Comparative Example 3 PEG-600 (EO type, number average molecular weight: 600, EO / PO (number average molecular weight ratio) = 100 / 0, manufactured by Aoki Oil & Fat Industries Co., Ltd.) was applied to a scoop to check the amount of asphalt mixture adhered. In addition, tests were conducted on the attack of PEG-600 on rubber and the solubility of asphalt.

[0092] Comparative Example 4 The performance evaluations shown in Table 4 were carried out using Tolex TR-110 (a conventional asphalt mixture anti-adhesion agent provided by Tsuno Oleochemicals, which is an anti-adhesion agent that emulsifies with water).

[0093] Comparative Example 5 A 1-L four-neck flask was charged with 176 g of refined No. 2 oil (Tsukuno Oleochemicals Co., Ltd.) and 480 g of PEG-600 (EO type, number-average molecular weight: 600, EO / PO (number-average molecular weight ratio) = 100 / 0, Aoki Oil & Fat Industries Co., Ltd.) (refined No. 2 oil:PEG-600 molar ratio = 1:4) and stirred at 250 rpm at room temperature for 1 hour (no transesterification). GC analysis confirmed that the fatty acid:triacylglyceride peak area ratio after mixing was unchanged from that after analysis of refined No. 2 oil, yielding a liquid composition of Comparative Example 5 in which refined No. 2 oil and PEG-600 had not undergone transesterification.

[0094] Comparative Example 6 The composition (liquid) of Comparative Example 6 was obtained in the same manner as in Comparative Example 5, except that 168 g of Refined No. 2 Oil (manufactured by Tsuno Oleochemicals Co., Ltd.) and 480 g of Brownon P-106 (EO-PO-EO type, number average molecular weight: 2500, EO / PO (number average molecular weight ratio) = 60 / 40, manufactured by Aoki Oil & Fat Industries Co., Ltd.) (molar ratio of Refined No. 2 Oil:P-106 = 1:1) were used.

[0095] Comparative Example 7 The composition (liquid) of Comparative Example 7 was obtained in the same manner as in Example 1, except that 440 g of refined No. 2 oil (manufactured by Tsuno Oleochemicals Co., Ltd.) and 75 g of triethylene glycol (molar ratio of refined No. 2 oil:triethylene glycol = 1:1) were used.

[0096] [Comparative Example 8] The composition (liquid) of Comparative Example 8 was obtained in the same manner as in Example 1, except that 351 g of refined No. 2 oil (manufactured by Tsuno Oleochemicals Co., Ltd.) and 180 g of triethylene glycol (molar ratio of refined No. 2 oil:triethylene glycol = 1:3) were used.

[0097] <Calculation of triacylglyceride content (mass%) in the reaction system> The fats and oils and polyalkylene glycols (PAGs) of Examples 1 to 5 and Comparative Examples 1 to 8 were mixed and diluted with THF. Note that before the reaction (reaction time 0 hours), the fats and oils and PAGs were mixed according to the charging ratios shown in the table and then diluted with THF. During and after the reaction, samples were taken from the system and then diluted with THF. GC analysis was then performed under the above conditions, and the triacylglyceride content (% by mass) in the reaction system was calculated based on the peak height of the triglyceride peak and the above calibration curve.

[0098] <Calculation of reaction rate of transesterification reaction> The triacylglyceride content before the reaction was taken as 0% reaction rate, and after 12 hours, it was confirmed that the triacylglyceride content remained unchanged, making the reaction rate 100%. The reaction rate at each reaction time point was calculated from the triacylglyceride content during the reaction.

[0099] Table 4 shows the triacylglyceride content (mass %) in the reaction system and the reaction rate in Examples 1 to 5 and Comparative Examples 1 to 8. [Table 4]

[0100] <Evaluation of each performance> The performance of the compositions obtained in the Examples and Comparative Examples shown in Tables 2 and 3 was evaluated according to the following methods.

[0101] How to check water solubility The composition and water were mixed in a 1:1 ratio (by mass), and the resulting mixture was shaken well and allowed to stand for about 5 minutes. If the mixture was uniform and transparent, it was judged to be "water soluble (◯)." If it was cloudy or the oil and water layers were separated, it was judged to be "not water soluble (×)."

[0102] How to check oil-water separation A 50% aqueous solution obtained by mixing the composition and water in a 1:1 ratio (by mass) was shaken well, and the state of separation of the oil and water layers in the aqueous solution was checked after one month. If there was no separation, it was judged as "no oil-water separation," and if there was separation, it was judged as "oil-water separation."

[0103] How to check the amount of asphalt mixture adhered A scoop was immersed in a 0.5% aqueous solution obtained by mixing the composition and water in a ratio of 0.5:99.5 (by mass), and the water was drained off 10 times. After the excess aqueous solution was removed, the scoop was inserted and removed 10 times into an asphalt mixture that had been preheated to 150°C. The weight change before and after this was measured, and the amount of asphalt mixture adhered to the scoop was determined.

[0104] How to check the attack on rubber A piece of natural rubber was placed in a 5% aqueous solution obtained by mixing the composition and water in a 5:95 ratio (by mass), and after leaving it to stand at room temperature for 3 hours, the presence or absence of swelling of the rubber piece was evaluated by determining the rate of change in mass and volume (length x width x depth). If the rate of change in volume and mass obtained in this way was less than 1%, it was rated as "not attacking" the rubber, and if either rate was 1% or more, it was rated as "attacking" the rubber.

[0105] Method for confirming the solubility of asphalt mixtures (cutback test) Pieces of asphalt mixture were placed in a 5% aqueous solution obtained by mixing the composition and water in a 5:95 ratio (by mass), and the solution was left to stand at room temperature for one week. The dissolution of the asphalt mixture was confirmed by checking for any change in the color of the liquid. If the color of the liquid did not change, the asphalt mixture was judged to be "not soluble," and if the color of the liquid changed, the asphalt mixture was judged to be "soluble."

[0106] How to check the pour point The pour points of a 5% aqueous solution obtained by mixing the composition and water in a ratio of 5:95 (mass ratio) and a 50% aqueous solution obtained by mixing the composition and water in a ratio of 50:50 (mass ratio) were measured according to JIS K-2269.

[0107] How to check stability (mgKOH / g) The composition and water were mixed in a 1:1 ratio (by mass) to prepare a 50% aqueous solution, which was then stored at 60°C for two weeks, and the increase in acid value (mgKOH / g) was measured to confirm the stability of the composition.

[0108] As is clear from the results in Table 2, the compositions of the examples are water-soluble, and their 50% aqueous solutions did not undergo oil-water separation, demonstrating excellent stability. Furthermore, as shown in Table 3, the compositions of the examples, in their 0.5% aqueous solutions, exhibited superior asphalt mixture adhesion prevention capabilities to conventional asphalt mixture anti-adhesion agents, PAG alone, and mixed compositions of PAG and an oil / fat composition that does not involve transesterification. Furthermore, the compositions of the examples, in their 5% aqueous solutions, did not attack rubber, did not dissolve asphalt mixtures, and had pour points below 0°C.

[0109] As is clear from the results of Example 1 and Comparative Example 5, Example 3 and Comparative Example 6, and Comparative Examples 7 and 8 in Table 2, a composition obtained by transesterifying an oil or fat composition with a polyalkylene glycol having a degree of polymerization of 4 or more was water-soluble by the above-mentioned method, while a mixture of the oil or fat composition and a polyalkylene glycol without transesterification, and a composition obtained by transesterifying the oil or fat composition with triethylene glycol (TEG) were not water-soluble by the above-mentioned confirmation method, and their 50% aqueous solutions underwent oil-water separation.Furthermore, with regard to the composition of Example 4 in Table 2, a mixture of the oil or fat composition and a polyalkylene glycol without transesterification was not water-soluble by the above-mentioned confirmation method, and their 50% aqueous solutions underwent oil-water separation. This reveals that simply mixing an oil or fat composition with a polyalkylene glycol does not impart stability to the resulting composition (simple mixture) in water solubility and / or oil-water separation, whereas transesterifying an oil or fat composition with a polyalkylene glycol having a degree of polymerization of 4 or more imparts stability to the resulting composition (the transesterified composition) in water solubility and / or oil-water separation.

[0110] As shown in Examples 2, 4, and 5 in Table 3, the pour points of the aqueous solutions of the compositions are lower than the freezing point of water (0°C). Furthermore, Examples 2, 4, and 5 are solid at room temperature (25°C), but become liquid at room temperature (25°C) when mixed with water. This means that when each composition is mixed with water, the composition itself becomes liquid and at the same time has a freezing point depressing effect on water, and by controlling the concentration of the composition, it has the characteristic of being usable in cold regions.

[0111] The results in Table 4 show that the ester exchange reaction time was at least 5 hours and the reaction rate was at least 85%. The results of Examples 1 and 2 and Examples 3 and 4 in Tables 2 to 4 show that even when the molar ratio of fats and oils to PAG was different, the product was similarly water-soluble and had an anti-adhesion effect on asphalt mixtures. Furthermore, the results of Examples 1 to 5 show that even when the number-average molecular weight of the PAG used in the examples and the ratio of EO to PO were different, the product was similarly water-soluble and had an anti-adhesion effect on asphalt mixtures. Therefore, although the mechanism is unclear, it is believed that a transesterification reaction product of fats and oils with a PAG having a degree of polymerization of 4 or more has an anti-adhesion effect on asphalt mixtures and is water-soluble due to the interaction of the components produced. [Industrial Applicability]

[0112] The composition of the present disclosure is useful as a composition for preventing adhesion of asphalt mixtures, etc.

Claims

1. A composition for preventing adhesion of asphalt mixtures, comprising an aqueous solution containing a composition obtained by transesterifying an oil / fat composition with a polyalkylene glycol.

2. 2. The adhesion preventive composition for asphalt mixtures according to claim 1, wherein the number average molecular weight of the polyalkylene glycol is 200 to 4,000.

3. 3. The adhesion preventive composition for asphalt mixtures according to claim 1, wherein the molar ratio of the oil composition to the polyalkylene glycol is 3:1 to 1:

9.

4. 3. The adhesion preventive composition for asphalt mixtures according to claim 1, wherein the polyalkylene glycol has an EO / PO (oxyethylene group / oxypropylene group) content ratio (number average molecular weight ratio) of 100 / 0 to 12.5 / 87.5.

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