Composition

Abstract

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

Description

Technical Field

[0001] The present disclosure relates to a composition.

Background Art

[0002] Once, mineral oil and heavy oil were used as an anti-adhesive agent for asphalt composites, but there were problems such as adverse effects on the surrounding environment, dissolution of asphalt on the pavement surface, promotion of tire deterioration, and flammability. As an anti-adhesive agent for asphalt composites having performance equivalent to or better than that of mineral oil and heavy oil, an anti-adhesive agent that is diluted with water and used has been developed. An emulsion type containing a surfactant has been developed to impart miscibility with water, but it has been necessary to contain a large amount of animal and vegetable oils and fats or terpene compounds in order to obtain a good effect. Therefore, after dilution with water, oil-water separation occurs over time in the tank, resulting in a concentration gradient, and there has been a problem that a stable effect cannot be obtained. In addition, those containing vegetable oil or fats had problems such as dissolution of asphalt, discoloration, and reduction of surface hardness. In order to solve the problem, an anti-adhesive agent for asphalt composites using a polyalkylene glycol derivative having high affinity with water and not containing an oily component has been reported, but there has been a problem that the effect is insufficient at a low concentration.

[0003] Various compositions and the like related to an anti-adhesive agent for asphalt composites are known (Patent Documents 1 to 26).

[0004] However, the above documents do not disclose the specific compositions in some embodiments of the present disclosure.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 24

Patent Document 25

Patent Document 26

Summary of the Invention

Problems to be Solved by the Invention

[0006] The problem of the present disclosure is to provide a novel composition. Preferably, the problem of the present disclosure is to provide a water-soluble composition. Preferably, the problem of the present disclosure is to provide a composition for preventing adhesion of asphalt composite materials. More preferably, the problem of the present disclosure is to provide a composition having high asphalt composite material adhesion prevention performance even at a low concentration when dissolved in water. More preferably, the problem of the present disclosure is to provide a composition for preventing adhesion of asphalt composite materials, which is excellent in safety and environmental protection, does not cause dissolution of asphalt, and causes little damage to rubber materials such as tires.

Means for Solving the Problems

[0007] As a result of intensive studies, the present inventors have found a composition having several characteristics by subjecting an oil and fat composition and a polyalkylene glycol to transesterification.

[0008] The present disclosure relates to the following inventions and the like. [1] A composition obtained by subjecting an oil and fat composition and a polyalkylene glycol to transesterification. [2] The composition according to [1] above, wherein the number average molecular weight of the polyalkylene glycol is 200 to 4000. [3] The composition according to [1] or [2] above, wherein the molar ratio of the oil and fat composition to the polyalkylene glycol is 3:1 to 1:9. [4] The composition according to any one of [1] to [3] above, wherein the EO / PO (oxyethylene group / oxypropylene group) content ratio (number average molecular weight ratio) of the polyalkylene glycol is 100 / 0 to 12.5 / 87.5. [5] An aqueous solution containing the composition according to any one of [1] to [4]. [6] A lubricating composition containing the aqueous solution of [5]. [7] The composition according to any one of [1] to [4] and [6], which is for preventing adhesion of asphalt composite materials. [8] The composition according to [1] or [2], which is water-soluble. [9] The composition according to [1] or [2], wherein the state of the mixture obtained by mixing water and the composition at a mass ratio of 1:1 under the condition of standing for 5 minutes is uniform and transparent. [Effect of the Invention]

[0009] According to the present disclosure, a novel composition can be provided. According to the present disclosure, preferably, a composition having water solubility can be provided. According to the present disclosure, preferably, a composition for preventing adhesion of asphalt composite materials can be provided. According to the present disclosure, more preferably, a composition having high asphalt composite material adhesion prevention performance even at a low concentration (for example, less than 10% by mass, less than 5% by mass, 0.5% by mass or more, etc.) when dissolved in water can be provided. According to the present disclosure, more preferably, a composition for preventing adhesion of asphalt composite materials, which is excellent in safety and environmental conservation, does not cause dissolution of asphalt, and causes little damage to rubber materials such as tires, can be provided. [Brief Description of the Drawings]

[0010] [Figure 1] The calibration curve showing the peak height (μV) of the peak of triacylglycerol (TAG) and the amount (%) of triacylglycerol measured using canola oil and PEG-600 is shown. [Embodiments for Carrying out the Invention]

[0011] [Composition] This disclosure provides a composition obtained by transesterifying an oil and fat composition with a polyalkylene glycol (for example, by mixing the oil and fat composition with the polyalkylene glycol and heating it 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 by mixing the oil and fat composition with the polyalkylene glycol and heating it at 40 to 230°C). The composition may contain several esters obtained by transesterifying the oil and fat composition with the polyalkylene glycol. The composition may contain or may not contain any other components besides the esters. The composition may also contain glycerin and / or polyalkylene glycol in addition to the esters. The composition may or may not contain a surfactant, but it is preferable that it does not contain one. However, in that case, it is preferable that the surfactant is a surfactant other than a composition obtained by transesterifying an oil and fat composition with a polyalkylene glycol. Even without containing a surfactant, the composition may have the characteristic of having high adhesion prevention performance to asphalt mixtures when dissolved in water at low concentrations (for example, less than 10% by mass, less than 5% by mass, 0.5% by mass or more, etc.). The composition may or may not contain a silicone such as dimethylpolysiloxane, but it is preferable that it does not contain one. The composition may or may not contain ether, but it is preferable that it does not contain ether.

[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, and bearing oil, or as a lubricating composition such as an asphalt mixture adhesion prevention composition. Furthermore, the metalworking oil composition can be suitably used for heavy machining, difficult machining, or machining of difficult-to-machine materials. The type of metalworking is not particularly limited, but specifically, 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. Furthermore, this disclosure includes, for example, lubricants such as metalworking agents or asphalt mixture adhesion inhibitors that contain the composition.

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

[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 be, for example, 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 a combination of the above lower and upper limits. Specifically, for example, it is preferably 1 to 35%, more preferably 1 to 25%, and even more preferably 4 to 12%. In this disclosure, where "%" is used without further explanation, it may refer to "mass%". When stearic acid is included as a fatty acid constituting the oil and fat composition used, the ratio of stearic acid to the total fatty acids constituting the oil and 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%, and the above lower and upper limits may be combined. Specifically, for example, it is preferably 0.1 to 20%, more preferably 1 to 6%, and even more preferably 1% to 4%. When oleic acid is included as a fatty acid constituting the oil and fat composition used, the ratio of oleic acid to the total fatty acids constituting the oil and fat composition used may be, for example, a lower limit of 1%, 7%, 10%, 20%, 30%, 40%, or 44%, and an upper limit of 95%, 90%, 85%, 80%, 70%, 67%, or 63%, and the above lower and upper limits may be combined. Specifically, for example, it is preferably 7-85%, more preferably 30-70%, and even more preferably 44-63%. When linoleic acid is included as a fatty acid constituting the oil and fat composition used, the ratio of linoleic acid to the total fatty acids constituting the oil and fat composition used may be, for example, a lower limit of 0.1%, 1.5%, 5%, 10%, 15%, 18%, 20%, or 21%, and 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 and fat composition used, the ratio of linolenic acid to the total fatty acids constituting the oil and fat composition used may, for example, have 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%, and the above lower and upper limits may be combined. 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 the fatty acids constituting the oil composition used include palmitic acid and stearic acid, it is preferable that the proportion of palmitic acid to the total fatty acids constituting the oil composition used is greater than that of stearic acid (for example, 2 times or more, 3 times or more, or 3.3 times or more). In one embodiment, when the fatty acids constituting the oil composition used include stearic acid and oleic acid, it is preferable that the proportion of oleic acid to the total fatty acids constituting the oil composition used is greater than that of stearic acid (for example, 10 times or more, or 12 times or more). In one embodiment, when the fatty acids constituting the oil composition used include oleic acid and linoleic acid, it is preferable that the proportion of oleic acid to the total fatty acids constituting the oil composition used is greater than that of linoleic acid (for example, 1.2 times or more, or 1.3 times or more). In one embodiment, when the fatty acids constituting the oil composition used include linoleic acid and linolenic acid, it is preferable that the proportion of linoleic acid to the total fatty acids constituting the oil composition used is greater than that of linolenic acid (for example, 2 times or more, or 2.2 times or more). In one embodiment, when the fatty acids constituting the oil composition used include palmitic acid and oleic acid, it is preferable that the proportion of oleic acid to the total fatty acids constituting the oil composition used is greater than that of palmitic acid (for example, 3 times or more, 3.5 times or more). In one embodiment, when the fatty acids constituting the oil composition used include palmitic acid and linoleic acid, it is preferable that the proportion of linoleic acid to the total fatty acids constituting the oil composition used is greater than that of palmitic acid (for example, 2 times or more, 2.5 times or more). In one embodiment, when the fatty acids constituting the oil composition used include stearic acid and linoleic acid, it is preferable that the proportion of linoleic acid to the total fatty acids constituting the oil composition used is greater than that of stearic acid (for example, 9 times or more, 9.4 times or more). In one embodiment, when the fatty acids constituting the oil composition used include stearic acid and linolenic acid, it is preferable that the proportion of linolenic acid to the total fatty acids constituting the oil composition used is greater than that of stearic acid (for example, 1.3 times or more, 1.6 times or more).In one embodiment, when the fatty acids constituting the oil composition used include oleic acid and linolenic acid, it is preferable that the proportion of oleic acid to the total fatty acids constituting the oil composition used is greater than that of linolenic acid (for example, 6 times or more, or 7 times or more). In this disclosure, where the term "proportion" is used without further context, it may refer to a "mass proportion."

[0016] In one embodiment, when the fatty acids constituting the oil composition 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) is such that, when the total fatty acids constituting the oil composition are set to 100, for example, (1~12):(0.1~3.7):(35~44.3):(20~33.9):(3~6.1), (5~12):(1~3.7):( 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) are also acceptable. The proportion of fatty acids constituting these oil and fat compositions can be calculated by hydrolysis of the oil and fat composition and then by known methods such as gas chromatography.

[0017] In one embodiment, when the fatty acids constituting the oil composition used include oleic acid and linoleic acid, it is preferable that the proportion of oleic acid to the total fatty acids constituting the oil composition used is 40-65%, and the proportion of linoleic acid is 20-40%. In one embodiment, the proportion of palmitic acid to the total fatty acids constituting the oil composition is preferably 11.9%, stearic acid is 3.6%, oleic acid is 44.1%, linoleic acid is 33.7%, and linolenic acid is 6.0% (e.g., refined oil No. 2 (manufactured by Tsukuno Oleochemicals Co., Ltd.)). In another embodiment, it is preferable that the proportion of palmitic acid to the total fatty acids constituting the oil composition used is 4.5%, the proportion of stearic acid is 1.2%, the proportion of oleic acid is 62.9%, the proportion of linoleic acid is 21.8%, and the proportion of linolenic acid is 9.6% (e.g., canola oil). The proportion of fatty acids constituting these oil and fat compositions can be calculated by hydrolysis of the oil and fat composition and then by known methods such as gas chromatography. Furthermore, by appropriately combining preferred proportions of these various fatty acids, a preferred range of fatty acid composition can be applied to the oil and fat composition being used.

[0018] (Specific examples of fat and oil compositions) In this 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 oil No. 2 (manufactured by Tsukuno Oleochemicals Co., Ltd.). These edible vegetable oils, waste cooking oil, and refined oil No. 2 may be used individually or mixed in any proportion.

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

[0020] In this disclosure, the copolymerization method of polyalkylene glycol may be either random polymerization and / or block polymerization. In this disclosure, polyalkylene glycol may be polyalkylene glycol obtained by addition polymerization of alkylene oxide. Polyalkylene glycol obtained by addition polymerization of alkylene oxide may be either random or block copolymer, but block copolymer is preferred. Examples of block polymerization types of polyalkylene glycol obtained by addition polymerization of alkylene oxide include diblock copolymer, triblock copolymer, tetrablock copolymer, and the like.

[0021] Examples of polyalkylene glycols obtained by addition polymerization of alkylene oxides include polyethylene glycol obtained by addition polymerization of ethylene oxide (EO) and polypropylene glycol obtained by addition polymerization of propylene oxide (PO). Polypropylene glycol obtained by addition polymerization of ethylene oxide (EO) can be described as, for example, polyoxyethylene polyoxypropylene block polymer, a block copolymer of ethylene oxide (EO) and propylene oxide (PO), or a Pluronic® 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. 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 a random copolymer. 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, as well as Brownon P-106 (manufactured by Aoki Oil & Fat Industry Co., Ltd.).

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

[0023] (Number average molecular weight of polyalkylene glycol) The number-average molecular weight of polyalkylene glycol may be, for example, 200 to 10000, 200 to 4000, 400 to 4000, 600 to 3500, 600 to 2500, 600 to 1900, or 2400 to 3500.

[0024] (Preferred combination of type and number-average molecular weight) When 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 but 1000 or less. When the polyalkylene glycol is an EO-PO-EO block copolymer, the number average molecular weight may be 4000 or less, less than 4000, greater than 2400 and less than or equal to 2500, greater than or equal to 2400 and less than or equal to 3500, or greater than or equal to 2500 and less than or equal to 3100.

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

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

[0027] (Preferred combinations of the molar ratio of the oil / fat composition to the polyalkylene glycol and the number-average molecular weight of the polyalkylene glycol in the transesterification reaction) When the molar ratio of the oil 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 to 2500, 2400 to less than 4000, or 2500 to 4000. When the molar ratio of the oil 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 to 2500, 2400 to less than 4000, or 2500 to 4000.

[0028] (Ingredients contained in the composition) The composition may include, for example, two or more components selected from glycerin (hereinafter also referred to as "GOL"), monoacylglycerides (hereinafter also referred to as "MAG"), diacylglycerides (hereinafter also referred to as "DAG"), triacylglycerides (hereinafter also referred to as "TAG"), polyalkylene glycols (hereinafter also referred to as "PAG"), monoesters of polyalkylene glycols (hereinafter also referred to as "ME"), and diesters of polyalkylene glycols (hereinafter also referred to as "DE"). Preferably, the composition in this disclosure may contain, for example, all of the above seven components; the above seven components excluding GOL (six components: MAG, DAG, TAG, PAG, ME, and DE); the above components excluding TAG (six components: GOL, MAG, DAG, PAG, ME, and DE); etc. The composition in this disclosure may contain one or more of each of the above components.

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

[0030] The proportion of monoacylglycerides (MAGs) to the total composition in this 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) to the total composition in this disclosure may be 1 to 30 mol%, 1 to 6 mol%, or 6 to 30 mol%.

[0032] The proportion of triacylglycerides (TAGs) to the total composition in this disclosure may be 0 to 5% by mass, or 0.1 to 5% by mass.

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

[0034] The proportion of polyalkylene glycol monoester (ME) to the total composition in this disclosure may be 25 to 40 mol%, 29 to 38 mol%, or 30 to 38 mol%.

[0035] The proportion of polyalkylene glycol diester (DE) to the total composition in this disclosure 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 compositions of this 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 compositions of this 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 compositions of this 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 compositions of this 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 compositions of this 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 compositions of this disclosure may be (0-7):(2-20), (0-6):(2-15), or (6-7):(2-7).

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

[0043] (water soluble) In some embodiments of this disclosure, the compositions herein are water-soluble. In some embodiments, this disclosure provides aqueous solutions containing the compositions herein. In some embodiments, the water solubility of the compositions herein may occur after a certain period of time has elapsed since the start of the transesterification reaction between the oil and fat composition and the polyalkylene glycol (for example, 4 hours, 5 hours, 6 hours, 7 hours, etc., from the start of the reaction). Compositions that become water-soluble after the above-mentioned period of time may maintain their water solubility thereafter. Before the start of the transesterification reaction (i.e., in the state of a simple mixture of oil and fat composition and polyalkylene glycol without transesterification), the compositions are not water-soluble. In some embodiments of this disclosure, the commencement of the transesterification reaction means the point in time when the transesterification step begins. In this step, the oil composition and polyalkylene glycol are mixed, and a catalyst (e.g., titanium alkoxy, sodium methoxide, p-toluenesulfonic acid, sodium hydroxide, enzyme, etc.) may be added as needed, or there may be no catalyst, and the mixture is heated (e.g., 40-230°C, etc.) to carry out the transesterification reaction.

[0044] How to confirm water solubility For example, a mixture obtained by mixing the composition with water in a 1:1 ratio (by mass) is shaken well and allowed to stand for about 5 minutes. If the mixture is uniform and transparent, it can be determined to be "water-soluble (○)". If it is cloudy or the oil layer and water layer separate, it can be determined to be "not water-soluble (×)". In some embodiments of this disclosure, a composition is provided in which the mixture obtained by mixing water and the composition in a 1:1 mass ratio is uniform and transparent under conditions of standing for 5 minutes.

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

[0046] Method for confirming oil-water separation For example, a 50% aqueous solution obtained by mixing the composition with water in a 1:1 ratio (by mass) can be shaken well, and after one month, the state of separation between the oil layer and the water layer in the aqueous solution can be checked. If they are not separated, it can be determined that "oil-water separation does not occur," and if they are separated, it can be determined that "oil-water separation occurs."

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

[0048] Method for checking the amount of asphalt mixture adhering to the surface For example, a shovel immersed in a 0.5% aqueous solution obtained by mixing the composition and water in a ratio of 0.5:99.5 (by mass ratio) is drained 10 times to remove excess aqueous solution. Then, the shovel is inserted and removed 10 times into asphalt mixture preheated to 150°C, and the change in weight before and after is measured to determine the amount of asphalt mixture adhered. If the amount of asphalt mixture adhered determined in this way is less than the amount of asphalt mixture adhered when the composition is replaced with a conventional asphalt mixture adhesion inhibitor (for example, TR-110 (product name) manufactured by Tsukuno Oleochemicals Co., Ltd.), then it can be determined that the composition exhibits an excellent effect in preventing adhesion of asphalt mixture.

[0049] (Attack on rubber) In some embodiments of this disclosure, the compositions present herein are non-attacking (e.g., non-damaging) to rubber. Compositions that are non-attacking to rubber do not cause deterioration of rubber even when in contact with it.

[0050] Method for confirming rubber attack properties For example, a natural rubber piece can be placed in a 5% aqueous solution obtained by mixing the composition with water in a 5:95 ratio (by mass), left to stand at room temperature for 3 hours, and then the presence or absence of swelling of the rubber piece can be evaluated by determining the rate of change in mass and volume (length × width × depth). If the rate of change in volume or mass obtained in this way is less than 1%, for example, it can be judged that there is "no" rubber attack, and if either one is 1% or more, it can be judged that there is "a" rubber attack.

[0051] (Solubility of asphalt mixture) In some embodiments of this disclosure, the compositions present herein are insoluble in asphalt mixtures. Even when an insoluble composition is brought into contact with an asphalt mixture, there is no concern that it will dissolve the asphalt mixture.

[0052] Method for confirming the solubility of asphalt mixture (cutback test) For example, by mixing the composition with water in a 5:95 ratio (by mass) to obtain a 5% aqueous solution, adding a piece of asphalt mixture, and letting it stand at room temperature for one week, the presence or absence of a change in the liquid color can be checked (visually) to confirm whether the asphalt mixture has dissolved. For example, if the liquid color does not change, it can be determined that the asphalt mixture is "not" soluble, and if the liquid color changes, it can be determined that the asphalt mixture is "soluble".

[0053] (Pour point) In some embodiments of this disclosure, the compositions of this disclosure have a pour point below freezing point, preferably -5°C or below. Such compositions are less likely to solidify, especially in winter, and do not require heating equipment, thus leading to increased work efficiency in the use of asphalt mixtures and such compositions.

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

[0055] (stability) In some embodiments of this disclosure, the compositions present herein exhibit excellent stability. This stability may be storage stability or stability against high temperatures (e.g., 30°C or above, 60°C or above).

[0056] How to check stability (mgKOH / g) For example, the stability of a composition can be confirmed by mixing the composition with water in a 1:1 ratio (by mass) to obtain a 50% aqueous solution, storing it 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 is considered to be. 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 compositions in this disclosure may contain additives. Examples of known additives include 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., Aclov 132, Aclov 146, etc.).

[0058] If the composition in this disclosure contains an additive, the upper limit of the additive content is preferably 30% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less, relative to the entire composition.

[0059] The compositions in this disclosure may be substantially free of additives and consist substantially of transesterification products (for example, five or more products selected from the group consisting of GOL, MAG, DAG, TAG, PAG, ME, and DE). "Substantially free of additives" means, for example, that the total content of additives is less than 5% by mass. "Substantially consisting of transesterification products" means, for example, that the content of transesterification products is 95% by mass or more. Furthermore, the compositions in this disclosure also include cases in which products of transesterification reactions (for example, five or more products selected from the group consisting of GOL, MAG, DAG, TAG, PAG, ME, and DE) are included without substantially involving transesterification reactions (for example, a composition made by mixing five or more components selected from the group consisting of GOL, MAG, DAG, TAG, PAG, ME, and DE).

[0060] [Method for producing the composition] The compositions in this disclosure can be produced, for example, by a manufacturing method that includes a transesterification step of transesterifying an oil and fat composition with a polyalkylene glycol.

[0061] The method for producing the composition may further include a step of removing low-boiling-point components from the ester obtained after the transesterification step to obtain a crude esterified product (hereinafter also referred to as the "low-boiling-point component removal step"), or a step of treating the crude esterified product obtained after the low-boiling-point component removal step with a treatment agent (hereinafter also referred to as the "treatment step"). The following describes each step.

[0062] (Transesterification process) In this process, the oil and fat composition is mixed with polyalkylene glycol, and a catalyst (e.g., titanium alkoxy, sodium methoxide, p-toluenesulfonic acid, sodium hydroxide, enzyme, etc.) may be added as needed, or it may be done without a catalyst, and the mixture is heated (e.g., 40-230°C, etc.) to carry out the transesterification reaction.

[0063] The equivalent ratio of the polyalkylene glycol component to the oil and fat composition component is preferably 0.1 to 2.0 moles of carboxyl groups in the oil and fat composition component per mole of hydroxyl groups in the polyalkylene glycol component, more preferably 0.2 to 1.7 moles, and particularly preferably 0.25 to 1.5 moles, from the viewpoint of production efficiency and economics. 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 catalysts include metal catalysts, acid catalysts, and base catalysts. Specifically, examples include acid catalysts such as sulfuric acid, methanesulfonic acid, and p-toluenesulfonic 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, relative to the total amount of the polyalkylene glycol component and the oil and 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 also 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, 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 reduced pressure is preferable 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 higher, preferably 10 Torr or higher, and more preferably 100 Torr or higher. The upper limit of the pressure under reduced pressure is, for example, 400 Torr or lower, preferably 300 Torr or lower.

[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. 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] Transesterification reactions are preferably carried out while measuring the composition of the reaction solution by GC, for example. The endpoint of the transesterification reaction can be confirmed by GC measurement, for example. For example, by tracking the decrease in the triacylglyceride peak of the oil composition from the GC analysis of the reaction solution, it can be considered that all of the oil composition has been used in the transesterification reaction when the peak area (height) stops changing (for example, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 12 hours, etc., from the start of the reaction).

[0069] The compositions in this disclosure and mixtures of simple oil and fat compositions and polyalkylene glycols without transesterification can be distinguished by GC measurement, based on the difference in the peak area (height) of triacylglycerides. In GC measurement, the solid content concentration in the analytical sample is kept constant. Solid content refers to the compositions in this disclosure, or mixtures of oil and fat compositions and polyalkylene glycols, and can be analyzed after dilution to 0.04% by mass with a solvent such as THF. In some embodiments, when comparing the peak area (height) of the compositions in this disclosure and mixtures of simple oil and fat compositions and polyalkylene glycols without transesterification, the peak area (height) of the former is smaller.

[0070] As described above, in some embodiments of this disclosure, the compositions of this disclosure are water-soluble. The water solubility of the compositions of this disclosure may be present, for example, before the point at which the peak area (height) of the triacylglyceride stops changing in GC measurement (for example, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 12 hours, etc. from the start of the reaction) (for example, 4 hours, 5 hours, 6 hours, 7 hours, etc. from the start of the reaction). Furthermore, the water solubility of the compositions of this disclosure may be present, for example, when the peak area (height) of the triacylglyceride before the transesterification reaction is set to a reaction rate of 0%, and the peak area (height) of the triacylglyceride at the point at which the peak area (height) stops changing (for example, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 12 hours, etc. from the start of the reaction) is set to 100%, and 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. Furthermore, the water solubility of the compositions in this disclosure may be achieved, for example, after 5 hours or more have elapsed since the start of the transesterification reaction (e.g., after 5 hours, 6 hours, 7 hours). The conditions for achieving water solubility may be obtained individually or in combination. Specifically, for example, the reaction rate may be water-soluble if the reaction rate is 94.5% or higher after 6 hours from the start of the transesterification reaction, 93.4% or higher after 5 hours from the start of the transesterification reaction, 90.9% or higher after 5 hours from the start of the transesterification reaction, 95.8% or higher after 5 hours from the start of the transesterification reaction, 91.8% or higher after 5 hours from the start of the transesterification reaction, etc. In some embodiments of the present disclosure, the compositions of the present disclosure may have reaction rates 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 steps) In this step, the obtained esterified crude product is treated with a treatment agent.

[0072] Examples of treatment agents include activated carbon and activated clay. The amount of treatment agent used is typically 0.01 to 5% by mass, and preferably 0.1 to 1% by mass, relative to the esterified crude material.

[0073] One possible treatment method is to add the treatment agent to the esterified crude product, stir at 50°C to 100°C for about 10 minutes to 2 hours, then stir under reduced pressure for about 10 minutes to 2 hours, and finally filter off the treatment agent.

[0074] In this disclosure, the term “degree” is used with the intention of including, for example, slight deviations. Such ranges also include those within the experimental error specific to the standard method used to measure and / or quantify a given value or range.

[0075] This disclosure includes, to the extent that it is effective, various combinations of the above-described configurations within the technical scope of this disclosure. [Examples]

[0076] Next, some embodiments of the present disclosure will be described in more detail by reference to examples, but the embodiments of the present disclosure are not limited in any way by these examples, and many modifications are possible within the technical concept of the present disclosure by those who are ordinary skill in the art.

[0077] (Experimental conditions) The following raw materials and measuring instruments were used in the experiment. In this example, unless otherwise specified, commercially available raw materials, equipment, measuring instruments, etc. were used.

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

[0079] (Calculation of the amount of triacylglycerides) Using the gas chromatograph detector described above, five samples for GC were prepared by mixing canola oil and PEG-600 in the weights (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 (mass%) of triacylglyceride was created (Figure 1).

[0080] [Table 1]

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

[0082] Regarding the mixing ratio of raw materials, whether or not the reaction was carried out, and water solubility. [Table 2]

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

[0084] [Example 1] 176 g of refined oil No. 2 (manufactured by 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, manufactured by Aoki Oil & Fat Industry Co., Ltd.) were placed in a 1 L four-necked flask (molar ratio of refined oil No. 2 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 reacted until no change in the peak area of ​​triacylglycerides derived from refined oil No. 2 was observed by GC analysis, yielding the composition (solid) of Example 1. The composition of refined oil No. 2 was 11.9% by mass of palmitic acid, 3.6% by mass of stearic acid, 44.1% by mass of oleic acid, 33.7% by mass of linoleic acid, and 6.0% by mass of 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 oil No. 2 (manufactured by Tsukuno 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 Industry Co., Ltd.) were used (molar ratio of refined oil No. 2 to PEG-600 = 1:6).

[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 oil No. 2 (manufactured by Tsukuno 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 Industry Co., Ltd.) were used (molar ratio of refined oil No. 2 to P-106 = 1:1).

[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 oil No. 2 (manufactured by Tsukuno 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 Industry Co., Ltd.) were used (molar ratio of refined oil No. 2 to P-106 = 1:3).

[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 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 Industry Co., Ltd.) were used (molar ratio of canola oil to P-106 = 1:3). The composition of the canola oil was 4.5% by mass of palmitic acid, 1.2% by mass of stearic acid, 62.9% by mass of oleic acid, 21.8% by mass of linoleic acid, and 9.6% by mass of linolenic acid.

[0089] [Comparative Example 1] When checking the adhesion effect of the asphalt mixture, the amount of asphalt mixture adhering was checked without applying anything to the shovel (without using an adhesion inhibitor).

[0090] [Comparative Example 2] We tested the amount of asphalt mixture adhering to a shovel dipped only in water. We also conducted tests on the water's ability to attack rubber and the solubility of the asphalt.

[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 Industry Co., Ltd.) was applied to a shovel to check the amount of asphalt mixture it adhered to. In addition, tests were conducted on the rubber-attacking properties of PEG-600 and the solubility of asphalt.

[0092] [Comparative Example 4] The performance evaluation shown in Table 4 was performed using Torex TR-110 (a conventional asphalt mixture adhesion inhibitor provided by Tsukuno Oleochemicals, which is an adhesion inhibitor that emulsifies with water).

[0093] [Comparative Example 5] 176 g of refined No. 2 oil (manufactured by 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, manufactured by Aoki Oil & Fat Industry Co., Ltd.) were placed in a 1 L four-necked flask (molar ratio of refined No. 2 oil to PEG-600 = 1:4), and the mixture was stirred at 250 rpm for 1 hour at room temperature (no transesterification reaction occurred). GC analysis confirmed that the peak area ratio of fatty acids to triacylglycerides after mixing remained unchanged compared to when the refined No. 2 oil was analyzed, thus obtaining the composition (liquid) of Comparative Example 5, in which refined No. 2 oil and PEG-600 had not undergone transesterification.

[0094] [Comparative Example 6] A composition (liquid) for Comparative Example 6 was obtained in the same manner as for Comparative Example 5, except that 168 g of refined oil No. 2 (manufactured by Tsukuno 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 Industry Co., Ltd.) were used (molar ratio of refined oil No. 2 to P-106 = 1:1).

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

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

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

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

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

[0100] <Evaluation of each performance aspect> The performance of each composition obtained in the examples and comparative examples shown in Tables 2 and 3 was determined according to the following method.

[0101] How to confirm 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 separated, it was judged to be "not water-soluble (×)".

[0102] Method for confirming oil-water separation A 50% aqueous solution was obtained by mixing the composition with water in a 1:1 ratio (by mass), and the mixture was shaken well. After one month, the state of separation between the oil layer and the water layer in the aqueous solution was checked. If separation did not occur, it was judged as "no oil-water separation," and if separation occurred, it was judged as "oil-water separation occurred."

[0103] Method for checking the amount of asphalt mixture adhering to the surface A shovel immersed in a 0.5% aqueous solution obtained by mixing the composition with water in a ratio of 0.5:99.5 (by mass) was drained 10 times to remove excess aqueous solution, and then the shovel was inserted and removed 10 times into asphalt mixture that had been preheated to 150°C. The change in weight before and after this was measured to determine the amount of asphalt mixture that adhered to the shovel.

[0104] Method for confirming rubber attack properties A 5% aqueous solution was obtained by mixing the composition with water in a 5:95 ratio (by mass), and a piece of natural rubber was placed in it. After standing at room temperature for 3 hours, the rubber-attacking ability was evaluated by determining whether or not the rubber piece swelled and by calculating the rate of change in mass and volume (length × width × depth). If the rate of change in volume and mass obtained in this way was less than 1%, the rubber-attacking ability was evaluated as "absent," and if either of them was 1% or more, the rubber-attacking ability was evaluated as "present."

[0105] Method for confirming the solubility of asphalt mixture (cutback test) A 5% aqueous solution was obtained by mixing the composition with water in a 5:95 ratio (by mass). Fragments of asphalt mixture were placed in this solution and left to stand at room temperature for one week. The presence or absence of a change in the liquid color was then checked to confirm whether the asphalt mixture had dissolved. If the liquid color did not change, it was determined that the asphalt mixture was not soluble; if the liquid color changed, it was determined that the asphalt mixture was soluble.

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

[0107] How to check stability (mgKOH / g) The stability of the composition was confirmed by measuring the increase in acid value (mgKOH / g) after storing a 50% aqueous solution obtained by mixing the composition with water in a 1:1 ratio (by mass) at 60°C for two weeks.

[0108] As is clear from the results in Table 2, the composition of the example was water-soluble, its 50% aqueous solution did not separate oil and water, and showed excellent stability. Furthermore, as shown in Table 3, the composition of the example, in its 0.5% aqueous solution, showed superior anti-adhesion function for asphalt mixtures compared to conventional anti-adhesion agents, PAG alone, and mixed compositions of oil and fat compositions and PAG without transesterification. Moreover, in its 5% aqueous solution, the composition of the example did not attack rubber, did not dissolve asphalt mixtures, and had a pour point of 0°C or lower.

[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, the composition obtained by transesterifying the oil and fat composition with a polyalkylene glycol having a degree of polymerization of 4 or higher showed water solubility using the method described above. On the other hand, the mixture obtained by mixing the oil and fat composition with polyalkylene glycol without transesterification, and the composition obtained by transesterifying the oil and fat composition with triethylene glycol (TEG), did not have water solubility using the method described above, and their 50% aqueous solutions underwent oil-water separation. Furthermore, regarding the composition of Example 4 in Table 2, the mixture obtained by mixing the oil and fat composition with polyalkylene glycol without transesterification did not have water solubility using the method described above, and its 50% aqueous solution underwent oil-water separation. From this, it became clear that simply mixing an oil and fat composition with polyalkylene glycol does not impart water solubility and / or stability against oil-water separation to the resulting composition (a mere mixture), while transesterifying the oil and fat composition with a polyalkylene glycol having a degree of polymerization of 4 or higher imparts water solubility and / or stability against oil-water separation to the resulting composition (a transesterified composition).

[0110] As shown in Examples 2, 4, and 5 of Table 3, the pour point of the aqueous solution of the composition is lower than the freezing point of water (0°C). Furthermore, although Examples 2, 4, and 5 are solids at room temperature (25°C), they become liquids at room temperature (25°C) when mixed with water. This means that when each composition is mixed with water, the composition itself becomes liquefied and at the same time has a freezing point depression effect on water, and by controlling the concentration of the composition, it can be used even in cold regions.

[0111] The results in Table 4 show that the solution became water-soluble after at least 5 hours of transesterification. Furthermore, the reaction rate at that point was at least 85%. From the results of Examples 1 and 2, and Examples 3 and 4 in Tables 2-4, it was found that even when the molar ratio of oil and PAG differed, the mixture remained water-soluble and exhibited an anti-adhesion effect on asphalt mixtures. Furthermore, from the results of Examples 1-5, it was found that even when the number-average molecular weight of the PAG used in the examples differed, or when the ratio of EO to PO differed, the mixture remained water-soluble and exhibited an anti-adhesion effect on asphalt mixtures. Therefore, although the mechanism is not clear, it is thought that if the transesterification reaction product is of oil and PAG with a degree of polymerization of 4 or higher, the interaction of the resulting components results in an anti-adhesion effect on asphalt mixtures and water solubility. [Industrial applicability]

[0112] The compositions disclosed herein are useful as compositions for preventing adhesion of asphalt mixtures, etc.

Claims

1. A composition obtained by transesterifying an oil and fat composition with a polyalkylene glycol.

2. The composition according to claim 1, wherein the number-average molecular weight of the polyalkylene glycol is 200 to 4000.

3. The composition according to claim 1 or 2, wherein the molar ratio of the oil and fat composition to the polyalkylene glycol is 3:1 to 1:

9.

4. The composition according to claim 1 or 2, wherein the EO / PO (oxyethylene group / oxypropylene group) content ratio (number average molecular weight ratio) of the polyalkylene glycol is 100 / 0 to 12.5 / 87.

5.

5. An aqueous solution comprising the composition described in claim 1.

6. A lubricating composition comprising the aqueous solution of claim 5.

7. The composition according to claim 1 or 2, which is water-soluble.

8. The composition according to claim 1 or 2, wherein the mixture obtained by mixing water and the composition in a 1:1 mass ratio is uniform and transparent when left to stand for 5 minutes.

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