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 reacting a fatty acid, including a fatty acid having 18 carbon atoms, 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 reacting a fatty acid, including a fatty acid having 18 carbon atoms, with a polyalkylene glycol.

[0008] The present disclosure relates to the following inventions, etc. [1] A composition obtained by reacting a fatty acid containing a fatty acid having 18 carbon atoms 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 the above [1] or [2], wherein the molar ratio of the fatty acid containing a fatty acid having 18 carbon atoms 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] The composition according to any one of the above [1] to [4], which is obtained by reacting a fatty acid containing a fatty acid having 18 carbon atoms, a polyalkylene glycol, and glycerin. [6] An aqueous solution containing the composition according to any one of [1] to [5] above. [7] A lubricating composition comprising the aqueous solution according to [6] above. [8] The composition according to any one of [1] to [5] and [7], which is used to prevent adhesion of asphalt mixtures. [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. DETAILED DESCRIPTION OF THE INVENTION

[0010] <Composition> The present disclosure provides a composition obtained by reacting (e.g., esterification, transesterification, etc.) a fatty acid containing 18 carbon atoms with a polyalkylene glycol (e.g., by mixing a mixed fatty acid containing 18 carbon atoms with a polyalkylene glycol, heating under a nitrogen atmosphere at a temperature above room temperature, e.g., 40 to 250°C, and draining the produced water out of the system under atmospheric or reduced pressure). The composition may contain several esters obtained by reacting (e.g., esterification, transesterification, etc.) a fatty acid containing 18 carbon atoms with a polyalkylene glycol. The composition may also be obtained by reacting (e.g., esterification, transesterification, etc.) glycerin in addition to a fatty acid containing 18 carbon atoms and a polyalkylene glycol. The composition may be obtained by esterification and transesterification of a fatty acid containing 18 carbon atoms, a polyalkylene glycol, and glycerin, or may be obtained by at least an esterification reaction. The composition may or may not contain optional components other than the esters. In addition to the ester, the composition may contain glycerin and / or polyalkylene glycol. 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 reacting a fatty acid, including a fatty acid having 18 carbon atoms, with a polyalkylene glycol. Even if the composition does not contain a surfactant, it can be characterized by 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. In the present disclosure, "resulting from a reaction" includes, for example, reactions such as an esterification reaction, a transesterification reaction, etc. Furthermore, in the present disclosure, when the word "reaction" is simply written, it may refer to an "esterification reaction" and / or a "transesterification reaction."

[0011] 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.

[0012] <Fatty acids containing 18 carbon atoms> The fatty acid used is a fatty acid containing 18 carbon atoms. The fatty acid used may be a free fatty acid. The "fatty acid containing 18 carbon atoms" may be a single type of fatty acid or a fatty acid (mixed fatty acid) composed of multiple types of fatty acids. The "fatty acid containing 18 carbon atoms" may be a fatty acid consisting only of 18 carbon atoms, or may contain fatty acids other than 18 carbon atoms. The "fatty acid containing 18 carbon atoms" may contain at least one 18 carbon atom fatty acid, or may contain one or more (e.g., two, three, four, etc.) 18 carbon atom fatty acids. The 18 carbon atom fatty acid may be a saturated fatty acid, an unsaturated fatty acid, or a mixture of both. Furthermore, it may be a straight-chain fatty acid, a branched-chain fatty acid, or a mixture of both. Specific examples include stearic acid, isostearic acid, oleic acid, linoleic acid, and linolenic acid. Examples of fatty acids other than those having 18 carbon atoms include linear unsaturated fatty acids having 12 to 17 or 19 to 22 carbon atoms; linear saturated fatty acids having 12 to 17 or 19 to 22 carbon atoms (lauric acid, myristic acid, palmitic acid, arachidic acid, behenic acid, etc.); branched saturated fatty acids having 12 to 17 or 19 to 22 carbon atoms (2,2-dimethyloctanoic acid, 3-methylbutanoic acid, etc.); branched unsaturated fatty acids having 12 to 17 or 19 to 22 carbon atoms, and may contain various other fatty acids or combinations thereof. The mixed fatty acid may contain, for example, at least oleic acid.

[0013] (Composition of fatty acids used) When palmitic acid is included as a constituent fatty acid of the fatty acid used, the ratio of palmitic acid to the total fatty acids constituting the fatty acid used may be, for example, a lower limit of 0.01%, 0.1%, 0.3%, 0.5%, 1.0%, 1.1%, or 1.5%, and an upper limit of 50%, 40%, 35%, 30%, 25%, 20%, 15%, 12%, 10%, 5.5%, 5.0%, or 3.0%, or a combination of the above lower and upper limits. Specifically, it may be, for example, 0.1 to 35%, 0.5 to 25%, or 1 to 12%. In the present disclosure, when simply "%" is used, it may be "% by mass." When stearic acid is included as a constituent fatty acid of the fatty acid used, the ratio of stearic acid to the total fatty acids constituting the fatty acid used may be, for example, a lower limit of 0.01%, 0.1%, 0.5%, 1.0%, 1.2%, 1.5%, 1.7%, 2.0%, 3.0%, or 3.2%, and an upper limit of 30%, 20%, 10%, 6.0%, 5.0%, 4.5%, 4.0%, 3.7%, or 3.6%, or a combination of the above lower and upper limits. Specifically, it may be, for example, 0.1 to 20%, 1 to 6%, or 1 to 4.5%. When oleic acid is included as a fatty acid constituting the fatty acid used, the ratio of oleic acid to the total fatty acids constituting the fatty acid used may be, for example, 1%, 7%, 10%, 20%, 30%, 34%, 40%, 44%, 50%, 52%, or 54% as a lower limit, or 100% as an upper limit, or 90%, 85%, 81%, 80%, 70%, 67%, or 63%, or a combination of the above lower and upper limits. Specifically, it may be, for example, 7 to 100%, 30 to 100%, or 34 to 100%. When linoleic acid is included as a constituent fatty acid of the fatty acid used, the ratio of linoleic acid to the total fatty acids constituting the fatty acid used may be, for example, 0.1%, 1.5%, 5%, 10%, 11%, 15%, 18%, 20%, 21%, 33%, or 36% as a lower limit, or 70%, 60%, 56%, 55%, 50%, 40%, or 37% as an upper limit, or a combination of the above lower and upper limits. Specifically, it may be, for example, 1.5 to 70%, 5 to 60%, or 10 to 40%. When linolenic acid is included as a constituent fatty acid of the fatty acid used, the ratio of linolenic acid to the total fatty acids constituting the fatty acid used may be, for example, a lower limit of 0.01%, 0.1%, 1.0%, 3%, 4%, or 5%, and an upper limit of 65%, 50%, 40%, 30%, 20%, 13%, 10%, 9.8%, or 9.6%, or a combination of the above lower and upper limits. Specifically, it may be, for example, 0.01 to 65%, 3 to 20%, or 4 to 13%.

[0014] In one embodiment, when the fatty acids constituting the fatty acids used include palmitic acid and stearic acid, the ratio of stearic acid to the total fatty acids constituting the fatty acids used may be greater than that of palmitic acid (e.g., 1.5 times or more, 2 times or more, 2.5 times or more, 2.9 times or more). In one embodiment, when the fatty acids constituting the fatty acids used include stearic acid and oleic acid, the ratio of oleic acid to the total fatty acids constituting the fatty acids used may be greater than that of stearic acid (e.g., 10 times or more, 15 times or more, 16 times or more). In one embodiment, when the fatty acids constituting the fatty acids used include oleic acid and linoleic acid, the ratio of oleic acid to the total fatty acids constituting the fatty acids used may be greater than that of linoleic acid (e.g., 1.2 times or more, 1.4 times or more). In one embodiment, when the fatty acids constituting the fatty acids used include linoleic acid and linolenic acid, the ratio of linoleic acid to the total fatty acids constituting the fatty acids used may be greater than that of linolenic acid (e.g., 4 times or more, 5 times or more, 7 times or more). In one embodiment, when the fatty acids constituting the fatty acids used include palmitic acid and oleic acid, the ratio of oleic acid to the total fatty acids constituting the fatty acids used may be greater than that of palmitic acid (e.g., 15 times or more, 30 times or more, 40 times or more, 45 times or more). In one embodiment, when the fatty acids constituting the fatty acids used include palmitic acid and linoleic acid, the ratio of linoleic acid to the total fatty acids constituting the fatty acids used may be greater than that of palmitic acid (e.g., 2 times or more, 15 times or more, 20 times or more, 30 times or more). In one embodiment, when the fatty acids constituting the fatty acids used include stearic acid and linoleic acid, the ratio of linoleic acid to the total fatty acids constituting the fatty acids used may be greater than that of stearic acid (e.g., 6 times or more, 8 times or more, 10 times or more). In one embodiment, when the fatty acids constituting the fatty acids used include stearic acid and linolenic acid, the ratio of linolenic acid to the total fatty acids constituting the fatty acids used may be greater 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 fatty acid used include oleic acid and linolenic acid, the ratio of oleic acid to the total fatty acids constituting the fatty acid used may be greater than that of linolenic acid (e.g., 3 times or more, 6 times or more, 10 times or more). In the present disclosure, when the term "ratio" is used, it may be "mass ratio."

[0015] In one embodiment, when the fatty acids constituting the fatty acid used 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, when the total fatty acids constituting the fatty acid is taken as 100, for example, (0.01 to 50):(0.01 to 30):(1 to 100):(0.1 to 70):(0 to 65), (0.1 to 40):(0 .1~20):(7~100):(1.5~60):(0.01~50), (0.3~35):(0.5~10):(10~100):(5~55):(0.1~40), (0.5~30):(1~6):(20~100):(10~50):(1~13), (1~25):(2~5):(30~100):(15~40):(3~20), (1.1~20):(3.2~4.5):(52~100):(33~37):(5.1~10). The proportion of these fatty acids constituting the fatty acids can be calculated by analyzing the fatty acids by a known method such as gas chromatography.

[0016] In one embodiment, when the fatty acids constituting the fatty acid used include oleic acid and linoleic acid, the proportion of oleic acid to the total fatty acids constituting the fatty acid used may be 30 to 85%, and the proportion of linoleic acid may be 10 to 60%. In one embodiment, the fatty acid used preferably contains 1.1% palmitic acid, 3.2% stearic acid, 52.4% oleic acid, 36% linoleic acid, and 5.1% linolenic acid relative to the total fatty acids (e.g., TFA-125 (manufactured by Tsuno Oleochemicals Co., Ltd.)). In another embodiment, the proportion of palmitic acid relative to the total fatty acids constituting the fatty acids used is preferably 1.5%, stearic acid 3.7%, oleic acid 54.5%, linoleic acid 33.3%, and linolenic acid 7.0%. In another embodiment, it is preferred that the proportion of palmitic acid relative to the total fatty acids constituting the fatty acids used is 1.0%, the proportion of stearic acid is 1.5%, the proportion of oleic acid is 34.3%, the proportion of linoleic acid is 56.1%, and the proportion of linolenic acid is 7.1%. In another embodiment, it is preferred that the proportion of palmitic acid relative to the total fatty acids constituting the fatty acids used is 5.5%, the proportion of stearic acid is 1.7%, the proportion of oleic acid is 81.6%, the proportion of linoleic acid is 11.2%, and the proportion of linolenic acid is 0%. In another embodiment, it is preferred that the proportion of palmitic acid relative to the total fatty acids constituting the fatty acids used is 3.0%, the proportion of stearic acid is 4.5%, the proportion of oleic acid is 49.0%, the proportion of linoleic acid is 30.9%, and the proportion of linolenic acid is 12.6%. In one embodiment, it is preferable that the fatty acid constituting the fatty acid used contains 100% oleic acid (such as oleic acid (manufactured by Tsuno Oleochemicals Co., Ltd.)). The proportions of these fatty acids constituting the fatty acids can be calculated by known methods such as gas chromatography. 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 for the fatty acids to be used.

[0017] (Specific examples of fatty acids containing 18 carbon atoms) In the present disclosure, examples of fatty acids containing a fatty acid having 18 carbon atoms include oleic acid, stearic acid, isostearic acid, elaidic acid, linoleic acid, linolenic acid, TFA-125 (manufactured by Tsuno Oleochemicals Co., Ltd.), TFA-145WF (manufactured by Tsuno Oleochemicals Co., Ltd.), Evap Oleo O-185 (manufactured by Evyap), and NAS-125 (manufactured by Tsuno Oleochemicals Co., Ltd.), and these fatty acids may be used alone or in any combination.

[0018] <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.), PEG-1500 (manufactured by Aoki Oil & Fats Industries Co., Ltd.), and PEG-600 (manufactured by Aoki Oil & Fats Industries Co., Ltd.).

[0019] 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 or 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.

[0020] 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, as well as Braunon P-106 (manufactured by Aoki Oil Industries Co., Ltd.) and Braunon EP-0840 (manufactured by Aoki Oil Industries Co., Ltd.).

[0021] (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 from (100 / 0) to (50 / 50), from (100 / 0) to (56 / 44), from (100 / 0) to (57 / 43), or from (100 / 0) to (60 / 40).

[0022] (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 2,000, or 2,400 to 3,500.

[0023] (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, 2000 or less, 200 or more, 200 or more and 2000 or less, 400 or more and 2000 or less, or 600 or more and 2000 or less. When the polyalkylene glycol is an EO-PO-EO block copolymer, the number average molecular weight may be 4,000 or less, or less than 4,000, or 1,000 or more and 4,000 or less, or 1,400 or more and 3,500 or less, or 2,500 or more and 3,500 or less.

[0024] The polyalkylene glycol used in the reaction may be one type or two or more types.

[0025] (Molar ratio of fatty acid containing 18 carbon atoms to polyalkylene glycol in the reaction) The molar ratio of the fatty acid containing a fatty acid having 18 carbon atoms to the polyalkylene glycol in the 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 (1:1) to (1:6), or may be (1:3) to (1:9).

[0026] (Preferable combination of molar ratio of fatty acid containing fatty acid having 18 carbon atoms to polyalkylene glycol and number average molecular weight of polyalkylene glycol in the reaction) When the molar ratio of the fatty acid containing a fatty acid having 18 carbon atoms to the polyalkylene glycol in the reaction is 1:9, the number average molecular weight of the polyalkylene glycol is preferably, for example, 200 or more and 2,000 or less, 400 or more and 2,000 or less, or 600 or more and 2,000 or less. When the molar ratio of the fatty acid containing a fatty acid having 18 carbon atoms to the polyalkylene glycol in the reaction is 1:3, the number average molecular weight of the polyalkylene glycol is preferably, for example, 200 or more and 2,000 or less, 400 or more and 2,000 or less, or 600 or more and 2,000 or less. When the molar ratio of the fatty acid containing a fatty acid having 18 carbon atoms to the polyalkylene glycol in the reaction is 1:1, the number average molecular weight of the polyalkylene glycol is preferably, for example, 200 or more and 4000 or less, 400 or more and 3800 or less, or 600 or more and 3500 or less.

[0027] (Other ingredients) In one embodiment, the composition may contain other components in addition to the fatty acid containing a C18 fatty acid and the polyalkylene glycol during the reaction. The other components may be, for example, components used in the esterification and / or transesterification reaction of glycerin or the like, or components (additives, etc.) not used in the esterification and / or transesterification reaction. In one embodiment, the composition includes a composition obtained by mixing and reacting a fatty acid containing a C18 fatty acid, a polyalkylene glycol, and glycerin. When a fatty acid containing a fatty acid having 18 carbon atoms, a polyalkylene glycol, and glycerin are mixed and reacted, the molar ratio of the fatty acid containing a fatty acid having 18 carbon atoms, the polyalkylene glycol, and the glycerin in the reaction may be (3:4:1) to (2:9:1), may be (9:1:3) to (3:9:1), may be (6:1:3) to (2:9:1), or may be (3:1:3) to (1:9:1).

[0028] (Ingredients contained in the composition) In one embodiment, the composition includes one or more components selected from polyalkylene glycol (hereinafter also referred to as "PAG"), polyalkylene glycol monoester (hereinafter also referred to as "ME"), and polyalkylene glycol diester (hereinafter also referred to as "DE"). The composition of the present disclosure preferably contains, for example, all of the above three components; at least two components selected from the above three components; components excluding PAG (two components, ME and DE); at least components excluding ME from the above components (two components, PAG and DE); at least components excluding DE from the above components (two components, PAG and ME); or one of the above three components (PAG, ME, or DE). The composition of the present disclosure may contain two or more of each of the above components. In other embodiments, the composition includes two or more components selected from, for example, 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 the above components.

[0029] The proportion of polyalkylene glycol (PAG) in the entire composition in the present disclosure may be 0 to 95 mol %, 0 to 90 mol %, or 15 to 89 mol %.

[0030] In the present disclosure, the proportion of polyalkylene glycol monoester (ME) relative to the entire composition may be 0 to 80 mol %, 0 to 75 mol %, or 10 to 70 mol %.

[0031] In the present disclosure, the proportion of the polyalkylene glycol diester (DE) relative to the entire composition may be 0 to 100 mol%, 0.1 to 100 mol%, 0.2 to 30 mol%, or 0.2 to 18 mol%.

[0032] The molar ratio of PAG to ME (PAG:ME) in the composition of the present disclosure may be (0-95):(0-80), (0-90):(0-75), or (15-89):(10-70).

[0033] The molar ratio of PAG to DE (PAG:DE) in the composition of the present disclosure may be (0-95):(0-100), (0-90):(0.1-100), or (15-89):(0.2-18).

[0034] The molar ratio of ME to DE (ME:DE) in the composition of the present disclosure may be (0-80):(0-100), (0-75):(0.1-100), or (10-70):(0.2-18).

[0035] The molar ratio of PAG, ME, and DE (PAG:ME:DE) in the composition of the present disclosure may be (0-95):(0-80):(0-100), or may be (0-90):(0-75):(0.1-100), or may be (15-89):(10-70):(0.2-18).

[0036] 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 %.

[0037] The proportion of monoacylglyceride (MAG) in the entire composition of the present disclosure may be 0 to 20 mol%, 2 to 20 mol%, 6 to 15 mol%, 6 to 8 mol%, or 10 to 15 mol%.

[0038] The proportion of diacylglyceride (DAG) in the entire composition in the present disclosure may be 0 to 30 mol%, 1 to 30 mol%, 1 to 6 mol%, or 6 to 30 mol%.

[0039] 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.

[0040] The molar ratio of GOL to MAG (GOL:MAG) in the composition of the present disclosure may be (0-7):(0-20), (0-7):(2-20), (0-6):(6-15), or (6-7):(6-12).

[0041] The molar ratio of GOL to DAG (GOL:DAG) in the composition of the present disclosure may be (0-7):(0-30), (0-7):(1-30), (0-6):(1-6), or (6-7):(6-30).

[0042] The molar ratio of GOL to TAG (GOL:TAG) in the composition of the present disclosure may be (0-7):(0-5), (0-7):(0.1-5), (0-6):(0.1-0.3), or (6-7):(0-5).

[0043] 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).

[0044] 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).

[0045] 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).

[0046] The molar ratio of MAG, DAG, TAG, ME, and DE (MAG:DAG:TAG:ME:DE) in the composition of the present disclosure may be (0-20):(0-30):(0-5):(25-40):(2-20), or 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).

[0047] (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 reaction between the fatty acid, including the C18 fatty acid of the present disclosure, and the polyalkylene glycol (e.g., 6 hours, 7 hours, 8 hours, 9 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 reaction (i.e., in the state of a simple mixture of the fatty acid and the polyalkylene glycol without reaction), the composition is not water-soluble. In some embodiments of the present disclosure, the start of the reaction refers to the time point when the esterification step begins. In this step, a fatty acid containing a C18 fatty acid is mixed with a polyalkylene glycol, and the mixture is heated (for example, to 40 to 230°C) to carry out the esterification reaction, optionally with or without a catalyst (for example, an acid catalyst such as sulfuric acid, methanesulfonic acid, or paratoluenesulfonic acid, or a metal catalyst containing an element such as titanium, zirconium, hafnium, tin, or zinc).

[0048] 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.

[0049] (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.

[0050] 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."

[0051] (For preventing adhesion of asphalt mixture) In some embodiments of the present disclosure, the compositions herein are useful for preventing adhesion of asphalt mixtures.

[0052] 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 the excess aqueous solution is removed. The scoop is then 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.

[0053] (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.

[0054] 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 there is no attack on rubber, and if either rate is 1% or more, it is determined that there is attack on rubber.

[0055] (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.

[0056] 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."

[0057] (pour point) In some embodiments of the present disclosure, the composition of the present disclosure (e.g., a 50% aqueous solution, a 30% aqueous solution, or a 5% aqueous solution, preferably a 5% aqueous solution) has a pour point below freezing, preferably below −2.5° 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.

[0058] 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, and preferably −50° C. or higher.

[0059] (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).

[0060] 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.

[0061] (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).

[0062] 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.

[0063] In one embodiment, the composition of the present disclosure may be substantially free of additives and may consist essentially of reaction products (e.g., one or more products selected from the group consisting of PAG, ME, and DE). When the composition is "substantially free of additives," it means, for example, that the total content of additives is less than 5% by mass. When the composition is "substantially composed of reaction products," it means, for example, that the content of products from esterification and / or transesterification reactions is 95% by mass or more. The composition of the present disclosure also encompasses compositions containing a product of an esterification reaction (e.g., one or more products selected from the group consisting of PAG, ME, and DE) without substantially involving an esterification reaction (e.g., a composition comprising a mixture of one or more components selected from the group consisting of PAG, ME, and DE). In other embodiments, the compositions of the present disclosure may be substantially free of additives and consist essentially of reaction products (e.g., five or more products selected from the group consisting of GOL, MAG, DAG, TAG, PAG, ME, and DE). The composition of the present disclosure also encompasses cases in which the composition contains products of esterification reactions and transesterification reactions (e.g., five or more products selected from the group consisting of GOL, MAG, DAG, TAG, PAG, ME, and DE) without substantially involving esterification reactions and transesterification reactions (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).

[0064] [Method of producing the composition] The composition according to the present disclosure can be produced, for example, by a production method including an esterification step of esterifying a fatty acid, including a fatty acid having 18 carbon atoms, with a polyalkylene glycol. Furthermore, the composition of the present disclosure can be produced by a production method further including, for example, an ester exchange reaction step of mixing a fatty acid containing a fatty acid having 18 carbon atoms, a polyalkylene glycol, and glycerin, and carrying out an ester exchange reaction.

[0065] The method for producing the composition may further include, after the reaction 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.

[0066] (Reaction step) In this step, a fatty acid containing a fatty acid having 18 carbon atoms is mixed with a polyalkylene glycol, and the mixture is heated (for example, at 40 to 230°C) to carry out the reaction, optionally with or without the addition of a catalyst (for example, an acid catalyst such as sulfuric acid, methanesulfonic acid, or paratoluenesulfonic acid, or a metal catalyst containing an element such as titanium, zirconium, hafnium, tin, or zinc).

[0067] The equivalent ratio of the polyalkylene glycol component to the fatty acid component containing a fatty acid having 18 carbon atoms is preferably 0.1 to 2.0 moles of carboxyl groups in the fatty acid component containing a fatty acid having 18 carbon atoms 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 viewpoints of production efficiency and economic efficiency. The number of moles of hydroxyl groups in the polyalkylene glycol component can be calculated by measuring the hydroxyl value (JIS K0070).

[0068] 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 fatty acid component containing the fatty acid having 18 carbon atoms. Catalyst-free use is also possible.

[0069] The lower limit of the reaction temperature is preferably 40° C. or higher, and may be 100° C. or higher. The upper limit of the reaction temperature may be, for example, 250° C. or lower, 240° C. or lower, or 235° C. or lower, and preferably 230° C. or lower.

[0070] The reaction may be carried out under normal pressure or under reduced pressure, but reduced pressure is preferred in order to shorten the reaction time and remove as much water as possible. The lower limit of the 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 reduced pressure is, for example, 400 Torr or less, preferably 300 Torr or less.

[0071] The lower limit of the 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 reaction time is preferably 12 hours or less, more preferably 10 hours or less, even more preferably 9 hours or less, and particularly preferably 8 hours or less.

[0072] The esterification reaction is preferably carried out while measuring the acid value, for example. The end point of the esterification reaction can be confirmed, for example, by measuring the acid value. For example, when the acid value of the reaction solution becomes a certain value or less (e.g., 10 mg KOH / g or less, 7 mg KOH / g or less, 5 mg KOH / g or less, 4.8 mg KOH / g or less, 4.6 mg KOH / g or less, etc.) (e.g., 6 hours, 7 hours, 8 hours, 9 hours, etc. after the start of the reaction), it can be considered that the fatty acids containing the C18 fatty acids have been used in the esterification reaction. Furthermore, when the reaction rate calculated from the acid value of the reaction solution before and after the reaction becomes, for example, 65% or more, 68% or more, 70% or more, 71% or more, it can be considered that the fatty acids containing the C18 fatty acids have been used in the esterification reaction.

[0073] The composition of the present disclosure and a mixture of a polyalkylene glycol and a fatty acid containing a C18 fatty acid without an esterification reaction can be distinguished by measuring the acid value. The acid value can be measured, for example, according to JOCS (Japan Oil Chemists' Society) 2.3.1. In some embodiments, the acid value of the composition of the present disclosure is lower than that of a mixture of a polyalkylene glycol and a fatty acid containing a C18 fatty acid without an esterification reaction.

[0074] As described above, in some embodiments of the present disclosure, the composition of the present disclosure has water solubility. For example, the water solubility of the composition of the present disclosure can be obtained before (for example, 3 hours, 4 hours, 5 hours, 6 hours, etc. after the start of reaction) the time when the acid value is measured and the acid value is below a certain value (for example, 10 mg KOH / g or less, 7 mg KOH / g or less, 5 mg KOH / g or less, 4.8 mg KOH / g or less, 4.6 mg KOH / g or less, etc.) (for example, 6 hours, 7 hours, 8 hours, 9 hours, etc. after the start of reaction).

[0075] (Processing process) In this step, the obtained crude esterified product is treated with a treating agent.

[0076] Examples of the treating agent include activated carbon, activated clay, etc. The amount of the treating agent used is, for example, usually 0.01 to 5% by mass, preferably 0.1 to 1% by mass, based on the esterified crude product.

[0077] 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.

[0078] In this disclosure, the term "approximate" 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.

[0079] 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]

[0080] 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.

[0081] (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. The acid value of the reaction solution of the esterification reaction in the production of the compositions of the Examples and Comparative Examples was measured in accordance with JOCS (Japan Oil Chemists' Society) 2.3.1.

[0082] (raw materials) TFA-125: Tsuno Oleochemicals Co., Ltd. Oleic acid: SINAR-OL; manufactured by SINARMAS CEPSA PEG-600: Aoki Oil & Fat Industries Co., Ltd. PEG-1500: Aoki Oil & Fat Industries Co., Ltd. PEG-2000: Sanyo Chemical Industries, Ltd. Newpol PE-64: Sanyo Chemical Industries, Ltd. Newpol PE-75: Sanyo Chemical Industries, Ltd. Brownon P-106: Aoki Oil & Fat Industries Co., Ltd. Brownon EP-0840: Aoki Oil & Fat Industries Co., Ltd. Glycerin: (Sakamoto Pharmaceutical Co., Ltd.) TREX TR-110: Manufactured by Tsuno Oleochemicals Co., Ltd. Triethylene glycol (TEG): Nippon Shokubai Co., Ltd.

[0083] <Production of Composition> Tables 1 and 2 show the blending ratios of the raw materials used in the examples and comparative examples, and the performance of the compositions produced.

[0084] About the raw material ratio [Table 1]

[0085] About the performance of the composition [Table 2]

[0086] [Example 1] A 1-L four-neck flask was charged with 187 g of TFA-125 (Tsukuno Oleochemicals Co., Ltd.) and 400 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 TFA-125:PEG-600 = 1:1), and 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 reaction was continued until the acid value of the reaction solution decreased from 62.5 mg KOH / g (before the reaction) to 3.6 mg KOH / g (reaction rate 94.2%), yielding the composition (solid) of Example 1. The composition of TFA-125 was 1.1% by mass of palmitic acid, 3.2% by mass of stearic acid, 52.4% by mass of oleic acid, 36.0% by mass of linoleic acid, and 5.1% by mass of linolenic acid (GC analysis values).

[0087] [Example 2] The composition (solid) of Example 2 was obtained in the same manner as in Example 1, except that 62 g of TFA-125 (manufactured by Tsuno Oleochemicals Co., Ltd.) and 400 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 TFA-125:PEG-600 = 1:3) were reacted until the acid value of the reaction solution changed from 26.6 mg KOH / g (before the reaction) to 4.1 mg KOH / g (reaction rate 84.8%).

[0088] [Example 3] The composition (solid) of Example 3 was obtained in the same manner as in Example 1, except that 31 g of TFA-125 (manufactured by Tsuno Oleochemicals Co., Ltd.) and 600 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 TFA-125:PEG-600 = 1:9) were reacted until the acid value of the reaction solution changed from 11.8 mg KOH / g (before the reaction) to 3.3 mg KOH / g (reaction rate 71.8%).

[0089] [Example 4] The composition (solid) of Example 4 was obtained in the same manner as in Example 1, except that 75 g of TFA-125 (manufactured by Tsuno Oleochemicals Co., Ltd.) and 400 g of PEG-1500 (EO type, number average molecular weight: 1500, EO / PO (number average molecular weight ratio) = 100 / 0, manufactured by Aoki Oil & Fat Industries Co., Ltd.) (molar ratio of TFA-125:PEG-1500 = 1:1) were reacted until the acid value of the reaction solution changed from 30.4 mg KOH / g (before the reaction) to 3.2 mg KOH / g (reaction rate 89.5%).

[0090] [Example 5] The composition (solid) of Example 5 was obtained in the same manner as in Example 1, except that 56 g of TFA-125 (manufactured by Tsuno Oleochemicals Co., Ltd.) and 400 g of PEG-2000 (EO type, number average molecular weight: 2000, EO / PO (number average molecular weight ratio) = 100 / 0, manufactured by Sanyo Chemical Industries, Ltd.) (molar ratio of TFA-125:PEG-2000 = 1:1) were reacted until the acid value of the reaction solution changed from 24.5 mg KOH / g (before the reaction) to 4.0 mg KOH / g (reaction rate 83.5%).

[0091] [Example 6] The composition (solid) of Example 6 was obtained in the same manner as in Example 1, except that 54 g of TFA-125 (manufactured by Tsuno Oleochemicals Co., Ltd.) and 600 g of Newpol PE-64 (EO-PO-EO type, number average molecular weight: 3100, EO / PO (number average molecular weight ratio) = 56 / 44, manufactured by Sanyo Chemical Industries, Ltd.) (molar ratio of TFA-125:PE-64 = 1:1) were reacted until the acid value of the reaction solution changed from 17.3 mg KOH / g (before the reaction) to 4.4 mg KOH / g (reaction rate 74.6%). [Example 7] The composition (solid) of Example 7 was obtained in the same manner as in Example 1, except that 48 g of TFA-125 (manufactured by Tsuno Oleochemicals Co., Ltd.) and 600 g of Newpol PE-75 (EO-PO-EO type, number average molecular weight: 3500, EO / PO (number average molecular weight ratio) = 57 / 43, manufactured by Sanyo Chemical Industries, Ltd.) (molar ratio of TFA-125:PE-75 = 1:1) were reacted until the acid value of the reaction solution changed from 14.6 mg KOH / g (before the reaction) to 4.1 mg KOH / g (reaction rate 72.2%). [Example 8] The composition (solid) of Example 8 was obtained in the same manner as in Example 1, except that 45 g of TFA-125 (manufactured by Tsuno Oleochemicals Co., Ltd.) and 400 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 TFA-125:P-106 = 1:1) were reacted until the acid value of the reaction solution changed from 38.9 mg KOH / g (before the reaction) to 3.5 mg KOH / g (reaction rate 91.0%). [Example 9] The composition (solid) of Example 9 was obtained in the same manner as in Example 1, except that 40 g of TFA-125 (manufactured by Tsuno Oleochemicals Co., Ltd.) and 400 g of Braunon EP-0840 (EO-PO-EO type, number average molecular weight: 1400, EO / PO (number average molecular weight ratio) = 60 / 40, manufactured by Aoki Oil & Fat Industries Co., Ltd.) (molar ratio of TFA-125:EP-0840 = 1:1) were reacted until the acid value of the reaction solution changed from 33.3 mg KOH / g (before the reaction) to 4.6 mg KOH / g (reaction rate 86.1%). [Example 10] The composition (solid) of Example 10 was obtained in the same manner as in Example 1, except that 67 g of oleic acid (manufactured by SINARMAS CEPSA) and 600 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 TFA-125:P-106 = 2:1) were reacted until the acid value of the reaction solution changed from 61.2 mg KOH / g (before the reaction) to 3.2 mg KOH / g (reaction rate 94.7%). [Example 11] The composition (solid) of Example 11 was obtained in the same manner as in Example 1, except that 189 g of oleic acid (manufactured by SINARMAS CEPSA), 20.7 g of glycerin (manufactured by Sakamoto Pharmaceutical Industry Co., Ltd.), and 540 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 oleic acid:glycerin:PEG-600 = 3:1:4) were reacted until the acid value of the reaction solution changed from 50.9 mgKOH / g (before the reaction) to 0.8 mgKOH / g (reaction rate 98.5%).

[0092] [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).

[0093] 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.

[0094] 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.

[0095] Comparative Example 4 The performance evaluations shown in Table 2 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).

[0096] Comparative Example 5 A composition (solid) of Comparative Example 5 was obtained in the same manner as in Example 1, except that 378 g of stearic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 200 g of triethylene glycol (manufactured by Nippon Shokubai Co., Ltd.) (molar ratio of stearic acid:triethylene glycol=1:1) were reacted until the acid value of the reaction solution increased from 122.8 mg KOH / g (before the reaction) to 4.0 mg KOH / g (reaction rate 96.8%).

[0097] Comparative Example 6 A composition (solid) of Comparative Example 6 was obtained in the same manner as in Example 1, except that 190 g of stearic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 300 g of triethylene glycol (manufactured by Nippon Shokubai Co., Ltd.) (molar ratio of stearic acid:triethylene glycol=1:3) were reacted until the acid value of the reaction solution changed from 77.7 mg KOH / g (before the reaction) to 2.6 mg KOH / g (reaction rate 96.7%).

[0098] Comparative Example 7 A composition (solid) of Comparative Example 7 was obtained in the same manner as in Example 1, except that 96 g of stearic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 450 g of triethylene glycol (manufactured by Nippon Shokubai Co., Ltd.) (molar ratio of stearic acid:triethylene glycol=1:9) were reacted until the acid value of the reaction solution changed from 36.1 mgKOH / g (before the reaction) to 2.5 mgKOH / g (reaction rate 93.1%).

[0099] [Comparative Example 8] The composition (solid) of Comparative Example 8 was obtained in the same manner as in Example 1, except that 298 g of oleic acid (manufactured by SINARMAS CEPSA) and 160 g of triethylene glycol (manufactured by Nippon Shokubai Co., Ltd.) (molar ratio of oleic acid:triethylene glycol = 1:1) were reacted until the acid value of the reaction solution decreased from 128.3 mg KOH / g (before the reaction) to 4.1 mg KOH / g (reaction rate 96.8%).

[0100] <Evaluation of each performance> The properties of the compositions obtained in the Examples and Comparative Examples shown in Tables 1 and 2 were 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 obtain 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. Also, as shown in Table 2, 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 compositions esterified with PAG having less than 4 carbon atoms. Furthermore, the compositions of the examples, in their 5% aqueous solutions, did not attack rubber or dissolve asphalt mixtures, and the pour point of the 5% aqueous solution was -2.5°C or below.

[0109] As is clear from the results of Example 10 and Comparative Example 8 in Table 2, compositions obtained by esterifying a fatty acid with a polyalkylene glycol having a degree of polymerization of 4 or more exhibit water solubility using the above-mentioned method, while compositions obtained by esterifying a fatty acid with a polyalkylene glycol having a degree of polymerization of less than 4 do not exhibit water solubility using the above-mentioned confirmation method, and their 50% aqueous solutions exhibited oil-water separation. Furthermore, the results of Examples 10 and 11 in Table 2 show that Example 11, in which glycerin was added to the mixture of Example 10 before esterification and esterified, also exhibited water solubility and no oil-water separation using the above-mentioned method, as in Example 1. Furthermore, the results of Examples 8 and 10 show that the fatty acid used, whether it was a C18 fatty acid alone or a mixed fatty acid containing an C18 fatty acid, exhibited water solubility and no oil-water separation using the above-mentioned method, indicating that the inclusion of at least a C18 fatty acid is effective. This demonstrates that esterifying a C18 fatty acid with a polyalkylene glycol having a degree of polymerization of 4 or more imparts water solubility and / or stability against oil-water separation to the resulting composition.

[0110] As shown in Examples 1, 5, 7, and 8 in Table 2, the pour point of a 5% aqueous solution of the composition is lower than the freezing point of water (0°C). Furthermore, the compositions of the examples become liquid at room temperature (25°C) when mixed with water. This means that when each composition is mixed with water, the composition itself liquefies 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 of Examples 1 and 2 in Tables 1 and 2 show that even when the molar ratio of fatty acid 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 9 show that even when the number-average molecular weight of the PAG used in the examples or the ratio of EO to PO (number-average molecular weight ratio) was 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 an esterification reaction product of a fatty acid and a PAG with 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 reacting a fatty acid, including a fatty acid having 18 carbon atoms, with a polyalkylene glycol, wherein the composition contains polyalkylene glycol.

2. A composition for preventing adhesion of asphalt mixtures, comprising an aqueous solution containing a composition obtained by reacting a fatty acid, including a fatty acid having 18 carbon atoms, with a polyalkylene glycol, wherein the composition contains a diester of polyalkylene glycol.

3. A composition for preventing adhesion of asphalt mixtures, comprising an aqueous solution containing a composition obtained by reacting a fatty acid, including a fatty acid having 18 carbon atoms, with a polyalkylene glycol, wherein the composition contains at least two or more selected from polyalkylene glycol, monoester of polyalkylene glycol, and diester of polyalkylene glycol.

4. A composition for preventing adhesion of asphalt mixtures, comprising an aqueous solution containing a composition obtained by reacting a fatty acid, including a fatty acid having 18 carbon atoms, with a polyalkylene glycol, wherein the polyalkylene glycol has an oxypropylene group (PO).

5. A composition for preventing adhesion of asphalt mixtures, comprising an aqueous solution containing a composition obtained by reacting a fatty acid, including a fatty acid having 18 carbon atoms, a polyalkylene glycol, and glycerin, wherein the composition contains glycerin.

6. 6. 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.

7. 6. The adhesion preventive composition for asphalt mixtures according to claim 1, wherein the molar ratio of the fatty acid containing a fatty acid having 18 carbon atoms to the polyalkylene glycol is 3:1 to 1:

9.

8. The composition for preventing adhesion of asphalt mixtures according to any one of claims 1 to 5, 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.

Images