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 reacting a fatty acid containing a fatty acid having 18 carbon atoms 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 anti-adhesion agents for asphalt composites, but there were problems such as adverse effects on the surrounding environment, dissolution of asphalt on the pavement surface, acceleration of tire deterioration, and flammability. As an anti-adhesion agent for asphalt composites having performance equivalent to or better than that of mineral oil and heavy oil, an anti-adhesion 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 is 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 this problem, an anti-adhesion agent for asphalt composites using a polyalkylene glycol derivative that does not contain an oily component and has high affinity for water has been reported, but there is a problem that the effect is insufficient at low concentrations.

[0003] Various compositions and the like related to anti-adhesion agents 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

[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 admixtures. More preferably, the problem of the present disclosure is to provide a composition having high asphalt admixture 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 admixtures, which is excellent in safety and environmental conservation, 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 reacting a fatty acid containing a fatty acid having 18 carbon atoms with a polyalkylene glycol.

[0008] The present disclosure relates to the following inventions and the like. [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 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 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 [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] The composition according to any one of [1] to [4] above, 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 containing the aqueous solution according to [6] above. [8] The composition according to any one of [1] to [5] and [7] above, which is for preventing adhesion of asphalt composite materials.

Advantages 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 performance in preventing adhesion of asphalt composite materials 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.

Modes for Carrying Out the Invention

[0010] <Composition> This disclosure provides a composition obtained by reacting a fatty acid containing a C18 fatty acid with a polyalkylene glycol (e.g., esterification, transesterification, etc.) (for example, by mixing a mixed fatty acid containing a C18 fatty acid with a polyalkylene glycol, heating it under a nitrogen atmosphere at a temperature above room temperature, for example, 40 to 250°C, and draining the resulting water out of the system under normal or reduced pressure). The composition may contain several esters obtained by reacting a fatty acid containing a C18 fatty acid with a polyalkylene glycol (e.g., esterification, transesterification, etc.). The composition may also be obtained by reacting a fatty acid containing a C18 fatty acid, a polyalkylene glycol, and glycerin (e.g., esterification, transesterification, etc.). The composition may be obtained by esterification and transesterification reactions of a fatty acid containing a C18 fatty acid, a polyalkylene glycol, and glycerin, or by at least esterification reactions. The composition may or may not contain any other optional components besides the esters. The composition may also contain glycerin and / or polyalkylene glycol in addition to the ester. 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 reacting a fatty acid containing a C18 fatty acid with 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. In this disclosure, "reacted" includes cases where a reaction such as an esterification reaction or a transesterification reaction is carried out. Furthermore, in this disclosure, when the term "reaction" is used without further context, 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, 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.

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

[0013] (Composition of fatty acids used) When palmitic acid is included as one of the fatty acids that make up the fatty acid used, the proportion of palmitic acid to the total fatty acids that make up 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, for example, it may be 0.1 to 35%, 0.5 to 25%, or 1 to 12%. In this disclosure, where "%" is used without further explanation, it may refer to "mass%". When stearic acid is included as one of the fatty acids that make up the fatty acid used, the proportion of stearic acid to the total fatty acids that make up 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, for example, it may be 0.1-20%, 1-6%, or 1-4.5%. When oleic acid is included as one of the fatty acids that make up the fatty acid used, the proportion of oleic acid to the total amount of fatty acids that make up the fatty acid used may be, for example, a lower limit of 1%, 7%, 10%, 20%, 30%, 34%, 40%, 44%, 50%, 52%, or 54%, and an upper limit of 100%, or 90%, 85%, 81%, 80%, 70%, 67%, or 63%, or a combination of the above lower and upper limits. Specifically, for example, it may be 7-100%, 30-100%, or 34-100%. When linoleic acid is included as one of the fatty acids that make up the fatty acid used, the proportion of linoleic acid to the total amount of fatty acids that make up the fatty acid used may be, for example, a lower limit of 0.1%, 1.5%, 5%, 10%, 11%, 15%, 18%, 20%, 21%, 33%, or 36%, and an upper limit of 70%, 60%, 56%, 55%, 50%, 40%, or 37%, or a combination of the above lower and upper limits. Specifically, for example, it may be 1.5-70%, 5-60%, or 10-40%. When linolenic acid is included as one of the fatty acids that make up the fatty acid used, the proportion of linolenic acid to the total amount of fatty acids that make up 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, for example, it may be 0.01 to 65%, 3 to 20%, or 4 to 13%.

[0014] In one embodiment, when the fatty acids constituting the fatty acid used include palmitic acid and stearic acid, the proportion of stearic acid to the total fatty acids constituting the fatty acid used may be greater than that of palmitic acid (for example, 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 acid used include stearic acid and oleic acid, the proportion of oleic acid to the total fatty acids constituting the fatty acid used may be greater than that of stearic acid (for example, 10 times or more, 15 times or more, 16 times or more). 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 greater than that of linoleic acid (for example, 1.2 times or more, 1.4 times or more). In one embodiment, when the fatty acids constituting the fatty acid used include linoleic acid and linolenic acid, the proportion of linoleic acid to the total fatty acids constituting the fatty acid used may be greater than that of linolenic acid (for example, 4 times or more, 5 times or more, 7 times or more). In one embodiment, when the fatty acids used include palmitic acid and oleic acid, the proportion of oleic acid to the total fatty acids that make up the fatty acid used may be greater than that of palmitic acid (for example, 15 times or more, 30 times or more, 40 times or more, 45 times or more). In one embodiment, when the fatty acids used include palmitic acid and linoleic acid, the proportion of linoleic acid to the total fatty acids that make up the fatty acid used may be greater than that of palmitic acid (for example, 2 times or more, 15 times or more, 20 times or more, 30 times or more). In one embodiment, when the fatty acids used include stearic acid and linoleic acid, the proportion of linoleic acid to the total fatty acids that make up the fatty acid used may be greater than that of stearic acid (for example, 6 times or more, 8 times or more, 10 times or more). In one embodiment, when the fatty acids used include stearic acid and linolenic acid, the proportion of linolenic acid to the total fatty acids that make up the fatty acid used may be 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 used include oleic acid and linolenic acid, the proportion of oleic acid to the total fatty acids that make up the fatty acid used may be greater than that of linolenic acid (for example, 3 times or more, 6 times or more, or 10 times or more). In this disclosure, where the term "proportion" is used without further context, it may refer to a "mass proportion."

[0015] In one embodiment, when the fatty acids constituting the fatty acid 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 amount of fatty acids constituting the fatty acid is set to 100, for example, (0.01~50):(0.01~30):(1~100):(0.1~70):(0~65), (0.1~40):(0 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) may also be used. The proportion of fatty acids that make up these fatty acids can be calculated by analyzing the fatty acids using known methods such as gas chromatography.

[0016] In one embodiment, when the fatty acids used include oleic acid and linoleic acid, the proportion of oleic acid to the total fatty acids that make up the fatty acid used may be 30-85%, and the proportion of linoleic acid may be 10-60%. In one embodiment, the proportion of palmitic acid to the total fatty acids constituting the fatty acid is preferably 1.1%, the proportion of stearic acid is 3.2%, the proportion of oleic acid is 52.4%, the proportion of linoleic acid is 36%, and the proportion of linolenic acid is 5.1% (e.g., TFA-125 (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 fatty acids used is 1.5%, the proportion of stearic acid is 3.7%, the proportion of oleic acid is 54.5%, the proportion of linoleic acid is 33.3%, and the proportion of linolenic acid is 7.0%. In another embodiment, it is preferable that the proportion of palmitic acid 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 preferable that the proportion of palmitic acid 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 preferable that the proportion of palmitic acid 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 used is composed of 100% oleic acid (such as oleic acid (manufactured by Tsukuno Oleochemicals Co., Ltd.)). The proportions of the fatty acids constituting these fatty acids can be calculated by known methods such as gas chromatography. Furthermore, by appropriately combining the preferred proportions of these various fatty acids, a fatty acid composition within a preferred range can be applied to the fatty acids being used.

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

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

[0019] 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.

[0020] 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.) and Brownon EP-0840 (manufactured by Aoki Oil & Fat Industry Co., Ltd.).

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

[0022] (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 2000, or 2400 to 3500.

[0023] (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, 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 4000 or less, less than 4000, between 1000 and 4000, between 1400 and 3500, or between 2500 and 3500.

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

[0025] (Molar ratio of fatty acids containing 18 carbon atoms to polyalkylene glycols in the reaction) The molar ratio of the fatty acid containing a C18 fatty acid to the polyalkylene glycol in the reaction may be (3:1) to (1:9), (3:1) to (1:6), (1:1) to (1:3), (1:1) to (1:9), (1:1) to (1:6), or (1:3) to (1:9).

[0026] (Preferred combinations of the molar ratio of fatty acids containing 18 carbon atoms to polyalkylene glycols and the number-average molecular weight of polyalkylene glycols in the reaction) When the molar ratio of the fatty acid containing a C18 fatty acid to the polyalkylene glycol in the reaction is 1:9, the number-average molecular weight of the polyalkylene glycol is preferably, for example, 200 to 2000, 400 to 2000, or 600 to 2000. When the molar ratio of the fatty acid containing a C18 fatty acid to the polyalkylene glycol in the reaction is 1:3, the number-average molecular weight of the polyalkylene glycol is preferably, for example, 200 to 2000, 400 to 2000, or 600 to 2000. When the molar ratio of the fatty acid containing a C18 fatty acid to the polyalkylene glycol in the reaction is 1:1, the number-average molecular weight of the polyalkylene glycol is preferably, for example, 200 to 4000, 400 to 3800, or 600 to 3500.

[0027] (Other ingredients) In one embodiment, the composition may contain, in addition to a fatty acid containing a C18 fatty acid and polyalkylene glycol, other components during the reaction. These other components may be, for example, components used in esterification and / or transesterification reactions such as glycerin, or components not used in esterification and / or transesterification reactions (such as additives). In one embodiment, the composition encompasses a composition obtained by mixing and reacting a fatty acid containing a C18 fatty acid, polyalkylene glycol, and glycerin. When a reaction is carried out by mixing a fatty acid containing a fatty acid with 18 carbon atoms, polyalkylene glycol, and glycerin, the molar ratio of the fatty acid containing a fatty acid with 18 carbon atoms, polyalkylene glycol, and glycerin in the reaction may be (3:4:1) to (2:9:1), (9:1:3) to (3:9:1), (6:1:3) to (2:9:1), or (3:1:3) to (1:9:1).

[0028] (Ingredients contained in the composition) In one embodiment, the composition may include, for example, 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"). Preferably, the composition in this disclosure contains, for example, all three components; at least two components selected from the three components; components excluding PAG (two components: ME and DE); components excluding ME from at least the above components (two components: PAG and DE); components excluding DE from at least the above components (two components: PAG and ME); or one component from the three components (PAG, ME, or DE). The composition in this disclosure may contain two or more of each of the above components. In other embodiments, 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 contains, 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 polyalkylene glycol (PAG) to the total composition in this disclosure may be 0 to 95 mol%, 0 to 90 mol%, or 15 to 89 mol%.

[0030] The proportion of polyalkylene glycol monoester (ME) to the total composition in this disclosure may be 0 to 80 mol%, 0 to 75 mol%, or 10 to 70 mol%.

[0031] The proportion of polyalkylene glycol diester (DE) to the total composition in this disclosure 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 compositions of this 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 compositions of this 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 compositions of this 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 in the composition of this disclosure (PAG:ME:DE) may be (0-95):(0-80):(0-100), (0-90):(0-75):(0.1-100), or (15-89):(10-70):(0.2-18).

[0036] 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%.

[0037] The proportion of monoacylglycerides (MAGs) to the total composition in this 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) to the total composition in this disclosure may be 0 to 30 mol%, 1 to 30 mol%, 1 to 6 mol%, or 6 to 30 mol%.

[0039] 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.

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

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

[0047] (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 reaction between the fatty acid containing the C18 fatty acid of this disclosure and the polyalkylene glycol (e.g., 6 hours, 7 hours, 8 hours, 9 hours, etc., from the start of the reaction). The compositions that become water-soluble after the above-mentioned period of time may maintain their water solubility thereafter. Before the start of the reaction (i.e., in the state of a simple mixture of fatty acid and polyalkylene glycol without reaction), the compositions are not water-soluble. In some embodiments of this disclosure, the start of the reaction means the point in time when the esterification step begins. In this step, a fatty acid containing a C18 fatty acid is mixed with a polyalkylene glycol, and the esterification reaction is carried out by heating (for example, 40 to 230°C) with or without a catalyst, optionally with an acid catalyst (e.g., an acid catalyst such as sulfuric acid, methanesulfonic acid, or p-toluenesulfonic acid, or a metal catalyst containing elements such as titanium, zirconium, hafnium, tin, or zinc).

[0048] 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.

[0049] (oil / water separation) In some embodiments of this disclosure, the compositions present herein do not undergo oil-water separation when mixed with water.

[0050] 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."

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

[0052] 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.

[0053] (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.

[0054] 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.

[0055] (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.

[0056] 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".

[0057] (Pour point) In some embodiments of this disclosure, the compositions of this disclosure (e.g., a 50% aqueous solution, a 30% aqueous solution, a 5% aqueous solution, preferably a 5% aqueous solution) have a pour point below freezing, preferably -2.5°C or lower. 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.

[0058] 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.

[0059] (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).

[0060] 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.

[0061] (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.).

[0062] 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.

[0063] In one embodiment, the composition of this disclosure may be substantially free of additives and consist substantially of reaction products (e.g., one or more products selected from the group consisting of 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 reaction products" means, for example, that the content of products from esterification and / or transesterification reactions is 95% by mass or more. Furthermore, the compositions in this disclosure also include cases in which the products of an esterification reaction (for example, one or more products selected from the group consisting of PAG, ME, and DE) are included without substantially undergoing an esterification reaction (for example, a composition made by mixing one or more components selected from the group consisting of PAG, ME, and DE). In other embodiments, the compositions of this disclosure may be substantially free of additives and consist substantially of reaction products (e.g., five or more products selected from the group consisting of GOL, MAG, DAG, TAG, PAG, ME, and DE). Furthermore, the compositions in this disclosure also include cases in which products of esterification and 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 esterification and 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).

[0064] [Method for producing the composition] The compositions in this disclosure can be produced, for example, by a production method comprising an esterification step in which a fatty acid containing a C18 fatty acid is esterified with a polyalkylene glycol. Furthermore, the compositions in this disclosure can be produced by a manufacturing method that further includes a transesterification step, for example, of mixing a fatty acid containing a C18 fatty acid, a polyalkylene glycol, and glycerin and carrying out a transesterification reaction.

[0065] The method for producing the composition may further include a step of removing low-boiling-point components from the ester obtained after the reaction 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.

[0066] (Reaction process) In this process, a fatty acid containing a C18 fatty acid is mixed with a polyalkylene glycol, and a catalyst may be added as needed (for example, an acid catalyst such as sulfuric acid, methanesulfonic acid, or p-toluenesulfonic acid; or a metal catalyst containing elements such as titanium, zirconium, hafnium, tin, or zinc), or it may be done without a catalyst, and the reaction is carried out by heating (for example, at 40-230°C).

[0067] The equivalent ratio of the polyalkylene glycol component to the fatty acid component containing a C18 fatty acid is preferably 0.1 to 2.0 moles of carboxyl groups in the fatty acid component containing a C18 fatty acid for every 1 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).

[0068] 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 fatty acid component containing a C18 fatty acid. No catalyst may be used.

[0069] The lower limit of the reaction temperature is preferably 40°C or higher, and may also be 100°C or higher. The upper limit of the reaction temperature may be, for example, 250°C or lower, 240°C or lower, 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 preferable to shorten the reaction time and remove as much of the generated water as possible. 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.

[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. 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 endpoint of the esterification reaction can be confirmed, for example, by measuring the acid value. For example, when the acid value of the reaction solution falls 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 after the start of the reaction, etc.), it can be considered that the fatty acid containing a C18 fatty acid has been used in the esterification reaction. In addition, when the reaction rate calculated from the acid value of the reaction solution before and after the reaction reaches, for example, 65% or more, 68% or more, 70% or more, 71% or more, etc., it can be considered that the fatty acid containing a C18 fatty acid has been used in the esterification reaction.

[0073] The compositions in this disclosure and mixtures of fatty acids containing a simple C18 fatty acid without esterification and polyalkylene glycol can be distinguished by measuring their acid values. In 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, when comparing the acid values ​​of the compositions in this disclosure and mixtures of fatty acids containing a simple C18 fatty acid without esterification and polyalkylene glycol, the former has a lower acid value.

[0074] 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 in time when the acid value in an acid value measurement reaches a certain value or less (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 after the start of the reaction, etc.) (for example, 3 hours, 4 hours, 5 hours, 6 hours after the start of the reaction, etc.).

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

[0076] 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.

[0077] 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.

[0078] 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.

[0079] 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]

[0080] 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.

[0081] (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. The acid value of the reaction solution in the esterification reaction during the preparation of the compositions in the examples and comparative examples was measured according to JOCS (Japan Oil Chemists' Society) 2.3.1.

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

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

[0084] Regarding the mixing ratio of raw materials [Table 1]

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

[0086] [Example 1] 187 g of TFA-125 (manufactured by 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, manufactured by Aoki Oil & Fat Industry Co., Ltd.) were charged into a 1 L four-necked flask (molar ratio of TFA-125:PEG-600 = 1:1), and the mixture was heated to 230°C while stirring at 250 rpm under a nitrogen atmosphere. After reaching 230°C, the pressure was reduced to 100-300 Torr, and the reaction was carried out until the acid value of the reaction solution decreased from 62.5 mg KOH / g (before reaction) to 3.6 mg KOH / g (reaction rate 94.2%) to obtain 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 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, manufactured by Aoki Oil & Fat Industry Co., Ltd.) (molar ratio of TFA-125:PEG-600 = 1:3) were reacted until the acid value of the reaction solution decreased from 26.6 mg KOH / g (before 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 Tsukuno 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 Industry 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 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 Tsukuno 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 Industry Co., Ltd.) (molar ratio of TFA-125:PEG-1500 = 1:1) were reacted until the acid value of the reaction solution decreased from 30.4 mg KOH / g (before 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 Tsukuno 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 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 Tsukuno 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 decreased from 17.3 mg KOH / g (before 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 Tsukuno 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 decreased from 14.6 mg KOH / g (before 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 Tsukuno Oleochemicals Co., Ltd.) and 400 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.) (molar ratio of TFA-125:P-106 = 1:1) were reacted until the acid value of the reaction solution decreased from 38.9 mg KOH / g (before 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 Tsukuno Oleochemicals Co., Ltd.) and 400 g of Brownon 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 Industry Co., Ltd.) (molar ratio of TFA-125:EP-0840 = 1:1) were reacted until the acid value of the reaction solution decreased from 33.3 mg KOH / g (before 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 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.) (molar ratio of TFA-125:P-106 = 2:1) were reacted until the acid value of the reaction solution decreased from 61.2 mg KOH / g (before 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 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 Co., Ltd.) (molar ratio of oleic acid:glycerin:PEG-600 = 3:1:4) were used and the reaction was carried out until the acid value of the reaction solution changed from 50.9 mg KOH / g (before reaction) to 0.8 mg KOH / g (reaction rate 98.5%).

[0092] [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).

[0093] [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.

[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 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.

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

[0096] [Comparative Example 5] A composition (solid) for 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 to triethylene glycol = 1:1) were used and the reaction was carried out until the acid value of the reaction solution changed from 122.8 mg KOH / g (before reaction) to 4.0 mg KOH / g (reaction rate 96.8%).

[0097] [Comparative Example 6] A composition (solid) for 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 to triethylene glycol = 1:3) were used and the reaction was carried out until the acid value of the reaction solution decreased from 77.7 mg KOH / g (before reaction) to 2.6 mg KOH / g (reaction rate 96.7%).

[0098] [Comparative Example 7] The 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 to triethylene glycol = 1:9) were used and the reaction was carried out until the acid value of the reaction solution decreased from 36.1 mg KOH / g (before reaction) to 2.5 mg KOH / 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 to triethylene glycol = 1:1) were used and the reaction was carried out until the acid value of the reaction solution changed from 128.3 mg KOH / g (before reaction) to 4.1 mg KOH / g (reaction rate 96.8%).

[0100] <Evaluation of each performance aspect> The performance of each composition obtained in the examples and comparative examples shown in Tables 1 and 2 was evaluated 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 2, 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 compositions esterified with PAG having fewer than 4 carbon atoms. Moreover, the composition of the example, in its 5% aqueous solution, did not attack rubber, did not dissolve asphalt mixtures, and its pour point in the 5% aqueous solution was -2.5°C or lower.

[0109] As is clear from the results of Example 10 and Comparative Example 8 in Table 2, the composition obtained by esterifying a fatty acid with a polyalkylene glycol having a degree of polymerization of 4 or higher showed water solubility using the method described above, while the composition obtained by esterifying a fatty acid with a polyalkylene glycol having a degree of polymerization of less than 4 did not have water solubility using the method described above, and its 50% aqueous solution underwent oil-water separation. Furthermore, from the results of Examples 10 and 11 in Table 2, Example 11, in which glycerin was added to the mixture of Example 10 before esterification and then esterified, also showed water solubility using the method described above, similar to Example 1, and did not undergo oil-water separation. Moreover, from the results of Examples 8 and 10, it was found that whether the fatty acid used was a fatty acid with 18 carbon atoms alone or a mixed fatty acid containing a fatty acid with 18 carbon atoms, it showed water solubility using the method described above and did not undergo oil-water separation. Therefore, it was found that including at least a fatty acid with 18 carbon atoms is sufficient to achieve the desired effect. From this, it became clear that esterifying a fatty acid with 18 carbon atoms 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.

[0110] As shown in Examples 1, 5, 7, and 8 of 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 in the examples become liquid at room temperature (25°C) when mixed with water. This means that when each composition is mixed with water, it becomes liquid itself and simultaneously 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] From the results of Examples 1 and 2 in Tables 1 and 2, it was found that even when the molar ratio of fatty acid to PAG differed, the mixture remained water-soluble and exhibited an anti-adhesion effect on asphalt mixtures. Furthermore, from the results of Examples 1 to 9, 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 (number-average molecular weight ratio) 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 esterification reaction product of fatty acid and PAG with a degree of polymerization of 4 or higher is performed, 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 reacting a fatty acid containing a fatty acid with 18 carbon atoms 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 a fatty acid containing a fatty acid having 18 carbon atoms to 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. The composition according to claim 1 or 2, obtained by reacting a fatty acid containing a fatty acid having 18 carbon atoms, a polyalkylene glycol, and glycerin.

6. An aqueous solution comprising the composition according to claim 1 or 2.

7. A lubricating composition comprising the aqueous solution described in claim 6.

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