Water-soluble heat-treated oil composition

Abstract

The present invention addresses the problem of providing a water-soluble heat-treated oil composition having excellent oil separation properties. The water-soluble heat-treated oil composition contains a hydroxyl group-containing monoamine compound (A) represented by general formula (a-1), and polyethyleneimine (B).　(a-1): R1ꟷNHꟷR2 (In general formula (a-1), R1 is a hydrogen atom or a C1-6 alkyl group having no substituent, and R2 is a substituted alkyl group having one hydroxyl group. Each of the ꟷCH2ꟷ in the substituted alkyl group in R2 may be independently substituted with ꟷOꟷ.)

Description

Water-soluble heat-treated oil composition

[0001] The present invention relates to a water-soluble heat-treated oil composition.

[0002] Metal parts such as gears are typically shaped through cutting processes and then heat-treated to adjust their hardness, toughness, and other properties to produce a final product. Oil-soluble metalworking oils or water-soluble metalworking oils are used in the cutting processes, but these metalworking oils may not be completely removed by the cleaning process and may remain on the surface of the metal material. Furthermore, when there is a time gap between the cutting process and the heat treatment process, or when the processes are performed in different locations, a rust-preventive oil is applied to the metal material after the cutting process. When these metalworking oils or rust-preventive oils are mixed into the water-soluble heat treatment oil composition, which serves as a coolant for the heat treatment process, they emulsify and significantly change the state of the water-soluble heat treatment oil composition. As a result, the cooling performance of the water-soluble heat treatment oil composition is significantly affected, resulting in defects such as insufficient hardness, cracking, and distortion of the metal material. Furthermore, the water-soluble heat treatment oil composition is susceptible to spoilage by microorganisms, shortening its liquid life. In order to address such problems, for example, a water-soluble quenching liquid composition using a quaternary ammonium salt of cationic polyethyleneimine having a specific structure as a demulsifier has been investigated (see, for example, Patent Document 1).

[0003] JP 2012-153809 A

[0004] However, in Patent Document 1, the test was conducted only on lubricating oil compositions that are difficult to mix with water, and the oil separation properties of water-soluble heat-treated oil compositions were not sufficiently examined.

[0005] Therefore, an object of the present invention is to provide a water-soluble heat-treated oil composition having excellent oil-separating properties.

[0006] The present inventors have conducted extensive research to solve the above-mentioned problems. As a result, they have discovered that a water-soluble heat-treated oil composition containing a monoamine compound having a specific structure and polyethyleneimine can solve the above-mentioned problems. Based on the above-mentioned findings, the present inventors have conducted further research and have completed the present invention.

[0007] According to the present invention, the following items [1] to [4] are provided: [1] A water-soluble heat treatment oil composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1) and polyethyleneimine (B). １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each of the - may be independently substituted with -O-.) [2] A method for producing a water-soluble heat-treatment oil composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1) and a polyethyleneimine (B), the method comprising the step of mixing the hydroxyl group-containing monoamine compound (A) and the polyethyleneimine (B). R １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each of the - may be independently substituted with -O-.) [3] A method for producing a water-soluble heat-treatment oil composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1), a polyethyleneimine (B), and water, the method comprising the step of mixing the hydroxyl group-containing monoamine compound (A), the polyethyleneimine (B), and the water. R １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２Each of the - may be independently substituted with -O-.) [4] A method for separating oil, comprising a step of contacting a water-soluble heat-treated oil composition containing polyethyleneimine (B) with a composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1): １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each - may be independently substituted with -O-.

[0008] According to the present invention, it is possible to provide a water-soluble heat-treated oil composition having excellent oil-separating properties.

[0009] The upper and lower limit values ​​of the numerical ranges described in this specification can be combined in any way. For example, when "A to B" and "C to D" are described as numerical ranges, the numerical ranges "A to D" and "C to B" are also included in the scope of the present invention. Furthermore, the numerical range "lower limit to upper limit" described in this specification means that the range is equal to or greater than the lower limit and equal to or less than the upper limit, unless otherwise specified. Furthermore, in this specification, the numerical values ​​in the examples are numerical values ​​that can be used as upper or lower limit values.

[0010] In the following description, the "hydroxyl group-containing monoamine compound (A)" and the "polyethyleneimine (B)" will also be referred to as "component (A)" and "component (B)," respectively. The "hydroxyl group-containing monoamine compound (A)" and the "polyethyleneimine (B)" will also be collectively referred to as the "active ingredients," and the total content of the "hydroxyl group-containing monoamine compound (A)" and the "polyethyleneimine (B)" will also be referred to as the "total amount of active ingredients."

[0011] [Embodiments of Water-Soluble Heat Treatment Oil Composition] The water-soluble heat treatment oil composition of this embodiment contains a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1) and polyethyleneimine (B). １ -NH-R ２...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each - may be independently substituted with -O-.

[0012] The present inventors conducted extensive research to solve the above-mentioned problems. As a result, they discovered that a water-soluble heat-treated oil composition containing the above-mentioned components has excellent oil-separability. Further research led to the completion of the present invention. The reason why the water-soluble heat-treated oil composition of this embodiment has excellent oil-separability is not clear, but it is presumed to be due to the following mechanism. That is, when an oil other than the heat-treated oil is mixed into a water-soluble heat-treated oil composition containing the components (A) and (B), an emulsion is formed due to the influence of an emulsifier in the oil. Here, for example, when the emulsifier is an anionic surfactant, the counterion of the hydrophilic group moiety of the anionic surfactant is exchanged with component (A), and the fatty acid or the like constituting the anionic surfactant and component (A) form a salt. Component (A) has a primary or secondary amine group, and these amine groups have a strong bonding strength with fatty acids or the like, so the ionicity of the salt of the fatty acid or the like constituting the anionic surfactant and component (A) is high. This improves the anionicity of the droplet surface in the emulsion, and many droplets are adsorbed and aggregated by the polycation component (B). Furthermore, since component (A) has only one hydroxyl group, its hydrophilicity is relatively low. When the counterion of the hydrophilic group of the anionic surfactant is exchanged with component (A), the balance between the hydrophilicity and lipophilicity of the droplet surface is disrupted, and the droplet film becomes unstable. From the above, it is presumed that the droplets aggregated by component (B) coalesce, the unstable droplet film is destroyed, the droplets become larger in size, and the oil content is easily separated.

[0013] Hereinafter, each component contained in the water-soluble heat-treated oil composition of this embodiment will be described in detail.

[0014] <Hydroxyl Group-Containing Monoamine Compound (A)> The hydroxyl group-containing monoamine compound (A) used in this embodiment is a hydroxyl group-containing monoamine compound represented by the following general formula (a-1): R １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each - may be independently substituted with -O-.) It is presumed that the hydroxyl group-containing monoamine compound (A) exchanges with the counter ion of the hydrophilic group moiety of the emulsifier or the like in the oil mixed into the water-soluble heat-treated oil composition of this embodiment, destabilizing the droplet film and facilitating the coalescence of the droplets, thereby contributing to improved oil separation. The hydroxyl group-containing monoamine compound (A) may be used alone or in combination of two or more.

[0015] In the above general formula (a-1), R １ represents a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms. １ When R is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms and no substituent, the bonding strength of the hydroxyl group-containing monoamine compound (A) with a fatty acid or the like is easily improved. １ The alkyl group having 1 to 6 carbon atoms that can be selected as R may be either linear or branched. １ is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, and even more preferably a hydrogen atom. That is, the hydroxyl group-containing monoamine compound (A) is preferably a primary amine.

[0016] In addition, in the general formula (a-1), R ２ represents a substituted alkyl group having one hydroxyl group, and R ２ -CH of the substituted alkyl group ２Each - may be independently substituted with -O-. Here, the hydroxyl group may be any of a primary, secondary, and tertiary hydroxyl group, but from the viewpoint of ensuring the water solubility of the hydroxyl group-containing monoamine compound (A), a primary or secondary hydroxyl group is preferred, and a primary hydroxyl group is more preferred. When the alkyl group has only one hydroxyl group, it is possible to easily impart water solubility to the hydroxyl group-containing monoamine compound (A) while maintaining the hydrophilicity of the hydroxyl group-containing monoamine compound (A) relatively low. R ２ The substituted alkyl group that can be selected as R may be either linear or branched. ２ The number of carbon atoms in the substituted alkyl group that can be selected as R is preferably 1 to 6, more preferably 1 to 5, even more preferably 2 to 5, still more preferably 2 to 4, and even more preferably 3 to 4, from the viewpoint of adjusting the hydrophilicity of the hydroxyl group-containing monoamine compound (A) within an appropriate range. ２ -CH of the substituted alkyl group ２ Each - may be independently replaced by -O-, for example, R ２ -CH of the substituted alkyl group ２ When one of - is replaced by -O-, R ２ can be represented by the following general formula (a-1'): *-L'-O-R' (a-1') (In the general formula (a-1'), L' is an alkylene group, and R' is an alkyl group, provided that either L' or R' has one hydroxyl group. * indicates the bonding position with -NH-.)

[0017] In this embodiment, from the viewpoint of improving the effects of the present invention, the hydroxyl group-containing monoamine compound (A) is preferably a hydroxyl group-containing monoamine compound (A1) represented by the following general formula (a-1-1):

[0018] R １１ -NH-R ２１ ...(a-1-1) (In the general formula (a-1-1), R １１ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２１ is a substituted alkyl group having 1 to 6 carbon atoms and one primary hydroxyl group. ２１-CH of the substituted alkyl group ２ Each - may be independently substituted with -O-.

[0019] In the general formula (a-1-1), R １１ and R ２１ A preferred embodiment of is the above-mentioned R １ and R ２ is the same as:

[0020] Examples of the hydroxyl group-containing monoamine compound (A1) include 3-amino-1-propanol, 4-amino-1-butanol, 5-amino-1-pentanol, 6-amino-1-hexanol, 2-amino-1-propanol, 2-amino-1-butanol, 2-amino-1-pentanol, 2-amino-1-hexanol, 3-amino-1-butanol, 3-amino-1-pentanol, 3-amino-1-hexanol, 4-amino-1-pentanol, 4-amino-1-hexanol, and 5-amino-1-hexanol. ethanol, 2-amino-2-methyl-1-propanol, 2-amino-1-methyl-1-butanol, 2-amino-2-methyl-1-butanol, 2-amino-3-methyl-1-butanol, diglycolamine, 2-(3-aminopropoxy)ethanol, 3-propoxypropylamine, 2-(methylamino)ethanol, 2-(ethylamino)ethanol, 2-(propylamino)ethanol, monobutylethanolamine, 2-(pentylamino)ethanol, 2-(hexylamino)ethanol, etc. Among these, preferred is one or more selected from the group consisting of 2-amino-2-methyl-1-propanol, diglycolamine, 2-(methylamino)ethanol, and monobutylethanolamine.

[0021] From the viewpoint of improving the effects of the present invention, the content of the hydroxyl group-containing monoamine compound (A) is preferably 1 to 99.9 mass%, more preferably 2 to 99.7 mass%, even more preferably 4 to 99.6 mass%, still more preferably 50 to 99.6 mass%, particularly preferably 60 to 99.6 mass%, even more preferably 70 to 99.6 mass%, and even more preferably 80 to 99.6 mass%, based on the total amount of the active ingredients.

[0022] <Other Hydroxyl-Containing Monoamine Compounds (A')> In addition to the hydroxyl-containing monoamine compound (A), the water-soluble heat-treatment oil composition of this embodiment may contain another hydroxyl-containing monoamine compound (A') that does not fall under the general formula (a-1) above, as long as the effects of the present invention are not significantly impaired. Examples of the other hydroxyl-containing monoamine compound (A') include a tertiary hydroxyl-containing monoamine compound and a hydroxyl-containing monoamine compound containing two or more hydroxyl groups. However, from the viewpoint of more easily achieving the effects of the present invention, the content of the other hydroxyl-containing monoamine compound (A') in the water-soluble heat-treatment oil composition of this embodiment is preferably less than 100 parts by mass, more preferably less than 50 parts by mass, even more preferably less than 40 parts by mass, still more preferably less than 35 parts by mass, and even more preferably 30 parts by mass or less, per 100 parts by mass of the hydroxyl-containing monoamine compound (A). Furthermore, from the viewpoint of making it easier to achieve the effects of the present invention, the content of other hydroxyl group-containing monoamine compounds (A') in the water-soluble heat-treated oil composition of this embodiment is preferably less than 90 parts by mass, more preferably less than 80 parts by mass, even more preferably less than 65 parts by mass, even more preferably less than 50 parts by mass, and even more preferably less than 40 parts by mass per 100 parts by mass of the active ingredient.

[0023] <Polyethyleneimine (B)> The water-soluble heat-treated oil composition of this embodiment contains polyethyleneimine (B). It is presumed that polyethyleneimine (B) has the function of adsorbing and aggregating droplets in the emulsion generated by the inclusion of oil components other than the heat-treated oil. Note that one type of polyethyleneimine (B) may be used alone, or two or more types may be used in combination.

[0024] Polyethyleneimine (B) is an ethyleneimine unit (-CH ２ CH ２ In the structure of this polyethyleneimine (B), the hydrogen atom bonded to the nitrogen atom is bonded to the structural unit -CH ２ CH ２When NH- is substituted with another chain, the polyethyleneimine (B) may be branched. Thus, the polyethyleneimine (B) may have not only a completely linear structure but also a branched chain structure containing primary, secondary, and tertiary amino nitrogen atoms, and preferably has a branched chain structure containing primary, secondary, and tertiary amino nitrogen atoms.

[0025] Examples of the polyethyleneimine (B) include diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, and polyethyleneimine having a number-average molecular weight of 300 to 200,000. Among these, from the viewpoint of facilitating the adsorption and aggregation of droplets in the emulsion, polyethyleneimine having a number-average molecular weight of 300 to 200,000 is preferred, polyethyleneimine having a number-average molecular weight of 10,000 to 200,000 is more preferred, polyethyleneimine having a number-average molecular weight of 30,000 to 200,000 is even more preferred, and polyethyleneimine having a number-average molecular weight of 50,000 to 200,000 is even more preferred. Note that the number-average molecular weight of the polyethyleneimine (B) in this specification is a value measured by a viscosity method.

[0026] From the viewpoint of facilitating adsorption and aggregation of droplets in the emulsion, the weight-average molecular weight of the polyethyleneimine (B) is preferably from 50,000 to 1,000,000, more preferably from 80,000 to 800,000, even more preferably from 100,000 to 700,000, and still more preferably from 200,000 to 600,000. The weight-average molecular weight of the polyethyleneimine (B) in this specification is a value measured by the GPC method using pullulan as a standard substance.

[0027] From the viewpoint of improving the effects of the present invention, the content of polyethyleneimine (B) is preferably 0.1 to 99% by mass, more preferably 0.2 to 98% by mass, even more preferably 0.3 to 97% by mass, still more preferably 0.3 to 50% by mass, particularly preferably 0.3 to 40% by mass, even more preferably 0.3 to 30% by mass, even more preferably 0.3 to 25% by mass, and particularly more preferably 0.3 to 20% by mass, based on the total amount of the active ingredients.

[0028] In addition, from the viewpoint of improving rust prevention and making it easier to achieve the effects of the present invention, the water-soluble heat treatment oil composition of this embodiment preferably has a low content of chlorine atom-containing polyethyleneimine.The reason why a lower content of chlorine atom-containing polyethyleneimine makes it easier to achieve the effects of the present invention is not clear, but it is thought that, for example, the chlorine atom reacts with the cationic part of polyethyleneimine, inhibiting the adsorption of droplets with increased anionicity.In the water-soluble heat treatment oil composition of this embodiment, the content of chlorine atoms derived from the chlorine atom-containing polyethyleneimine is preferably less than 1,000 mass ppm, more preferably less than 500 mass ppm, even more preferably less than 100 mass ppm, and even more preferably less than 50 mass ppm, based on the total amount of polyethyleneimine (B).

[0029] <Rust inhibitor (C) and water-soluble polymer (D)> In the water-soluble heat treatment oil composition of this embodiment, in addition to component (A) and component (B), it is preferable to contain at least one of a rust inhibitor (C) and a water-soluble polymer (D), and it is more preferable to contain both. In the following description, the "rust inhibitor (C)" and the "water-soluble polymer (D)" will also be referred to as "component (C)" and "component (D)", respectively.

[0030] <Rust inhibitor (C)> The water-soluble heat treatment oil composition of this embodiment can further improve rust prevention by containing a rust inhibitor (C). The rust inhibitor (C) may be used alone or in combination of two or more. As the rust inhibitor (C), those that have been widely used as additives for heat treatment oils in the past can be used without particular limitation, and examples thereof include carboxylic acids, alkenyl succinic acid half esters, fatty acid soaps, alkyl sulfonates, polyhydric alcohol fatty acid esters, and oxidized paraffins. Among these, from the viewpoint of improving the effects of the present invention, carboxylic acids are preferred as the rust inhibitor (C).

[0031] Examples of carboxylic acids include aliphatic carboxylic acids, alicyclic carboxylic acids, and aromatic carboxylic acids, with aliphatic carboxylic acids being preferred. The hydrocarbon group constituting the aliphatic carboxylic acid may be either a saturated hydrocarbon group or an unsaturated hydrocarbon group, and may be either a straight chain or a branched chain. The carboxylic acid may be a monovalent carboxylic acid or a polyvalent carboxylic acid having two or more carboxylic acids, with polyvalent carboxylic acids being preferred, and dicarboxylic acids being more preferred. The carbon number of the carboxylic acid is preferably 4 or more from the viewpoint of improving rust prevention, and preferably 20 or less from the viewpoint of improving water solubility. The carbon number of the carboxylic acid is preferably 4 to 20, more preferably 6 to 18, and even more preferably 8 to 16. Examples of aliphatic carboxylic acids used as the rust inhibitor (C) include various saturated aliphatic dicarboxylic acids such as various butanedioic acids (the term "various" refers to both linear and branched butanedioic acids, and the same applies hereinafter), various pentanedioic acids, various hexanedioic acids, various heptanedioic acids, various octanedioic acids, various nonanedioic acids, various decanedioic acids, various undecanedioic acids, various dodecanedioic acids, various tridecanedioic acids, various tetradecanedioic acids, various hexadecanedioic acids, various octadecanedioic acids, and various icosane dicarboxylic acids, as well as various unsaturated aliphatic dicarboxylic acids corresponding to these saturated aliphatic dicarboxylic acids (however, the position of the unsaturated bond is optional). Among these, the aliphatic carboxylic acid is preferably various saturated aliphatic dicarboxylic acids, and is preferably one or more selected from the group consisting of various hexanedioic acids, various heptanedioic acids, various octanedioic acids, various nonanedioic acids, various decanedioic acids, various undecanedioic acids, various dodecanedioic acids, various tridecanedioic acids, various tetradecanedioic acids, various hexadecanedioic acids, and various octadecanedioic acids; more preferably one or more selected from the group consisting of various octanedioic acids, various nonanedioic acids, various decanedioic acids, various undecanedioic acids, various dodecanedioic acids, various tridecanedioic acids, various tetradecanedioic acids, and various hexadecanedioic acids; even more preferably various dodecanedioic acids; and even more preferably dodecanedioic acids.

[0032] From the viewpoint of improving the effects of the present invention, the content of the rust inhibitor (C) is preferably 1 to 50 parts by mass, more preferably 3 to 45 parts by mass, even more preferably 5 to 42 parts by mass, and still more preferably 7 to 40 parts by mass, relative to 100 parts by mass of the active ingredient.

[0033] <Water-soluble polymer (D)> The water-soluble heat treatment oil composition of this embodiment contains a water-soluble polymer (D), so that the cooling rate during heat treatment can be adjusted.The water-soluble polymer (D) may be used alone or in combination of two or more.Examples of the water-soluble polymer (D) include polyalkylene glycols such as polyethylene glycol and polypropylene glycol, mono- or dialkyl ethers of polyalkylene glycols, alkylene oxide adducts of polyalkylene glycols such as ethylene oxide (EO), propylene oxide (PO), and polyhydric alcohol alkylene oxide adducts, polyvinylpyrrolidones, and methylcelluloses.However, from the viewpoint of improving stickiness resistance, polyalkylene glycols are preferred.

[0034] Specific examples of the polyalkylene glycols include linear polyalkylene glycols (D1) and branched polyhydric alcohol alkylene oxide adducts (D2).

[0035] <Straight-chain polyalkylene glycols (D1)> The straight-chain polyalkylene glycols (D1) can be any polymer of alkylene glycol without any particular limitation, but preferred examples include at least one selected from the group consisting of straight-chain polyalkylene glycols (D1-1) represented by the following general formula (d-1): ｄ１ O-(L ｄ１ O) ｎ -R ｄ２ ... (d-1)

[0036] In the above general formula (d-1), R ｄ１ and R ｄ２each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an acyl group having 1 to 11 carbon atoms, or an optionally substituted saturated or unsaturated alicyclic hydrocarbon group or aromatic hydrocarbon group having 5 to 18 carbon atoms.

[0037] R ｄ１ and R ｄ２ Examples of the alkyl group having 1 to 10 carbon atoms represented by R include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group. ｄ１ and R ｄ２ The acyl group having 1 to 11 carbon atoms represented by R includes an acyl group having an alkyl group having 1 to 10 carbon atoms and a carbonyl group. ｄ１ and R ｄ２ Examples of the saturated alicyclic hydrocarbon group having 5 to 18 carbon atoms represented by R include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecyl group. ｄ１ and R ｄ２ Examples of the unsaturated alicyclic hydrocarbon group having 5 to 18 carbon atoms represented by R include a cyclopentenyl group and a cyclohexenyl group. ｄ１ and R ｄ２ Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the formula (I) include aryl groups such as a phenyl group and a naphthyl group. Examples of the substituent that the alicyclic hydrocarbon group or aromatic hydrocarbon group may have include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and an aryl group having 6 to 14 carbon atoms.

[0038] In addition, in the general formula (d-1), (L ｄ１O) is an alkylene oxide having 2 to 6 carbon atoms, and examples of the alkylene oxide include ethylene oxide (hereinafter also referred to as "EO"), propylene oxide (hereinafter also referred to as "PO"), oxetane, 1,2-butylene oxide, 2,3-butylene oxide, 1,3-butylene oxide, and tetrahydrofuran. Among these, a combination of EO and PO is preferred. Furthermore, in the above general formula (d-1), n ​​is an integer of 1 or more, and from the viewpoint of handleability, n is preferably an integer of 1 to 2500, more preferably an integer of 5 to 2000, even more preferably an integer of 10 to 1500, and even more preferably an integer of 100 to 800.

[0039] (L ｄ１ When there are a plurality of (L O) units, i.e., when n ≥ 2, each (L ｄ１ O) units may be the same or different. ｄ１ When the L) units are different, they may be either random or block, but the random type is preferred from the viewpoint of ease of handling. ｄ１ When a combination of EO and PO is used as O, the monomer composition ratio of EO to PO (EO:PO) is preferably 50:50 to 95:5 in molar ratio, more preferably 60:40 to 90:10, and even more preferably 65:35 to 85:15, from the viewpoint of ensuring appropriate water solubility of the water-soluble polymer (D).Furthermore, the monomer composition ratio of EO to PO (EO:PO) is preferably 43:57 to 94:6 in mass ratio, more preferably 53:47 to 87:13, and even more preferably 58:42 to 81:19, from the viewpoint of ensuring appropriate water solubility of the water-soluble polymer (D).

[0040] A more specific embodiment of the linear polyalkylene glycol (D1) is (L ｄ１ O) units are composed of one kind of alkylene oxide such as ethylene oxide, propylene oxide, and butylene oxide, and R ｄ１ and R ｄ２ is a hydrogen atom; ｄ１O) units are composed of two or more alkylene oxides selected from ethylene oxide, propylene oxide, butylene oxide, etc., and R ｄ１ and R ｄ２ is a hydrogen atom; ｄ１ and R ｄ２ and a linear polyalkylene glycol derivative in which at least one of the groups is an alkyl group having 1 to 10 carbon atoms, an acyl group having 1 to 11 carbon atoms, or an optionally substituted saturated or unsaturated alicyclic hydrocarbon group or aromatic hydrocarbon group having 5 to 18 carbon atoms. In this specification, of the compounds represented by the general formula (d-1), those in which both terminals are hydrogen are referred to as polyalkylene glycols, and those in which at least one terminal is other than hydrogen are referred to as polyalkylene glycol derivatives. Furthermore, the linear polyalkylene glycols (D1) are a comprehensive concept that includes the polyalkylene glycols and the polyalkylene glycol derivatives.

[0041] <Branched Polyhydric Alcohol Alkylene Oxide Adduct (D2)> The branched polyhydric alcohol alkylene oxide adduct (D2) can be used without any particular limitation, but is preferably a branched polyhydric alcohol alkylene oxide adduct (D2-1) which is a mixed adduct of alkylene oxides having 2 to 3 carbon atoms and has a mass average molecular weight of 10,000 or more.

[0042] In the molecule of the branched polyhydric alcohol alkylene oxide adduct (D2-1), the ratio of the number of alkylene oxide units having 2 carbon atoms (the number of ethylene oxide units) to the number of alkylene oxide units having 3 carbon atoms (the number of propylene oxide units) (EO:PO) is preferably 50:50 to 90:10, more preferably 60:40 to 85:15, and even more preferably 65:35 to 80:20, from the viewpoints of cooling rate and solubility in water.

[0043] The polyhydric alcohol used as a raw material for the branched polyhydric alcohol alkylene oxide adduct (D2-1) is not particularly limited as long as it has three or more hydroxyl groups, but the number of hydroxyl groups is preferably 3 to 8, more preferably 3 to 6, and even more preferably 3 to 4. From the viewpoint of solubility in water, the polyhydric alcohol used as a raw material for the branched polyhydric alcohol alkylene oxide adduct (D2-1) preferably has 3 to 10 carbon atoms, more preferably 3 to 6, and even more preferably 3 to 4. Specific examples of the polyhydric alcohol used as a raw material include glycerin, diglycerin, trimethylolpropane, and pentaerythritol, and among these, glycerin is preferred.

[0044] In this embodiment, the water-soluble polymer (D) preferably contains at least one selected from the group consisting of linear polyalkylene glycols (D1) and branched polyhydric alcohol alkylene oxide adducts (D2).

[0045] The mass average molecular weight of the water-soluble polymer (D) is preferably 5,000 to 100,000, more preferably 7,500 to 50,000, and even more preferably 10,000 to 30,000, from the viewpoints of easily suppressing changes in the cooling rate when the water-soluble polymer (D) is subjected to repeated heat treatment, and improving the ability to adjust the cooling rate and ease of handling. Furthermore, the molecular weight distribution (Mw / Mn), which is the ratio of the mass average molecular weight to the number average molecular weight (Mn) of the water-soluble polymer (D), is preferably 1.5 to 5.0, more preferably 2.0 to 4.0, and even more preferably 2.5 to 3.5. The polyalkylene glycols may be used alone or in combination of two or more. Furthermore, the polyalkylene glycols may be L ｄ１ A mixture of various structures having different types of O, constituent ratios, etc. may be used. The mass average molecular weight and molecular weight distribution (Mw / Mn) of the water-soluble polymer (D) in this specification are values ​​measured by the method described in the examples below.

[0046] From the viewpoint of improving the effects of the present invention, the content of the water-soluble polymer (D) is preferably 100 to 7,000 parts by mass, more preferably 100 to 1,000 parts by mass, even more preferably 150 to 900 parts by mass, still more preferably 200 to 800 parts by mass, particularly preferably 250 to 750 parts by mass, and even more preferably 300 to 700 parts by mass, relative to 100 parts by mass of the active ingredient.

[0047] <Water> The water-soluble heat-treated oil composition of the present embodiment may be a water-free concentrate, or may contain water. The water is not particularly limited, and purified water such as distilled water or ion-exchanged water (deionized water); tap water; industrial water; etc. can be used.

[0048] The content of water is appropriately adjusted according to the use mode of the water-soluble heat-treatment oil composition.For example, when the water-soluble heat-treatment oil composition of this embodiment is subjected to heat treatment, the water content of the water-soluble heat-treatment oil composition (hereinafter also referred to as "the content of water of the first embodiment") is, from the viewpoint of improving the cooling performance of the water-soluble heat-treatment oil composition, from the viewpoint of improving the flame retardancy of the water-soluble heat-treatment oil composition and improving safety, and from the viewpoint of reducing the viscosity of the water-soluble heat-treatment oil composition and improving its handleability, based on the total amount of the water-soluble heat-treatment oil composition (100 mass%), preferably 70.0 mass% or more, more preferably 75.0 mass% or more, even more preferably 80.0 mass% or more, even more preferably 85.0 mass% or more, particularly preferably 88.5 mass% or more.And, from the viewpoint of ensuring the amount of effective ingredients in the water-soluble heat-treatment oil composition, it is preferably 99.9 mass% or less, more preferably 99.8 mass% or less, even more preferably 99.7 mass% or less, even more preferably 99.5 mass% or less, particularly preferably 99.3 mass% or less. In addition, the water-soluble heat-treated oil composition of this embodiment is preferably a stock solution that does not contain water from the viewpoint of transportation efficiency, but from the viewpoint of ensuring safety and stability, the stock solution may be diluted with the minimum amount of water required at the distribution stage, and further diluted with water when used.When the stock solution is diluted with water at the distribution stage, the water content (the water content of the second embodiment) is preferably 30 mass% or more, more preferably 35 mass% or more, even more preferably 40 mass% or more, and even more preferably 45 mass% or more, based on the total amount of the water-soluble heat-treated oil composition as 100 mass%.And, from the viewpoint of ensuring the amount of active ingredient in the water-soluble heat-treated oil composition, it is preferably 85 mass% or less, more preferably 83 mass% or less, even more preferably 81 mass% or less, and even more preferably 78 mass% or less.

[0049] <Content of hydroxyl group-containing monoamine compound (A)> When the water content of the water-soluble heat-treated oil composition of this embodiment is the water content of the first embodiment, the content of component (A) is, from the viewpoint of making it easier to improve the effects of the present invention, based on the total amount of the water-soluble heat-treated oil composition (100 mass%), preferably 0.001 mass% or more, more preferably 0.003 mass% or more, even more preferably 0.15 mass% or more, even more preferably 0.30 mass% or more, particularly preferably 0.50 mass% or more. Also, from the viewpoint of making it easier to improve the effects of the present invention, the content of component (A) is, based on the total amount of the water-soluble heat-treated oil composition (100 mass%), preferably 8.0 mass% or less, more preferably 6.0 mass% or less, even more preferably 4.0 mass% or less.

[0050] <Content of polyethyleneimine (B)> When the water content of the water-soluble heat-treated oil composition of this embodiment is the water content of the first aspect, the content of component (B) is, from the viewpoint of making it easier to improve the effects of the present invention, based on the total amount of the water-soluble heat-treated oil composition (100 mass%), preferably 0.0025 mass% or more, more preferably 0.005 mass% or more, and even more preferably 0.008 mass% or more. Also, from the viewpoint of making it easier to improve the effects of the present invention, the content of component (B) is, based on the total amount of the water-soluble heat-treated oil composition, preferably 0.4 mass% or less, more preferably 0.3 mass% or less, and even more preferably 0.25 mass% or less.

[0051] <Ratio of Hydroxyl Group-Containing Monoamine Compound (A) to Polyethyleneimine (B) [(A) / (B)]> In the water-soluble heat-treated oil composition of this embodiment, the ratio of the component (A) acting on a single droplet to the component (B) adsorbing multiple droplets is appropriately set, and both components act in just the right amount, thereby further improving the effects of the present invention. From the viewpoint of facilitating the enhancement of the effects of the present invention, [(A) / (B)] is preferably 0.01 or more, more preferably 0.03 or more, even more preferably 1 or more, even more preferably 2 or more, particularly preferably 3 or more, and even more preferably 4 or more, in terms of mass ratio. It is also preferably 250 or less, more preferably 230 or less, even more preferably 210 or less, and even more preferably 205 or less. The upper and lower limits of these numerical ranges can be arbitrarily combined. Specifically, it is preferably 0.01 to 250, more preferably 0.03 to 250, even more preferably 1 to 250, even more preferably 2 to 230, particularly preferably 3 to 210, and even more preferably 4 to 205.

[0052] <Content of rust inhibitor (C)> When the water content of the water-soluble heat-treated oil composition of this embodiment is the water content of the first embodiment, the content of component (C) is, from the viewpoint of making it easier to improve the effects of the present invention, based on the total amount of the water-soluble heat-treated oil composition (100 mass%), preferably 0.001 mass% or more, more preferably 0.005 mass% or more, even more preferably 0.01 mass% or more, and even more preferably 0.02 mass% or more. Also, from the viewpoint of making it easier to improve the effects of the present invention, the content of component (C) is, based on the total amount of the water-soluble heat-treated oil composition, preferably 1.2 mass% or less, more preferably 1.0 mass% or less, even more preferably 0.9 mass% or less, and even more preferably 0.7 mass% or less.

[0053] <Ratio of Hydroxyl Group-Containing Monoamine Compound (A) to Rust Inhibitor (C) [(A) / (C)]> In the water-soluble heat treatment oil composition of this embodiment, from the viewpoint of further improving the effects of the present invention, the mass ratio [(A) / (C)] is preferably 0.5 or more, more preferably 1 or more, even more preferably 1.5 or more, and even more preferably 2 or more. It is also preferably 100 or less, more preferably 70 or less, even more preferably 40 or less, and even more preferably 20 or less. The upper and lower limits of these numerical ranges can be arbitrarily combined. Specifically, it is preferably 0.5 to 100, more preferably 1 to 70, even more preferably 1.5 to 40, and even more preferably 2 to 20.

[0054] <Content of water-soluble polymer (D)> When the water content of the water-soluble heat-treated oil composition of this embodiment is the water content of the first embodiment, the content of component (D) is, from the viewpoint of making it easier to improve the effects of the present invention, based on the total amount of the water-soluble heat-treated oil composition (100 mass%), preferably 0.5 mass% or more, more preferably 1.0 mass% or more, and even more preferably 1.2 mass% or more. Also, from the viewpoint of making it easier to improve the effects of the present invention, the content of component (D) is, based on the total amount of the water-soluble heat-treated oil composition, preferably 15.0 mass% or less, more preferably 13.5 mass% or less, and even more preferably 12.0 mass% or less.

[0055] <Other Components> The water-soluble heat treatment oil composition of this embodiment may contain components other than the hydroxyl group-containing monoamine compound (A), polyethyleneimine (B), rust inhibitor (C), water-soluble polymer (D), and water (hereinafter also referred to as "other components"), within a range that does not significantly impair the effects of the present invention. Examples of such other components include corrosion inhibitors such as benzotriazole and tolyltriazole, copper deactivators, antioxidants, silicone-based antifoaming agents, colorants, and inorganic acid salts such as potassium hydroxide, sodium nitrite, and potassium pyrophosphate.

[0056] When the water-soluble heat-treated oil composition of this embodiment contains other components, the total content of the other components may be 0.1 parts by mass or more, 0.2 parts by mass or more, or 0.3 parts by mass or more, relative to 100 parts by mass of the active ingredient, or 30 parts by mass or less, 20 parts by mass or less, 10 parts by mass or less, 5 parts by mass or less, or 3 parts by mass or less.

[0057] [Method for producing water-soluble heat-treatment oil composition] The method for producing the water-soluble heat-treatment oil composition of this embodiment is not particularly limited. For example, the method for producing the water-soluble heat-treatment oil composition of this embodiment is a method for producing a water-soluble heat-treatment oil composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1) and a polyethyleneimine (B), and includes a step of mixing the hydroxyl group-containing monoamine compound (A) and the polyethyleneimine (B). R １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each - may be independently substituted with -O-.

[0058] Another method for producing a water-soluble heat-treatment oil composition according to the present embodiment is a method for producing a water-soluble heat-treatment oil composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1), polyethyleneimine (B), and water, and includes a step of mixing the hydroxyl group-containing monoamine compound (A), the polyethyleneimine (B), and the water. １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２Each - may be independently substituted with -O-.) The order in which component (A), component (B), and water are mixed is not particularly limited. For example, components (A) and (B) may be mixed sequentially or simultaneously with water, or components (A) and (B) may be mixed in advance and the resulting mixture may be mixed with water. Furthermore, a composition containing water and either component (A) or component (B) but not the other may be mixed with either component (A) or component (B) that is not contained in the composition. Furthermore, in this production method, components (A) and (B) may be mixed with water, and then, as necessary, components (C), (D), and other components may be further mixed. In such cases, the order in which the components are mixed, the method of mixing, etc. are not particularly limited. Note that components (A), (B), (C), (D), water, and other components are the same as those described above, and preferred embodiments thereof are also the same, so detailed description thereof will be omitted. Furthermore, the suitable amounts of component (A), component (B), component (C), component (D), water, and other components, and the suitable ratios of amounts of each component, are the same as the respective contents and content ratios in the water-soluble heat-treated oil composition described above, and therefore detailed explanations thereof will be omitted.

[0059] [Uses of Water-Soluble Heat Treatment Oil Composition] The water-soluble heat treatment oil composition of this embodiment can be used for heat treatments such as quenching, tempering, annealing, and normalizing. Furthermore, the water-soluble heat treatment oil composition of this embodiment has excellent oil separation properties. Therefore, the water-soluble heat treatment oil composition of this embodiment can be suitably used as a quenching oil or tempering oil for metal members processed with metal processing oils containing strong emulsifiers, etc., and is more preferably used as a quenching oil. The metal processing oil preferably includes an emulsion-type water-soluble metal processing oil composition and a soluble-type water-soluble metal processing oil composition.

[0060] [Oil Separation Method] As described above, the water-soluble heat treatment oil composition of this embodiment contains a hydroxyl-containing monoamine compound (A) and polyethyleneimine (B) having specific structures, and therefore has excellent oil-separating properties. However, even if the water-soluble heat treatment oil composition does not contain the hydroxyl-containing monoamine compound (A) but contains polyethyleneimine (B), by contacting the water-soluble heat treatment oil composition with another composition containing the hydroxyl-containing monoamine compound (A), the hydroxyl-containing monoamine compound (A) in the composition is mixed into the water-soluble heat treatment oil composition, thereby exhibiting oil-separating properties. That is, even if a water-soluble heat treatment oil composition containing polyethyleneimine (B) but not the hydroxyl-containing monoamine compound (A) is used as an active ingredient for a metal component having oil, such as a metalworking oil containing the hydroxyl-containing monoamine compound (A), in a stage prior to a heat treatment process such as a cutting process, the oil mixed into the water-soluble heat treatment oil composition can be separated. Therefore, in this embodiment, the following oil separation method is provided. A method for separating oil, comprising a step of contacting a water-soluble heat-treated oil composition containing polyethyleneimine (B) with a composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1): １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each - may independently be substituted by -O-.) The water-soluble heat treatment oil composition containing the polyethyleneimine (B) does not need to contain the hydroxyl group-containing monoamine compound (A), but from the viewpoint of promoting oil separation, it preferably contains the hydroxyl group-containing monoamine compound (A). Furthermore, preferred compositions containing the hydroxyl group-containing monoamine compound (A) include emulsion-type water-soluble metal working oil compositions and soluble-type water-soluble metal working oil compositions.

[0061] [One Aspect of the Present Invention Provided] In one aspect of the present invention, the following [1] to

[14] are provided. [1] A water-soluble heat treatment oil composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1) and polyethyleneimine (B). R １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each of - may be independently substituted with -O-. ２ [3] In the general formula (a-1), one of the hydroxyl groups is a primary hydroxyl group. １ [4] The water-soluble heat treatment oil composition according to [1] or [2], wherein the hydroxyl group-containing monoamine compound (A) is a hydroxyl group-containing monoamine compound (A1) represented by the following general formula (a-1-1): １１ -NH-R ２１ ...(a-1-1) (In the general formula (a-1-1), R １１ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２１ is a substituted alkyl group having 1 to 6 carbon atoms and one primary hydroxyl group. ２１ -CH of the substituted alkyl group ２Each - may be independently substituted by -O-.) [5] The water-soluble heat treatment oil composition according to any one of [1] to [4], wherein the polyethyleneimine (B) has a number-average molecular weight of 10,000 to 200,000. [6] The water-soluble heat treatment oil composition according to any one of [1] to [5], further containing water. [7] The water-soluble heat treatment oil composition according to any one of [1] to [6], further containing a rust inhibitor (C). [8] The water-soluble heat treatment oil composition according to any one of [1] to [7], further containing a water-soluble polymer (D). [9] The water-soluble heat treatment oil composition according to any one of [1] to [8], wherein the content ratio [(A) / (B)] of the hydroxyl group-containing monoamine compound (A) to the polyethyleneimine (B) is 0.01 to 250 by mass.

[10] The water-soluble heat treatment oil composition according to any one of [1] to [9], wherein the water-soluble heat treatment oil composition is used as a quenching oil or a tempering oil.

[11] A method for using the water-soluble heat treatment oil composition according to any one of [1] to

[10] as a quenching oil or tempering oil.

[12] A method for producing a water-soluble heat treatment oil composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1) and a polyethyleneimine (B), the method comprising the step of mixing the hydroxyl group-containing monoamine compound (A) and the polyethyleneimine (B). R １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each of the - may be independently substituted with -O-.)

[13] A method for producing a water-soluble heat-treatment oil composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1), a polyethyleneimine (B), and water, the method comprising the step of mixing the hydroxyl group-containing monoamine compound (A), the polyethyleneimine (B), and the water. R １ -NH-R ２...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each of the - may be independently substituted with -O-.)

[14] A method for separating oil, comprising a step of contacting a water-soluble heat-treated oil composition containing polyethyleneimine (B) with a composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1): １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each - may be independently substituted with -O-.

[0062] The present invention will be specifically described with reference to the following examples, although the present invention is not limited to the following examples.

[0063] [Methods for Measuring Various Physical Properties] Measurements of the various properties of the raw materials used in each Example and Comparative Example and the lubricating oil compositions of each Example and Comparative Example were carried out according to the procedures set out below.

[0064] (1) Mass-average molecular weight (Mw) and molecular weight distribution (Mw / Mn) of component (D) were measured in accordance with JIS K7252-1:2016. Two columns (manufactured by Tosoh Corporation, product name "TSKgel GMPWXL") were attached to a refractive index (RI) detector (manufactured by JASCO Corporation, product name "RI-1530"), and polyethylene oxide (4.2 x 10 ２ ~1.1 x 10 ６ The measurement was carried out using a 0.2 M aqueous sodium nitrate solution (g / mol) under the conditions of a solvent, a flow rate of 1.0 mL / min, a sample concentration of 0.3 w / v %, and a temperature of 40°C.

[0065] [Examples 1 to 31, Comparative Examples 1 to 22] The following components were mixed to prepare water-soluble heat-treated oil compositions having the compositions shown in Tables 1 to 5, and the evaluations described below were carried out. Details of each component used in preparing the water-soluble heat-treated oil compositions having the compositions shown in Tables 1 to 5 are described below.

[0066] <Component (A)> Component (A)-1: Diglycolamine Component (A)-2: 2-amino-2-methyl-1-propanol Component (A)-3: 2-(methylamino)ethanol Component (A)-4: 1-amino-2-propanol Component (A)-5: Butylethanolamine Component (A')-1: Cyclohexyldiethanolamine Component (A')-2: Triethanolamine Component (A')-3: Diethanolamine Component (A')-4: N-(2-hydroxyethyl)piperazine Component (A')-5: N-methyldiethanolamine Component (A')-6: Triisopropanolamine Component (A')-7: 2-amino-2-ethyl-1,3-propanediol

[0067] <Component (B)> Component (B)-1: polyethyleneimine, solid content 30% by mass, number average molecular weight 70,000, mass average molecular weight 350,000 Component (B)-2: polyethyleneimine, solid content 35% by mass, number average molecular weight 100,000, mass average molecular weight 450,000 The number average molecular weight is a value measured by a viscosity method, and the mass average molecular weight is a value measured by a GPC method using pullulan as a standard substance.

[0068] <Component (C)> Rust inhibitor: dodecanedioic acid

[0069] <Component (D)> Water-soluble polymer: mixed adduct of ethylene oxide and propylene oxide with glycerin, Mw=15,000, Mw / Mn=2.7, number of ethylene oxide units: number of propylene oxide units=72:28)

[0070] <Water> ・Ion-exchanged water

[0071] [Evaluation Method] The water-soluble heat-treated oil compositions obtained in Examples 1 to 31 and Comparative Examples 1 to 22 were subjected to the tests described below to evaluate oil separation properties.

[0072] <Oil Separability Test> 100 g of the water-soluble heat treatment oil composition was placed in a 200 mL beaker, followed by 2 g of the water-soluble metal working oil composition shown below. The mixture was mixed with a stirrer at 400 rpm for 5 minutes and allowed to stand at room temperature for 1 day. The oil separation state of the water-soluble heat treatment oil composition after standing for 1 day was evaluated according to the following criteria, with ratings S and A being considered pass and ratings B and C being considered fail. S: The color of the water layer lightened, and the water-soluble metal working oil composition separated into the upper layer, resulting in good oil separability. A: The color of the water layer lightened, or the water-soluble metal working oil composition separated into the upper layer or aggregated, resulting in somewhat good oil separability. B: The color of the water layer lightened slightly, and a trace amount of the water-soluble metal working oil composition separated into the upper layer or aggregated, resulting in somewhat poor oil separability. C: The water-soluble metal working oil composition was emulsified, and the test liquid was cloudy overall, resulting in poor oil separability.

[0073] <Water-soluble metalworking oil compositions> The water-soluble metalworking oil compositions used in this test are as follows: Water-soluble metalworking oil composition 1: Daphne Alphacool EX-1 (manufactured by Idemitsu Kosan Co., Ltd., emulsion type) Water-soluble metalworking oil composition 2: Daphne Alphacool EW-A (manufactured by Idemitsu Kosan Co., Ltd., emulsion type) Water-soluble metalworking oil composition 3: Daphne Mircoul AL (manufactured by Idemitsu Kosan Co., Ltd., emulsion type, containing 0.25 to 1 mass % of 2-aminomethanol)

[0074] The properties and evaluation results of each water-soluble metalworking oil composition are shown in Tables 1 to 5. In Tables 1 and 2, water-soluble metalworking oil composition 1 was used, in Table 3, water-soluble metalworking oil composition 2 was used, and in Tables 4 and 5, water-soluble metalworking oil composition 3 was used.

[0075] <Evaluation Results> Tables 1 to 5 reveal the following. The results shown in Examples 1 to 29 reveal that water-soluble heat treatment oil compositions containing a hydroxyl group-containing monoamine compound (A) and polyethyleneimine (B) have excellent oil separability relative to any of the water-soluble metalworking oils. In contrast, the results shown in Comparative Examples 1 to 22 reveal that water-soluble heat treatment oil compositions that do not contain at least one of a hydroxyl group-containing monoamine compound (A) and polyethyleneimine (B) have insufficient oil separability. Furthermore, the results shown in Examples 30 to 31 reveal that water-soluble metalworking oil composition 3 containing a hydroxyl group-containing monoamine compound (A) can separate oil even when mixed with a water-soluble heat treatment oil composition that does not contain a hydroxyl group-containing monoamine compound (A) but contains polyethyleneimine (B).

Claims

1. A water-soluble heat treatment oil composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1) and polyethyleneimine (B): １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each - may be independently substituted with -O-.

2. In the general formula (a-1), R ２ 2. The water-soluble heat treatment oil composition according to claim 1, wherein one of the hydroxyl groups is a primary hydroxyl group.

3. In the general formula (a-1), R １ The water-soluble heat treatment oil composition according to claim 1 or 2, wherein is a hydrogen atom.

4. The water-soluble heat treatment oil composition according to claim 1, wherein the hydroxyl group-containing monoamine compound (A) is a hydroxyl group-containing monoamine compound (A1) represented by the following general formula (a-1-1): １１ -NH-R ２１ ...(a-1-1) (In the general formula (a-1-1), R １１ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２１ is a substituted alkyl group having 1 to 6 carbon atoms and one primary hydroxyl group. ２１ -CH of the substituted alkyl group ２ Each - may be independently substituted with -O-.

5. A water-soluble heat treatment oil composition according to any one of claims 1 to 4, wherein the polyethyleneimine (B) has a number average molecular weight of 10,000 to 200,000.

6. The water-soluble heat treatment oil composition according to any one of claims 1 to 5, further comprising water.

7. The water-soluble heat treatment oil composition according to any one of claims 1 to 6, further comprising a rust inhibitor (C).

8. The water-soluble heat treatment oil composition according to any one of claims 1 to 7, further comprising a water-soluble polymer (D).

9. A water-soluble heat treatment oil composition according to any one of claims 1 to 8, wherein the content ratio of the hydroxyl group-containing monoamine compound (A) to the polyethyleneimine (B) [(A) / (B)] is 0.01 to 250 in mass ratio.

10. The water-soluble heat treatment oil composition according to any one of claims 1 to 9, which is used as a quenching oil or a tempering oil.

11. A method of using the water-soluble heat treatment oil composition according to any one of claims 1 to 10 as a quenching oil or tempering oil.

12. A method for producing a water-soluble heat-treatment oil composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1) and a polyethyleneimine (B), the method comprising the step of mixing the hydroxyl group-containing monoamine compound (A) and the polyethyleneimine (B): １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each - may be independently substituted with -O-.

13. A method for producing a water-soluble heat-treatment oil composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1), polyethyleneimine (B), and water, the method comprising the step of mixing the hydroxyl group-containing monoamine compound (A), the polyethyleneimine (B), and the water. R １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each - may be independently substituted with -O-.

14. A method for separating oil, comprising a step of contacting a water-soluble heat-treated oil composition containing polyethyleneimine (B) with a composition containing a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1): １ -NH-R ２ ...(a-1) (In the general formula (a-1), R １ is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and R ２ is a substituted alkyl group having one hydroxyl group, provided that R ２ -CH of the substituted alkyl group ２ Each - may be independently substituted with -O-.

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