Water-soluble heat treatment oil composition

Abstract

To provide a water-soluble heat treatment oil composition having excellent oil separation properties.SOLUTION: The water-soluble heat treatment oil composition contains a hydroxy group-containing monoamine compound (A) represented by general formula (a-1) and polyethyleneimine (B). R1-NH-R2 (a-1) (in the general formula (a-1), R1 is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and R2 is a substituted alkyl group having one hydroxyl group). Here, - R2 - of the substituted alkyl group in CH2 may be each independently substituted with - O -. ) SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Metal parts such as gears are generally formed through cutting processes and then heat treated to adjust the hardness, toughness, etc., of the finished product. In the cutting process, oil-soluble metalworking oils and water-soluble metalworking oils are used, but these metalworking oils cannot be completely removed by the cleaning process and may remain on the surface of the metal material. Also, if there is a period between the cutting process and the heat treatment process, or if the two processes are performed in different locations, rust preventative oil is applied to the metal material after the cutting process. When these metal processing oils, rust preventative oils, etc. are mixed into the water-soluble heat treatment oil composition used as a coolant in the heat treatment process, they emulsify and the state of the water-soluble heat treatment oil composition changes significantly. 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. In addition, the water-soluble heat treatment oil composition becomes susceptible to spoilage by microorganisms, resulting in a short 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). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2012-153809 Summary of the Invention [Problem to be solved by the invention]

[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. [Means for solving the problem]

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

[0007] According to the present invention, the following [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): 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 In the above, each —CH— in the substituted alkyl group 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), A method for producing a water-soluble heat-treated oil composition, 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), R1 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 In the above, each —CH— in the substituted alkyl group 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), polyethyleneimine (B), and water, A method for producing a water-soluble heat-treated oil composition, 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 In the above, each —CH— in the substituted alkyl group 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): 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 In the above, each —CH— in the substituted alkyl group may be independently substituted with —O—. [Effects of the Invention]

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

[0009] The upper and lower limits of the ranges described herein can be combined in any way. For example, if the ranges are "A to B" and "C to D," the ranges "A to D" and "C to B" are also included in the scope of the present invention. Furthermore, unless otherwise specified, 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. 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. In addition, the "hydroxyl group-containing monoamine compound (A)" and the "polyethyleneimine (B)" are collectively referred to as the "active ingredients," and the total content of the "hydroxyl group-containing monoamine compound (A)" and the "polyethyleneimine (B)" is also referred to as the "total amount of active ingredients."

[0011] [Embodiments of the water-soluble heat-treated oil composition] The water-soluble heat-treated oil composition of this embodiment contains 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 In the above, each —CH— in the substituted alkyl group may be independently substituted with —O—.

[0012] The present inventors have conducted extensive research to solve the above problems. As a result, the present inventors discovered that a water-soluble heat-treated oil composition containing the above components has excellent oil-separating properties, and after further investigations, they have completed the present invention. The reason why the water-soluble heat-treated oil composition of this embodiment has excellent oil separation properties is not clear, but it is presumed to be due to the following mechanism. Specifically, 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 the emulsifier in the oil. For example, if the emulsifier is an anionic surfactant, the hydrophilic group of the anionic surfactant exchanges with component (A), and the fatty acid or other component constituting the anionic surfactant forms a salt with component (A). Component (A) contains primary or secondary amine groups, and these amine groups have strong bonding strength with fatty acids or other components, resulting in high ionicity of the salt formed between component (A) and the fatty acid or other component constituting the anionic surfactant. This improves the anionicity of the droplet surfaces in the emulsion, leading to adsorption and aggregation of many droplets onto the polycation component (B). Furthermore, since component (A) has only one hydroxyl group, its hydrophilicity is relatively low. Therefore, when the hydrophilic group of the anionic surfactant exchanges with component (A), the balance between hydrophilicity and lipophilicity of the droplet surfaces is disrupted, resulting in an unstable droplet membrane. From the above, it is presumed that component (B) causes the aggregated droplets to coalesce, destroying the unstable droplet membrane, causing the droplets to become larger in size, making it easier for the oil to separate.

[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 R2 is a substituted alkyl group having one hydroxyl group, provided that R 2 In the above, each —CH— in the substituted alkyl group may be independently substituted with —O—. It is presumed that the hydroxyl group-containing monoamine compound (A) exchanges with the hydrophilic group moiety of the emulsifier, etc., in the oil mixed into the water-soluble heat-treated oil composition of this embodiment, destabilizing the droplet film and making it easier for the droplets to coalesce, thereby contributing to improved oil separation properties. 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. R 1 When the alkyl group 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 fatty acids and the like is likely to be improved. R 1 The alkyl group having 1 to 6 carbon atoms that can be selected as may be either linear or branched. Here, from the viewpoint of facilitating further improvement of the bonding strength of the hydroxyl group-containing monoamine compound (A) with a fatty acid or the like, R 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 In the above-mentioned substituted alkyl groups, each -CH2- 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), it is preferably a primary or secondary hydroxyl group, and more preferably a primary hydroxyl group. When the alkyl group has only one hydroxyl group, the hydrophilicity of the hydroxyl group-containing monoamine compound (A) can be kept relatively low, and water solubility can be easily imparted to the compound. R 2 The substituted alkyl group that can be selected as may be either linear or branched. R 2 The number of carbon atoms in the substituted alkyl group that can be selected as 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. Also, R 2 Each -CH2- in the substituted alkyl group may be independently substituted with -O-, for example, R 2 When one of the -CH2- in the substituted alkyl group in R is replaced with -O-, 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. However, 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 21is a substituted alkyl group having 1 to 6 carbon atoms and one primary hydroxyl group, provided that R 21 In the above, each —CH— in the substituted alkyl group may be independently substituted with —O—.

[0019] In the general formula (a-1-1), R 11 and R 21 A preferred embodiment of the above is 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. amine, 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, and the like. Among these, one or more selected from the group consisting of 2-amino-2-methyl-1-propanol, diglycolamine, 2-(methylamino)ethanol, and monobutylethanolamine are preferred.

[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 group-containing monoamine compounds (A')> The water-soluble heat-treatment oil composition of this embodiment may contain, in addition to the hydroxyl group-containing monoamine compound (A), other hydroxyl group-containing monoamine compounds (A') that do not correspond to the above general formula (a-1), within a range that does not significantly impair the effects of the present invention. Examples of the other hydroxyl group-containing monoamine compounds (A') include tertiary hydroxyl group-containing monoamine compounds and hydroxyl group-containing monoamine compounds containing two or more hydroxyl groups. However, from the viewpoint of making it easier to exert the effects of the present invention, the content of the other hydroxyl group-containing monoamine compound (A') in the water-soluble heat-treated 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 group-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), which is presumed to have the function of adsorbing and aggregating droplets in the emulsion generated by the inclusion of oils other than the heat-treated oil. The polyethyleneimine (B) may be used singly or in combination of two or more kinds.

[0024] Polyethyleneimine (B) is a compound with -CH2CH2NH- as a structural unit. In the structure of this polyethyleneimine (B), branching may occur when a hydrogen atom bonded to a nitrogen atom is replaced by another chain of the structural unit -CH2CH2NH-. Therefore, polyethyleneimine (B) includes not only those having a completely linear structure but also those having a branched chain structure containing primary, secondary, and tertiary amino nitrogen atoms.

[0025] Examples of polyethyleneamine (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 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. The number average molecular weight of the polyethyleneimine (B) in this specification is a value measured by a viscosity method.

[0026] Furthermore, from the viewpoint of facilitating adsorption and aggregation of droplets in the emulsion, the weight average molecular weight of the polyethyleneimine (B) is preferably 50,000 or more and 1,000,000 or less, more preferably 80,000 or more and 800,000 or less, even more preferably 100,000 or more and 700,000 or less, and still more preferably 200,000 or more and 600,000 or less. The mass 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 mass%, more preferably 0.2 to 98 mass%, even more preferably 0.3 to 97 mass%, still more preferably 0.3 to 50 mass%, particularly preferably 0.3 to 40 mass%, even more preferably 0.3 to 30 mass%, even more preferably 0.3 to 25 mass%, and particularly more preferably 0.3 to 20 mass%, based on the total amount of the active ingredients.

[0028] Furthermore, from the viewpoint of improving rust prevention properties 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 polyethyleneimine containing chlorine atoms. The reason why the effects of the present invention are more easily achieved when the content of polyethyleneimine containing chlorine atoms is lower is not clear, but it is thought that, for example, the chlorine atoms react with the cationic portion of polyethyleneimine, preventing the adsorption of droplets with increased anionicity. In the water-soluble heat-treated 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 properties by containing the rust inhibitor (C). The rust inhibitor (C) may be used alone or in combination of two or more. As the rust inhibitor (C), any one that has been widely used as an additive for heat treatment oils 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, carboxylic acids are preferred as the rust inhibitor (C) from the viewpoint of improving the effects of the present invention.

[0031] Examples of the carboxylic acid 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 monocarboxylic acid or a dicarboxylic or higher polycarboxylic acid, but is preferably a polycarboxylic acid, and more preferably a dicarboxylic acid. The number of carbon atoms in the carboxylic acid is preferably 4 or more from the viewpoint of improving rust prevention, and is preferably 20 or less from the viewpoint of improving water solubility. The number of carbon atoms in 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 that can be used as the rust inhibitor (C) include saturated aliphatic dicarboxylic acids such as various butanedioic acids (the term "various" refers to both linear and branched ones, 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 even more preferably 7 to 40 parts by mass, per 100 parts by mass of the active ingredient.

[0033] <Water-soluble polymer (D)> The water-soluble heat-treatment oil composition of this embodiment contains the water-soluble polymer (D), which makes it possible to adjust the cooling rate during heat treatment. 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) and propylene oxide (PO), and polyhydric alcohol alkylene oxide adducts, polyvinylpyrrolidones, and methylcelluloses. 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 linear polyalkylene glycol (D1) can be any polymer of alkylene glycol without any particular limitation, but is preferably at least one selected from the group consisting of linear polyalkylene glycols (D1-1) represented by the following general formula (d-1): R d1 O-(L d1 O) n -R d2 (d-1)

[0036] In the above general formula (d-1), R d1 and R d2 each 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 d2Examples of the alkyl group having 1 to 10 carbon atoms represented by 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. R d1 and R d2 The acyl group having 1 to 11 carbon atoms represented by the formula (I) includes an acyl group having an alkyl group having 1 to 10 carbon atoms and a carbonyl group. R d1 and R d2 Examples of the saturated alicyclic hydrocarbon group having 5 to 18 carbon atoms represented by include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecyl group. R d1 and R d2 Examples of the unsaturated alicyclic hydrocarbon group having 5 to 18 carbon atoms represented by include a cyclopentenyl group and a cyclohexenyl group. R d1 and R d2 Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by include aryl groups such as phenyl and naphthyl. 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 d1 O) 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. In addition, 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 multiple (L O) units, i.e., n ≥ 2, each (L d1 O) units may be the same or different. d1 When the O) units are different, they may be either random or block, but the random type is preferred from the viewpoint of ease of handling. Also, L 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). In addition, the monomer composition ratio of EO to PO (EO:PO) is preferably 43:57 to 94:6 by mass, 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; d1 O) 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; d1and R d2 and linear polyalkylene glycol derivatives, at least one of which 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, among the compounds represented by the general formula (d-1), those having hydrogen at both ends are referred to as polyalkylene glycols, and those having at least one end other than hydrogen are referred to as polyalkylene glycol derivatives. Furthermore, the term linear polyalkylene glycols (D1) is 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. Furthermore, 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 carbon atoms, and even more preferably 3 or 4 carbon atoms, from the viewpoint of solubility in water. 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 making it easier to suppress changes in the cooling rate when the water-soluble polymer (D) is repeatedly heat-treated, and improving the ability to adjust the cooling rate and ease of handling. 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. d1 A mixture of various structures having different types of O, composition 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, per 100 parts by mass of the active ingredient.

[0047] <Water> The water-soluble heat-treated oil composition of this embodiment may be a concentrate that does not contain water, 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; and the like can be used.

[0048] The water content is adjusted appropriately depending on the manner in which the water-soluble heat-treated oil composition is used. 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 "water content 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 to improve safety, and from the viewpoint of reducing the viscosity of the water-soluble heat-treatment oil composition to improve 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, still more preferably 85.0 mass% or more, particularly preferably 88.5 mass% or more. And, from the viewpoint of ensuring the amount of the active ingredient 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, still more preferably 99.5 mass% or less, particularly preferably 99.3 mass% or less. In addition, from the viewpoint of transportation efficiency, the water-soluble heat-treated oil composition of this embodiment is preferably a water-free concentrate. However, from the viewpoint of ensuring safety and stability, the concentrate may be diluted with the minimum amount of water necessary at the distribution stage and further diluted with water at the time of use. When the concentrate is diluted with water at the distribution stage (the water content of the second embodiment), the water content is preferably 30% by mass or more, more preferably 35% by mass or more, even more preferably 40% by mass or more, and even more preferably 45% by mass or more, based on 100% by mass of the total amount of the water-soluble heat-treated oil composition. Furthermore, from the viewpoint of ensuring the amount of the active ingredient in the water-soluble heat-treated oil composition, it is preferably 85% by mass or less, more preferably 83% by mass or less, even more preferably 81% by mass or less, and even more preferably 78% by 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 aspect described above, the content of component (A) is 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, and particularly preferably 0.50 mass% or more, based on 100 mass% of the total amount of the water-soluble heat-treated oil composition, from the viewpoint of making it easier to improve the effects of the present invention. Furthermore, from the viewpoint of further improving the effects of the present invention, the content of component (A) is preferably 8.0 mass% or less, more preferably 6.0 mass% or less, and even more preferably 4.0 mass% or less, based on the total amount of the water-soluble heat-treated oil composition.

[0050] <Polyethyleneimine (B) content> When the water content of the water-soluble heat-treated oil composition of this embodiment is the water content of the first aspect described above, the content of component (B) is preferably 0.0025 mass% or more, more preferably 0.005 mass% or more, and even more preferably 0.008 mass% or more, based on the total amount of the water-soluble heat-treated oil composition (100 mass%), in order to more easily improve the effects of the present invention. Furthermore, from the viewpoint of further improving the effects of the present invention, the content of component (B) is preferably 0.4 mass% or less, more preferably 0.3 mass% or less, and even more preferably 0.25 mass% or less, based on the total amount of the water-soluble heat-treated oil composition.

[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 content ratio of component (A) acting on one droplet and component (B) adsorbing multiple droplets is appropriate, and from the viewpoint of making it easier to improve the effects of the present invention by allowing both components to act in just the right amount, [(A) / (B)] is preferably 0.01 or more, more preferably 0.03 or more, even more preferably 1 or more, still more preferably 2 or more, particularly preferably 3 or more, and even more preferably 4 or more in mass ratio. Also, it is preferably 250 or less, more preferably 230 or less, even more preferably 210 or less, and still more preferably 205 or less. The upper and lower limits of these numerical ranges can be combined arbitrarily. Specifically, the range is preferably 0.01 to 250, more preferably 0.03 to 250, even more preferably 1 to 250, still more preferably 2 to 230, particularly preferably 3 to 210, and even more preferably 4 to 205.

[0052] <Rust inhibitor (C) content> When the water content of the water-soluble heat-treated oil composition of this embodiment is the water content of the first aspect described above, the content of component (C) is 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, based on 100 mass% of the total amount of the water-soluble heat-treated oil composition, in order to more easily improve the effects of the present invention. Furthermore, from the viewpoint of further improving the effects of the present invention, the content of component (C) is 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, based on the total amount of the water-soluble heat-treated oil composition.

[0053] <Ratio of hydroxyl-containing monoamine compound (A) to rust inhibitor (C) [(A) / (C)]> In the water-soluble heat-treated oil composition of this embodiment, from the viewpoint of making it easier to improve 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 still more preferably 2 or more. Also, it is preferably 100 or less, more preferably 70 or less, even more preferably 40 or less, and still more preferably 20 or less. The upper and lower limits of these numerical ranges can be combined arbitrarily. Specifically, the range 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] <Water-soluble polymer (D) content> When the water content of the water-soluble heat-treated oil composition of this embodiment is the water content of the first aspect described above, the content of component (D) is preferably 0.5 mass% or more, more preferably 1.0 mass% or more, and even more preferably 1.2 mass% or more, based on the total amount of the water-soluble heat-treated oil composition (100 mass%), in order to more easily improve the effects of the present invention. Furthermore, from the viewpoint of further improving the effects of the present invention, the content of component (D) is preferably 15.0 mass% or less, more preferably 13.5 mass% or less, and even more preferably 12.0 mass% or less, based on the total amount of the water-soluble heat-treated oil composition.

[0055] <Other ingredients> The water-soluble heat-treated 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 other components that may be blended as appropriate include corrosion inhibitors such as benzotriazole and tolyltriazole, copper deactivators, antioxidants, silicone-based antifoaming agents, colorants, 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 of producing a water-soluble heat-treated oil composition] The method for producing the water-soluble heat-treated oil composition of this embodiment is not particularly limited. For example, the method for producing a water-soluble heat-treatment oil composition of 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) and polyethyleneimine (B), The method 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 In the above, each —CH— in the substituted alkyl group 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, The method includes a 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 1is 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 In the above, each —CH— in the substituted alkyl group may be independently substituted with —O—. The order in which component (A), component (B), and water are mixed is not particularly limited, and 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 mixture may be mixed with water. Also, to a composition containing water and either component (A) or component (B) but not the other, either component (A) or component (B) that is not contained in the composition may be mixed. In addition, in the production method, component (A) and component (B) are blended with water, and component (C), component (D), and other components may also be blended as necessary. In this case, the order in which the components are blended, the blending method, etc. are not particularly limited. Since component (A), component (B), component (C), component (D), water, and other components are the same as those described above, and the preferred embodiments thereof are also the same, detailed explanations thereof will be omitted. Furthermore, the preferred blending amounts of component (A), component (B), component (C), component (D), water, and other components, and the preferred blending ratios between the respective components, are the same as the respective contents and content ratios in the water-soluble heat-treated oil composition described above, and detailed explanations thereof will be omitted.

[0059] [Uses of the water-soluble heat-treated 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 parts processed with metal processing oils containing strong emulsifiers, etc., and is more preferably used as a quenching oil. Note that, as the metal processing oil, preferred examples include emulsion-type water-soluble metal processing oil compositions and soluble-type water-soluble metal processing oil compositions.

[0060] [Oil separation method] As described above, the water-soluble heat-treated oil composition of this embodiment has excellent oil-separating properties because it contains a hydroxyl group-containing monoamine compound (A) having a specific structure and polyethyleneimine (B). However, even when the water-soluble heat-treated oil composition does not contain the hydroxyl group-containing monoamine compound (A) but contains polyethyleneimine (B), by contacting the water-soluble heat-treated oil composition with another composition containing the hydroxyl group-containing monoamine compound (A), the hydroxyl group-containing monoamine compound (A) in the composition is mixed into the water-soluble heat-treated oil composition, thereby exhibiting oil separation properties. That is, even when a water-soluble heat treatment oil composition that does not contain the hydroxyl group-containing monoamine compound (A) but contains polyethyleneimine (B) as an active ingredient is used for a metal component having oily components such as metal processing oil containing the hydroxyl group-containing monoamine compound (A) adhered thereto in a stage prior to a heat treatment process such as a cutting process, the oily components mixed in 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): 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 In the above, each —CH— in the substituted alkyl group may be independently substituted with —O—. The water-soluble heat-treated oil composition containing the above-mentioned polyethyleneimine (B) does not need to contain the hydroxyl group-containing monoamine compound (A), but from the viewpoint of promoting oil separation, it is preferable that it contains the hydroxyl group-containing monoamine compound (A). As the composition containing the hydroxyl group-containing monoamine compound (A), preferred examples 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 comprising 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 In the above, each —CH— in the substituted alkyl group may be independently substituted with —O—. [2] In the general formula (a-1), R 2 The water-soluble heat treatment oil composition according to [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-treated oil composition according to [1] or [2], wherein [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): 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, provided that R 21In the above, each —CH— in the substituted alkyl group may be independently substituted with —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 comprising water. [7] The water-soluble heat treatment oil composition according to any one of [1] to [6], further comprising a rust inhibitor (C). [8] The water-soluble heat treatment oil composition according to any one of [1] to [7], further comprising 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 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 [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 [1] to

[10] as a quenching oil or a 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), A method for producing a water-soluble heat-treated oil composition, 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 2In the above, each —CH— in the substituted alkyl group may be independently substituted with —O—.

[13] A method for producing a water-soluble heat treatment oil composition comprising a hydroxyl group-containing monoamine compound (A) represented by the following general formula (a-1), a polyethyleneimine (B), and water, A method for producing a water-soluble heat-treated oil composition, 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 In the above, each —CH— in the substituted alkyl group 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): 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 In the above, each —CH— in the substituted alkyl group may be independently substituted with —O—. [Example]

[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] The properties of the raw materials used in each Example and Comparative Example and the lubricating oil compositions of each Example and Comparative Example were measured according to the procedures shown below.

[0064] (1) Mass average molecular weight (Mw) and molecular weight distribution (Mw / Mn) of component (D) Measurements were performed 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 × 10 2 ~1.1×10 6 The measurements were performed using a 0.2 M sodium nitrate aqueous solution (g / mol) under the following conditions: solvent: 0.2 M sodium nitrate aqueous solution, flow rate: 1.0 mL / min, sample concentration: 0.3 w / v%, temperature: 40°C.

[0065] [Examples 1 to 31, Comparative Examples 1 to 22] The components below 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. The details of each component used in preparing the water-soluble heat-treated oil compositions shown in Tables 1 to 5 are explained below.

[0066] <Component (A)> Ingredient (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 Ingredient (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] <Ingredient (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 determined by a viscosity method, and the weight average molecular weight is a value determined by a GPC method using pullulan as a standard substance.

[0068] <Ingredient (C)> Rust inhibitor: Dodecanedioic acid

[0069] <Ingredient (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 separation 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 processing oil composition shown below. The mixture was mixed with a stirrer at 400 rpm for 5 minutes and then allowed to stand at room temperature for 1 day. After standing for one day, the state of oil separation from the water-soluble heat-treated oil composition was evaluated according to the following criteria, with ratings S and A being considered acceptable and ratings B and C being considered unacceptable. S: The water layer becomes lighter in color, the water-soluble metalworking oil composition separates into the upper layer, and oil separation is excellent. A: The color of the water layer becomes lighter, or the water-soluble metalworking oil composition separates or aggregates in the upper layer, and oil separation is fairly good. B: The color of the water layer is slightly lighter, and a small amount of the water-soluble metalworking oil composition separates or aggregates in the upper layer, and oil separation is somewhat poor. C: The water-soluble metalworking oil composition was emulsified, the test liquid was cloudy overall, and oil separation was poor.

[0073] <Water-soluble metal working oil composition> 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 Mirecourt AL (manufactured by Idemitsu Kosan Co., Ltd., emulsion type, containing 0.25 to 1% by 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. [Table 1] [Table 2] [Table 3] [Table 4] [Table 5]

[0075] <Evaluation results> From Tables 1 to 5, the following can be seen: The results shown in Examples 1 to 29 show that the water-soluble heat treatment oil composition containing the hydroxyl group-containing monoamine compound (A) and the polyethyleneimine (B) has excellent oil separation properties against any water-soluble metal processing oil. In contrast, the results shown in Comparative Examples 1 to 22 show that water-soluble heat-treated oil compositions that do not contain at least one of the hydroxyl group-containing monoamine compound (A) and the polyethyleneimine (B) have insufficient oil separation properties. Furthermore, the results shown in Examples 30 to 31 show that oil can be separated even when water-soluble metal processing oil composition 3 containing a hydroxyl group-containing monoamine compound (A) is 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): 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-.

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 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): 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-.

5. The 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. The 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 for using the water-soluble heat treatment oil composition according to any one of claims 1 to 10 as a quenching oil or a 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 polyethyleneimine (B), A method for producing a water-soluble heat-treatment oil composition, 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 - 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, A method for producing a water-soluble heat-treatment oil composition, 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): 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-.

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