JP2016160347A - Oil composition for lubrication and/or washing and/or cooling - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an oil composition having moderate viscosity stably, and having lubricating property, washing property and cooling property.SOLUTION: The oil composition for lubricant and/or washing and/or cooling is provided that contains following compound (A) and an oil solution (B). The compound (A): a compound represented by the following formula (1) (R-HNOC)-R-(CONH-R)(1) (in the formula, Ris a group removing 4 hydrogen atoms from benzene, benzophenone, biphenyl or naphthalene, Ris an aliphatic hydrocarbon group having 1 to 5 carbon atoms, Ris an aliphatic hydrocarbon group having 6 or more carbon atoms and n represents an integer of 1 to 3), and/or a compound represented by the following formula (2) R-(CONH-R)(2) (in the formula, Ris a group removing 4 hydrogen atoms from cyclohexane or butane and Ris an aliphatic hydrocarbon group having 1 or more carbon atoms).SELECTED DRAWING: None

Description

  The present invention relates to an oil composition used for the purpose of imparting lubricity, cleaning, and cooling when cutting a brittle material.

  When cutting brittle materials such as sapphire, glass, ceramics, silicon, and neodymium with a high-speed rotary cutting machine such as a fixed abrasive wire saw, machining fluid is usually used for the purpose of imparting lubricity and cleaning chips. . Patent Document 1 proposes to use a water-soluble composition containing glycols and a salt of a carboxylic acid and a basic compound as a processing liquid for a fixed abrasive wire saw (Patent Document 1). However, since the water-soluble composition has a low viscosity, it is difficult to hold on the wire during processing, and much of the processing liquid falls from the wire before reaching the processing portion and is supplied to the processing portion. It was a problem that the amount of machining fluid could not be secured, sufficient lubricity could not be obtained, the chip discharging action became insufficient, the chip adhered to the wire and the abrasive grains were clogged . In addition, the heat generated during processing cannot be cooled, and the durability of the abrasive grains fixed on the wire surface due to the processing heat is reduced and worn out, which causes another problem.

  As a method for solving the above problem, Patent Document 2 proposes a working fluid obtained by thickening glycols with a thickener containing an ethylene oxide / propylene oxide addition copolymer. However, it has been a problem that the working fluid thickened by the thickening agent becomes lower in viscosity over time.

JP 2003-82334 A JP 2012-126812 A

  Accordingly, an object of the present invention is to provide an oil composition that stably has an appropriate viscosity and has lubricity, detergency, and cooling properties.

As a result of intensive studies to solve the above problems, the present inventors have found that, when the following compound (A) is compatible with an oil agent, the oil agent can be thickened to an appropriate viscosity and the viscosity can be stably maintained. I found.
And since the oil agent thickened by the compound has a suitable viscosity stably and has lubricity, cleaning properties, and cooling properties, it gives lubricity when used as a processing liquid during cutting processing. It was found that the chips can be washed and the heat of processing can be cooled.
The present invention has been completed based on these findings.

That is, this invention provides the oil composition for lubrication and / or washing | cleaning and / or cooling containing the following compound (A) and oil agent (B).
Compound (A): Formula (1) below
_{^{(R 2 -HNOC) 4-n}} -R 1 - (CONH-R 3) n (1)
(In the formula, R ¹ is a group obtained by removing four hydrogen atoms from benzene, benzophenone, biphenyl, or naphthalene, R ² is an aliphatic hydrocarbon group having 1 to 5 carbon atoms, and R ³ is a group having 6 carbon atoms. These are the above aliphatic hydrocarbon groups, n represents an integer of 1 to 3)
And a compound represented by the following formula (2)
^{R 4 - (CONH-R 5} ) 4 (2)
(In the formula, R ⁴ is a group obtained by removing four hydrogen atoms from cyclohexane or butane, and four R ⁵ are the same or different and are aliphatic hydrocarbon groups having 1 or more carbon atoms)
At least one compound selected from the compounds represented by

  The present invention also provides the lubricating and / or cleaning and / or cooling oil composition comprising 0.5 to 10.0 parts by weight of the compound (A) with respect to 100 parts by weight of the oil (B). I will provide a.

  The present invention also provides the lubricating and / or cleaning and / or cooling oil composition used in the cutting process of brittle materials.

The oil composition of the present invention has an appropriate viscosity and can maintain the viscosity stably. In addition, when the oil composition of the present invention is used as a cutting fluid for brittle materials such as glass, ceramics, silicon, and neodymium, lubricity can be imparted, chips can be washed, and processing heat can be cooled. Thus, it is possible to suppress wear and drop of the cutting blade and abrasive grains due to processing heat, and it is possible to maintain excellent cutting performance over a long period of time.
Therefore, the oil composition of the present invention is a lubricating and / or cleaning and / or cooling oil composition (preferably, a lubricating and cleaning oil composition for use in cutting brittle materials). ) Can be suitably used.

[Compound (A)]
The compound (A) in the present invention has the following formula (1):
_{^{(R 2 -HNOC) 4-n}} -R 1 - (CONH-R 3) n (1)
(In the formula, R ¹ is a group obtained by removing four hydrogen atoms from benzene, benzophenone, biphenyl, or naphthalene, R ² is an aliphatic hydrocarbon group having 1 to 5 carbon atoms, and R ³ is a group having 6 carbon atoms. These are the above aliphatic hydrocarbon groups, n represents an integer of 1 to 3)
And a compound represented by the following formula (2)
^{R 4 - (CONH-R 5} ) 4 (2)
(In the formula, R ⁴ is a group obtained by removing four hydrogen atoms from cyclohexane or butane, and four R ⁵ are the same or different and are aliphatic hydrocarbon groups having 1 or more carbon atoms)
Is at least one compound selected from the compounds represented by:

  N represents an integer of 1 to 3, and is preferably 2.

Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms in R ² include linear or branched alkyl having 1 to 5 carbon atoms such as methyl, ethyl, butyl, isobutyl, t-butyl, and pentyl group. A group: a linear or branched alkenyl group having 2 to 5 carbon atoms such as methylene, methylmethylene, dimethylmethylene, ethylene, propylene or trimethylene group; a linear or branched alkenyl group having 2 to 5 carbon atoms such as ethynyl or propynyl group; A branched alkynyl group etc. can be mentioned.

R ² is preferably a linear or branched alkyl group having 1 to 5 carbon atoms such as a butyl group (particularly a linear alkyl group).

Examples of the aliphatic hydrocarbon group having 6 or more carbon atoms in R ³ include 6 to 20 carbon atoms (preferably 6 to 18 carbon atoms, particularly 6 to 18 carbon atoms, such as hexyl, octyl, 2-ethylhexyl, decyl, lauryl, myristyl, and stearyl groups. Preferably it is 8-18) C6-C20 (preferably 8-18, particularly preferably 12-26), such as a linear or branched alkyl group; 2-hexenyl, 7-octenyl, 9-decenyl, oleyl group, etc. 18) linear or branched alkenyl group; linear or branched having 6 to 20 carbon atoms (preferably 6 to 18, particularly preferably 12 to 18) such as hexynyl, octynyl, decynyl, pentadecynyl, octadecynyl group, etc. Examples thereof include a chain alkynyl group.

R ³ is a linear or branched alkenyl group having 6 to 20 carbon atoms (preferably 8 to 18 and particularly preferably 12 to 18) such as an oleyl group (particularly a linear alkenyl group). Is preferred.

Examples of the aliphatic hydrocarbon group having 1 or more carbon atoms in R ⁵ include the above-described examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms and the aliphatic hydrocarbon group having 6 or more carbon atoms.

As R ⁵ , among them, different groups (R ⁵¹ , R ⁵² ; R ⁵¹ , R ⁵² are different from each other and represent an aliphatic hydrocarbon group having 1 or more carbon atoms, and the same examples as R ⁵ described above are given. A linear or branched alkenyl group having 6 to 20 carbon atoms (preferably 8 to 18 and particularly preferably 12 to 18) such as an oleyl group (particularly a linear alkenyl group). And a linear or branched alkyl group having 1 to 20 carbon atoms (preferably 4 to 10, particularly preferably 4 to 8) such as a butyl group and a 2-ethylhexyl group.

Specific examples of the compound (A) include compounds represented by the following formulas. In the following formulae, R ² , R ³ , R ⁵¹ and R ⁵² are the same as described above. In addition, when several R < ² > exists in a formula, they are the same groups. The same applies to R ³ , R ⁵¹ and R ⁵² .

  The molecular weight of the compound (A) is, for example, 400 to 3000, preferably 800 to 2000, particularly preferably 800 to 1200, and most preferably 800 to 1000. When the molecular weight of the compound (A) exceeds the above range, the cooling property tends to decrease. On the other hand, when the molecular weight of the compound (A) is below the above range, the viscosity imparting effect tends to be reduced.

Compound (A) can be produced by the following method (a) or (b).
(A) A method in which a carboxylic acid is reacted with thionyl chloride to obtain a carboxylic acid chloride, and an amine is reacted with the obtained carboxylic acid chloride. (B) Amine (1) is reacted with a carboxylic acid anhydride corresponding to the carboxylic acid. To obtain an amic acid and further condense the amine (2) with carbodiimide

Examples of the carboxylic acid [R ^1- (COOH) ₄ : R ¹ is the same as described above] used when the compound represented by the formula (1) is produced by the production method (a) above include, for example, 1, 2 , 4,5-benzenetetracarboxylic acid, 3,3 ′, 4,4′-benzophenone tetracarboxylic acid, 1,1′-biphenyl-2,3,3 ′, 4′-tetracarboxylic acid, 1,4, Mention may be made of 5,8-naphthalenetetracarboxylic acid.

The carboxylic acid to be used when preparing compounds of formula (2) by the production method of ^{(a) [R 4 - (} COOH) 4: R 4 are the same as defined above] as, for example, 1,2 , 4,5-cyclohexanetetracarboxylic acid, 1,2,3,4-butanetetracarboxylic acid.

The amine used when the compound represented by the formula (1) is produced by the production method of (a) includes amine (R ² —NH ₂ ) and amine (R ³ —NH ₂ ) (R ² , R ³ is the same as above.

Examples of the amine (R ² —NH ₂ ) include an aliphatic hydrocarbon group having 1 to 5 carbon atoms such as butylamine (preferably a linear or branched alkyl group, alkenyl group, or alkynyl group). The amine etc. which have can be mentioned.

Examples of the amine (R ³ —NH ₂ ) include 6 or more carbon atoms (preferably 6 to 6 carbon atoms) such as hexylamine, octylamine, 2-ethylhexylamine, decylamine, laurylamine, myristylamine, stearylamine, and oleylamine. 20, particularly preferably an aliphatic hydrocarbon group having 10 to 20 carbon atoms, most preferably 15 to 20 carbon atoms (preferably a linear or branched alkyl group, alkenyl group, or alkynyl group). An amine etc. can be mentioned.

The amine used when producing the compound represented by formula (2) by the production method of (a) above includes amine (R ⁵ —NH ₂ ) (R ⁵ is the same as above). As the amine (R ⁵ —NH ₂ ), among them, two different amines (R ⁵¹ —NH ₂ ) (R ⁵¹ is the same as above) and amine (R ⁵² —NH ₂ ) (R ⁵² is the same as above) The same) is preferred.

Examples of the amine (R ⁵ —NH ₂ ) include 1 or more carbon atoms (preferably carbon atoms) such as butylamine, hexylamine, octylamine, 2-ethylhexylamine, decylamine, laurylamine, myristylamine, stearylamine, and oleylamine. And an amine having a 6-20) aliphatic hydrocarbon group (preferably a linear or branched alkyl group, alkenyl group, or alkynyl group). In the present invention, among them, a straight chain or branched alkenyl group having 6 to 20 carbon atoms (preferably 8 to 18, particularly preferably 12 to 18) such as an oleyl group (particularly a straight chain alkenyl group). An amine having a linear or branched alkyl group having 1 to 20 carbon atoms (preferably 4 to 10 and particularly preferably 4 to 8) such as a butyl group and a 2-ethylhexyl group. R ⁵¹ —NH ₂ ) and amine (R ⁵² —NH ₂ ) are preferably used in combination.

  In the production method (a), the reaction between the carboxylic acid chloride and the amine can be carried out, for example, by dropping the carboxylic acid chloride into the system charged with the amine.

  The reaction between the carboxylic acid chloride and the amine can be carried out in the presence or absence of a solvent. Examples of the solvent include saturated or unsaturated hydrocarbon solvents such as pentane, hexane, heptane, octane and petroleum ether; aromatic hydrocarbon solvents such as benzene, toluene and xylene; methylene chloride, chloroform, 1, 2 -Halogenated hydrocarbon solvents such as dichloroethane, chlorobenzene, bromobenzene; ether solvents such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, 1,2-dimethoxyethane, cyclopentyl methyl ether; acetonitrile, benzonitrile, etc. Nitrile solvents; sulfoxide solvents such as dimethyl sulfoxide; sulfolane solvents such as sulfolane; amide solvents such as dimethylformamide; high-boiling solvents such as silicone oil. These can be used individually by 1 type or in mixture of 2 or more types. In the present invention, it is preferable to use a halogenated hydrocarbon solvent in terms of excellent solubility of the reaction components (carboxylic acid chloride and amine).

  The amount of the solvent used is, for example, 50 to 300% by weight, preferably 100 to 250% by weight, based on the total amount of carboxylic acid chloride and amine. When the usage-amount of a solvent exceeds the said range, the density | concentration of a reaction component will become low and there exists a tendency for reaction rate to fall.

  The reaction (= dropping) of carboxylic acid chloride and amine is usually carried out under normal pressure. Further, the atmosphere of the above reaction (= drip) is not particularly limited as long as the reaction is not inhibited, and may be any of an air atmosphere, a nitrogen atmosphere, an argon atmosphere, and the like. Reaction temperature (= temperature at the time of dripping) is 30-60 degreeC, for example. The reaction time (= dropping time) is, for example, 0.5 to 20 hours. After completion of the reaction (= dropping), an aging step may be provided. When providing an aging step, the aging temperature is, for example, 30 to 60 ° C., and the aging time is, for example, 1 to 5 hours. The reaction can be carried out by any method such as batch, semi-batch and continuous methods.

  After completion of the reaction, the obtained reaction product can be separated and purified by separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, etc., or a separation means combining these.

  In the production method of (b), for example, an amic acid is formed by charging and aging the carboxylic acid anhydride, the amine (1) and the following solvent into the system, and then further aminating the amine (2) and the condensing agent ( The compound (A) can be produced by charging and aging carbodiimide or a salt thereof.

  Examples of the carboxylic acid anhydride used when producing the compound represented by the formula (1) by the production method of (b) above include 1,2,4,5-benzenetetracarboxylic acid-1,2: 4,5-dianhydride, 3,3 ′, 4,4′-benzophenone tetracarboxylic dianhydride, 1,1′-biphenyl-2,3,3 ′, 4′-tetracarboxylic acid-2,3 : 3 ′, 4′-dianhydride, naphthalene-1,4,5,8-tetracarboxylic acid-1,8: 4,5-dianhydride and the like.

  Examples of the carboxylic acid anhydride used when producing the compound represented by the formula (2) by the production method of (b) above include 1,2,4,5-cyclohexanetetracarboxylic acid-1,2: 4,5-dianhydride, meso-butane-1,2,3,4-tetracarboxylic dianhydride, and the like.

The amines (1) and (2) used when the compound represented by the formula (1) is produced by the production method (b) are represented by the formula (1) by the production method (a). As in the case of producing the compound, amine (R ² —NH ₂ ) and amine (R ³ —NH ₂ ) can be used.

The amines (1) and (2) used when producing the compound represented by the formula (2) by the production method (b) are represented by the formula (2) by the production method (a). In the same manner as in the production of the above compound, amine (R ⁵ —NH ₂ ) [preferably amine (R ⁵¹ —NH ₂ ) and amine (R ⁵² —NH ₂ )] can be used.

  The usage-amount of amine (1) is 2-4 mol with respect to 1 mol of carboxylic anhydrides, Preferably it is 2-3 mol. Moreover, as the usage-amount of amine (2), it is 2-4 mol with respect to 1 mol of carboxylic anhydrides, Preferably it is 2-3 mol.

The carbodiimide is represented by the following formula.
RN = C = NR ′
In the above formula, as R and R ′, for example, a linear or branched alkyl group having 3 to 8 carbon atoms which may have a heteroatom-containing substituent, or a 3- to 8-membered cyclo group. An alkyl group etc. can be mentioned. R and R ′ may be the same or different. R and R ′ may be bonded to each other to form a ring together with the —N═C═N— group.

  Examples of the linear or branched alkyl group having 3 to 8 carbon atoms include n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, s- Examples include pentyl, t-pentyl, n-hexyl, isohexyl, s-hexyl, t-hexyl group and the like.

  Examples of the 3- to 8-membered cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl groups.

Examples of the heteroatom-containing substituent include nitrogen atom-containing substituents such as di (C _1-3 ) alkylamino groups such as amino groups and dimethylamino groups.

  Examples of the carbodiimide include diisopropylcarbodiimide, dicyclohexylcarbodiimide, N- (3-dimethylaminopropyl) -N′-ethylcarbodiimide and the like. Examples of the carbodiimide salt include hydrochloride (specifically, N- (3-dimethylaminopropyl) -N′-ethylcarbodiimide hydrochloride) and the like.

  The amount of carbodiimide or a salt thereof used is, for example, 2 to 6 mol, preferably 2 to 4 mol, per 1 mol of carboxylic anhydride.

  As the solvent, for example, it is preferable to use a proton-accepting solvent excellent in solubility of amic acid such as pyridine, triethylamine, tributylamine and the like. These can be used individually by 1 type or in mixture of 2 or more types.

  As the usage-amount of the said solvent, it is 50 to 300 weight% with respect to the total amount of amic acid, Preferably it is 100 to 250 weight%. When the usage-amount of a solvent exceeds the said range, the density | concentration of a reaction component will become low and there exists a tendency for reaction rate to fall.

  The above reaction is usually performed under normal pressure. Further, the atmosphere of the reaction is not particularly limited as long as the reaction is not inhibited, and may be any of an air atmosphere, a nitrogen atmosphere, an argon atmosphere, and the like. The aging temperature (reaction temperature) is, for example, 30 to 70 ° C. The aging time of the carboxylic acid anhydride and the amine is, for example, 0.5 to 5 hours, and the aging time of the amic acid and the amine is, for example, 0.5 to 20 hours. The reaction can be carried out by any method such as batch, semi-batch and continuous methods.

  After completion of the reaction, the obtained reaction product can be separated and purified by separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, etc., or a separation means combining these.

Compound (A) self-associates by hydrogen bonding at the amide bond site to form a fiber-like self-assembly, and further, side chains (R ² and R ^{3 in} the compound represented by Formula (1), Formula (2) In the compound represented by (), R ⁵ ) has an affinity for the oil agent (B), and therefore, when mixed with the oil agent (B), the effect of thickening the oil agent (B) is exhibited.

[Oil agent (B)]
As the oil agent in the present invention, it can be used without particular limitation. For example, hydrocarbon oils (for example, hexane, cyclohexane, isododecane, benzene, toluene, polyalphaolefin, liquid paraffin, normal paraffin, etc.), ethers (for example, , Tetrahydrofuran, etc.), halogenated hydrocarbons (eg, carbon tetrachloride, chlorobenzene, etc.), petroleum components (eg, kerosene, gasoline, light oil, heavy oil, etc.), animal and vegetable oils (eg, sunflower oil, olive oil, soybean oil, corn oil) , Castor oil, beef tallow, jojoba oil, squalane, etc.), silicones (eg, dimethylpolysiloxane, methylphenylpolysiloxane, etc.), esters (eg, octyldodecyl oleate, cetyl ethylhexanoate, glyceryl triisooctanoate, Neopentyl grits Over distearate isooctanoate sulfonate, etc.), carboxylic acid, and pyridine. These can be used alone or in combination of two or more.

[Oil composition]
The oil composition of the present invention comprises the above compound (A) and an oil agent (B). As for a compound (A) and an oil agent (B), all can be used individually by 1 type or in combination of 2 or more types.

  The content of the compound (A) in the oil composition of the present invention (the total amount when containing two or more) is, for example, 0.5 to 10.0 parts by weight, preferably 100 parts by weight of the oil (B). Is 0.7 to 4.0 parts by weight, particularly preferably 0.8 to 2.0 parts by weight. By blending the compound (A) in the above range, an appropriate viscosity can be imparted to the oil agent (B) as a cutting liquid.

  The content of the compound (A) in the total amount (100% by weight) of the oil composition of the present invention (the total amount when two or more types are contained) is, for example, 0.5 to 10.0% by weight, preferably 0.7. It is -4.0 weight%, Most preferably, it is 0.8-2.0 weight%.

  The content of the oil agent (B) in the total amount (100% by weight) of the oil composition of the present invention (the total amount when containing two or more types) is, for example, 90.0 to 99.5% by weight, preferably 96.0. ˜99.3% by weight.

  The oil composition of the present invention may contain other thickeners in addition to the compound (A), but the ratio of the compound (A) to the total thickeners contained in the oil composition is, for example, 30. % By weight or more, preferably 50% by weight or more, particularly preferably 70% by weight or more, and most preferably 85% or more. When the ratio of the other thickener exceeds the above range, the effect of the present application tends to be difficult to obtain. In the present invention, the “thickening agent” is a compound that dissolves in an oil agent to generate viscosity, a thickening agent that imparts viscosity to the oil agent (B), a gelling agent that gels the oil agent (B), and A stabilizer that increases the viscosity is included for the purpose of uniformly stabilizing the composition containing the oil agent (B).

  The oil composition of the present invention may contain one or more other components in addition to the thickener and the oil agent (B) containing the compound (A). Examples of other components include abrasive grains.

  The oil composition of this invention can be manufactured through the process of making the said compound (A) and an oil agent (B) compatible. More specifically, it can be produced by mixing the whole amount of the compound (A) and the oil agent (B), heating them, making them compatible, and then cooling them. Alternatively, the compound (A) may be mixed with a part of the oil agent (B), heated and dissolved, cooled, and then mixed with the remaining oil agent (B). .

The combination of the compound (A) and the oil agent (B) is not particularly limited as long as the compound (A) and the oil agent (B) are compatible, but from the viewpoint of the minimum gelation concentration, the polarity of the oil agent (B) is When the [SP value is less than 10 (cal / cm ³ ) ^0.5 ], the compound represented by the formula (1) is represented by R ³ , and the compound represented by the formula (2) is represented by four R ⁵ It is preferable to have an aliphatic hydrocarbon group having 8 to 20 carbon atoms (preferably 10 to 20 carbon atoms, particularly preferably 15 to 20 carbon atoms, most preferably 18 to 20 carbon atoms). Moreover, when the polarity of the solvent of the oil agent (B) is high [SP value is 10 (cal / cm ³ ) ^0.5 or more], the compound (A) is R ³ as long as it is a compound represented by the formula (1). The compound represented by the formula (2) preferably has an aliphatic hydrocarbon group having 6 to 7 carbon atoms as at least one of four R ⁵ . In addition, SP value in this specification is a value in 25 degreeC calculated by the Fedors method.

  The temperature at the time of compatibility is appropriately selected depending on the types of the compound (A) and the oil agent (B), and is not particularly limited as long as the compound (A) and the oil agent (B) are compatible with each other. It is preferable not to exceed ℃, and when the boiling point of the oil agent (B) is 100 ℃ or less, the boiling point is preferred.

  The cooling after the compatibilization may be performed at room temperature (for example, 1 to 30 ° C.) or less, and may be gradually cooled at room temperature, or may be rapidly cooled by ice cooling or the like.

The kinematic viscosity of the oil composition of the present invention [at 40 ℃; JIS K 2283 (2000 years) Compliance is for example 1 to 200 mm ² / s (preferably 15~100mm ² / s, particularly preferably 20 to 50 mm ² / s, most preferably 25 to 50 mm ² / s, and particularly preferably 30 to 50 mm ² / s). If the kinematic viscosity exceeds the above range, the cooling effect tends to be difficult to obtain. When the kinematic viscosity is below the above range, it tends to be difficult to impart sufficient lubricity.

  The 5% weight reduction temperature of the oil composition of the present invention is, for example, 100 to 400 ° C, preferably 100 to 350 ° C, and particularly preferably 150 to 300 ° C. When the 5% weight loss temperature is in the above range, after use, the chips can be easily separated and removed by subjecting the oil composition containing the chips to distillation, and the oil composition can be reused as a processing liquid. can do. The 5% weight loss temperature can be determined by differential thermal-thermogravimetric simultaneous measurement (TG-DTA) or the like.

  In addition, since the oil composition of the present invention uses the low molecular weight compound (A) as a thickener, the molecules can freely move in the network of the thickener. Therefore, excellent cooling performance can be exhibited while maintaining the viscosity according to the application.

  Furthermore, the oil composition of the present invention has a residual ash content of 1% by weight or less. Therefore, the frequency | count of washing | cleaning performed in order to remove residual ash can be reduced.

  Since the oil composition of the present invention has the above-mentioned characteristics, it is possible to use a cutting machine (for example, fixed abrasive wire saw, loose abrasive wire saw, disk cutter, lathe, drill, etc.), for example, sapphire, glass, ceramics, silicon, Cutting fluid for cutting of brittle materials such as neodymium (oil composition for cutting), processing fluid for drilling shale oil (oil composition for drilling), CMP (Chemical Mechanical Polishing) It is useful as a raw material for polishing materials for polishing.

  EXAMPLES Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited by these Examples.

Synthesis Example 1 [Synthesis of thickener (1) (1,2,4,5-benzenetetracarboxylic acid di (butylamide) di (oleylamide)]
20 mL of pyridine, 1,2,4,5-benzenetetracarboxylic acid-1,2: 4,5-dianhydride in a 100 mL four-necked separable flask equipped with a Dimroth condenser, nitrogen inlet, dropping funnel, thermocouple 3.0 g (0.014 mol) and 7.4 g (0.028 mol) of oleylamine were charged. The system temperature was set to 50 ° C. and aged for 3 hours.
Thereafter, 2.1 g (0.028 mol) of butylamine and 7.0 g (0.056 mol) of diisopropylcarbodiimide were added, followed by further aging for 8 hours.
Thereafter, the low boiling content of the obtained crude liquid was removed by an evaporator and washed with methanol to obtain a pale yellow wet powder. Further, the obtained wet powder was recrystallized with CHCl ₃ / CH ₃ OH (70/30 (v / v)) to obtain 1,2,4,5-benzenetetracarboxylic acid di (butylamide) di (oleylamide). (Molecular weight: 863) [1,2,4,5-benzenetetracarboxylic acid-1,4-di (butylamide) -2,5-di (oleylamide) and 1,2,4,5-benzenetetracarboxylic acid -1,5-di (butylamide) -2,4-di (oleylamide) mixture] was obtained (yield: 61%).

Synthesis Example 2 [Synthesis of Thickener (2) (1,2,4,5-cyclohexanetetracarboxylic acid di (butylamide) di (oleylamide))]
20 mL of pyridine, 1,2,4,5-cyclohexanecarboxylic acid-1,2: 4,5-dianhydride 4 in a 100 mL four-necked separable flask equipped with a Dimroth condenser, nitrogen inlet, dropping funnel, thermocouple 0.5 g (0.02 mol) and oleylamine 10.7 g (0.04 mol) were charged. The system temperature was set to 50 ° C. and aged for 3 hours.
Thereafter, 2.9 g (0.02 mol) of butylamine and 5.5 g (0.044 mol) of diisopropylcarbodiimide were charged, followed by further aging for 8 hours.
Thereafter, the low boiling content of the obtained crude liquid was removed by an evaporator and washed with methanol to obtain a pale yellow wet powder. Further, the obtained wet powder was recrystallized with CHCl ₃ / CH ₃ OH (70/30 (v / v)) to obtain 1,2,4,5-cyclohexanetetracarboxylic acid di (butylamide) di (oleylamide). (Molecular weight: 869) [1,2,4,5-cyclohexanetetracarboxylic acid-1,4-di (butylamide) -2,5-di (oleylamide) and 1,2,4,5-cyclohexanetetracarboxylic acid -1,5-di (butylamide) -2,4-di (oleylamide) mixture] was obtained (yield: 67%).

Synthesis Example 3 [Synthesis of thickener (3) (1,2,3,4-butanetetracarboxylic acid di (butylamide) di (oleylamide))]
20 mL of pyridine, 1,2,3,4-butanetetracarboxylic acid-1,2: 3,4-dianhydride in a 100 mL four-neck separable flask equipped with a Dimroth condenser, nitrogen inlet, dropping funnel, and thermocouple 4.2 g (0.021 mol) of the product and 11.3 g (0.042 mol) of oleylamine were charged. The system temperature was set to 50 ° C. and aged for 3 hours.
Thereafter, 3.1 g (0.042 mol) of butylamine and 5.8 g (0.048 mol) of diisopropylcarbodiimide were added, followed by further aging for 8 hours.
Thereafter, the low boiling content of the obtained crude liquid was removed by an evaporator and washed with methanol to obtain a pale yellow wet powder. Further, the obtained wet powder was recrystallized with CHCl ₃ / CH ₃ OH (70/30 (v / v)) to obtain 1,2,3,4-butanetetracarboxylic acid di (butylamide) di (oleylamide). (Molecular weight: 843) [1,2,3,4-butanetetracarboxylic acid-1,4-di (butylamide) -2,3-di (oleylamide) and 1,2,3,4-butanetetracarboxylic acid -1,3-di (butylamide) -2,4-di (oleylamide)] was obtained 14.7 g (yield: 83%).

Synthesis Example 4 [Synthesis of thickener (4) (3,3 ′, 4,4′-benzophenone tetracarboxylic acid di (butylamide) di (oleylamide)]
Into a 100 mL 4-neck separable flask equipped with a Dimroth condenser, nitrogen inlet and dropping funnel, thermocouple, 20 g of pyridine, 3.0 g (0.012 mol) of 3,3 ′, 4,4′-benzophenone tetracarboxylic dianhydride ), 6.47 g (0.024 mol) of oleylamine was charged. The system temperature was set to 50 ° C. and aged for 3 hours.
Thereafter, 1.8 g (0.024 mol) of butylamine and 6.1 g (0.048 mol) of diisopropylcarbodiimide were added, followed by further aging for 8 hours.
Thereafter, the low boiling content of the obtained crude liquid was removed by an evaporator and washed with methanol to obtain a pale yellow wet powder. Further, the obtained wet powder was recrystallized with CHCl ₃ / CH ₃ OH (70/30 (v / v)) to obtain 3,3 ′, 4,4′-benzophenonetetracarboxylic acid di (butylamide) di (oleyl). 4.8 g of amide) (molecular weight: 967) was obtained (yield: 41%).

Synthesis Example 5 [Synthesis of thickener (5) (1,2,4,5-cyclohexanetetracarboxylic acid di (2-ethylhexylamide) di (oleylamide))]
1,2,4,5-Cyclohexanetetracarboxylic acid di (2-ethylhexylamide) di, except that 5.2 g (0.04 mol) of 2-ethylhexylamine was used instead of butylamine (Oleylamide) (Molecular weight: 982) [1,2,4,5-Cyclohexanetetracarboxylic acid-1,4-di (2-ethylhexylamide) -2,5-di (oleylamide) and 1,2,4 , 5-cyclohexanetetracarboxylic acid-1,5-di (2-ethylhexylamide) -2,4-di (oleylamide)] was obtained (yield: 61%).

Synthesis Example 6 [Synthesis of thickener (6) (1,2,3,4-butanetetracarboxylic acid di (2-ethylhexylamide) di (oleylamide))]
1,2,3,4-Butanetetracarboxylic acid di (2-ethylhexylamide) di, except that 5.4 g (0.042 mol) of 2-ethylhexylamine was used instead of butylamine (Oleylamide) (molecular weight: 956) [1,2,3,4-butanetetracarboxylic acid-1,4-di (2-ethylhexylamide) -2,3-di (oleylamide) and 1,2,3 , 4-Butanetetracarboxylic acid-1,3-di (2-ethylhexylamide) -2,4-di (oleylamide)] was obtained (yield: 83%).

Synthesis Example 7 [Synthesis of thickener (7) (1,2,4,5-benzenetetracarboxylic acid di (2-ethylhexylamide) di (oleylamide))]
The same procedure as in Synthesis Example 1 was conducted except that 3.6 g (0.028 mol) of 2-ethylhexylamine was used instead of butylamine, and 1,2,4,5-benzenetetracarboxylic acid di (2-ethylhexylamide) di (Oleylamide) [1,2,4,5-benzenetetracarboxylic acid-1,4-di (2-ethylhexylamide) -2,5-di (oleylamide) and 1,2,4,5-benzenetetra 5.9 g of carboxylic acid-1,5-di (2-ethylhexylamide) -2,4-di (oleylamide) mixture] (yield: 51%).

Synthesis Example 8 [Synthesis of thickener (8) (1,2,4,5-benzenetetracarboxylic acid di (hexylamide) di (oleylamide))]
1,2,4,5-benzenetetracarboxylic acid di (hexylamide) di (oleylamide), except that 2.8 g (0.028 mol) of hexylamine was used instead of butylamine [1,2,4,5-benzenetetracarboxylic acid-1,4-di (hexylamide) -2,5-di (oleylamide) and 1,2,4,5-benzenetetracarboxylic acid-1,5 -Di (hexylamide) -2,4-di (oleylamide) mixture] was obtained (yield: 64%).

Examples 1-6, Comparative Examples 1-5
The mixture was mixed according to the formulation (unit: parts by weight) shown in the following table, heated and stirred at 100 ° C. to dissolve the oil agent and the thickener, and then cooled to 25 ° C. to obtain an oil composition.
The kinematic viscosity of the obtained oil composition was measured at 40 ° C. using an Ubbelohde kinematic viscometer in accordance with JIS K 2283 (2000).
Moreover, the cooling property, detergency, and drying property of the obtained oil composition were evaluated by the following methods.

<Coolability>
Test conditions Test equipment: Quenching tester (trade name “IVF Smart Quench”, manufactured by Parker Heat Treatment Industry Co., Ltd.)
Test time: 20 seconds Test temperature: 200 ° C
Oil composition: 1000 mL
Test Method A thermocouple-containing probe (trade name “K-type thermocouple probe AD-1217”, manufactured by A & D) was heated to 200 ° C. in an electric furnace. 1000 mL of the oil composition was put in a beaker, the heated probe was put in the oil composition and allowed to stand for 20 seconds, the maximum cooling efficiency was measured, and evaluated according to the following criteria.
Evaluation criteria Maximum cooling efficiency ○: 23 ° C / sec or more ×: Less than 23 ° C / sec

<Detergency>
Test conditions Stirrer: Homogenizer Test temperature: 25 ° C
Oil composition: 100 mL
Chip addition amount: Silicon chip 10g
Washing water volume: 300 mL
Test piece: Silicon wafer (φ3 inch x thickness 0.8mm)
Test Method The oil composition and silicon chips were transferred to a homogenizer and stirred at a rotational speed of 10,000 rpm for 2 minutes. After the completion of stirring, the oil composition containing silicon chips was impregnated to 50 mm below the silicon wafer for 15 seconds, and left standing in a vertical state for 1 hour. After standing, it was washed by showering using water (water) and dried, and the contamination state of the silicon wafer surface was evaluated according to the following criteria.
Evaluation criteria ○: Dirt adhering to the surface of the silicon wafer is 5% by weight or less X: Dirt adhering to the surface of the silicon wafer exceeds 5% by weight

<Drying>
Test Method 100 mL of the oil composition was placed in a beaker and heat-treated at 350 ° C. for 1 hour. After the heat treatment, the remaining ash weight was measured and evaluated according to the following criteria.
Evaluation criteria ○: Residual ash content after drying is 1% by weight or less ×: Residual ash content after drying exceeds 1% by weight

※ノルマルパラフィン：ＳＰ値８．２（ｃａｌ／ｃｍ³）^0.5、沸点１９６〜２３０℃
芳香族ウレア：ビックケミー・ジャパン社製、商品名「ＢＹＫ４１０」
ステアリン酸イヌリン：千葉製粉（株）製、商品名「レオパールＩＳＬ２」 The above results are summarized in the following table.

* Normal paraffin: SP value 8.2 (cal / cm ³ ) ^0.5 , boiling point 196 to 230 ° C.
Aromatic urea: manufactured by Big Chemie Japan, trade name “BYK410”
Inulin stearate: manufactured by Chiba Flour Milling Co., Ltd., trade name “Leopard ISL2”

Claims (3)

An oil composition for lubricating and / or cleaning and / or cooling comprising the following compound (A) and oil (B).
Compound (A): Formula (1) below
_{^{(R 2 -HNOC) 4-n}} -R 1 - (CONH-R 3) n (1)
(In the formula, R ¹ is a group obtained by removing four hydrogen atoms from benzene, benzophenone, biphenyl, or naphthalene, R ² is an aliphatic hydrocarbon group having 1 to 5 carbon atoms, and R ³ is a group having 6 carbon atoms. These are the above aliphatic hydrocarbon groups, n represents an integer of 1 to 3)
And a compound represented by the following formula (2)
^{R 4 - (CONH-R 5} ) 4 (2)
(In the formula, R ⁴ is a group obtained by removing four hydrogen atoms from cyclohexane or butane, and four R ⁵ are the same or different and are aliphatic hydrocarbon groups having 1 or more carbon atoms)
At least one compound selected from the compounds represented by   The oil composition for lubrication and / or cleaning and / or cooling according to claim 1, wherein the compound (A) is contained in an amount of 0.5 to 10.0 parts by weight with respect to 100 parts by weight of the oil (B).   The oil composition for lubrication and / or cleaning and / or cooling according to claim 1 or 2, which is used for cutting a brittle material.