JP6431047B2 - Oil composition for lubrication and / or cleaning and / or cooling - Google Patents

Description

  The present invention relates to an oil composition used for the purpose of imparting lubricity, cleaning, and cooling during cutting. This application claims the priority of Japanese Patent Application No. 2014-071870 for which it applied to Japan on March 31, 2014, and uses the content here.

  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 (propylene glycol, polyethylene glycol, etc.) and a salt of a carboxylic acid and a basic compound as a working fluid for a fixed abrasive wire saw ( Patent Document 1). However, since the water-soluble composition has a low viscosity, it is difficult to hold it on the wire during processing, and a lot of processing liquid falls from the wire before reaching the processing part and is supplied to the processing part. The amount of liquid cannot be secured sufficiently, it becomes difficult to give sufficient lubricity, the chip discharging action becomes insufficient, the chip adheres to the wire and the abrasive grains are clogged Was a problem. 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, resulting in wear and dropping.

  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 difficult to stably maintain the viscosity of the working fluid thickened by the thickener, and it has been a problem that the viscosity decreases with 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-mentioned problems, the inventors of the present invention can increase the viscosity of an oil agent to an arbitrary viscosity and stably maintain the viscosity, An oil composition obtained by thickening an oil agent with the above compound has an appropriate viscosity stably, and has lubricity (= reducing friction, suppressing generation of frictional heat and cutting blades and abrasive grains). It has been found that, when it is used as a processing liquid during cutting processing, it can provide lubricity, clean chips, and cool processing heat. The present invention has been completed based on these findings.

That is, the present invention provides 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 the structural formula of benzene, R ² and R ³ are different from each other, and are aliphatic hydrocarbon groups having 6 or more carbon atoms. N is 1 Represents an integer of ~ 3)
An oil composition for lubricating and / or cleaning and / or cooling comprising the compound (A) represented by the formula (A) and the oil agent (B) is provided.

  The present invention also provides the lubricating and / or cleaning and / or cooling oil composition comprising 0.5 to 10% by weight of the total amount of the oil composition (A) represented by the formula (1). I will provide a.

The present invention also provides 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 the structural formula of benzene, R ² and R ³ are different from each other, and are aliphatic hydrocarbon groups having 6 or more carbon atoms. N is 1 Represents an integer of ~ 3)
The oil composition for cutting process containing the compound (A) represented by these, and an oil agent (B) is provided.

That is, the present invention relates to the following.
[1] 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 the structural formula of benzene, R ² and R ³ are different from each other, and are aliphatic hydrocarbon groups having 6 or more carbon atoms. N is 1 Represents an integer of ~ 3)
An oil composition for lubricating and / or cleaning and / or cooling comprising the compound (A) represented by formula (A) and the oil agent (B).
[2] The lubricating and / or cleaning and / or cooling oil composition according to [1], containing 0.5 to 10% by weight of the total amount of the oil composition (A) represented by the formula (1) object.
[3] The lubricating and / or lubricating agent according to [1] or [2], containing 0.5 to 10 parts by weight of the compound (A) represented by the formula (1) with respect to 100 parts by weight of the oil (B) Or an oil composition for washing and / or cooling.
[4] The lubrication according to any one of [1] to [3], wherein the compound (A) is at least one selected from the compounds represented by formulas (1-1) to (1-4) And / or cleaning and / or cooling oil compositions.
[5] The compound (A) is represented by the formula (1), R ² in the formula (1) is a branched alkyl group having 6 to 10 carbon atoms, and R ³ is a straight chain having 16 to 20 carbon atoms. The oil composition for lubrication and / or cleaning and / or cooling according to any one of [1] to [4], which is a compound that is a chain alkyl group or a linear alkenyl group.
[6] The lubricating and / or cleaning and / or cooling oil composition according to any one of [1] to [5], wherein the molecular weight of the compound (A) is 800 to 1100.
[7] The oil agent (B) is at least one compound selected from hydrocarbon oils, ethers, halogenated hydrocarbons, petroleum components, animal and vegetable oils, silicones, esters, aromatic carboxylic acids, and pyridines [1] ] The oil composition for lubrication and / or washing | cleaning and / or cooling as described in any one of [6].
[8] Lubricating and / or cleaning according to any one of [1] to [7], wherein the kinematic viscosity [at 40 ° C .; JIS K 2283 (2000) compliant] is 15 to 50 mm ² / s. And / or oil composition for cooling.
[9] The lubricating and / or cleaning and / or cooling oil composition according to any one of [1] to [8], wherein the 5% weight loss temperature is 150 to 300 ° C.
[10] The lubricating and / or cleaning and / or cooling oil composition according to any one of [1] to [9], wherein the residual ash content is 1% by weight or less.
[11] The lubricating and / or cleaning and / or cooling oil composition according to any one of [1] to [10], which is a cutting processing oil composition.
[12] The lubricating and / or cleaning and / or cooling oil composition according to any one of [1] to [10], which is a drilling oil composition.
[13] The lubricating and / or cleaning and / or cooling oil composition according to any one of [1] to [10], which is an abrasive for CMP.

  Since the oil composition of the present invention uses the compound represented by the above formula (1) as a thickener for an oil agent, it can impart a viscosity suitable for the application to the oil agent, and can further stabilize the viscosity. Can be maintained. In addition, it has lubricity, cleanability, and cooling properties. Therefore, when the oil composition of the present invention is used as a working fluid at the time of cutting, lubricity can be imparted, chips can be washed, and processing heat can be cooled. Therefore, it can be suitably used when processing brittle materials such as sapphire, glass, ceramics, silicon, and neodymium. Moreover, when the oil composition of this invention is used, abrasion of a cutting blade and an abrasive grain can be suppressed and the outstanding cutting property can be maintained over a long period of time.

[Compound (A)]
The compound (A) of the present invention is represented by the following formula (1).
_{^{(R 2 -HNOC) 4-n}} -R 1 - (CONH-R 3) n (1)

In the formula (1), R ¹ is a group obtained by removing four hydrogen atoms from the structural formula of benzene, and R ² and R ³ are different from each other and are aliphatic hydrocarbon groups having 6 or more carbon atoms. n shows the integer of 1-3.

Examples of the compound (A) of the present invention include compounds represented by the following formulas (1-1) to (1-4). In the following formula, R ² and R ³ are the same as described above.

  As the compound (A) of the present invention, among them, the compound represented by the above formula (1-1) and / or (1-2) is preferable from the viewpoint of excellent solubility of the oil agent (B). Moreover, when the oil agent (B) is transparent, the compound is preferable in that the viscosity can be increased while maintaining the transparency.

In the above formula, R ² and R ³ are different from each other and represent an aliphatic hydrocarbon group having 6 or more carbon atoms, such as hexyl, octyl, 2-ethylhexyl, decyl, lauryl, myristyl, stearyl, nonadecyl group, etc. A linear or branched alkyl group of about 6 to 20 (preferably 6 to 18, particularly preferably 8 to 18); 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 7-octenyl, A linear or branched alkenyl group having about 6 to 20 carbon atoms (preferably 6 to 18, particularly preferably 12 to 18) such as 9-decenyl, 11-dodecenyl, oleyl group; hexynyl, octynyl, decynyl, pentadecynyl A linear or branched alkyl having about 6 to 20 carbon atoms (preferably 6 to 18, particularly preferably 12 to 18) such as an octadecynyl group. It can be exemplified Le group.

As the compound (A) of the present invention, in particular, R ² has about 6 to 20 carbon atoms (the upper limit of the carbon number is preferably 18, particularly preferably 12, and most preferably 10. The lower limit of the carbon number is Preferably, it is a branched alkyl group of 8 and R ³ is about 6 to 20 carbon atoms (the upper limit of the carbon number is preferably 18. The lower limit of the carbon number is preferably 10, particularly preferably. 12 and most preferably 16) is a straight-chain alkyl group or a straight-chain alkenyl group compound that is particularly excellent in the solubility of the oil agent (B) and exhibits the effect of thickening the oil agent (B). It is preferable in that

  The molecular weight of the compound (A) of the present invention is, for example, about 500 to 1300, preferably 700 to 1200, particularly preferably 800 to 1100. 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 thickening effect tends to be reduced.

The compound (A) of the present invention can be produced, for example, by the following method.
1. Method of reacting benzenetetracarboxylic acid with thionyl chloride to obtain benzenetetracarboxylic acid tetrachloride, and reacting the resulting benzenetetracarboxylic acid tetrachloride with an amine 2. Benzenetetracarboxylic acid dianhydride with an amine (1 ) To obtain an amic acid, and the amine (2) is condensed using a condensing agent.

  As the benzenetetracarboxylic acid used in the above production method 1, 1,2,4,5-benzenetetracarboxylic acid can be suitably used.

Examples of the amine (R ² —NH ₂ , R ³ —NH ₂ ; R ² and R ³ are the same as described above) used in the production method of 1 above include, for example, hexylamine, octylamine, 2-ethylhexylamine, decylamine, Aliphatic hydrocarbon groups having 6 or more carbon atoms (preferably 6 to 20 carbon atoms) such as laurylamine, myristylamine, stearylamine, oleylamine, etc. (preferably linear or branched alkyl groups, alkenyl groups, Or an amine having an alkynyl group).

  In the production method of 1 above, the reaction of benzenetetracarboxylic acid tetrachloride and amine can be carried out, for example, by dropping benzenetetracarboxylic acid tetrachloride into a system charged with amine.

The amount of amine used (the sum of the amounts used of R ² —NH ₂ and R ³ —NH ₂ ) is, for example, about 4 to 8 mol, preferably 4 to 6 mol, per 1 mol of benzenetetracarboxylic acid tetrachloride. is there.

The proportion of _{^{R 2 -NH 2, R 3 -NH}} 2 ( the former: the latter, the molar ratio) can be appropriately adjusted depending on the compound represented by the desired Formula (1). That is, the (CONH-R ² ) group and the (CONH-R ³ ) group in the compound represented by the formula (1) obtained by adjusting the ratio of R ² —NH ₂ and R ³ —NH ₂ used. The number of can be controlled.

  The reaction of benzenetetracarboxylic acid tetrachloride and 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 alone or in combination of two or more.

  The amount of the solvent used is, for example, about 50 to 300% by weight with respect to the total amount of benzenetetracarboxylic acid tetrachloride 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 benzenetetracarboxylic acid tetrachloride 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 about 30-60 degreeC, for example. The reaction time (= dropping time) is, for example, about 0.5 to 20 hours. After completion of the reaction (= dropping), an aging step may be provided. When the aging step is provided, the aging temperature is, for example, about 30 to 60 ° C., and the aging time is, for example, about 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 above production method 2, for example, benzenetetracarboxylic dianhydride, amine (1) and the following solvent are charged into the system and aged to form an amic acid. Thereafter, amine (2) and condensing agent ( For example, a compound represented by the formula (1) can be produced by charging and aging carbodiimide or a salt thereof.

  As the benzenetetracarboxylic dianhydride used in the above production method 2, 1,2,4,5-benzenetetracarboxylic acid-1,2: 4,5-dianhydride can be preferably used. .

In the above production method 2, one of R ² —NH ₂ and R ³ —NH ₂ is used as the amine (1) and the other is used as the amine (2). Examples of R ² —NH ₂ and R ³ —NH ₂ include the same examples as those of the amine that can be used in the above production method 1.

  As usage-amount of amine (1), it is about 2-4 mol with respect to 1 mol of benzenetetracarboxylic dianhydrides, Preferably it is 2-3 mol. Moreover, as the usage-amount of amine (2), it is about 2-4 mol with respect to 1 mol of benzenetetracarboxylic dianhydrides, 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 3 to 8 membered cyclo It is an alkyl group. R and R ′ may be the same or different. R and R ′ may be bonded to each other to form a ring together with a (—N═C═N—) group.

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

  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. These can be used alone or in combination of two or more.

  The amount of carbodiimide used is, for example, about 2 to 6 mol, preferably 2 to 4 mol, per 1 mol of benzenetetracarboxylic dianhydride.

  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 about 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, about 30 to 70 ° C. The aging time of benzenetetracarboxylic dianhydride and amine is, for example, about 0.5 to 5 hours, and the aging time of amic acid and amine is, for example, about 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.

The compound (A) of the present invention can self-associate by hydrogen bonding at the amide bond site to form a fibrous self-organized body. Furthermore, since the R ² and R ³ groups have an affinity for the oil agent (B), the oil agent (B) can be thickened appropriately and stably over time by being compatible with the oil agent (B). Can do. Furthermore, the compound (A) of the present invention has moderate crystallinity because the R ² and R ³ groups are different from each other. Therefore, the viscosity of the oil agent (B) can be increased without limiting, and when the oil agent (B) has transparency, the viscosity can be increased while maintaining the transparency.

[Oil agent (B)]
The oil agent of the present invention 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 glycol Isooctanoate sulfonate, etc.), aromatic 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).

  The content of the compound (A) in the total amount of the oil composition of the present invention (the total amount when containing two or more) is, for example, about 0.5 to 10.0% by weight, preferably 0.7 to 4.0. % By weight. In addition, the content of the compound (A) (when two or more types are contained, the total amount thereof) is, for example, 0.5 to 10 parts per 100 parts by weight of the oil agent (B) contained in the total amount of the oil composition of the present invention. About 0 part by weight, preferably 0.7 to 4.0 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 processing fluid.

  The content of the oil agent (B) in the total amount of the oil composition of the present invention (the total amount when two or more are contained) is, for example, about 90.0 to 99.5% by weight, preferably 96.0 to 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 another thickener exceeds the said range, there exists a tendency for the effect of this invention to become difficult to be acquired. In the present invention, a thickener is a compound that dissolves in an oil agent and generates viscosity. A thickener that imparts viscosity to the oil agent (B), a gelling agent that gels the oil agent (B), and an oil agent ( A stabilizer for increasing the viscosity is included for the purpose of uniformly stabilizing the composition containing B).

  The oil composition of the present invention may contain other components (for example, abrasive grains) as necessary in addition to the thickener and the oil agent (B) containing the compound (A).

  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 number of carbon atoms in at least one of R ² and R ³ in the compound (A) is preferably 8 to 20, more preferably carbon. The number is 18-20. 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 carbon number of at least one of R ² and R ³ in the compound (A) is 6 to 7 is preferable.

  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 is not limited as long as it can be cooled to room temperature (for example, 25 ° C.) or lower, and may be gradually cooled at room temperature, or may be rapidly cooled by ice cooling or the like.

The kinematic viscosity [at 40 ° C .; conforming to JIS K 2283 (2000)] of the oil composition of the present invention is, for example, 1 to 200 mm ² / s (preferably 15.0 to 100 mm ² / s, particularly preferably 15.0). Within the range of ˜50 mm ² / s), it can be appropriately selected depending on the application. 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, about 400 ° C. or less, preferably 100 to 350 ° C., particularly preferably 150 to 300 ° C., and most preferably 200 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 of an apparatus 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, Processing fluid for cutting of brittle materials such as neodymium (cutting oil composition), processing fluid for drilling shale oil (oil composition for drilling), and CMP (Chemical Mechanical Polishing) It is useful as a raw material for an abrasive for polishing (= CMP slurry).

  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 (2-ethylhexylamide) 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, and thermocouple 3.0 g (0.014 mol) of the product 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, 3.6 g (0.028 mol) of 2-ethylhexylamine 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 (2-ethylhexylamide) di ( Oleylamide) [1,2,4,5-benzenetetracarboxylic acid-1,4-di (2-ethylhexylamide) -2,5-di (oleylamide) and 1,2,4,5-benzenetetracarboxylic 5.9 g of a mixture of acid-1,5-di (2-ethylhexylamide) -2,4-di (oleylamide), molecular weight: 975] (yield: 51%, 5% weight loss temperature: 290) ° C). The structure of the reaction product was confirmed by ¹ H-NMR.
¹ H-NMR (270MHz, CDCl ₃ ): δ 0.81-1.02 (m, 18H), 1.03-1.85 (m, 74H), 1.96-2.04 (m, 8H), 3.25-3.40 (m, 4H), 5.22- 5.51 (m, 4H), 8.5-9.5 (m, 2H)
FAB-MS m / z: 973 (Calcd. For C ₆₂ H ₁₁₀ N ₄ O ₄ : 974)

Synthesis Example 2 [Synthesis of thickener (2) (1,2,4,5-benzenetetracarboxylic acid di (2-ethylhexylamide) di (stearylamide))]
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, and thermocouple 3.0 g (0.014 mol) of the product and 7.5 g (0.028 mol) of stearylamine were charged. The system temperature was set to 50 ° C. and aged for 3 hours.
Thereafter, 3.6 g (0.028 mol) of 2-ethylhexylamine 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 (2-ethylhexylamide) di ( Stearylamide) [1,2,4,5-benzenetetracarboxylic acid-1,4-di (2-ethylhexylamide) -2,5-di (stearylamide) and 1,2,4,5-benzenetetracarboxylic Acid-1,5-di (2-ethylhexylamide) -2,4-di (stearylamide), molecular weight: 979] was obtained (yield: 53%, 5% weight loss temperature: 292). ° C). The structure of the reaction product was confirmed by ¹ H-NMR.
¹ H-NMR (270MHz, CDCl ₃ ): δ 0.81-1.10 (m, 18H), 1.10-1.94 (m, 90H), 3.25-3.40 (m, 4H), 8.5-9.5 (m, 2H)
FAB-MS m / z: 977 (Calcd. For C ₆₂ H ₁₁₄ N ₄ O ₄ : 978)

Synthesis Example 3 [Synthesis of thickener (3) (1,2,4,5-benzenetetracarboxylic acid di (2-ethylhexylamide) di (laurylamide))]
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, and thermocouple 3.0 g (0.014 mol) of the product and 5.1 g (0.028 mol) of laurylamine were charged. The system temperature was set to 50 ° C. and aged for 3 hours.
Thereafter, 3.6 g (0.028 mol) of 2-ethylhexylamine 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 (2-ethylhexylamide) di ( Laurylamide) [1,2,4,5-benzenetetracarboxylic acid-1,4-di (2-ethylhexylamide) -2,5-di (laurylamide) and 1,2,4,5-benzenetetracarboxylic A mixture of acid-1,5-di (2-ethylhexylamide) -2,4-di (laurylamide), molecular weight: 810] was obtained (yield: 62%, 5% weight loss temperature: 313). ° C). The structure of the reaction product was confirmed by ¹ H-NMR.
¹ H-NMR (270MHz, CDCl ₃ ): δ 0.34-1.0 (m, 18H), 1.0-2.0 (m, 66H), 2.90-3.40 (m, 4H), 8.5-9.5 (m, 2H)
FAB-MS m / z: 810 (Calcd. For C ₅₀ H ₉₀ N ₄ O ₄ : 810)

Examples 1-3, Comparative Examples 1-3
It mixed by the composition (unit: weight part) shown in Table 1, heated and stirred at 100 degreeC, the oil agent and the thickener were made compatible, and it cooled to 25 degreeC after that, and obtained the 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 ○: More than 27 ° C / sec ×: 27 ° C / sec or less

<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 results are summarized in Table 1.

* 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”

  The oil composition of the present invention has a viscosity suitable for the application, and can maintain the viscosity stably. In addition, it has lubricity, cleanability, and cooling properties. Therefore, when the oil composition of the present invention is used as a working fluid at the time of cutting, lubricity can be imparted, chips can be washed, and processing heat can be cooled. Therefore, it can be suitably used when processing brittle materials such as sapphire, glass, ceramics, silicon, and neodymium. Moreover, when the oil composition of this invention is used, abrasion of a cutting blade and an abrasive grain can be suppressed and the outstanding cutting property can be maintained over a long period of time.

Claims (3)

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 the structural formula of benzene, R ² and R ³ are different from each other, and are aliphatic hydrocarbon groups having 6 or more carbon atoms. N is 1 Represents an integer of ~ 3)
An oil composition for lubricating and / or cleaning and / or cooling comprising the compound (A) represented by formula (A) and the oil agent (B).   The oil composition for lubrication and / or washing and / or cooling according to claim 1, comprising 0.5 to 10% by weight of the compound (A) represented by the formula (1) based on the total amount of the oil composition. 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 the structural formula of benzene, R ² and R ³ are different from each other, and are aliphatic hydrocarbon groups having 6 or more carbon atoms. N is 1 Represents an integer of ~ 3)
The oil composition for cutting process containing the compound (A) represented by these, and an oil agent (B).