JPH09217073A - Lubricant oil for metal processing - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a lubricant oil for a metal processing containing a specified alicyclic polycarboxyl ester, very small in increase in an acid value because of a good hydrolysis resistance, small in change in a metal surface by the user thereof, useful as an oil for a metal cutting etc., and especially suitable for using as a water-soluble lubricant oil. SOLUTION: This lubricant oil for metal processing except as rolling oil contains a compound of the formula [A is a cyclohexane ring or a cyclohexene ring; R<1> is H or CH3 ; X is H or a group of the formula, COOR<4> (R<4> is a 3-18C branched alkyl, a 3-10 cycloalkyl or a 1-18C linear alkyl); Y is equal to the X; R<2> and R<3> is each equal to the R<4> ] (e.g. a product of an esterification reaction of an acid component such as 1,2-cyclohexanedicarboxylic acid, 4- cyclohexene-1,2-dicarboxylic acid and these acid anhydrides with an alcohol component such as isobutanol and n-octadecanol). The content of the compound of the formula is preferably >=10wt.%.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a lubricating oil for metal processing other than a metal rolling oil. More specifically, the present invention relates to an oil agent for cutting, grinding, pressing, forging, extruding, drawing and the like of metals, and particularly relates to a lubricating oil suitable for metal working when it is used as a water-soluble material.

[0002]

2. Description of the Related Art Conventionally, cutting, grinding, press working, forging,
As an oil agent used for metal processing such as extrusion and drawing, a non-aqueous oil agent using mineral oil or fats and a water-soluble oil agent in which these base oils are dissolved in water by a surfactant or made into an emulsion are used. Has been. In recent years, the processing speed tends to increase in order to improve productivity, and cooling of the processed surface is becoming more important. Further, flame retardancy is required to avoid the ignition of the oil. The water-soluble oil is
It is superior to non-water-based oils in terms of economy, cooling, and safety, and the specific gravity of water-soluble oils is large.

However, a drawback of water-soluble oil agents is that they are inferior in lubricity, especially under low-speed processing conditions, to non-aqueous oil agents. For the purpose of resolving this drawback, a naphthene-based mineral oil has been mainly used as a base oil of a water-soluble oil agent, but as an oil agent having improved lubricity, natural fats and oils or synthetic esters are added as a base oil or to mineral oil. It has come to be used in the form. The synthetic ester is mainly a fatty acid methyl ester or an ester of neopentyl polyol such as trimethylolpropane and oleic acid.

Water-soluble oil agents are generally the aforementioned oils and fats and / or
Alternatively, a synthetic ester mixed with a surfactant and other necessary additives is diluted with water by 10 to 100 times before use. This water-soluble oil agent has better lubricity than that using mineral oil. However, since it is an ester, it has the drawback of being hydrolyzed. Therefore, when used as an aqueous processing oil for a long time or stored for a long time, the ester decomposes into an acid and an alcohol by hydrolysis, and the performance of the oil agent changes. As a result, the metal is rusted or corroded, or the oil agent is separated and non-uniformized to deteriorate the processing performance. Further, also in the non-aqueous oil agent, an ester is used as an oiliness agent component, which may cause a problem of performance deterioration of the oil agent due to hydrolysis.

[0005]

Under these circumstances, the present invention has an object to provide a base oil ester for metalworking oil which has good hydrolysis stability.

[0006]

As a result of intensive studies to solve the above problems, the present inventors have found that a specific alicyclic polycarboxylic acid ester achieves a predetermined object,
The present invention has been completed based on such findings.

That is, the lubricating oil for metalworking excluding the rolling oil according to the present invention is one or two of the alicyclic polycarboxylic acid ester represented by the general formula (1) (hereinafter referred to as "the present ester"). It is characterized by containing at least one species.

[0008]

Embedded image [In the formula, A represents a cyclohexane ring or a cyclohexene ring. R ¹ represents a hydrogen atom or a methyl group. X represents a hydrogen atom or COOR ⁴ . Y represents a hydrogen atom or COOR ⁵ . ^{R 2, R 3, R 4} , R 5 are the same or different, branched alkyl group having 3 to 18 carbon atoms, straight-chain alkyl having from 1 to 18 cycloalkyl group carbon atoms or 3 to 10 carbon atoms Represents a group. ]

This ester is obtained by esterifying a predetermined acid component and an alcohol component in a conventional manner, preferably under an inert gas atmosphere such as nitrogen, in the presence or absence of an esterification catalyst, while heating and stirring. Is a compound prepared by

Examples of the acid component according to the present invention include cycloalkane polycarboxylic acid or cycloalkene polycarboxylic acid and their acid anhydrides, and the substitution position and stereo configuration of each carboxyl group are not limited.

Specifically, 1,2-cyclohexanedicarboxylic acid, 4-cyclohexene-1,2-dicarboxylic acid, 1-cyclohexene-1,2-dicarboxylic acid,
3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, 3-methyl-1,2-cyclohexanedicarboxylic acid, 4-methyl-1,2-cyclohexanedicarboxylic acid, 3-methyl-4-cyclohexene-1,
2-dicarboxylic acid, 4-methyl-4-cyclohexene-
Examples include 1,2-dicarboxylic acid, 1,2,4-cyclohexanetricarboxylic acid, 1,3,5-cyclohexanetricarboxylic acid, 1,2,4,5-cyclohexanetetracarboxylic acid and acid anhydrides thereof, and among them, 1,2-cyclohexanedicarboxylic acid, 4-methyl-1,2-cyclohexanedicarboxylic acid, 4-cyclohexene-1,2
-Dicarboxylic acid, 4-methyl-4-cyclohexene-
1,2-Dicarboxylic acids and their anhydrides are preferred.

As the above-mentioned acid component, the above-mentioned carboxylic acid or its acid anhydride can be used alone, or can be esterified with two or more kinds of compounds.

The alcohol component constituting the present ester is a branched alcohol having 3 to 18 carbon atoms, or 3 to 1 carbon atoms.
0 cycloalcohol or a linear alcohol having 1 to 18 carbon atoms.

Specific branched alcohols include isopropanol, isobutanol, sec-butanol, isopentanol, isohexanol, 2-methylhexanol, 1-methylheptanol, 2-methylheptanol, isoheptanol, 2- Ethylhexanol, 2-
Octanol, isooctanol, 3,5,5-trimethylhexanol, isodecanol, isododecanol, isotridecanol, isotetradecanol, isohexadecanol, isooctadecanol, 2,6-dimethyl-4-heptanol, etc. Is exemplified.

Examples of cycloalcohol include cyclohexanol, methylcyclohexanol, dimethylcyclohexanol and the like.

Further, as the linear alcohol, methanol, ethanol, n-propanol, n-butanol, n-pentanol, n-hexanol, n-heptanol, n-octanol, n-nonanol, n-decanol, n -Dodecanol, n-tetradecanol, n
Examples include hexadecanol, n-octadecanol, and 2-octadecenol.

In carrying out the esterification reaction, the alcohol component is, for example, 1.0 to 1.5 with respect to 1 equivalent of the acid component.
Equivalent, preferably about 1.05 to 1.2 equivalent.

As the alcohol component, the above alcohols can be used alone, or can be esterified with a mixture of two or more alcohols.

Further, in place of the above acid component and alcohol component, a lower alcohol ester of the acid component and / or an acetic acid ester of the alcohol component, a propionic acid ester or the like is used, and the alicyclic polycarboxylic acid ester is subjected to a transesterification reaction. It is also possible to obtain

Examples of the esterification catalyst include tetraalkyl titanate, stannous oxide, paratoluene sulfonic acid and the like. For example, 0.1 to 0.4 based on the total weight of the raw material acid component and alkali component. Used by weight percent.

The esterification temperature is from 150 ° C to 23 ° C.
0 ° C is exemplified, and the reaction is usually completed in 3 to 30 hours.

The alicyclic polycarboxylic acid ester according to the present invention can also be obtained by subjecting the corresponding aromatic polycarboxylic acid ester to nuclear hydrogenation.

Among the alicyclic polycarboxylic acid branched alkyl esters and cycloalkyl esters thus obtained, in particular, diisobutyl 1,2-cyclohexanedicarboxylate, dicyclohexyl 1,2-cyclohexanedicarboxylate, diisoheptyl 1,2-cyclohexanedicarboxylate 1,2-cyclohexanedicarboxylic acid di (2-ethylhexyl), 1,2-cyclohexanedicarboxylic acid di (3,5,5-trimethylhexyl),
2-Cyclohexanedicarboxylic acid di (2,6-dimethyl-4-heptyl), 1,2-cyclohexanedicarboxylic acid diisodecyl, 1,2-cyclohexanedicarboxylic acid diisotridecyl, 4-cyclohexene-1,2-dicarboxylic acid dibutyl, 4- Cyclohexene-1,2-dicarboxylic acid dicyclohexyl, 4-cyclohexene-1,
2-dicarboxylic acid diisoheptyl, 4-cyclohexene-1,2-dicarboxylic acid di (2-ethylhexyl), 4
-Cyclohexene-1,2-dicarboxylic acid di (3,5,5
5-trimethylhexyl), 4-cyclohexene-1,
2-dicarboxylic acid di (2,6-dimethyl-4-heptyl), 4-cyclohexene-1,2-dicarboxylic acid diisodecyl, 4-cyclohexene-1,2-dicarboxylic acid diisotridecyl, 3-methyl-1,2-cyclohexane Dicarboxylic acid diisobutyl, 3-methyl-1,2-cyclohexanedicarboxylic acid dicyclohexyl, 3-methyl-1,2-cyclohexanedicarboxylic acid diisoheptyl, 3-methyl-1,2-cyclohexanedicarboxylic acid di (2-ethylhexyl), 3- Methyl-1,2-cyclohexanedicarboxylic acid di (3,5,5-trimethylhexyl), 3-methyl-1,2-cyclohexanedicarboxylic acid di (2,6-dimethyl-4-heptyl), 3-methyl-1 , 2-Cyclohexanedicarboxylic acid diisodecyl, 3-methyl-1 2-Cyclohexanedicarboxylic acid diisotridecyl, 4-methyl-1,2-cyclohexanedicarboxylic acid diisobutyl, 4-methyl-1,2-cyclohexanedicarboxylic acid dicyclohexyl, 4-methyl-1,2-cyclohexanedicarboxylic acid diisoheptyl, 4-methyl- 1,2-Cyclohexanedicarboxylic acid di (2-ethylhexyl), 4-methyl-1,2-cyclohexanedicarboxylic acid di (3,5,5-trimethylhexyl), 4-methyl-1,2-cyclohexanedicarboxylic acid di ( 2,6-dimethyl-4-heptyl), 4-methyl-1,2-cyclohexanedicarboxylic acid diisodecyl, 4-methyl-1,2-cyclohexanedicarboxylic acid diisotridecyl, 3-methyl-4-cyclohexene-
1,2-dicarboxylic acid diisobutyl, 3-methyl-4-
Cyclohexene-1,2-dicarboxylic acid dicyclohexyl, 3-methyl-4-cyclohexene-1,2-dicarboxylic acid diisoheptyl, 3-methyl-4-cyclohexene-1,2-dicarboxylic acid di (2-ethylhexyl),
3-Methyl-4-cyclohexene-1,2-dicarboxylic acid di (3,5,5-trimethylhexyl), 3-methyl-4-cyclohexene-1,2-dicarboxylic acid di (2,2
6-dimethyl-4-heptyl), 3-methyl-4-cyclohexene-1,2-dicarboxylic acid diisodecyl, 3-
Methyl-4-cyclohexene-1,2-dicarboxylic acid diisotridecyl, 4-methyl-4-cyclohexene-
1,2-dicarboxylic acid diisobutyl, 4-methyl-4-
Cyclohexene-1,2-dicarboxylic acid dicyclohexyl, 4-methyl-4-cyclohexene-1,2-dicarboxylic acid diisoheptyl, 4-methyl-4-cyclohexene-1,2-dicarboxylic acid di (2-ethylhexyl),
4-Methyl-4-cyclohexene-1,2-dicarboxylic acid di (3,5,5-trimethylhexyl), 4-methyl-4-cyclohexene-1,2-dicarboxylic acid di (2,2
6-dimethyl-4-heptyl), 4-methyl-4-cyclohexene-1,2-dicarboxylic acid diisodecyl, 4-
One or two selected from the group consisting of methyl-4-cyclohexene-1,2-dicarboxylic acid diisotridecyl
At least one ester is recommended.

The alicyclic polycarboxylic acid linear alkyl ester is usually used in combination with one or more of the above-mentioned alicyclic polycarboxylic acid branched alkyl esters and / or cycloalkyl esters. preferable. Specific examples of the linear alkyl ester include 1,2-cyclohexanedicarboxylic acid didecyl, 1,2-cyclohexanedicarboxylic acid didodecyl, 1,2-cyclohexanedicarboxylic acid ditetradecyl, 1,2-cyclohexanedicarboxylic acid dihexadecyl, 1,2. -Cyclohexanedicarboxylic acid dioctadecyl, 4-cyclohexene-
1,2-dicarboxylic acid didecyl, 4-cyclohexene-
1,2-dicarboxylic acid didodecyl, 4-cyclohexene-1,2-dicarboxylic acid ditetradecyl, 4-cyclohexene-1,2-dicarboxylic acid dihexadecyl, 4-cyclohexene-1,2-dicarboxylic acid dioctadecyl,
3-Methyl-1,2-cyclohexanedicarboxylic acid didecyl, 3-methyl-1,2-cyclohexanedicarboxylic acid didodecyl, 3-methyl-1,2-cyclohexanedicarboxylic acid ditetradecyl, 3-methyl-1,2-cyclohexanedicarboxylic acid Dihexadecyl, 3-methyl-
1,2-cyclohexanedicarboxylic acid dioctadecyl,
4-Methyl-1,2-cyclohexanedicarboxylic acid didecyl, 4-methyl-1,2-cyclohexanedicarboxylic acid didodecyl, 4-methyl-1,2-cyclohexanedicarboxylic acid ditetradecyl, 4-methyl-1,2-cyclohexanedicarboxylic acid Dihexadecyl, 4-methyl-
1,2-cyclohexanedicarboxylic acid dioctadecyl,
3-Methyl-4-cyclohexene-1,2-dicarboxylic acid didecyl, 3-methyl-4-cyclohexene-1,2
-Dicarboxylic acid didodecyl, 3-methyl-4-cyclohexene-1,2-dicarboxylic acid ditetradecyl, 3-methyl-4-cyclohexene-1,2-dicarboxylic acid dihexadecyl, 3-methyl-4-cyclohexene-1,2
-Dioctadecyl dicarboxylate, 4-methyl-4-cyclohexene-1,2-dicarboxylic acid didecyl, 4-methyl-4-cyclohexene-1,2-dicarboxylic acid didodecyl, 4-methyl-4-cyclohexene-1,2- One or more ester selected from the group consisting of ditetradecyl dicarboxylate, 4-methyl-4-cyclohexene-1,2-dicarboxylic acid dihexadecyl, and 4-methyl-4-cyclohexene-1,2-dicarboxylic acid dioctadecyl. Etc. can be illustrated.

Further, an alicyclic polycarboxylic acid ester is prepared by using, as the alcohol component, a mixture of one or more kinds of branched alcohol and / or cycloalcohol and one or more kinds of linear alcohol. It is also possible to synthesize them.

The alcohol component in the alicyclic polycarboxylic acid ester composition thus obtained has 1 to 1 carbon atoms.
It is recommended that the total linear alcohol content of 8 is 50 mol% or less.

Generally, when an ester is exposed to high temperature in the presence of water, it decomposes into a predetermined carboxylic acid and alcohol. It is considered that the stability is high if the increase in the acid value of the ester hydrolyzate is small. When compared by this method, beef tallow, 2-ethylhexyl palmitate, isobutyl stearate, oleic acid ester of trimethylolpropane, and coconut oil fatty acid methyl that have been conventionally used as base oils of metalworking oils have increased acid values. large. In addition, the weight change of iron pieces immersed in oil is large, and iron, copper,
The state of the surface of metal pieces such as aluminum also changes due to corrosion.

On the other hand, cycloalkane polycarboxylic acid ester or cycloalkene polycarboxylic acid ester has a small increase in acid value. Also, the change in iron weight is slight,
There is almost no change in the appearance of the metal surface.

The content of the ester in the lubricating oil is recommended to be 10% by weight or more. If it is less than 10% by weight, hydrolysis stability is poor.

Further, the lubricating oil for metalworking excluding the rolling oil according to the present invention includes other base oils besides the present ester, for example, mineral oils, synthetic hydrocarbon oils, animal and vegetable oils, and esters other than the present ester (hereinafter referred to as “combined use”). It is also possible to mix 1 type (s) or 2 or more types (referred to as “ester”).

Examples of the mineral oil include paraffin base crude oil, intermediate base crude oil and naphthene base crude oil.

Examples of synthetic hydrocarbon oils include low molecular weight polybutene, low molecular weight polypropylene, α-olefin oligomers having 8 to 14 carbon atoms, hydrogenated compounds thereof, alkylbenzene and the like.

Examples of animal and vegetable oils include beef tallow, lard, palm oil, coconut oil and rapeseed oil.

Examples of the combined ester include fatty acid monoester, adipic acid ester, azelaic acid ester, sebacic acid ester, phthalic acid ester, trimellitic acid ester and polyol ester.

The content of mineral oil, synthetic hydrocarbon oil, animal and vegetable oil and / or combined ester in the lubricating oil is recommended to be 10 to 90% by weight.

[0036]

BEST MODE FOR CARRYING OUT THE INVENTION The lubricating oil for metalworking excluding rolling oil according to the present invention includes a surfactant, an extreme pressure additive, a rust preventive agent, a vapor phase rust preventive agent, a metal in order to improve the performance of the base oil. It is also possible to appropriately mix one or more anticorrosives, coupling agents, pour point depressants, thickeners, antiseptic germicides, defoamers, dyes, fragrances, and other known additives. . The contents of these additives are the same as those of conventional metalworking oils. Although not particularly limited as long as the predetermined effect is achieved, a specific example thereof will be described below.

Examples of the surfactant include fatty acid soap, sulfuric acid ester type, sulfonic acid type anionic type and polyoxyethylene type, polyhydric alcohol type, alkylolamide type nonionic type and the like.

As the extreme pressure additive, chlorinated paraffin,
Chlorinated fatty acids, chlorinated fatty acid esters and other chlorine-based compounds, sulfurized mineral oil, sulfurized fats and oils and other sulfur-based compounds, phosphoric acid esters, phosphite ester and other phosphorus-based compounds, etc. It may be blended.

Examples of rust inhibitors include carboxylates, sulfonates, amines such as triethanolamine, amides such as oleic acid diethanolamide and adipic acid cyclohexylamide, esters such as sorbitan oleate, sebacic acid and the like. Dibasic acids, nitrites, phosphates,
There are inorganic materials such as borate.

Examples of vapor-phase rust inhibitors include lower amine nitrites, morpholine and cyclohexylamine.

Examples of the metal anticorrosive agent include benzotriazole, imidazoline, mercaptobenzothiazole and thiodiazole polysulfide.

Examples of coupling agents include butyl diglycol and butyl cellosolve.

Examples of pour point depressants include ethylene glycol and propylene glycol.

Examples of the thickener include polyalkylene glycols, cellulose derivatives, sodium polyacrylate and the like.

Examples of the antiseptic disinfectant include phenolic compounds such as o-phenylphenol and p-chloro-m-xylenol, hexahydrotriazine and 2-hydroxymethyl-
There are formaldehyde donors such as 2-nitro-1,3-propanediol.

Examples of the defoaming agent include silicone, higher alcohol, polyalkylene glycol, fluorine-based polyether and the like.

When the lubricating oil for metalworking prepared by the above method is used as a water-soluble oil agent, it is diluted with water by 10 to 100 times.

[0048]

The present invention will be described below in detail with reference to examples, but the present invention is not limited to the examples. still,
The properties of the lubricating oil in each example were evaluated by the following methods.

Hydrolysis stability test A glass test tube having an inner diameter of 6.6 mm and a height of 30 cm was charged with a wire of iron, copper and aluminum having a length of 4 cm, and a sample ester was added to 2.0.
g, 0.2 g of distilled water is weighed. While degassing with an aspirator, seal the test tube and put it in an oven at 160 ° C.
Heat for 16 hours. After that, the sample is taken out, the acid value is measured, and the surface condition of the wire is visually observed.

Kinematic viscosity is measured according to JIS-K-2283 using an Ubbelohde viscometer.

Pour point Measured according to JIS-K-2269.

Production Example 1 4-cyclohexene-1,2-dicarboxylic acid anhydride (in this product, maleic anhydride and 1,3 were added to a 4-necked flask equipped with a stirrer, a thermometer, and a water distiller equipped with a cooling tube. -Prepared by subjecting butadiene to the usual Diels-Alder reaction) 152.1 g (1 mol), 2-ethylhexanol 286.5 g (2.2 mol) and tetrabutyl titanate 0.5 g, and gradually adding 200 ° C under reduced pressure
Temperature. An esterification reaction was carried out for about 9 hours while taking the produced water into a water fractionator. After the reaction, excess 2-ethylhexanol was removed by distillation, neutralized with a 10% aqueous sodium hydroxide solution, and then washed with water until neutral. Activated carbon, activated clay and activated alumina were added for adsorption purification, followed by filtration to obtain 343.2 g of di (2-ethylhexyl) 4-cyclohexene-1,2-dicarboxylate.

Example 1 The hydrolytic stability of 4-cyclohexene-1,2-dicarboxylic acid di (2-ethylhexyl) obtained in Production Example 1 was evaluated. Table 1 shows the obtained results.

Examples 2 to 11 Reactions and purifications were carried out in the same manner as in Production Example 1 to prepare the esters shown in Table 1, and the hydrolysis stability of these was evaluated. Table 1 shows the obtained results.

Example 12 The compound of Example 2 and the compound of Example 3 were mixed in a weight ratio of 1: 1.
Was mixed to prepare a compound of Example 12, and the hydrolysis stability of this compound was evaluated. Table 1 shows the obtained results.

[0056]

[Table 1]

Comparative Example 1 Commercially available beef tallow was directly used as a sample of Comparative Example 1 to evaluate hydrolysis stability. Table 2 shows the obtained results.

Production Example 2 134 g of trimethylolpropane were placed in the same apparatus as in Production Example 1.
(1.0 mol), 864 g (3.06 mol) of oleic acid
Then, 2.0 g of stannous oxide was charged, the reaction was carried out for 8 hours in the same manner as in Production Example 1, and post-treatment was carried out to prepare the desired trimethylolpropane trioleate.

Comparative Example 2 The trimethylolpropane trioleate obtained in Production Example 2 was evaluated for hydrolysis stability. Table 2 shows the obtained results.

Production Example 3 384 g (1.5 mol) of palmitic acid and 234 g (1.8 mol) of 2-ethylhexanol were placed in the same apparatus as in Production Example 1.
Then, 0.6 g of tetrabutyl titanate was charged, the reaction was carried out for 6 hours in the same manner as in Production Example 1, and post-treatment was carried out to prepare the target 2-ethylhexyl palmitate.

Comparative Example 3 The hydrolysis stability of 2-ethylhexyl palmitate obtained in Production Example 3 was evaluated. Table 2 shows the obtained results.

Comparative Example 4 Isobutyl stearate was prepared by reacting and purifying in the same manner as in Production Example 3, and the hydrolysis stability of this was evaluated. Table 2 shows the obtained results.

Production Example 5 192 g of trimellitic acid anhydride was placed in the same apparatus as in Production Example 1.
(1.0 mol), 4-ethylhexanol 429 g
(3.3 mol) and tetrabutyl titanate (0.6 g) were charged, the reaction was carried out for 6 hours in the same manner as in Production Example 1, and post-treatment was carried out to prepare the intended tri (2-ethylhexyl) trimellitate.

Comparative Example 5 The hydrolytic stability of tri (2-ethylhexyl) trimellitate obtained in Production Example 5 was evaluated. The obtained result is
It is shown in the table.

Comparative Example 6 Hydrolysis stability of methyl ester of C _{12 to} C ₁₈ fraction of coconut oil fatty acid was evaluated. Table 2 shows the obtained results.

[0066]

[Table 2]

Example 13 4-Cyclohexene-1,2-dicarboxylic acid di (2-ethylhexyl) "abbreviation: DOTP" and paraffinic mineral oil (500 neutral) were mixed at a weight ratio of 1: 1 to obtain the mixture. The kinematic viscosity, pour point and hydrolytic stability of the oil were measured. Table 3 shows the results.

Example 14 4-Cyclohexene-1,2-dicarboxylic acid diisodecyl "abbreviation: DIDTP" and beef tallow were mixed in a weight ratio of 1: 1 and the resulting mixed oil had kinematic viscosity, pour point and hydrolysis stability. The sex was measured. Table 3 shows the results.

Example 15 4-Cyclohexene-1,2-dicarboxylic acid ester (equimolar mixture of isodecyl alcohol and tetradecanol as alcohol component) "Mixed ester 1" and beef tallow were mixed in a weight ratio of 1: 1. , The kinematic viscosity of the obtained mixed oil,
Pour point and hydrolytic stability were measured. The result is the third
It is shown in the table.

Example 16 4-Cyclohexene-1,2-dicarboxylic acid ester (equimolar mixture of isodecyl alcohol and tetradecanol as alcohol component) "Mixed ester 1" and trimellitic acid tri (2-ethylhexyl) Weight ratio 1:
The resulting mixed oil was mixed at 1 and the kinematic viscosity, pour point and hydrolysis stability were measured. Table 3 shows the results.

Example 17 4-Cyclohexene-1,2-dicarboxylic acid ester (equimolar mixture of isodecyl alcohol and tetradecanol as alcohol component) "Mixed ester 1" and trimethylolpropane trioleate in a weight ratio of 1: The resulting mixed oil was mixed at 1 and the kinematic viscosity, pour point and hydrolysis stability were measured. Table 3 shows the results.

Example 18 1,2-Cyclohexanedicarboxylic acid ester (equimolar mixture of isodecyl alcohol and tetradecanol as alcohol component) "Mixed ester 3" and beef tallow were mixed at a weight ratio of 1: 1 to obtain a mixture. The kinematic viscosity, pour point and hydrolytic stability of the obtained mixed oil were measured. Table 3 shows the results.

Comparative Example 7 Paraffinic mineral oil (500 neutral) was used as a sample of Comparative Example as it was, and the kinematic viscosity and the pour point were evaluated. Table 3 shows the obtained results.

[0074]

[Table 3]

[0075]

INDUSTRIAL APPLICABILITY The lubricating oil for metalworking excluding rolling oil according to the present invention includes beef tallow, fatty acid monoesters, oleic acid ester of trimethylolpropane, and coconut oil fatty acid methyl ester, which have been conventionally used for metalworking oils. Hydrolysis stability is better than that of Therefore, the increase of the acid value is remarkably small, and the surface change of the metal is small.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Internal reference number FI Technical indication location C10N 30:12 40:24 (72) Inventor Ichiro Fushimi 13 Yahamachi, Hakashijima, Fushimi-ku, Kyoto Within Nippon Rika Co., Ltd.

Claims (5)

[Claims] 1. A lubricating oil for metalworking, excluding rolling oil, containing one or more alicyclic polycarboxylic acid esters represented by the general formula (1). Embedded image [In the formula, A represents a cyclohexane ring or a cyclohexene ring. R ¹ represents a hydrogen atom or a methyl group. X represents a hydrogen atom or COOR ⁴ . Y represents a hydrogen atom or COOR ⁵ . ^{R 2, R 3, R 4} , R 5 are the same or different, branched alkyl group having 3 to 18 carbon atoms, straight-chain alkyl having from 1 to 18 cycloalkyl group carbon atoms or 3 to 10 carbon atoms Represents a group. ] 2. An alicyclic polycarboxylic acid ester comprising:
2-cyclohexanedicarboxylic acid, 4-cyclohexene-1,2-dicarboxylic acid, 3-methyl-1,2-cyclohexanedicarboxylic acid, 4-methyl-1,2-cyclohexanedicarboxylic acid, 3-methyl-4-cyclohexene-1 2. An ester having an acid component of one or more compounds selected from the group consisting of 1,2-dicarboxylic acid, 4-methyl-4-cyclohexene-1,2-dicarboxylic acid and their anhydrides. Lubricating oil for metal processing, excluding the rolling oil described in. 3. The alicyclic polycarboxylic acid ester is isobutanol, isoheptanol, isodecanol, 2-
Ethylhexanol, 3,5,5-trimethylhexanol, cyclohexanol, isotridecanol, 2,
6-dimethyl-4-heptanol, n-decanol, n
-Dodecanol, n-tetradecanol, n-hexadecanol and n-octadecanol, which is an ester having an alcohol component of one or more compounds selected from the group consisting of n-octadecanol. Lubricating oil for metal processing excluding the rolling oil described. 4. One or two kinds represented by the general formula (1)
In at least one kind of alicyclic polycarboxylic acid ester,
^4. The content of the linear alkyl group having 1 to 18 carbon atoms in R ² , R ³ , R ⁴ and R ⁵ is 50 mol% or less. Lubricating oil for metal processing excluding the rolling oil of. 5. The lubricating oil for metalworking excluding the rolling oil according to claim 1, wherein the content of the alicyclic polycarboxylic acid ester is 10% by weight or more.