JPH10204465A - Water-soluble working fluid - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a water-soluble working fluid, excellent in workability, defoaming and rust preventing properties and antimicrobial activities and useful for working such as cutting, grinding, rolling or forging of metals by including a reactional product (salt) of a specific adamantanecarboxylic acid with an alkanolamine therein. SOLUTION: This water-soluble metal working fluid comprises one or more selected from the group consisting of a reactional product of an adamantanecarboxylic acid represented by the formula R is H, a lower alkyl or (CH2 )n COOH [(n) is 0-3]; (m) is 0-3} such as 1-adamantaneacetic acid with an alkanolamine such as monoethanolamine and a salt thereof. The reactional product (salt) is preferably compounded in an amount of 5-80wt.%.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a water-soluble processing oil used for processing metal. More specifically, the present invention relates to a water-soluble processing oil used for processing such as metal cutting, grinding, rolling, and forging.

[0002]

2. Description of the Related Art Conventionally, oil-type processing oils have been used as metal processing oils, but water-soluble processing oils have been used instead of oil-soluble oils in view of fire danger and workability. . In particular, in cutting and grinding, a water-soluble processing oil is widely used because of its excellent cooling property. These water-soluble processing oils include lubricants, extreme pressure additives, rust inhibitors, surfactants (fatty acids such as oleic acid and castor oil fatty acids, alkali metal salts such as naphthenic acid and rosin acid, or amine salts). The main component is the main component), but the workability is generally poor due to the large amount of foaming, and the water is used after being diluted with water. There was a problem that rust easily occurred.

Conventionally, preservatives have been used to prevent the degradation of microorganisms. However, preservatives have problems in that they tend to cause rough hands and are not persistent. Several proposals have been made to solve such problems that performance deterioration and rust easily occur due to such foaming and microbial decomposition. For example,
JP-A-62-70493 discloses amino acids and derivatives thereof, JP-A-58-67792 describes polyaminoamide compounds, and JP-A-61-272292 describes alkanolamine esters having an aromatic ring or a cyclo ring. Has been proposed.

[0004]

However, these water-soluble processing oils have a problem in terms of processability and, in some cases, inferior defoaming properties. Therefore, only in a limited form. At present, it cannot be used. The present invention provides a water-soluble processing oil which is excellent not only in workability but also in rust prevention, antibacterial properties and defoaming properties.

[0005]

The present invention provides a compound represented by the following general formula (1):

[0006]

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(Wherein, R is a hydrogen atom, a lower alkyl group, and — (CH 2) n COOH (n is an integer of 0 to 3; m is an integer of 0 to 3). Provided is a water-soluble processing oil containing at least one selected from the group consisting of a reaction product of adamantanecarboxylic acid and an alkanolamine and a salt thereof.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION The general formula (1) shown in the present invention is an adamantanecarboxylic acid having one or two carboxyl groups in an adamantane skeleton.

R in the general formula (1) represents any one of a hydrogen atom, a lower alkyl group and — (CH 2) n COOH;
n represents an integer of 0 to 3. m represents an integer of 0 to 3.

Examples thereof include 1-adamantane acetic acid, 1-adamantane carboxylic acid, 1,3-adamantane diacetate, 1,3-adamantane dicarboxylic acid, and 3-methyl-1-adamantane acetic acid.

The alkanolamine used in the present invention is an alkanolamine having 1 to 3 aliphatic groups having 1 to 4 carbon atoms and having at least one hydroxyl group. For example, monoethanolamine, monoisopropanolamine, monoisobutanolamine, N-methylethanolamine, N-ethylethanolamine,
N-butylethanolamine, diethanolamine, diisopropanolamine, diisobutanolamine, N
-Methyldiethanolamine, N-ethyldiethanolamine, N-butylethanolamine, triethanolamine, triisopropanolamine, triisobutanolamine, cyclohexylaminoethanol, N, N
-Dibutylethanolamine, 1-amino-2propanol and the like. Preferred are mono (di and tri) ethanolamine and mono (di and tri) isopropanolamine.

The reactant of adamantanecarboxylic acid and alkanolamine referred to in the present invention is an amide compound obtained by reacting the carboxyl group of adamantanecarboxylic acid with the amino group of alkanolamine, and the carboxyl group of adamantanecarboxylic acid and the hydroxyl of alkanolamine. An ester compound by reaction with a group. The amide or ester according to the present invention may be any of a complete amide or a complete ester, a partial amide or a partial ester.

In use, an amide compound or an ester compound may be used alone, or a mixture thereof.

The esterified product used in the present invention is obtained by dehydration-condensation of an alkanolamine hydrochloride or sulfate and a carboxylic acid by heating and refluxing in a solvent without a catalyst or using an acidic catalyst (such as paratoluenesulfonic acid). Can be obtained by 100 to 2 in an inert gas atmosphere without solvent.
It can also be obtained by heating and dehydrating to 00 ° C. When the alkanolamine is a tertiary amine, an ester can be obtained without salting the alkanolamine.

When the alkanolamine is a primary or secondary amine, the amide compound is prepared in a stream of adamantanecarboxylic acid and an inert gas or in a solvent such as benzene without a catalyst at 100 to 200 ° C. And a method of removing generated water.

As another method for synthesizing a small amount of by-products, an acid chloride of adamantacarboxylic acid and an alkanolamine are generally synthesized in a solvent such as methyl dichloride, chloroform or ether in the presence of a tertiary amine such as triethylamine. It can also be obtained by reacting at a low temperature around 0 ° C.

The salt according to the present invention means, in the case of partial amides and partial esters, neutralization of carboxyl groups still remaining in the reaction product, for example, alkali metals, alkylamines, alkanolamines, and ammonium salts. Are exemplified. Preferably, it is a salt of an alkali metal and ethanolamine.

The compounding amount of the compound of the present invention as the water-soluble processing oil according to the present invention is not particularly limited.
The compounding amount in the oil solution stock solution is usually 5 to 80% by weight, and this is diluted 5 to 100 times with water before use. If the concentration in the diluted use solution is 0.1% by weight or less, the rust resistance is deteriorated, which is not preferable.

The water-soluble processing oil of the present invention may optionally contain conventional additives such as mineral oil, animal and vegetable oils, fatty acids, fatty acid esters, extreme pressure additives, surfactants and preservatives.

[0020]

EXAMPLES The present invention will be described below in detail with reference to examples, but the present invention is not limited to these examples.

[Synthesis of a reaction product of adamantanecarboxylic acid and alkanolamine] Table 1 shows adamantanecarboxylic acid and alkanol as starting materials of the reaction product of the present invention (compounds Nos. 1 to 17) used in Examples. The amine and its reaction molar ratio are shown.

[0022]

[Table 1]

[Compound No. Synthesis of Compound No. 1 of Example used in the present invention. Compound (1) is prepared by reacting 1 mol of 1-adamantacarboxylic acid with thionyl chloride at 80 to 100 ° C. to synthesize α-chlorocarboxylic acid according to a conventional method. And 1 molar weight of triethanolamine in a chloroform solvent at a temperature of 0 ° C. or lower using triethylamine as a catalyst, and then removing by-product hydrogen chloride by washing with pure water, dehydrating, and then distilling off chloroform. I got it.

[Compound NO. Synthesis of Compound Nos. 2 to 17] Compounds Nos. 2 to 17 were also synthesized, except that the starting materials and the reaction molar ratio were changed. Compound 1 was obtained in the same manner as in Example 1.

Examples 1 to 19 Compounds N shown in Table 1
o. A reaction solution of 1 to 17 adamantacarboxylic acid and alkanolamine, and a 1% by weight aqueous solution of a triethanolamine salt and a sodium salt of the reaction product were used as test solutions, and the test solution described below was used. The coefficient of friction, pressure resistance, rust prevention, antibacterial and defoaming properties were measured. The results are shown in Tables 2 and 3.

(1) Method of Measuring Friction Coefficient The friction coefficient was measured with a Soda pendulum type friction tester (25 ° C.).

(2) Method of Measuring Pressure Resistance Measured with a Soda four-ball lubrication tester (200 rpm, sequential load method).

(3) Method of Measuring Rust Prevention After dry cutting chips of casting (FC250) were immersed in a test solution for 10 minutes, the test solution was cut, transferred to a petri dish, and left in a constant temperature chamber at 30 ° C. for 3 days. And the rusting state was observed.

Judgment criteria-: no rusting +: rusting

(4) Method of Measuring Antibacterial Activity On a plate-shaped normal agar medium having a diameter of 10 cm and a capacity of 10 ml,
Septic liquid (liquid containing cutting oil with a bacterial count of at least 10 5 / ml)
After 1 microliter was applied to the entire surface and air-dried for 10 minutes, 1 ml of a test solution was dropped on the center of the agar medium, and cultured in a thermostat at 30 ° C. for 3 days, and the propagation state of the bacteria was observed. The results were evaluated in the following four stages by comparing the breeding state of the bacteria under the test droplet with the peripheral part.

0: no breeding 1: breeding is small compared to the surrounding area 2: breeding to some extent but less than the surrounding area 3: breeding about the same as the surrounding area

(5) Measuring method of defoaming property 50 ml of the sample solution was placed in a 100 ml measuring cylinder with a stopper, and after sealing, the measuring cylinder was shaken up and down 10 times at a liquid temperature of 30 ° C., and then allowed to stand still. Immediately after, 30 seconds and 60 seconds later, the volume of the foam was measured.

[0033]

[Table 2]

[0034]

[Table 3]

[Comparative Examples 1 to 8] Comparative Example N shown in Table 4
o. A 1% by weight aqueous solution of the components 1 to 8 was prepared and tested in the same manner as in the examples. The results are shown in Tables 4 and 5.

[0036]

[Table 4]

[0037]

[Table 5]

Examples 20 to 22 and Comparative Examples 9-1
1] Example No. 1 shown in Table 6. 20 to 22 and Comparative Example Nos.
A 1% by weight aqueous solution of the components 9 to 11 was prepared, and the following tapping test was performed to evaluate the cutting performance. Table 6 shows the results.

Tapping test conditions and evaluation method Processing machine: Vertical NC milling machine (manufactured by Enshu) Working tool: M12 × 1.25 Hand tap (manufactured by HSS, Yamawa) Cutting conditions: cutting speed 6 m / min, feed 200 mm / min , Depth 20mm, non-penetration, pilot hole diameter 10.7mm Work material: S45C Evaluation method: The screw hole after processing is inspected with a screw limit gauge (Kroda GP-IPM12P1.25), and there is no abnormality in the screw hole. Processing was continued with one tool until it was seen, and the number of screw holes that could be processed normally with one tool was measured as tool life.

[0040]

[Table 6]

[0041]

As described above, the salt of the amide compound of the present invention has excellent processing performance and excellent defoaming properties, rust prevention properties and antibacterial properties. Therefore, the water-soluble processing oil of the present invention is not only excellent in processing performance, but also excellent in defoaming properties, rust prevention and antibacterial properties, and has good workability, as compared with conventional oils, and furthermore, it is susceptible to decay and rust. Since there is little deterioration in performance and workability, it can be used stably for a long period of time.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI C10M 133: 08) C10N 40:20 40:22 40:24

Claims (1)

[Claims] 1. General formula (1): (Wherein R represents a hydrogen atom, a lower alkyl group, and-(C
H2) nCOOH (n is an integer of 0 to 3. m is 0
A water-soluble processing oil containing at least one selected from the group consisting of a reaction product of an adamantanecarboxylic acid and an alkanolamine represented by the following formula: and a salt thereof.