JP2003238978A - Metal forming fluid - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a polyether based metal forming fluid which excels in compatibility with a hydrocarbon based lubricating oil, lubricity, viscosity index properties and the like. <P>SOLUTION: The metal forming fluid is composed of (E) a polyether which is represented by the formula: R<SP>1</SP>[-ä(OCH<SB>2</SB>CH<SB>2</SB>CH<SB>2</SB>CH<SB>2</SB>)<SB>m</SB>(OA)<SB>n</SB>}-OH]<SB>p</SB>(wherein R<SP>1</SP>is a residue obtained by removing all hydroxy groups from a 1-24C compound having 1-6 hydroxy groups; A is a 2-4C alkylene group except a 1,4-butylene group; m and n are ≥1 integers which render the weight average molecular weight of polyether (E) 500-30,000; and p is an integer of 1-6) and has an HLB (hydrophile-lipophile balance) of ≤6.0 and, simultaneously, a weight average molecular weight of 500-30,000. <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a polyether metal working oil. More specifically, it relates to a polyether metal working oil having excellent compatibility with a hydrocarbon base oil and lubricity.

[0002]

Lubricating properties are required for cutting oil, grinding oil, polishing oil, rolling oil, drawing oil, press oil, forging oil, and metal working oil used for working such as polishing and cutting of silicon wafers. Conventionally, metal-working oils such as emulsion-based cutting oils and non-water-based cutting oils that use mineral oil as a base oil are fatty acid esters,
It has been made to improve lubricity by adding an oiliness improver such as a fatty acid or an extreme pressure agent containing an element such as sulfur, chlorine, or the like. However, chlorine-based extreme pressure agents are difficult to use due to environmental problems such as ozone layer depletion, and neighboring extreme pressure agents due to eutrophication due to wastewater. Furthermore, polyethers having good lubricity have poor compatibility with hydrocarbon base oils such as mineral oils, so that it is difficult to make the product appearance uniform.

[0003]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a polyether-based metal working oil which is excellent in compatibility with a hydrocarbon-based lubricating oil, lubricity, viscosity index property and the like.

[0004]

The present inventors have arrived at the present invention as a result of extensive studies in view of the above problems. That is, the present invention is represented by the following general formula (1), has an HLB of 6.0 or less, and a weight average molecular weight of 500 to 30,000.
It is a metalworking oil consisting of a polyether (E) which is 0. R ¹ [-{(OCH ₂ CH ₂ CH ₂ CH ₂ ) _m (OA) _n } -OH] _p (1) [wherein R ¹ is a compound having 1 to 6 hydroxyl groups having 1 to 24 carbon atoms] Residue excluding all hydroxyl groups, A is 1,4-
An alkylene group having 2 to 4 carbon atoms excluding a butylene group,
m and n have a weight average molecular weight of (E) of 500 to 30,0.
1 is an integer of 1 or more, and p is an integer of 1 to 6. ]

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION R ¹ in the above general formula (1) is a residue obtained by removing all hydroxyl groups from a compound having 1 to 6 hydroxyl groups having 1 to 24 carbon atoms, and is linear, branched or cyclic. 1 to 6 valent alcohol residue, 1 to 6 valent phenol residue, and 1 to 6 valent araliphatic alcohol residue. That is, R ¹ is a residue obtained by removing all OH from R ¹ [OH] p. Specifically, the monohydric alcohol [R ¹ OH] forming a residue obtained by removing a hydroxyl group from a monohydric alcohol has a linear or branched carbon number of 1 to 1
18 saturated aliphatic monools (methanol, ethanol, n- and i-propanol, butanol, pentanol, hexanol, heptanol, octanol,
Nonyl alcohol, decyl alcohol, undecyl alcohol, dodecyl alcohol, tridecyl alcohol,
Tetradecyl alcohol, pentadecyl alcohol, heptadecyl alcohol, octadecyl alcohol, nonadecyl alcohol, eicosyl alcohol, heneicosyl alcohol, docosyl alcohol, tricosyl alcohol, tetracosyl alcohol, etc.); cis- or trans- Saturated aliphatic hydrocarbon group (alcohol having an alkenyl group or an alkynyl group, for example,
Ethenyl alcohol, 1-, 2- and iso-propenyl alcohol, butenyl alcohol, pentynyl alcohol, hexenyl alcohol, heptenyl alcohol,
Nonenyl alcohol, decenyl alcohol, undecenyl alcohol, dodecenyl alcohol, tridecenyl alcohol, tetradecenyl alcohol, pentadecenyl alcohol, hexadecenyl alcohol, heptadecenyl alcohol, octa Decenyl alcohol, nonadecenyl alcohol, eicosenyl alcohol, heneicosenyl alcohol, docosenyl alcohol, tricosenyl alcohol, tetracosenyl alcohol, etc.); and C4-24 alicyclic mono All (cyclopentanol,
Cyclohexanol etc.) and the like.

The dihydric alcohol [R ¹ (OH) ₂ ] forming a dihydric alcohol residue is an aliphatic diol having 2 to 24 carbon atoms (for example, ethylene glycol, propylene glycol, 1,3-, 1,4- and 1,2-butanediol, neopentyl glycol, 1,6-hexanediol, 1,2- and 1,8-octanediol, isobutylene glycol, 3-methyl-1,5-pentanediol, 2 , 2,4-Trimethyl-1,3-pentanediol, 2,2-dimethyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, and 2,5-dimethylhexane- Alkylene glycol such as 2,5-diol); alicyclic diol having 4 to 18 carbon atoms (for example, 1,4-cyclohexanediol,
Cycloalkylene glycols such as 1,4-cyclohexanedimethanol); hydrogenated bisphenols (eg hydrogenated bisphenol A, hydrogenated bisphenol F); and heterocyclic diols (eg 1,4,3,6-sorbide), etc. Is mentioned.

3 to form a residue of a trivalent to hexavalent alcohol
To hexavalent alcohol as the _{^{[R 1 (OH) 3 ~}} 6], 3 monohydric alcohol 3 to 24 carbon atoms (aliphatic triols, such as glycerin, 1,2,3-butanetriol, 1,
2,3-pentanetriol, 2-methyl-1,2,3
-Propanetriol, 2-methyl-2,3,4-butanetriol, 2-ethyl-1,2,3-butanetriol, 2,3,4-pentanetriol, 2,3,4-
Hexanetriol, 4-propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3,4-pentanetriol, pentamethylglycerin, 1,2,4
-Butanetriol, 1,2,4-pentanetriol, alkanetriol such as trimethylolethane and trimethylolpropane), C4 to C4 polyhydric alcohols (aliphatic polyols such as pentaerythritol, Sorbitol, mannitol, 1,5
-, 3,6- and 1,4-sorbitan, alkane polyols such as diglycerin, and intramolecular or intermolecular dehydration products thereof, and sugars such as sucrose, glucose, mannose, fructose, and methylglucoside and derivatives thereof)
Is mentioned.

The phenol [R ¹ OH] forming a residue obtained by removing a hydroxyl group from a monohydric phenol is a monohydric phenol having 6 to 24 carbon atoms, for example, phenol or alkylphenol (o, m or p). -Methylphenol,
m, p-dimethylphenol, 2,6-dimethylphenol, o, m or p-ethylphenol, pn-butylphenol, p-octylphenol, p-nonylphenol, etc.), monostyrylphenol, monobenzylphenol and the like. . Examples of the phenol [R ¹ (OH) ₂ ] forming a residue of a divalent to hexavalent phenol include a divalent to hexavalent phenol having 6 to 24 carbon atoms. The above-mentioned phenols include monocyclic polyhydric phenols.
[For example, dihydric phenol (catechol, resorcin,
Hydroquinone etc.), trioxybenzene, tetraoxybenzene, hexaoxybenzene etc.], bisphenols (eg bisphenol A, bisphenol F etc.)
Etc.

[0009] 1-6 divalent araliphatic alcohols to form the residue of araliphatic alcohols _{^{[R 1 (OH) 1 ~}} 6], aralkyl alcohol having 7 to 24 carbon atoms (benzyl alcohol, phenethyl alcohol, etc. ), Carbon number 8 ~
And 24 substituted aralkyl alcohols (o, m or p-methylbenzyl alcohol, pn-butylphenethyl alcohol, etc.) and the like.

Of these, preferred are those having 1 to 20 carbon atoms.
Is a residue of a linear, branched or cyclic 1 to 6 valent alcohol, and more preferably a residue of a linear or branched 1 to 3 valent aliphatic or alicyclic alcohol having 2 to 18 carbon atoms. It is a residue of a straight-chain or branched monovalent saturated or unsaturated aliphatic alcohol having 4 to 18 carbon atoms, in terms of good compatibility with hydrocarbons. 24 carbon atoms
If it exceeds, the viscosity index becomes worse.

A in the general formula (1) is one or more alkylene groups having 2 to 4 carbon atoms excluding 1,4 butylene group. Examples of the alkylene group having 2 to 4 carbon atoms include ethylene group, 1,2- and 1,3-propylene group,
1,2- and 2,3-butylene groups and isobutylene groups are mentioned. You may use these 1 type (s) or 2 or more types. Of these, ethylene group, 1,2-propylene group and 1,2-butylene group are preferable, and branched alkylene groups such as 1,2-propylene group and 1,2-butylene group are particularly preferable. When the branched alkylene group is present in A, the compatibility with hydrocarbon is improved.

M and n in the general formula (1) are such that the weight average molecular weight of the polyether (E) is 500 to 30,000.
Is an integer greater than or equal to 1. Preferably, the ratio of m to n (m
/ N) is 5/95 to 45/55. That is (OCH ₂
CH ₂ CH ₂ CH ₂ ) content is (OCH ₂ CH ₂ CH ₂ C
It is preferably 5 to 45 mol% of the total content of H ₂ ) and (OA). Further, it is preferable that (E) has a random bonding portion of an oxytetramethylene group (OCH ₂ CH ₂ CH ₂ CH ₂ group) and another oxyalkylene group (OA group) from the viewpoint of excellent flow characteristics at low temperatures. . (E)
It is more preferable that 80% by mass or more of the oxytetramethylene groups constituting the above are present in the random bonding portion.

In the general formula (1), p is an integer of 1 to 6, preferably 1 to 3, and 1 is particularly preferable because it has good compatibility with hydrocarbons. If k exceeds 6, the lubricating performance will deteriorate.

The polyether (E) represented by the general formula (1) can be produced by using a compound represented by R ¹ (OH) _p , which has 1 to 6 carbon atoms and 1 to 6 hydroxyl groups, and a catalyst. In the presence of, preferably at a temperature of 30 to 120 ° C., preferably at a pressure of 0 to 0.6 MPa, tetrahydrofuran (hereinafter TH
F) and alkylene oxide having 2 to 4 carbon atoms (hereinafter referred to as AO) can be added at random or in blocks to produce.

Regarding the above-mentioned catalyst, conventionally known catalysts can be used, but the preferable range is different for THF addition and AO addition. Examples of the catalyst used in the case of homo-addition of THF or addition copolymerization with AO include BF ₃ , BCl ₃ and AlC.
Lewis acids such as l ₃ , FeCl ₃ , SnCl ₃ and their complexes [eg, BF ₃ ether complex, BF ₃ tetrahydrofuran complex (BF ₃ · THF)]; H ₂ SO ₄ , HClO ₄
Protic acids such as KClO ₄ , NaClO _{4 and} other alkali metal perchlorates; Ca (ClO ₄ ) ₂ , Mg (Cl
Perchlorates of alkaline earth metals such as O ₄ ) ₂ ; Al (Cl
Examples thereof include perchlorates of metals other than the above, such as O ₄ ) ₃ . Of these, BF ₃ ether complex and BF ₃ tetrahydrofuran complex (BF ₃ · THF) are preferable. The catalyst for the case of adding AO alone may be a commonly used known catalyst, and in addition to the above catalysts, an alkali catalyst such as hydroxide [KOH, NaOH, CsOH,
Hydroxides of alkali metals or alkaline earth metals such as Ca (OH) ₂ ]; oxides (K 2 O 2, CaO, Ba
Examples thereof include oxides of alkali metals or alkaline earth metals such as O); alkali metals (Na, K, etc.) and hydrides thereof (NaH, KH, etc.); amines such as triethylamine, trimethylamine and the like. Of these, KOH, NaOH, CsOH, BF ₃ ether complex and BF ₃ tetrahydrofuran complex (BF ₃ · THF) are preferable. As AO to be added, A is an alkylene group having 2 to 4 carbon atoms in the general formula (1), and examples thereof include ethylene oxide (hereinafter referred to as EO), propylene oxide (hereinafter referred to as PO), and 1,2-butylene. Oxide,
2,3-butylene oxide, isobutylene oxide and the like can be mentioned. Of these, preferred are EO, PO,
1,2-butylene oxide, particularly preferably PO
Is. These may be used in combination, and the polymerization method may be random or block. The number of moles of THF added (m) is 3
The number of added moles (n) of -100 to AO is preferably 5 to 150, more preferably 4 to 20 for m and 6 to 50 for n.

The HLB value of the polyether (E) thus obtained is usually 6.0 or less, preferably 5.0 or less, more preferably 2 to 4.
If the HLB value exceeds 6.0, the compatibility of the polyether (E) with hydrocarbons such as mineral oil and polybutene deteriorates.
The HLB value is a value calculated by the Oda formula based on the organic conceptual diagram.
[Showa 51, Engineering Book Co., Ltd.]. Regarding the organic value and the inorganic value for deriving the HLB value, the inorganic group table described in "Organic Conceptual Diagram -Basics and Applications-" [Sankyo Publishing Co., Ltd. (1984)] (Showa 49, Fujita et al. It can be calculated using the reported value).

The weight average molecular weight (Mw) of (E) is 50.
0-30,000, preferably 700-10,0
00, more preferably 800 to 5,000. 5
If it is less than 00, the lubricity of the metalworking oil is reduced to 30,000
If it exceeds 0, the kinematic viscosity of the metal working oil becomes too high. The weight average molecular weight is measured by gel permeation chromatography (GPC) (column: TSKgel G2
000, G3000, G4000HXL, solvent: TH
F). The same applies below.

The polyether metal working oil of the present invention is composed of polyether (E), but the polyether (E) may be a mixture of those having different compositions, molecular weights, etc., and if necessary, Hydrocarbon oil may be added. As hydrocarbon-based oils, solvent refined oils, paraffin-based mineral oils, naphthene-based mineral oils, alkyls (having 10 to 100 carbon atoms)
Examples thereof include benzene, alkyl (having 10 to 100 carbon atoms) naphthalene, poly-α-olefin (having 2 to 50 carbon atoms), polybutene (weight average molecular weight 200 to 4000), polyisobutene (weight average molecular weight 200 to 4000) and the like. Preferred are solvent refined oils, paraffinic mineral oils, naphthenic mineral oils and polybutenes. Kinematic viscosity of these hydrocarbon oils (measured according to JIS K 2283.)
Is preferably 1-3520 mm2 / s at 40 ° C. The mixing ratio of the polyether-based metal working oil and the hydrocarbon-based oil may be arbitrary, but the mass ratio of the polyether-based metal-working oil / hydrocarbon-based oil is preferably 5/95 to 95/5,
It is more preferably 10/90 to 90/10, and particularly preferably 20/80 to 80/20. Mixed oils can exhibit the characteristics of both polyethers and hydrocarbons. In addition, if necessary, another polyether [oxytetramethylene group (OCH ₂ CH ₂ in the general formula (1)
A polyether containing no CH ₂ CH ₂ group) and the like] can be blended. Its content is less than 90% by weight.

Further, if necessary, it is selected from a detergent dispersant, an antioxidant, an oiliness agent, an extreme pressure agent, a metal deactivator, a rust preventive, an antifoaming agent, a viscosity index improver and a pour point depressant. It is preferable that the metalworking oil composition contains one or more additives described above.

Examples of the detergent dispersant include neutral or basic sulfonates (for example, petroleum sulfonic acid such as calcium petroleum sulfonate (normal salt) and basic barium sulfonate) and alkyl (C5-C36) substituted aromatic sulfonic acid. A positive or basic metal salt, etc.]; a neutral or basic phenate [for example, alkyl (C1-C36) phenol, alkyl (C1-C36) phenol sulfide, alkyl (C1-C36) phenol aldehyde Condensation product, positive or basic metal salt, etc.]; Neutral or basic phosphonate, thiophosphonate; Alkyl (C1-C36) substituted salicylate; Alkyl (C5
To 36) methacrylate or a monomer containing the methacrylate and a polar group (amine, amide, imide, hydroxyl, carboxyl, nitrile, etc.) (molar ratio 99/1 to
10/90) copolymers [for example, alkyl (C1-C1
36) Methacrylate-vinylpyrrolidinone copolymer (weight average molecular weight: 1,000 to 100,000), alkyl (C1-C36) methacrylate-diethylaminoethyl methacrylate copolymer (weight average molecular weight:
1,000 to 100,000), alkyl (C1-C1)
36) Methacrylate-polyethylene glycol-methacrylate copolymer (weight average molecular weight: 1,000 to 1)
Etc.]; N-substituted alkenyl (having 5 to 5 carbon atoms)
36) Succinimide (for example, N-tetraethylenepentamine polyisobutenyl succinimide); High molecular weight amide [for example, polystearamide (weight average molecular weight:
1,000 to 100,000), etc.] and the like. The amount of detergent dispersant used is preferably 15% by weight or less, based on the metalworking oil. Hereinafter, the amount of the additive is a value based on the metal working oil.

As the antioxidant, a phenolic antioxidant [eg, 2,4-dimethyl-6-tert-butylphenol, 4,4-butylidenebis (6-tert-butylmethacresol)]; an amine antioxidant ( Examples thereof include monooctyldiphenylamine, dioctyldiphenylamine, etc .; dialkyl (C1-C36) zinc dithiophosphate; diallyl (C2-C36) zinc dithiophosphate; organic sulfides; organic selenides and the like. The amount of the antioxidant used is preferably 2% by mass or less.

As the oiliness agent, fats and oils such as lard oil; long-chain fatty acids having 8 to 36 carbon atoms (octylic acid, lauric acid,
(Palmitic acid, oleic acid, stearic acid, etc.) and these fatty acids and monohydric and polyhydric alcohol esters; higher alcohols having 8 to 36 carbon atoms (octyl alcohol, lauryl alcohol, palmityl alcohol, oleyl alcohol, stearyl alcohol, etc.) and The ester is mentioned. The amount of the oily agent used is preferably 15% by mass or less.

As extreme pressure agents, lead soap (lead naphthenate, etc.); sulfur compounds (sulfurized fatty acid ester, sulfurized spum oil, sulfurized terpenes, dibenzyl disulphide, etc.);
Chlorine compounds (chlorinated paraffin, chloronaphthazanate, etc.); Phosphorus compounds (tricresyl phosphate, tributyl phosphate, tricresyl phosphite, n-
Butyl di-n-octyl phosphinate, di-n-butyl dihexyl phosphonate, di-n-butyl phenyl phosphonate, dibutyl phosphoroamidate, amine dibutyl phosphate and the like). The amount of the extreme pressure agent used is preferably 10% by mass or less.

Examples of the metal deactivator include benzotriazole, mercaptobenzothiazole, N, N'-disalicylidene-1,2-diaminopropane and alizarin. The amount of the metal deactivator used is preferably 2% by mass or less.

Examples of the rust preventive agent include aliphatic carboxylic acids having 6 to 36 carbon atoms (caprylic acid, lauric acid, nonanoic acid,
Decanoic acid, oleic acid, etc.) and alkali metal salts, amine salts; alkenyl succinic acids having 6 to 36 carbon atoms (octenyl succinic acid, dodecenyl succinic acid, pentadecenyl succinic acid, octadecenyl succinic acid, etc.) and alkali metal salts ,
Amine salt; dibasic acid having 6 to 24 carbon atoms (azelaic acid, sebacic acid dodecanedioic acid, dimer acid, etc.) and alkali metal salt, amine salt; aromatic carboxylic acid (benzoic acid,
(p-tert butylbenzoic acid, nitrobenzoic acid, etc.) and alkali metal salts, amine salts; (alkyl phosphate ester salts having 8 to 18 carbon atoms; (cyclo) alkylamine (1 carbon atom)
To 36) or a heterocyclic amine (C4 to C36) alkylene oxide (C2 to C4) (1 to 10 mol) adduct (eg, cyclohexylamine EO2 mol adduct, cyclohexylamine PO2 mol adduct, morpholine EO).
1 mol adduct, morpholine PO 1 mol adduct, etc.); Petroleum sulfonate; Alkyl (C1-C36) naphthalene sulfonate and sorbitan ester (eg, sorbitan laurate, sorbitan stearate, etc.); Examples thereof include alkenyl succinic acid, amides of dibasic acid with amine and ammonia, and the like. The amount of the rust preventive used is preferably 5% by mass or less.

Examples of the defoaming agent include polyorganosiloxane (eg polydimethylsiloxane).
The amount of defoaming agent used is preferably 0.1% by mass or less.

Examples of the viscosity index improver include polyalkyl (C1-18) methacrylate and polyalkyl (C1-18) acrylate having a weight average molecular weight of 20,000 to 1,500,000; Mw of 5,000. ~ 300,
000 polyisobutylene; Mw 10,000 to 30
10,000 polyalkyl (8 to 12 carbon atoms) styrene; olefin (2 to 12 carbon atoms) copolymer [eg ethylene-propylene (molar ratio 5/95 to 95/5) copolymer, styrene-isoprene ( Molar ratio 5 / 95-95 /
5) Hydrogenated products of copolymers] and the like. The amount of the viscosity index improver used is preferably 15% by mass or less.

As the pour point depressant, polyalkyl (C6-24) methacrylate; naphthalene-chlorinated paraffin condensation product; ethylene-vinyl acetate (molar ratio 5 / 95-95 / 5) copolymer; polyacrylamide Vinyl carboxylate (C1-C36) -dialkyl (C1-C36) fumarate (molar ratio 5/95
To 95/5) copolymers and the like. The weight average molecular weight of each of these pour point depressants is 1,000 to 10.
It is 10,000. The amount of the pour point depressant used is preferably 1% by mass or less.

The total content of the above additives is preferably 20% by mass or less in the metal working oil. Further, these additives may be used in combination of two or more kinds.

If necessary, an emulsifying agent such as a surfactant may be added to these, and the mixture may be diluted 10 to 100 times with water before use. The amount of the emulsifier added is the amount added to the base oil (metalworking oil that is a polyether metalworking oil or a mixture of polyether metalworking oil / hydrocarbon oil) unless otherwise specified, and% is the mass. Represents%.

Examples of emulsifiers include Na and K salts of sulfonic acids (alkylbenzene sulfonic acid, petroleum sulfonic acid, alkylnaphthalene sulfonic acid, etc.), and fatty acids (lauric acid, palmitic acid, myristic acid, oleic acid, castor oil fatty acid, etc.). Na, K salts and PEG esters obtained by esterifying these fatty acids with polyethylene glycol such as monoethanolamine, diethanolamine, triethanolamine and the like, and alcohols having 8 to 24 carbon atoms (octyl alcohol, decyl alcohol, dodecyl alcohol, tridecyl). Alcohol, tetradecyl alcohol, hexadecyl alcohol, oleyl alcohol,
Stearyl alcohol, etc.), a nonionic activator obtained by adding ethylene oxide, a sorbitan fatty acid ester, and a nonionic activator obtained by adding these ethylene oxides. The amount of emulsifier used is usually 30% or less.

The polyether metal working oil of the present invention can be used for cutting oil, rolling oil, grinding oil, polishing oil, forging oil, pressing oil, drawing oil, release oil, cutting of silicon wafer and the like.

[0033]

The present invention will be described in detail with reference to the following examples, but the present invention is not limited thereto.

The test method is as follows. (1) Kinematic viscosity and viscosity index Measured according to JIS K 2283. (2) Compatible spindle oil [SYC spindle oil manufactured by Cosmo Oil Co., Ltd.
The same applies hereinafter. ] Was evaluated by measuring the critical temperature. The critical temperature was 0 ° C to 85 ° C, and the metalworking oils of Examples and Comparative Examples were mixed with the above hydrocarbons in a test tube at a mass ratio of 30/70, and the separation temperature was measured. (3) Evaluation was performed by observing the friction coefficient at the point contact between the steel ball and the flat steel disk and the wear scar diameter on the steel ball using a lubricative vibration friction wear tester (SRV tester). <Lubricity test conditions> Vibration frequency: 50Hz Vibration width: 2mm Load: 200N, 300N, 500N Time: 10 minutes Temperature: 30 ° C Friction coefficient: Time 10 minutes Average value Wear diameter (mm): 10mm Steel ball (SUJ- 2) Oil film breakage: Changes in the friction coefficient (μ) were observed. ◯: Stable, Δ: Slightly fluctuated, × fluctuated. Unless otherwise specified, the parts in the text represent parts by mass.

Example 1 Isotridecanol [trade name “Tridecanol” manufactured by Kyowa Hakko Kogyo Co., Ltd. was added to a glass autoclave. The same applies hereinafter. ] 200 parts (1.0 mol) and tetrahydrofuran (THF) 468 parts (6.5 mol) and BF3.THF
7.9 parts of was added, and 580 parts of PO (10.0 mol) was added dropwise from a pressure-resistant dropping funnel at 35 to 50 ° C. over 10 hours. Then, it reacted at 50 degreeC for 5 hours, and cooled. Further, after adding 4.8 parts of 48% NaOH aqueous solution, an adsorption treatment agent [Kyowaad 600 and Kyowaad 1000 manufactured by Kyowa Chemical Industry Co., Ltd. The same applies hereinafter. ], Filtered, and dehydrated under reduced pressure at 30 mmHg or less to obtain 1120 parts (a1) of 6.5 mol of isotridecanol in THF / 10.0 mol of PO random adduct.

Example 2 A glass autoclave was charged with 130 parts (1.0 mol) of 2-ethylhexyl alcohol, 504 parts (7.0 mol) of THF and 7.9 parts of BF3.THF, and 580 parts of PO from a pressure-resistant dropping funnel ( 10.0 mol) 35-50
It was added dropwise at 10 ° C. over 10 hours. Then, it reacted at 50 degreeC for 5 hours, and cooled. Further, add 48% NaOH aqueous solution to 4.
After adding 8 parts, treated with an adsorption treatment agent, filtered,
After dehydration under reduced pressure at mHg or less, 1100 parts (a2) of 2-ethylhexyl alcohol in a THF 7.0 mol / PO 10.0 mol random adduct was obtained.

Example 3 In a glass autoclave, 200 parts (1.0 mol) of isotridecanol, 504 parts (7.0 mol) of THF and B were added.
7.9 parts of F3.THF was charged, and 580 parts of PO (10.0 mol) was dropped from a pressure-resistant dropping funnel at 35 to 50 ° C. over 10 hours. Then, it was aged at 50 ° C. for 5 hours and cooled. Further, after adding 4.8 parts of 48% NaOH aqueous solution, it was treated with an adsorption treatment agent, filtered, and dehydrated under reduced pressure at 30 mmHg or less. THF of the obtained isotridecanol
7.0 mol / PO 10.0 mol Random adduct 1220
Of the parts, 642 parts (0.5 mol) and 2.27 parts of KOH were charged in a glass autoclave, and 116 parts (2.0 mol) of PO was added dropwise from the pressure dropping funnel at 105 ° C. over 5 hours. Then, it was made to react at 130 degreeC for 5 hours, and was cooled. Further treated with adsorption treatment agent, filtered, 30mmH
After dehydration under reduced pressure below g, THF of isotridecanol 7.
689 parts (a3) of 0 mol / PO10.0 mol random PO4.0 mol block adduct were obtained.

Example 4 30 parts of (a1) and 70 parts of spindle oil were mixed,
100 parts (a4) of a mixture of (a1) and spindle oil was obtained.

Example 5 30 parts of (a1) and 70 parts of polybutene [Nisseki Polybutene LV-25E manufactured by Nippon Petrochemical Co., Ltd.] were mixed, and (a1)
100 parts (a5) of a mixture of 1) and polybutene were obtained.

Comparative Example 1 200 parts (1.0 mol) of isotridecanol and 3.3 parts of KOH were charged into a glass autoclave and PO1102 parts (19.0 mol) were added from a pressure-resistant dropping funnel at 105 ° C. for 33 hours. Dropped. Then, it was made to react at 130 degreeC for 10 hours, and was cooled. Further, it was treated with an adsorption treatment agent, filtered, and dehydrated under reduced pressure at 30 mmHg or less to obtain 1184 parts (b1) of a PO19.0 mol adduct of isotridecanol.

Comparative Example 2 2,2,4-trimethyl- was added to a glass autoclave.
146 parts (1.0 mol) of 1,3-pentanediol and K
3.3 parts of OH was charged, and from the pressure-resistant dropping funnel to PO115
4 parts (19.9 mol) was added dropwise at 105 ° C. over 33 hours. Then, it was made to react at 130 degreeC for 10 hours, and was cooled. Further, it is treated with an adsorption treatment agent, filtered, and 30 mmH
2,2,4-trimethyl-1,3 after dehydration under reduced pressure below g
-Pentanediol PO 19.9 mol adduct 1230
Part (b2) was obtained.

Comparative Example 3 74 parts of n-butanol (1.
0 mol) and 1.1 parts of KOH were charged, and a mixture of 222.4 parts of EO (5.1 mol) and 226.2 parts of PO (3.9 mol) was added dropwise from the pressure-resistant dropping funnel at 110 ° C. over 15 hours. Then, it was made to react at 130 degreeC for 10 hours, and was cooled. After cooling, treat with adsorption treatment agent, filter, 30mmH
After dehydration under reduced pressure below g, 475 parts (b3) of n-butanol EO5.1 mol / PO3.9 mol random adduct were obtained.

Comparative Example 4 4.8 parts of EO224.
Using 915.2 parts (20.8 mol) instead of 4 parts, P
926.4 parts of O instead of 916.4 parts (15.8 mol)
In the same manner as in Comparative Example 3 except that was used, 1800 parts (b4) of n-butanol EO20.8 mol / PO15.8 mol random adduct was obtained.

COMPARATIVE EXAMPLE 5 In Comparative Example 3, 3.8 parts were used in place of 1.1 parts of KOH, and 1281.8 parts (2 parts) were replaced in place of EO226.2 parts.
2.1 mol) was used, EO was not used, and the mixture was added dropwise at a temperature of 105 ° C. for 10 hours, and then reacted at 130 ° C. for 5 hours, in the same manner as in Comparative Example 3 to prepare n-butanol. 1220 parts of PO22.1 mol adduct (b5) were obtained.

Comparative Example 6 The spindle oil was used as the metal working oil (b6) of Comparative Example 3.

Comparative Example 7 Polybutene [Nisseki Polybutene LV- manufactured by Nippon Petrochemical Co., Ltd.
25E] was used as the metal working oil (b7) of Comparative Example 7.

Test Examples The metal working oils a1 to a5 of the above Examples and Comparative Examples will be described below.
And the main items as hydraulic oils b1 to b7 (weight average molecular weight, HLB, kinematic viscosity at 40 ° C., 100 ° C.
Kinematic viscosity, viscosity index, and 200N indicating lubricity at 3
Tables 1 and 2 show the physical properties of the friction coefficient under a load of 00 N and 500 N, the wear scar diameter, the oil film breakage, and the critical temperature at which the lubricating oil separates, which indicates the compatibility with hydrocarbons.

Examples 6 to 9 and Comparative Examples 8 to 14 In the formulation according to Table 3, water-soluble processing oil was obtained and the lubricity of a 5% aqueous solution was measured.

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[Table 1]

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[Table 2]

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[Table 3]

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EFFECT OF THE INVENTION The polyether metal working oil of the present invention has excellent compatibility with hydrocarbons such as mineral oil, and has excellent lubricity and viscosity index. Therefore, it is extremely suitable as a metalworking oil.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) C10N 40:20 C10N 40:20 ZF term (reference) 4H104 BB45A BB46A CA04A CB14A CB15A CB16A CB17A DA02A EA03A EB05 EB07 EB08 EB09 EB10 EB11 EB13 EB14 PA21

Claims (5)

[Claims] 1. A compound represented by the following general formula (1), having an HLB of 6.0 or less and a weight average molecular weight of 500 to 30,000.
A metalworking oil consisting of a polyether (E) which is 0. R ¹ [-{(OCH ₂ CH ₂ CH ₂ CH ₂ ) _m (OA) _n } -OH] _p (1) [wherein R ¹ is a compound having 1 to 6 hydroxyl groups having 1 to 24 carbon atoms] Residue excluding all hydroxyl groups, A is 1,4-
An alkylene group having 2 to 4 carbon atoms excluding a butylene group,
m and n have a weight average molecular weight of (E) of 500 to 30,0.
1 is an integer of 1 or more, and p is an integer of 1 to 6. ] 2. The (OCH₂CH₂CH₂CH₂) Content
But (OCH₂CH₂CH ₂CH₂) And (OA) content
The metalworking according to claim 1, which is 5 to 45 mol% of the measured amount.
oil. 3. The (OCH ₂ CH ₂ CH ₂ CH ₂ ) and (OCH ₂ CH ₂ CH ₂ CH ₂ ).
The metalworking oil according to claim 1, wherein the bond of A) includes a random bond. 4. The metalworking oil according to claim 1, further containing 5 to 90% by mass of a hydrocarbon base oil. 5. A detergent dispersant, an antioxidant, an oiliness agent, an emulsifier, an extreme pressure agent, a metal deactivator, a rust inhibitor, an antifoaming agent, a viscosity index improver and a pour point depressant. The metalworking oil according to any one of claims 1 to 4, which contains one or more additives selected.