JP2002012881A - Lubricating oil - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a lubricating oil excellent in compatibility with hydrocarbons, lubricity, viscosity index and high-temperature detergency. SOLUTION: This lubricating oil comprises (E) a specific polyether represented by general formula (1): R1- (O-CH2CH2CH2CH2)m/(O-A)n}-OR2 [wherein, R1 is a 1-24C hydrocarbon group; R2 is a 1-4C alkyl group; A is one or more kinds selected from 1-4C alkylene groups except 1,4-butylene group; m and n are each an integer of >=1 satisfying that the weight-average molecular weight of the polyether (E) is 500-10,000; and the oxytetramethylene group (O- CH2CH2CH2CH2 group) and the oxyalkylene group (O-A group) may be bound randomly or in a block state] and having <=4 hydrophile-lipophile balance(HLB) and 500-10,000 weight-average molecular weight.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a polyether-based lubricating oil. More specifically, the present invention relates to a polyether-based lubricating oil having excellent compatibility and lubricity with a hydrocarbon-based lubricating oil.

[0002]

2. Description of the Related Art Hydraulic oil, gear oil, engine oil, lubricating oil for textile processing, lubricating oil for metal processing and the like are required to have viscosity characteristics, lubricity, cleanliness at high temperatures, and the like. In particular, when lubricating oil consumed is all burnt in the combustion chamber, such as lubricating oil for two-stroke engines, not only lubricity, high viscosity index, cleanliness at high temperatures, but also hydrocarbon-based substances such as gasoline Compatibility is required. Many polyether-based oils which are considered to have good lubricity, viscosity index, and high-temperature detergency have insufficient compatibility with hydrocarbon-based lubricating oils.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide a polyether-based lubricating oil having excellent compatibility with a hydrocarbon-based lubricating oil and having excellent lubricity, viscosity index and high-temperature detergency.

[0004]

Means for Solving the Problems The present inventors have made intensive studies in view of the above problems, and as a result, have reached the present invention. That is, the present invention is represented by the following general formula (1) and has an HLB of 4
And the weight average molecular weight is 500 to 10,000.
0 is a lubricating oil containing one or more polyethers (E). R ¹ -{(O-CH ₂ CH ₂ CH ₂ CH ₂ ) _m / (OA) _n } -OR ² (1) wherein R ¹ is a hydrocarbon group having 1 to 24 carbon atoms, and R ² is An alkyl group having 1 to 4 carbon atoms, A is at least one selected from alkylene groups having 1 to 4 carbon atoms excluding a 1,4-butylene group, and m and n each have a weight average molecular weight of (E) of 500 to 1
It is an integer of 1 or more that satisfies 0000. Oxytetramethylene group _{(O-CH 2 CH 2 CH} 2 CH 2 group) and may be attached to the block shape are randomly bonded to the oxyalkylene group (O-A groups). ]

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION In the general formula (1), R ¹ is a branched hydrocarbon group having 1 to 24 carbon atoms, and is a linear or branched aliphatic hydrocarbon group, aromatic hydrocarbon group or alicyclic group. Formula hydrocarbon groups are included. Examples of the linear or branched aliphatic hydrocarbon group include an alkyl group (methyl group, ethyl group, n- and i-propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group , Decyl group, undecyl group, dodecyl group,
Tridecyl, tetradecyl, pentadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl,
A tetracosyl group and a 2-ethylhexyl group);
cis- or trans-unsaturated hydrocarbon groups (alkenyl or alkynyl groups such as ethenyl, 1-, 2- and iso-propenyl, butenyl, pentynyl, hexenyl, peptenyl, nonenyl, decenyl Group, undecenyl group, dodecenyl group,
Tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonadecenyl group, eicosenyl group, heneicosenyl group, docosenyl group, tricosenyl group, tetracosenyl group, and the like.

The aromatic hydrocarbon group has 6 to 24 carbon atoms.
Aromatic hydrocarbon group such as phenyl group, alkylaryl group (o, m or p-methylphenyl group, m, p-
Dimethylphenyl group, 2,6-dimethylphenyl group,
o, m or p-ethylphenyl group, pn-butylphenyl group, p-octylphenyl group, p-nonylphenyl group, etc., aralkyl group (benzyl group, phenethyl group, etc.), substituted aralkyl group (o, m Or p-methylbenzyl group, pn-butylphenethyl group, etc.), styrylphenyl group (mono and distyrylphenyl group, etc.)
And a benzylphenyl group (such as a mono- and dibenzylphenyl group). Examples of the alicyclic hydrocarbon group include a cyclopentyl group and a cyclohexyl group. Of these, preferred are those having 4 to 2 carbon atoms.
0 aliphatic or alicyclic hydrocarbon group, especially 8 carbon atoms
To 18 aliphatic or alicyclic hydrocarbon groups. When the number of carbon atoms is 25 or more, the viscosity index becomes poor.

In the general formula (1), R ² has 1 carbon atom.
To 4 linear or branched alkyl groups, for example, methyl group, ethyl group, n- and isopropyl group, n
-, Iso-, sec- and tert-butyl groups. Of these, those having 3 or less carbon atoms are preferred, and more preferably a methyl group, an ethyl group and n-
A propyl group, especially a methyl group. When the number of carbon atoms is 5 or more, the viscosity index becomes poor.

A in the general formula (1) is 1 selected from an alkylene group having 1 to 4 carbon atoms excluding a 1,4-butylene group.
More than a species. The alkylene group has 1 to 1 carbon atoms.
4, preferably 2 to 4 alkylene groups such as methylene, ethylene, 1,2- and 1,3-propylene groups,
1,2-, 2,3-, 1,3- and iso-butylene groups. Of these, preferred are ethylene groups,
1,2-butylene groups, and especially 1,2-propylene groups.

The HLB value of (E) in the present invention is usually 4 or less. It is preferably 3.7 or less, and more preferably 2 to 3.5. When the HLB value of (E) exceeds 4, the compatibility with hydrocarbons such as mineral oil and polybutene deteriorates. The HLB value is a value based on the Oda equation based on an organic conceptual diagram, and its calculation method is described, for example, in "Emulsification and Solubilization Techniques" (1979, Kogaku Tosho Co., Ltd.). For the organic and inorganic values for deriving the HLB value, refer to the inorganic group table (Showa 49) described in "Organic Conceptual Diagram-Basics and Applications-" (Showa 59, Sankyo Shuppan Co., Ltd.).
Year, reported by Fujita et al.).

[0010] (E) weight average molecular weight (Mw) [by gel permeation chromatography (GPC) measurement. The same applies to the following. ] Is 500 to 10,000, preferably 600 to 5,000, more preferably 700 to 4,000. If it is less than 500, the lubricity is poor, and if it exceeds 10,000, the kinematic viscosity becomes too high.

In the general formula (1), m and n may be integers of 1 or more in a range satisfying the molecular weight of the above (E), but lubricity, viscosity index, compatibility with hydrocarbons and low temperature. From the viewpoint of fluidity of the polyoxyalkylene chain [(OC
_{H 2 CH 2 CH 2 CH 2} ) m and (O-A) content of oxytetramethylene groups in total] of _{n (O-CH 2 CH 2} CH 2 CH 2 group) is 10 to 85 mol%, in particular 15 It is preferably about 50 mol%.

Further, (E) has a random bonding portion of an oxytetramethylene group (O—CH ₂ CH ₂ CH ₂ CH ₂ group) and another oxyalkylene group (OA group), which means that flow at a low temperature is possible. It is preferable in that it has excellent characteristics. It is preferred that 80% by mass or more of the oxytetramethylene groups constituting (E) exist in the random binding portion.

The polyether-based lubricating oil of the present invention contains (E) as an essential component, but may contain other polyethers [where one or both of R ¹ and R ² in the general formula (1) are hydrogen atoms. Some polyethers etc.] may be contained. The content is preferably 20% by mass or less.

Preferred examples of (E) include those represented by the following general formula (2). R ¹ -{(O-CH ₂ CH ₂ CH ₂ CH ₂ ) _m / (OA ¹ ) _n } -OR ² (2) R ¹ , R ² , m and n are the same as those in the general formula (1). the same,
A ¹ is an alkylene group having 2 to 4 carbon atoms other than a 1,4-butylene group. This is achieved by adding a monool (e) represented by R ¹ -OH to tetrahydrofuran (hereinafter referred to as T
HF) and one or two or more alkylene oxides having 2 to 4 carbon atoms (hereinafter abbreviated as A ¹ O) other than THF (random and / or block addition), and the resulting polyether The terminal hydroxyl group of all (b) can be produced by alkyl etherification. As A ¹ O to be added, for example, ethylene oxide (EO), propylene oxide (PO), 1,2-, 2,3- and 1,3
-Butylene oxide, isobutylene oxide and the like. Preferred among these are EO, 1,2-butylene oxide, and especially PO. These may be used in combination, and the polymerization mode may be random or block. T
The added mole number (m) of HF is preferably from 3 to 100, and the added mole number (n) of A ¹ O is preferably from 5 to 150.

Examples of catalysts for the addition of THF alone or for copolymerization with A ¹ O include BF ₃ , BCl ₃ ,
Lewis acids such as AlCl ₃ , FeCl ₃ , SnCl ₃ and their complexes [eg BF ₃ ether complex, BF ₃ tetrahydrofuran complex (BF ₃ .THF)]; H ₂ SO ₄ , H
A protic acid such as ClO ₄ ; a perchlorate of an alkali metal such as KClO ₄ or NaClO ₄ ; Ca (ClO ₄ ) ₂ , Mg
(ClO ₄ ) _{2 and} other alkaline earth metal perchlorates; Al
Other metal perchlorates such as (ClO ₄ ) _{3 and the} like can be mentioned. Of these, BF ₃ ether complex and BF ₃ tetrahydrofuran complex (BF ₃ .THF) are preferable.
It is. The catalyst for adding A ¹ O alone may be a commonly used known catalyst. In addition to the above-mentioned catalysts, alkali catalysts such as hydroxides [KOH, NaOH, Cs
Hydroxides of alkali metals or alkaline earth metals such as OH and Ca (OH) ₂ etc.]; oxides (K ₂ O, CaO,
Alkali metal or alkaline earth metal oxides such as BaO); alkali metals (Na, K, etc.) and hydrides thereof (NaH, KH, etc.); amines such as triethylamine, trimethylamine, etc .; Of these, KOH, NaOH, CsOH, BF ₃ ether complex and BF ₃ tetrahydrofuran complex (BF ₃ .TH
F).

The above alkyl ether is obtained by converting (b) an alkyl halide (having 1 carbon atom) in the presence of an alkali (such as a hydroxide of an alkali metal such as KOH, NaOH and CsOH).
To 4). Alkyl group having 1 to 4 carbon atoms are the same as the R ^2. The amount of the alkyl halide is 1/1 to 1 in a molar ratio to the hydroxyl group in (b).
5/1, particularly preferably 1.2 / 1 to 4/1. The amount of the alkali added is 1/1 to 1 in a molar ratio to the hydroxyl group of (b).
0/1, particularly preferably 1.2 / 1 to 5/1. Other examples of (E) include those represented by general formula (3).

[0017]

Embedded image

Wherein A ¹ , R ¹ and R ² are represented by the general formula (1):
The same as in ^(2), A 2 represents an alkylene group having 1 to 4 carbon atoms, m1 and m2 are 0 or an integer of 1 or more satisfying the equation m1 + m2 = m, n1 and n2 wherein n1 + n2 = n1
Represents 0 or an integer of 1 or more that satisfies (E) represented by the general formula (3) is represented by the formula R ¹ ｛(O—CH ₂
CH ₂ CH ₂ CH ₂ ) _m1 / ( _OA ¹ ) _n1 ｝ OH monool (e ¹ ) (R ¹ OH or its THF and / or A ¹ O adduct) and the formula R ² ｛(O -CH ₂ CH ₂ CH ₂ C
_{H 2) m2 / (O-} A 1) n2} monool (e ² represented by OH) (R ² OH or THF and / or A ¹ O
Adduct) (where (e ¹ ) and (e ² ) may be the same or different) is reacted with a dihaloalkane having 1 to 4 carbon atoms in the presence of an alkali to effect etherification (joining). be able to. As the catalyst used for A ¹ O addition and / or THF addition and the alkali used for etherification, those similar to the above can be used. Examples of the dihaloalkane include dichloromethane, 1,2-dichloroethane, 1,2- and 1,3-dichloropropane,
2-, 1,3-, 1,4- and 2,3-dichlorobutane, and the corresponding dibromoalkanes. Dihaloalkane / monool [(e ¹ ) and (e
² )] is preferably 0.5 / 1 to 0.4.

The polyether-based lubricating oil of the present invention preferably contains a hydrocarbon-based lubricating oil as required. Solvent refined oil, paraffinic mineral oil, naphthenic mineral oil, alkyl (10 to 100 carbon atoms) as hydrocarbon-based lubricating oil
Benzene, alkyl (10 to 100 carbon atoms) naphthalene, polyolefin-based lubricating oil [poly-α-olefin (2 to 50 carbon atoms), polybutene, polyisobutene, etc.]
And the like. The kinematic viscosity (measured according to JIS K 2283) of these hydrocarbon-based lubricating oils is 1 to 520 mm ² / s at 40 ° C. Of these, polybutene and polyisobutene are preferred. The mixing ratio of the polyether lubricating oil and the hydrocarbon lubricating oil is arbitrary, but preferably the mass ratio of the polyether lubricating oil / hydrocarbon lubricating oil is 5/95 to 95/5, particularly 20 /
80 to 80/20. Within this range, the mixed lubricating oil can exhibit the characteristics of both polyether and hydrocarbon.

Further, if necessary, selected from detergents and dispersants, antioxidants, oil agents, extreme pressure agents, metal deactivators, rust inhibitors, defoamers, viscosity index improvers, and pour point depressants. It is preferable to include one or more additives as described above to obtain a lubricating oil composition. The amount of the additive is based on the base oil (polyether lubricating oil or a mixture of polyether lubricating oil / hydrocarbon lubricating oil) unless otherwise specified.
% Represents% by mass.

Examples of the detergent and dispersant include neutral or basic sulfonates (eg, petroleum sulfonic acids such as calcium petroleum sulfonate (normal salt) and basic barium sulfonate, and alkyl (C5-C36) substituted aromatic sulfonic acids. Neutral or basic phenates [eg, alkyl (1 to 36 carbon atoms) phenol, alkyl (1 to 36 carbon atoms) phenol sulfide, alkyl (1 to 36 carbon atoms) phenol aldehyde] Neutral or basic phosphonates, thiophosphonates; alkyl (1 to 36 carbon atoms) substituted salicylates; alkyl (5 to 36 carbon atoms) methacrylate or the methacrylate And polar groups (amine, amide, imide, hydroxyl, carboxyl, (E.g., alkyl (C1-C36) methacrylate-vinylpyrrolidinone copolymer (Mw 1,000-100,000), alkyl (99-1 to 10/90)) (C 1-36) Methacrylate-diethylaminoethyl methacrylate copolymer (Mw 1,000-
100,000), alkyl (1 to 36 carbon atoms) methacrylate-polyethylene glycol-methacrylate copolymer (Mw 1,000 to 100,000), etc .;
Substituted alkenyl (C5-C36) succinimide (for example, N-tetraethylenepentamine polyisobutenyl succinimide, etc.); high molecular weight amides (for example, polystearamid (Mw 1,000-100,000), etc.) and the like. No. When used, the amount added is preferably 1-1.
5%, especially 2-10%.

Examples of the antioxidant include phenolic antioxidants (eg, 2,4-dimethyl-6-tert-butylphenol, 4,4-butylidenebis (6-tert-butylmethcresol) and the like); amine-based antioxidants ( For example, phenyl-α-naphthylamine, phenyl-β-naphthylamine and the like); dialkyl (C 1 to C 36) zinc dithiophosphate; diallyl (C 2 to C 36) zinc dithiophosphate; organic sulfide; organic selenide. When used, the amount added is preferably 0.01 to 2%, particularly 0.1 to 1%.

Examples of the oily agent include fats and oils such as lard oil; long-chain fatty acids having 8 to 36 carbon atoms (eg, oleic acid and stearic acid); higher alcohols having 8 to 36 carbon atoms and esters thereof. When used, the amount added is preferably 0.05-2%, especially 0.1-1%.

Examples of extreme pressure agents include lead soaps (lead naphthenate, etc.); sulfur compounds (sulfided fatty acid esters, sulfided palm oil, sulfided terpenes, dibenzyl disulfide, etc.);
Chlorine compounds (chlorinated paraffin, chloronaphthazanthate, 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 phosphoramidate, amine dibutyl phosphate, and the like. When used, the amount added is preferably 1 to 15%, particularly 5 to 10%.

Examples of the metal deactivator include benzotriazole, mercaptobenzothiazole, N, N'-disalicylidene-1,2-diaminopropane, alizarin and the like. When used, the amount added is preferably 0.01 to 2%, particularly 0.1 to 1%.

Examples of the rust inhibitor include dodecane diacid salt, alkenyl succinate having 12 to 22 carbon atoms; alkyl phosphate ester salt having 8 to 18 carbon atoms in the alkyl group; (cyclo) alkylamine (1 carbon atom) To 36) or a heterocyclic amine (C4 to C36) alkylene oxide (C2 to C4) (1 to 10 mol) adduct (for example, cyclohexylamine EO 2 mol adduct, cyclohexylamine PO
2 mol adduct, 1 mol adduct of morpholine EO, 1 mol adduct of morpholine PO); petroleum sulfonate; No. When used, the amount added is preferably 0.05 to 2%, particularly 0.1 to 1%.
It is.

Examples of the antifoaming agent include polyorganosiloxane (eg, polydimethylsiloxane).
When used, the amount added is preferably 1 to 700 pp
m, especially 2 to 100 ppm.

As the viscosity index improver, Mw is 20,000.
0 to 1,500,000 polyalkyl (having 1 to 1 carbon atoms)
8) Methacrylate or polyalkyl (C1-18)
Acrylate; polyisobutylene having Mw of 5,000 to 300,000; Mw of 10,000 to 300,000
Polyalkyl (C8-12) styrene; olefin (C2-12) copolymer [for example, ethylene-propylene (molar ratio 5 / 95-95 / 5) copolymer, styrene-isoprene (molar ratio 5) / 95 to 95/5) hydrogenated copolymers and the like]. When used, the amount added is preferably 1 to 15%, particularly 2 to 10%.

Examples of pour point depressants include polyalkyl (C6-24) methacrylate; naphthalene-chlorinated paraffin condensation product; ethylene-vinyl acetate (molar ratio 5 / 95-95 / 5) copolymer; polyacrylamide Vinyl carboxylate (1 to 36 carbon atoms) -dialkyl (1 to 36 carbon atoms) fumarate (molar ratio 5/95);
９５95/5) copolymer and the like. All of these pour point depressants have a Mw of 1,000 to 100,000. When used, the amount added is preferably 0.05 to
It is 1%, especially 0.1-0.5%.

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

The polyether-based lubricating oil of the present invention can be used for hydraulic oil, gear oil, engine oil, lubricating oil for textiles, lubricating oil for metal working (for example, rolling, grinding, etc.), lubricating oil for refrigerators, etc. Although it can be used, it can be suitably used especially as a lubricating oil such as engine oil for a two-stroke engine.

[0032]

The present invention will be described in detail with reference to the following Examples, but it should not be construed that the present invention is limited thereto. In addition,
The kinematic viscosity and viscosity index of the lubricating oil are in accordance with JIS K 2283
It was measured according to. The pour point was measured according to JIS K 2269. The compatibility was evaluated by measuring the critical temperature of the compatibility with spindle oil [SYC spindle oil manufactured by Cosmo Oil Co., Ltd.] and polybutene [Nisseki Polybutene LV-25E manufactured by Nippon Petrochemical Co., Ltd.]. At a critical temperature of 0 ° C. to 85 ° C., the lubricating oils of Examples and Comparative Examples and the hydrocarbons were mixed at a mass ratio of 30/70 in a test tube, and the temperature until separation was measured. Evaluation of cleanliness at a high temperature was performed as follows. 0.5 g of lubricating oil was placed in an aluminum petri dish (diameter: 5 cm) and kept at 300 ° C. for about 30 minutes. Then, the appearance of the residue in the petri dish was visually observed. The evaluation criteria for high-temperature cleanliness are as follows. ○: Almost no residue such as carbide △: Part of carbide remains ×: A large amount of carbide remains Lubricity was measured using a vibration friction wear tester (SRV tester)
Point contact between a steel ball and a flat steel disk (load 200N, 300
N and 500N) and the wear scar diameter on the steel ball was evaluated. Unless otherwise specified, parts in the text indicate parts by mass.

Production Example 1 Isotridecanol [tridecanol manufactured by Kyowa Hakko Kogyo KK] was placed in a glass autoclave. The same applies hereinafter. ] 2
00 parts (1 mol), THF 504 parts (7 mol) and BF
_3. 7.9 parts of THF are charged and PO
580 parts (10 mol) were added dropwise at 35 to 50 ° C over 10 hours. Thereafter, the mixture was reacted at 50 ° C. for 5 hours and cooled.
Further, 80 parts (2 mol) of powdered NaOH was added,
At 0.6 ° C., 60.6 parts (1.2 mol) of methyl chloride were added dropwise.
Thereafter, unreacted methyl chloride was removed under reduced pressure (pressure 1 to 50 mmHg; the same applies to the degree of reduced pressure in the following examples), and excess NaOH and generated salts were separated by water washing. The organic layer is subjected to an adsorption treatment agent (Kyowa Chemical Industry Co., Ltd. Kyoward 600 and Kyoward 1000). The same applies hereinafter. After filtration and dehydration under reduced pressure, 1168 parts (a1) of a methyl etherified product of a random adduct of isotridecanol in 7 mol of THF / 10 mol of PO was obtained.

Production Example 2 130 parts (1 mol) of 2-ethylhexyl alcohol, 504 parts (7 mol) of THF and 7.5 parts of BF ₃ .THF were charged into a glass autoclave, and 580 parts (10 mol) of PO were added from a pressure dropping funnel. The solution was added dropwise at 35 to 50 ° C over 7 hours. Thereafter, the mixture was reacted at 50 ° C. for 3 hours and cooled. Further, 80 parts (2 mol) of powdered NaOH was added,
At 80 ° C., 60.6 parts (1.2 mol) of methyl chloride were added dropwise. Then, unreacted methyl chloride is removed under reduced pressure,
Excess NaOH and generated salts were separated by water washing. The organic layer is treated with an adsorbent, filtered, dehydrated under reduced pressure, and THF of 7-mol / P of 2-ethylhexyl alcohol.
Terminal methyl etherified product of O10 molar random adduct 1
105 parts (a2) were obtained.

Production Example 3 200 parts (1 mol) of isotridecanol, 504 parts (7 mol) of THF and BF ₃ .T were placed in a glass autoclave.
7.9 parts of HF were charged and PO580 was added from a pressure dropping funnel.
A part (10 mol) was added dropwise at 35 to 50 ° C over 10 hours. Thereafter, the mixture was aged at 50 ° C. for 5 hours and cooled. Further, after adding 4.8 parts of a 48% aqueous NaOH solution, the mixture was treated with an adsorption treatment agent, filtered, and dehydrated under reduced pressure. 642 parts (0.5 mol) of 1220 parts of a random adduct of 7 mol of THF / 10 mol of PO of isotridecanol obtained and KOH
2.27 parts were charged into a glass autoclave, and 116 parts (2 mol) of PO were dropped from the pressure-resistant dropping funnel at 105 ° C for 5 hours. Thereafter, the mixture was reacted at 130 ° C. for 5 hours and cooled. Further, 40 parts (1 mol) of powdered NaOH was added, and 30.3 parts (0.6 mol) of methyl chloride was added dropwise at 80 ° C. Thereafter, unreacted methyl chloride was removed under reduced pressure, and excess NaOH and generated salts were separated and removed by washing with water. The organic layer is treated with an adsorbent, filtered,
After dehydration under reduced pressure, THF of isotridecanol 7 mol / PO
689 parts (a3) of a terminal methyl etherified product of a 10 mol random / PO4 mol block adduct was obtained.

Production Example 4 30 parts of (a1) and 70 parts of polybutene (Nippon Petrochemical Co., Ltd. Nisseki Polybutene LV-25E) were mixed.
100 parts (a4) of a mixture of (a1) and polybutene was obtained.

Comparative Production Example 1 In a glass autoclave, 200 parts (1 mol) of isotridecanol, 504 parts (7 mol) of THF and BF ₃ .T
7.9 parts of HF were charged and PO580 was added from a pressure dropping funnel.
A part (10 mol) was added dropwise at 35 to 50 ° C over 10 hours. Thereafter, the mixture was aged at 50 ° C. for 5 hours and cooled. Further, after adding 4.8 parts of a 48% aqueous NaOH solution, the mixture was treated with an adsorption treatment agent, filtered, and dehydrated under reduced pressure. There were obtained 1220 parts (b1) of a random adduct of isotridecanol in THF 7 mol / PO 10 mol.

Comparative Production Example 2 A glass autoclave was charged with 200 parts (1 mol) of isotridecanol and 3.3 parts of KOH, and 1102 parts (19 mol) of PO was added dropwise from a pressure dropping funnel at 105 ° C. over 33 hours. Thereafter, the mixture was reacted at 130 ° C. for 10 hours and cooled. Further, 80 parts (2 mol) of powdery NaOH was added, and 60.6 parts (1.2 mol) of methyl chloride was added dropwise at 80 ° C. Thereafter, unreacted methyl chloride was removed under reduced pressure, and excess NaOH and generated salts were separated and removed by washing with water. The organic layer is treated with an adsorbent, filtered,
After dehydration under reduced pressure, 1184 parts (b2) of a terminal methyl etherified product of a 19-mol PO adduct of isotridecanol was obtained.

Comparative Production Example 3 200 parts (1 mol) of isotridecanol, 504 parts (7 mol) of THF and BF ₃ .T were placed in a glass autoclave.
8.8 parts of HF was charged and PO46 was poured from a pressure dropping funnel.
A mixture of 4 parts (8 moles) and 220 parts (5 moles) of EO
The solution was added dropwise at 5 to 50 ° C over 10 hours. Then 50 ° C
For 5 hours and cooled. Furthermore, powdered NaOH8
0 parts (2 mol) were added, and 60.6 parts (1.2 mol) of methyl chloride was added dropwise at 80 ° C. Thereafter, unreacted methyl chloride was removed under reduced pressure, and excess NaOH and generated salts were separated and removed by washing with water. The organic layer is treated with an adsorbent, filtered, dehydrated under reduced pressure, and THF of isotridecanol.
1262 parts (b3) of a terminal methyl etherified product of a random adduct of 7 mol / 8 mol of PO / 5 mol of EO were obtained.

Comparative Production Example 4 A glass autoclave was charged with 74 parts (1 mol) of n-butanol and 1.1 parts of KOH.
A mixture of 224.4 parts (5.1 mol) of O and 226.2 parts (3.9 mol) of PO was added dropwise at 110 ° C. over 15 hours. Thereafter, the mixture was reacted at 130 ° C. for 10 hours and cooled. After cooling, the mixture was treated with an adsorbent, filtered, and dehydrated under reduced pressure to obtain 475 parts (b4) of a random adduct of n-butanol with EO 5.1 mol / PO 3.9 mol.

Comparative Production Example 5 Same as Comparative Production Example 4 except that KOH was changed to 4.8 parts, EO was changed to 915.2 parts (20.8 mol), and PO was changed to 916.4 parts (15.8 mol). And n-butanol EO2
0.8 mol / PO 15.8 mol random adduct (b5)
I got

Examples 1-4, Comparative Examples 1-6 (a1)-(a4) were replaced with Examples 1-4, (b1)-(b
5) in Comparative Examples 1 to 5, polybutene [Nippon Petrochemical Co., Ltd.
Nisseki Polybutene LV-25E] was used as the lubricating oil of Comparative Example 6. Mw, HLB, kinematic viscosity at 40 ° C. and 100 ° C. (mm ² / s), viscosity index, 200N representing lubricity,
Tables 1 and 2 show the results of the coefficient of friction and the wear scar diameter under the load of 00N and 500N, the critical temperature at which the lubricating oil indicating compatibility with hydrocarbons separates, the high temperature cleanliness, and the pour point.

[0043]

[Table 1]

[0044]

[Table 2]

All of Examples 1 to 4 using the polyether-based lubricating oil of the present invention have excellent compatibility with hydrocarbons such as spindle oil and polybutene (the critical temperature range is wide), viscosity index, and lubrication. Excellent in terms of heat resistance, high temperature cleanability and pour point. On the other hand, Comparative Examples 1 and 3 to 5 have insufficient compatibility with hydrocarbons. Further, Comparative Example 2 has insufficient lubricity, and Comparative Example 6 has a remarkably poor viscosity index and insufficient lubricity.

[0046]

The polyether-based lubricating oil of the present invention has excellent compatibility with hydrocarbons such as mineral oil and polybutene, and has excellent lubricity, viscosity index, high-temperature detergency, and pour point.
It is extremely suitable as a lubricating oil such as engine oil for a two-stroke engine.

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Claims (7)

[Claims] 1. HLB is represented by the following general formula (1):
And the weight average molecular weight is 500 to 10,000.
A lubricating oil containing one or more polyethers (E). R ¹ -{(O-CH ₂ CH ₂ CH ₂ CH ₂ ) _m / (OA) _n } -OR ² (1) wherein R ¹ is a hydrocarbon group having 1 to 24 carbon atoms, and R ² is An alkyl group having 1 to 4 carbon atoms, A is at least one selected from alkylene groups having 1 to 4 carbon atoms excluding a 1,4-butylene group, and m and n each have a weight average molecular weight of (E) of 500 to 1
It is an integer of 1 or more that satisfies 0000. Oxytetramethylene group _{(O-CH 2 CH 2 CH} 2 CH 2 group) and may be attached to the block shape are randomly bonded to the oxyalkylene group (O-A groups). ] 2. The lubricating oil according to claim 1, wherein the content of the oxytetramethylene group (O—CH ₂ CH ₂ CH ₂ CH ₂ group) in the polyoxyalkylene chain is 10 to 85 mol%. 3. The method according to claim 1, wherein (E) is an oxytetramethylene group (O-
CH ₂ CH ₂ CH ₂ CH ₂ group) and oxyalkylene group (O-
The lubricating oil according to claim 1 or 2, which has a random binding portion of (A group). 4. The lubricating oil according to claim ¹ , wherein R ¹ has 4 or more carbon atoms and R ² has 3 or less carbon atoms. 5. The lubricating oil according to claim 1, further comprising a hydrocarbon lubricating oil. 6. One or more selected from detergents / dispersants, antioxidants, oil agents, extreme pressure agents, metal deactivators, rust inhibitors, defoamers, viscosity index improvers, and pour point depressants. The lubricating oil according to any one of claims 1 to 5, further comprising an additive. 7. A two-stroke engine oil comprising the lubricating oil according to claim 1. Description: