JP2000008068A - Ether lubricant additive and lubricant composition - Google Patents

Abstract

An object of the present invention is to provide an ether lubricant additive having excellent lubricity. SOLUTION: The ether-based lubricating oil additive and the lubricating oil composition of the present invention have the following general formula (1): (Wherein R ¹ , R ² and R ³ represent a hydrocarbon group;
⁴ and R ⁵ represent a hydrogen atom or a hydrocarbon group, m and n represent 0 or a number of 1 or more, and p represents a number of 1 or more. However, m and n are never 0 at the same time. ).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to an ether-based lubricating oil additive and a lubricating oil composition using the same.

[0002]

2. Description of the Related Art In recent years, lubricating devices have been increased in speed, output,
There is a demand for miniaturization and maintenance-free. Along with this, various problems have also occurred in lubricating oil. For example, a reduction in the size of a lubricating device has led to a decrease in the amount of lubricating oil. Also, the use of three-way catalysts to suppress the generation of nitrogen oxides (NO _X ) in exhaust gas increases the amount of NO _X gas leaking into the crankcase, which accelerates the deterioration of lubricating oil. are doing. In addition, from the requirement of maintenance-free, lubricating oils are required to have a long life, that is, a long drain property. As described above, the demand for lubricating oils to have high stability under severe conditions is increasing year by year.

[0003] On the other hand, lubricating oils are subject to physical shearing during use or exposed to oxidizing atmosphere at high temperature and high pressure.
Degrades over time. The same applies to various additives that are added to lubricating oils, when they undergo oxidative deterioration before exhibiting their original performance and decompose to fail to exhibit their performance, or adversely affect the lubricating oil. There is also.

[0004] In recent years, attempts have been made to improve the temperature-viscosity characteristics of lubricating base oils themselves in order to improve the problem of seizure at high temperatures and the problem of energy loss at low temperatures of engines. That is, the use of a refined base oil obtained by highly refining a mineral oil obtained from crude oil as a lubricating base oil or a synthetic base oil synthesized by chemical means is increasing. For this reason, components having antioxidant performance, such as sulfur compounds and nitrogen compounds, which are impurities originally contained in mineral oil, have been eliminated, and the problem that the thermal stability of the lubricating base oil alone is reduced. Has occurred.

[0005] Because of these problems, a variety of additives have been added to lubricating base oils to obtain desired performance. One of the additives includes glycerin monoesters. Glycerin monoester is inexpensive, and
Since it has an excellent friction adjusting effect, it is used by being added to a wide range of lubricating oils including engine oils. However, it is disadvantageous that glycerin monoester causes hydrolysis in the presence of water. Glycerin monoethers are known as additives that have solved this disadvantage.

[0006]

Glycerin ethers have hitherto been known to be effective as friction modifiers. For example, JP-A-59-25890 discloses that zinc dithiophosphate (ZDTP) and glycerin ethers such as batyl alcohol, chimyl alcohol, and seraky alcohol are added to a mineral oil base oil to have excellent friction adjusting ability. It is described. JP-A-9-1576
No. 76 describes that an ether-based additive such as glycerin monooleyl ether (ceracyl alcohol) exhibits excellent effects, particularly when added to lubricating oil for refrigerators.

[0007] However, glycerin ethers represented by the above-mentioned glycerin monooleyl ether and the like are sometimes excellent in hydrolytic stability but not satisfactory in lubricity in some cases. Then, the present inventors diligently studied and developed an ether lubricant additive having excellent lubricity.

[0008]

That is, the present invention provides the following general formula (1):

Embedded image (Wherein R ¹ , R ² and R ³ represent a hydrocarbon group;
⁴ and R ⁵ represent a hydrogen atom or a hydrocarbon group, m and n represent 0 or a number of 1 or more, and p represents a number of 1 or more. However, m and n are never 0 at the same time. ) Is an ether lubricant additive. The present invention is also a lubricating oil composition containing the above-mentioned ether-based lubricating oil additive and a phenolic or amine-based antioxidant in a lubricating base oil.

[0009]

DETAILED DESCRIPTION OF THE INVENTION The ether lubricant additive of the present invention is represented by the following general formula (1):

Embedded image In the general formula (1), R ¹ represents a hydrocarbon group. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, an aryl group, a cycloalkyl group, and a cycloalkenyl group.

Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl,
Tert-butyl, tert-butyl, pentyl, isopentyl, secondary pentyl, neopentyl, tert-pentyl, hexyl, secondary hexyl, heptyl, secondary heptyl, octyl, 2-ethylhexyl, secondary octyl, nonyl, secondary nonyl, decyl , 2nd grade decyl, undecyl,
Secondary undecyl, dodecyl, secondary dodecyl, tridecyl, isotridecyl, secondary tridecyl, tetradecyl,
Secondary tetradecyl, hexadecyl, secondary hexadecyl,
Stearyl, icosyl, docosyl, tetracosyl, triacontyl, 2-butyloctyl, 2-butyldecyl,
2-hexyloctyl, 2-hexyldecyl, 2-octyldecyl, 2-hexyldecyl, 2-octyldodecyl, 2-decyltetradecyl, 2-dodecylhexadecyl, 2-hexadecyloctadecyl, 2-tetradecyloctadecyl, monomethyl Branched-isostearyl and the like.

Examples of the alkenyl group include vinyl, allyl, propenyl, butenyl, isobutenyl, pentenyl, isopentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tetradecenyl, oleyl and the like.

Examples of the aryl group include phenyl, toluyl, xylyl, cumenyl, mesityl, benzyl, phenethyl, styryl, cinnamyl, benzhydryl, trityl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octyl. Phenyl, nonylphenyl, decylphenyl, undecylphenyl, dodecylphenyl,
Examples include phenylphenyl, benzylphenyl, styrenated phenyl, p-cumylphenyl, α-naphthyl and β-naphthyl groups.

Examples of the cycloalkyl group and the cycloalkenyl group include, for example, cyclopentyl, cyclohexyl, cycloheptyl, methylcyclopentyl, methylcyclohexyl, methylcycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, methylcyclopentenyl, methylcyclohexenyl, methylcyclohepenyl And a thenyl group.

Among these, a hydrocarbon group having 6 to 36 carbon atoms is preferable from the viewpoint of lubricity and oil solubility, and a hydrocarbon group having 8 carbon atoms is preferred.
~ 24 alkyl groups, alkenyl groups or aryl groups are preferred.

R ² and R ³ represent a hydrocarbon group, preferably an alkylene group having 2 to 4 carbon atoms. The (R ² —O) _m and (R ³ —O) _n portions of the general formula (1) are subjected to addition polymerization of an alkylene oxide such as ethylene oxide, propylene oxide, butylene oxide, α-olefin oxide, and styrene oxide. Can be obtained. By adding an alkylene oxide such as ^(R 2 _{-O) m} and ^{(R 3} -
O) When forming the _n portion, R ² and R ³ are determined by the alkylene oxide to be added and the like. The polymerization form of the alkylene oxide or the like to be added is not particularly limited, and may be homopolymerization of one kind of alkylene oxide or the like, random copolymerization of two or more kinds of alkylene oxides or the like, block copolymerization, or random / block copolymerization or the like. . As R ² and R ³ , an ethylene group is most preferable. When R ² and R ³ are two or more groups, one of them is preferably an ethylene group. The polymerization degrees m and n are 0 or a number of 1 or more, preferably 0 to 20, more preferably 0 to 10, and still more preferably 1 to 5, and m and n are not 1 at the same time. P is a number of 1 or more, and preferably 1 to 3.

R ⁴ and R ⁵ represent a hydrogen atom or a hydrocarbon group, and one of them is preferably a hydrogen atom, and more preferably both are hydrogen atoms.

[0017] The ether lubricant additive of the present invention improves lubricity. Also, because it is an ether compound,
There is no hydrolysis. Accordingly, unlike ester-based lubricants such as glycerin monooleate, even when water is mixed in the lubricating oil, the lubricating oil does not deteriorate, so that there is no change in lubricity. Also, compared to lubricants such as glycerin monooleyl ether, (R ² -O) _m -R ⁴ and (R ³ -O) _n
Because it has a group -R ^5, has excellent lubricity because strong adsorption force to the metal surface.

The ether lubricant additive of the present invention is used by being blended with a lubricant base oil. The compounding amount is not particularly limited, but if the amount is too small, the effect of improving lubricity is not sufficiently exhibited, and if the amount is too large, sludge is caused. Therefore, the preferable amount is 0.01 to 20% by weight based on the lubricating base oil, More preferably, it is 0.05 to 15% by weight.

When the ether-based lubricating oil additive of the present invention is used in combination with a phenol-based or amine-based antioxidant, lubricating properties can be exhibited over a long period of time. As the phenolic antioxidant, a hindered phenolic antioxidant having a tertiary butyl group or a tertiary pentyl group in the molecule is particularly preferable. For example, 2,6-di-tert.-butylphenol, 2,6-di-ter.
t-butyl-p-cresol, 2,6-di-tert.
-Butyl-4-methylphenol, 2,6-di-ter
t-butyl-4-ethylphenol, 2,4-dimethyl-6-tert.-butylphenol, 4,4′-methylenebis (2,6-di-tert.-butylphenol), 4,4′-bis (2 , 6-di-tert.-butylphenol), 4,4'-bis (2-methyl-6-t
tert.-butylphenol), 2,2′-methylenebis (4-methyl-6-tert.-butylphenol), 2,2′-methylenebis (4-ethyl-6-te
-butylphenol), 4,4'-butylidenebis (3-methyl-6-tert.-butylphenol), 4,4'-isopropylidenebis (2,6-di-
tert.-butylphenol), 2,2′-methylenebis (4-methyl-6-cyclohexylphenol),
2,2′-methylenebis (4-methyl-6-nonylphenol), 2,2′-isobutylidenebis (4,6-dimethylphenol), 2,6-bis (2′-hydroxy-3′-tert. -Butyl-5'-methylbenzyl)
4-methylphenol, 3-tert.-butyl-4-
Hydroxyanisole, 2-tert.-butyl-4-
Hydroxyanisole, 4,4'-thiobis (3-methyl-6-tert.-butylphenol), 4,4'-
Thiobis (2-methyl-6-tert.-butylphenol), 2,2′-thiobis (4-methyl-6-ter
t. -Butylphenol), 2,6-di-tert. −
Butyl-α-dimethylamino-p-cresol, 2,6
-Di-tert. -Butyl-4 (N, N'-dimethylaminomethylphenol), bis (3,5-di-ter
t. -Butyl-4-hydroxybenzyl) sulfide, tris {(3,5-di-tert.-butyl-4-
Hydroxyphenyl) propionyl-oxyethyl diisocyanurate, tris (3,5-di-tert.-butyl-4-hydroxyphenyl) isocyanurate,
1,3,5-tris (3 ′, 5′-di-tert.-butyl-butyl-4-hydroxybenzoyl) isocyanurate, bis {2-methyl-4- (3-n-alkylthiopropionyloxy) -5 -Tert. -Butylphenyl disulfide, 1,3,5-tris (4-di-t
ert. -Butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, tetraphthaloyl-di (2,6-dimethyl-4-tert.-butyl-3-hydroxybenzylsulfide), 6- (4-hydroxy- 3,5-di-tert.-butylanilino) -2,
4-bis (octylthio) -1,3,5-triazine,
2,2-thio- {diethyl-bis-3- (3,5-di-
tert. -Butyl-4-hydroxyphenyl) propionate, N, N'-hexamethylenebis (3,5-
Di-tert. -Butyl-4-hydroxy-hydrocinamide), 3,5-di-tert. -Butyl-4-hydroxy-benzyl-phosphoric acid diester, bis (3-methyl-4-hydroxy-5-tert.-butylbenzyl)
Other than sulfide, bisphenol A, alkylated bisphenol A, polyalkylated bisphenol A, etc.

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Embedded image (In the formula, Me represents a methyl group, t-Bu is ter
t. Represents a -butyl group, R represents a monovalent hydrocarbon group, and R 'represents a divalent hydrocarbon group. ) And the like.

As the amine-based antioxidant, an aromatic amine-based antioxidant is particularly preferred. For example, naphthylamine antioxidants such as 1-naphthylamine, phenyl-1-naphthylamine, p-octylphenyl-1-naphthylamine, p-nonylphenyl-1-naphthylamine, p-dodecylphenyl-1-naphthylamine and phenyl-2-naphthylamine Agent; N, N'-diisopropyl-
p-phenylenediamine, N, N'-diisobutyl-p
-Phenylenediamine, N, N'-diphenyl-p-phenylenediamine, N, N'-di-β-naphthyl-p-
Phenylenediamine, N-phenyl-N'-isopropyl-p-phenylenediamine, N-cyclohexyl-
N'-phenyl-p-phenylenediamine, N-1,3
Phenylenediamine antioxidants such as -dimethylbutyl-N'-phenyl-p-phenylenediamine, dioctyl-p-phenylenediamine, phenylhexyl-p-phenylenediamine, phenyloctyl-p-phenylenediamine; dipyridylamine, diphenylamine,
p, p'-di-n-butyldiphenylamine, p, p '
-Di-tert. -Butyldiphenylamine, p, p '
-Di-tert. -Pentyldiphenylamine, p,
p'-dinonyldiphenylamine, p, p'-didecyldiphenylamine, p, p'-didodecyldiphenylamine, p, p'-distyryldiphenylamine, p,
Examples thereof include diphenylamine-based antioxidants such as p′-dimethoxydiphenylamine, 4,4′-bis (4-α, α-dimethylbenzoyl) diphenylamine, and p-isopropoxydiphenylamine.

The amount of these phenolic or amine-based antioxidants to be added is not particularly limited. However, if the amount is too small, the antioxidant effect is not sufficient, and if the amount is too large, there is no effect corresponding to the added amount and there is a technical meaning. , Preferably 0.01 to 5% by weight, more preferably 0.05 to 3% by weight, based on the base oil.

The lubricating base oil which can be used in the present invention may be any one of a mineral oil, a synthetic oil and a mixture thereof. The kinematic viscosity of the lubricating base oil is not particularly limited, but is preferably 1 to 50 cSt at 100 ° C, and 10 to 1 at 40 ° C.
000 cSt, and the viscosity index (VI) is preferably 70
The number is more preferably 100 or more.

Mineral oil is separated from natural crude oil, and is produced by appropriately distilling, refining, and the like.
Main component of mineral oil is hydrocarbon (mostly paraffins)
And further contains a naphthene component, an aromatic component, and the like. Base oils which have been subjected to hydrorefining, solvent dewaxing, solvent extraction, solvent dewaxing, hydrogen dewaxing, catalytic dewaxing, hydrocracking, alkali distillation, sulfuric acid washing, clay treatment, etc. are also preferably used. be able to. These purification means are appropriately combined, and it is effective to repeat the same treatment in a plurality of stages. For example, (A) a method in which a distillate is subjected to a solvent extraction treatment or a solvent extraction treatment followed by a hydrogenation treatment and then a sulfuric acid washing, (B) a method in which a distillate oil is subjected to a hydrogenation treatment and then a dewaxing treatment, (C) a method of subjecting a distillate to solvent extraction and then hydrotreating, (D) a method of subjecting a distillate to solvent extraction and a clay treatment, and (E) a distillate of two or more stages of hydrogen. (F) Hydrotreating distillate oil, or alkali distilling or sulfuric acid washing treatment after hydrogenation treatment, or these treatments A method of mixing oil is effective.

By performing these treatments, it is possible to remove aromatic components, sulfur components, nitrogen components, and the like. With the current technology, these impurities can be removed to a trace amount or less, but aromatics have an effect of making the lubricating oil additive easy to dissolve, so that about 3 to 5% by weight remains. There is also. For example, the sulfur content and the nitrogen content in the currently used highly refined mineral oil are 0.01% by weight or less, and in some cases 0.005% by weight or less. On the other hand, the aromatic content is 1% by weight or less, and in some cases, 0.05% by weight or less, and about 3% by weight remains.

The synthetic oil is a chemically synthesized lubricating base oil, such as poly-α-olefin, polyisobutylene (polybutene), diester, polyol ester, phosphate ester, silicate ester, and the like. Polyalkylene glycol, polyphenyl ether, silicone,
Examples include fluorinated compounds and alkylbenzenes. Among them, poly-α-olefin, polyisobutylene (polybutene), diester, polyol ester,
Polyalkylene glycol and the like can be used for general purposes, and can be preferably used for internal combustion engine oil, processing oil and the like.

Examples of the poly-α-olefin include 1
-Hexene, 1-octene, 1-nonene, 1-decene,
Examples thereof include those obtained by polymerizing or oligomerizing 1-dodecene, 1-tetradecene, and the like, and those obtained by hydrogenating them. Examples of the diester include glutaric acid,
Examples include dibasic acids such as adipic acid, azelaic acid, sebacic acid and dodecane diacid, and diesters of alcohols such as 2-ethylhexanol, octanol, decanol, dodecanol and tridecanol. Examples of the polyol ester include neopentyl glycol, trimethylolethane, trimethylolpropane, glycerin, pentaerythritol, sorbitol, dipentaerythritol, tripentaerythritol, or a polyol such as an alkylene oxide adduct thereof, butyric acid, isobutyric acid, Esters with fatty acids such as valeric acid, isovaleric acid, pivalic acid, capric acid, caproic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, and oleic acid. Examples of the polyalkylene glycol include polyethylene glycol, polypropylene glycol, polyethylene glycol monomethyl ether, mono- or dimethyl ether of a block or random copolymer of ethylene oxide / propylene oxide, and the like.

Since these synthetic oils are each chemically synthesized, they are single substances or mixtures of homologues. Therefore, for example, synthetic oils such as poly-α-olefin, polyisobutylene (polybutene), diester, polyol ester, and polyalkylene glycol are used as impurities contained in mineral oil such as benzene, polycyclic condensed aromatic components, and thiophene. Of sulfur, nitrogen such as indole and carbazole are not included.

The ether lubricant additive of the present invention comprises:
If necessary, it can be used in combination with other lubricating oil additives. Representative lubricating oil additives include oil agents, friction modifiers, extreme pressure agents, other antioxidants, detergents, dispersants,
Viscosity index improvers, defoamers, rust inhibitors, pour point depressants and the like.

Examples of the oil agent include fatty acids such as capric acid, caproic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, behenic acid, linoleic acid, linolenic acid, lauryl alcohol, and myristyl alcohol. , Palmityl alcohol, stearyl alcohol, alcohols such as oleyl alcohol, laurylamine, myristylamine, palmitylamine, stearylamine, amines such as oleylamine,
Examples include amides such as laurylamide, myristylamide, palmitylamide, stearylamine, and oleylamine.

Examples of the friction modifier include capric acid (mono, di, tri) glyceride and caproic acid (mono,
Di, tri) glyceride, caprylic acid (mono, di, tri)
Glyceride, lauric acid (mono, di, tri) glyceride, myristic acid (mono, di, tri) glyceride, palmitic acid (mono, di, tri) glyceride, stearic acid (mono, di, tri) glyceride, oleic acid (mono) ,
Esters such as di- and tri-glycerides; metal salts such as oxymolybdenum dialkyl dithiocarbamate and oxymolybdenum dialkyl dithiophosphate; polyol ethers and polyethers.

Examples of extreme pressure agents include sulfurized olefins,
Sulfurized paraffin, Sulfurized polyolefin, Sulfurized lard, Sulfurized fish oil, Sulfurized whale oil, Sulfurized soybean oil, Sulfurized pinene oil, Sulfurized phenol, Sulfurized alkyl phenol, Dialkyl polysulfide, Dibenzyl disulfide, Diphenyl disulfide, Polyphenylene sulfide, Alkyl mercaptan, Alkyl sulfonic acid, Dithiocarbamine Acid ester, 1,3,4-thiadiazole derivative, thiuram disulfide, butyl (thio, dithio) phosphate, hexyl (thio, dithio) phosphate, octyl (thio,
Dithio) phosphate, 2-ethylhexyl (thio, dithio) phosphate, nonyl (thio, dithio) phosphate, decyl (thio, dithio) phosphate, lauryl (thio, dithio) phosphate, myristyl (thio, dithio) phosphate, palmityl (thio, Dithio) phosphate, stearyl (thio, dithio) phosphate,
Oleyl (thio, dithio) phosphate, phenyl (thio, dithio) phosphate, cresyl (thio, dithio)
(Thio, dithio) phosphoric acids such as phosphates and the like.

Examples of the sulfur-based antioxidants include dilauryl thiodipropionate, dimyristyl thiodipropionate, distearyl thiodipropionate, lauryl stearyl thiodipropionate, dimyristyl thiodipropionate, and distearyl- β, β′-thiodibutyrate, 2-mercaptobenzimidazole, 2-mercaptomethylbenzimidazole, 2-benzimidazole disulfide, dilauryl sulfide, amylthioglycolate and the like.

Examples of the phosphorus-based antioxidant include triphenyl phosphite, trinonyl phenyl phosphite, triisodecyl phosphite, diphenyl isodecyl phosphite, phenyl diisotridecyl phosphite, trioctadecyl phosphite, and tridecyl phosphite. Phyte, diphenylnonylphenylphosphite, trilauryltrithiophosphite, tris (cyclohexylphenyl) phosphite, bis (2-ethylhexyl) phosphite, diisodecylpentaerythritol diphosphite, distearylpentaerythritol diphosphite, tetraphenyldipropylene Glycol diphosphite and the like.

Examples of the metal salt-based antioxidants include nickel dithiocarbamate, zinc-2-mercaptobenzimidazole and the like.

Examples of the detergent include calcium sulfonate, calcium phenate, calcium salicylate, magnesium sulfonate, magnesium phenate, magnesium salicylate, barium sulfonate, barium phenate, and barium salicylate. Examples of the dispersant include polyalkenyl succinimide, polyalkenyl succinimide boride, benzylamine and the like. Examples of the viscosity index improver include poly (meth) acrylate, polyisobutylene, polystyrene, ethylene-propylene copolymer, styrene-isobutylene copolymer and the like.

When the lubricating oil composition is used as a grease, the lubricating oil additive of the present invention is added to a base grease obtained by adding a thickener to a lubricating base oil composed of mineral oil or synthetic oil. . As the thickener, for example, a soap-based or complex soap-based thickener, terephthalate-based thickener,
Organic non-soap thickeners such as urea-based thickeners, polytetrafluoroethylene, fluorinated ethylene-propylene copolymers, and inorganic non-soap-based thickeners.

The lubricating oil additive of the present invention can be used by adding it to lubricating oils for various uses. For example, industrial lubricating oils,
Turbine oil, machine oil, bearing oil, compressor oil, hydraulic oil, hydraulic oil, internal combustion engine oil, refrigeration oil, gear oil, oil for automatic transmission (ATF), oil for continuously variable continuously variable transmission (CVT oil), Examples include a transaxle fluid, metal working oil, various greases, and the like. Among them, it is suitable as a lubricating oil additive for internal combustion engine oils such as vehicle engines, two-cycle engines, aircraft engines, marine engines, and locomotive engines.
Examples of the internal combustion engine include a gasoline engine, a diesel engine, a jet engine, a gas turbine engine, an alcohol engine, and the like.

[0038]

The present invention will be described more specifically with reference to the following examples. In the following examples, “parts” and “%” are based on weight unless otherwise specified. The samples used for the test are as follows. In addition, EO is an abbreviation for ethylene oxide.

<Lubricant base oil> Mineral oil obtained from crude oil is
A mineral oil-based high VI oil obtained by a hydrocracking process method. The viscosity is 4.1 cSt at 100 ° C. and 1 at 40 ° C.
8.3 cSt, VI = 126.

<Ether-based lubricating oil additive of the present invention> Product 1 of the present invention: glycerol monooleyl ether EO 1 mol adduct [in the general formula (1), R ¹ = oleyl group,
R ³ = ethylene group, R ⁴ = R ⁵ = hydrogen atom, m = 0, n = 1, p = 1] Invention product 2: glycerin monooleyl ether EO 2 mol adduct (R ¹ = oleyl group, R ² = R ³ = ethylene group, R ⁴ = R ⁵ = hydrogen atom, m = 1, n =
1, p = 1) Invention product 3: glycerin monooleyl ether EO 4-mol adduct (R ¹ = oleyl group, R ² = R ³ = ethylene group, R ⁴ = R ⁵ = hydrogen atom, m = 2, n =
2, p = 1) Invention product 4: glycerin monolauryl ether EO ¹ mol adduct (R ¹ = oleyl group, R ³ = ethylene group, R ⁴
= R ⁵ = hydrogen atom, m = 0, n = 1, p =
1) Invention product 5: glycerin monononyl phenyl ether P
O1 mole adduct (R ¹ = nonylphenyl group, R ³ = propylene group, R ⁴ = R ⁵ = hydrogen atom, m =
0, n = 1, p = 1) Invention product 6: diglycerin monooleyl ether EO1
Molar adduct (R ¹ = oleyl group, R ³ = ethylene group, R
⁴ = ^{R 5} = hydrogen, m = 0, n = 1 , p
= 2)

<Antioxidant> Antioxidant 1:

Embedded image (R is an oleyl group) Antioxidant 2: 4,4'-methylenebis (2,6-di-tert.-butylphenol) Antioxidant 3:

Embedded image Antioxidant 4:

Embedded image Antioxidant 5: p, p'-dioctyldiphenylamine Antioxidant 6: diphenyl-p-phenylenediamine Antioxidant 7: phenyl-1-naphthylamine

<Comparative product> Comparative product 1: glycerin monooleyl ester Comparative product 2: oleic amide Comparative product 3: glycerin monooleyl ether

The lubricating oil composition obtained from the above components was subjected to a lubricating oil oxidation deterioration test for an internal combustion engine by the following method, and then to a friction coefficient measurement test. <Lubricating oil oxidation stability test for internal combustion engine> The lubricating oil oxidation stability test for internal combustion engine was performed in accordance with JIS-K-2514. In addition, the temperature of the thermostat was set to 165.5 ° C., and the sample stirring rod was stirred at 1,300 revolutions per minute for 24 hours to deteriorate the sample oil.

<Friction coefficient measurement test> The friction coefficient was measured using SRV
The measurement was performed using a test machine. The test was performed under ball-on-plate line contact conditions. That is, the upper cylinder (φ
15 × 22mm) plate (φ24 × 6.85mm)
It was set on the top and reciprocated under the following conditions, and the friction coefficient was measured after 15 minutes. The material was SUJ-2 for both. Load: 200N Temperature: 80 ° C Measurement time: 15 minutes Amplitude: 1mm Cycle: 50Hz

[0045]

[Table 1]

[0046]

[Table 2]

[0047]

[Table 3]

[0048]

The effect of the present invention is to provide a novel ether-based lubricating oil additive and a lubricating oil composition using the same.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C10M 133/40 C10M 133/40 141/02 141/02 141/06 141/06 // C10N 30:06 30 : 10 (72) Inventor Kazuhisa Morita 7-35, Higashiogu, Arakawa-ku, Tokyo Asahi Denka Chemical Industry Co., Ltd. (72) Inventor Kazuhiro Umehara 7-35, Higashiogu, Arakawa-ku, Tokyo In-house F term (reference) 4H104 BB05C BB08C BE07C DA02A EB02 LA03 PA41

Claims (5)

[Claims] 1. The following general formula (1): (Wherein R ¹ , R ² and R ³ represent a hydrocarbon group;
⁴ and R ⁵ represent a hydrogen atom or a hydrocarbon group, m and n represent 0 or a number of 1 or more, and p represents a number of 1 or more. However, m and n are never 0 at the same time. An ether-based lubricating oil additive represented by). 2. The ether lubricant additive according to claim 1, wherein R ² and R ³ are an alkylene group having 2 to 4 carbon atoms, and m and n are 0 to 10. 3. R ¹ is an alkyl group having 8 to 24 carbon atoms,
3. The ether lubricant additive according to claim 1, which is an alkenyl group or an aryl group. 4. A lubricating oil composition comprising the lubricating base oil containing the ether lubricating oil additive according to claim 1 and a phenolic or amine antioxidant. 5. The phenolic antioxidant is a hindered phenolic antioxidant having a tertiary butyl group or a tertiary pentyl group in a molecule, and the amine antioxidant is an aromatic amine antioxidant. Claim 4.
The lubricating oil composition according to the above.