WO2012035954A1 - 酸化防止剤組成物及びそれを含有する潤滑油組成物 - Google Patents
酸化防止剤組成物及びそれを含有する潤滑油組成物 Download PDFInfo
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- WO2012035954A1 WO2012035954A1 PCT/JP2011/069253 JP2011069253W WO2012035954A1 WO 2012035954 A1 WO2012035954 A1 WO 2012035954A1 JP 2011069253 W JP2011069253 W JP 2011069253W WO 2012035954 A1 WO2012035954 A1 WO 2012035954A1
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- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/04—Hydroxy compounds
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- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
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Definitions
- the present invention relates to an antioxidant composition capable of prolonging the life of a lubricating oil, and a lubricating oil composition containing the antioxidant composition.
- antioxidants there are various types of antioxidants such as phenol type, amine type, sulfur type and phosphorus type, but from the problem of waste oil treatment etc., lubricating oil tends to avoid additives containing sulfur atom and phosphorus atom. In general, phenolic and amine antioxidants are used. In addition, longer life of lubricating oil is required due to the increase in temperature of lubricating oil due to the high performance of machinery requiring lubricating oil and the demand for reduction of waste oil processing amount, and from the market There is a great demand for performance improvement for antioxidants.
- Patent Document 1 contains, in the mineral oil and / or synthetic base oil, an amine antioxidant and a phenol antioxidant in a total amount of 1.2% by mass or more, and nitrogen of the amine antioxidant.
- the mass ratio (N / O) of the component (N) to the oxygen content (O) of the phenolic antioxidant is 0.06 to 0.50, and zinc dialkyl dithiophosphate (ZnDTP) is 0 (phosphorus (P))
- ZnDTP zinc dialkyl dithiophosphate
- P phosphorus
- Patent Document 2 also includes a lubricating base oil of natural and / or synthetic origin, a first antioxidant comprising a specific secondary diarylamine, a second antioxidant comprising a specific substituted para-phenylenediamine, and A lubricant composition is disclosed which comprises a third antioxidant consisting of a specific substituted phenol.
- Patent Document 3 discloses an antioxidant composition comprising an organic molybdenum compound and a lubricating base oil having a total aromatic content of 20 to 100% by mass.
- Patent Document 4 discloses an antioxidant composition for lubricating oil comprising a specific amine compound and a phenol compound containing one or more ester groups.
- JP 2008-101144 A Japanese Patent Application Publication No. 2008-523203 Japanese Patent Application Publication No. 2006-117728 JP, 2009-197135, A
- Patent Document 4 and the like high oxidation prevention performance may not be obtained depending on the operating temperature, and in Patent Document 3 and the like, metal atoms are mixed in the lubricating oil, so the load on the environment in disposal etc. is large. There is a problem of becoming Because of this, as in Patent Documents 1 and 2, many attempts have been made to improve the antioxidant performance by combining existing antioxidants that do not contain metal atoms, but the high antioxidant performance meeting the demand is The present situation is that it has not been obtained.
- the problem to be solved by the present invention is to provide a metal element-free antioxidant composition and a lubricating oil composition containing the antioxidant composition, which can realize further prolongation of the lubricating oil life. More specifically, an antioxidant composition which combines a specific phenolic compound with a general amine type or phenol type antioxidant and exerts a synergistic effect to exhibit good antioxidant performance, and the oxidation It is an object of the present invention to provide a lubricating oil composition containing the inhibitor composition.
- the present invention contains a compound (A) represented by the following general formula (1), an amine antioxidant (B) and / or a phenolic antioxidant (C) other than the compound (A)
- An antioxidant composition characterized by: (Wherein R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and n represents a number of 1 to 3)
- the effect of the present invention is to provide a metal atom-free antioxidant composition and a lubricating oil composition containing the antioxidant composition, which can realize further prolonging the life of the lubricating oil.
- the compound (A) used in the present invention can be represented by the following general formula (1): (Wherein R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and n represents a number of 1 to 3)
- R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
- alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, branched propyl group, butyl group and branched butyl group.
- R is preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom, since it is inexpensive and easily available.
- N in the general formula (1) represents a number of 1 to 3.
- R is a hydrogen atom and n is 1
- the compound represented by the general formula (1) is 1-styrenated phenol, 2-styrenated phenol And any compound of 3-styrenated phenol.
- n is 2
- the compound represented by the general formula (1) is 1,2-distyrenated phenol, 1,3-distyrenated phenol, 1,4-distyrenated phenol, 1,5-distyrenated phenol
- the compound represented by the general formula (1) is 1,2,3-tristyrenated phenol, 1,2,4-tristyrenated phenol, 1,2,5-tristyrenated phenol Or 1,3,4-tristyrenated phenol, 1,3,5-tristyrenated phenol, or 2,3,4-tristyrenated phenol.
- the compound (A) represented by the general formula (1) may be a single compound or a mixture of two or more kinds, but a compound having n of 2 because the synergetic effect of the antioxidant property is high and the solubility in the base oil is high.
- the amine antioxidant (B) used in the antioxidant composition of the present invention may be any known amine antioxidant, for example, 1-naphthylamine, phenyl-1- Naphthylamine-based antioxidants such as naphthylamine, p-octylphenyl-1-naphthylamine, p-nonylphenyl-1-naphthylamine, p-dodecylphenyl-1-naphthylamine, phenyl-2-naphthylamine; N, N'-diisopropyl-p -Phenylenediamine, N, N'-diisobutyl-p-phenylenediamine, N, N'-diphenyl-p-phenylenediamine, N, N'-di- ⁇ -naphthyl-p-phenylenediamine, N-phenyl-N ' -Isopropyl-
- R 1 and R 2 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 18 carbon atoms.
- R 3 and R 4 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 18 carbon atoms).
- each of R 1 to R 4 independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 18 carbon atoms.
- the aliphatic hydrocarbon group having 1 to 18 carbon atoms for example, methyl group, ethyl group, propyl group, branched propyl group, butyl group, branched butyl group, hexyl group, branched hexyl group, pentyl group, branched pentyl group, Heptyl, branched heptyl, octyl, branched octyl, 2-ethylhexyl, nonyl, branched nonyl, decyl, branched decyl, dodecyl, branched dodecyl, tridecyl, branched tridecyl, tetradecyl, Alkyl groups such as branched tetradecy
- the phenolic antioxidant (C) used in the antioxidant composition of the present invention is any known phenolic antioxidant except the compound (A) represented by the above general formula (1). It may be an antioxidant, for example, 2,6-di-tert-butylphenol (hereinafter, tert-butyl is abbreviated as t-butyl), 2,6-di-tert-butyl-p-cresol, 2,6 -Di-tert-butyl-4-methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,4-dimethyl-6-tert-butylphenol, 4,4'-methylenebis (2,6- Di-t-butylphenol), 4,4'-bis (2,6-di-t-butylphenol), 4,4'-bis (2-methyl-6-t-butylphenol), 2,2'-methylenebis ( 4-methyl-6-t Butylphenol), 2,2'-methylenebis (4-ethyl-6-t-butylphenol), 4,
- R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
- R 7 is a hydrocarbon having 1 to 20 carbon atoms which may contain an ester group
- m represents a number of 1 to 4, provided that any one of R 5 and R 6 must be an alkyl group having 1 to 4 carbon atoms.
- R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
- the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, a branched propyl group, a butyl group, a branched butyl group, and a tertiary butyl group.
- R 5 and R 6 do not simultaneously become a hydrogen atom, and either one or both of them must be an alkyl group having 1 to 4 carbon atoms, but both have 1 to 4 carbon atoms because of their good antioxidant properties.
- Alkyl groups are preferred, and both are more preferably tertiary butyl.
- R 7 represents a hydrocarbon group having 1 to 20 carbon atoms which may contain an ester group, and m represents a number of 1 to 4.
- m represents a number of 1 to 4.
- ester group As group containing ester group, the following general formula (5) is mentioned, for example: -R 8 COOR 9 (5) (Wherein, R 8 represents an alkylene group having 1 to 6 carbon atoms, and R 9 represents a hydrocarbon group having 1 to 20 carbon atoms.)
- R 8 examples include methylene, ethylene, propylene, butylene, pentylene and hexylene. Among these, ethylene is preferable because the raw material can be easily obtained.
- R 9 is, for example, methyl, ethyl, propyl, branched propyl, butyl, branched butyl, hexyl, branched hexyl, pentyl, branched pentyl, heptyl, branched heptyl, octyl Group, branched octyl group, 2-ethylhexyl group, nonyl group, branched nonyl group, decyl group, branched decyl group, dodecyl group, branched dodecyl group, tridecyl group, branched tridecyl group, tetradecyl group, branched tetradecyl group, pentadecyl group, branched Alkyl groups such as pentadecyl, hexadecyl, branched pentadecenyl, heptadecyl, branched
- R 7 is, for example, methylene group, ethylene group, propylene group, butylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, nonylene group, decylene group, dodecylene group, tetradecylene group, And alkylene groups such as hexadecylene group and octadecylene group.
- group containing an ester group include the following general formula (6):
- R 10 , R 11 and R 12 each independently represent an alkylene group having 1 to 16 carbon atoms
- R 10 , R 11 and R 12 are, for example, methylene group, ethylene group, propylene group, butylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, nonylene group, decylene group, dodecylene group, tetradecylene group, Hexadecylene group etc. are mentioned.
- Examples of R 7 when m is 3 include the following general formula (7) and general formula (8), and examples of R 7 when m is 4 include, for example, the following general formula (9) And the general formula (10).
- R 13 to R 15 each independently represent an alkylene group having 1 to 6 carbon atoms
- each of R 16 to R 18 independently represents an alkylene group having 1 to 6 carbon atoms).
- R 19 to R 22 each independently represent an alkylene group having 1 to 6 carbon atoms
- R 23 represents an alkylene group having 1 to 6 carbon atoms
- R 13 to R 23 in the compounds of the general formulas (7) to (10) include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group and a hexylene group.
- ethylene is preferable because the raw material can be easily obtained.
- composition which added amine system antioxidant (B) and / or phenol system antioxidant (C) to the compound (A) represented by the said General formula (1) improves antioxidant performance by a synergistic effect .
- This synergistic effect may be any compounding ratio regardless of the compounding ratio of each component, but since a higher effect can be expected, the compound (A), the amine antioxidant (B) and / or the phenol
- the ratio to the antioxidant (C) is preferably 30/70 to 99/1 (mass ratio), more preferably 50/50 to 97/3, 70/30 to 95/5.
- the lubricating oil composition of the present invention is a composition comprising a base oil and the antioxidant composition of the present invention as essential components.
- the base oil any base oil which can be used as a base oil of lubricating oil can be used, for example, poly- ⁇ -olefin, ethylene- ⁇ -olefin copolymer, polybutene, alkylbenzene, alkyl naphthalene, poly Synthetic oils such as alkylene glycols, polyphenyl ethers, alkyl substituted diphenyl ethers, polyol esters, dibasic acid esters, carbonic esters, GTL (Gas to Liquids), etc .; paraffinic mineral oils, naphthenic mineral oils, or purified mineral oils obtained by purifying these It can be used.
- Each of these base oils may be used alone or as a mixture.
- a base oil having a viscosity index of 100 or more because the application range as a lubricating oil is wide and the color tone of the base oil is nearly colorless and transparent, and the viscosity index is 100 or more More preferred is the use of poly- ⁇ -olefins, GTL, refined mineral oils.
- greases are also included in the lubricating oil composition of the present invention.
- thickeners which are essential components of greases include soap-based or complex soap-based thickeners, organic non-soap-based thickeners, inorganic non-soap-based thickeners, and mixtures thereof.
- soap thickeners examples include lauric acid, myristic acid, palmitic acid, stearic acid, 12-hydroxystearic acid, arachic acid, behenic acid, zomarinic acid, oleic acid, linoleic acid, linolenic acid, licinoleic acid
- a soap in which a higher fatty acid and a base such as aluminum, barium, calcium, lithium, sodium and potassium are reacted, or the above fatty acid and a base are further reacted with acetic acid, benzoic acid, sebacic acid, azelaic acid, phosphoric acid, boric acid and the like
- Complex soap thickeners and the like Complex soap thickeners and the like.
- organic non-soap thickeners examples include terephthalemate thickeners, urea thickeners, fluorine-based polymers such as polytetrafluoroethylene and fluorinated ethylene-propylene copolymers.
- urea thickeners include monourea compounds in which monoisocyanate and monoamine are reacted, diurea compounds in which diisocyanate and monoamine are reacted, ureaurethane compounds in which diisocyanate, monoamine and monool are reacted, diisocyanate and diamine Examples include tetraurea compounds in which monoisocyanate is reacted.
- inorganic non-soap thickeners examples include montmorillonite, bentonite, silica airgel, boron nitride and the like.
- the blending amount of these thickeners is not particularly limited, but it may be blended so as to be usually 3 to 40% by mass, preferably 5 to 20% by mass, with respect to the total amount of the grease composition.
- the compounding quantity of the antioxidant composition of this invention added to the lubricating oil composition of this invention is not specifically limited, 0.01-10 mass% is preferable with respect to lubricating oil composition whole quantity, 0.05-5 is preferable. % By mass is more preferable, and 0.1 to 3% by mass is even more preferable. If the amount is less than 0.01% by mass, a sufficient antioxidant effect may not be obtained, and if it exceeds 10% by mass, the effect corresponding to the addition amount can not be obtained, or the product stability of the lubricating oil composition It can get worse.
- the lubricating oil composition of the present invention does not reject the addition of known lubricating oil additives, and depending on the purpose of use, a friction modifier, an antiwear agent, an extreme pressure agent, an oiliness improver, a detergent, A dispersant, a viscosity index improver, a pour point depressant, a rust inhibitor, a corrosion inhibitor, an antifoamer, etc. may be added in the range which does not impair the effect of the present invention.
- the friction modifier examples include organomolybdenum compounds such as sulfurized oxymolybdenum dithiocarbamate and sulfurized oxymolybdenum dithiophosphate.
- the preferable blending amount of these friction reducing agents is 30 to 2000 mass ppm, more preferably 50 to 1000 mass ppm in terms of molybdenum content with respect to the total amount of the lubricating oil composition.
- sulfurized oxymolybdenum dithiocarbamate is preferable to sulfurized oxymolybdenum dithiophosphate containing a phosphorus atom, and sulfurized oxymolybdenum dithiocarbamate having an alkyl group having 8 to 13 carbon atoms is more preferable.
- antiwear agent examples include compounds represented by the following general formula (11): [Wherein, A represents any one of the following general formulas (12) to (14), R 29 to R 36 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is 1 Represents a number of ⁇ 10. ]
- R 29 to R 36 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group and a propyl group. Among these, a hydrogen atom and a methyl group are preferable because of their good anti-wear performance.
- the preferred blending amount of these antiwear agents is 0.01 to 5% by mass, more preferably 0.1 to 3% by mass, based on the total amount of the lubricating oil composition.
- Extreme pressure agents include, for example, sulfur-based additives such as sulfurized fats and oils, olefin polysulfides, dibenzyl sulfide, etc .; monooctyl phosphate, tributyl phosphate, triphenyl phosphite, tributyl phosphite, thiophosphate, zinc dithiophosphate, etc. Phosphorus compounds; organic metal compounds such as metal thiophosphates, metal salts of thiocarbamates, metal salts of acidic phosphates, and the like.
- the preferable blending amount of these extreme pressure agents is 0.01 to 2% by mass, more preferably 0.05 to 1% by mass, based on the total amount of the lubricating oil composition.
- oiliness improver examples include higher alcohols such as oleyl alcohol and stearyl alcohol; fatty acids such as oleic acid and stearic acid; esters such as oleylglycerin ester, stearylglycerin ester and laurylglycerin ester; laurylamide and oleylamide And amides such as stearylamide; amines such as laurylamine, oleylamine and stearylamine; and ethers such as laurylglycerin ether and oleylglycerin ether.
- the preferred blending amount of these oil improvers is 0.1 to 5% by mass, more preferably 0.2 to 3% by mass, based on the total amount of the lubricating oil composition.
- Detergents include, for example, calcium, magnesium, sulfonates such as barium, phenates, salicylates, phosphates and their overbased salts.
- overbased salts are preferable, and among the overbased salts, those having a TBN (total basic number) of 30 to 500 mg KOH / g are more preferable.
- TBN total basic number
- the preferred blending amount of these detergents is 0.5 to 10% by mass, more preferably 1 to 8% by mass, based on the total amount of the lubricating oil composition.
- dispersant examples include succinimide, succinate ester, benzylamine or boron-modified products thereof, to which an alkyl group or alkenyl group having a weight-average molecular weight of about 500 to 3,000 is added.
- the preferable blending amount of these dispersants is 0.5 to 10% by mass, more preferably 1 to 8% by mass, based on the total amount of the lubricating oil composition.
- a viscosity index improver for example, poly (C1-18) alkyl methacrylate, (C1-18) alkyl acrylate / (C1-18) alkyl methacrylate copolymer, diethylaminoethyl methacrylate / (C1-18) alkyl methacrylate copolymer weight Combination, ethylene / (C1-18) alkyl methacrylate copolymer, polyisobutylene, polyalkylstyrene, ethylene / propylene copolymer, styrene / maleic ester copolymer, styrene / isoprene hydrogenated copolymer, etc. .
- a dispersion type or multifunctional viscosity index improver to which dispersion performance is imparted may be used.
- the weight average molecular weight is about 10,000 to 1,500,000, preferably about 30,000 to 1,000,000.
- the preferable blending amount of these viscosity index improvers is 0.1 to 20% by mass with respect to the total amount of the lubricating oil composition. More preferably, it is 0.3 to 15% by mass.
- pour point depressants examples include polyalkyl methacrylates, polyalkyl acrylates, polyalkyl styrenes, polyvinyl acetates and the like, and the weight average molecular weight is about 1000 to 100,000, preferably about 3,000 to 80,000. .
- the preferred blending amount of these pour point depressants is 0.005 to 3% by mass, more preferably 0.01 to 2% by mass, based on the total amount of the lubricating oil composition.
- Antirust agents include, for example, sodium nitrite, oxidized paraffin wax calcium salt, oxidized paraffin wax magnesium salt, tallow fatty acid alkali metal salt, alkaline earth metal salt or amine salt, alkenyl succinic acid or alkenyl succinic acid half ester (alkenyl The molecular weight of the group is about 100 to 300), sorbitan monoester, nonylphenol ethoxylate, lanolin fatty acid calcium salt and the like.
- the preferred blending amount of these rust inhibitors is 0.01 to 3% by mass, more preferably 0.02 to 2% by mass, based on the total amount of the lubricating oil composition.
- corrosion inhibitor examples include benzotriazole, benzoimidazole, benzothiazole, tetraalkylthiuram disulfide and the like.
- the preferred blending amount of these corrosion inhibitors is 0.01 to 3% by mass, more preferably 0.02 to 2% by mass, based on the total amount of the lubricating oil composition.
- antifoaming agent examples include polydimethyl silicone, trifluoropropyl methyl silicone, colloidal silica, polyalkyl acrylate, polyalkyl methacrylate, alcohol ethoxy / propoxylate, fatty acid ethoxy / propoxylate, sorbitan partial fatty acid ester and the like.
- the preferred blending amount of these antifoaming agents is 0.001 to 0.1% by mass, more preferably 0.001 to 0.01% by mass, based on the total amount of the lubricating oil composition.
- the lubricating oil composition of the present invention is used in general lubricating oil applications such as engine oil, gear oil, turbine oil, hydraulic oil, flame retardant hydraulic fluid, refrigerator oil, compressor oil, vacuum pump oil, bearing oil, insulation Any oil, sliding surface oil, rock drill oil, metal processing oil, plastic processing oil, heat-treated oil, grease, etc. can be used in any application, but it is an engine oil that requires high antioxidant performance, It is preferably used for applications such as turbine oil, metalworking oil, grease and the like.
- Example> A mixture of 90% by mass of 2,4-distyrenated phenol, 5% by mass of 2-monostyreneated phenol, and 5% by mass of 2,4,6-tristyrenated phenol
- A-2 2-monostyrenated phenol
- A-3 2,4,6-tristyrenated phenol
- C-1 Branched octyl 3- (4-hydroxy-3,5-di-t-butylphenyl) propionate
- C-2 3- (4-hydroxy-3,5-di-t- Butylphenyl) propionic acid linear octadecyl
- Samples (D-1) and (D-2) are solvents for comparison with compound (A). Further, all of the test samples 1 to 11 were transparent liquids at normal temperature.
- ⁇ Antioxidant test> It carried out based on the method of JIS K-2514. Specifically, put 50g of sample, 5g of water and 3m of copper wire with a diameter of 1.6mm as a catalyst into a compact pressure cylinder with a pressure gauge and put it in a cylinder after sealing. Inject oxygen until the pressure of 620 kPa. The cylinder is rotated at 100 rotations per minute in a thermostat of 150 ° C. while maintaining an angle of 30 ° C. Initially, the pressure in the cylinder increases as temperature is applied, but when oxidative degradation starts, oxygen is absorbed and the pressure in the cylinder decreases.
- the pressure was measured over time, and the time from when the pressure was maximum to when it decreased to 175 kPa was determined, which was defined as the induction period of oxidative degradation. The longer the induction period, the better the antioxidation performance of the sample.
- what added the test sample created according to the said mixing table so that it might become 0.5 mass% to the following base oil was used for the sample.
- tests of single samples used for comparison were also conducted. Also in the test of the sample itself, one obtained by adding the sample to 0.5% by mass to the following base oil 1 or 2 was used as the sample.
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Abstract
Description
(式中、R8は炭素数1~6のアルキレン基を表し、R9は炭素数1~20の炭化水素基を表す。)
<サンプル>
(A-1):2,4-ジスチレン化フェノール90質量%、2-モノスチレ
ン化フェノール5質量%、2,4,6-トリスチレン化フェノ
ール5質量%の混合物
(A-2):2-モノスチレン化フェノール
(A-3):2,4,6-トリスチレン化フェノール
ロピオン酸分岐オクチル
(C-2):3-(4-ヒドロキシ-3,5-ジ―t-ブチルフェニル)プ
ロピオン酸直鎖オクタデシル
エステル
(D-2):ノニルフェノール
上記のサンプルを表1の配合に従って配合し、得られた試験サンプルを酸化防止性試験及び安定性試験に使用した。なお、サンプルの(D-1)及び(D-2)は、化合物(A)と比較するための溶剤である。また、試験サンプル1~11はいずれも常温で透明液体であった。
JIS K-2514の方法に準拠して行った。具体的には、圧力計を備えた容量100mlの耐圧ボンベの中に、試料50g、水5g、及び触媒として直径1.6mmの銅線3mをコンパクトに丸めたものを入れ、密封した後ボンベ内の圧力が620kPaになるまで酸素を圧入する。このボンベを150℃の恒温槽内で、30℃の角度を保持したまま毎分100回転で回転させる。最初、ボンベ内の圧力は温度がかかることで増加していくが、酸化劣化が始まると酸素を吸収してボンベ内の圧力は低下する。圧力を経時で測定し、圧力が最高になったときから175kPaに低下するまでの時間を求め、これを酸化劣化の誘導期間とした。誘導期間が長いほど酸化防止性能が良好な試料である。なお、試料は上記配合表に従って作成した試験サンプルを下記の基油に0.5質量%になるように添加したものを用いた。また、比較のために使用したサンプル単体の試験も行った。サンプル単体の試験も、サンプルを下記の基油1または2に0.5質量%になるように添加したものを試料として用いた。
℃)、粘度指数=126の鉱物油系基油
基油2:動粘度4.0mm2/秒(100℃)、18.4mm2/秒(40℃)
、粘度指数=119のポリαオレフィン
Claims (5)
- 化合物(A)と、アミン系酸化防止剤(B)及びフェノール系酸化防止剤(C)との割合が、30/70~99/1(重量比)であることを特徴とする請求項1に記載の酸化防止剤組成物。
- アミン系酸化防止剤(B)が下記の一般式(2)又は一般式(3)、及びフェノール系酸化防止剤(C)が下記の一般式(4)で表される化合物であることを特徴とする請求項1または2に記載の酸化防止剤組成物:
- 請求項1ないし3のいずれかに記載の酸化防止剤組成物と、基油とを含有することを特徴とする潤滑油組成物。
- 酸化防止剤組成物の配合量が潤滑油組成物全量に対して0.01~10質量%であることを特徴とする請求項4に記載の潤滑油組成物。
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KR1020137005638A KR101810276B1 (ko) | 2010-09-14 | 2011-08-26 | 산화방지제 조성물 및 그것을 함유하는 윤활유 조성물 |
US13/822,494 US9382498B2 (en) | 2010-09-14 | 2011-08-26 | Antioxidant composition and lubricating oil composition containing same |
EP11824962.2A EP2617802B1 (en) | 2010-09-14 | 2011-08-26 | Antioxidant composition, and lubricating oil composition containing same |
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WO2014176294A2 (en) * | 2013-04-22 | 2014-10-30 | Ethox Chemicals, Llc | Additives to resin compositions for improved impact strength and flexibility |
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WO2016143807A1 (ja) * | 2015-03-09 | 2016-09-15 | Jxエネルギー株式会社 | グリース組成物 |
KR101659318B1 (ko) * | 2015-11-24 | 2016-09-23 | 주식회사 루브캠코리아 | 윤활 그리스 조성물 및 이의 제조 방법 |
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CA3029147A1 (en) | 2016-06-29 | 2018-01-04 | Adeka Corporation | Internal combustion engine lubricating oil composition |
CN109065210A (zh) * | 2018-07-24 | 2018-12-21 | 晶锋集团股份有限公司 | 一种强效导电抗氧化的电缆及其制备方法 |
CN109280499A (zh) * | 2018-09-10 | 2019-01-29 | 天长市永泰密封材料有限公司 | 一种强效抗氧化的环氧粘合剂及其制备方法 |
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JP2008101144A (ja) | 2006-10-20 | 2008-05-01 | Japan Energy Corp | 長寿命省燃費型エンジン油組成物 |
WO2009009293A1 (en) * | 2007-07-06 | 2009-01-15 | Chemtura Corporation | Lubricant compositions stabilized with styrenated phenolic antioxidant |
JP2009197135A (ja) | 2008-02-21 | 2009-09-03 | Adeka Corp | 潤滑油用酸化防止剤組成物及びそれを含有する潤滑油組成物 |
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WO2014174106A1 (en) * | 2013-04-26 | 2014-10-30 | Shell Internationale Research Maatschappij B.V. | Vacuum pump oil |
Also Published As
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US20130184190A1 (en) | 2013-07-18 |
JP2012062348A (ja) | 2012-03-29 |
JP5721983B2 (ja) | 2015-05-20 |
EP2617802A1 (en) | 2013-07-24 |
EP2617802A4 (en) | 2015-04-22 |
KR101810276B1 (ko) | 2017-12-19 |
CN103097502A (zh) | 2013-05-08 |
CN103097502B (zh) | 2015-07-22 |
KR20130108544A (ko) | 2013-10-04 |
EP2617802B1 (en) | 2019-09-18 |
US9382498B2 (en) | 2016-07-05 |
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