WO2014007376A1 - Composé succinimide, additif pour huile lubrifiante et composition d'huile lubrifiante - Google Patents

Composé succinimide, additif pour huile lubrifiante et composition d'huile lubrifiante Download PDF

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WO2014007376A1
WO2014007376A1 PCT/JP2013/068526 JP2013068526W WO2014007376A1 WO 2014007376 A1 WO2014007376 A1 WO 2014007376A1 JP 2013068526 W JP2013068526 W JP 2013068526W WO 2014007376 A1 WO2014007376 A1 WO 2014007376A1
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lubricating oil
succinimide compound
general formula
succinimide
molecular weight
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PCT/JP2013/068526
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English (en)
Japanese (ja)
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一生 田川
紀子 阿部
美帆 遠藤
龍一 上野
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Ｊｘ日鉱日石エネルギー株式会社
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Publication of WO2014007376A1 publication Critical patent/WO2014007376A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/56—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • 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
    • C10M2215/064—Di- and triaryl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbasedsulfonic acid salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/045—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for continuous variable transmission [CVT]
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines

Definitions

  • the present invention relates to a novel succinimide compound, and a lubricating oil additive and lubricating oil composition containing the compound.
  • Succinimide compounds are used in the field of lubricating oils for internal combustion engines, such as gasoline engine oils and diesel engine oils, as ashless dispersants that disperse the insoluble matter produced in the oils.
  • succinimide compounds are used as friction modifiers for increasing frictional force in the field of drive system lubricants such as automatic transmissions.
  • a succinimide compound obtained by reaction of a succinic anhydride substituted with a high molecular weight alkenyl or alkyl group and a polyalkylene polyamine is known (Patent Document 1 below).
  • a method for producing a substituted succinimide a method in which a maleimide compound and a silicon enolate are reacted is known (see Patent Document 4 below).
  • the present invention relates to a novel succinimide compound useful for applications such as an ashless dispersant in a lubricating oil for internal combustion engines, a friction modifier in a drive system lubricating oil, and a lubricating oil additive and a lubricating oil composition containing the compound.
  • the purpose is to provide.
  • the present invention provides a succinimide compound represented by the following general formula (1).
  • R 1 represents an alkyl group having a number average molecular weight of 500 or more and less than 5000 or an alkenyl group having a number average molecular weight of 500 or more and less than 5000, and two R 1 in the same molecule may be the same or different from each other.
  • n shows the integer of 3-20.
  • this invention provides the succinimide compound obtained by reaction with the compound represented by the following general formula (2), and the compound represented by the following general formula (3).
  • R 1 represents an alkyl group having a number average molecular weight of 500 or more and less than 5000 or an alkenyl group having a number average molecular weight of 500 or more and less than 5000.
  • n shows the integer of 3-20.
  • succinimide compound of the present invention has very superior characteristics compared to conventional succinimide compounds, it is suitable for use in ashless dispersants in internal combustion engine lubricants, friction modifiers in drive device lubricants, etc. Useful for applications.
  • the succinimide compound of the present invention is superior in the effect of improving the friction characteristics as compared with the conventional succinimide compound, so that the frictional force inside the automatic transmission is efficiently converted to the driving force.
  • a high coefficient of friction can be achieved, and fuel efficiency can be improved.
  • the present invention also provides a lubricating oil additive containing the succinimide compound of the present invention.
  • the present invention also provides a lubricating oil composition containing a lubricating base oil and the succinimide compound of the present invention.
  • the present invention also provides a lubricating oil composition for a continuously variable transmission, comprising a lubricating base oil and the succinimide compound of the present invention.
  • the lubricating oil composition of the present invention preferably further contains a phosphorus compound.
  • a novel succinimide compound useful for applications such as an ashless dispersant in an internal combustion engine lubricating oil, a friction modifier in a drive system lubricating oil, and a lubricating oil additive and lubricating oil containing the compound It becomes possible to provide a composition.
  • FIG. 1 is an IR chart of a succinimide compound obtained in Example 1.
  • the succinimide compound according to the first embodiment of the present invention has a structure represented by the following formula (1).
  • R 1 in the general formula (1) is preferably a polybutenyl group or a polyisobutenyl group.
  • the number average molecular weight is 500 or more and less than 5000, preferably 700 to 4000, more preferably 800 to 3500.
  • n is an integer of 3 to 20, preferably an integer of 3 to 16, more preferably an integer of 3 to 10.
  • impurities increase, the reactivity tends to decrease, and the insoluble content in the base oil tends to increase.
  • the upper limit is exceeded, the solubility in the base oil tends to decrease. It is in.
  • the succinimide compound represented by the general formula (1) may be used as it is without being boronated (that is, as a non-boronated succinimide compound) or may be used as a boronated succinimide compound. Further, a boronated succinimide compound and a non-borated succinimide compound may be used in combination.
  • the boronated succinimide compound is obtained by reacting the boron-containing compound with the succinimide compound represented by the general formula (1) at a temperature of usually 50 to 250 ° C., preferably 100 to 200 ° C. Can do.
  • the boron-containing compound include boron oxide, boron halide, boric acid, boric anhydride, and boric acid ester. These boron-containing compounds may be used alone or in combination of two or more.
  • the succinimide compound according to the second embodiment of the present invention is a succinimide compound obtained by a reaction between a compound represented by the following general formula (2) and a compound represented by the following general formula (3). is there.
  • R 1 represents an alkyl group having a number average molecular weight of 500 or more and less than 5000 or an alkenyl group having a number average molecular weight of 500 or more and less than 5000.
  • n shows the integer of 3-20.
  • R 1 in the general formula (2) and n in the general formula (3) each have the same definition as R 1 and n in the general formula (1). These preferable modes are also the same as those in the case of the general formula (1), and redundant description is omitted here.
  • the succinimide compound represented by the general formula (1) is usually obtained as a main product. Moreover, since there are a plurality of reaction sites of the compound represented by the general formula (3), 1 equivalent of the compound represented by the general formula (3) in the reaction product depending on the charging ratio (molar ratio) of the raw material compounds. There may be a by-product represented by the following general formula (4) in which 2 equivalents or more of the compound represented by the general formula (2) are reacted.
  • the above-mentioned by-product may be removed from the reaction product, and only the succinimide compound represented by the general formula (1) may be used as a lubricating oil additive, or the general formula (1 A mixture of the succinimide compound represented by (2) and the above-mentioned by-product may be used as a lubricating oil additive.
  • R 1 represents an alkyl group having a number average molecular weight of 500 or more and less than 5000 or an alkenyl group having a number average molecular weight of 500 or more and less than 5000
  • R 2 represents —NH 2 or the following general formula (5):
  • R 1 represents an alkyl group having a number average molecular weight of 500 or more and less than 5000 or an alkenyl group having a number average molecular weight of 500 or more and less than 5000.
  • N represents an integer of 3 or more and 20 or less, and at least one of n R 2 is a group represented by the general formula (5).
  • the succinimide represented by the general formula (1) in the reaction product is appropriately selected by appropriately selecting the charging ratio of the compound represented by the general formula (2) and the compound represented by the general formula (3). It is possible to adjust the proportion of the compound. From the point that the succinimide compound represented by the general formula (1) can be obtained more reliably, the charging ratio of both is the general formula (3) with respect to 1 mol of the compound represented by the general formula (2). Is preferably 1 to 2 mol, more preferably 1 to 1.8 mol, still more preferably 1.1 to 1.6 mol, and particularly preferably 1.2 to 1.5 mol.
  • reaction conditions for the compound represented by the general formula (2) and the compound represented by the general formula (3) are not particularly limited, but the reaction temperature is 145 to 180 ° C, preferably 155 to 175 ° C, and the reaction time Is 1 to 8, preferably 2 to 6 hours.
  • a reaction solvent can be used as necessary, and the solvent is preferably a solvent that dissolves the compound represented by the general formula (2) and the compound represented by the general formula (3). Examples thereof include ethanol, toluene, and xylenes.
  • the succinimide compound according to this embodiment may be used as it is without being boronated (that is, as a non-boronated succinimide compound) or may be used as a boronated succinimide compound. Further, a boronated succinimide compound and a non-borated succinimide compound may be used in combination.
  • a boronated succinimide compound can be obtained by reacting a boron-containing compound with a succinimide compound represented by the formula (1) at a temperature of usually 50 to 250 ° C., preferably 100 to 200 ° C. it can.
  • the boron-containing compound include boron oxide, boron halide, boric acid, boric anhydride, and boric acid ester. These boron-containing compounds may be used alone or in combination of two or more.
  • the lubricating oil additive according to the present embodiment contains the succinimide compound according to the first embodiment or the second embodiment.
  • the lubricating oil additive may be composed only of the succinimide compound according to the first embodiment or the second embodiment, and the succinimide compound according to the first embodiment or the second embodiment and other It may be a mixture with an additive.
  • the lubricating oil additive may further contain a diluent for dissolving the additive.
  • the succinimide compound according to the first embodiment and the second embodiment is excellent in compatibility with various additives used in the lubricating oil field. Therefore, when the lubricating oil additive according to the present embodiment is a mixture of the succinimide compound according to the first embodiment or the second embodiment and other additives, the types of other additives used in combination are particularly The type of the other additive used in combination with the succinimide compound according to the first embodiment or the second embodiment and the blending amount of both are appropriately selected according to the use and purpose of the lubricant additive. be able to. Specific examples of other additives used in combination will be described later.
  • the lubricating oil composition according to the fourth embodiment of the present invention contains a lubricating base oil and the succinimide compound according to the first embodiment or the second embodiment.
  • the aspect containing the lubricating oil base oil and the lubricating oil additive which concerns on the said 3rd Embodiment is included by the said lubricating oil composition.
  • the lubricating base oil is not particularly limited, and both mineral oil and synthetic oil can be used.
  • Various conventionally known oils can be used as the mineral oil, and examples thereof include paraffin-based mineral oil, intermediate-based mineral oil, and naphthene-based mineral oil.
  • light neutral oil, intermediate neutral oil, heavy neutral oil, bright stock, etc. by solvent refining or hydrogen refining can be mentioned.
  • GTL base oil obtained by isomerizing wax may be used, and the effect increases as the degree of purification increases.
  • various conventionally known oils can be used as well.
  • poly ⁇ -olefin including ⁇ -olefin copolymer
  • polybutene polyol ester
  • dibasic acid ester phosphate ester
  • polyphenyl ether alkylbenzene
  • alkylnaphthalene polyoxyalkylene glycol
  • neopentyl glycol silicone Oil, trimethylolpropane, pentaerythritol, hindered ester and the like can be used.
  • lubricating base oils can be used singly or in combination of two or more, and may be used in combination of mineral oil and synthetic oil.
  • the kinematic viscosity of the lubricating base oil can be appropriately selected according to the use and purpose of the lubricating oil composition.
  • the kinematic viscosity at 100 ° C. of the lubricating base oil is preferably 1 to 30 mm 2 / s, more preferably 2 to 20 mm 2 / s. More preferably, it is 3 to 10 mm 2 / s.
  • the kinematic viscosity at 100 ° C. is in the above range, friction at sliding parts such as gear bearings and clutches of the automatic transmission can be sufficiently reduced and the low temperature characteristics are also good.
  • the kinematic viscosity at 100 ° C. exceeds 30 mm 2 / s, the fuel efficiency deteriorates and the low-temperature viscosity tends to be too high. Further, if the kinematic viscosity at 100 ° C. is less than 1 mm 2 / s, the lubrication performance is lowered such as an increase in wear amount in sliding parts such as gear bearings and clutches of the automatic transmission, and the evaporating property is increased, resulting in lubrication. Oil consumption may increase.
  • the% CA of the lubricating base oil is preferably 20 or less, more preferably 10 or less, from the viewpoint of low temperature characteristics.
  • the content of the succinimide compound represented by the formula (1) is preferably 0.01 to 30% by mass from the viewpoint that the additive effect can be effectively exhibited. More preferably, it is 0.05 to 20% by mass, and still more preferably 0.1 to 10% by mass.
  • the lubricating oil composition according to the present embodiment may further contain additives other than the succinimide compound according to the first embodiment or the second embodiment, as necessary, for the purpose of further improving the performance. it can.
  • additives include ashless dispersants and / or friction modifiers other than the succinimide compounds represented by formula (1), metal detergents, viscosity index improvers, extreme pressure additives, antioxidants, corrosion An inhibitor, an antifoamer, a coloring agent, etc. are mentioned. These additives can be used individually by 1 type or in combination of 2 or more types.
  • Ashless dispersants and / or friction modifiers other than succinimide compounds according to the first embodiment or the second embodiment include fatty acid esters, fatty acid amides, phosphate esters, phosphite esters, thiophosphate esters, and the like.
  • Solid lubricants such as phosphorus compounds, organomolybdenum compounds such as MoDTP, MoDTC, organozinc compounds such as ZnDTP, organoboron compounds such as alkyl mercaptoylborate, graphite, molybdenum disulfide, antimony sulfide, boron compounds, polytetrafluoroethylene System friction modifiers and the like.
  • organoboron compounds such as alkyl mercaptoylborate, graphite, molybdenum disulfide, antimony sulfide, boron compounds, polytetrafluoroethylene System friction modifiers and the like.
  • phosphorus compounds are preferable.
  • antioxidants examples include amine-based antioxidants such as alkylated diphenylamine, phenyl- ⁇ -naphthylamine and alkylated- ⁇ -naphthylamine, 2,6-di-t-butyl-4-methylphenol, 4,4 ′ And phenolic antioxidants such as -methylenebis (2,6-di-t-butylphenol).
  • the content of the antioxidant is usually 0.05 to 5% by mass based on the total amount of the lubricating oil composition.
  • metallic detergents include calcium sulfonate, magnesium sulfonate, barium sulfonate, calcium salicylate, magnesium salicylate, calcium phenate, barium phenate, and the like.
  • the amount is usually 0.1 to 10% by mass based on the total amount of the oil composition.
  • viscosity index improver examples include polymethacrylate, polyisobutene, ethylene-propylene copolymer, and styrene-butadiene hydrogenated copolymer.
  • the content of the viscosity index improver is usually 0.5 to 35% by mass based on the total amount of the lubricating oil composition.
  • the use of the lubricating oil composition according to the present embodiment is not particularly limited, and can be used in a wide range of fields such as a lubricating oil for internal combustion engines and a drive system lubricating oil.
  • a lubricating oil for internal combustion engines and a drive system lubricating oil since the lubricating oil composition according to the present embodiment contains a succinimide compound represented by the lubrication formula (1), it has a higher coefficient of static friction (high wet friction material) than a conventional succinimide compound. Torque capacity) and can be used as an automatic transmission oil or a continuously variable transmission oil. Further, it can be used as a lubricating oil for construction machines, agricultural machines, manual transmissions, two-wheeled gasoline engines, diesel engines, gas engines, shock absorber oils, etc., equipped with transmissions having wet clutches and wet brakes.
  • Example 1 Synthesis of Succinimide Compound Ia Assembling the synthesizer, weighed 69.90 g of the compound represented by the general formula (2), R 1 is a polyisobutenyl group having a number average molecular weight of 1,000, into a 500 mL 4-necked flask, and the inside of the 4-necked flask was replaced with nitrogen. did.
  • 14.2 g of a compound represented by the general formula (3) where n is 3 was weighed into a screw tube, and 50 ml of xylene was added thereto to obtain a solution. This solution was transferred to a dropping funnel attached to a four-necked flask.
  • Example 2 Synthesis of Succinimide Compound Ib Assembling the synthesizer, weighed 69.90 g of the compound represented by the general formula (2), R 1 is a polyisobutenyl group having a number average molecular weight of 2,300, into a 500 mL 4-neck flask, and the inside of the 4-neck flask was replaced with nitrogen. did.
  • the obtained product is represented by the general formula (1), R 1 is a polyisobutenyl group having a number average molecular weight of 2,300, and n is 3 (hereinafter, “ Succinimide compound Ib ”)).
  • Examples 3 to 8, Comparative Examples 2 to 4; Preparation and Evaluation Test of Lubricating Oil Composition mineral oil of 10 SAE fractions (100 ° C. kinematic viscosity 4.1 mm 2 / s) as a lubricant base oil, succinimide compound Ia or Ib, and additions shown below, respectively A lubricating oil composition having the composition shown in Table 1 was prepared using the agent.
  • a mineral oil of SAE 10 fraction 100 ° C. kinematic viscosity 4.1 mm 2 / s
  • succinimide compound II succinimide compound II
  • additives shown below were used, respectively.
  • a lubricating oil composition having the composition shown in 2 was prepared. Further, in Comparative Example 4, a lubricating oil having the composition shown in Table 2 using a mineral oil of SAE 10 fraction (100 ° C. kinematic viscosity 4.1 mm 2 / s) as a lubricating base oil and the additives shown below. A composition was prepared. Polymethacrylate: average molecular weight 20,000 Amine-based antioxidant: diphenylamine tricresyl phosphanote calcium sulfonate: 300TBN Ashless oil-based agent: glycerol monooleate
  • the succinimide compound, lubricating oil additive and lubricating oil composition of the present invention can be used in a wide range of lubricating oil fields, and are particularly suitable as automatic transmission oils and continuously variable transmission oils that require a high coefficient of static friction. is there.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
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  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Composé succinimide représenté par la formule générale (1). Dans la formule (1), R1 représente un groupe alkyle ayant une masse moléculaire moyenne en nombre d'au moins 500 et de moins de 5000 ou un groupe alcényle ayant une masse moléculaire moyenne en nombre d'au moins 500 et de moins de 5000, les deux R1 d'une même molécule pouvant être identiques ou différents, et n étant un entier de 3 à 20.
PCT/JP2013/068526 2012-07-05 2013-07-05 Composé succinimide, additif pour huile lubrifiante et composition d'huile lubrifiante WO2014007376A1 (fr)

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JP2004509186A (ja) * 2000-09-12 2004-03-25 ビーエーエスエフ　アクチェンゲゼルシャフト ３０〜７００個の炭素原子を有するポリアルキレンを連続的にヒドロホルミル化する方法
JP2011214176A (ja) * 2010-03-31 2011-10-27 Sanyo Chem Ind Ltd 繊維用集束剤
JP2011219377A (ja) * 2010-04-05 2011-11-04 Jx Nippon Oil & Energy Corp コハク酸イミド化合物、潤滑油添加剤及び潤滑油組成物
JP2011219533A (ja) * 2010-04-05 2011-11-04 Jx Nippon Oil & Energy Corp コハク酸イミド化合物、潤滑油添加剤及び潤滑油組成物

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JP2001505593A (ja) * 1996-09-20 2001-04-24 ビーエーエスエフ アクチェンゲゼルシャフト ヒドロホルミル化法
JP2004509186A (ja) * 2000-09-12 2004-03-25 ビーエーエスエフ　アクチェンゲゼルシャフト ３０〜７００個の炭素原子を有するポリアルキレンを連続的にヒドロホルミル化する方法
JP2011214176A (ja) * 2010-03-31 2011-10-27 Sanyo Chem Ind Ltd 繊維用集束剤
JP2011219377A (ja) * 2010-04-05 2011-11-04 Jx Nippon Oil & Energy Corp コハク酸イミド化合物、潤滑油添加剤及び潤滑油組成物
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