WO2014007379A1 - 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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WO2014007379A1
WO2014007379A1 PCT/JP2013/068534 JP2013068534W WO2014007379A1 WO 2014007379 A1 WO2014007379 A1 WO 2014007379A1 JP 2013068534 W JP2013068534 W JP 2013068534W WO 2014007379 A1 WO2014007379 A1 WO 2014007379A1
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general formula
succinimide
compound
compound represented
formula
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PCT/JP2013/068534
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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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Priority claimed from JP2012151837A external-priority patent/JP5952660B2/ja
Priority claimed from JP2012151836A external-priority patent/JP5889134B2/ja
Priority claimed from JP2012151830A external-priority patent/JP5952659B2/ja
Priority claimed from JP2012151839A external-priority patent/JP5876779B2/ja
Application filed by Ｊｘ日鉱日石エネルギー株式会社 filed Critical Ｊｘ日鉱日石エネルギー株式会社
Publication of WO2014007379A1 publication Critical patent/WO2014007379A1/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
    • C08F8/02—Alkylation
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • 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
    • 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 having a structure represented by the following general formula (1), (2), (3) or (4).
  • 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.
  • the present invention also provides a succinimide compound obtained by a reaction of a compound represented by the following general formula (5) and a compound represented by the following formula (6), (7) or (8).
  • 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.
  • this invention provides the succinimide compound obtained by reaction of the compound represented by following General formula (9), and the compound represented by following formula (6).
  • 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.
  • 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.
  • FIG. 4 is a diagram showing an IR chart of a succinimide compound obtained in Example 3.
  • FIG. 6 is a diagram showing an IR chart of a succinimide compound obtained in Example 5.
  • FIG. 6 is a diagram showing an IR chart of a succinimide compound obtained in Example 7.
  • the succinimide compound according to the first embodiment of the present invention has a structure represented by the following 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.
  • 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.
  • 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 reaction between a compound represented by the following general formula (5) and a compound represented by the following formula (6) (also referred to as “styrene oxide”). It is a succinimide compound obtained by this.
  • 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 1 in the general formula (5) represent the same definition as R 1 in general formula (1).
  • the preferred embodiment of R 1 is also the same as in the case of R 1 in the general formula (1), and redundant explanation is omitted here.
  • 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 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 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.
  • 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.
  • the succinimide compound represented by the general formula (1) in the reaction product is selected by appropriately selecting the charging ratio of the compound represented by the general formula (5) and the compound represented by the formula (6). It is possible to adjust the ratio of. From the point that the succinimide compound represented by the general formula (1) can be obtained more reliably, the charging ratio of both is expressed by the formula (6) with respect to 1 mol of the compound represented by the general formula (5).
  • the compound represented 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 (5) and the compound represented by the formula (6) are not particularly limited, but the reaction temperature is 90 to 130 ° C., preferably 100 to 120 ° C., and the reaction time is 2 to 8, preferably 3 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 (5) and the compound represented by the formula (6), specifically an organic solvent. Yes, ethanol, toluene, xylenes and the like can be exemplified.
  • 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 succinimide compound according to the third embodiment of the present invention has a structure represented by the following formula (2).
  • 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 1 in the general formula (2) 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.
  • the succinimide compound represented by the general formula (2) 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 (2) 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 fourth embodiment of the present invention is a compound represented by the following general formula (5) and a compound represented by the following formula (7) (also referred to as “Trans-stilbene oxide”). It is a succinimide compound obtained by reaction of this.
  • 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 1 in the general formula (5) represent the same definition as R 1 in the general formula (2).
  • the preferred embodiment of R 1 is also the same as in the case of R 1 in the general formula (2), and redundant description is omitted here.
  • the succinimide compound represented by the above general formula (2) is usually obtained as a main product.
  • the compound represented by the formula (7) reacted in the reaction product with 2 equivalents with respect to 1 equivalent of the compound represented by the 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.
  • 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.
  • the above-mentioned by-product may be removed from the reaction product, and only the succinimide compound represented by the general formula (2) may be used as a lubricating oil additive, or the general formula (2 A mixture of the succinimide compound represented by (2) and the above-mentioned by-product may be used as a lubricating oil additive.
  • the succinimide compound represented by the general formula (2) in the reaction product is selected by appropriately selecting the charging ratio of the compound represented by the general formula (5) and the compound represented by the formula (6). It is possible to adjust the ratio of. From the point that the succinimide compound represented by the general formula (2) can be obtained more reliably, the charging ratio of both is represented by the formula (7) with respect to 1 mol of the compound represented by the general formula (5).
  • the compound represented 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 (5) and the compound represented by the formula (7) are not particularly limited, but the reaction temperature is 90 to 130 ° C., preferably 100 to 120 ° C., and the reaction time is 4 to 8, preferably 5 to 6 hours.
  • a reaction solvent can be used as necessary.
  • the solvent a solvent that dissolves the compound represented by the general formula (5) and the compound represented by the formula (7) is preferable. Yes, ethanol, toluene, xylenes and the like can be exemplified.
  • 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.
  • the boronated succinimide compound can be obtained by reacting a boron-containing compound with a succinimide compound represented by the formula (2) at a temperature of usually 50 to 250 ° C., preferably 100 to 200 ° C. it can.
  • a 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 fifth embodiment of the present invention has a structure 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.
  • R 1 in the general formula (3) 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.
  • the succinimide compound represented by the general formula (3) 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 a boron-containing compound with a succinimide compound represented by the general formula (3) at a temperature of usually 50 to 250 ° C., preferably 100 to 200 ° C. Can do.
  • a 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 sixth embodiment of the present invention is obtained by a reaction between a compound represented by the following general formula (5) and a compound represented by the following formula (8) (also referred to as “glycidol”). It is a succinimide compound obtained.
  • 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 1 in the general formula (5) represent the same definition as R 1 in the general formula (3).
  • the preferred embodiment of R 1 is also the same as in the case of R 1 in the general formula (3), and redundant explanation is omitted here.
  • the succinimide compound represented by the general formula (3) is usually obtained as a main product. Further, depending on the charge ratio (molar ratio) of the raw material compounds, the following general reaction in which 2 equivalents of the compound represented by the formula (8) are reacted with 1 equivalent of the compound represented by the general formula (5) in the reaction product There may be a by-product represented by formula (16).
  • 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 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.
  • the above-mentioned by-product may be removed from the reaction product, and only the succinimide compound represented by the general formula (3) may be used as a lubricating oil additive, or the general formula (3 A mixture of the succinimide compound represented by (2) and the above-mentioned by-product may be used as a lubricating oil additive.
  • the succinimide compound represented by the general formula (3) in the reaction product is appropriately selected by appropriately selecting the charging ratio of the compound represented by the general formula (5) and the compound represented by the formula (8). It is possible to adjust the ratio of. From the point that the succinimide compound represented by the general formula (3) can be obtained more reliably, the charging ratio of both is expressed by the formula (8) with respect to 1 mol of the compound represented by the general formula (5).
  • the compound represented 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 (5) and the compound represented by the formula (8) are not particularly limited, but the reaction temperature is 90 to 130 ° C., preferably 100 to 120 ° C., and the reaction time is 2 to 8, preferably 3 to 6 hours.
  • a reaction solvent can be used if necessary, and the solvent is preferably a solvent that dissolves the compound represented by the general formula (5) and the compound represented by the formula (8), specifically an organic solvent. Yes, ethanol, toluene, xylenes and the like can be exemplified.
  • 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.
  • the boronated succinimide compound can be obtained by reacting a boron-containing compound with a succinimide compound represented by the formula (3) at a temperature of usually 50 to 250 ° C., preferably 100 to 200 ° C. it can.
  • a 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 seventh embodiment of the present invention has a structure represented by the following general formula (4).
  • 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 1 in the general formula (4) 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.
  • the succinimide compound represented by the general formula (4) 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 a boron-containing compound with a succinimide compound represented by the general formula (4) at a temperature of usually 50 to 250 ° C., preferably 100 to 200 ° C. Can do.
  • a 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 eighth embodiment of the present invention is a reaction between a compound represented by the following general formula (9) and a compound represented by the following formula (6) (also referred to as “styrene oxide”). It is a succinimide compound obtained by this.
  • R 1 in the general formula (9) shows the same definition as R 1 in the general formula (4).
  • the preferred embodiment of R 1 is also the same as in the case of R 1 in the general formula (4), and redundant explanation is omitted here.
  • the ratio of the succinimide compound represented by the general formula (4) in the reaction product by appropriately selecting the charging ratio of the compound represented by the general formula (9) and the compound represented by the formula (6) Can be adjusted. From the point that the succinimide compound represented by the general formula (4) can be obtained more reliably, the charging ratio of both is represented by the formula (6) with respect to 1 mol of the compound represented by the general formula (9).
  • the compound represented 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 (9) and the compound represented by the formula (6) are not particularly limited, but the reaction temperature is 90 to 130 ° C, preferably 100 to 120 ° C, and the reaction time is 2 to 8, preferably 3 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 (9) and the compound represented by the formula (6). Yes, ethanol, toluene, xylenes and the like can be exemplified.
  • 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.
  • the boronated succinimide compound can be obtained by reacting a boron-containing compound with a succinimide compound represented by the formula (4) at a temperature of usually 50 to 250 ° C., preferably 100 to 200 ° C. it can.
  • a 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 ninth embodiment of the present invention contains at least one selected from the succinimide compounds shown in the first to eighth embodiments.
  • the lubricating oil additive may be composed only of the succinimide compound according to the first embodiment to the eighth embodiment.
  • the succinimide compound according to the first embodiment to the eighth 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 compounds according to the first to eighth embodiments are excellent in compatibility with various additives used in the lubricating oil field. Therefore, when the lubricating oil additive according to this embodiment is a mixture of the succinimide compound according to the first to eighth embodiments and other additives, the types of other additives used in combination are particularly Without limitation, the types of other additives used in combination with the succinimide compounds according to the first to eighth embodiments and the blending amounts of both are appropriately selected according to the use and purpose of the lubricating oil additive. be able to. Specific examples of other additives used in combination will be described later.
  • the lubricating oil composition according to the tenth embodiment of the present invention contains a lubricating base oil and at least one selected from the succinimide compounds shown in the first to eighth embodiments.
  • the aspect containing the lubricating base oil and the lubricating oil additive which concerns on the said 9th 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 compounds shown in the first to eighth embodiments has the effect of addition. From the standpoint of effective display, it is preferably 0.01 to 30% by mass, more preferably 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 compounds according to the first to eighth embodiments, if 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 the general formulas (1) to (4), metal detergents, viscosity index improvers, extreme pressure additives, Antioxidants, corrosion inhibitors, antifoaming agents, colorants and the like can be 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 to eighth embodiments 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, etc.
  • System friction modifiers and the like Among these, phosphorus compounds are preferable.
  • the content of the ashless dispersant and / or the friction modifier is usually 0.1 to 10% by mass based on the total amount of the lubricating oil composition.
  • 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.
  • the lubricating oil composition according to this embodiment contains at least one selected from succinimide compounds represented by the general formulas (1) to (4), it is compared with conventional succinimide compounds.
  • a high static friction coefficient high wet friction material torque capacity
  • 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
  • a compound represented by the general formula (5) and having R 1 of a polyisobutenyl group having a number average molecular weight of 1,000 was weighed, and a synthesizer was assembled. To this, 100 ml of toluene was added and stirred to dissolve.
  • 2.25 g of styrene oxide (compound represented by formula (6)) was weighed into a screw tube, and 15 ml of dehydrated ethanol was added to obtain a solution.
  • Example 2 Synthesis of Succinimide Compound Ib
  • 50.1 g of a compound represented by the general formula (5) and R 1 being a polyisobutenyl group having a number average molecular weight of 2,300 was weighed, and a synthesis apparatus was assembled. To this, 100 ml of toluene was added and stirred to dissolve.
  • 0.98 g of styrene oxide (compound represented by formula (6)) was weighed into a screw tube, and 15 ml of dehydrated ethanol was added to obtain a solution.
  • Example 3 Synthesis of Succinimide Compound Ic
  • a compound represented by the general formula (5) and R 1 being a polyisobutenyl group having a number average molecular weight of 1,000 was weighed, and a synthesizer was assembled. To this, 100 ml of toluene was added and stirred to dissolve.
  • 2.10 g of Trans-stilbene oxide (compound represented by formula (7)) was weighed into a screw tube, and 100 ml of toluene was added to obtain a solution.
  • Example 4 Synthesis of Succinimide Compound Id
  • 29.92 g of the compound represented by the general formula (5) and R 1 having a polyisobutenyl group having a number average molecular weight of 2,300 was weighed, and a synthesizer was assembled. To this, 100 ml of toluene was added and stirred to dissolve.
  • 0.90 g of Trans-stilbene oxide (compound represented by the formula (7)) was weighed into a screw tube, and 100 ml of toluene was added to obtain a solution.
  • Example 5 Synthesis of succinimide compound Ie
  • 20.00 g of a compound represented by the general formula (5) and having R 1 of polyisobutenyl group having a number average molecular weight of 1,000 was weighed, and a synthesizer was assembled. To this, 100 ml of toluene was added and stirred to dissolve. On the other hand, 0.56 g of glycidol (compound represented by formula (8)) was weighed into a screw tube, and 15 ml of dehydrated ethanol was added to obtain a solution.
  • Example 6 Synthesis of succinimide compound If
  • a compound represented by the general formula (5) and R 1 being a polyisobutenyl group having a number average molecular weight of 2,300 was weighed, and a synthesizer was assembled. To this, 100 ml of toluene was added and stirred to dissolve.
  • 0.56 g of glycidol (compound represented by formula (8)) was weighed into a screw tube, and 15 ml of dehydrated ethanol was added to obtain a solution.
  • Example 7 Synthesis of succinimide compound Ig]
  • Compound (succinimide compound in which polyisobutenyl group and tris 2-aminoethyl group are introduced) represented by general formula (9) and R 1 is a polyisobutenyl group having a number average molecular weight of 1000 in a 300 mL four-necked flask 27 .57g was weighed and a synthesizer was assembled. To this, 100 ml of toluene was added and stirred to dissolve. On the other hand, 1.25 g of styrene oxide (compound represented by formula (6)) was weighed into a screw tube, and 15 ml of dehydrated ethanol was added to obtain a solution.
  • styrene oxide compound represented by formula (6)
  • Example 8 Synthesis of succinimide compound Ih]
  • Compound (succinimide compound in which polyisobutenyl group and tris 2-aminoethyl group are introduced) represented by general formula (9) and R 1 is a polyisobutenyl group having a number average molecular weight of 2300 in a 300 mL 4-neck flask 28 .6 g was weighed and a synthesizer was assembled. To this, 100 ml of toluene was added and stirred to dissolve. On the other hand, 0.55 g of styrene oxide (compound represented by formula (6)) was weighed into a screw tube, and 15 ml of dehydrated ethanol was added to obtain a solution.
  • styrene oxide compound represented by formula (6)
  • Example 9 to 32 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
  • succinimide compounds Ia to Ih succinimide compounds Ia to Ih
  • additions shown below Lubricating oil compositions having the compositions shown in Tables 1 to 4 were prepared using the agents.
  • a mineral oil of SAE 10 fraction 100 ° C. kinematic viscosity 4.1 mm 2 / s
  • succinimide compound II succinimide compound II, and the 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 5 using mineral oil of 10 SAE fractions (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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Abstract

Composé succinimide ayant la structure représentée 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.
PCT/JP2013/068534 2012-07-05 2013-07-05 Composé succinimide, additif pour huile lubrifiante et composition d'huile lubrifiante WO2014007379A1 (fr)

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JP2012-151836 2012-07-05
JP2012151837A JP5952660B2 (ja) 2012-07-05 2012-07-05 コハク酸イミド化合物、潤滑油添加剤及び潤滑油組成物
JP2012-151839 2012-07-05
JP2012151836A JP5889134B2 (ja) 2012-07-05 2012-07-05 コハク酸イミド化合物、潤滑油添加剤及び潤滑油組成物
JP2012-151837 2012-07-05
JP2012151830A JP5952659B2 (ja) 2012-07-05 2012-07-05 コハク酸イミド化合物、潤滑油添加剤及び潤滑油組成物
JP2012151839A JP5876779B2 (ja) 2012-07-05 2012-07-05 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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Cited By (1)

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Publication number Priority date Publication date Assignee Title
EP3536766A1 (fr) * 2014-05-30 2019-09-11 The Lubrizol Corporation Sels d'ammonium quaternaires fonctionnalisés par des agents de quaternisation époxyde

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JP2008094841A (ja) * 2006-10-10 2008-04-24 Afton Chemical Corp 分枝スクシニミド系分散剤化合物および前記化合物の製造方法
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
JP2011219537A (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
JP2012513495A (ja) * 2008-12-22 2012-06-14 シェブロン・オロナイト・カンパニー・エルエルシー 潤滑油添加剤組成物およびその製造方法

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Publication number Priority date Publication date Assignee Title
JP2008094841A (ja) * 2006-10-10 2008-04-24 Afton Chemical Corp 分枝スクシニミド系分散剤化合物および前記化合物の製造方法
JP2012513495A (ja) * 2008-12-22 2012-06-14 シェブロン・オロナイト・カンパニー・エルエルシー 潤滑油添加剤組成物およびその製造方法
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
JP2011219537A (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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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3536766A1 (fr) * 2014-05-30 2019-09-11 The Lubrizol Corporation Sels d'ammonium quaternaires fonctionnalisés par des agents de quaternisation époxyde

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