EP1019466A1 - Polyalkylensuccinimid-zusammensetzung für brennkraftmaschinen - Google Patents

Polyalkylensuccinimid-zusammensetzung für brennkraftmaschinen

Info

Publication number
EP1019466A1
EP1019466A1 EP98949715A EP98949715A EP1019466A1 EP 1019466 A1 EP1019466 A1 EP 1019466A1 EP 98949715 A EP98949715 A EP 98949715A EP 98949715 A EP98949715 A EP 98949715A EP 1019466 A1 EP1019466 A1 EP 1019466A1
Authority
EP
European Patent Office
Prior art keywords
succinimide
polyalkylene
polyalkylene succinimide
treated
polybutene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98949715A
Other languages
English (en)
French (fr)
Inventor
Morikuni Nakazato
Satoshi Hirano
William W. Willis, Jr.
Robert L. Freerks
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chevron Oronite Japan Ltd
Chevron Phillips Chemical Co LP
Original Assignee
Oronite Japan Ltd
Chevron Chemical Co LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP28466697A external-priority patent/JPH11106776A/ja
Priority claimed from US09/015,801 external-priority patent/US5861363A/en
Application filed by Oronite Japan Ltd, Chevron Chemical Co LLC filed Critical Oronite Japan Ltd
Publication of EP1019466A1 publication Critical patent/EP1019466A1/de
Withdrawn legal-status Critical Current

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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
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    • C08F8/00—Chemical modification by after-treatment
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
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    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
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    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/09—Complexes with metals
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
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    • C10N2040/251—Alcohol-fuelled engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline 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
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    • C10N2040/28—Rotary engines
    • C—CHEMISTRY; METALLURGY
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    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • the present invention relates to novel compositions comprising mixtures of post-treated derivatives of polyalkylene succinimides.
  • the invention relates to methods of preparing these compositions and their uses as dispersants in lubricating oils.
  • the invention relates to concentrates and lubricating oil compositions.
  • Lubricating oil compositions for internal combustion engines generally contain a variety of additives to reduce or control deposits, wear, corrosion, etc.
  • the present invention is concerned with compositions useful as dispersants in lubricating oil compositions.
  • dispersants function to control sludge, carbon, and varnish produced primarily by the incomplete combustion of the fuel, or impurities in the fuel, or impurities in the base oil used in the lubricating oil composition. Dispersants also control viscosity increase due to the presence of soot in diesel engine lubricating oils.
  • lubricating oil dispersants One of the most effective classes of lubricating oil dispersants is polyalkylene succinimides.
  • succinimides have also been found to provide fluid-modifying properties, or a so-called viscosity index credit, in lubricating oil compositions. That produces a reduction in the amount of viscosity index improver which would be otherwise have to be used.
  • Polyalkylene succinimides are generally prepared by the reaction of the corresponding polyalkylene succinic anhydride with a polyalkyl polyamine.
  • Polyalkylene succinic anhydrides are generally prepared by a number of well- known processes. For example, there is a well-known thermal process (see, e.g., U.S. Patent No. 3,361 ,673), an equally well-known chlorination process (see, e.g., U.S. Patent No. 3,172,892), a combination of the thermal and chlorination processes (see, e.g., U.S. Patent No. 3,912,764), and free radical processes (see, e.g., U.S. Patent Nos.
  • compositions include one-to-one monomeric adducts (see, e.g., U.S. Patent Nos. 3,219,666 and 3,381 ,022), as well as "multiply adducted" products, adducts having alkenyl-derived substituents adducted with at least 1.3 succinic groups per alkenyl-derived substituent (see, e.g., U.S. Patent No. 4,234,435).
  • U.S. Patent Nos. 3,361 ,673 and 3,018,250 describe the reaction of an alkenyl- or alkyl-substituted succinic anhydride with a polyamine to form alkenyl or alkyl succinimide lubricating oil dispersants and/or detergent additives.
  • alkenyl or alkyl succinimides may be modified by reaction with a cyclic or linear carbonate or chloroformate such that one or more of the nitrogens of the polyamine moiety is substituted with a hydrocarbyl oxycarbonyl, a hydroxyhydrocarbyl oxycarbonyl, or a hydroxy poly(oxyalkylene) oxycarbonyl.
  • These modified succinimides are described as exhibiting improved dispersancy and/or detergency in lubricating oils.
  • U.S. Patent No. 4,747,965 discloses modified succinimides similar to those disclosed in U.S. Patent No. 4,612,132, except that the modified succinimides are described as being derived from succinimides having an average of greater than 1.0 succinic groups per long chain alkenyl substituent.
  • U.S. Patent No. 4,234,435 teaches a preferred polyalkene-derived substituent group with a Mn in the range of 1 ,500 to 3,200.
  • Mn Mn in the range of 1 ,500 to 3,200.
  • an especially preferred Mn range is 1 ,700 to 2,400.
  • a variety of post-treatments for improving various properties of alkenyl succinimides are known to the art, a number of which are described in U.S. Patent No. 5,241 ,003.
  • Example 2 of U.S. Patent No. 5,266,186 discloses the preparation of dispersants by reacting certain polyisobutenyl-succinic anhydride adducts (see footnote 2 of Table 2) with ethylenediamine, followed by reaction with a maleic anhydride/alpha-olefin copolymer.
  • the patent teaches that, by functioning as an iron sulfide dispersant, the product is useful to inhibit sludge deposits in refinery processing equipment caused by the heat treatment of hydrocarbon feed stocks.
  • U.S. Patent No. 5,112,507 discloses a polymeric ladder type polymeric succinimide dispersant in which each side of the ladder is a long chain alkyl or alkenyl, generally having at least about 30 carbon atoms, preferably at least about 50 carbon atoms.
  • the dispersant is described as having improved hydrolytic stability and shear stress stability, produced by the reaction of certain maleic anhydride-olefin copolymers with certain polyamines.
  • the polymer may be post-treated with a variety of post-treatments, and describes procedures for post-treating the polymer with cyclic carbonates, linear mono- or polycarbonates; boron compounds (e.g., boric acid), and fluorophosphoric acid and ammonia salts thereof.
  • boron compounds e.g., boric acid
  • U.S. Patent Nos. 5,334,321 and 5,356,552 disclose certain cyclic carbonate post-treated alkenyl or alkylsuccinimides having improved fluorocarbon elastomer compatibility, which are preferably prepared by the reaction of the corresponding substituted succinic anhydride with a polyamine having at least four nitrogen atoms per mole. Both of these patents disclose the possibility of borating certain cyclic carbonate post-treated alkenyl or alkylsuccinimides.
  • U.S. Patent Nos. 5,334,321 discloses that higher molecular weight alkenyl or alkylsuccinimides give better detergency than the corresponding lower molecular weight alkenyl or alkylsuccinimides.
  • U.S. Patent No. 5,716,912 discloses polyalkylene succinimides prepared by reacting, under reactive conditions, a mixture of a polybutene succinic acid derivative, an unsaturated acidic reagent copolymer of an unsaturated acidic reagent and an olefin, and a polyamine, then treating those succinimides with cyclic carbonates, linear mono- or polycarbonates, or a boron compound.
  • the present invention provides a lubricating oil composition with improved detergency.
  • the lubricating oil composition of the present invention comprises:
  • the number average molecular weight of the polyalkylenes from which the carbonate-treated polyalkylene succinimide additive is derived is at least 300 greater than the number average molecular weight of the polyalkylenes from which the boron-treated polyalkylene succinimide additive is derived.
  • the lubricating oil composition preferably further contains from 0.02% to 5% of a molybdenum compound.
  • the content of the molybdenum compound in the lubricating oil composition preferably is in an amount of 10 to 2,500 ppm in terms of molybdenum element.
  • the lubricating oil composition preferably further contains at least one of the following: from 1 % to 20% of a viscosity index improver and from 0.1 % to 5% of an oxidation inhibitor selected from the group consisting of phenol compounds and amine compounds.
  • the carbonate-treated polyalkylene succinimide additive is a reaction product of a high molecular weight alkenyl- or alkyl-substituted succinic anhydride and a polyalkylene polyamine having an average of 4 to 10 nitrogen atoms per mole and is post-treated with a cyclic carbonate.
  • the polyalkylene group of the carbonate-treated polyalkylene succinimide additive is derived from a polybutene having a molecular weight of from 1 ,000 to 2,700, more preferably from 1 ,900 to 2,700.
  • the polyalkylene group of the borated polyalkylene succinimide additive is derived from a polybutene having a molecular weight of from 1 ,000 to 2,700.
  • the carbonate-treated polyalkylene succinimide additive and the borated polyalkylene succinimide additive are contained in a total amount of 1 % to 15%, and the carbonate-treated polyalkylene succinimide additive and the borated polyalkylene succinimide additive are contained in a weight ratio of 2:8 to 8:2.
  • the present invention also provides a polyalkylene succinimide composition that improves the soot dispersancy properties of a lubricating oil composition.
  • This polyalkylene succinimide composition comprises borated and carbonated polyalkylene succinimides derived from different molecular weight polyalkylenes.
  • the polyalkylene succinimide composition comprises from 10% to 50% of a boron-treated polyalkylene succinimide and from 50% to 90% of a carbonate- treated polyalkylene succinimide.
  • This polyalkylene succinimide composition produces superior soot dispersancy to either the boron-treated polyalkylene succinimide or the carbonate-treated polyalkylene succinimide when used alone.
  • the boron-treated polyalkylene succinimide is derived from polyalkylenes having a lower molecular weight than the polyalkylenes from which the carbonate-treated polyalkylene succinimide is derived. This difference in molecular weight is at least 300, preferably from 800 to 1 ,000.
  • the boron-treated polyalkylene succinimide is a polybutene succinimide derived from polybutenes having a molecular weight of from 1 ,200 to 1 ,400 and the carbonate-treated polyalkylene succinimide is a polybutene succinimide derived from polybutenes having a molecular weight of from 2,000 to 2,400.
  • the carbonate-treated polybutene succinimide is prepared by reacting, under reactive conditions, a mixture of a polybutene succinic acid derivative, an unsaturated acidic reagent copolymer of an unsaturated acidic reagent and an olefin, and a polyamine.
  • soot dispersancy of a lubricating oil in internal combustion engine applications can be improved by adding to that lubricating oil an effective amount of the polyalkylene succinimide composition of the present invention.
  • the invention provides a lubricating oil composition comprises a major amount of a base oil of lubricating viscosity and the polyalkylene succinimide composition of the present invention.
  • the invention also provides a concentrate comprising the polyalkylene succinimide composition of the present invention, an organic diluent, and preferably at least one other additive.
  • the organic diluent constitutes from 1% to 20% of the concentrate, and the polyalkylene succinimide composition constitutes from 5% to 80% of the concentrate.
  • the present invention involves a lubricating oil composition
  • a lubricating oil composition comprising a major portion of a base oil, specific amounts of a cyclic carbonate-treated polyalkylene succinimide additive, a borated polyalkylene succinimide additive, a metal-containing detergent, and a zinc dialkyldithiophosphate.
  • the present invention involves a polyalkylene succinimide composition that comprises a mixture of borated and carbonated polyalkylene succinimides derived from different number average molecular weight polyalkylenes.
  • succinimide is understood in the art to include many of the amide, imide, etc. species that are also formed by the reaction of a succinic anhydride with an amine.
  • Polyalkylene succinimides are disclosed in numerous references and are well known in the art. Certain fundamental types of succinimides and related materials encompassed by the term of art "succinimide” are taught in U.S. Patent Nos. 2,992,708; 3,018,291 ; 3,024,237; 3,100,673; 3,219,666; 3,172,892; and 3,272,746, the disclosures of which are hereby incorporated by reference in their entirety for all purposes.
  • polyalkylene succinic acid derivative refers to a structure having the formula:
  • R is a polyalkylene
  • L and M are independently selected from the group consisting of -OH, -Cl, -0-, lower alkyl or taken together are -O- to form a polyalkylene succinic anhydride group.
  • unsaturated acidic reagent refers to maleic or fumaric reactants of the general formula:
  • X and X' are the same or different, provided that at least one of X and X' is a group that is capable of reacting to esterify alcohols, form amides, or amine salts with ammonia or amines, form metal salts with reactive metals or basically reacting metal compounds, and otherwise function as acylating agents.
  • X and/or X' is -OH, -O-hydrocarbyl, -OM + where M + represents one equivalent of a metal, ammonium or amine cation, -NH 2 , -Cl, -Br, and taken together X and X' can be -O- so as to form an anhydride.
  • X and X' are such that both carboxylic functions can enter into acylation reactions.
  • Maleic anhydride is a preferred unsaturated acidic reactant.
  • Other suitable unsaturated acidic reactants include electron-deficient olefins such as monophenyl maleic anhydride; monomethyl, dimethyl, monochloro, monobromo, monofluoro, dichloro and difluoro maleic anhydride; N-phenyl maleimide and other substituted maleimides; isomaleimides; fumaric acid, maleic acid, alkyl hydrogen maleates and fumarates, dialkyi fumarates and maleates, fumaronilic acids and maleanic acids; and maleonitrile, and fumaronitrile.
  • the base oil of lubricating viscosity used in such compositions may be mineral oils or synthetic oils of viscosity suitable for use in the crankcase of an internal combustion engine.
  • the base oil preferably has a dynamic viscosity of 2 to 50 mm 2 /s at 100°C and may be derived from synthetic or natural sources.
  • Mineral oils for use as the base oil in this invention include paraffinic, naphthenic, and other oils that are ordinarily used in lubricating oil compositions.
  • Synthetic oils include both hydrocarbon synthetic oils and synthetic esters.
  • Useful synthetic hydrocarbon oils include liquid polymers of alpha olefins having the proper viscosity.
  • the hydrogenated liquid oligomers of C ⁇ to C 12 alpha olefins such as 1-decene trimer.
  • alkyl benzenes of proper viscosity such as didodecyl benzene
  • useful synthetic esters include the esters of monocarboxylic acids and polycarboxylic acids, as well as monohydroxy alkanols and polyols. Typical examples are didodecyl adipate, pentaerythritol tetracaproate, di-2-ethylhexyl adipate, dilaurylsebacate, and the like.
  • Complex esters prepared from mixtures of mono- and dicarboxylic acids and mono- and dihydroxy alkanols can also be used. Blends of mineral oils with synthetic oils are also useful.
  • the polyalkylene succinimides of the lubricating oil composition of the present invention comprises from 0.5% to 15% of a carbonate-treated polyalkylene succinimide derived from a higher molecular weight polyalkylene and from 0.5% to 15% of a boron-treated polyalkylene succinimide derived from a lower molecular weight polyalkylene.
  • the combination of the two succinimides produces superior detergency and soot dispersancy to either the boron-treated polyalkylene succinimide or the carbonate-treated polyalkylene succinimide when used alone.
  • the advantages of the boron-treated polyalkylene succinimide in TBN contribution and prevention of bearing corrosion are also preserved.
  • the individual polyalkylene succinimides of the present invention can be prepared by conventional processes, such as disclosed in U.S. Patent No. 2,992,708; 3,018,250; 3,018,291 ; 3,024,237; 3,100,673; 3,172,892; 3,219,666 3,272,746; 3,361 ,673; 3,381 ,022; 3,912,764; 4,234,435; 4,612,132; 4,747,965 5,112,507; 5,241 ,003; 5,266,186; 5,286,799; 5,319,030; 5,334,321 ; 5,356,552 5,716,912, the disclosures of which are all hereby incorporated by reference in their entirety for all purposes.
  • the cyclic carbonate-treated polyalkylene succinimide additive is an ashless dispersant and can be prepared by reaction of a high molecular weight alkenyl- or alkyl-substituted succinic anhydride and a polyalkylene polyamine having an average of 4 to 10 nitrogen atoms (preferably 5 to 7 nitrogen atoms) per mole and is post-treated with a cyclic carbonate.
  • the polyalkylene of the cyclic carbonate-treated polyalkylene succinimide additive is derived from polyalkylenes having a molecular weight of at least 1 ,000.
  • the carbonate-treated polyalkylene succinimide is a polybutene succinimide derived from polybutenes having a molecular weight of from 1 ,000 to 2,700, more preferably 1 ,900 to 2,700, and most preferably 2,000 to 2,400.
  • the polyalkylene of the cyclic carbonate-treated polyalkylene succinimide additive is prepared by reacting, under reactive conditions, a mixture of a polybutene succinic acid derivative, an unsaturated acidic reagent copolymer of an unsaturated acidic reagent and an olefin, and a polyamine, such as taught in U.S. Patent No. 5,716,912.
  • the borated polyalkylene succinimide additive is an ashless dispersant and can be prepared by reaction of a high molecular weight alkenyl- or alkyl- substituted succinic anhydride and a polyalkylene polyamine having an average of 4 to 10 nitrogen atoms (preferably 5 to 7 nitrogen atoms) per mole and is post-treated with a boric acid or boric acid compound.
  • the polyalkylene of the boron-treated polyalkylene succinimide additive is derived from polyalkylenes having a molecular weight of at least 1 ,000.
  • the boron-treated polyalkylene succinimide is derived from polybutenes having a molecular weight of from 1 ,000 to 2,700, more preferably 1 ,200 to 1 ,400, most preferably about 1 ,300.
  • the boron content in the borated polyalkylene succinimide additive preferably is in the range of 0.1% to 5%, more preferably 0.2% to 2%.
  • the cyclic carbonate-treated polyalkylene succinimide additive and the borated polyalkylene succinimide additive are preferably contained in a weight ratio of 2:8 to 8:2.
  • the cyclic carbonate-treated polyalkylene succinimide additive and the borated polyalkylene succinimide additive are preferably contained in the lubricating oil composition in a total amount of from 1% to 15%.
  • the lubricating oil composition of the invention can further contain other ashless dispersants such as other succinic imide dispersants, succinic acid ester dispersants, and benzylamine dispersants.
  • the polyalkylene succinimide composition of the present invention comprises from 10% to 50% of a boron-treated polyalkylene succinimide derived from a lower molecular weight polyalkylene and from 50% to 90% of a carbonate- treated polyalkylene succinimide derived from a higher molecular weight polyalkylene.
  • the polyalkylene succinimide composition of the present invention comprises from 20% to 40% of the boron-treated polyalkylene succinimide and from 60% to 80% of the carbonate-treated polyalkylene succinimide.
  • This polyalkylene succinimide composition produces superior soot dispersancy to either the boron-treated polyalkylene succinimide or the carbonate-treated polyalkylene succinimide when used alone.
  • the advantages of the boron-treated polyalkylene succinimide in TBN contribution and prevention of bearing corrosion are also preserved.
  • the individual polyalkylene succinimides used in the polyalkylene succinimide composition of the present invention can be prepared by conventional processes, such as disclosed in U.S. Patent No. 2,992,708; 3,018,250;
  • the polyalkylene succinimide composition can be prepared by physically mixing the boron-treated polyalkylene succinimide and the carbonate-treated polyalkylene succinimide.
  • the polyalkylene succinimide composition might have a slightly different composition than the initial mixture, because the components may interact.
  • the lubricating oil composition of the invention further contains from 0.5% to 20% of a metal-containing detergent.
  • a metal-containing detergent is metal phenates and metal sulfonates.
  • the metal phenate is an alkali metal salt or an alkaline earth metal salt of a sulfide of an alkylphenol having an alkyl group of approximately 8 to 30 carbon atoms.
  • the metal sulfonate is an alkali metal salt or an alkaline earth metal salt of a sulfonate of a mineral oil having a molecular weight of approximately 400 to 6,000 or an aromatic compound having an alkyl group.
  • Examples of the alkali metal salts and alkaline earth metal salts also include lithium salts, sodium salts, calcium salts, magnesium salts, and barium salts.
  • the metal phenate and the metal sulfonate can be employed singly or in combination.
  • metal-containing detergents such as an alkaline earth metal salicylate, an alkaline earth metal phosphonate, and an alkaline earth metal naphthenate can be employed in combination with the metal phenate and/or the metal sulfonate.
  • the metal-containing detergent can be a neutral type or an overbased type having a total base number (TBN) of 150 to 300, or more.
  • the lubricating oil composition of the invention further contains from 0.1 % to 3% of a zinc dialkyldithiophosphate (i.e., ZnDTP).
  • the zinc dialkyldithiophosphate preferably is zinc dialkyldithiophosphate containing an alkyl group of 3 to 18 carbon atoms.
  • the alkyl group of the zinc dialkyldithiophosphate is derived from a secondary alcohol of 3 to 18 carbon atoms or a mixture of the secondary alcohol and a primary alcohol.
  • additive components are examples of other components that can be favorably employed in the present invention. These examples of additives are provided to illustrate the present invention, but they are not intended to limit it:
  • the lubricating oil composition preferably may contain an oxidation inhibitor in an amount of 0.02% to 5%, more preferably 0.1% to 3%.
  • an oxidation inhibitor in an amount of 0.02% to 5%, more preferably 0.1% to 3%.
  • Diphenyl amine type oxidation inhibitor alkylated diphenyl amine, phenyl- ⁇ -naphthylamine, and alkylated- ⁇ -naphthylamine.
  • metal dithiocarbamate e.g., zinc dithiocarbamate
  • Nonionic polyoxyethylene surface active agents polyoxyethylene lauryl ether, polyoxyethylene higher alcohol ether, polyoxyethylene nonyl phenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene octyl stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene sorbitol monostearate, polyoxyethylene sorbitol mono-oleate, and polyethylene glycol monooleate.
  • the lubricating oil composition preferably contains a molybdenum compound in an amount of 0.02% to 5%, more preferably 0.1 to 3%.
  • the content of the molybdenum compound in the lubricating oil composition preferably is in an amount of 10 to 2,500 ppm in terms of molybdenum element.
  • Viscosity index improvers polymethacrylate type polymers, ethylene-propylene copolymers, styrene-isoprene copolymers, hydrated styrene-isoprene copolymers, polyisobutylene, and dispersant type viscosity index improvers.
  • the lubricating oil composition of the invention preferably may contain a viscosity index improver in an amount of 1 % to 20%.
  • Foam Inhibitors alkyl methacrylate polymers and dimethyl silicone polymers.
  • the lubricating oil composition of the present invention is useful for imparting improved detergency properties to an engine lubricating oil composition.
  • a lubricating oil composition comprises a major portion of a base oil, a cyclic carbonate-treated polyalkylene succinimide additive, a borated polyalkylene succinimide additive, a metal-containing detergent, and a zinc dialkyldithiophosphate.
  • a further aspect of the present invention involves a polyalkylene succinimide composition that comprises a mixture of borated and carbonated polyalkylene succinimides derived from different number average molecular weight polyalkylenes.
  • the polyalkylene succinimide compositions of the present invention are useful for imparting improved soot dispersancy properties to an engine lubricating oil composition.
  • a lubricating oil composition comprises a major part of base oil of lubricating viscosity and an effective amount of the polyalkylene succinimide composition of the present invention.
  • Adding an effective amount of the polyalkylene succinimide compositions of the present invention to a lubricating oil composition improves the soot dispersancy properties of that lubricating oil composition in automotive applications.
  • an engine lubricating oil composition would contain (a) a major amount of a base oil of lubricating viscosity; (b) from 0.5% to 15% of a carbonate-treated polyalkylene succinimide additive prepared by treating a first polyalkylene succinimide with a cyclic carbonate or a linear mono- or poly-carbonate under reactive conditions;
  • an engine lubricating oil composition is produced by blending a mixture of the above components.
  • the lubricating oil composition produced by that method might have a slightly different composition than the initial mixture, because the components may interact.
  • the components can be blended in any order and can be blended as combinations of components.
  • the polyalkylene succinimide composition can be blended with the other components before, during, and/or after the boron-treated polyalkylene succinimide and carbonate-treated polyalkylene succinimide are blended together.
  • Additive concentrates are also included within the scope of this invention.
  • the concentrates of this invention comprise an organic diluent and the compounds or compound mixtures of the present invention, preferably with at least one of the additives disclosed above.
  • the concentrates contain sufficient organic diluent to make them easy to handle during shipping and storage.
  • From 1% to 20% of the concentrate is organic diluent. From 5% to 80% of concentrate is the polyalkylene succinimide composition of the present invention. The remainder of the concentrate may comprise one or more of other additives discussed above.
  • Suitable organic diluents which can be used include for example, solvent refined 100N, i.e., Cit-Con 100N, and hydrotreated 100N, i.e., Chevron 100N, and the like.
  • the organic diluent preferably has a viscosity of about from 1 to 20 cSt at 100°C.
  • the components of the additive concentrate can be blended in any order and can be blended as combinations of components.
  • the polyalkylene succinimide composition can be blended with the other components before, during, and/or after the boron-treated polyalkylene succinimide and carbonate- treated polyalkylene succinimide are blended together.
  • Base oil of lubricating viscosity 40% Polyalkylene succinimide composition 30% Metal detergent 20% O Secondary alkyl zinc dithiophosphate 5% Molybdenum-containing anti-wear agent 5% Base oil of lubricating viscosity 40%
  • polybutene succinimides were prepared and post-treated by conventional means. The following percentages are based on the amount of active and inactive components, including any process oil or diluent oil used to form the polybutene succinimides.
  • the first polybutene succinimide was derived from 1 ,300 Mn polybutenes. This succinimide was formed by reacting a polybutene-substituted succinic acid derivative with a heavy polyamine (containing an average of approximately 6.5 nitrogen atoms per mole), then post-treating the resulting polybutene succinimide with boric acid.
  • a heavy polyamine containing an average of approximately 6.5 nitrogen atoms per mole
  • the second polybutene succinimide was derived from 2,200 Mn polybutenes. This was formed by reacting a polybutene-substituted succinic acid derivative with a heavy polyamine (containing an average of approximately 6.5 nitrogen atoms per mole), then post-treating the resulting polybutene succinimide with ethylene carbonate at a ratio of 2 moles of ethylene carbonate to 1 mole of basic nitrogen of the polybutene succinimide.
  • the third polybutene succinimide was derived from 2,200 Mn polybutenes. This was formed by reacting a mixture of a polybutene succinic acid derivative, an unsaturated acidic reagent copolymer of an unsaturated acidic reagent and an olefin, and a heavy polyamine (containing an average of approximately 6.5 nitrogen atoms per mole), then post-treating the resulting polybutene succinimide with ethylene carbonate at a ratio of 2 moles of ethylene carbonate to 1 mole of basic nitrogen of the polybutene succinimide.
  • a comparative carbonated polybutene succinimide was derived from 1 ,300 Mn polybutenes. This was formed by reacting a polybutene-substituted succinic acid derivative with a mixture of 80% heavy polyamine (containing an average of approximately 6.5 nitrogen atoms per mole) and 20% diethylene triamine, then post-treating the resulting polybutene succinimide with ethylene carbonate at a ratio of 2 moles of ethylene carbonate to 1 mole of basic nitrogen of the polybutene succinimide.
  • Polybutene Succinimides A, B and D were each blended separately into a SAE 15W-40 Screening Formulation (X) containing an effective amount of metallic detergent, zinc dithiophosphate, and a molybdenum based oxidation inhibitor.
  • a non-dispersant viscosity index modifier was chosen to eliminate any effects of viscosity index modifier on the test results.
  • Run Series III and IV differ in how the ethylene carbonated polybutene succinimide was formed prior to post-treatment with ethylene carbonate.
  • the bearing weight loss of blends of borated polybutene succinimides and carbonated polybutene succinimides of different molecular weight in a standard lubricating oil formulation (Z) were compared to the bearing weight loss of standard lubricating oil formulations having only carbonated polybutene succinimides.
  • the CRC L-38 test is a standard industry test that measures the corrosiveness of oil in terms of bearing weight loss. For the API CG-4 oil performance category, the limit is 43.7 milligrams maximum weight loss. The results are shown in the table below:
  • Run Series V shows the benefit to the mixed dispersant approach in passivating L-38 bearing weight loss.
  • Lubricating oil compositions of the invention (Run No. 14 to No. 17) and lubricating oil compositions for comparison (Run No. 18 to No. 21) were prepared according to the formulations set forth as shown below.
  • the lubricating oil compositions were adjusted to give a 10W-30 oil (SAE viscosity grade) by the addition of viscosity index improver.
  • SAE viscosity grade a 10W-30 oil
  • an effective amount of oxidation inhibitor, zinc dithiophosphate, and a dispersant viscosity index improver were added to the lubricating oil composition, including as other additives small amounts of anti-rust agent, friction modifier, anti-wear agent, metal-deactivating agent, demulsifier, anti-foaming agent, and pour point depressant.
  • Base oil of 150 neutral oil was used.
  • the first polybutene succinimide of this series was derived from 900 Mn polybutenes. This succinimide (nitrogen content: 1.4%) was formed by reacting a polybutene-substituted succinic acid derivative with a polyamine.
  • the second polybutene succinimide of this series (nitrogen content: 1.5 %, boron content: 0.5%) was prepared using polybutene of a number-average molecular weight of approximately 1 ,300 and treating the resulting succinimide with boric acid, according to Example No. 8 of U.S. Patent No. 5,356,552.
  • the third polybutene succinimide of this series (nitrogen content: 0.7%) was prepared using polybutene of a number-average molecular weight of approximately 2,200 and treating the resulting succinimide with ethylene carbonate, according to Example No. 17 of United States Patent 5,356,552.
  • test procedures were:
  • Hot Tube Test (KES 07-803) for evaluating detergency at high temperatures.
  • a glass tube having an inner diameter of 2 mm is vertically set.
  • the test oil composition and air are introduced into the glass tube from its lower end at rates of 0.31 cc/hr. and 10 cc/min., respectively, at 290°C (temperature of the heater) for 16 hours. Thereafter, the deposit produced on the glass tube is visually evaluated to mark the lacquer formation on the basis of 10 points. A higher value means that the lacquer is less and the detergency is better.
  • a gasoline engine (6-cylindered engine of V-type and 2 L displacement volume) is operated for 300 hours at a cycle run between low speed run and high speed run according to the test method defined by Japan Automobile Standard Organization (JASO M331-91). Thereafter, the sludge deposited on the rocker cover was evaluated to mark the amount of deposit on the basis of 10 points. A higher value means a less amount of deposit.
  • ZnDTP phosphorus content 7.2% prepared using a secondary alcohol of 3 to 8 carbon atoms: 1.3%.
  • Alkylated diphenylamine 0.5%.
  • Ethylene-propylene copolymer viscosity index improver 6.5%.

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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)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Lubricants (AREA)
EP98949715A 1997-10-01 1998-09-30 Polyalkylensuccinimid-zusammensetzung für brennkraftmaschinen Withdrawn EP1019466A1 (de)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US15801 1996-04-17
JP28466697 1997-10-01
JP28466697A JPH11106776A (ja) 1997-10-01 1997-10-01 潤滑油組成物
US09/015,801 US5861363A (en) 1998-01-29 1998-01-29 Polyalkylene succinimide composition useful in internal combustion engines
PCT/US1998/020715 WO1999016852A1 (en) 1997-10-01 1998-09-30 Polyalkylene succinimide composition useful in internal combustion engines

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Cited By (1)

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WO2006117215A1 (de) 2005-05-04 2006-11-09 E.G.O. Elektro-Gerätebau GmbH Bedienvorrichtung und verfahren zur auswertung einer bedienvorrichtung

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WO2003004589A1 (en) * 2001-07-05 2003-01-16 The Lubrizol Corporation Low-chlorine, polyolefin-substituted, with amine reacted, alpha-beta unsaturated carboxylic compounds
US7238650B2 (en) 2002-06-27 2007-07-03 The Lubrizol Corporation Low-chlorine, polyolefin-substituted, with amine reacted, alpha-beta unsaturated carboxylic compounds
US6696393B1 (en) * 2002-08-01 2004-02-24 Chevron Oronite Company Llc Methods and compositions for reducing wear in internal combustion engines lubricated with a low phosphorus content lubricating oil
US20040087451A1 (en) * 2002-10-31 2004-05-06 Roby Stephen H. Low-phosphorus lubricating oil composition for extended drain intervals
US7485603B2 (en) * 2005-02-18 2009-02-03 Infineum International Limited Soot dispersants and lubricating oil compositions containing same
CN112352035A (zh) * 2018-06-22 2021-02-09 雪佛龙奥伦耐有限责任公司 润滑油组合物

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US5821205A (en) * 1995-12-01 1998-10-13 Chevron Chemical Company Polyalkylene succinimides and post-treated derivatives thereof

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WO2006117215A1 (de) 2005-05-04 2006-11-09 E.G.O. Elektro-Gerätebau GmbH Bedienvorrichtung und verfahren zur auswertung einer bedienvorrichtung

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