US3018247A - Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends - Google Patents

Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends Download PDF

Info

Publication number
US3018247A
US3018247A US15063A US1506360A US3018247A US 3018247 A US3018247 A US 3018247A US 15063 A US15063 A US 15063A US 1506360 A US1506360 A US 1506360A US 3018247 A US3018247 A US 3018247A
Authority
US
United States
Prior art keywords
lubricating oil
dialkylaminoalkyl
carbon atoms
oil compositions
alcohol
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.)
Expired - Lifetime
Application number
US15063A
Other languages
English (en)
Inventor
Robert G Anderson
Frank A Stuart
Alan Y Drummond
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.)
California Research LLC
Original Assignee
California Research 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 to NL262417D priority Critical patent/NL262417A/xx
Application filed by California Research LLC filed Critical California Research LLC
Priority to US15063A priority patent/US3018247A/en
Priority to GB9323/61A priority patent/GB987141A/en
Priority to DEC23650A priority patent/DE1232688B/de
Priority to FR855722A priority patent/FR1283719A/fr
Application granted granted Critical
Publication of US3018247A publication Critical patent/US3018247A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
    • C07D207/412—Acyclic radicals containing more than six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • 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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
    • 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
    • C10M2203/02—Well-defined aliphatic compounds
    • 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
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/022—Well-defined aliphatic compounds saturated
    • 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
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/024—Well-defined aliphatic compounds unsaturated
    • 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
    • C10M2203/04—Well-defined cycloaliphatic compounds
    • 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
    • C10M2203/06—Well-defined aromatic compounds
    • 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
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/022—Ethene
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/024—Propene
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/14—Synthetic waxes, e.g. polythene waxes
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/17—Fisher Tropsch reaction products
    • C10M2205/173—Fisher Tropsch reaction products 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
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • 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
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • 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
    • 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
    • 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
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene 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
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • 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
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
    • 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
    • C10M2215/086—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
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • 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
    • 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
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • 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
    • C10M2227/02—Esters of silicic acids
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/045—Siloxanes with specific structure containing silicon-to-hydroxyl bonds
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/046—Siloxanes with specific structure containing silicon-oxygen-carbon bonds
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/047—Siloxanes with specific structure containing alkylene oxide 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/048—Siloxanes with specific structure containing carboxyl 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • This invention pertains to lubricating oil compositions containing N-dialkylaminoalkyl alkenyl succinimides as detergents.
  • Alkenyl succinie anhydrides and numerous derivatives thereof are Well known in the art.
  • alkenyl suceinic anhydrides in which the alkenyl radical contains from 5 to 20 carbon atoms are taught as corrosion inhibitors in lubricating compositions.
  • products obtained by reacting such alkenyl succinic anhydrides with monoamines are taught as ferrous corrosion inhibitors for lubricating oil compositions.
  • alkenyl succinimides are not useful as detergents for lubricating oil compositions.
  • the alkenyl succinimides described herein are useful as detergents in lubricating oil compositions.
  • the various detergents which are added to crankcase oils to reduce this formation of sludges and varnishes are metal organic compounds, particularly those compounds wherein the metal is linked to an organic group through an oxygen atom.
  • these metalcontaining organic compounds have some effectiveness as detergents for dispersing the precursors of deposits within the oil itself rather than permitting them to form added deposits on the engine parts, they have the disadvantage of forming ash deposits in the engine. These ash deposits lower engine performance by fouling the spark plugs and valves and contributing to preignition.
  • lubricating oil compositions particularly useful for heavy duty service are obtained by incorporating metal dithiophosphates in lubricating oil compositions containing N-dialkylaminoalkyl monoalkenyl succinimides.
  • N-dialkylaminoalkyl alkenyl succinimides are particularly efiective as detergents in lubricating oil compositions.
  • lubricating oil compositions containing metal dithiophosphates and alkenyl succinimides diesel and gasoline engine parts remain remarkably free of deposits and varnish even under severe operating conditions.
  • N-dialkylaminoalkyl monoalkenyl succinimides wherein the alkenyl radical contains from 30 to 200 carbon atoms, and wherein said dialkylaminoalkyl radical contains a total of 3 to 10 carbon atoms, can be represented by the formula:
  • R is an alkenyl radical containing from 30 to 200 carbon atoms
  • R is a divalent alkylene radical
  • R and R are alkyl radicals.
  • the sum of the carbon atoms in the R, R and R is from 3 to 10; that is, R, R and R contain a total of no more than 10 carbon atoms.
  • R is a polymer of an olefin containing from 2 to 5 carbon atoms, wherein the polymer has a molecular weight from 400 to 3000, more particularly from about 900 to about 1200.
  • olefins are exemplified by ethylene, propylene, l-butene, 2- butene, isobutene, and mixtures thereof. Since the methods of polymerizing the olefins to form polymers thereof is immaterial in the formation of the new compound described herein, any of the numerous processes available can be used therefor.
  • R alkylene radicals include the divalent ethylene radical, propylene radical, butylene radical, etc.
  • R and R alkyl radicals include methyl, ethyl, propyl, etc. It is particularly preferred that R contains 3 carbon atoms, and that R and R each contain 1 carbon atom.
  • Amine reactants for the formation of N-dialkylaminoalkyl alkenyl succinimides include dimethylaminomethylamine, dimethylaminoethylamine, dimethylaminopropylamine, dimethylaminobutylamine, dimethylaminoheptylamine, diethylaminomethylamine, diethylaminopropylamine, diethylaminoamylamine, dipropylaminopropylamine, methylpropylaminoamylamine, propylbutylaminoethylamine, etc.
  • the reaction set forth'and described by Equation I hereinabove can proceed in a mol ratio of the polyolefin' to the maleic anhydride of. 1:1 to 1:10; preferablyfrom
  • the reaction temperature can vary from thereby, it is-prefer red to use the higher temperature range (e.g 375 F. to 450 F.).
  • the yield of the imide is ex- I tremely'high even though the reactants are used in equal molar ratios.
  • Equation H The reaction described by Equation H hereinabove can be made'at 220 F., to 500 1F., preferably from 300 F. to 400'F.
  • the alkenyl succinic anhydride and the polyamine are reacted in about equal molar quantities.
  • An excess of amine can be used, and the unreacted amine removed by distillation.
  • the resulting alkenyl succinic anhydride may contain some unreacted polyolefin.
  • the resulting imide formed by'reaction of the alkenyl succinic anhydride and the diamine will contain this polyol efin as an impurity which can be a diluent in the formation of lubricating oil compositions.
  • this unreaCted polyolefin can be removed by precipitation, for
  • the metal dithiophosphates are metal salts of esters of dithiophosphoric acids represented 'by the following formula:
  • R and R may be alkyl, aryl, alkaryl or aralkyl, hydrocarbon radicals containing a total of from 7 to 50 carbon atoms and M is a divalent metal. It is preferred that the R radical contains from 1 to 25 carbon atoms,
  • R radical contains from Ste 25 carbon atoms.
  • R and R may or may not be identical. Because of the improved synergistic effects obtained thereby, it is particularly preferred that R and R are dissimilar alkyl radicals.
  • R and R are identical and consist ofthe lower molecular weight hydrocarbon radicals (e.g., butyl radicals)
  • the metal salt normally does not have sufiicient oil solubility to permit its use in lubricating oil compositions.
  • the R and R are diiferent but still of low molecular weight (e.g., when R is a butyl radical and R is a pentyl radical)
  • R is derived from an alcohol containing no more than 4 carbon atoms; for example, methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, butyl alcohol, sec-butyl alcohol, tertiary butyl alcohol, etc.; and wherein R is derived from alcohols containing from 5 to 18 carbon atoms including pentyl alcohol, hexyl alcohol, methylisobutylcarbinol, methylisopropylcarbinol, heptyl alcohol, isoheptyl alcohol, Z-ethylamyl alcohol, octyl alcohol, isooctyl alcohol, 3-ethylhexyl alcohol, 2-propylamyl alcohol, decyl alcohol,
  • R and R when these are the same include the following radicals: octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, hexylphenyl, decylphenyl, dodecylphenyl, hexadecylphenyl, octadecylphenyl, etc.
  • Divalent metals of the dithiophosphates include the alkaline earth metals such as calcium, barium and strontium, and zinc. It is preferred that the metal is zinc.
  • esters of dithiophosphoric acids used in the preparation of the metal salts of this invention include butyl pentyl dithiophosphoric acid, butyl hexyl dithiophosphoric acid, methyl hexyl dithiophosphoric acid, ethyl hexyl dithiophosphoric acid, butyl methylisobutylcarbinol dithiophosphoric acid, butyl heptyl dithiophosphoric acid, butyl decyl dithiophosphoric acid, butyl isoheptyl dithiophosphoric acid, butyl octadecyl dithiophosphoric acid, dioctyl dithiophosphoric acid, diheptyl dithiophosphoric acid, dihexadecyl dithiophosphoric acid, dioctadecyl dithiophosphoric acid, didectylphenyl dithiophosphoric acid, etc.
  • Lubricating oils which can be used as base oils for lubricating oil compositions of such alkenyl succinimides include a wide variety of lubricating oils, such as naphthenic base, parafiin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylene polymers (such as polymers of propylene, butylene, etc., and the mixtures thereof), alkylene oxide-type polymers (e.g., alkylene oxide polymers prepared by polymerizing the alkylene oxide, e.g., propylene oxide, etc., in the presence of water or alcohols, e.g., ethylene alcohol), dicarboxylic acid esters (e.g., those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkanol succinic acid, fum
  • the above base oils may be used individually or in combinations thereof, wherever miscible or wherever made so by the use of mutual solvents.
  • these alkenyl succinimides can be used in amounts of 0.1% to 80%, by weight, preferably 0.25% to 8%, by Weight.
  • the metal dithiophosphates are used in amounts of 5 millimols to 35 millimols per kilogram (i.e., 5 mM./ kg. to 35 mM./kg.) of finished product based on the metal content, preferably mM./kg. to 18 mM./kg.
  • the succinimides and the metal dithiophosphates are used in certain mol ratios with respect to each other.
  • the succinimide-dithiophosphate mol ratio ranges from about 1:20 to about 10:1; preferably from 1:10 to 6:1, more preferably, 1:2 to 3:1. That is, the succinimide dithiophosphate mol ratio has values from 0.05 to 10, preferably 0.1 to 6, more preferably, 0.5 to 3.0.
  • N-dialkylaminoalkyl monoalkenyl succinimides is illustrated in the following examples.
  • Example I.-Preparati0n of polybutenyl succinic anhydride A mixture of 1000 grams (1 mol) of a polybutene having a molecular weight of about 1000 and 98 grams (1 mol) of maleic anhydride was heated at 410 F. in a nitrogen atmosphere with agitation for a period or" 24 hours. The reaction mixture was cooled to 150 F, and 700 cc. of hexane added; after which the mixture was filtered under vacuum. After vacuum distillation to remove the hexane from the filtrate, the product was maintained at 350 F. at an absolute pressure of 10 mm. Hg for one hour to remove traces of maleic anhydride. The crude polybutenyl succinic anhydride thus prepared had a saponification number of 79.
  • Table I hereinbelow presents further data concerning the preparation of N-dialkylaminoalkyl alkenyl succinimides.
  • the polyamine was dimethylaminopropylamine, and the alkenyl radical on the alkenyl succinimide was 6 a polybutene, the molecular weight of which is noted in Table I.
  • Table II hereinbelow sets forth data showing the synergistic effect obtained by the combination of metal dithiophosphates and N-dialkylaminoalkyl monoalkenyl succinimides as lubricating oil additives.
  • the succinimide used was an N-dimethylaminopropyl alkenyl succinimide wherein the alkenyl radical had a molecular weight of approximately 1000, which alkenylradical was a polymer of isobutene.
  • the dithiophosphate was a zinc salt of a mixed dialkyl dithiophosphate wherein one of the alkyl radicals contained 4 carbon atoms and the other alkyl radical contained 5 carbon atoms.
  • the base oil was an SAE 10 base oil.
  • the PD Nos. refer to the piston discoloration rating.
  • the three piston lands are examined visually. To a piston land which is completely black is assigned a PD number of 800; to one which is completely clean, a PD number of 0; to those intermediate between completely black and completely clean are assigned PD numbers intermediate in proportion to the extent and degree of darkening.
  • Dithiophosphate A was a zinc salt of a mixed dialkyl dithiophosphate wherein one of the alkyl radicals contained 4 carbon atoms, and the other alkyl radical contained 5 carbon atoms; and dithiophosphate B was a zinc salt of a di(alkylphenyl) dithiophosphate wherein the alkyl radicals were derived from propylene polymers having an average of 12-14 carbon atoms.
  • the piston varnish rating is a visual observation of the amount of varnish on a piston skirt, with 10 being the maximum rating for a perfectly clean piston and a 0 being the rating of a piston fully covered with black varnish.
  • This piston varnish rating correlates with road performance in auto-mobiles. This FL-2 test was made as follows:
  • lubricating oil compositions containing the N- dialkylaminoalkyl alkenyl succinimides of this invention may also contain other detergents, viscosity index improving agents, rust inhibitors, oiliness agents, grease thickening agents, etc.
  • a lubricating oil composition consisting essentially of an oil of lubricating viscosity, and from about 0.1% to 80% by weight of an N-dialkylaminoalkyl monoalkenyl suocinimide of the formula wherein R and R alkyl radicals containing a total of 7 to 50 carbon atoms, and wherein the succinimide-dithiophosphate mol ratio is from about 1:2 to about 3:1.
  • a lubricating oil composition consisting essentially of an oil of lubricating viscosity, and from about 0.1% to about 80%, by weight, of an N-dialklaminoalkyl monoalkenyl succinimide of the formula 0 ROHC R NR'-1v CH -O I R3 wherein R is a polyolefin' radical derived from a polymer of an olefin containing from 2 to 5 carbon atoms, said polymer having a molecular weight in the range of about 400 to about 3000, R, R and R are hydrocarbon radicals containing a total of 3 to 10 carbon atoms, and in combination with said succinimide from about 5 rnMJkg, to
  • a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, from about 0.25% to about 8%, by weight, of an .N-dialkylaminoalkyl monoalkenyl succinimide of the formula wherein R is a polyolefin radical derived from a polymer of an olefin containing from 2 to 5 carbon atoms, said polymer having a molecular weight in the range of about 900 to about 1200, R, R and R are hydrocarbon radicals containing a total of 3 to 10 carbon atoms, and in combination with said succinimide from about 5 mM./ kg. to about 35 inM/kg.
  • a lubricating oil composition comprising a major proportion of a petroleum lubricating oil, from about 0.25% to about 8%, by weight, of an N-dimethylaminopropyl monoalkenyl succinimide of the formula R-CH-C CHZ-C 0 wherein R is a polyolefin radical having a molecular weight of about 1000, and from about 12 mM./kg to about 18 mM./kg.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US15063A 1960-03-15 1960-03-15 Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends Expired - Lifetime US3018247A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL262417D NL262417A (zh) 1960-03-15
US15063A US3018247A (en) 1960-03-15 1960-03-15 Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends
GB9323/61A GB987141A (en) 1960-03-15 1961-03-14 Lubricating oil compositions containing metal dithiophosphate-n-dialkylaminoalkyl alkenyl succinimide blends
DEC23650A DE1232688B (de) 1960-03-15 1961-03-15 Schmieroel fuer Verbrennungskraftmaschinen
FR855722A FR1283719A (fr) 1960-03-15 1961-03-15 Compositions d'huiles lubrifiantes contenant des mélanges de dithiophosphates métalliques et de n-dialkylaminoalcényl succinimides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US15063A US3018247A (en) 1960-03-15 1960-03-15 Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends

Publications (1)

Publication Number Publication Date
US3018247A true US3018247A (en) 1962-01-23

Family

ID=21769325

Family Applications (1)

Application Number Title Priority Date Filing Date
US15063A Expired - Lifetime US3018247A (en) 1960-03-15 1960-03-15 Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends

Country Status (4)

Country Link
US (1) US3018247A (zh)
DE (1) DE1232688B (zh)
GB (1) GB987141A (zh)
NL (1) NL262417A (zh)

Cited By (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3131150A (en) * 1961-04-12 1964-04-28 California Research Corp Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines
US3155615A (en) * 1961-08-01 1964-11-03 Exxon Research Engineering Co Sols of metal dialkyl dithiophosphates
US3184411A (en) * 1962-09-28 1965-05-18 California Research Corp Lubricants for reducing corrosion
US3184412A (en) * 1962-09-28 1965-05-18 California Research Corp Lubricants inhibited against oxidation
US3185646A (en) * 1962-09-28 1965-05-25 California Research Corp Corrosion inhibited lubricants
US3185643A (en) * 1962-09-28 1965-05-25 California Reserach Corp Oxidation resistant lubricants
US3185645A (en) * 1962-09-28 1965-05-25 California Research Corp Oxidation inhibited lubricants
US3185647A (en) * 1962-09-28 1965-05-25 California Research Corp Lubricant composition
US3189544A (en) * 1962-12-19 1965-06-15 Shell Oil Co Non-ash-containing lubricating oil composition
US3211652A (en) * 1962-12-03 1965-10-12 Ethyl Corp Phenolic compositions
US3216936A (en) * 1964-03-02 1965-11-09 Lubrizol Corp Process of preparing lubricant additives
US3239462A (en) * 1962-10-15 1966-03-08 Shell Oil Co Lubricating compositions
US3256185A (en) * 1961-06-12 1966-06-14 Lubrizol Corp Lubricant containing acylated aminecarbon disulfide product
US3272743A (en) * 1964-08-05 1966-09-13 Lubrizol Corp Lubricants containing metal-free dispersants and metallic dispersants
US3275554A (en) * 1963-08-02 1966-09-27 Shell Oil Co Polyolefin substituted polyamines and lubricants containing them
US3277133A (en) * 1955-01-27 1966-10-04 Lubrizol Corp Phosphorus-, sulfur-, and metal-containing composition
US3288819A (en) * 1961-10-30 1966-11-29 Standard Oil Co Zinc salts of glycerol monoester dithiophosphates
US3306908A (en) * 1963-12-26 1967-02-28 Lubrizol Corp Reaction products of high molecular weight hydrocarbon succinic compounds, amines and heavy metal compounds
US3311558A (en) * 1964-05-19 1967-03-28 Rohm & Haas N-alkylmorpholinone esters of alkenylsuccinic anhydrides
US3347790A (en) * 1965-07-01 1967-10-17 Lubrizol Corp Lubricating compositions containing metal salts of acids of phosphorus
US3357920A (en) * 1961-08-18 1967-12-12 Shell Oil Co Non-ash containing lubricating oil compositions
US3389083A (en) * 1967-01-26 1968-06-18 Chevron Res Lubricants containing alkali metal dithiophosphates
US3390082A (en) * 1967-09-19 1968-06-25 Lubrizol Corp Lubricants containing metal-free dispersants and inhibitors
DE1271454B (de) * 1963-12-20 1968-06-27 Exxon Research Engineering Co Motorentreibstoff
US3428563A (en) * 1967-10-24 1969-02-18 Chevron Res Alkenyl succinimide-antimony dithiophosphate combinations in lubricants
US3438897A (en) * 1966-10-10 1969-04-15 Shell Oil Co Engine lubricating compositions
US3502677A (en) * 1963-06-17 1970-03-24 Lubrizol Corp Nitrogen-containing and phosphorus-containing succinic derivatives
US4306984A (en) * 1980-06-19 1981-12-22 Chevron Research Company Oil soluble metal (lower) dialkyl dithiophosphate succinimide complex and lubricating oil compositions containing same
EP0399764A1 (en) 1989-05-22 1990-11-28 Ethyl Petroleum Additives Limited Lubricant compositions
US5102566A (en) * 1987-10-02 1992-04-07 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines (pt-727)
US5141657A (en) * 1987-10-02 1992-08-25 Exxon Chemical Patents Inc. Lubricant compositions for internal combustion engines
US5320765A (en) * 1987-10-02 1994-06-14 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines
EP0683220A2 (en) 1994-05-18 1995-11-22 Ethyl Corporation Lubricant additive compositions
WO1998047989A1 (en) 1997-04-21 1998-10-29 Exxon Chemical Patents Inc. Power transmission fluids containing alkyl phosphonates
US20030089028A1 (en) * 2001-03-22 2003-05-15 Jordan Frederick L. Method and composition for using organic, plant-derived, oil-extracted materials in coal-based fuels for reduced emissions
US20030167679A1 (en) * 2000-04-14 2003-09-11 Jordan Frederick L. Organic cetane improver
US6638324B2 (en) 2000-04-14 2003-10-28 Oryxe Energy International, Inc. Organic cetane improver
US20050101497A1 (en) * 2003-11-12 2005-05-12 Saathoff Lee D. Compositions and methods for improved friction durability in power transmission fluids
US20050192185A1 (en) * 2004-02-27 2005-09-01 Saathoff Lee D. Power transmission fluids
US20050250656A1 (en) * 2004-05-04 2005-11-10 Masahiro Ishikawa Continuously variable transmission fluid
EP1640440A1 (en) 2004-09-22 2006-03-29 Infineum International Limited Friction and/or wear reduction in manual or automated manual transmissions
US20060201056A1 (en) * 2000-04-14 2006-09-14 Oryxe Energy International, Inc. Biodiesel fuel additive
US20090042752A1 (en) * 2007-08-09 2009-02-12 Malcolm Waddoups Lubricant Compositions with Reduced Phosphorous Content for Engines having Catalytic Converters
US20090156445A1 (en) * 2007-12-13 2009-06-18 Lam William Y Lubricant composition suitable for engines fueled by alternate fuels
WO2010147993A1 (en) 2009-06-16 2010-12-23 Chevron Phillips Chemical Company Lp Oligomerization of alpha olefins using metallocene-ssa catalyst systems and use of the resultant polyalphaolefins to prepare lubricant blends
WO2011102836A1 (en) 2010-02-19 2011-08-25 Infineum International Limited Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of borated detergents
WO2011102835A1 (en) 2010-02-19 2011-08-25 Toyota Jidosha Kabushiki Kaisha Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of sodium detergents

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4105571A (en) * 1977-08-22 1978-08-08 Exxon Research & Engineering Co. Lubricant composition

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2364284A (en) * 1941-06-17 1944-12-05 Union Oil Co Modified lubricating oil
US2689220A (en) * 1951-03-29 1954-09-14 California Research Corp Lubricating oil compositions of mixed diester dithiophosphates
US2838555A (en) * 1951-10-12 1958-06-10 Lubrizol Corp Group ii metal salts of a mixture of simple diesters of dithiophosphoric acids
US2849398A (en) * 1953-08-19 1958-08-26 Exxon Research Engineering Co Mineral-base lubricating oils and methods for using same
US2892783A (en) * 1958-04-21 1959-06-30 California Research Corp Lubricant composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2364284A (en) * 1941-06-17 1944-12-05 Union Oil Co Modified lubricating oil
US2689220A (en) * 1951-03-29 1954-09-14 California Research Corp Lubricating oil compositions of mixed diester dithiophosphates
US2838555A (en) * 1951-10-12 1958-06-10 Lubrizol Corp Group ii metal salts of a mixture of simple diesters of dithiophosphoric acids
US2849398A (en) * 1953-08-19 1958-08-26 Exxon Research Engineering Co Mineral-base lubricating oils and methods for using same
US2892783A (en) * 1958-04-21 1959-06-30 California Research Corp Lubricant composition

Cited By (71)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3277133A (en) * 1955-01-27 1966-10-04 Lubrizol Corp Phosphorus-, sulfur-, and metal-containing composition
US3131150A (en) * 1961-04-12 1964-04-28 California Research Corp Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines
US3256185A (en) * 1961-06-12 1966-06-14 Lubrizol Corp Lubricant containing acylated aminecarbon disulfide product
US3155615A (en) * 1961-08-01 1964-11-03 Exxon Research Engineering Co Sols of metal dialkyl dithiophosphates
US3357920A (en) * 1961-08-18 1967-12-12 Shell Oil Co Non-ash containing lubricating oil compositions
US3288819A (en) * 1961-10-30 1966-11-29 Standard Oil Co Zinc salts of glycerol monoester dithiophosphates
US3185645A (en) * 1962-09-28 1965-05-25 California Research Corp Oxidation inhibited lubricants
US3185647A (en) * 1962-09-28 1965-05-25 California Research Corp Lubricant composition
US3185643A (en) * 1962-09-28 1965-05-25 California Reserach Corp Oxidation resistant lubricants
US3185646A (en) * 1962-09-28 1965-05-25 California Research Corp Corrosion inhibited lubricants
US3184412A (en) * 1962-09-28 1965-05-18 California Research Corp Lubricants inhibited against oxidation
US3184411A (en) * 1962-09-28 1965-05-18 California Research Corp Lubricants for reducing corrosion
US3239462A (en) * 1962-10-15 1966-03-08 Shell Oil Co Lubricating compositions
US3211652A (en) * 1962-12-03 1965-10-12 Ethyl Corp Phenolic compositions
US3189544A (en) * 1962-12-19 1965-06-15 Shell Oil Co Non-ash-containing lubricating oil composition
US3502677A (en) * 1963-06-17 1970-03-24 Lubrizol Corp Nitrogen-containing and phosphorus-containing succinic derivatives
US3275554A (en) * 1963-08-02 1966-09-27 Shell Oil Co Polyolefin substituted polyamines and lubricants containing them
DE1271454B (de) * 1963-12-20 1968-06-27 Exxon Research Engineering Co Motorentreibstoff
US3306908A (en) * 1963-12-26 1967-02-28 Lubrizol Corp Reaction products of high molecular weight hydrocarbon succinic compounds, amines and heavy metal compounds
US3216936A (en) * 1964-03-02 1965-11-09 Lubrizol Corp Process of preparing lubricant additives
US3311558A (en) * 1964-05-19 1967-03-28 Rohm & Haas N-alkylmorpholinone esters of alkenylsuccinic anhydrides
US3272743A (en) * 1964-08-05 1966-09-13 Lubrizol Corp Lubricants containing metal-free dispersants and metallic dispersants
US3347790A (en) * 1965-07-01 1967-10-17 Lubrizol Corp Lubricating compositions containing metal salts of acids of phosphorus
US3438897A (en) * 1966-10-10 1969-04-15 Shell Oil Co Engine lubricating compositions
US3389083A (en) * 1967-01-26 1968-06-18 Chevron Res Lubricants containing alkali metal dithiophosphates
US3390082A (en) * 1967-09-19 1968-06-25 Lubrizol Corp Lubricants containing metal-free dispersants and inhibitors
US3428563A (en) * 1967-10-24 1969-02-18 Chevron Res Alkenyl succinimide-antimony dithiophosphate combinations in lubricants
US4306984A (en) * 1980-06-19 1981-12-22 Chevron Research Company Oil soluble metal (lower) dialkyl dithiophosphate succinimide complex and lubricating oil compositions containing same
US5102566A (en) * 1987-10-02 1992-04-07 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines (pt-727)
US5141657A (en) * 1987-10-02 1992-08-25 Exxon Chemical Patents Inc. Lubricant compositions for internal combustion engines
US5320765A (en) * 1987-10-02 1994-06-14 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines
EP0399764A1 (en) 1989-05-22 1990-11-28 Ethyl Petroleum Additives Limited Lubricant compositions
EP0683220A2 (en) 1994-05-18 1995-11-22 Ethyl Corporation Lubricant additive compositions
WO1998047989A1 (en) 1997-04-21 1998-10-29 Exxon Chemical Patents Inc. Power transmission fluids containing alkyl phosphonates
US20060201056A1 (en) * 2000-04-14 2006-09-14 Oryxe Energy International, Inc. Biodiesel fuel additive
US20030167679A1 (en) * 2000-04-14 2003-09-11 Jordan Frederick L. Organic cetane improver
US7029506B2 (en) 2000-04-14 2006-04-18 Jordan Frederick L Organic cetane improver
US6638324B2 (en) 2000-04-14 2003-10-28 Oryxe Energy International, Inc. Organic cetane improver
US7141083B2 (en) 2001-03-22 2006-11-28 Oryxe Energy International, Inc. Method and composition for using organic, plant-derived, oil-extracted materials in resid fuel additives for reduced emissions
US20030093944A1 (en) * 2001-03-22 2003-05-22 Jordan Frederick L. Method and composition for using organic, plant-derived, oil-extracted materials in two-cycle oils for reduced emissions
US20030093945A1 (en) * 2001-03-22 2003-05-22 Jordan Frederick L. Method and composition for using organic, plant-derived, oil-extracted materials in gasoline additives for reduced emissions
US7144433B2 (en) 2001-03-22 2006-12-05 Oryxe Energy International, Inc. Method and composition for using organic, plant-derived, oil-extracted materials in fossil fuels for reduced emissions
US20030093942A1 (en) * 2001-03-22 2003-05-22 Jordan Frederick L. Method and composition for using organic, plant-derived, oil-extracted materials in jet fuels for reduced emissions
US20030097783A1 (en) * 2001-03-22 2003-05-29 Jordan Frederick L. Method and composition for using organic, plant-derived, oil-extracted materials in gasolines for reduced emissions
US20030089027A1 (en) * 2001-03-22 2003-05-15 Jordan Frederick L. Method and composition for using organic, plant-derived, oil-extracted materials in fossil fuels for reduced emissions
US7144434B2 (en) 2001-03-22 2006-12-05 Oryxe Energy International, Inc. Method and composition for using organic, plant-derived, oil-extracted materials in coal-based fuels for reduced emissions
US7220289B2 (en) 2001-03-22 2007-05-22 Oryxe Energy International, Inc. Method and composition for using organic, plant-derived, oil-extracted materials in diesel fuel additives for reduced emissions
US20030089026A1 (en) * 2001-03-22 2003-05-15 Jordan Frederick L. Method and composition for using organic, plant-derived, oil-extracted materials in resid fuel additives for reduced emissions
US7160339B2 (en) 2001-03-22 2007-01-09 Oryxe Energy International, Inc. Method and composition for using organic, plant-derived, oil-extracted materials in gasoline additives for reduced emissions
US7160338B2 (en) 2001-03-22 2007-01-09 Oryxe Energy International, Inc. Method and composition for using organic, plant-derived, oil-extracted materials in jet fuels for reduced emissions
US20030089030A1 (en) * 2001-03-22 2003-05-15 Jordan Frederick L. Method and composition for using organic, plant-derived, oil-extracted materials in resid fuels for reduced emissions
US7144435B2 (en) 2001-03-22 2006-12-05 Oryxe Energy International, Inc. Method and composition for using organic, plant-derived, oil-extracted materials in two-cycle oil additives for reduced emissions
US20030089028A1 (en) * 2001-03-22 2003-05-15 Jordan Frederick L. Method and composition for using organic, plant-derived, oil-extracted materials in coal-based fuels for reduced emissions
US20030089029A1 (en) * 2001-03-22 2003-05-15 Jordan Frederick L. Method and composition for using organic, plant-derived, oil-extracted materials in two-cycle oil additives for reduced emissions
US20030093943A1 (en) * 2001-03-22 2003-05-22 Jordan Frederick L. Method and composition for using organic, plant-derived, oil-extracted materials in diesel fuel additives for reduced emissions
EP1531175A2 (en) 2003-11-12 2005-05-18 Afton Chemical Corporation Compositions and methods for improved friction durability in power transmission fluids
US20050101497A1 (en) * 2003-11-12 2005-05-12 Saathoff Lee D. Compositions and methods for improved friction durability in power transmission fluids
US20080090744A1 (en) * 2003-11-12 2008-04-17 Saathoff Lee D Compositions and Methods for Improved Friction Durability in Power Transmission Fluids
US20050192185A1 (en) * 2004-02-27 2005-09-01 Saathoff Lee D. Power transmission fluids
US7947636B2 (en) 2004-02-27 2011-05-24 Afton Chemical Corporation Power transmission fluids
US20050250656A1 (en) * 2004-05-04 2005-11-10 Masahiro Ishikawa Continuously variable transmission fluid
EP1640440A1 (en) 2004-09-22 2006-03-29 Infineum International Limited Friction and/or wear reduction in manual or automated manual transmissions
EP2031045A1 (en) 2007-08-09 2009-03-04 Infineum International Limited Lubricant compositions with reduced phosphorous content for engines having catalytic converters
US20090042752A1 (en) * 2007-08-09 2009-02-12 Malcolm Waddoups Lubricant Compositions with Reduced Phosphorous Content for Engines having Catalytic Converters
US20090156445A1 (en) * 2007-12-13 2009-06-18 Lam William Y Lubricant composition suitable for engines fueled by alternate fuels
EP2072611A1 (en) 2007-12-13 2009-06-24 Afton Chemical Corporation Lubricant composition suitable for engines fueled by alternate fuels
WO2010147993A1 (en) 2009-06-16 2010-12-23 Chevron Phillips Chemical Company Lp Oligomerization of alpha olefins using metallocene-ssa catalyst systems and use of the resultant polyalphaolefins to prepare lubricant blends
EP3587458A1 (en) 2009-06-16 2020-01-01 Chevron Phillips Chemical Company LP Compositions comprising polyalphaolefins
WO2011102836A1 (en) 2010-02-19 2011-08-25 Infineum International Limited Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of borated detergents
WO2011102835A1 (en) 2010-02-19 2011-08-25 Toyota Jidosha Kabushiki Kaisha Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of sodium detergents
US9365794B2 (en) 2010-02-19 2016-06-14 Infineum International Limited Wet friction clutch—lubricant systems providing high dynamic coefficients of friction through the use of borated detergents

Also Published As

Publication number Publication date
GB987141A (en) 1965-03-24
DE1232688B (de) 1967-01-19
NL262417A (zh)

Similar Documents

Publication Publication Date Title
US3018247A (en) Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends
US3018250A (en) Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides
US3024195A (en) Lubricating oil compositions of alkylpiperazine alkenyl succinimides
US3131150A (en) Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines
US3361673A (en) Lubricating oil compositions containing alkenyl succinimides of tetraethylene pentamine
US3184411A (en) Lubricants for reducing corrosion
US3185647A (en) Lubricant composition
US3185645A (en) Oxidation inhibited lubricants
US3216936A (en) Process of preparing lubricant additives
US3876550A (en) Lubricant compositions
US3288714A (en) Lubricating oil compositions containing alkenyl succinic anhydrides
EP0020037B1 (en) Oil-soluble friction-reducing additive, process for the preparation thereof, and lubricating oil or fuel composition containing the additive
US3287271A (en) Combined detergent-corrosion inhibitors
US3525693A (en) Alkenyl succinic polyglycol ether
US3438899A (en) Alkenyl succinimide of tris (aminoalkyl) amine
US3261782A (en) Alkylbutyrolactone-alpha-acetic acids
US3844958A (en) Hydrocarbyl amines for lubricating oil detergents
US3210283A (en) Lubricant containing alkenyl succinimide and hydroxypolyamine
US3185643A (en) Oxidation resistant lubricants
US3224968A (en) Lubricating oil compositions
US3200076A (en) Polypiperazinyl succinimides in lubricating oils
CA1192552A (en) Method for preparing nitrogen- and oxygen-containing compositions useful as lubricant and fuel additives
US3184412A (en) Lubricants inhibited against oxidation
US3200075A (en) Lactone amides in lubricating oils
US3850822A (en) Ashless oil additive combination composed of a nitrogen-containing ashless dispersant phosphosulfurized olefin and phosphorothionyl disulfide