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 PDFInfo
- 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
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 System
- 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 System
- 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.
Description
United States Patent LUBRICATING OIL COMPOSITIONS CONTAINING METAL DITHIOPHOSPHATE N DIALKYLAMI- NOALKYL ALKENYL SUCCINIMIDE BLENDS Robert G. Anderson, Novato, Frank A. Stuart, Orinda, and Alan Y. Drummond, Richmond, Calif., assignors to California Research Corporation, San Francisco, Calif a corporation of Delaware No Drawing. Filed Mar. 15, 1960, Ser. No. 15,063
4 Claims. (Cl. 252-32.7)
This invention pertains to lubricating oil compositions containing N-dialkylaminoalkyl alkenyl succinimides as detergents.
This application is a continuation-in-part of patent application Serial No. 835,390, filed August 24, 1959.
Alkenyl succinie anhydrides and numerous derivatives thereof are Well known in the art. For example, alkenyl suceinic anhydrides in which the alkenyl radical contains from 5 to 20 carbon atoms are taught as corrosion inhibitors in lubricating compositions. Also, products obtained by reacting such alkenyl succinic anhydrides with monoamines are taught as ferrous corrosion inhibitors for lubricating oil compositions.
However, the above known alkenyl succinimides are not useful as detergents for lubricating oil compositions. in contrast thereto, the alkenyl succinimides described herein are useful as detergents in lubricating oil compositions.
Present day internal combustion engines operate at high speeds and high compression ratios. When used in the so-called city stop-and-go driving, which includes the greater part of the driving condition for a large percentage of todays automobiles, the internal combustion engines do not reach the most efficient operating temperature. Under city driving conditions, large amounts of partial oxidation products are formed, and reach the crankcase of the engine by blowing past the piston rings. Most of these partial oxidation products are oil insoluble, tending to form deposits on the various operating parts of the engine, such as the pistons, piston rings, etc. For the purpose of preventing the deposition of these products on the various engine parts, it is necessary to incorporate detergents in the lubricating oil compositions, thus keeping these polymeric products highly dispersed in a condition unfavorable for deposition on metals.
For the most part, 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. Although 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.
It is a particular object of this invention to set forth lubricating oil compositions which are compounded with metal-free detergents.
It is a further object of this invention to provide lubricating oil compositions which are compounded with metal-free detergents whose detergency characteristics are enhanced by the presence of a synergist.
Therefore, in accordance with this invention, it has been discovered that lubricating oil compositions particularly useful for heavy duty service are obtained by incorporating metal dithiophosphates in lubricating oil compositions containing N-dialkylaminoalkyl monoalkenyl succinimides.
The N-dialkylaminoalkyl alkenyl succinimides are particularly efiective as detergents in lubricating oil compositions. By the use of 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.
The 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:
o R-oH-o R \NR-N/ Bro; n
wherein R is an alkenyl radical containing from 30 to 200 carbon atoms, R is a divalent alkylene radical, and 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.
It is particularly preferred that 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. Such 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. in can be described generally by the following equations, wherein a polyolefin is reacted with maleic anhydride to form a monoalkenyl succinic anhydride, which, in turn, is then reacted with a dialkylaminoalkylarnine to form an N-dialkylaminoalkyl monoalkenyl succinimide. Using a polymer of isobutene as an example of the alkenyl 300 F. to 450 F. "Because of the greater yield obtained I I radical, and dimethylaminopropylamine to exemplify the dialkylaminoalkylamine, these equations are as follows:
The above reaction between a polyolefin and maleic 'fanh'ydride is an uncatalyzed addition reaction which "should not be confused with a copolymerization reaction ,7 such as that obtained with a vinyl monomer and maleic anhydride. While the general reaction of an olefin and Equation H hereinabove, the reactants are used in such proportions and the reaction conditions are such that an imide is formed, not a diamide.
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.).
In the second step of the'reacti'on as exemplified by Equation 11 hereinabove, the yield of the imide is ex- I tremely'high even though the reactants are used in equal molar ratios.
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.
Since the reaction between the polyolefin and maleic anhydride may not go to completion, the resulting alkenyl succinic anhydridemay contain some unreacted polyolefin. As it may not be desirable to separate out this unrea'cted polyolcfin at this stage, 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. However, if it isso desired, this unreaCted polyolefin can be removed by precipitation, for
example, by acetone 'or methanol from a hydrocarbon solution. V
The metal dithiophosphates are metal salts of esters of dithiophosphoric acids represented 'by the following formula:
wherein 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,
and that the 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.
When 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. However, when 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), it is possible to prepare metal salts of mixed esters of dithiophosphoric acids which are sufiiciently oil soluble to inhibit the oxidation of the lubricating oil composition. The advantages of the use of low molecular weight R andR' groups also include the decreased cost overthat of the high'molec- Thus, in the practice of this invention, it is preferred to use metal salts of mixed esters of dithiophosphoric acids wherein 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, undecyl alcohol, 'dodecyl alcohol, hexadecyl alcohol, octadecyl alcohol, etc.
Examples of 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.
The 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, fumaric acid, maleic acid, etc., with alcohols, such as butyl alcohol, hexyl alcohol, Z-ethylhexy alcohol, dodecyl alcohol, etc.) liquid esters of acids of phosphorus, alkyl benzenes, polyphenyls (e.g., biphenyls and terphenyls), alkyl biphenyl ethers, polymers of silicon (e.g., tetraethyl silicate, tetraisopropyl silicates, tetra l-methyl- 2-tetraethyl) silicate, hexyl (4-methyl-2-pentoxy) disiloxane, poly(methyl) siloxane, and poly(methylphenyl) siloxane), etc.
The above base oils may be used individually or in combinations thereof, wherever miscible or wherever made so by the use of mutual solvents.
As lubricating oil additives, 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.
The preparation of 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.
Example H.Preparari0n of N-dimethylaminopropyl polyblztenyl succinimide A mixture of 21.3 grams (0.21 mol) of dimethylaminopropylamine and 150 grams (0.09 mol) of the polybutenyl succinic anhydride of Example I hereinabove, was blended with agitation in a nitrogen atmosphere, and the mixture was heated at 500 F. for a period of one hour, after which the absolute pressure was reduced to about 200 mm. Hg at this temperature during a period of 30 minutes to facilitate the removal of Water and excess amine. The reaction mixture was then allowed to reach room temperature at this reduced pressure. The reaction product contained 1.7% nitrogen (theory=1.8%). The identity of the N-dimethylaminopropylalkenyl succinimide was established by means of infra-red spectroscopy.
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.
1 Polyisobutenyl succinic anhydride.
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 data were obtained in a Caterpillar L-l test under Supplement I conditions for a period of hours as described in the Coordinating Research Council Handbook, January 1946.
The PD Nos. refer to the piston discoloration rating. After the engine test, 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.
1 These test results were obtained in a Caterpillar L-1 test under MIL-B2104 conditions. Thus, under the more severe supplement I conditions, these PD numbers would be considerably higher.
Tables III and IV hereinbelow present further data emphasizing the synergistic effects of the succinimidedithiophosphate combination as described herein.
The base oils and the succinimide were the same as described hereinabove for Table II.
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:
A 6-cylinder Chevrolet engine was operated at 2500 rpm. for a period of 40 hours. This test is fully described in a Coordinating Research Council bulletin titled Research Technique for the Determination of the Eifects of Fuels and Lubricants on the Formation of TABLE III Additive E F G H Succinirr'ide, Wt. percent 0. O 0.0 1.0 1.0 Dithiophosphate A, mMJkg 12 0 12 Test Results:
Piston Varnish Ratings 2. 9 2. 9 6. 2 7 5 TABLE IV Additive I I K L M N Succinimide, Wt. percent 0.0 0.0 0. 0 1,0 1.0 1.0 Dithiophosphate A, mM./kg. O 12 0 0 6 l0 Dithiophosphate B, mlVL/kg.. 0 0 12 12 6 2 Test Results:
Piston Varnish Ratings 2. 9 2. 9 2. 9 9.8 7. 7 7, 4
It is readily seen from the data set forth hereinabove that lubricating oil compositions containing metal dithiophosphates and the succinimides described herein are markedly effective for the lubrication of internal combustion engines.
In addition to the dithiophosphates described hereinabove, 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.
We claim:
' l. 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.
2. 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
8 about 35 rnM./kg. of a metal dithiophosphate of formula s ROl S Zn wherein R is an alkyl radical containing from 1 to 4 carbon atoms, and R is an alkyl radical containing from 5 to 18 carbon atoms, wherein the succinimide-dithiophosphate mol ratio is from about 1:2 to about 3:1.
3. 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. of a metal dithiophosphate of the formula wherein R is an alkyl radical containing from 1 to 4 carbon atoms, R is an alkyl radical containing from 5 to 18 carbon atoms, and wherein the succinimide-dithiophosphate mol ratio is from about 1:2 to about 3:1.
4. 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. of a metal dithiophosphate of the formula wherein R is an alkyl radical containing no more than 4 carbon atoms and R is an alkyl radical containing from 5 to 18 carbon atoms, wherein the succinimide-dithiophosphate mol ratio is from about 1:5 to about 3:1.
References Cited in the file of this patent UNITED STATES PATENTS 2,364,284 Freuler Dec. 5, 1944 2,689,220 Mulvany Sept. 14, 1954 2,838,555 Goldsmith June 10, 1958 2,849,398 Moody et al Aug. 26, 1958 2,892,783 Stuart et al June 30, 1959 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,,Ol8 2 47 January 23 1962 Robert G, Anderson et alq It is hereby certified that error ep peers in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.
Column 22 line 58 after "etc."
insert The preparation of monoalkenyl succinimides here'- as the beginning of a new paragraph; column 7 line 54 after "R" insert are Signed and sealed this 5th day of June 1962;
(SEAL)- Attest:
ERNEST w. SWIDER A IDL-LADD Attesting Officer Commissioner of Patents
Claims (1)
1. 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 SUCCINIMIDE OF THE FORMULA
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL262417D NL262417A (en) | 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 |
FR855722A FR1283719A (en) | 1960-03-15 | 1961-03-15 | Lubricating oil compositions containing mixtures of metal dithiophosphates and n-dialkylaminoalkenyl succinimides |
DEC23650A DE1232688B (en) | 1960-03-15 | 1961-03-15 | Lubricating oil for internal combustion engines |
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 (en) |
DE (1) | DE1232688B (en) |
GB (1) | GB987141A (en) |
NL (1) | NL262417A (en) |
Cited By (47)
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 |
US3185647A (en) * | 1962-09-28 | 1965-05-25 | California Research Corp | Lubricant composition |
US3185645A (en) * | 1962-09-28 | 1965-05-25 | California Research Corp | Oxidation inhibited lubricants |
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 |
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 (en) * | 1963-12-20 | 1968-06-27 | Exxon Research Engineering Co | Motor fuel |
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 |
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 |
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4105571A (en) * | 1977-08-22 | 1978-08-08 | Exxon Research & Engineering Co. | Lubricant composition |
Citations (5)
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 |
-
0
- NL NL262417D patent/NL262417A/xx unknown
-
1960
- 1960-03-15 US US15063A patent/US3018247A/en not_active Expired - Lifetime
-
1961
- 1961-03-14 GB GB9323/61A patent/GB987141A/en not_active Expired
- 1961-03-15 DE DEC23650A patent/DE1232688B/en active Pending
Patent Citations (5)
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)
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 |
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 |
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 |
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 (en) * | 1963-12-20 | 1968-06-27 | Exxon Research Engineering Co | Motor fuel |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
---|---|
NL262417A (en) | |
DE1232688B (en) | 1967-01-19 |
GB987141A (en) | 1965-03-24 |
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 | |
US3525693A (en) | Alkenyl succinic polyglycol ether | |
US3438899A (en) | Alkenyl succinimide of tris (aminoalkyl) amine | |
US3287271A (en) | Combined detergent-corrosion inhibitors | |
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 | |
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 | |
US3505227A (en) | Lubricating oil compositions containing bis-alkenyl succinimides of xylylene diamines |