US3024195A - Lubricating oil compositions of alkylpiperazine alkenyl succinimides - Google Patents
Lubricating oil compositions of alkylpiperazine alkenyl succinimides Download PDFInfo
- Publication number
- US3024195A US3024195A US835391A US83539159A US3024195A US 3024195 A US3024195 A US 3024195A US 835391 A US835391 A US 835391A US 83539159 A US83539159 A US 83539159A US 3024195 A US3024195 A US 3024195A
- Authority
- US
- United States
- Prior art keywords
- lubricating oil
- alkylpiperazine
- oil compositions
- carbon atoms
- lubricating
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/56—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—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
- 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
- C10M2205/024—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
- 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
- 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
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two 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
- C10M2209/105—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
- C10M2215/22—Heterocyclic nitrogen 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic 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
- 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
- C10M2217/06—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
- C10M2229/04—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
- 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 having incorporated therein metal-free detergents.
- metal-free detergents are N-substituted alkenyl succinimides.
- Alkenyl succinic anhydrides and numerous derivatives thereof are well known in the art.
- alkenyl succinic anhydrides in which the alkenyl radical contains from to 20 carbon atoms are taught as corrosion inhibitors in lubricating oil compositions.
- products obtained by reacting such alkenyl succinic acid anhydrides with non-cyclic monamines are taught as ferrous corrosion inhibitors for 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 metal-containing 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 2 by fouling spark plugs and valves, and contributing to preignition.
- lubricating oil compositions particularly useful for heavy duty service are obtained by incorporating N-alkylpiperazine monoalkenyl succinimides in oils of lubricating viscosity.
- N-alkylpiperazine monoalkenyl succinimides are new compounds of the formula:
- R is a hydrocarbon radical having a molecular weight from about 400 to about 3000; that is, R is a hydrocarbon radical containing about 30 to about 200 carbon atoms; R is a hydrocarbon radical containing from 1 to 3 carbon atoms; and R" is hydrogen or a hydrocarbon radical containing from 1 to 3 carbon atoms.
- N-substituted alkenyl succinimides can be prepared by reacting maleic anhydride with an olefinic hydrocarbon followed by reacting the resulting alkenyl succinic anhydride with an N-(p-aminoalkyl) piperazine.
- N-(B-aminoalkyl) piperazines are exemplified by N-methyl-N-(fi-aminoethyl) piperazine, N-isopropyl-N'- (fiaminoethyl) piperazine, N-(B-aminoisopropyl) piperazine, etc.
- the R radical of the above formula is derived from an olefin containing from 2 to 5 carbon atoms.
- the alkenyl radical is obtained by polymerizing an olefin containing from 2 to 5 carbon atoms to form a hydrocarbon having a molecular weight ranging from about 400 to about 3000, more preferably, 900 to 1200.
- Such olefins are exemplified by ethylene, propylene, l-butene, Z-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.
- N-substituted monoalkenyl succinimides derived from amine derivatives of piperazine can be described generally by the following equations, using a polymer of isobutene as an example of the alkenyl radical; and N-(fi-aminoethyl) piperazine as an example of an N-(aminoalkyl) piperazine:
- n has a value of about 7 to about 50.
- 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, preferably from 1: 1 to 1:5.
- the reaction temperature can vary from 300 F. to 450 F. Because of the greater yield of products obtained thereby, it is preferred to use the high range of temperatures (e.g., 375 to 450 F.).
- Equation II The reaction described by Equation II hereinabove can be made at 220 F. to 500 F., preferably from 300 F. to 400 F.
- the alkenyl succinic anhydride and the N-alkylaminepiperazines are reacted in about equal molar quantities.
- the resulting alkenylsuccinic anhydride may contain some unreacted polyolefin.
- the resulting imide formed by reaction of the alkenyl succinic anhydride and the diamine will contain this polyolefin as an impurity which can be a diluent in the formation of lubricating oil compositions.
- this unreacted polyolefin' can be removed by precipitation, for example, by acetone or methanol from a hydrocarbon solution.
- Lubricating oils which can be used as base oils include a wide variety of lubricating oils, such as naphthenic base, paraifin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylene poly- .mers (such as polymers of propylene, butylene, etc., and the mixtures thereof), alkylene oxide-type polymers (e.g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing the alkylene oxide in the presence of water or alcohols, e.g'., ethyl alcohol, dicarboxylic acid esters (such as those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkanol succinic acid, furnaric acid, maleic acid, etc., with alcohols such as but
- the above base oils may be used individually or in combinations thereof, wherever miscible or Wherever made so by the use of mutual solvents.
- alkenyl succinimides of this in vention can be used in oils of lubricating viscosity in amounts of 0.1% to by weight, preferably 0.25% to 5%, by weight.
- N-alkylpiperazine alkenyl succinimides is illustrated in the following examples.
- Table I hereinbelow presents data obtained with lubricating oil compositions containing N-alkylpiperazine monoalkenyl succinimides.
- the PD Nos. refer to the piston discoloration rating. After the engine test, the three piston lands are examined visually. To a piston skirt 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.
- the GD Nos. refer to the percentage deposits in the piston ring grooves; and 0 evaluation being a clean groove; and a number of being a groove full of deposits.
- the base oils were California SAE 30 base oils.
- GD N o 39 1 0.3 PD N0 800, 800, 800 25, 0, 5 10, 0, 0
- Table II hereinbelow presents data obtained in an FL2 test, using a 6-cylinder Chrysler engine operating at 2500 r.p.m. for a period of 40 hours, which test is fully described in a Coordinating Research Council bulletin titled Research Technique for the Determination of the Elfects of Fuels and Lubricants on the Formation of Deposits During Moderate Temperature Operation (1948).
- 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 automobiles.
- the base oil was an SAE 30 base oil.
- the succinimide and the dithiophosphate were the same as those described for Table I hereinabove.
- lubricating oil compositions containing the N-substituted alkenyl succinimides of N-alkylpiperazine 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 0.1% to 80%, by Weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
- R is a hydrocarbon radical having a molecular weight from about 400 to about 3000, and R is a hydrocarbon radical containing from 1 to 3 carbon atoms.
- a lubricating oil composition consisting essentially of an oil of lubricating viscosity and from 0.1% to by weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
- R is a hydrocarbon radical having a molecular weight from about 900 to about 1200, and R' is a hydrocarbon radical containing from 1 to 3 carbon atoms.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and firom 0.25 to 5%, by weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
- R is a hydrocarbon radical having a molecular weight from about 900 to about 1200, and R is a hydrocarbon radical containing from 1 to 3 carbon atoms, and R" is selected from the group consisting of hydrogen and hydrocarbon radicals containing from 1 to 3 carbon atoms.
- a lubricating oil composition comprising a major proportion of a petroleum lubricating oil and from 0.25% to 5%, by weight, of an N-substituted monoalkenyl succinimide of the formula:
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and a minor proportion, in an amount sufiicient to impart detergency to said oil, of an N-alkylpiperazine monoalkenyl succinim ide of the formula:
- R is a hydrocarbon radical having a molecular weight from about 400 to about 3,000
- R is a hydrocarbon radical containing from one to three carbon atoms
- R" is selected from the group consisting of hydrogen and hydrocarbon radicals containing from 1 to 3 carbon atoms.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and a minor proportion, an amount sufiicient to impart detergency to said oil, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
- R is a hydrocarbon radical containing from about 30 to about 200 carbon atoms formed by polymerizing olefins containing from 2 to 5 carbon atoms, and R is a hydrocarbon radical containing from 1 to 3 carbon atoms.
- 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-alkylpiperazine monoalkenyl succinimide of the formula:
- R is an aleknyl radical containing from 30 to 200 carbon atoms and which is a polymer of an olefin containing from 2 to 5 carbon atoms, and R is an alkyl radical containing from 1 to 3 carbon atoms.
- a lubricating oil composition comprising a" major C II;
- n has a value of about 7 to about 50.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
United State 3,024,195 Patented Mar. 6, 1932 3,024,195 LUBRICATING OIL COMPGSKTHONS F ALKYL- PIPERAZINE ALKENYL SUCCINIMIDES Alan Y. Drummond, Richmond, Robert G. Anderson, Novato, and Frank A. Stuart, Orinda, Calif, assignors to California Research Corporation, San Francisco, Calif., a corporation of Delaware N0 Drawing. Filed Aug. 24, 1959, er. No. 835,391 9 Claims. (Cl. 252-51.5)
This invention pertains to lubricating oil compositions having incorporated therein metal-free detergents. These particular metal-free detergents are N-substituted alkenyl succinimides.
Alkenyl succinic anhydrides and numerous derivatives thereof are well known in the art. For example, alkenyl succinic anhydrides in which the alkenyl radical contains from to 20 carbon atoms are taught as corrosion inhibitors in lubricating oil compositions. Also, products obtained by reacting such alkenyl succinic acid anhydrides with non-cyclic monamines are taught as ferrous corrosion inhibitors for lubricating oil compositions.
However, the above known alkenyl succinimides are not useful as detergents in lubricating oil compositions. In contrast thereto, the N-substituted polyamine alkenyl succinimides which are described herein are new compounds which 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 metal-containing 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 2 by fouling spark plugs and valves, and contributing to preignition.
It is a particular object of this invention to provide lubricating oil compositions which are compounded with a metal-free detergent.
Therefore, in accordance with this invention, it has been discovered that lubricating oil compositions particularly useful for heavy duty service are obtained by incorporating N-alkylpiperazine monoalkenyl succinimides in oils of lubricating viscosity.
By the use of lubricating oil compositions containing the N-substituted alkenyl succinimides described herein, diesel and gasoline engine parts remain remarkably free of deposits and varnish, even under severe operating conditions.
The N-alkylpiperazine monoalkenyl succinimides are new compounds of the formula:
wherein R is a hydrocarbon radical having a molecular weight from about 400 to about 3000; that is, R is a hydrocarbon radical containing about 30 to about 200 carbon atoms; R is a hydrocarbon radical containing from 1 to 3 carbon atoms; and R" is hydrogen or a hydrocarbon radical containing from 1 to 3 carbon atoms.
These N-substituted alkenyl succinimides can be prepared by reacting maleic anhydride with an olefinic hydrocarbon followed by reacting the resulting alkenyl succinic anhydride with an N-(p-aminoalkyl) piperazine. Such N-(B-aminoalkyl) piperazines are exemplified by N-methyl-N-(fi-aminoethyl) piperazine, N-isopropyl-N'- (fiaminoethyl) piperazine, N-(B-aminoisopropyl) piperazine, etc.
The R radical of the above formula, that is, the alkenyl radical, is derived from an olefin containing from 2 to 5 carbon atoms. Thus, the alkenyl radical is obtained by polymerizing an olefin containing from 2 to 5 carbon atoms to form a hydrocarbon having a molecular weight ranging from about 400 to about 3000, more preferably, 900 to 1200. Such olefins are exemplified by ethylene, propylene, l-butene, Z-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.
The preparation of N-substituted monoalkenyl succinimides derived from amine derivatives of piperazine can be described generally by the following equations, using a polymer of isobutene as an example of the alkenyl radical; and N-(fi-aminoethyl) piperazine as an example of an N-(aminoalkyl) piperazine:
wherein n has a value of about 7 to about 50.
The above reaction between a polyolefin and maleic anhydride is an uncatalyzed addition reaction which should not be confused with a copolymerization reaction such as that obtained with a vinyl monomer and maleic anhydride. While the general reaction of an olefin and maleic anhydride is well known for olefins of low molecular weight (e.g., olefin-s of 18 carbon atoms), no previous work has been done with maleic anhydride and the high molecular weight olefins as described herein.
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, preferably from 1: 1 to 1:5. The reaction temperature can vary from 300 F. to 450 F. Because of the greater yield of products obtained thereby, it is preferred to use the high range of temperatures (e.g., 375 to 450 F.).
In the second step of the reaction as exemplified by Equation II hereinabove, the yield of the imide is extremely high even though the reactants are used in equal molor ratios.
The reaction described by Equation II hereinabove can be made at 220 F. to 500 F., preferably from 300 F. to 400 F. The alkenyl succinic anhydride and the N-alkylaminepiperazines are reacted in about equal molar quantities.
Since the reaction between the polyolefin and maleic anhydride may not go to completion, the resulting alkenylsuccinic anhydride may contain some unreacted polyolefin. As it may not be desirable to separate out this unreacted polyolefin at this stage, the resulting imide formed by reaction of the alkenyl succinic anhydride and the diamine will contain this polyolefin as an impurity which can be a diluent in the formation of lubricating oil compositions. However, if it is so desired, this unreacted polyolefin' can be removed by precipitation, for example, by acetone or methanol from a hydrocarbon solution.
Lubricating oils which can be used as base oils include a wide variety of lubricating oils, such as naphthenic base, paraifin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylene poly- .mers (such as polymers of propylene, butylene, etc., and the mixtures thereof), alkylene oxide-type polymers (e.g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing the alkylene oxide in the presence of water or alcohols, e.g'., ethyl alcohol, dicarboxylic acid esters (such as those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkanol succinic acid, furnaric acid, maleic acid, etc., with alcohols such as butyl alcohol, hexyl alcohol, 2-ethyl hexyl alcohol, dodecyl alcohol, etc.), liquid esters of acids of phosphorus, alkyl benzenes (e.g., monoalkyl benzene such as dodecyl benzene, tetradecyl benzene, etc., and dialkyl benzenes (e.g., nnonyl 2-ethyl hexyl benzene); polyphenyls (e.g., biphenyls and terphenyls), alkyl biphenyl ethers, polymers of silicon (e.g., tetraethyl silicate, tetrai-sopropyl silicates, tetra-(4-methyl-2-tetraethyl) silicate, hexyl (4-methyl-2-pentoxy) disiloxane, poly(rnethyl) siloxane, poly(methylphenyl) siloxane, etc. Synthetic oils of the alkylene oxide-type polymers which may be used include those exemplified by the alkylene oxide polymers.
The above base oils may be used individually or in combinations thereof, wherever miscible or Wherever made so by the use of mutual solvents.
The above-described alkenyl succinimides of this in vention can be used in oils of lubricating viscosity in amounts of 0.1% to by weight, preferably 0.25% to 5%, by weight.
The preparation of N-alkylpiperazine alkenyl succinimides is illustrated in the following examples.
EXAMPLE I.-PREPAR ATION 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 of 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. atan 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 lI.-PREPARATION OF N-ETHYLPIPER- AZINE POLYBUTENYL SUCCINIMIDE ANHY- DRIDE A mixture of 18 grams (0.14 mol) of N-(fl-aminoethyl) piperazine and 200 grams (0.127 mol) of the polybutenyl succinic anhydride of Example I hereinabove was blended with agitation in a nitrogen atmosphere. The mixture was heated at 500 F. for one hour, after which the absolute pressure was reduced to about 200 mm. Hg to facilitate the removal of water and unreacted piperazine. The reaction mixture was then allowed to reach room temperature at this reduced pressure. The reaction product contained 2.59% nitrogen (theory=2.67%). Infrared analysis showed that the reaction product was an imide containing a polybutene side chain.
Table I hereinbelow presents data obtained with lubricating oil compositions containing N-alkylpiperazine monoalkenyl succinimides.
The tests were made in a Caterpillar L-1 engine according to MilL-2104 conditions for a period of .120 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 skirt 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.
The GD Nos. refer to the percentage deposits in the piston ring grooves; and 0 evaluation being a clean groove; and a number of being a groove full of deposits.
The base oils were California SAE 30 base oils.
Table I Additive A B C Sueclnimide, weight percent 0. 1.0 1.0 Dithiophosphate;mM./kg 0. 0 0. 0 12 st Results:
GD N o 39 1 0.3 PD N0 800, 800, 800 25, 0, 5 10, 0, 0
Table II hereinbelow presents data obtained in an FL2 test, using a 6-cylinder Chevrolet engine operating at 2500 r.p.m. for a period of 40 hours, which test is fully described in a Coordinating Research Council bulletin titled Research Technique for the Determination of the Elfects of Fuels and Lubricants on the Formation of Deposits During Moderate Temperature Operation (1948).
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 automobiles.
The base oil was an SAE 30 base oil.
The succinimide and the dithiophosphate were the same as those described for Table I hereinabove.
It is readily seen from the data set forth hereinabove in Tables I and -II that lubricating oil compositions containing the N-alkylpiperazine alkenyl succinimides as described herein are superior as lubricating oil compositions for the lubricating of internal combustion engines.
vIn addition to the dithiophosphate described hereinabove, lubricating oil compositions containing the N-substituted alkenyl succinimides of N-alkylpiperazine of this invention may also contain other detergents, viscosity index improving agents, rust inhibitors, oiliness agents, grease thickening agents, etc.
We claim:
1. A lubricating oil composition consisting essentially of an oil of lubricating viscosity and from 0.1% to 80%, by Weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
wherein R is a hydrocarbon radical having a molecular weight from about 400 to about 3000, and R is a hydrocarbon radical containing from 1 to 3 carbon atoms.
2. A lubricating oil composition consisting essentially of an oil of lubricating viscosity and from 0.1% to by weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
wherein R is a hydrocarbon radical having a molecular weight from about 900 to about 1200, and R' is a hydrocarbon radical containing from 1 to 3 carbon atoms.
3. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and firom 0.25 to 5%, by weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
wherein R is a hydrocarbon radical having a molecular weight from about 900 to about 1200, and R is a hydrocarbon radical containing from 1 to 3 carbon atoms, and R" is selected from the group consisting of hydrogen and hydrocarbon radicals containing from 1 to 3 carbon atoms.
4. A lubricating oil composition comprising a major proportion of a petroleum lubricating oil and from 0.25% to 5%, by weight, of an N-substituted monoalkenyl succinimide of the formula:
CH; CH;
CHz-CH: CHa/n CHICHQN NH GHQ-T"? CHPCHI wherein n has a value of about 7 to about 5 0.
5. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and a minor proportion, in an amount sufiicient to impart detergency to said oil, of an N-alkylpiperazine monoalkenyl succinim ide of the formula:
wherein R is a hydrocarbon radical having a molecular weight from about 400 to about 3,000, R is a hydrocarbon radical containing from one to three carbon atoms, and R" is selected from the group consisting of hydrogen and hydrocarbon radicals containing from 1 to 3 carbon atoms.
6. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and a minor proportion, an amount sufiicient to impart detergency to said oil, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
wherein R is a hydrocarbon radical containing from about 30 to about 200 carbon atoms formed by polymerizing olefins containing from 2 to 5 carbon atoms, and R is a hydrocarbon radical containing from 1 to 3 carbon atoms.
7. 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-alkylpiperazine monoalkenyl succinimide of the formula:
wherein R is an aleknyl radical containing from 30 to 200 carbon atoms and which is a polymer of an olefin containing from 2 to 5 carbon atoms, and R is an alkyl radical containing from 1 to 3 carbon atoms.
8. A lubricating oil composition comprising a" major C II;
proportion of an oil of lubricating viscosity and from 0.25% to 5%, by weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
wherein n has a value of about 7 to about 50.
References Cited in thefile of this patent UNITED STATES PATENTS 2,490,744 Trigg et al Dec. 6, 1949 2,604,451 Rocchini July 22, 1952 2,638,450 White et a1 May 12, 19 52 UNITED STATES PATENT OFFICE CERTIFICATION OF CORRECTION Patent No. 3,024,195 March a, 1962 Alan Y. Drummond et a1.
It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.
Columns 1 and 2, bottom of the page, the front end portion of the reactant and the reaction product of the equations, and the top of column 3, two occurrences, should appear as shown below instead of as in the patent:
H CH3 n column 2, lines 18 to 24, column 5, lines 69 to 75, column 6, lines 8 to 13, lines 21 to 27, lines 49 to 55, lines 67 to 73, column '7, lines 7 to 13, and column 8, lines 4 to 9,
the left-hand portion of the formula, each occurrence, should appear as shown below instead of as in the patent:
SEAL) ittest:
IRNEST W. SWIDER lttesting Officer DAVID L. LADD Commissioner of Patents
Claims (1)
1. A LUBRICATING OIL COMPOSITION CONSISTING ESSENTIALLY OF AN OIL OF LUBRICATING VISCOSITY AND FROM 0.1% TO 80%, BY WEIGHT, OF AN N-ALKYLPIPERAZINE MONOALKENYL SUCCINIMIDE OF THE FORMULA:
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL255193D NL255193A (en) | 1959-08-24 | ||
US835391A US3024195A (en) | 1959-08-24 | 1959-08-24 | Lubricating oil compositions of alkylpiperazine alkenyl succinimides |
US835389A US3024237A (en) | 1959-08-24 | 1959-08-24 | Alkenyl succinimides of piperazines |
GB26926/60A GB934401A (en) | 1959-08-24 | 1960-08-03 | Alkylpiperazine alkenyl succinimides and their use in lubricating oil compositions |
FR836640A FR1265784A (en) | 1959-08-24 | 1960-08-24 | N-Alkylpiperazine alkenyl succinimides detergents and lubricating oil compositions containing them |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US835391A US3024195A (en) | 1959-08-24 | 1959-08-24 | Lubricating oil compositions of alkylpiperazine alkenyl succinimides |
US835389A US3024237A (en) | 1959-08-24 | 1959-08-24 | Alkenyl succinimides of piperazines |
Publications (1)
Publication Number | Publication Date |
---|---|
US3024195A true US3024195A (en) | 1962-03-06 |
Family
ID=27125785
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US835391A Expired - Lifetime US3024195A (en) | 1959-08-24 | 1959-08-24 | Lubricating oil compositions of alkylpiperazine alkenyl succinimides |
US835389A Expired - Lifetime US3024237A (en) | 1959-08-24 | 1959-08-24 | Alkenyl succinimides of piperazines |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US835389A Expired - Lifetime US3024237A (en) | 1959-08-24 | 1959-08-24 | Alkenyl succinimides of piperazines |
Country Status (3)
Country | Link |
---|---|
US (2) | US3024195A (en) |
GB (1) | GB934401A (en) |
NL (1) | NL255193A (en) |
Cited By (94)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3154560A (en) * | 1961-12-04 | 1964-10-27 | Monsanto Co | Nu, nu'-azaalkylene-bis |
US3172856A (en) * | 1965-03-09 | Copolymers of n-alkyl piperazine acry- late and alkyl acrylate and lubricat- ing oils containing them | ||
US3184474A (en) * | 1962-09-05 | 1965-05-18 | Exxon Research Engineering Co | Reaction product of alkenyl succinic acid or anhydride with polyamine and polyhydricmaterial |
US3185704A (en) * | 1962-09-04 | 1965-05-25 | Exxon Research Engineering Co | Formamide of mono-alkenyl succinimide |
US3194814A (en) * | 1962-10-18 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-allyl succinimide |
US3194812A (en) * | 1962-08-31 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-para amino-phenyl succinimide |
US3194813A (en) * | 1962-10-18 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-omega amino hexylsuccinimide |
US3200075A (en) * | 1963-02-19 | 1965-08-10 | California Research Corp | Lactone amides in lubricating oils |
US3200076A (en) * | 1963-03-28 | 1965-08-10 | California Research Corp | Polypiperazinyl succinimides in lubricating oils |
US3219666A (en) * | 1959-03-30 | 1965-11-23 | Derivatives of succinic acids and nitrogen compounds | |
US3223625A (en) * | 1963-11-12 | 1965-12-14 | Exxon Research Engineering Co | Colloidal molybdenum complexes and their preparation |
US3224975A (en) * | 1962-12-03 | 1965-12-21 | Ethyl Corp | Lubricating oil compositions |
US3224968A (en) * | 1962-12-03 | 1965-12-21 | Ethyl Corp | Lubricating oil compositions |
US3272746A (en) * | 1965-11-22 | 1966-09-13 | Lubrizol Corp | Lubricating composition containing an acylated nitrogen compound |
US3307928A (en) * | 1963-01-30 | 1967-03-07 | Exxon Research Engineering Co | Gasoline additives for enhancing engine cleanliness |
US3311558A (en) * | 1964-05-19 | 1967-03-28 | Rohm & Haas | N-alkylmorpholinone esters of alkenylsuccinic anhydrides |
US3312619A (en) * | 1963-10-14 | 1967-04-04 | Monsanto Co | 2-substituted imidazolidines and their lubricant compositions |
US3367943A (en) * | 1963-11-01 | 1968-02-06 | Exxon Research Engineering Co | Process for preparing oil soluble additives which comprises reacting a c2 to c5 alkylene oxide with (a) reaction product of an alkenylsuccinic anhydride and an aliphaticpolyamine (b) reaction product of alkenylsuccinic anhydride, a c1 to c30 aliphatic hydrocarbon carboxylic acid and an aliphatic polyamine |
US3389083A (en) * | 1967-01-26 | 1968-06-18 | Chevron Res | Lubricants containing alkali metal dithiophosphates |
US3424684A (en) * | 1967-03-10 | 1969-01-28 | Texaco Inc | Lubricant containing polymeric product of alkenyl succinic anhydride and hydroxy containing piperazine derivative |
US3426738A (en) * | 1967-10-16 | 1969-02-11 | Chevron Res | Method of operation and lubricant for closed emission internal combustion engines |
US3449249A (en) * | 1964-05-08 | 1969-06-10 | Shell Oil Co | Lubricant compositions |
US3502677A (en) * | 1963-06-17 | 1970-03-24 | Lubrizol Corp | Nitrogen-containing and phosphorus-containing succinic derivatives |
US4465606A (en) * | 1982-07-22 | 1984-08-14 | Union Oil Company Of California | Stabilization of hydrocarbon oil |
US4471091A (en) * | 1982-08-09 | 1984-09-11 | The Lubrizol Corporation | Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4486573A (en) * | 1982-08-09 | 1984-12-04 | The Lubrizol Corporation | Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4489194A (en) * | 1982-08-09 | 1984-12-18 | The Lubrizol Corporation | Carboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4559155A (en) * | 1982-08-09 | 1985-12-17 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4564460A (en) * | 1982-08-09 | 1986-01-14 | The Lubrizol Corporation | Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4575526A (en) * | 1982-08-09 | 1986-03-11 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same |
US4596663A (en) * | 1982-08-09 | 1986-06-24 | The Lubrizol Corporation | Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4613342A (en) * | 1982-08-09 | 1986-09-23 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4623684A (en) | 1982-08-09 | 1986-11-18 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4749505A (en) * | 1985-07-08 | 1988-06-07 | Exxon Chemical Patents Inc. | Olefin polymer viscosity index improver additive useful in oil compositions |
US4824884A (en) * | 1987-08-12 | 1989-04-25 | Pennwalt Corporation | Cyclic anhydride derivatives of hydrazide functionalized hindered amine light stabilizers |
US4946612A (en) * | 1986-06-09 | 1990-08-07 | Idemitsu Kosan Company Limited | Lubricating oil composition for sliding surface and for metallic working and method for lubrication of machine tools using said composition |
US5041622A (en) * | 1988-04-22 | 1991-08-20 | The Lubrizol Corporation | Three-step process for making substituted carboxylic acids and derivatives thereof |
US5171466A (en) * | 1990-04-10 | 1992-12-15 | Ethyl Petroleum Additives Limited | Succinimide compositions |
US5232616A (en) * | 1990-08-21 | 1993-08-03 | Chevron Research And Technology Company | Lubricating compositions |
US5330667A (en) * | 1992-04-15 | 1994-07-19 | Exxon Chemical Patents Inc. | Two-cycle oil additive |
US5356552A (en) * | 1993-03-09 | 1994-10-18 | Chevron Research And Technology Company, A Division Of Chevron U.S.A. Inc. | Chlorine-free lubricating oils having modified high molecular weight succinimides |
US5478367A (en) * | 1991-10-11 | 1995-12-26 | Exxon Chemical Patents Inc. | Fuel oil compositions |
EP0776963A1 (en) | 1995-12-01 | 1997-06-04 | Chevron Chemical Company | Polyalkylene succinimides and post-treated derivatives thereof |
EP0831104A2 (en) | 1996-08-20 | 1998-03-25 | Chevron Chemical Company | Novel dispersant terpolymers |
US6294506B1 (en) | 1993-03-09 | 2001-09-25 | Chevron Chemical Company | Lubricating oils having carbonated sulfurized metal alkyl phenates and carbonated metal alkyl aryl sulfonates |
US20050181957A1 (en) * | 2002-05-30 | 2005-08-18 | Hiroaki Koshima | Lubricating oil additive composition for internal combustion engine |
US20060135375A1 (en) * | 2004-12-21 | 2006-06-22 | Chevron Oronite Company Llc | Anti-shudder additive composition and lubricating oil composition containing the same |
EP1728848A1 (en) | 2005-06-01 | 2006-12-06 | Infineum International Limited | Use of unsaturated olefin polymers to improve the compatibility between nitrile rubber seals and lubricating oil compositions |
EP2133406A1 (en) * | 2008-06-09 | 2009-12-16 | Idemitsu Kosan Co., Ltd. | Lubricating oil composition for internal combustion engine |
EP2161326A1 (en) | 2008-09-05 | 2010-03-10 | Infineum International Limited | Lubricating oil compositions |
EP2163602A1 (en) | 2008-09-05 | 2010-03-17 | Infineum International Limited | A lubricating oil composition |
EP2233554A1 (en) | 2009-03-27 | 2010-09-29 | Infineum International Limited | Lubricating oil compositions |
EP2290038A2 (en) | 2009-08-24 | 2011-03-02 | Infineum International Limited | A lubricating oil composition |
EP2290043A1 (en) | 2009-08-24 | 2011-03-02 | Infineum International Limited | A lubricating oil composition comprising metal dialkyldithiophosphate and carbodiimide |
EP2363454A1 (en) | 2010-02-23 | 2011-09-07 | Infineum International Limited | A lubricating oil composition |
EP2371932A1 (en) | 2010-04-01 | 2011-10-05 | Infineum International Limited | A lubricating oil composition |
EP2374866A1 (en) | 2010-04-06 | 2011-10-12 | Infineum International Limited | A lubricating oil composition comprising alkoxylated phenol-formaldehyde condensate |
EP2390306A1 (en) | 2009-12-01 | 2011-11-30 | Infineum International Limited | A lubricating oil composition |
EP2453000A1 (en) | 2010-11-08 | 2012-05-16 | Infineum International Limited | Lubricating Oil Composition comprising a hydrogenated imide derived from a Diels-Alder adduct of maleic anhydride and a furan |
EP2457984A1 (en) | 2010-11-30 | 2012-05-30 | Infineum International Limited | A lubricating oil composition |
EP2559748A1 (en) | 2011-08-19 | 2013-02-20 | Infineum International Limited | Lubricating oil composition |
EP2584025A1 (en) | 2011-10-21 | 2013-04-24 | Infineum International Limited | Lubricating oil composition |
EP2620207A2 (en) | 2008-10-31 | 2013-07-31 | Calera Corporation | Non-cementitious compositions comprising CO2 sequestering additives |
EP2692839A1 (en) | 2012-07-31 | 2014-02-05 | Infineum International Limited | A lubricating oil compostion comprising a corrosion inhibitor |
EP2692840A1 (en) | 2012-07-31 | 2014-02-05 | Infineum International Limited | Lubricating oil composition |
EP2913384A1 (en) | 2014-02-26 | 2015-09-02 | Infineum International Limited | A lubricating oil composition |
US9133581B2 (en) | 2008-10-31 | 2015-09-15 | Calera Corporation | Non-cementitious compositions comprising vaterite and methods thereof |
EP3034587A1 (en) | 2014-12-19 | 2016-06-22 | Infineum International Limited | Marine engine lubrication |
WO2017013257A1 (en) | 2015-07-22 | 2017-01-26 | Chevron Oronite Technology B.V. | Marine diesel cylinder lubricant oil compositions |
EP3192858A1 (en) | 2016-01-15 | 2017-07-19 | Infineum International Limited | Use of lubricating oil composition |
EP3222698A1 (en) | 2016-03-22 | 2017-09-27 | Infineum International Limited | Additive concentrates |
EP3252130A1 (en) | 2016-06-03 | 2017-12-06 | Infineum International Limited | Additive package and lubricating oil composition |
EP3257921A1 (en) | 2016-06-14 | 2017-12-20 | Infineum International Limited | Lubricating oil additives |
WO2018041732A1 (en) | 2016-08-29 | 2018-03-08 | Chevron Oronite Technology B.V. | Marine diesel cylinder lubricant oil compositions |
WO2018069460A1 (en) | 2016-10-12 | 2018-04-19 | Chevron Oronite Technology B.V. | Marine diesel lubricant oil compositions |
WO2018073268A1 (en) | 2016-10-18 | 2018-04-26 | Chevron Oronite Technology B.V. | Marine diesel lubricant oil compositions |
EP3321347A1 (en) | 2016-11-14 | 2018-05-16 | Infineum International Limited | Lubricating oil additives based on overbased gemini surfactant |
EP3461877A1 (en) | 2017-09-27 | 2019-04-03 | Infineum International Limited | Improvements in and relating to lubricating compositions |
EP3470499A1 (en) | 2017-10-16 | 2019-04-17 | Infineum International Limited | Use of detergent for internal compustion engine oil compositions |
EP3473694A1 (en) | 2017-10-12 | 2019-04-24 | Infineum International Limited | Lubricating oil compositions |
EP3492567A1 (en) | 2017-11-29 | 2019-06-05 | Infineum International Limited | Lubricating oil additives |
EP3492566A1 (en) | 2017-11-29 | 2019-06-05 | Infineum International Limited | Lubricating oil additives |
EP3502217A1 (en) | 2017-11-29 | 2019-06-26 | Infineum International Limited | Lubricating oil compositions |
EP3741832A2 (en) | 2019-05-24 | 2020-11-25 | Infineum International Limited | Nitrogen-containing lubricating oil additives |
EP3770235A1 (en) | 2018-09-24 | 2021-01-27 | Infineum International Limited | Polymers and lubricating compositions containing polymers |
EP3851507A1 (en) | 2020-01-15 | 2021-07-21 | Infineum International Limited | Polymers and lubricating compositions containing polymers |
EP3926026A1 (en) | 2020-06-16 | 2021-12-22 | Infineum International Limited | Oil compositions |
US11299690B2 (en) | 2016-03-22 | 2022-04-12 | Infineum International Ltd. | Additive concentrates |
US11599332B1 (en) | 2007-10-04 | 2023-03-07 | Great Northern Research, LLC | Multiple shell multi faceted graphical user interface |
EP4159832A1 (en) | 2021-10-04 | 2023-04-05 | Infineum International Limited | Lubricating oil compositions |
EP4174152A1 (en) | 2021-10-29 | 2023-05-03 | Infineum International Limited | Ionic liquid composition |
EP4174153A1 (en) | 2021-10-29 | 2023-05-03 | Infineum International Limited | Method of limiting chemical degradation due to nitrogen dioxide contamination |
EP4174154A1 (en) | 2021-10-29 | 2023-05-03 | Infineum International Limited | Method of limiting chemical degradation due to nitrogen dioxide contamination |
EP4303287A1 (en) | 2022-07-06 | 2024-01-10 | Infineum International Limited | Lubricating oil compositions |
Families Citing this family (57)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3235484A (en) * | 1962-03-27 | 1966-02-15 | Lubrizol Corp | Cracking processes |
US3184412A (en) * | 1962-09-28 | 1965-05-18 | California Research Corp | Lubricants inhibited against oxidation |
US3235503A (en) * | 1963-03-28 | 1966-02-15 | Chevron Res | Lubricant containing alkylene polyamine reaction product |
US3252908A (en) * | 1963-11-07 | 1966-05-24 | Lubrizol Corp | Lubricating oil and additive composition |
ZA771959B (en) * | 1976-04-01 | 1978-03-29 | Orogil | Compositions based on alkenylsuccinimides |
CA1333596C (en) * | 1986-10-16 | 1994-12-20 | Robert Dean Lundberg | High functionality low molecular weight oil soluble dispersant additives useful in oleaginous compositions |
US5312555A (en) * | 1990-02-16 | 1994-05-17 | Ethyl Petroleum Additives, Inc. | Succinimides |
FR2762006B1 (en) * | 1997-04-11 | 2003-09-12 | Chevron Res & Tech | USE OF HIGH MOLECULAR WEIGHT SURFACTANTS AS AGREEMENTS TO IMPROVE FILTERABILITY IN HYDRAULIC LUBRICANTS |
US6617287B2 (en) | 2001-10-22 | 2003-09-09 | The Lubrizol Corporation | Manual transmission lubricants with improved synchromesh performance |
US6642191B2 (en) | 2001-11-29 | 2003-11-04 | Chevron Oronite Company Llc | Lubricating oil additive system particularly useful for natural gas fueled engines |
US6756348B2 (en) | 2001-11-29 | 2004-06-29 | Chevron Oronite Company Llc | Lubricating oil having enhanced resistance to oxidation, nitration and viscosity increase |
US20030224948A1 (en) * | 2002-02-14 | 2003-12-04 | Dam Willem Van | Lubricating oil additive comprising EC-treated succinimide, borated dispersant and corrosion inhibitor |
DE60232788D1 (en) * | 2002-07-30 | 2009-08-13 | Chevron Oronite Sa | Hydrated alkali metal borate and hexagonal boron nitride additive composition for gear oils |
US20040235682A1 (en) * | 2003-05-22 | 2004-11-25 | Chevron Oronite Company Llc | Low emission diesel lubricant with improved corrosion protection |
ES2403780T3 (en) * | 2003-11-28 | 2013-05-21 | Chevron Oronite S.A. | Composition of additive for transmission oil |
US7875576B2 (en) * | 2004-07-29 | 2011-01-25 | Chevron Oronite Company Llc | Lubricating oil composition for internal combustion engines |
SG188788A1 (en) | 2004-12-09 | 2013-04-30 | Lubrizol Corp | Process of preparation of an additive and its use |
US7745542B2 (en) * | 2005-04-29 | 2010-06-29 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
EP1757673B1 (en) | 2005-08-23 | 2020-04-15 | Chevron Oronite Company LLC | Lubricating oil composition for internal combustion engines |
US7618928B2 (en) * | 2005-08-31 | 2009-11-17 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
EP1803771B1 (en) * | 2005-12-28 | 2017-12-06 | Bridgestone Corporation | A rubber composition having good wet-traction properties and a low aromatic-oil content |
US7858566B2 (en) | 2006-10-27 | 2010-12-28 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
US7816309B2 (en) * | 2006-10-27 | 2010-10-19 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
US8067347B2 (en) * | 2006-10-27 | 2011-11-29 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
US7820604B2 (en) | 2006-10-27 | 2010-10-26 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
US7820605B2 (en) * | 2006-10-27 | 2010-10-26 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
US7928044B2 (en) * | 2006-10-27 | 2011-04-19 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
US7700673B2 (en) * | 2006-12-22 | 2010-04-20 | Bridgestone Corporation | Reduced oil rubber compositions including N-substituted polyalkylene succinimide derivates and methods for preparing such compositions |
US20090093384A1 (en) * | 2007-10-03 | 2009-04-09 | The Lubrizol Corporation | Lubricants That Decrease Micropitting for Industrial Gears |
CN103524804B (en) | 2007-12-31 | 2017-03-29 | 株式会社普利司通 | Introduce the method that the metallic soap and metallic soap of rubber composition introduce rubber composition |
US8455568B2 (en) * | 2008-04-25 | 2013-06-04 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
EP2294127B1 (en) * | 2008-06-26 | 2016-04-20 | Bridgestone Corporation | Rubber compositions including metal-functionalized polyisobutylene derivatives and methods for preparing such compositions |
US9029304B2 (en) * | 2008-09-30 | 2015-05-12 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
US8153566B2 (en) * | 2008-09-30 | 2012-04-10 | Cherron Oronite Company LLC | Lubricating oil compositions |
US20100160193A1 (en) * | 2008-12-22 | 2010-06-24 | Chevron Oronite LLC | Additive composition and method of making the same |
US20100160192A1 (en) * | 2008-12-22 | 2010-06-24 | Chevron Oronite LLC | lubricating oil additive composition and method of making the same |
US8859473B2 (en) * | 2008-12-22 | 2014-10-14 | Chevron Oronite Company Llc | Post-treated additive composition and method of making the same |
US8389609B2 (en) * | 2009-07-01 | 2013-03-05 | Bridgestone Corporation | Multiple-acid-derived metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions |
CA2711626C (en) | 2009-07-31 | 2017-11-28 | Chevron Japan Ltd. | Friction modifier and transmission oil |
US9803060B2 (en) * | 2009-09-10 | 2017-10-31 | Bridgestone Corporation | Compositions and method for making hollow nanoparticles from metal soaps |
US8933001B2 (en) | 2010-03-31 | 2015-01-13 | Chevron Oronite Company Llc | Method for improving fluorocarbon elastomer seal compatibility |
US8901050B2 (en) | 2010-03-31 | 2014-12-02 | Chevron Oronite Company Llc | Method for improving copper corrosion performance |
US8802755B2 (en) | 2011-01-18 | 2014-08-12 | Bridgestone Corporation | Rubber compositions including metal phosphate esters |
JP6313775B2 (en) | 2012-11-02 | 2018-04-18 | 株式会社ブリヂストン | Rubber composition containing metal carboxylate and method for preparing the same |
CN104449977A (en) | 2013-09-23 | 2015-03-25 | 雪佛龙日本有限公司 | Fuel economy engine oil composition |
US9499765B2 (en) | 2015-03-23 | 2016-11-22 | Chevron Japan Ltd. | Lubricating oil compositions for construction machines |
US20160281020A1 (en) | 2015-03-23 | 2016-09-29 | Chevron Japan Ltd. | Lubricating oil compositions for construstion machines |
US10344245B2 (en) | 2016-10-25 | 2019-07-09 | Chevron Oronite Technology B.V. | Lubricating oil compositions comprising a biodiesel fuel and a dispersant |
US10781394B2 (en) | 2016-10-25 | 2020-09-22 | Chevron Oronite Technology B.V. | Lubricating oil compositions comprising a biodiesel fuel and a Mannich condensation product |
EP3625316B1 (en) | 2017-05-19 | 2023-08-23 | Chevron Oronite Company LLC | Dispersants, method of making, and using same |
US10604719B2 (en) | 2018-02-22 | 2020-03-31 | Chevron Japan Ltd. | Lubricating oils for automatic transmissions |
EP3911723B1 (en) | 2019-01-17 | 2024-05-08 | The Lubrizol Corporation | Traction fluids |
JP2023535706A (en) | 2020-07-23 | 2023-08-21 | シェブロン・オロナイト・カンパニー・エルエルシー | Heteroaromatic glycidyl ether post-treated succinimide dispersants exhibiting good soot disposal performance |
CA3189296A1 (en) | 2020-07-23 | 2022-01-27 | Chevron Oronite Company Llc | Succinimide dispersants post-treated with aromatic glycidyl ethers that exhibit good soot handling performance |
AU2021340009A1 (en) | 2020-09-14 | 2023-03-30 | Chevron Japan Ltd. | Lubricating oil containing alkyl phosphonic acid |
WO2023144721A1 (en) | 2022-01-25 | 2023-08-03 | Chevron Japan Ltd. | Lubricating oil composition |
WO2023156989A1 (en) | 2022-02-21 | 2023-08-24 | Chevron Oronite Company Llc | Lubricating oil composition |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2490744A (en) * | 1947-02-08 | 1949-12-06 | Socony Vacuum Oil Co Inc | Antirust agent |
US2604451A (en) * | 1948-09-16 | 1952-07-22 | Gulf Research Development Co | Mineral oil compositions |
US2638450A (en) * | 1950-01-17 | 1953-05-12 | Socony Vacuum Oil Co Inc | Reaction products of nu-alkylated polyalkylenepolyamines and alkenyl succinic acid anhydrides |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2540800A (en) * | 1947-02-08 | 1951-02-06 | Socony Vacuum Oil Co Inc | Antirust agent |
US2628942A (en) * | 1951-06-27 | 1953-02-17 | Texas Co | Lubricating oils containing metal derivatives of cyclic imides |
US2904548A (en) * | 1957-01-28 | 1959-09-15 | Geschickter Fund Med Res | N-substituted-3-azabicyclo [3:3:0] octane-2, 4-diones and salts thereof |
-
0
- NL NL255193D patent/NL255193A/xx unknown
-
1959
- 1959-08-24 US US835391A patent/US3024195A/en not_active Expired - Lifetime
- 1959-08-24 US US835389A patent/US3024237A/en not_active Expired - Lifetime
-
1960
- 1960-08-03 GB GB26926/60A patent/GB934401A/en not_active Expired
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2490744A (en) * | 1947-02-08 | 1949-12-06 | Socony Vacuum Oil Co Inc | Antirust agent |
US2604451A (en) * | 1948-09-16 | 1952-07-22 | Gulf Research Development Co | Mineral oil compositions |
US2638450A (en) * | 1950-01-17 | 1953-05-12 | Socony Vacuum Oil Co Inc | Reaction products of nu-alkylated polyalkylenepolyamines and alkenyl succinic acid anhydrides |
Cited By (104)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3172856A (en) * | 1965-03-09 | Copolymers of n-alkyl piperazine acry- late and alkyl acrylate and lubricat- ing oils containing them | ||
US3219666A (en) * | 1959-03-30 | 1965-11-23 | Derivatives of succinic acids and nitrogen compounds | |
US3278550A (en) * | 1959-03-30 | 1966-10-11 | Lubrizol Corp | Reaction products of a hydrocarbonsubstituted succinic acid-producing compound, an amine and an alkenyl cyanide |
US3154560A (en) * | 1961-12-04 | 1964-10-27 | Monsanto Co | Nu, nu'-azaalkylene-bis |
US3194812A (en) * | 1962-08-31 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-para amino-phenyl succinimide |
US3185704A (en) * | 1962-09-04 | 1965-05-25 | Exxon Research Engineering Co | Formamide of mono-alkenyl succinimide |
US3184474A (en) * | 1962-09-05 | 1965-05-18 | Exxon Research Engineering Co | Reaction product of alkenyl succinic acid or anhydride with polyamine and polyhydricmaterial |
US3194814A (en) * | 1962-10-18 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-allyl succinimide |
US3194813A (en) * | 1962-10-18 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-omega amino hexylsuccinimide |
US3224975A (en) * | 1962-12-03 | 1965-12-21 | Ethyl Corp | Lubricating oil compositions |
US3224968A (en) * | 1962-12-03 | 1965-12-21 | Ethyl Corp | Lubricating oil compositions |
US3307928A (en) * | 1963-01-30 | 1967-03-07 | Exxon Research Engineering Co | Gasoline additives for enhancing engine cleanliness |
US3200075A (en) * | 1963-02-19 | 1965-08-10 | California Research Corp | Lactone amides in lubricating oils |
US3200076A (en) * | 1963-03-28 | 1965-08-10 | California Research Corp | Polypiperazinyl succinimides in lubricating oils |
US3502677A (en) * | 1963-06-17 | 1970-03-24 | Lubrizol Corp | Nitrogen-containing and phosphorus-containing succinic derivatives |
US3312619A (en) * | 1963-10-14 | 1967-04-04 | Monsanto Co | 2-substituted imidazolidines and their lubricant compositions |
US3367943A (en) * | 1963-11-01 | 1968-02-06 | Exxon Research Engineering Co | Process for preparing oil soluble additives which comprises reacting a c2 to c5 alkylene oxide with (a) reaction product of an alkenylsuccinic anhydride and an aliphaticpolyamine (b) reaction product of alkenylsuccinic anhydride, a c1 to c30 aliphatic hydrocarbon carboxylic acid and an aliphatic polyamine |
US3223625A (en) * | 1963-11-12 | 1965-12-14 | Exxon Research Engineering Co | Colloidal molybdenum complexes and their preparation |
US3449249A (en) * | 1964-05-08 | 1969-06-10 | Shell Oil Co | Lubricant compositions |
US3311558A (en) * | 1964-05-19 | 1967-03-28 | Rohm & Haas | N-alkylmorpholinone esters of alkenylsuccinic anhydrides |
US3272746A (en) * | 1965-11-22 | 1966-09-13 | Lubrizol Corp | Lubricating composition containing an acylated nitrogen compound |
US3389083A (en) * | 1967-01-26 | 1968-06-18 | Chevron Res | Lubricants containing alkali metal dithiophosphates |
US3424684A (en) * | 1967-03-10 | 1969-01-28 | Texaco Inc | Lubricant containing polymeric product of alkenyl succinic anhydride and hydroxy containing piperazine derivative |
US3426738A (en) * | 1967-10-16 | 1969-02-11 | Chevron Res | Method of operation and lubricant for closed emission internal combustion engines |
US4465606A (en) * | 1982-07-22 | 1984-08-14 | Union Oil Company Of California | Stabilization of hydrocarbon oil |
US4486573A (en) * | 1982-08-09 | 1984-12-04 | The Lubrizol Corporation | Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4613342A (en) * | 1982-08-09 | 1986-09-23 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4489194A (en) * | 1982-08-09 | 1984-12-18 | The Lubrizol Corporation | Carboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4559155A (en) * | 1982-08-09 | 1985-12-17 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4564460A (en) * | 1982-08-09 | 1986-01-14 | The Lubrizol Corporation | Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4575526A (en) * | 1982-08-09 | 1986-03-11 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same |
US4596663A (en) * | 1982-08-09 | 1986-06-24 | The Lubrizol Corporation | Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4471091A (en) * | 1982-08-09 | 1984-09-11 | The Lubrizol Corporation | Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4623684A (en) | 1982-08-09 | 1986-11-18 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4749505A (en) * | 1985-07-08 | 1988-06-07 | Exxon Chemical Patents Inc. | Olefin polymer viscosity index improver additive useful in oil compositions |
US4946612A (en) * | 1986-06-09 | 1990-08-07 | Idemitsu Kosan Company Limited | Lubricating oil composition for sliding surface and for metallic working and method for lubrication of machine tools using said composition |
US4824884A (en) * | 1987-08-12 | 1989-04-25 | Pennwalt Corporation | Cyclic anhydride derivatives of hydrazide functionalized hindered amine light stabilizers |
US5041622A (en) * | 1988-04-22 | 1991-08-20 | The Lubrizol Corporation | Three-step process for making substituted carboxylic acids and derivatives thereof |
US5171466A (en) * | 1990-04-10 | 1992-12-15 | Ethyl Petroleum Additives Limited | Succinimide compositions |
US5232616A (en) * | 1990-08-21 | 1993-08-03 | Chevron Research And Technology Company | Lubricating compositions |
US5478367A (en) * | 1991-10-11 | 1995-12-26 | Exxon Chemical Patents Inc. | Fuel oil compositions |
US5330667A (en) * | 1992-04-15 | 1994-07-19 | Exxon Chemical Patents Inc. | Two-cycle oil additive |
US5356552A (en) * | 1993-03-09 | 1994-10-18 | Chevron Research And Technology Company, A Division Of Chevron U.S.A. Inc. | Chlorine-free lubricating oils having modified high molecular weight succinimides |
US6294506B1 (en) | 1993-03-09 | 2001-09-25 | Chevron Chemical Company | Lubricating oils having carbonated sulfurized metal alkyl phenates and carbonated metal alkyl aryl sulfonates |
EP0776963A1 (en) | 1995-12-01 | 1997-06-04 | Chevron Chemical Company | Polyalkylene succinimides and post-treated derivatives thereof |
EP0831104A2 (en) | 1996-08-20 | 1998-03-25 | Chevron Chemical Company | Novel dispersant terpolymers |
US20050181957A1 (en) * | 2002-05-30 | 2005-08-18 | Hiroaki Koshima | Lubricating oil additive composition for internal combustion engine |
US20060135375A1 (en) * | 2004-12-21 | 2006-06-22 | Chevron Oronite Company Llc | Anti-shudder additive composition and lubricating oil composition containing the same |
EP1674557A2 (en) | 2004-12-21 | 2006-06-28 | Chevron Oronite Company LLC | An anti-shudder additive composition and lubricating oil composition containing the same |
EP1728848A1 (en) | 2005-06-01 | 2006-12-06 | Infineum International Limited | Use of unsaturated olefin polymers to improve the compatibility between nitrile rubber seals and lubricating oil compositions |
US11599332B1 (en) | 2007-10-04 | 2023-03-07 | Great Northern Research, LLC | Multiple shell multi faceted graphical user interface |
EP2133406A1 (en) * | 2008-06-09 | 2009-12-16 | Idemitsu Kosan Co., Ltd. | Lubricating oil composition for internal combustion engine |
JP2009292998A (en) * | 2008-06-09 | 2009-12-17 | Idemitsu Kosan Co Ltd | Lubricating oil composition for internal combustion engine |
JP4597223B2 (en) * | 2008-06-09 | 2010-12-15 | 出光興産株式会社 | Lubricating oil composition for internal combustion engines |
EP2161326A1 (en) | 2008-09-05 | 2010-03-10 | Infineum International Limited | Lubricating oil compositions |
EP2163602A1 (en) | 2008-09-05 | 2010-03-17 | Infineum International Limited | A lubricating oil composition |
EP2620207A2 (en) | 2008-10-31 | 2013-07-31 | Calera Corporation | Non-cementitious compositions comprising CO2 sequestering additives |
US9133581B2 (en) | 2008-10-31 | 2015-09-15 | Calera Corporation | Non-cementitious compositions comprising vaterite and methods thereof |
EP2233554A1 (en) | 2009-03-27 | 2010-09-29 | Infineum International Limited | Lubricating oil compositions |
EP2290038A2 (en) | 2009-08-24 | 2011-03-02 | Infineum International Limited | A lubricating oil composition |
EP2290043A1 (en) | 2009-08-24 | 2011-03-02 | Infineum International Limited | A lubricating oil composition comprising metal dialkyldithiophosphate and carbodiimide |
EP2365049A1 (en) | 2009-08-24 | 2011-09-14 | Infineum International Limited | Use of a lubricating additive |
EP2390306A1 (en) | 2009-12-01 | 2011-11-30 | Infineum International Limited | A lubricating oil composition |
EP2363454A1 (en) | 2010-02-23 | 2011-09-07 | Infineum International Limited | A lubricating oil composition |
EP2371932A1 (en) | 2010-04-01 | 2011-10-05 | Infineum International Limited | A lubricating oil composition |
EP2374866A1 (en) | 2010-04-06 | 2011-10-12 | Infineum International Limited | A lubricating oil composition comprising alkoxylated phenol-formaldehyde condensate |
EP2453000A1 (en) | 2010-11-08 | 2012-05-16 | Infineum International Limited | Lubricating Oil Composition comprising a hydrogenated imide derived from a Diels-Alder adduct of maleic anhydride and a furan |
EP2457984A1 (en) | 2010-11-30 | 2012-05-30 | Infineum International Limited | A lubricating oil composition |
EP2559748A1 (en) | 2011-08-19 | 2013-02-20 | Infineum International Limited | Lubricating oil composition |
EP2584025A1 (en) | 2011-10-21 | 2013-04-24 | Infineum International Limited | Lubricating oil composition |
EP2692839A1 (en) | 2012-07-31 | 2014-02-05 | Infineum International Limited | A lubricating oil compostion comprising a corrosion inhibitor |
EP2692840A1 (en) | 2012-07-31 | 2014-02-05 | Infineum International Limited | Lubricating oil composition |
EP2913384A1 (en) | 2014-02-26 | 2015-09-02 | Infineum International Limited | A lubricating oil composition |
EP3034587A1 (en) | 2014-12-19 | 2016-06-22 | Infineum International Limited | Marine engine lubrication |
WO2017013257A1 (en) | 2015-07-22 | 2017-01-26 | Chevron Oronite Technology B.V. | Marine diesel cylinder lubricant oil compositions |
EP3192858A1 (en) | 2016-01-15 | 2017-07-19 | Infineum International Limited | Use of lubricating oil composition |
EP3222698A1 (en) | 2016-03-22 | 2017-09-27 | Infineum International Limited | Additive concentrates |
US11292980B2 (en) | 2016-03-22 | 2022-04-05 | Infineum International Ltd | Additive concentrates |
US11299690B2 (en) | 2016-03-22 | 2022-04-12 | Infineum International Ltd. | Additive concentrates |
EP3252130A1 (en) | 2016-06-03 | 2017-12-06 | Infineum International Limited | Additive package and lubricating oil composition |
EP3257921A1 (en) | 2016-06-14 | 2017-12-20 | Infineum International Limited | Lubricating oil additives |
WO2018041732A1 (en) | 2016-08-29 | 2018-03-08 | Chevron Oronite Technology B.V. | Marine diesel cylinder lubricant oil compositions |
WO2018069460A1 (en) | 2016-10-12 | 2018-04-19 | Chevron Oronite Technology B.V. | Marine diesel lubricant oil compositions |
WO2018073268A1 (en) | 2016-10-18 | 2018-04-26 | Chevron Oronite Technology B.V. | Marine diesel lubricant oil compositions |
EP3321347A1 (en) | 2016-11-14 | 2018-05-16 | Infineum International Limited | Lubricating oil additives based on overbased gemini surfactant |
EP3461877A1 (en) | 2017-09-27 | 2019-04-03 | Infineum International Limited | Improvements in and relating to lubricating compositions |
EP3473694A1 (en) | 2017-10-12 | 2019-04-24 | Infineum International Limited | Lubricating oil compositions |
EP3470499A1 (en) | 2017-10-16 | 2019-04-17 | Infineum International Limited | Use of detergent for internal compustion engine oil compositions |
EP3492567A1 (en) | 2017-11-29 | 2019-06-05 | Infineum International Limited | Lubricating oil additives |
EP3492566A1 (en) | 2017-11-29 | 2019-06-05 | Infineum International Limited | Lubricating oil additives |
EP3502217A1 (en) | 2017-11-29 | 2019-06-26 | Infineum International Limited | Lubricating oil compositions |
EP3770235A1 (en) | 2018-09-24 | 2021-01-27 | Infineum International Limited | Polymers and lubricating compositions containing polymers |
EP4039782A1 (en) | 2018-09-24 | 2022-08-10 | Infineum International Limited | Polymers and lubricating compositions containing polymers |
EP3741832A2 (en) | 2019-05-24 | 2020-11-25 | Infineum International Limited | Nitrogen-containing lubricating oil additives |
EP3851507A1 (en) | 2020-01-15 | 2021-07-21 | Infineum International Limited | Polymers and lubricating compositions containing polymers |
EP3926026A1 (en) | 2020-06-16 | 2021-12-22 | Infineum International Limited | Oil compositions |
EP4159832A1 (en) | 2021-10-04 | 2023-04-05 | Infineum International Limited | Lubricating oil compositions |
EP4174152A1 (en) | 2021-10-29 | 2023-05-03 | Infineum International Limited | Ionic liquid composition |
EP4174153A1 (en) | 2021-10-29 | 2023-05-03 | Infineum International Limited | Method of limiting chemical degradation due to nitrogen dioxide contamination |
EP4174154A1 (en) | 2021-10-29 | 2023-05-03 | Infineum International Limited | Method of limiting chemical degradation due to nitrogen dioxide contamination |
US11859149B2 (en) | 2021-10-29 | 2024-01-02 | Infineum International Limited | Ionic liquid composition |
US12006486B2 (en) | 2021-10-29 | 2024-06-11 | Infineum International Limited | Method of limiting chemical degradation due to nitrogen dioxide contamination |
US12031103B2 (en) | 2021-10-29 | 2024-07-09 | Infineum International Ltd | Method of limiting chemical degradation due to nitrogen dioxide contamination |
EP4303287A1 (en) | 2022-07-06 | 2024-01-10 | Infineum International Limited | Lubricating oil compositions |
Also Published As
Publication number | Publication date |
---|---|
NL255193A (en) | |
GB934401A (en) | 1963-08-21 |
US3024237A (en) | 1962-03-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3024195A (en) | Lubricating oil compositions of alkylpiperazine alkenyl succinimides | |
US3361673A (en) | Lubricating oil compositions containing alkenyl succinimides of tetraethylene pentamine | |
US3018250A (en) | Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides | |
US3131150A (en) | Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines | |
US3018247A (en) | Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends | |
US3185647A (en) | Lubricant composition | |
US3184411A (en) | Lubricants for reducing corrosion | |
US3154560A (en) | Nu, nu'-azaalkylene-bis | |
US3288714A (en) | Lubricating oil compositions containing alkenyl succinic anhydrides | |
US3216936A (en) | Process of preparing lubricant additives | |
US3438899A (en) | Alkenyl succinimide of tris (aminoalkyl) amine | |
US3278550A (en) | Reaction products of a hydrocarbonsubstituted succinic acid-producing compound, an amine and an alkenyl cyanide | |
CA1090320A (en) | Lubricating oil composition containing a dispersing- varnish inhibiting combination of nitrogen-containing additives | |
US3185645A (en) | Oxidation inhibited lubricants | |
US3525693A (en) | Alkenyl succinic polyglycol ether | |
US3261782A (en) | Alkylbutyrolactone-alpha-acetic acids | |
US3287271A (en) | Combined detergent-corrosion inhibitors | |
US3210283A (en) | Lubricant containing alkenyl succinimide and hydroxypolyamine | |
US3844958A (en) | Hydrocarbyl amines for lubricating oil detergents | |
US3200076A (en) | Polypiperazinyl succinimides in lubricating oils | |
US3185643A (en) | Oxidation resistant lubricants | |
US3200075A (en) | Lactone amides in lubricating oils | |
US3184412A (en) | Lubricants inhibited against oxidation | |
US3647694A (en) | Lubricating oil composition | |
US3152080A (en) | Amido-bis-imidazolines in lubricating oil compositions |