EP0092946B1 - Glycerol esters with oil-soluble copper compounds as fuel economy additives - Google Patents

Glycerol esters with oil-soluble copper compounds as fuel economy additives Download PDF

Info

Publication number
EP0092946B1
EP0092946B1 EP83302155A EP83302155A EP0092946B1 EP 0092946 B1 EP0092946 B1 EP 0092946B1 EP 83302155 A EP83302155 A EP 83302155A EP 83302155 A EP83302155 A EP 83302155A EP 0092946 B1 EP0092946 B1 EP 0092946B1
Authority
EP
European Patent Office
Prior art keywords
oil
copper
fuel economy
glycerol
composition
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
Application number
EP83302155A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0092946A3 (en
EP0092946A2 (en
Inventor
Phillip William Brewster
Clinton Richard Smith
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Exxon Research and Engineering Co filed Critical Exxon Research and Engineering Co
Publication of EP0092946A2 publication Critical patent/EP0092946A2/en
Publication of EP0092946A3 publication Critical patent/EP0092946A3/en
Application granted granted Critical
Publication of EP0092946B1 publication Critical patent/EP0092946B1/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04—Hydroxy 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/40—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms monocarboxylic
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/56—Acids of unknown or incompletely defined constitution
    • C10M129/58—Naphthenic 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/76—Esters containing free hydroxy or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/06—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing conjugated dienes
    • 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
    • C10M2207/02—Hydroxy 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027—Neutral 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/028—Overbased 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/09—Metal enolates, i.e. keto-enol metal complexes
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C10M2207/126—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/16—Naphthenic 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
    • C10M2207/287—Partial 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/26—Amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
    • C10M2217/023—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group the amino group containing an ester bond
    • 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
    • C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine 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
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbased sulfonic acid salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C10M2219/068—Thiocarbamate metal salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • 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
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • 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
    • 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
    • C10N2010/02—Groups 1 or 11

Definitions

  • This invention relates to lubricating oil compositions which exhibit marked improvements in fuel economy. More particularly, this invention relates to lubricating oil compositions which contain very minor proportions of a glycerol fatty acid ester fuel economy additive in combination with an oil-soluble organic copper compound.
  • the present invention concerns the use of glycerol fatty acid esters as such fuel economy additives, specifically glycerol esters of C 16- C 18 fatty acids in combination with oil-soluble copper organic compounds.
  • glycerol fatty acid esters as such fuel economy additives, specifically glycerol esters of C 16- C 18 fatty acids in combination with oil-soluble copper organic compounds.
  • British Application 2097813A published November 10, 1982, discloses the use of 0.05 to 0.2 wt.% glycerol partial esters of C16-C18 fatty acids as fuel economy additives.
  • the present invention is an improvement over said British application.
  • West German Application P-2949940 and P-2949910 of Chevron Research Company both published July 3,1980, disclose the use of glycerol fatty esters as fuel economy additives. These references state that the addition of 0.25 to 2 weight percent, preferably 0.40 to 1.25 weight percent, of a fatty acid ester will offer a fuel economy credit of 2-3 percent in both gasoline and diesel engines. Glycerol oleic acid esters are preferred.
  • West German Application P-2949940 illustrates the preferred embodiment showing the use of the glycerol ester at the same treat level in combination with zinc dihydrocarbyl dithiophosphate additives.
  • U.S. Patent 4,304,678 discloses hydroxyl-containing esters including glycerol oleates as being effective friction modifiers only at levels of 1-4 wt.% with no benefit observed at levels less than 1 % by wt. in oil.
  • the present invention is based upon the discovery that very low levels of glycerol esters; that is, up to about 0.2 percent by weight, in combination with certain amounts of oil-soluble organic copper compounds, provide enhanced performance of these fuel economy lubricating oils. No benefit is obtainable in using relatively higher amounts and in some cases substantial debits in terms of formulation stability or adverse performance may occur.
  • U.S. Patent 3,933,659 shows a multi-component functional fluid, one component of which can be a polyol ester friction modifier or a fatty acid amide friction modifier.
  • the primary use disclosed in that reference is for automatic transmission fluids.
  • U.S. Patent 3,273,981 discloses anti-wear additives comprising a mixture of dimer acids and a partial ester of a polyhydric alcohol, the additive being noted as improving lubricity as well as functioning in the anti-wear category.
  • U.S. Patent 3,112,271 discloses glycerol mono-oleate as an extreme pressure additive as does U.S.
  • U.S. 2,493,483 discloses marine engine lubricants which contain a partial ester of glycerol or other polyol fatty acid esters in amounts of from 0.05 to 1 percent.
  • oil-soluble copper compounds at levels of about 5 to 500 parts per million (ppm) of copper by weight, based on the total weight of lubricating oil composition, as a highly effective antioxidant is a relatively recent development of additive technology and is disclosed in European Published Application No. 0024146, published on February 25, 1981.
  • the present invention is based on the discovery that these copper compounds, when used in an oil in combination with glycerol esters, e.g. oleates, act cooperatively with the glycerol ester in substantially increasing the fuel economy of the formulated oil.
  • the cumulative effect observed would not be expected by adding the fuel economy credit obtained in oils which contain one or the other of the glycerol ester or copper compound. Data obtained therefore provide the basis for an unexpected additive effect upon fuel economy due to more effective lubrication of an internal combustion engine operated using the oils of the present invention.
  • German Democratic Republic Patents 145,469 and 145,470 disclose the reduction of wear and friction in iron/iron and iron/bronze friction interfaces using polyol or mineral oil lubricants containing copper compounds such as copper naphthenate, copper octoate, copper stearate and reaction products of lubricants themselves with copper, copper oxide and copper salts of inorganic acids. These references indicate that the friction reduction is achieved by deposition on the substrate being lubricated of a film reaction layer of copper with adequate adhesion properties. It is recommended in these references that the concentration of the copper compound in the lubricant provide a copper content of 0.001 to 5 volume % relative to the lubricant. These references however did not evaluate lubricating oil compositions for internal combustion engines.
  • fuel economy improving lubricating oil compositions for internal combustion engines which comprise an oil of lubricating viscosity and, as the fuel economy additive, a combination from 0.05 to 0.20 weight percent of a glycerol partial ester of a C 16 ⁇ C 18 fatty acid with from 5 to 500 ppm (parts per million) copper present in the form of an oil-soluble copper compound, preferably 60 to 200 ppm copper being present, based upon the weight of the total composition, the copper compound also functioning as an antioxidant.
  • the lubricating oil compositions of the present invention comprise both straight grade and multigrade lubricating oil formulations for both gasoline and diesel (compression ignition) engines.
  • the lubricating oil compositions will contain those additive systems formulated to meet the viscosity requirements or other specifications as required for qualification as a gasoline engine or diesel lubricating oil.
  • a straight grade lubricating oil formulation will normally contain conventional amounts of an ashless dispersant, a normal or basic metal detergent, an anti-wear additive and an antioxidant and a multi-grade oil will contain, in addition to the foregoing, a viscosity index improver or viscosity modifier.
  • very small proportions of other special purpose additives such as pour depressants, rust inhibitors, anti-foamants and the like are conventionally blended into lubricating oil compositions.
  • the ester component of the fuel economy additive of the present invention is preferably a glycerol mono- or diester of a saturated or unsaturated C 16 ⁇ C 18 fatty acid, such as oleic or linoleic acid.
  • Optimum efficiency has been found to be at about the 0.1 to 0.2 weight percent level and use in the excess of this amount may even be detrimental to the overall performance of the lubricating oil composition.
  • Oil-soluble copper components useful herein include both cuprous or cupric compounds which are oil-soluble under normal blending conditions in the oil additive package.
  • Particularly preferred are the copper salts of C, o -C 22 fatty acids, such as stearic or palmitic acid, but copper salts of unsaturated acids, such as oleic acid, linoleic acid, naphthenic acid of 200 ⁇ 500 molecular weight or synthetic carboxylic acids are preferred.
  • the particularly preferred embodiment is copper (cupric) oleate when present in an amount to provide about 100 to 150 ppm copper in the lubricating oil composition.
  • Suitable copper compounds include the same as those disclosed in said European Published Application 0024146 and these include copper dithiocarbamates of the formula (RR'NCSS) n CU where n is 1 or 2 and R and R' are the same or different C 1 -C 18 hydrocarbyl radicals, preferably C2-C,, alkyl, copper sulphonates, copper phenates and acetyl acetonates as well as copper dihydrocarbyl dithiophosphate, the hydrocarbyl being C 1 -C 18 and preferably C 2 -C B alkyl, such as a hexyl or isooctyl.
  • Crankcase oil formulations to which the present invention relates are those which contain a major amount of lubricating oil and effective amounts of conventional additives in addition to the aforesaid fuel economy additive, the copper compound serving the dual function of being both an antioxidant and, in combination with the glycerol oleate, a fuel economy additive.
  • Percentages of additives as described herein are by weight based on the total weight of lubricating oil formulation unless otherwise indicated.
  • additives comprise ashless dispersants typically nitrogen-containing dispersant, additives which are oil-soluble salts, amides, imides and esters made from high molecular weight mono- or di-carboxylic acids and various amines having an amino or heterocyclic nitrogen with at least one amido or hydroxy group capable of salt, amide or ester formation.
  • Preferred are the reaction products of polyolefin (C 2 -C S olefin), such as polyisobutenyl, succinic anhydride with an alkylene polyamine such as tetraethylenepentamine.
  • the polyisobutenyl portion has between 50 and 250 carbon atoms.
  • the alkylene polyamines are those represented by the formula: where n is 2 to 3 and m is a number from 0 to 10. Mixtures of alkylene polyamines which approximate tetraethylenepentamine are commercially available materials. Dispersants are used generally in amounts of from 0.1 to 10 wt.%, preferably in the range of 0.5 to 5 wt.%, based on the weight of the lubricating oil composition.
  • Detergents useful in the formulations include the normal, basic or overbased metal, that is, calcium, magnesium and so forth, salts of petroleum naphthenic acids, petroleum sulfonic acids, alkyl benzene sulfonic acids, alkyl phenols, alkylene-bis-phenol, oil-soluble fatty acids and the like.
  • the preferred materials are the normal or overbased calcium or magnesium phenates, sulfurized phenates and/or sulfonates, and these metal-containing detergent additives are typically used in amounts of from 1 to 3 wt.% based on the total weight of lubricating oil compositions.
  • Suitable pour point depressants which are usually present in amounts of 0.01 to 1 wt.%, include wax alkylated aromatic hydrocarbons, olefin polymers and copolymers, acrylate and methacrylate polymers and copolymers.
  • Anti-wear additives generally are the oil-soluble zinc dihydrocarbyl dithiophosphates having a least a total of 5 carbon atoms, the alkyl group being preferably C 2 -C 8 . These are typically present in amounts of from 0.01 to 5 wt.%, preferably 0.5 to 1.5 wt.%, in the lubricating oil.
  • Suitable conventional viscosity index improvers, or viscosity modifiers are the olefin polymers such as polybutene, ethylene-propylene copolymers, hydrogenated polymers and copolymers and terpolymers of styrene with isoprene and/or butadiene, polymers of alkyl acrylates or alkyl methacrylates, copolymers of alkyl methacrylates with N-vinyl pyrrolidone or dimethylaminoalkyl methacrylate, post-grafted polymers of ethylene-propylene with an active monomer, such as maleic anhydride, which may be further reacted with an alcohol or an alkylene polyamine, styrene-maleic anhydride polymers post-reacted with alcohols and amines and the like. These additives are used in amounts of 1.5% to 15% by wt., depending on the exact viscosity specifications desired.
  • antioxidants include phenols, hindered phenols, bis-phenols, sulfurized phenols, catechol, alkylated and sulfurized alkylated catechols, diphenylamine, alkylated diphenylamines and phenyl-1-naphthylamines, alkyl and aryl borates, phosphites and phosphates, trialkyl and triaryl dithiophosphates and the like.
  • Suitable hydrocarbon base stocks are those mineral oils of lubricating viscosity as measured by ASTM D-455 of from 2 to 40, preferably 5 to 20 centistokes at 99°C.
  • the reference oil used in this example was a formulated straight grade 20W30 crankcase mineral lubricating oil (corresponding to ASTM "HR" oil) to which was added 0.2 weight percent of a glycerol monooleate (GMO) fuel economy additive or 0.2 weight percent of a fuel economy additive being a mixture (GMO/GDO) of glycerol monooleate and glycerol dioleate in a weight ratio of 3 parts of GMO to 2 parts of GDO in said mixture.
  • GMO glycerol monooleate
  • GDO glycerol dioleate
  • the reference oil contained 2.10 wt.% dispersant, 1.10 wt.% antioxidant, 1.00 wt.% basic metal detergent, 1.95 wt.% anti-wear additive, 0.21 wt.% pour depressant and 0.001 wt.% anti-foam agent.
  • This type of reference oil which is generally accepted by the industry for establishing fuel economy data, provides a reproducible baseline against which fuel economy credits may be measured and is considered to provide test results which accurately reflect the effect of a given fuel economy additive.
  • Example 6 This will be demonstrated in Example 6.
  • Example 1-4 and 6 are presented here to illustrate these principles.
  • the LEFET test was carried out using an Oil * equivalent to the HR straight grade oil of Example 1 except that 0.3 wt.% of a 40 wt.% solution of copper oleate in mineral oil, which is equivalent to 120 ppm copper was used in place of the anti-oxidant reported in Example 1.
  • the LEFET results for this test are below in Table IV:
  • oils containing both the oil-soluble organic copper compound and glycerol ester friction modifier would exhibit any complementary effect
  • different oils were formulated and tested in Ford 2.3 liter 4-cylinder engine.
  • the purpose of these tests was to evaluate the increase in fuel economy credits when the copper compound and the glycerol ester were combined over the credits obtained with these additives separately in the same engine.
  • Fuel economy credit values will vary among engines of differing sizes. This is due to the inherent differences in engine design and operating conditions. It is known therefore that the values for a 2.3 liter 4-cylinder engine will be lower than fuel economy credit values for a 5 liter 8-cylinder used in these examples.
  • balance is basestock mineral oil.
  • Oil D represents the advantage of this invention. Oils B, C, E show the maximum values one can expect to obtain based on the credits due only to the copper compound. Oil D, however, achieves a value of 0.9%. This result is not expected because it is known, as a general principle, that merely increasing the treatment level of a given fuel economy additive does not increase the credit obtained.
  • Oil G was a formulated lubricating oil having 4 wt.% dispersant, 1 wt.% overbased metal sulfonate, 1.5 wt.% antioxidant and 2 wt.% anti-wear additive.
  • Oil H was the same as Oil G, except for the inclusion of 0.1 wt.% dimerized linoleic acid ester of diethylene glycol as disclosed in U.S. Patent 4,105,571.
  • Oil I was the same as Oil G except 0.2 wt.% of the GMO/GDO ester was added.
  • Oil J was the same as Oil G except both 0.1 wt.% of the dimerized linoleic acid ester and 0.2 wt.% of the GMO/GDO were added. Fuel economy results for these four oils are shown below in Table VI.
  • Oil K contained 5.5 wt.% dispersant, 1 wt.% overbased metal sulfonate, 1.4 wt.% anti-wear additive and 1 wt.% anti-oxidant.
  • Oil L was the same as Oil K with 0.3 wt.% of a 40 wt.% solution of copper oleate (120 ppm copper) included and Oil M was the same as Oil L except 0.1 wt.% of the GMO/GDO glycerol oleate was included.
  • Fuel economy credits are in Table VII below.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)
EP83302155A 1982-04-22 1983-04-15 Glycerol esters with oil-soluble copper compounds as fuel economy additives Expired EP0092946B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US37100882A 1982-04-22 1982-04-22
US371008 1982-04-22

Publications (3)

Publication Number Publication Date
EP0092946A2 EP0092946A2 (en) 1983-11-02
EP0092946A3 EP0092946A3 (en) 1985-08-14
EP0092946B1 true EP0092946B1 (en) 1988-03-16

Family

ID=23462117

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83302155A Expired EP0092946B1 (en) 1982-04-22 1983-04-15 Glycerol esters with oil-soluble copper compounds as fuel economy additives

Country Status (4)

Country Link
EP (1) EP0092946B1 (enrdf_load_stackoverflow)
JP (1) JPS58191795A (enrdf_load_stackoverflow)
CA (1) CA1205451A (enrdf_load_stackoverflow)
DE (1) DE3376016D1 (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6750185B2 (en) 2001-04-02 2004-06-15 Tonengeneral Sekiyu K.K. Lubricating oil composition for internal combustion engines
US11407958B2 (en) 2018-10-29 2022-08-09 Castrol Limited Lubricant compositions
US20230079734A1 (en) * 2020-02-21 2023-03-16 Ab Nanol Technologies Oy A method for preparing an organometallic salt composition, as well as the use of the composition in a lubricant additive

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2097813B (en) * 1981-05-06 1985-09-25 Exxon Research Engineering Co Glycerol esters in lubricating oils as fuel economy additives
US4705641A (en) * 1986-09-15 1987-11-10 Exxon Research And Engineering Company Copper molybdenum salts as antioxidants
GB8704683D0 (en) * 1987-02-27 1987-04-01 Exxon Chemical Patents Inc Low phosphorus/zinc lubricants
US4915857A (en) * 1987-05-11 1990-04-10 Exxon Chemical Patents Inc. Amine compatibility aids in lubricating oil compositions
US5049290A (en) * 1987-05-11 1991-09-17 Exxon Chemical Patents Inc. Amine compatibility aids in lubricating oil compositions
US4956108A (en) * 1987-07-29 1990-09-11 Mobil Oil Corporation Copper salts of thiodipropionic acid derivatives as antioxidant additives process of making the same and fuel composition thereof
US5013467A (en) * 1987-09-16 1991-05-07 Exxon Chemical Patents Inc. Novel oleaginous composition additives for improved rust inhibition
US5141657A (en) * 1987-10-02 1992-08-25 Exxon Chemical Patents Inc. Lubricant compositions for internal combustion engines
US5320765A (en) * 1987-10-02 1994-06-14 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines
US5102566A (en) * 1987-10-02 1992-04-07 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines (pt-727)
US4957651A (en) * 1988-01-15 1990-09-18 The Lubrizol Corporation Mixtures of partial fatty acid esters of polyhydric alcohols and sulfurized compositions, and use as lubricant additives
US5021173A (en) * 1988-02-26 1991-06-04 Exxon Chemical Patents, Inc. Friction modified oleaginous concentrates of improved stability
US4952328A (en) * 1988-05-27 1990-08-28 The Lubrizol Corporation Lubricating oil compositions
US4981602A (en) * 1988-06-13 1991-01-01 The Lubrizol Corporation Lubricating oil compositions and concentrates
US4938881A (en) * 1988-08-01 1990-07-03 The Lubrizol Corporation Lubricating oil compositions and concentrates
US4957649A (en) * 1988-08-01 1990-09-18 The Lubrizol Corporation Lubricating oil compositions and concentrates
US5286394A (en) * 1989-06-27 1994-02-15 Ethyl Corporation Fuel economy and oxidation inhibition in lubricant compositions for internal combustion engines
US5244591A (en) * 1992-03-23 1993-09-14 Chevron Research And Technology Company Lubricating oil compositions for internal combustion engines having silver bearing parts
US6254849B1 (en) * 1999-07-28 2001-07-03 Chevron U.S.A. Inc. Zeolite SSZ-52
GB2359092A (en) * 2000-02-14 2001-08-15 Exxonmobil Res & Eng Co Lubricating oils having improved fuel economy retention properties
US6892531B2 (en) * 2003-04-02 2005-05-17 Julius J. Rim System for and methods of operating diesel engines to reduce harmful exhaust emissions and to improve engine lubrication
EP1925655A1 (en) 2006-11-22 2008-05-28 Infineum International Limited Lubricating oil compositions
EP2161326A1 (en) 2008-09-05 2010-03-10 Infineum International Limited Lubricating oil compositions
EP2390306B1 (en) 2009-12-01 2019-08-14 Infineum International Limited A lubricating oil composition
MX344361B (es) 2010-06-25 2016-12-14 Castrol Ltd * Usos y composiciones.
PL2633009T3 (pl) 2010-10-26 2016-10-31 Niewodny środek smarny i kompozycje paliwowe zawierające estry kwasów tłuszczowych kwasów hydroksykarboksylowych, i ich zastosowania
JP6027578B2 (ja) * 2013-08-30 2016-11-16 良光 長井 潤滑促進液
EP3115443A1 (en) 2015-07-07 2017-01-11 Ab Nanol Technologies Oy Organometallic salt composition, a method for its preparation and a lubricant additive composition
EP3252130B1 (en) 2016-06-03 2021-02-17 Infineum International Limited Additive package and lubricating oil composition
CN107964441A (zh) * 2017-10-19 2018-04-27 山东源根石油化工有限公司 一种有机铜抗氧剂以及含有该有机铜抗氧剂的柴油机油

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2911367A (en) * 1957-07-01 1959-11-03 Gulf Oil Corp Mineral lubricating oil composition
CA1137463A (en) * 1978-12-18 1982-12-14 Thomas V. Liston Mileage-improving lubricating oil
GB2056482A (en) * 1979-08-13 1981-03-18 Exxon Research Engineering Co Lubricating oil compositions
GB2097813B (en) * 1981-05-06 1985-09-25 Exxon Research Engineering Co Glycerol esters in lubricating oils as fuel economy additives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6750185B2 (en) 2001-04-02 2004-06-15 Tonengeneral Sekiyu K.K. Lubricating oil composition for internal combustion engines
US11407958B2 (en) 2018-10-29 2022-08-09 Castrol Limited Lubricant compositions
US20230079734A1 (en) * 2020-02-21 2023-03-16 Ab Nanol Technologies Oy A method for preparing an organometallic salt composition, as well as the use of the composition in a lubricant additive

Also Published As

Publication number Publication date
EP0092946A3 (en) 1985-08-14
JPH0377837B2 (enrdf_load_stackoverflow) 1991-12-11
CA1205451A (en) 1986-06-03
DE3376016D1 (en) 1988-04-21
EP0092946A2 (en) 1983-11-02
JPS58191795A (ja) 1983-11-09

Similar Documents

Publication Publication Date Title
EP0092946B1 (en) Glycerol esters with oil-soluble copper compounds as fuel economy additives
US4683069A (en) Glycerol esters as fuel economy additives
US4686054A (en) Succinimide lubricating oil dispersant
US5114603A (en) Friction reducing lubricating oil composition
JP3993901B2 (ja) 潤滑油組成物
EP0814148B1 (en) Low phosphorous engine oil compositions and additive compositions
US4158633A (en) Lubricating oil
JP4080056B2 (ja) 改良された非摩耗性油圧流体を用いた油圧装置
CA2549269C (en) Crankcase lubricating oil composition for protection of silver bearings in locomotive diesel engines
US4406803A (en) Method for improving fuel economy of internal combustion engines
CA1190216A (en) Succinimide lubricating oil dispersant
CA1174660A (en) Glycerol esters as fuel economy additives
US5866520A (en) Lubricant composition suitable for direct fuel injected, crankcase-scavenged two-stroke cycle engines
Bardasz et al. Additives for crankcase lubricant applications
US4800032A (en) Aliphatic hydrocarbon substituted aromatic hydrocarbons to control black sludge in lubricants
US4557841A (en) Lubricant additive concentrate
US5244591A (en) Lubricating oil compositions for internal combustion engines having silver bearing parts
US4356097A (en) Alkylphosphonate lubricating oil
CN1229477C (zh) 液压用液体
US4938883A (en) Overbased alkaline earth alkenyl succinates as a silver-mild source of alkalinity for heavy duty diesel engines
US6001779A (en) Lubricating oil composition having an ashless wear inhibitor
US4246125A (en) Lubricating oil and fuel composition
JPH0148319B2 (enrdf_load_stackoverflow)
JPH0570786A (ja) アルコールエンジン用潤滑油組成物
LAMB EWA A. BARDASZ

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19830428

AK Designated contracting states

Designated state(s): BE DE FR GB IT NL SE

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Designated state(s): BE DE FR GB IT NL SE

17Q First examination report despatched

Effective date: 19860731

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE FR GB IT NL SE

ITF It: translation for a ep patent filed
REF Corresponds to:

Ref document number: 3376016

Country of ref document: DE

Date of ref document: 19880421

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
ITTA It: last paid annual fee
EAL Se: european patent in force in sweden

Ref document number: 83302155.3

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 19960409

Year of fee payment: 14

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19970314

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19970322

Year of fee payment: 15

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19970416

EUG Se: european patent has lapsed

Ref document number: 83302155.3

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19981101

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 19981101

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19990202

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20000329

Year of fee payment: 18

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20010312

Year of fee payment: 19

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20010319

Year of fee payment: 19

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010430

BERE Be: lapsed

Owner name: EXXON RESEARCH AND ENGINEERING CY

Effective date: 20010430

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20020415

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20020415

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20021231

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST