US2685567A - Lubricant composition containing alkyl-mercaptoalkyl phosphites - Google Patents

Lubricant composition containing alkyl-mercaptoalkyl phosphites Download PDF

Info

Publication number
US2685567A
US2685567A US259015A US25901551A US2685567A US 2685567 A US2685567 A US 2685567A US 259015 A US259015 A US 259015A US 25901551 A US25901551 A US 25901551A US 2685567 A US2685567 A US 2685567A
Authority
US
United States
Prior art keywords
phosphite
base
incorporated
phosphites
lubricant
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US259015A
Inventor
Harman Denham
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.)
Shell Development Co
Original Assignee
Shell Development 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 Shell Development Co filed Critical Shell Development Co
Priority to US259015A priority Critical patent/US2685567A/en
Application granted granted Critical
Publication of US2685567A publication Critical patent/US2685567A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04Phosphate esters
    • C10M137/10Thio derivatives
    • C10M137/105Thio derivatives not containing metal
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026Butene
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/16Paraffin waxes; Petrolatum, e.g. slack wax
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027Neutral salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/046Hydroxy ethers
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125Carboxylix 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/14Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/14Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/141Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/14Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/142Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/14Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/144Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/14Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/146Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent of thirty or more carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/18Tall oil acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/20Rosin acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/22Acids obtained from polymerised unsaturated acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/24Epoxidised acids; Ester derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/284Esters of aromatic monocarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/285Esters of aromatic polycarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
    • C10M2207/404Fatty vegetable or animal oils obtained from genetically modified species
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular 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
    • C10M2209/082Macromolecular 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 monocarboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/101Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044Acids; Salts or esters thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06Perfluorinated compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/10Amides of carbonic or haloformic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/10Amides of carbonic or haloformic acids
    • C10M2215/102Ureas; Semicarbazides; Allophanates
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/16Nitriles
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/20Containing nitrogen-to-oxygen bonds
    • C10M2215/202Containing nitrogen-to-oxygen bonds containing nitro groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/20Containing nitrogen-to-oxygen bonds
    • C10M2215/204Containing nitrogen-to-oxygen bonds containing nitroso groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/042Sulfate esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/064Thiourea type compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088Neutral salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089Overbased salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/042Metal salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/043Ammonium or amine salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/047Thioderivatives not containing metallic elements
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/10Phosphatides, e.g. lecithin, cephalin
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00Organic 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
    • C10M2227/06Organic compounds derived from inorganic acids or metal salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00Organic 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
    • C10M2227/08Organic 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 having metal-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/02Groups 1 or 11
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/04Groups 2 or 12
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/06Groups 3 or 13
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/08Groups 4 or 14
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/10Groups 5 or 15
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/12Groups 6 or 16
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/14Group 7
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/16Groups 8, 9, or 10
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2060/00Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/04Oxidation, e.g. ozonisation

Definitions

  • This invention relates to lubricants having imformed by the removal of hydrogen atoms from proved stability and lubricating properties.
  • saturated aliphatic hydrocarbons X is a non- More particularly, this invention pertains to comoygen .chalkogen element, preferably sulfur and pounded lubricants having incorporated therein 1 is an integer of from 1 to 4.
  • Additive agents of this invention can be pretemperature anti-oxidant and extreme pressure pared by any suitable means such as the methods properties.
  • Any suitable means such as the methods properties.
  • Serial Various lubricants whether of natural and/or No. 381,561 filed July 13, 1948 and which has synthetic origin such as petroleum hydrocarbons, matured into U. S. Patent No. 2,587,616 of which fixed fats and oils and fractions thereof as Well this application is a continuation-in-part, are
  • One object of this invention is to impart extreme pressure properties to base lubricants and inhibit their oxidation over a wide temperature range. Another object of this invention is to prevent oxidation of base lubricants. Still another object of this invention is to produce an improved lubricant of outstanding stability and Bis 3 cyclohexylmercaptopropyl) phosphite extreme pressure properties by incorporating in Tris 3-c cloheximercaptopropyl) phosphite said base lviloriciant at, pargicular type of additive 3o 3 cyclopgmylmeicapto 2 methy1propy1 phosphite free from o jec iona 1e 0 ors.
  • the preferred class of compounds comprises the alkyl-mercaptoalkyl phosphites, which Dthexyl 3octylmercapto'z'propylbutyl phosphite are aliphatic phosphites in which the aliphatic DIOYPIOheXYI 3 cyclohexylmercaptopropyl phos' radicals replacing the hydrogen atoms of the phlte hydroxyl groups of phosphorous acid, are of the -ethylhexyl 3-amyselenylpropyl phosphite general formula in which R and 3 amylmercaptopropyl dithio dicyclohexyl phosare polar or non-polar substituted non-aromatic Dhite hydrocarbyl radicals and preferably represent Chlorobenzyl bis(3-amylmercaptopropyl) phosmono and divalent 01-015 hydrocarbon radicals phite 3 Chloropheny
  • non-oxygen chalkogen ether containing phosphites of this invention can be used to improve base lubricants, in concentrations varying from 0.001% to 20% and preferably from 0.1% to 5% by weight.
  • Organic bases include various nitrogen bases as primary, secondary, tertiary amines and quaternary ammonium compounds, e. g., benzyl trirnethyl ammonium hydroxide.
  • detergent-forming acids are the fatty acids of say, 10 to 30 carbon atoms, tall-oil acids, rosin acids, wool-fat acids, paraffin-wax acids (produced by oxidation of paraifin Wax), chlorinated fatty acids, aromatic hydroxy fatty acids, paraffin-wax benzoic acids, various alkyl salicyclic acids, phthalic acid monoesters, aromatic keto acids, aromatic ether acids, diphenols such as di-(alkylphenol) sulfides and disulfides,
  • methylene bis-alkyl phenols such as may be produced by treatment of alkyl aryl hydrocarbons or high-boiling petroleum oils with sulfuric acid; sulfuric acid monoesters; phosphoric, arsonic and antimony acid monoand diesters, including the corresponding thiophosphoric and arsonic acids and the like.
  • alkaline earth phosphate di-esters including the thiophosphate (ii-esters; the alkaline earth diphenolates, specifically, the calcium and barium salts of diphenol monoand poly-sulfides.
  • Non-metallic detergents include compounds such as the phosphatides (lecithin and cephalin) certain fatty oils such as rapeseed oils, Voltolized fatty or mineral oils and the like.
  • An excellent detergent for the present purpose is the calcium salt of oil-solule petroleum sulfonic acids. This may be present advantageously in the amount of about 0.025% to 0.2% sulfate ash. Also, alkaline metal salts of alkyl phenolaldehyde condensation products are excellent detergents.
  • Corrosion inhibitors or anti-rusting compounds may also be present, such as dicarboxylic acids of 16 or more carbon atoms; alkali metal and alkaline earth salts of sulfonic acids and fatty acids, organic compounds containing an acidic radical in close proximity to a nitrile, nitro, or nitroso group (e. g., alpha-cyanostearic acid), glycidyl phenyl ether, wax disulfide, etc.
  • Additional ingredients may comprise oil-soluble urea or thiourea derivatives, e. g., urethanes, allophanates, carbazides, carbazones, etc., polyisobutylene polymers, unsaturated polymerized esters of fatty acids and monohydric alcohols and other high-molecular-weight oil-soluble compounds.
  • oil-soluble urea or thiourea derivatives e. g., urethanes, allophanates, carbazides, carbazones, etc.
  • polyisobutylene polymers unsaturated polymerized esters of fatty acids and monohydric alcohols and other high-molecular-weight oil-soluble compounds.
  • the amount of additive used may vary from 0.01 to 2% or higher. However, substantial; improvement is obtained by using amounts ranging from 0.1 to 0.5% in combination with the primary additive of this invention.
  • An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of tri(3-amylmercaptopropyl) phosphite.
  • An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of bis(3-amylmercaptopropyl) phosphite.
  • An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of tris(3-cyclohexylmercaptopropyl) phosphite.
  • An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of 5-pentadecyl1nercaptopentyl phosphite.
  • An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of 3-cyclophenylmercapto-2-methylpropyl phosphite.
  • An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufiicient to stabilize said oil base against oxidation deterioration of tris(3-amylmercapto propyl) phosphite.
  • An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sunicient to stabilize said oil base against oxidation deterioration of bis(3-amylmercapto propyl) phosphite.
  • An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufficient to stabilize said oil base against oxidation deterioration of tris(3-cyclohexylmercaptopropyl) phosphite.
  • An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufiicient to stabilize said oil base against oxidation deterioration of 5-pentadecyl mercaptopentyl phosphite.
  • An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufficient to stabilize said oil base against oxidation deterioration of 3-cyclopentylmercapto-2-methylpropyl phosphite.
  • An improved lubricant comprising a petroleum hydrocarbon base having incorporated therein in an amount suificient to stabilize said base against oxidation deterioration of an alkylmercaptoalkyl ester of phosphorous acid in which at least two hydrogen atoms of the acid are replaced by alkylmercaptoalkyl radicals.
  • An improved lubricant comprising a petroleum hydrocarbon base having incorporated therein in an amount sufiicient tostabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula RSR' in which R and R are saturated aliphatic hydrocarbon radicals, R and R containing from 1 to 15 carbon atoms.
  • An improved lubricant comprising a mineral oil base having incorporated therein in an amount sufficient to stabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula -RSR'- in which R and R are saturated aliphatic hydrocarbon radicals, R and R containing from 1 to 15 carbon atoms.
  • An improved lubricant comprising a petroleum hydrocarbon base having incorporated therein in an amount sufficient to stabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula RX-R'- in which R and R each are saturated aliphatic hydrocarbon radicals, R and R contain from 1 to 15 carbon atoms, X is an element selected from the group consisting of sulfur and selenium.
  • An improved lubricant comprising a liquid hydrocarbon lubricant base having incorporated therein in an amount suificient to stabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula RXR'- in which R and R each are saturated nonaromatic hydrocarbon radicals containing from 1 to 15 carbon atoms, X is an element selected from the group consisting of sulfur and selenium.
  • An improved lubricant comprising a mineral lubricating oil base, from about 0.01% to about 5%, by weight, of tris(3-amylmercapto propyl) phosphite, and from about 0.01 to about 2% of an oil-soluble calcium petroleum sulfonate.
  • An improved lubricant comprising a liquid hydrocarbon lubricant base, having incorporated therein, in an amount suflicient to stabilize said base against oxidation deterioration, an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms of the hydroxyl groups of said acid have the formula -RXR' in which R and R each are saturated non-aromatic hydrocarbon radicals containing from 1 to 15 carbon atoms, X is an element selected from the group consisting of sulfur and selenium, and from about 0.01% to about 2% of an oil-soluble detergent.

Description

Patented Aug. 3, 1954 I UNITED STATES PATENT OFFICE LUBRICANT COMPOSITION CONTAINING ALKYL-MERCAPTOALKYL PHOSPHITES Denham Harman, IOrinda, Califl, assignor to Shell Development Company, Emeryville, Calif., a corporation of Delaware No Drawing. Application November 29, 1951, Serial No. 259,015
17 Claims. (Cl. 252-334) This invention relates to lubricants having imformed by the removal of hydrogen atoms from proved stability and lubricating properties. saturated aliphatic hydrocarbons; X is a non- More particularly, this invention pertains to comoygen .chalkogen element, preferably sulfur and pounded lubricants having incorporated therein 1 is an integer of from 1 to 4.
an additive agent possessing outstanding Wide 5 Additive agents of this invention can be pretemperature anti-oxidant and extreme pressure pared by any suitable means such as the methods properties. employed in the copending application, Serial Various lubricants whether of natural and/or No. 381,561 filed July 13, 1948 and which has synthetic origin such as petroleum hydrocarbons, matured into U. S. Patent No. 2,587,616 of which fixed fats and oils and fractions thereof as Well this application is a continuation-in-part, are
as synthetic lubricants derived from olefinic polyparticularly preferred. mers, organic esters and the like, are generally Illustrative examples of additive agents of this affected by oxygen, air or under various oxidizinvention include:
ing conditions resulting in the formation of undesirable products and deleterious reactions which markedly decrease the useful life of such products or render them useless within a relatively short period of time for their intended purpose such as lubrication of engine parts. Additionally this phenomenon alters both the chemical and physical properties of both the additives and bas lubricant and in the case of the additives possessing extreme pressure properties, such properties are altered rapidly or dissipate, resulting at the best only in a temporary solution to extreme pressure lubrication.
One object of this invention is to impart extreme pressure properties to base lubricants and inhibit their oxidation over a wide temperature range. Another object of this invention is to prevent oxidation of base lubricants. Still another object of this invention is to produce an improved lubricant of outstanding stability and Bis 3 cyclohexylmercaptopropyl) phosphite extreme pressure properties by incorporating in Tris 3-c cloheximercaptopropyl) phosphite said base lviloriciant at, pargicular type of additive 3o 3 cyclopgmylmeicapto 2 methy1propy1 phosphite free from o jec iona 1e 0 ors. Other objects of th 1 r 1) this invention will be apparent from the follow- B158 cyclopentylmercapto 2 me y p opy B-amylmercaptopropyl phosphite Bis(3-amylmercaptopropyl) phosphite Tris(3-amylmercaptopropyl) phosphite 5-10entadecylmercaptopentyl phosphite Bis 5-pentadecylmercaptopentyl) phosphite Tris 5 -pentadecylmercaptopentyl) phosphite 3-amylmercapto-2methylp-ropyl phosphite Bis(3-amylmercapto-2-methylpropyl) phosphite Tris(3-amylmercapto-2-methylpropy1) phosphite 3-octylmercapto2-propylbutyl phosphite Bis(3-octylmercapto-2-propylbutyl) phosphite Tris(3-octylmercapto-2-propylbutyl) phosphite 3 (1,1,3 trimethylbutylmercapto) 2 methylpropyl phosphite BisES (1,1,3 trimethylbutylmercapto) 2- methylpropyl] phosphite Tris[3 (1,1,3 trimethylbutylmercapto) 2- methylpropyl] phosphite 3-cyclohexylmercaptopropyl phosphite ing description of this invention phosphite l l l r 2 h 1 r0 1 It has now been discovered that stable, excelgifg fig Openty me capto met y p py lent extreme pressure lubricants can be prepared by incorporating into a base lubricant minor amounts of a particular type of organo phosphites characterized by the presence of nonoxygen chalkogen atoms solely in the form of 3-amylselenylpropyl phosphite Bis 3-amylselenylpropyl) phosphite Tris(3-amylselenylpropyl) phosphite Trisl3 isobutylmercapto 2,3 dimethylbutyll phosphite non'oxy ether groups m replacmg hydrogen Octyl bis(3-amylmercaptopropyl) phosphite atoms of the hydroxy groups of phosphorous Benzyl bis (S-amylmercaptopropyl) phosphite acids. The preferred class of compounds comprises the alkyl-mercaptoalkyl phosphites, which Dthexyl 3octylmercapto'z'propylbutyl phosphite are aliphatic phosphites in which the aliphatic DIOYPIOheXYI 3 cyclohexylmercaptopropyl phos' radicals replacing the hydrogen atoms of the phlte hydroxyl groups of phosphorous acid, are of the -ethylhexyl 3-amyselenylpropyl phosphite general formula in which R and 3 amylmercaptopropyl dithio dicyclohexyl phosare polar or non-polar substituted non-aromatic Dhite hydrocarbyl radicals and preferably represent Chlorobenzyl bis(3-amylmercaptopropyl) phosmono and divalent 01-015 hydrocarbon radicals phite 3 Chlorophenyl bis(3-amylmercaptopropyl) phosphite Diallyl -pentadecylmercaptopentyl phosphite Dioleyl 3-octylmercapto-2-propyl phosphite Mono 3 octyl merctapto-2-propyl dithio octyl phosphite Tris(3-amyldimercaptopropyl) phosphite Poly phosphites can be used and include such compounds as:
C1CH2CH2OP( OH) OCH2CH2S- CHzCHaOP (OI-I) CHcCI-IzCl CH2=CHCH2OP OH) OCHaCI-Ic SCH2CH2OP (OH) CI-IzCI-I CHz Metal and nitrogen base salts of the acidic phosphorous esters of this invention can also be used as oil improving agents such as the Na, K, Li, Ca, Ba, Al, Zn and Pb as well as the amine salts of any of the above esters or mixtures thereof. Included among the preferred salts are:
Na, Ca and Pb salts of bis(3-arnylmercaptopropyl) phosphite Na, Ca, Zn and Al salts of cyclohexyl mercaptopropyl phosphite Di-Z-ethylhexyla-mine salt of bis(3-amy1mercaptopropyl) phosphite icyclohexylamine salt of cyclohexylmercaptopropyl phosphite Morpholine salt of 3-octylmercaptopropyl phosphite The non-oxygen chalkogen ether containing phosphites of this invention can be used to improve base lubricants, in concentrations varying from 0.001% to 20% and preferably from 0.1% to 5% by weight.
To illustrate the pronounced superiority of additives of this invention as anti-oxidants, the following lubricating compositions were prepared and evaluated by the Dornte Oxidation Stability Test as described in the National Petroleum News, September 1'7, 1941, pages R294-296, and in the High-Temperature Oxidation Apparatus of H. Diamond et al., which is fully described in the general papers presented before the Division of Petroleum Chemistry at the meeting of the American Chemical Society (September 18- 23, 1949, Atlantic City, New Jersey) on pages 31-45 of the reprints. Results of such tests are presented below.
[Baez Refined Mineral Lubricating Oil] Dornte Oxidation High Temperature Test (150 C; 150 Test, 260 0., 250 cc. (1112) cc. (mm) Cu crankcase Cu crankcase Cat. Get. Get. None 5 5 6.5 1.6% tri-octyl phosphite. 13 ll) 32 28 1.84% tris(3-amyl-mercaptopropyl) phcsphita 50 120 36 40 Co, etc. Organic bases include various nitrogen bases as primary, secondary, tertiary amines and quaternary ammonium compounds, e. g., benzyl trirnethyl ammonium hydroxide.
Examples of detergent-forming acids are the fatty acids of say, 10 to 30 carbon atoms, tall-oil acids, rosin acids, wool-fat acids, paraffin-wax acids (produced by oxidation of paraifin Wax), chlorinated fatty acids, aromatic hydroxy fatty acids, paraffin-wax benzoic acids, various alkyl salicyclic acids, phthalic acid monoesters, aromatic keto acids, aromatic ether acids, diphenols such as di-(alkylphenol) sulfides and disulfides,
, methylene bis-alkyl phenols; sulfonic acids such as may be produced by treatment of alkyl aryl hydrocarbons or high-boiling petroleum oils with sulfuric acid; sulfuric acid monoesters; phosphoric, arsonic and antimony acid monoand diesters, including the corresponding thiophosphoric and arsonic acids and the like.
Additional detergents are the alkaline earth phosphate di-esters, including the thiophosphate (ii-esters; the alkaline earth diphenolates, specifically, the calcium and barium salts of diphenol monoand poly-sulfides.
Non-metallic detergents include compounds such as the phosphatides (lecithin and cephalin) certain fatty oils such as rapeseed oils, Voltolized fatty or mineral oils and the like.
An excellent detergent for the present purpose is the calcium salt of oil-solule petroleum sulfonic acids. This may be present advantageously in the amount of about 0.025% to 0.2% sulfate ash. Also, alkaline metal salts of alkyl phenolaldehyde condensation products are excellent detergents.
Corrosion inhibitors or anti-rusting compounds may also be present, such as dicarboxylic acids of 16 or more carbon atoms; alkali metal and alkaline earth salts of sulfonic acids and fatty acids, organic compounds containing an acidic radical in close proximity to a nitrile, nitro, or nitroso group (e. g., alpha-cyanostearic acid), glycidyl phenyl ether, wax disulfide, etc.
Additional ingredients may comprise oil-soluble urea or thiourea derivatives, e. g., urethanes, allophanates, carbazides, carbazones, etc., polyisobutylene polymers, unsaturated polymerized esters of fatty acids and monohydric alcohols and other high-molecular-weight oil-soluble compounds.
Depending upon the additional additive used and conditions under which it is used, the amount of additive used may vary from 0.01 to 2% or higher. However, substantial; improvement is obtained by using amounts ranging from 0.1 to 0.5% in combination with the primary additive of this invention.
I claim as my invention:
1. An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of tri(3-amylmercaptopropyl) phosphite.
2. An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of bis(3-amylmercaptopropyl) phosphite.
3. An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of tris(3-cyclohexylmercaptopropyl) phosphite.
4. An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of 5-pentadecyl1nercaptopentyl phosphite.
5. An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of 3-cyclophenylmercapto-2-methylpropyl phosphite.
6. An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufiicient to stabilize said oil base against oxidation deterioration of tris(3-amylmercapto propyl) phosphite. v
7. An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sunicient to stabilize said oil base against oxidation deterioration of bis(3-amylmercapto propyl) phosphite.
8. An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufficient to stabilize said oil base against oxidation deterioration of tris(3-cyclohexylmercaptopropyl) phosphite.
9. An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufiicient to stabilize said oil base against oxidation deterioration of 5-pentadecyl mercaptopentyl phosphite.
10. An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufficient to stabilize said oil base against oxidation deterioration of 3-cyclopentylmercapto-2-methylpropyl phosphite.
11. An improved lubricant comprising a petroleum hydrocarbon base having incorporated therein in an amount suificient to stabilize said base against oxidation deterioration of an alkylmercaptoalkyl ester of phosphorous acid in which at least two hydrogen atoms of the acid are replaced by alkylmercaptoalkyl radicals.
12. An improved lubricant comprising a petroleum hydrocarbon base having incorporated therein in an amount sufiicient tostabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula RSR' in which R and R are saturated aliphatic hydrocarbon radicals, R and R containing from 1 to 15 carbon atoms.
13. An improved lubricant comprising a mineral oil base having incorporated therein in an amount sufficient to stabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula -RSR'- in which R and R are saturated aliphatic hydrocarbon radicals, R and R containing from 1 to 15 carbon atoms.
14. An improved lubricant comprising a petroleum hydrocarbon base having incorporated therein in an amount sufficient to stabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula RX-R'- in which R and R each are saturated aliphatic hydrocarbon radicals, R and R contain from 1 to 15 carbon atoms, X is an element selected from the group consisting of sulfur and selenium.
15. An improved lubricant comprising a liquid hydrocarbon lubricant base having incorporated therein in an amount suificient to stabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula RXR'- in which R and R each are saturated nonaromatic hydrocarbon radicals containing from 1 to 15 carbon atoms, X is an element selected from the group consisting of sulfur and selenium.
16. An improved lubricant comprising a mineral lubricating oil base, from about 0.01% to about 5%, by weight, of tris(3-amylmercapto propyl) phosphite, and from about 0.01 to about 2% of an oil-soluble calcium petroleum sulfonate.
17. An improved lubricant comprising a liquid hydrocarbon lubricant base, having incorporated therein, in an amount suflicient to stabilize said base against oxidation deterioration, an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms of the hydroxyl groups of said acid have the formula -RXR' in which R and R each are saturated non-aromatic hydrocarbon radicals containing from 1 to 15 carbon atoms, X is an element selected from the group consisting of sulfur and selenium, and from about 0.01% to about 2% of an oil-soluble detergent.
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,205,021 Schuette et al. June 18, 1940 2,241,244 Conary et a1. May 6, 1941 2,371,631 Lincoln et al Mar. 20, 1945 2,372,244 Adams et a1 Mar. 27, 1945 2,373,879 Dietrich Apr. 17, 1945 2,432,095 Frey -1 Dec. 9, 1947 2,587,616 Harman Mar. 4, 1952 2,614,988 Hook et a1. -a Oct. 21, 1952

Claims (1)

17. AN IMPROVED LUBRICANT COMPRISING A LIQUID HYDROCARBON LUBRICANT BASE, HAVING INCORPORATED THEREIN, IN AN AMOUNT SUFFICIENT TO STABLIZE SAID BASE AGAINST OXIDATION DETERIORATION, AN ORGANIC ESTR OF PHOSPHOROUS ACID IN WHICH THE ORGANIC RADICALS WHICH REPLACE HYDROGEN ATOMS OF THE HYDROXYL GROUPS OF SAID ACID HAVE THE FORMULA -R-X-R'' IN WHICH R AND R'' EACH ARE SATURATED NON-AROMATIC HYDROCARBON RADICALS CONTAINING FROM 1 TO 15 CARBON ATOMS, X IS AN ELEMENT SELECTED FROM THE GROUP CONSISTING OF SULFUR AND SELENIUM, AND FROM ABOUT 0.01% TO ABOUT 2% OF AN OIL-SOLUBLE DETERGENT.
US259015A 1951-11-29 1951-11-29 Lubricant composition containing alkyl-mercaptoalkyl phosphites Expired - Lifetime US2685567A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US259015A US2685567A (en) 1951-11-29 1951-11-29 Lubricant composition containing alkyl-mercaptoalkyl phosphites

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US259015A US2685567A (en) 1951-11-29 1951-11-29 Lubricant composition containing alkyl-mercaptoalkyl phosphites

Publications (1)

Publication Number Publication Date
US2685567A true US2685567A (en) 1954-08-03

Family

ID=22983137

Family Applications (1)

Application Number Title Priority Date Filing Date
US259015A Expired - Lifetime US2685567A (en) 1951-11-29 1951-11-29 Lubricant composition containing alkyl-mercaptoalkyl phosphites

Country Status (1)

Country Link
US (1) US2685567A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2886526A (en) * 1954-10-27 1959-05-12 Texas Co Ep additive for mixed lithium-calcium base greases

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2205021A (en) * 1934-11-02 1940-06-18 Ig Farbenindustrie Ag Production of condensation products
US2241244A (en) * 1939-03-25 1941-05-06 Texas Co Organic phosphite compound and method of manufacturing same
US2371631A (en) * 1941-01-04 1945-03-20 Continental Oil Co Lubricant
US2372244A (en) * 1941-09-24 1945-03-27 Standard Oil Co Esters of acids of phosphorus
US2373879A (en) * 1942-09-11 1945-04-17 Du Pont Sulphurized hydrocarbon derivatives
US2432095A (en) * 1941-12-29 1947-12-09 Delton R Frey Lubricating composition
US2587616A (en) * 1948-07-13 1952-03-04 Shell Dev Alkylmercaptoalkyl phosphites
US2614988A (en) * 1948-03-26 1952-10-21 American Cyanamid Co Hydrocarbon oils containing salkoxymethyl - o,o' - dialkyldithiophosphates

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2205021A (en) * 1934-11-02 1940-06-18 Ig Farbenindustrie Ag Production of condensation products
US2241244A (en) * 1939-03-25 1941-05-06 Texas Co Organic phosphite compound and method of manufacturing same
US2371631A (en) * 1941-01-04 1945-03-20 Continental Oil Co Lubricant
US2372244A (en) * 1941-09-24 1945-03-27 Standard Oil Co Esters of acids of phosphorus
US2432095A (en) * 1941-12-29 1947-12-09 Delton R Frey Lubricating composition
US2373879A (en) * 1942-09-11 1945-04-17 Du Pont Sulphurized hydrocarbon derivatives
US2614988A (en) * 1948-03-26 1952-10-21 American Cyanamid Co Hydrocarbon oils containing salkoxymethyl - o,o' - dialkyldithiophosphates
US2587616A (en) * 1948-07-13 1952-03-04 Shell Dev Alkylmercaptoalkyl phosphites

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2886526A (en) * 1954-10-27 1959-05-12 Texas Co Ep additive for mixed lithium-calcium base greases

Similar Documents

Publication Publication Date Title
US2798045A (en) Lubricating compositions
US2777874A (en) Metal complexes and methods of making same
US2736737A (en) Phosphate partial ester-aldehyde condensation product and lubricant containing the same
US2552570A (en) Oxidation resisting hydrocarbon products
US2270577A (en) Compounded lubricating oil
US2526506A (en) Hydrocarbon lubricant containing sulfurized aliphatic borates as stabilizers
US2440530A (en) Stabilized organic compositions
US2451346A (en) Compounded lubricating oil
US2628941A (en) Extreme pressure lubricant
US2690999A (en) Silver protective agents for sulfurcontaining lubricants
US2688001A (en) Low-temperature lubricating composition
US2743235A (en) Mineral oil composition
US2685567A (en) Lubricant composition containing alkyl-mercaptoalkyl phosphites
US3254027A (en) Lubricating oil compositions
US2409726A (en) Lubricant composition
US2689258A (en) Reaction of terpenes with thiophosphorous acid esters and products thereof
US2645613A (en) Lubricating composition
US2483505A (en) Compounded lubricating oil
US3029268A (en) Thioether containing esters of dithiophosphoric acid, and salts thereof
US2599341A (en) New phosphorus containing compounds
US2766207A (en) Hydrocarbon oil products
US2529303A (en) Stabilized hydrocarbon products
US3309428A (en) Oil-soluble bis(methylphosphonodisulfides
US2545158A (en) Oxidation resisting hydrocarbon products
US2523100A (en) Mineral oil composition and additive therefor