US3741896A - Basic alkylene amine and sulfur bridged alkylphenoxides for use in lubricating oils - Google Patents

Basic alkylene amine and sulfur bridged alkylphenoxides for use in lubricating oils Download PDF

Info

Publication number
US3741896A
US3741896A US00186494A US3741896DA US3741896A US 3741896 A US3741896 A US 3741896A US 00186494 A US00186494 A US 00186494A US 3741896D A US3741896D A US 3741896DA US 3741896 A US3741896 A US 3741896A
Authority
US
United States
Prior art keywords
percent
alkylphenol
temperature
sulfurized
weight percent
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
US00186494A
Other languages
English (en)
Inventor
A Abbott
T Liston
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.)
Chevron USA Inc
Original Assignee
Chevron Research and Technology 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 Chevron Research and Technology Co filed Critical Chevron Research and Technology Co
Application granted granted Critical
Publication of US3741896A publication Critical patent/US3741896A/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/16—Reaction products obtained by Mannich reactions
    • 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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
    • 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
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings 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
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
    • 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
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy 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
    • C10M2207/28—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
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/102—Polyesters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • 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
    • C10M2209/12—Polysaccharides, e.g. cellulose, biopolymers
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044—Acids; Salts or esters 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary 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
    • C10M2215/04—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
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives 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
    • 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
    • C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic 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
    • 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
    • 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
    • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty 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
    • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty 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
    • C10M2215/10—Amides of carbonic or haloformic 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
    • 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
    • C10M2215/12—Partial amides of polycarboxylic 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
    • 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
    • C10M2215/18—Containing nitrogen-to-nitrogen bonds, e.g. hydrazine
    • 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
    • C10M2215/20—Containing nitrogen-to-oxygen bonds
    • C10M2215/202—Containing nitrogen-to-oxygen bonds containing nitro 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • C10M2215/224—Imidazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—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
    • 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
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—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
    • C10M2215/30—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—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
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
    • 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
    • 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
    • C10M2219/064—Thiourea type 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
    • 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • 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
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/02—Esters of silicic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • 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
    • 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
    • C10N2010/08—Groups 4 or 14
    • 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
    • C10N2010/12—Groups 6 or 16
    • 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
    • C10N2010/14—Group 7
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • Novel dispersant detergents are provided by combining, at an elevated temperature, a sulfurized alkylphenol and a Mannich baseprepared from formaldehyde, alkylphenol, and a lower alkyl monoaminein the presence of an alkaline earth metal base and a liquid hydroxylic compound, so as to prepare the alkaline earth metal salt of a chemically combined sulfurized alkylphenol and Mannich base.
  • compositions which are detergent dispersants also provide antioxidant activity and alkalinity reserve.
  • Lubricating oils used under the severe conditions of diesel engines are highly compounded so as to provide neutralization of acids derived from the sulfur in the fuel and oxidation of hydrocarbons, both of the fuel and oil; dispersancy so as to maintain sludge-forming precursors dispersed in the oil; improved wear protection and oiliness properties; as well as enhancing other attributes of the oil.
  • those oils which find use in railway diesel engines have the additional factor of not being corrosive or reactive to silver. Silver bearings are used in a preponderant number of diesel engines today.
  • New deteregnt dispersant phenates having alkalinity reserve and antioxidant activity are prepared by the simultaneous neutralization of a sulfurized alkylphenol and a Mannich base prepared from a lower alkyl amine, an alkylphenol and formaldehyde.
  • the neutralization is carried out at elevated temperatures with an alkaline earth metal base in the presence of a hydroxylic solvent under conditions to minimize the loss of amine nitrogen.
  • compositions of this invention are the reaction products of an alkaline earth metal base, oxide or hydroXide, a Mannich base-prepared from formaldehyde, alkylphenol, and a primary lower alkyl amine-and a sulfurized alkylphenol.
  • the reaction is carried out at elevated temperatures so that molecular bonds are formed between the Mannich base and the sulfurized alkylphenol in addition to those bridging bonds created by the divalent alkaline earth metal.
  • the product as formed (independent of any diluent) will have an alkalinity value (ASTM Test-D2896) in mg. KO'H/g. in the range of to 450, more usually about to 400.
  • the product will provide in elemental analysis from about 4 to 12, more usually from about 5 to 10, weight percent calcium, at least about 0.1 to 5, more usually from about 0.5 to 4, weight percent nitrogen, and from about 0.8 to 10, more usually from about 2 to 8, weight percent sulfur.
  • a 100 neutral oil (100 being the viscosity at 100 F. in SUS) at an alkaline earth metal concentration of 0.88 formal (3.5 weight percent for Ca)
  • the viscosity at 210 F. will normally be in the range of about 200 to 3,000 SUS, more usually in the range of 500 to 1,500 SUS.
  • compositions of the subject invention are complex in nature. It is believed that a substantial proportion of the composition corresponds to one of the following formulae:
  • y 1 to 10, primarily in the range 1 to 5, preferably 2 to 4;
  • n 1 to 5, more usually 1 to 3;
  • R is a saturated aliphatic hydrocarbon, either branchedor straight-chain, having from 8 to 36 carbon atoms, more usually from to 24 carbon atoms, the average number of carbon atoms generally being in the range of about 10 to 20;
  • R is lower alkyl, usually of from 1 to 3 carbon atoms
  • the ratio over the entire composition of the equivalents of alkylphenol from the Mannich base to equivalents of alkylphenol from the sulfurized alkylphenol will normally be 0.25:1, more usually 0.3-3z1, and preferably 03-211.
  • the remaining valences of the oxygen atoms are satisfied by an alkaline earth metal.
  • These metals are calcium and barium, preferably calcium. Both valences of the metal may be satisfied by the phenoxide or one valence by the phenoxide and the other valence by an alkoxide or hydroxide, the group varying with the hydroxylic solvent employed and the proportion of alkaline earth metal used in the reaction.
  • A (few of the phenoxide groups, not exceeding 10 mole percent, may be bonded to hydrogen, depending on the amount of excess of alkaline earth metal present.
  • compositions of this invention are prepared by combining in a suitable reactor the Mannich base and sulfurized alkylphenol in an equivalent ratio (based on phenol) in the range of 0.2-5 :1, more usually 0.3-311.
  • an alkaline earth metal oxide or hydroxide preferably hydroxide
  • a hydroxylic solvent usually ethylene glycol.
  • the amount of alkaline earth metal base will depend on on the method of preparation of the sulfurized alkylphenol. To the degree that an alkaline earth metal base was employed during the preparation of the sulfurized alkylphenol, .the added amount of alkaline earth metal base will provide a total of at least one equivalent of alkaline earth metal present per equivalent of alkylphenol present, usually not exceeding 1.75 equivalents, and more usually not exceeding 1.5 equivalents of alkaline earth metal per equivalent of phenol present.
  • the amount of the hydroxylic solvent will vary with the particular solvent employed. Ethylene glycol, propylene glycol, and methanol are examples of suitable solvents. Since ethylene glycol is the preferred solvent, only its use will be discussed in detail. The amount of ethylene glycol employed will normally be from about 5 to 35 weight percent, preferably from about 7 to 20 weight percent, of the total reaction mixture.
  • inert hydrocarbon diluent may also be present.
  • inert diluents may serve to aid in the handling of the reactants, lowering the viscosity of the reaction mixture, and enhancing the ease of isolation of the product.
  • mineral oils of lubricating viscosity may be employed and the product isolated as a solution in the mineral oil.
  • the inert diluent will be present in the reaction mixture, if at all, in amounts of from 3 to 65 weight percent more usually 5 to 50 weight percent of the total reaction mixture.
  • foaming suppressant a small amount of an antifoaming agent or foaming suppressant may be employed.
  • the foam suppressant will normally be present in the reaction mixture in amounts of 1 10- to 1x10 weight percent.
  • Foam suppressants are conventional and need not be exemplified here.
  • the reaction is conveniently carried out by combining the sulfurized alkylphenol, the Mannich base, the alkaline earth metal oxide or hydroxide, and ethylene glycol.
  • an inert diluent may also be present.
  • the mixture is heated to at least C., but below the temperature at which the reaction is to be carried out, normally below 140 C.
  • the temperature is raised so as to distill water overhead, removing the water of reaction.
  • the temperature is then raised, not to exceed 200 C.
  • the pressure is reduced to permit the distillation of ethylene glycol.
  • the temperature during removal of water will range from to 160 C.
  • the temperature during removal of ethylene glycol will range from to 200 C., preferably from to 180 C.
  • the pressure will vary, depending on the temperature and rate of distillation desired.
  • the reduced pressure may vary from about 0.01 to 0.8 atmosphere.
  • the time required for the removal of water will usually be from about 30 minutes to 3 hours.
  • the time for the removal of ethylene glycol will normally be about 30 minutes to 9 hours.
  • the time for the reaction that is, from the initial removal of water to substantially complete removal of ethylene glycol, will vary fromabout 1 hour to 6 hours.
  • the time, while not a critical factor, should not be unduly protracted, and will depend on the capacity of the equipment, the amount of reactants, the degree of foaming and the ability to control the temperature and rate of removal of distillates.
  • the reaction mixture may be cooled.
  • the temperature should preferably be maintained above about 150 C. prior to sufficient dilution with a convenient solvent.
  • the mixture can become extremely viscous, and solution into a solvent is difiicult below a temperature of about 150 C.
  • Any convenient solvent may be used, but in view of the intended use, normally a hydrocarbonaceous lubricating oil will be used as the diluent. Depending on the end use, various hydrocarbonaceous lubricating oils may be employed.
  • the product is ready to be employed, after filtration, as a concentrate for formulating finished lubricating oils.
  • the various reactants will now be considered.
  • the first and simplest reactant is the alkaline earth metal oxide or hydroxide. As already indicated, these are calcium and barium, preferably calcium. With calcium, normally calcium hydroxide will be employed.
  • Sulfurized alkylphenols are well known materials for use in lubricating oils.
  • the method of preparation of the sulfurized alkylphenols is not critical to this invention.
  • the sulfurized alkylphenol should have at least about 4 weight percent sulfur and not more than about 20 weight percent sulfur, more usually from about 8 to 18 weight percent sulfur.
  • the sulfurized alkylphenols will, for the most part,
  • R is alkyl of from 8 to 36 carbon atoms, more usually of from to 24 carbon atoms with the average number of carbon atoms being in the range of about 10 to 20
  • y is an integer of from 1 to 9, more usually of from 1 to 5, averaging over the entire composition in the range of about 2 to 4
  • n is an integer of from 1 to 5, more usually of from 1 to 3.
  • the aliphatic hydrocarbon groups designated R may be in the ortho, meta, or para positions, but will predominate in the meta or para positions. Since branchedchain alkyl groups tend to minimize the amounts of ortho-substituted phenols, the branched-chain alkyl groups are preferred. However, it should be realized that to some extent the alkyl groups are in the ortho position, and ortho-substituted phenols act as chain terminators in the copolymerization of sulfur and alkylphenol.
  • the sulfurized alkylphenol can be prepared by combining alkylphenol, sulfur, calcium oxide, or calcium hydroxide and glycol at an elevated temperature, driving off the water and hydrogen sulfide, followed by isolation of the sulfurized alkylphenol. See, for example, U.S. Patent No. 2,989,466. Sulfur monochloride may also be used to prepare sulfurized alkylphenols, frequently employing a Friedel-Crafts catalyst to aid the reaction. Various methods of preparing sulfurized alkylphenols may be found in US. Patents Nos. 2,362,289, 2,451,345, 2,744,- 083, and 3,367,867.
  • the Mannich bases which are employed are prepared by combining at elevated temperatures, an alkylphenol, formaldehyde, and a primary lower alkylamine, preferably of from 1 to 3 carbon atoms, and particularly preferred, methyl amine.
  • a method for preparing the Mannich bases may be found in copending application Ser. No. 22,452, filed on Mar. 25, 1970. US. Patent No. 3,454,497 describes an additional method for preparing Mannich bases employing primary amines.
  • R3 x R3 wherein R is lower alkyl, usually of from 1 to 3 carbon atoms, and preferably of 1 carbon atom, methyl, R is saturated aliphatic hydrocarbon of from 8 to 36 carbon atoms, more usually of from 10 to 24 carbon atoms, and normally having an average number of carbon atoms in the range of from 10 to 20, x will range from 1 to 19, usually averaging in the range of 4 to 9. There may be small amounts, less than 10 Weight percent, of Mannich bases having x greater than 19. The average over the entire composition will normally be in the range of 3 to 9, with more than 50 weight percent of the composition having x equal to 3, or higher.
  • the Mannich base will normally be prepared from alkylphenols having less than 25 mole percent, preferably less than 20 mole percent ortho substitution.
  • the Mannich base in the invention will have less than 20, usually less than 10, number percent of attachment of the Mannich amine at the position para to the hydroxyl group of the phenol.
  • the Mannich base (undiluted) will have at least 2 weight percent nitrogen and normally not more than about 5 weight percent nitrogen, the amount of nitrogen normally being in the range of about 2.2 to 4.0.
  • the average molecular weight, as determined by osmometry, will be at least 600, more usually at least 700', and normally not exceed about 5,000.
  • EXAMPLE 1 Into a reaction vessel are introduced 8,825 parts of sulfurized alkylphenol (prepared as described in Example A), 10,350 parts of a Mannich base (prepared as described in Example B) as a 60 weight percent solution in a mid-continent neutral oil, 2 parts of DC-200 foam inhibitor, and 1,640 parts of calcium hydroxide. The mixture is heated at 250275 F. and 5,150 parts of ethylene glycol added. The pressure is then reduced to 20" mercury and the mixture heated to 300 F. over a period of 50-70 minutes while water is removed overhead. When substantially all of the water is removed, the temperature is then raised to 375 F. over a period of two to three hours.
  • the pressure is concomitantly reduced so that the maximum vacuum is reached at about the time the temperature reaches 340 F.
  • the final pressure on the kettle is not greater than 50 millimeters of mercury.
  • the mixture is then cooled rapidly to 300 F. and nitrogen introduced into the system to atmospheric pressure.
  • To the mixture is then charged 4,500 parts of 100 neutral oil and the solution mixed for 30 minutes while maintaining the temperature at about 250 F.
  • the product may then be isolated.
  • the above product will have about 4.2 weight percent calcium and a viscosity of about 4,000 SUS at 210 F.
  • EXAMPLE A Into a reaction vessel are introduced 18,100 parts of polypropylphenol (prepared from polypropylene of from about 12 to 15 carbon atoms), 750 parts of calcium oxide and 4,620 parts of sulfur, the temperature of the mixture being maintained at 220 F. The temperature is then raised to 265-275 F. and 580 parts of ethylene glycol charged. Hydrogen sulfide begins to be evolved and a low rate nitrogen purge is then begun over the top of the reactor. The temperature is slowly raised to 335340 F. and thetemperature maintained for a period of 6 hours. At the end of this time, the mixture is cooled to about 225-250 F. and the product may be isolated.
  • polypropylphenol prepared from polypropylene of from about 12 to 15 carbon atoms
  • EXAMPLE B Into a reaction vessel is introduced 60.4 parts of polypropylphenol (prepared from polypropylene of from about 12 to 15 carbon atoms) and the system degassed and purged with nitrogen. After the purging is completed, 17.9 parts of isobutyl alcohol and 14.5 parts of paraformaldehyde are added while the mixture is agitated. To the mixture is then added 7.2 parts of liquid methyl amine, the addition requiring 3 hours. The temperature, during the addition, is maintained at -150 F.
  • polypropylphenol prepared from polypropylene of from about 12 to 15 carbon atoms
  • the sulfurized alkylphenol was prepared as described in Example A, filtered, and had the following specifications (neat): The alkylphenol was polypropylphenol havminutes, and then the reaction mixture was allowed to cool, nitrogen being introduced to break the vacuum. The product was then diluted with 300 grams of a mid-continent 100 neutral oil. The oil solution was then filtered through Celite, the filtered product weighing 1,105 grams. Analysis (percent): Ca, 4.43, 4.24; N, 0.82, 0.82; S, 3.56. Alkalinity value, mg. KOH/g, 152.5, 151.4.
  • the sulfurized alkylphenol employed above was prepared as described in Example A and had the following specifications: percent 8', 14.9; alkalinity value mg. KOH/ g., 62.7; percent Ca, 2.16, viscosity at 210 F., SUS, 2,435.
  • Example 3 A number of additional examples were carried out following substantially identically the procedure of Example 3, except for variation in the ratio of sulfurized alkylphenol and Mannich base. Both the sulfurized alkylphenol and Mannich base were obtained from the same batch preparation. The following table indicates the amounts of material employed, and the specifications in the final product. All of the specifications indicated are based on a composition which is 63 weight percent active in a midcontinent 100 neutral oil.
  • alkyl groups of from 12 to 15 carbon atoms; alkalinity 35 EXAMPLE 9 value mg. KOH/g., 63.6; percent Ca, 2.27; percent S, l4.99; viscosity at 210 F., SUS, 2740.
  • the Mannich base was prepared from polypropyl alkylphenol (polypropylene of from 12 to 15 carbon atoms) as described in Example B.
  • the product had the following specification, as a 66.7 weight percent solution in a midcontinent 100 neutral oil: percent N, 2.74; alkalinity value, mg. KOH/g., 109; viscosity at 210 F., SUS, 425.)
  • the mixture was heated rapidly to 265 F. and a 10" Hg vacuum applied, water and hydrogen sulfide being removed overhead.
  • the pressure was decreased and the temperature raised over a period of 4 hours and minutes, the final temperature being 380 F., and the final vacuum about 48 mm. Hg.
  • water and ethylene glycol were taken overhead.
  • the mixture was cooled to 275 F., the vacuum broken with the introduction of nitrogen and when the temperature had fallen to about 260 F., 5,092 grams of a mid-continent 100 neutral oil was added as diluent.
  • the product as an oil solution had an alkalinity value of 147 mg. KOH/g.; percent N, 0.75; percent S, 3.2; and percent Ca, 4.2. After some dilficulty, the product was diluted further with mid-continent 100 neutral oil and filtered using a mixture of Celite 573 and Celite 545. The filtered product weighed 15,457 grams. Percent N, 0.60, percent Ca, 3.35, percent S, 3.12.
  • EXAMPLE 3 Into a reaction vessel were introduced 427 grams (1.28 equivalents) of sulfurized alkylphenol and 454 grams (0.93 equivalent) of the Mannich base described in Example 2 as a 66.7 weight percent active solution, the mixture heated to 95 C. and 253 grams of ethylene glycol and 80 grams (2.16 equivalents) of calcium hydroxide added. The pressure was reduced to 10" vacuum and Water collected overhead as the temperature was raised to 125 C. The temperature was then raised to 150 C. over a 55-minute period, followed by slowly reducing the pressure to mm. Hg, while slowly raising the temperature to 182 C. The temperature was maintained for 15 Into a reaction vessel were introduced 427 grams of sulfurized alkylphenol prepared as follows.
  • Example A A number of sulfurized alkylphenols were prepared by the process described in Example A, where the sulfur to alkylphenol ratio was varied. These compositions were then combined with Mannich base as prepared in Example B, substantially following the procedure of Example 1. The following table indicates the sulfur to alkylphenol ratios, the analysis of the product, the analysis of the Mannich base and the analysis of the final product.
  • EXAMPLE 18 Into a reaction flask fitted with nitrogen bubbler was introduced 100 grams of 2,2'-bis(l-hydroxy-4-polypropylenphenyl)-disulfide (polypropylene of from 12 to 15 carbon atoms) as a 75 wt. percent solution in oil and 150 grams of the Mannich base prepared as described in Example B as a 66.7 wt. percent active solution in a mid-continent 1'00 neutral oil (alkalinity value mg. KOH/g., 108; percent N, 2.74) and the mixture heated to 100 C. While maintaining a nitrogen atmosphere. To the reaction mixture was then added 18 g. of calcium hydroxide, 29 g. of ethylene glycol and one drop of DC 200.
  • 2,2'-bis(l-hydroxy-4-polypropylenphenyl)-disulfide polypropylene of from 12 to 15 carbon atoms
  • Mannich base prepared as described in Example B as a 66.7 wt. percent active solution in a
  • the temperature was then raised to 150 C. and the pressure dropped to 200 mm. Hg and these conditions maintained for 30 minutes.
  • the pressure was then reduced to 50 mm. Hg, the temperature raised to 180 C. and maintained for 15 minutes.
  • the mixture was cooled to 100 C. and filtered through a 50/50 mixture of Celite 512 and Dicalite 573. The filtration was slow. Analysis (percent): N, 120; Ca, 3.52. A.V. mg. KOH/g., 147.
  • compositions of this invention find particular use in lubricating oils where not only detergency and dispersancy are desirable, but also acid neutralization capacity and antioxidant activity.
  • compositions of this invention can be used with various base oils which find use as lubricating oils.
  • Oils of lubricating viscosity have viscosities in the range of about 35 to 50,000 S'US (Saybolt Universal Seconds) at 100 F. Normally, the oils which find use in this invention will have viscosities at 210 F. in the range of about to 150 SUS, more usually from about 60 to 120 SUS.
  • the hydrocarbon lubricating oils may be derived from natural sources and be paraffinic, naphthenic, or asphaltic based on mixtures thereof. Alternatively, synthetic hydrocarbon oils may be used.
  • compositions of this invention may also find use in nonhydrocarbon synthetic oils such as esters, silicates, etc.
  • nonhydrocarbon synthetic oils such as esters, silicates, etc.
  • the various oils may be used together whenever miscible or made so by mutual solvents.
  • compositions of this invention when formulated as concentrates will normally be from about 15 to 70 weight percent, more usually from about 30 to 60 weight percent.
  • the amount of the subject composition When used in formulations, depending on the particular formulation, the amount of the subject composition will generally vary from about 5 to 400 mM./kg. based on metal, more usually from about 8 to 75 mM./kg. based on metal.
  • the alkalinity value is at least 5, more usually of at least 6 mg. KOH/g. and not more than about 15 mg. KOH/g.
  • additives may also be present in the formulation.
  • sulfurized aliphatic hydrod 253 parts of ethylene glycol, parts of calcium hydroxcarbons are well known in the art and tend to have from about 16 to 50 carbon atoms and vary from about 15 to 25 weight percent sulfur. These additives will be present in from 0.05 to 0.75 weight percent.
  • nonash-containing detergents and dispersants are primarily aliphatic polyols of from 2 to 6 hydroxyl group or alkylene polyamines (alkylene of from 2 to 3 carbon atoms) having from 3 to 5 amine nitrogen atoms, either directly bonded to an aliphatic hydrocarbon group of from about 30 to 200 carbon atoms, more usually from 50 to 125 carbon atoms, or indirectly to an acyl group, such as succinyl, phosphoryl, carboxyl, etc., where the acyl group has a hydrocarbon substituent and forms ester or polyester with the alcohols, and an amide or imide, e.g., succinimide, link to the alkylene polyamine.
  • acyl group such as succinyl, phosphoryl, carboxyl, etc.
  • additives may also be present in minor amounts, such as additional ash-containing detergents, e.g. sulfonates, both neutral and overbased, phosphonates, both neutral and over-based, corrosion inhibitors, oiliness agents, pour point depressants, viscosity index improvers, etc.
  • additional ash-containing detergents e.g. sulfonates, both neutral and overbased, phosphonates, both neutral and over-based, corrosion inhibitors, oiliness agents, pour point depressants, viscosity index improvers, etc.
  • the first test to be discussed is referred to as the Oxidation Test to determine antioxidant activity.
  • To 25 grams of the test oil is added 0.26 cc. of a solution having 2268 p.p.m. of copper, 6236 p.p.m. of iron, 567 p.p.m. of manganese, 4535 p.p.m. of lead, and 4535 p.p.m. of chromium, all as their naphthenates, providing a distribution of metals which would be expected to be found in a used crankcase oil from a General Motors D-71 diesel engine.
  • the oil sample to be tested is maintained at 340 F. with stirring in an oxygen atmosphere and the percent increase in viscosity at F. in ten hours determined.
  • compositions were formulated in a 70 VI. SAE 40 oil to simulate a commercial formulation.
  • oil were employed 59 mM./'kg. based on calcium of the test composition, 6 weight percent of a bis(polysiobutenyl succinimide) of tetraethylene pentamine' (mixed polyisobutenyl of about 640 and 1000 number average molecular weight), 22 mM./kg. based on calcium of calcium mahogany sulfonate (1.67 wt. percent Ca) 0.3 wt. percent of sulfurized paraflin having 17.5 wt. percent sulfur, and 0.025 wt. percent of terephthalic acid.
  • the second test to be discussed is the silver thrust washer test.
  • a silver test piece is used made of fine silver, 99.9 percent pure, soldered to a backing of soft steel. Both silver and backing are nominally A1" in thickness, 1.3 inches OD and 1.0 inch ID.
  • the silver surface is grooved by 3 equally spaced slots obtained by 4" end mill charnfered 30 on its lower end. A 0.0l-inch deep and A "-wide slot is cut across the center of each of the three raised silver surfaces.
  • the solution is divided between two 100 ml. calibrated centrifuge tubes and then centrifuged at 2200 r.p.m. for 0.5 hour.
  • the sediment is read and the average of the two readings taken. The results are reported as ml. of sediment per 10 mg. KOH/g. of sample and ml. of sediment per 10 mg. KOH/g. of sample due to amine nitrogen.
  • the silver test piece is annealed after machining and after each use to remove any work hardening in the silver.
  • the annealing is carried out at 650 F. for hour, allowing to slowly cool to room temperature. Following annealing, both sides are surface lapped to obtain a smooth flat surface of approximately 9-12 microinches finish.
  • the steel test specimen is made to duplicate the metallurgy of the wrist pin steel in the EMD locomotive engine.
  • the material is AISI Steel No. 8620H.
  • Heat treatment to a minimum hardness of 58 Rockwell C is achieved by carburizing for 0.040.05 finish case depth, pit cool; reheating to 1,475 F. and oil quenching; followed by tempering at 400 F. for 8 hours. Both sides are finished-lapped to a finish of 3-5 microinches. Nominal dimensions are 1 /2 inches OD, 0.9 inch 1D, and 0.2 inch thick.
  • a motor-driven mechanism is used to obtain oscillatory motion at the test surfaces.
  • a 20 cc. sample of fresh oil is employed in the oil cup, the apparatus assembled and the oscillatory motion begun.
  • the apparatus is run for minutes without heating.
  • At the end of the 10 minutes there is a 35-minute heatup as the temperature is raised to 350 F., followed by minutes of constant temperature operation at 350 F.
  • the load during the test is maintained continuously at 4280 p.s.i. at the bearing surfaces by means of a calibrated spring.
  • the wattage is recorded during the constant temperature operation as an indication. of the work load.
  • the weight loss of silver is re ported. (A sign indicates an increase in weight.)
  • Another test that was carried out was to determine the amount of sediment resulting upon the addition of sulfuric acid. Since diesel fuels contain sulfur and produce sulfuric acid, it is desirable to produce a minimum amount of sediment upon neutralization with sulfuric acid. The alkalinity value is determined of the sample to be tested, and the amount of cone. H 80 required to neutralize the sample is calculated. To a 50-gram sample is added 150 ml. n-heptane and the mixture stirred in a Waring blender. Sulfuric acid is added dropwise over a 5 minute period in anamount sufficient to neutralize the base present and the mixture then homogenized for 10 minutes. At the end of In order to demonstrate the subject compositions activity under severe conditions in a diesel engine, a BMEP test was carried out.
  • the one-cylinder diesel engine employed has a bore of 5%" and a stroke of 6V2".
  • the brake horsepower is 55, and the engine is run at 7460 B.t.u.s per minute and 1880 r.p.m., with the air temperature at 255 F., the outlet water temperature at F., the oil to bearing temperature at 205 F., and a fuel which contains 1.0 weight percent sulfur.
  • the test was run for 120 hours and the following resultsobtained.
  • the above results demonstrate the excellent effectiveness of the subject compositions under a wide variety of conditions.
  • the subject compositions provide low sediment when neutralized in sulfuric acid. In addition, they significantly reduce the wear loss with silver bearings. Also of importance, under extremely severe conditions at high temperatures in a diesel engine, they are able to maintain at low level of deposits. In addition, they provide excellent antioxidant activity, minimizing viscosity increases in lubricating oils and are able to neutralize gross amounts of acids.
  • composition of matter comprising in an admixture a major amount of an oil of lubricating viscosity and from to 400 millimoles per kilogram of oil based on calcium or barium of the reaction product of (l) a Mannich base of the formula:
  • R is a lower alkyl having from 1 to 3 carbon atoms
  • R is a saturated aliphatic hydrocarbyl having from 8 to 36 carbon atoms
  • x is an integer from 1 to 19; with (2) a sulfurized alkylphenol of the formula:
  • R is an alkyl of 8 to 36 carbon atoms, :1 is an integer from 1 to 5, and y is an integer from 1 to 9;
  • composition defined in claim 1 wherein said reaction product when admixed with a neutral oil at a concentration of 0.88 formal of calcium or barium has a viscosity at 210 F. in the range of 200 to 3,000 SUS.
  • composition defined in claim 3 wherein 2.5 to 10 weight percent of a polyisobutenyl succinimide of an alkylene polyamine lubricating oil detergent is also present within said oil.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00186494A 1970-12-11 1971-10-04 Basic alkylene amine and sulfur bridged alkylphenoxides for use in lubricating oils Expired - Lifetime US3741896A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US9730070A 1970-12-11 1970-12-11
US18649471A 1971-10-04 1971-10-04

Publications (1)

Publication Number Publication Date
US3741896A true US3741896A (en) 1973-06-26

Family

ID=26793089

Family Applications (1)

Application Number Title Priority Date Filing Date
US00186494A Expired - Lifetime US3741896A (en) 1970-12-11 1971-10-04 Basic alkylene amine and sulfur bridged alkylphenoxides for use in lubricating oils

Country Status (11)

Country Link
US (1) US3741896A (enrdf_load_stackoverflow)
AU (1) AU445627B2 (enrdf_load_stackoverflow)
BE (1) BE776567A (enrdf_load_stackoverflow)
CA (1) CA987343A (enrdf_load_stackoverflow)
DE (1) DE2161121C2 (enrdf_load_stackoverflow)
DK (1) DK153165C (enrdf_load_stackoverflow)
FR (1) FR2117410A5 (enrdf_load_stackoverflow)
GB (1) GB1352760A (enrdf_load_stackoverflow)
IE (1) IE36704B1 (enrdf_load_stackoverflow)
IT (1) IT959354B (enrdf_load_stackoverflow)
NL (1) NL170305C (enrdf_load_stackoverflow)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4107141A (en) * 1975-10-10 1978-08-15 Vladimir Vasilievich Moiseev Method of preparing phenolamine resins
FR2404670A1 (fr) * 1977-09-30 1979-04-27 Chevron Res Nouvelles bases de mannich, leur procede de preparation et leur application comme additifs pour huiles lubrifiantes
DE2917315A1 (de) * 1978-05-01 1979-11-15 Chevron Res Mannich-basen und deren erdalkalimetallsalze, verfahren zu deren herstellung und deren verwendung als schmieroeladditive
US4175044A (en) * 1977-01-03 1979-11-20 Chevron Research Company Mannich base composition and lubricating oil compositions containing same
US4828742A (en) * 1987-07-24 1989-05-09 Exxon Chemical Patents, Inc. Lactone-modified, mannich base dispersant additives useful in oleaginous compositions
US4913830A (en) * 1987-07-24 1990-04-03 Exxon Chemical Patents Inc. Lactone-modified, mannich base dispersant additives useful in oleaginous compositions
US5166439A (en) * 1989-11-24 1992-11-24 Ethyl Petroleum Additives, Inc. Composition containing a mannich base of a partially sulfurized hindered phenol mixture
US5498809A (en) * 1992-12-17 1996-03-12 Exxon Chemical Patents Inc. Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
US5554310A (en) * 1992-12-17 1996-09-10 Exxon Chemical Patents Inc. Trisubstituted unsaturated polymers
US5811379A (en) * 1996-06-17 1998-09-22 Exxon Chemical Patents Inc. Polymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such polymers and additives and use thereof (PT-1267)
US5814111A (en) * 1995-03-14 1998-09-29 Shell Oil Company Gasoline compositions
US6066603A (en) * 1996-06-17 2000-05-23 Exxon Chemical Patents Inc. Polar monomer containing copolymers derived from olefins useful as lubricant and useful as lubricant and fuel oil additivies process for preparation of such copolymers and additives and use thereof
US6172015B1 (en) 1997-07-21 2001-01-09 Exxon Chemical Patents, Inc Polar monomer containing copolymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such copolymers and additives and use thereof

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1044574B (it) * 1975-07-14 1980-03-31 Liquichimica Robassomero Spa Additivo detergentfe per la sua preparazione
CA1094053A (en) * 1976-04-08 1981-01-20 John Crawford Lubricant additive formed by neutralisation of a sulphurised alkyl phenol and a mannich base
AU651268B2 (en) * 1992-02-18 1994-07-14 Idemitsu Kosan Co. Ltd Mannich reaction product and process for producing the same and use of the product
KR101388866B1 (ko) * 2006-02-27 2014-04-23 바스프 에스이 안정화제로서의 다핵 페놀계 화합물의 용도

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2362289A (en) * 1938-12-16 1944-11-07 Standard Oil Dev Co Lubricating compositions
US2410911A (en) * 1943-12-22 1946-11-12 Standard Oil Dev Co Process of preparing a lubricating oil solution of a condensed organic amino compound
US2451345A (en) * 1944-10-24 1948-10-12 Standard Oil Dev Co Compounded lubricating oil
US2527279A (en) * 1949-11-17 1950-10-24 Gulf Oil Corp Antioxidants for mineral oil lubricants and compositions containing the same
US2763616A (en) * 1952-05-24 1956-09-18 Socony Mobil Oil Co Inc Alkylthiohydroquinones-formaldehyde-amine reaction products and petroleum fractions, containing the same
US2744083A (en) * 1952-07-23 1956-05-01 Exxon Research Engineering Co Metal and sulfur containing compounds and lubricants containing them
US2810697A (en) * 1954-05-27 1957-10-22 Gulf Oil Corp Resinous products and lubricant compositions containing them
US2962442A (en) * 1957-01-03 1960-11-29 Socony Mobil Oil Co Inc Preparation of aldehyde-polyamine-hydroxyaromatic compound condensates and hydrocarbon fractions containing the same
US2989466A (en) * 1959-10-06 1961-06-20 California Research Corp Oxyalkylated-carbonated phenates in lubricating oils
US3368972A (en) * 1965-01-06 1968-02-13 Mobil Oil Corp High molecular weight mannich bases as engine oil additives
US3340190A (en) * 1965-06-01 1967-09-05 Standard Oil Co Railway diesel oil
US3372118A (en) * 1965-12-07 1968-03-05 Lubrizol Corp Process for preparing basic alkyl phenolic compositions
US3413347A (en) * 1966-01-26 1968-11-26 Ethyl Corp Mannich reaction products of high molecular weight alkyl phenols, aldehydes and polyaminopolyalkyleneamines
US3429812A (en) * 1966-09-26 1969-02-25 Texaco Inc Method of preparing lubricating oil concentrate containing calcium salt of alkylphenol - formaldehyde - diaminoalkane condensation product
US3454497A (en) * 1966-11-14 1969-07-08 Shell Oil Co Lubricating compositions
US3474035A (en) * 1967-03-20 1969-10-21 Texaco Inc Lubricating oil containing overbased sulfurized calcium alkylphenolate
US3586629A (en) * 1968-09-16 1971-06-22 Mobil Oil Corp Metal salts as lubricant additives
US3472773A (en) * 1968-10-01 1969-10-14 Texaco Inc Method of preparing calcium salts of bis(2-hydroxyalkylbenzyl) diaminoalkane lube oil composition
BE764074A (fr) * 1970-03-25 1971-09-10 Chevron Res Procede de preparation d'un phenate metallique

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4107141A (en) * 1975-10-10 1978-08-15 Vladimir Vasilievich Moiseev Method of preparing phenolamine resins
US4175044A (en) * 1977-01-03 1979-11-20 Chevron Research Company Mannich base composition and lubricating oil compositions containing same
FR2404670A1 (fr) * 1977-09-30 1979-04-27 Chevron Res Nouvelles bases de mannich, leur procede de preparation et leur application comme additifs pour huiles lubrifiantes
US4157309A (en) * 1977-09-30 1979-06-05 Chevron Research Company Mannich base composition
DE2917315A1 (de) * 1978-05-01 1979-11-15 Chevron Res Mannich-basen und deren erdalkalimetallsalze, verfahren zu deren herstellung und deren verwendung als schmieroeladditive
US4178259A (en) * 1978-05-01 1979-12-11 Chevron Research Company Dispersant Mannich base compositions
US4828742A (en) * 1987-07-24 1989-05-09 Exxon Chemical Patents, Inc. Lactone-modified, mannich base dispersant additives useful in oleaginous compositions
US4913830A (en) * 1987-07-24 1990-04-03 Exxon Chemical Patents Inc. Lactone-modified, mannich base dispersant additives useful in oleaginous compositions
US5166439A (en) * 1989-11-24 1992-11-24 Ethyl Petroleum Additives, Inc. Composition containing a mannich base of a partially sulfurized hindered phenol mixture
US5498809A (en) * 1992-12-17 1996-03-12 Exxon Chemical Patents Inc. Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
US5554310A (en) * 1992-12-17 1996-09-10 Exxon Chemical Patents Inc. Trisubstituted unsaturated polymers
US5663130A (en) * 1992-12-17 1997-09-02 Exxon Chemical Patents Inc Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
US6030930A (en) * 1992-12-17 2000-02-29 Exxon Chemical Patents Inc Polymers derived from ethylene and 1-butene for use in the preparation of lubricant disperant additives
US5814111A (en) * 1995-03-14 1998-09-29 Shell Oil Company Gasoline compositions
US5811379A (en) * 1996-06-17 1998-09-22 Exxon Chemical Patents Inc. Polymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such polymers and additives and use thereof (PT-1267)
US6066603A (en) * 1996-06-17 2000-05-23 Exxon Chemical Patents Inc. Polar monomer containing copolymers derived from olefins useful as lubricant and useful as lubricant and fuel oil additivies process for preparation of such copolymers and additives and use thereof
US6468948B1 (en) 1996-06-17 2002-10-22 Infineum Usa L.P. Polymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such polymers and additives and use thereof (PT-1267)
US6172015B1 (en) 1997-07-21 2001-01-09 Exxon Chemical Patents, Inc Polar monomer containing copolymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such copolymers and additives and use thereof

Also Published As

Publication number Publication date
GB1352760A (en) 1974-05-08
DE2161121A1 (de) 1972-07-06
IT959354B (it) 1973-11-10
AU3663271A (en) 1973-06-14
IE36704B1 (en) 1977-02-02
NL170305C (nl) 1982-10-18
DE2161121C2 (de) 1985-03-14
DK153165B (da) 1988-06-20
NL7117004A (enrdf_load_stackoverflow) 1972-06-13
BE776567A (fr) 1972-06-12
AU445627B2 (en) 1974-02-28
CA987343A (en) 1976-04-13
DK153165C (da) 1988-11-07
IE36704L (en) 1972-06-11
FR2117410A5 (enrdf_load_stackoverflow) 1972-07-21

Similar Documents

Publication Publication Date Title
US3741896A (en) Basic alkylene amine and sulfur bridged alkylphenoxides for use in lubricating oils
US3036003A (en) Lubricating oil composition
US3367943A (en) Process for preparing oil soluble additives which comprises reacting a c2 to c5 alkylene oxide with (a) reaction product of an alkenylsuccinic anhydride and an aliphaticpolyamine (b) reaction product of alkenylsuccinic anhydride, a c1 to c30 aliphatic hydrocarbon carboxylic acid and an aliphatic polyamine
EP0217591B1 (en) Normally liquid c18 to c24 monoalkyl catechols
US3546324A (en) Amine salts of dithiophosphoric acids
JPS6337199A (ja) 潤滑剤分散剤および酸化防止剤としてのコハク酸化合物の硼酸化反応生成物
JPH07508771A (ja) 混合摩擦調整剤を含有する潤滑油組成物
GB1583361A (en) Mannich base composition
US4171269A (en) Sulfurized lubricant composition
JPS6137316B2 (enrdf_load_stackoverflow)
US3793199A (en) Friction reducing agent for lubricants
CA2097828C (en) Fluorocarbon seal protective additives for lubrication oils
US3912707A (en) Amine and sulfur-containing alkylphenoxides
US3537999A (en) Lubricants containing benzothiadiazole
US3846318A (en) Antioxidant and extreme pressure lubricating oil additive
US3920567A (en) Novel oxazoline-alkyl acid phosphate adducts useful as ashless antiwear additives
EP0089844B1 (en) Boron-containing esters, their preparation and use as antioxidants
US3810838A (en) Oligomeric phosphorodiamidate
EP0031990B1 (en) A lubricating oil composition, an additive concentrate for lubricating oil and a method for imparting anti-corrosion properties to lubricating oil
US3813336A (en) Reaction products of amines and dithiophosphoric acids or salts
US3428563A (en) Alkenyl succinimide-antimony dithiophosphate combinations in lubricants
US3927104A (en) Polybutenyl-alkylene polyamine-polyalkanol lubricant additive
US3859219A (en) Bisphosphoramide-sulfur compound containing lubricant
US3446737A (en) Friction reducing additive comprising metal soap solubilized in oil by an ncontaining dispersant
US3856691A (en) Lubricating oil composition