US3301782A - Adducts of zinc compounds and lubricants containing same - Google Patents

Adducts of zinc compounds and lubricants containing same Download PDF

Info

Publication number
US3301782A
US3301782A US314886A US31488663A US3301782A US 3301782 A US3301782 A US 3301782A US 314886 A US314886 A US 314886A US 31488663 A US31488663 A US 31488663A US 3301782 A US3301782 A US 3301782A
Authority
US
United States
Prior art keywords
zinc
carbon atoms
oil
mole
primene
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
US314886A
Inventor
Edwin C Knowles
Frederic C Mccoy
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.)
Texaco Inc
Original Assignee
Texaco Inc
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 Texaco Inc filed Critical Texaco Inc
Priority to US314886A priority Critical patent/US3301782A/en
Application granted granted Critical
Publication of US3301782A publication Critical patent/US3301782A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
    • 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
    • C10M159/18—Complexes with metals
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms 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
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated 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
    • C10M2207/284—Esters of aromatic monocarboxylic 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
    • C10M2207/285—Esters of aromatic 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
    • 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
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/106—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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen 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
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2215/26—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
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/09—Complexes with metals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/241—Manufacturing joint-less pipes
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/242—Hot working
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/243—Cold working
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/245—Soft metals, e.g. aluminum
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/246—Iron or steel
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/247—Stainless steel

Definitions

  • novel oil-soluble adduct of the invention is formed from the reaction of an amine or a Schiff base and Zinc silicofiuoride, phosphate, hypophosphite, sulfite or thiocyanate. More particularly, the. adduct of the invention is represented by one of the following formulas:
  • R is-a hydrocarbyl radical having from 6 to 30 carbon atoms
  • R ' is selected from the group consisting of hydrogen and a hydrocarbyl radical having from 1 to 30 carbon atoms
  • .R is an aliphatic radical having from 1 to 30 carbon atoms, the sum of the carbon atoms in either of the compounds represented byv (a) and (b) being at least 12
  • y is an integer from 1 to 6
  • X is a zinc compound selected from the group consisting of zinc silicofluoride, zinc phosphite, zinc hypophosphite, zinc sulfite and zinc thiocyanate.
  • Amines which can, be employed to prepare the adduct 'of the invention are the amines having one or more hydrocarbyl radicals'in which the total number of carbon atoms in said amine is at least 12.
  • the requirement of 12 carbon atoms in the amine is critical to insure the oil solubility of the adduct.
  • Adducts formed from amines having less than 12 carbon atoms are generally not soluble in lubricating oils.
  • the effective amines correspond to the formula:
  • R is a hydrocarbyl radical having from 6 to 30 carbon atoms and R is hydrogen or a hydrocarbyl radical having from 1 to 30 carbon atoms.
  • R is generally ing the prescribed nprnberof carbon atoms.
  • R reprea branched chain alkyl radical because of the ready availice sents hydrogen or a hydrocarbyl radical having from 1 to 30 carbon atoms of the same types defined for R.
  • Examples of effective amines include laurylamine, tridecylamine, tetradecylamine, hexadecylamine, octadecylamine, eicosylamine, tricosylamine, noncosylamine, nonylphenylamine, dodecylphenylamine, methyldodecylamine, dimethyldodecylamine, methyloctadecylamine, and dimethyloctadecylamine.
  • Particularly preferred amines are certain commercially available mixtures of tertiary alkyl primary amines.
  • a mixture of tertiary alkyl primary amines in which the alkyl radical comprises a mixture of alkyl groups having from 11 to 14 carbon atoms is available under the name Primene 81-R.
  • Another commercially available amine is the mixture of tertiary alkyl primary amines in which the alkyl radical comprises a mixture of alkyl groups having 18 to 24 carbon atoms sold under thename Primene JM-T.
  • H RIIN ORI in which R and R have the values noted above and which is employed to form the adduct of the invention is prepared from an amine and an aldehyde. Specifically, equivalent amounts of a primary amine and an aldehyde are contacted either in the presence of or without a solvent. The reaction frequently occurs spontaneously although at times moderate heating is required. A mole of water splits out in the formation reaction of the Schifi base. The water formed by the reaction is generally removed by azeotroping with a solvent, such as toluene. It is essential that the sum of the carbon atoms represented by R' and R in the formula for the Schiff base amount to at least 12 in order to insure the oil solubility of the'adduct that is to be formed.
  • Amines which can be employed to prepare the Schiff base are the primary aliphatic amines. These amines are represented by the following formula:
  • R is an aliphatic hydrocarbyl radical having from 1 to 30 carbon atoms.
  • the preferred amines are those in which R is a branched chain alkyl radical having from about 12 to 24 carbon atoms.
  • Suitable primary amines for the Scange 'base reaction include butylamine, amylamine, hexyla- R'CHO in which R is hydrogen or a hydrocarbyl radical having from 1 to 30 carbon atoms.
  • the hydrocarbyl radi- .cal can be an aliphatic or an aromatic hydrocarbyl radical and preferably has from 1 to 10' carbon atoms.
  • aldehydes for this reaction include formaldehyde, 2-ethylhexaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, nonylaldehyde, palmitaldehyde, lauraldehyde, stearaldehyde, benzaldehyde and salicylaldehyde.
  • the adducts of the invention are prepared by mixing from 1 to 6 moles, preferably 1 to 4 moles, of a hydrocarbyl amine or a Schiif base defined above with a mole of zinc silicofluoride, zinc phosphite, zinc hypophosphite, zinc sulfite or zinc thiocyanate.
  • This reaction is usually exothermic and provision must generally be made to cool the reaction mixture. In particular, caution must be exercised to keep the reaction temperature below the decomposition temperature of the various components of the reaction product or adduct which generally means conducting the reaction at a temperature below about 200 C. The reaction generally goes to completion in a short reaction time.
  • adducts of the invention are given below.
  • the Schifi? base part of the adducts listed is expressed in terms of the components from which the Schiff bases are formed.
  • the mole ratio in parenthesis is the ratio of the amine or Schifi base to the zinc compound.
  • the lubricating composition of the invention is prepared by blending in a conventional way a minor amount of the oil-soluble, load-carrying hydrocarbyl amine or Schiff base zinc compound adduct described hereinabove into a suitable lubricating oil base.
  • the adduct is employed in an amount in the range of 0.05 to percent by weight based on the weight of the lubricating composition with the preferred proportions of the adduct being from 0.1 to 3 weight percent.
  • the base lubricating oil can be a mineral lubricating oil or a synthetic lubricating oil.
  • the mineral lubricating oil can be a predominantly paraflinic or naphthenic oil or can be a mixture of the two types of mineral oils.
  • the mineral oil will be a refined oil of predominantly parafiinic nature, having a viscosity in the range from 30 to 150 Saybolt Universal seconds at 210 F.
  • Various types of synthetic lubricating oil bases can be employed in preparing the lubricants of the invention.
  • Aliphatic ester, polyalkylene oxides, silicones, esters of phosphoric and salicylic acid and the highly fluorine-substituted hydrocarbons can be employed.
  • aliphatic esters examples include di-(2-ethylhexyl) sebacate, the dialkyl azelates, dialkyl suberates, and the dialkyl adipates such as di-hexyl azelate, di-(Z-ethylhexyl) azelate, di- 3,5,5-trimethylhexyl gluterate, di-(Z-ethylhexyl adiphate, triaimyl tricarb allylate, etc.
  • the polyalkylene oxide lubricants include polyisobutyloxide, polyisopropylene oxide diether, polyisopropylene oxide diesters, etc.
  • the silicone lubricants include methyl silicone, methylphenyl silicone and the silicate lubricants include tetraisooctyl silicate.
  • the highly fluorinated hydrocarbon lubricants include TAB LE I.L OAD .4 fluorinated oil, perlluorohydrocarbons and the like.
  • neopentyl glycol esters such as the neopentyl glycol propionates, neopentyl glycol butyrates and the neopentyl glycol caprylates and the trimethylol alkanes such as trimethylolethane, trimethylol propane, trimethylol pentane, trimethylol heptane and trimethylol dodecane and the like.
  • the phosphate esters include tricresyl phosphate, trioctyl phosphate and.tridecyl phosphate as well as mixed aryl and alkyl phosphates.
  • Example I The load carrying and anti-scuff properties of lubricating compositions of the invention were determined in a number of standard tests.
  • the Mean Hertz Load Test is run in a machine having four inch diameter bearing balls which are driven under load while being lubricated by the composition under test. The description of this test is set forth in US. Patent 2,600,058.
  • the Navy Four Ball Wear Test also measures the anti-wear properties of a lubricant.
  • the test machine employed comprises a system of four steel balls, three of which are in contact with each other in one plane in a fixed triangular position in a reservoir containing the oil sample and a fourth ball is above and in contact with the other three.
  • the upper ball is rotated at a speed of 1800 rpm while it is pressed against the lower three at a constant load of.28 kg. for four separate periods of 10, 40, and minutes.
  • the wear rate is calculated in microns per minutes.
  • the Mean Hertz Load was determined by means of the same equipment used in the Navy Four Ball Wear Test, using Federal Test Method Standard 791A, Method 6503.
  • Lubricating compositions illustrative of the invention were prepared from both mineral and synthetic lubricating oils.
  • the mineral lubricating oil was essentially a paraffinic lubricating oil having an SUS viscosity at 210 F. of about 100. This is designated as Base Oil A.
  • the synthetic lubricating oil consisted of di-2-ethylhexyl sebacate plus sebacic acid. This oil, which is commercially available as Plexol 201], is designated as Base Oil B in the example.
  • the adduct mole ratio indicated in parenthesis is the mole ratio of the hydrocarbylamine or of the Schiff base employed to the zinc compound.
  • Schifi Base A was formed by reacting a mole of Primene JM-T with a mole of Z-ethylhexaldehyde. The test results are given in Table I below.
  • the lubricating compositions containing the abovedescribed amine or Schiff base-zinc compound adducts have markedly improved load-carrying, wear and antiscuff properties. They also exhibit good corrosion resistance, oxidation resistance and storage stability. 'I hese valuable properties make the lubricants of the invention suitable for a broad range of lubrication applications.
  • the lubricating compositions of the invention can contain numerous additives conventionally used to improve the properties of lubricating oils. Commonly employed additives are the methacrylates as V1.
  • the alkylphenols as 7 RR N and RIIN C R! in which R is an alkyl radical having from 6 to 30 carbon atoms, R is selected from the group consisting of a hydrogen and an alkyl radical having from 1 to 30 carbon atoms and R" is an alkyl radical having from 1 to 30 carbon atoms, the sum of the carbon atoms in the compound represented by (a) and (b) being at least 12, with a mole of a zinc compound selected from the group consisting of zinc silicofluoride, zinc phosphite, zinc hypophosphite, zinc sulfite and zinc thiocyanate.
  • composition according to claim 1 in which said zinc compound is zinc silicofluoride.
  • composition according to claim 1 in which said zinc compound is zinc phosphite is zinc phosphite.
  • composition according to claim 1 in which said zinc compound is zinc sulfite.
  • a lubricating composition comprising a major proportion of a lubricating oil and 0.05 to 10 percent by Weight of an oil-soluble composition produced by reacting 1 to 6 moles of a compound represented by a formula selected from the group consisting of:
  • R is an alkyl radical having from 6 to 30 carbon atoms
  • R is selected from the group consisting of hydrogen and an alkyl radical having from 1 to 30 carbon atoms
  • R is an alkyl radical having from 1 to 30 carbon atoms, the sum .of the carbon atoms in the compound represented by (a) and (b) being at least 12, with a mole of a zinc compound selected from the group consisting of zinc silicofluoride, zinc phosphite, zinc hypophosphite, zinc sulfite and zinc thiocyanate.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)

Description

United States Patent 3 301 782 ADDUCTS OF ZINC COMPOUNDS AND LUBRI- CANTS CONTAINING SAME Edwin C. Knowles, Poughkeepsie, and Frederic C.
McCoy, Beacon, N.Y., assignors to Texaco Inc., New York, N.Y., a corporation of Delaware No Drawing. Filed Oct. 9, 1963, Ser. No. 314,886
13 Claims. (Cl.- 25246.4)
bricating conditions are commonly encountered in the lubrication of heavily loaded pinion and spur gears, gear trains, bearings, extrusion applications and the like. As a result, there is an increasing need for lubricating compositions having improved properties for these services.
A novel class of oil-soluble amine or Schiif base adducts of zinc compounds has been discovered which imparts greatly improved properties to lubricating oils. The lubricant compositions containing the adducts are particularly notable. for their improvement in load carrying and anti-scuff properties although they also exhibit addition-aladvantages in corrosion resistance, oxidation resistance and stability. These lubricating compositions provide the answer to some heretofore diflicult lubrication problems. I
The novel oil-soluble adduct of the invention is formed from the reaction of an amine or a Schiff base and Zinc silicofiuoride, phosphate, hypophosphite, sulfite or thiocyanate. More particularly, the. adduct of the invention is represented by one of the following formulas:
(a),. I I
-(RR2N) X and R"N=oR' ,.X in which R is-a hydrocarbyl radical having from 6 to 30 carbon atoms, R 'is selected from the group consisting of hydrogen and a hydrocarbyl radical having from 1 to 30 carbon atoms,.R is an aliphatic radical having from 1 to 30 carbon atoms, the sum of the carbon atoms in either of the compounds represented byv (a) and (b) being at least 12, y is an integer from 1 to 6 and X is a zinc compound selected from the group consisting of zinc silicofluoride, zinc phosphite, zinc hypophosphite, zinc sulfite and zinc thiocyanate. 1
Amines which can, be employed to prepare the adduct 'of the invention are the amines having one or more hydrocarbyl radicals'in which the total number of carbon atoms in said amine is at least 12. The requirement of 12 carbon atoms in the amine is critical to insure the oil solubility of the adduct. Adducts formed from amines having less than 12 carbon atoms are generally not soluble in lubricating oils. The effective amines correspond to the formula:
- RR N wherein R is a hydrocarbyl radical having from 6 to 30 carbon atoms and R is hydrogen or a hydrocarbyl radical having from 1 to 30 carbon atoms. R is generally ing the prescribed nprnberof carbon atoms. R reprea branched chain alkyl radical because of the ready availice sents hydrogen or a hydrocarbyl radical having from 1 to 30 carbon atoms of the same types defined for R.
Examples of effective amines include laurylamine, tridecylamine, tetradecylamine, hexadecylamine, octadecylamine, eicosylamine, tricosylamine, noncosylamine, nonylphenylamine, dodecylphenylamine, methyldodecylamine, dimethyldodecylamine, methyloctadecylamine, and dimethyloctadecylamine. Particularly preferred amines are certain commercially available mixtures of tertiary alkyl primary amines. For example, a mixture of tertiary alkyl primary amines in which the alkyl radical comprises a mixture of alkyl groups having from 11 to 14 carbon atoms is available under the name Primene 81-R. Another commercially available amine is the mixture of tertiary alkyl primary amines in which the alkyl radical comprises a mixture of alkyl groups having 18 to 24 carbon atoms sold under thename Primene JM-T.
The Schiff base which which corresponds to the formula:
H RIIN ORI in which R and R have the values noted above and which is employed to form the adduct of the invention is prepared from an amine and an aldehyde. Specifically, equivalent amounts of a primary amine and an aldehyde are contacted either in the presence of or without a solvent. The reaction frequently occurs spontaneously although at times moderate heating is required. A mole of water splits out in the formation reaction of the Schifi base. The water formed by the reaction is generally removed by azeotroping with a solvent, such as toluene. It is essential that the sum of the carbon atoms represented by R' and R in the formula for the Schiff base amount to at least 12 in order to insure the oil solubility of the'adduct that is to be formed.
Amines which can be employed to prepare the Schiff base are the primary aliphatic amines. These amines are represented by the following formula:
in which R is an aliphatic hydrocarbyl radical having from 1 to 30 carbon atoms. The preferred amines are those in which R is a branched chain alkyl radical having from about 12 to 24 carbon atoms.
Examples of suitable primary amines for the Schilf 'base reaction include butylamine, amylamine, hexyla- R'CHO in which R is hydrogen or a hydrocarbyl radical having from 1 to 30 carbon atoms. The hydrocarbyl radi- .cal can be an aliphatic or an aromatic hydrocarbyl radical and preferably has from 1 to 10' carbon atoms. EX- amples of effective aldehydes for this reaction include formaldehyde, 2-ethylhexaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, nonylaldehyde, palmitaldehyde, lauraldehyde, stearaldehyde, benzaldehyde and salicylaldehyde.
The adducts of the invention are prepared by mixing from 1 to 6 moles, preferably 1 to 4 moles, of a hydrocarbyl amine or a Schiif base defined above with a mole of zinc silicofluoride, zinc phosphite, zinc hypophosphite, zinc sulfite or zinc thiocyanate. This reaction is usually exothermic and provision must generally be made to cool the reaction mixture. In particular, caution must be exercised to keep the reaction temperature below the decomposition temperature of the various components of the reaction product or adduct which generally means conducting the reaction at a temperature below about 200 C. The reaction generally goes to completion in a short reaction time.
The reaction of a zinc compound with an amine or a Schilf base to form the adduct of the invention is unpredictable. Many zinc compounds do not form adducts with either the amines or Schitf bases. For example, zinc fluoride, zinc borate, zinc sulfate, zinc sulfide'and zinc oxide would not form adducts with the amines or Schiflf bases.
Examples of adducts of the invention are given below. For convenience, the Schifi? base part of the adducts listed is expressed in terms of the components from which the Schiff bases are formed. The mole ratio in parenthesis is the ratio of the amine or Schifi base to the zinc compound.
Primene JM-Tzzinc sulfite (4:1)
' Primene JM-Tzzinc phosphite (2:1)
Primene JM-Tzzinc phosphite (1:1)
Primene JM-T2zinc silicofluoride (2: 1)
Primene J M-T:zinc thiocyanate (2:1)
Primene JM-T2zinc hyp-ophosphite (3: 1)
Primene 81-Rzzinc silicofluoride (2:1)
Primene 81-Rzzinc thiocyanate (2:1)
Primene JM-T/formaldehydezzinc phosphite (2:1) Primene JM-T/Z-ethylhexaldehyde:zinc thiocyanate (2:1), and Primene JM-T/Z-ethylhexaldehyde:zinc silicofluoride The lubricating composition of the invention is prepared by blending in a conventional way a minor amount of the oil-soluble, load-carrying hydrocarbyl amine or Schiff base zinc compound adduct described hereinabove into a suitable lubricating oil base. Generally, the adduct is employed in an amount in the range of 0.05 to percent by weight based on the weight of the lubricating composition with the preferred proportions of the adduct being from 0.1 to 3 weight percent.
The base lubricating oil can be a mineral lubricating oil or a synthetic lubricating oil. The mineral lubricating oil can be a predominantly paraflinic or naphthenic oil or can be a mixture of the two types of mineral oils.
Generally, the mineral oil will be a refined oil of predominantly parafiinic nature, having a viscosity in the range from 30 to 150 Saybolt Universal seconds at 210 F.
Various types of synthetic lubricating oil bases can be employed in preparing the lubricants of the invention. Aliphatic ester, polyalkylene oxides, silicones, esters of phosphoric and salicylic acid and the highly fluorine-substituted hydrocarbons can be employed. Examples of the aliphatic esters include di-(2-ethylhexyl) sebacate, the dialkyl azelates, dialkyl suberates, and the dialkyl adipates such as di-hexyl azelate, di-(Z-ethylhexyl) azelate, di- 3,5,5-trimethylhexyl gluterate, di-(Z-ethylhexyl adiphate, triaimyl tricarb allylate, etc. The polyalkylene oxide lubricants include polyisobutyloxide, polyisopropylene oxide diether, polyisopropylene oxide diesters, etc. The silicone lubricants include methyl silicone, methylphenyl silicone and the silicate lubricants include tetraisooctyl silicate. The highly fluorinated hydrocarbon lubricants include TAB LE I.L OAD .4 fluorinated oil, perlluorohydrocarbons and the like.
Other effective synthetic lubricating oils include the neopentyl glycol esters such as the neopentyl glycol propionates, neopentyl glycol butyrates and the neopentyl glycol caprylates and the trimethylol alkanes such as trimethylolethane, trimethylol propane, trimethylol pentane, trimethylol heptane and trimethylol dodecane and the like. Examples of the phosphate esters include tricresyl phosphate, trioctyl phosphate and.tridecyl phosphate as well as mixed aryl and alkyl phosphates.
Example I The load carrying and anti-scuff properties of lubricating compositions of the invention were determined in a number of standard tests. The Mean Hertz Load Test is run in a machine having four inch diameter bearing balls which are driven under load while being lubricated by the composition under test. The description of this test is set forth in US. Patent 2,600,058.
In the Ryder Gear Test (Federal Test Method 6508), the lubricant being tested is employed to lubricate two spur gears in a Pratt and Whitney Gear and Lubricating Tester. This tester was operated with a gear speed of 10,000 rpm. and with an oil inlet temperature of 165 F. The loading pressure of 5.0 p.s.i. was applied during break-in. After 10 minutes the tester was shut down and the gear examined for the percentage of tooth area scuff on each tooth. This procedure was repeated using a high load pressure with increments of 5 psi. until 22.5 percent of the total tooth area on the driving gear had been scuffed, the load applied in this run being considered the scuif load. The tooth load in pounds per inch of tooth width was then calculated.
The Navy Four Ball Wear Test also measures the anti-wear properties of a lubricant. The test machine employed comprises a system of four steel balls, three of which are in contact with each other in one plane in a fixed triangular position in a reservoir containing the oil sample and a fourth ball is above and in contact with the other three. In carrying out the test, the upper ball is rotated at a speed of 1800 rpm while it is pressed against the lower three at a constant load of.28 kg. for four separate periods of 10, 40, and minutes. The wear rate is calculated in microns per minutes.
The Mean Hertz Load was determined by means of the same equipment used in the Navy Four Ball Wear Test, using Federal Test Method Standard 791A, Method 6503.
Lubricating compositions illustrative of the invention were prepared from both mineral and synthetic lubricating oils. The mineral lubricating oil was essentially a paraffinic lubricating oil having an SUS viscosity at 210 F. of about 100. This is designated as Base Oil A. The synthetic lubricating oil consisted of di-2-ethylhexyl sebacate plus sebacic acid. This oil, which is commercially available as Plexol 201], is designated as Base Oil B in the example. The adduct mole ratio indicated in parenthesis is the mole ratio of the hydrocarbylamine or of the Schiff base employed to the zinc compound. Schifi Base A was formed by reacting a mole of Primene JM-T with a mole of Z-ethylhexaldehyde. The test results are given in Table I below.
CARRYING AND ANTI-SCUFF PROPERTIES Navy Adduct (Mole Ratio) Percent Base Ryder Gear Mean Hertz Four Ball By Wt. 011 Test, p.p.i. Load Wear Test,
micron/min.
None I A Primene JM-T/ZnHPOg (3: 1) 1. 0 A Primene .TM-T/ZnSiF (2:1)- 1. 0 A Primene .TM-T/ZnSiFt (2: 1) 2. 0 A Schifis Base A/ZnHPOa (4:1)" 1. 0 A Sehifis Base A/Z11(SON) (2:1) 1. 0 A Primene .TM-T/ZMSCN): (2:1) 1.0 A Primene .TM-T/ZnSOa (4:1) 1. 0 Primene JM-T/ZnHPOa (2:1) 0.5 A None B Primene JM-T/ZnSiF (2:3) l. 0 B
The lubricating compositions containing the abovedescribed amine or Schiff base-zinc compound adducts have markedly improved load-carrying, wear and antiscuff properties. They also exhibit good corrosion resistance, oxidation resistance and storage stability. 'I hese valuable properties make the lubricants of the invention suitable for a broad range of lubrication applications.
It is understood that the lubricating compositions of the invention can contain numerous additives conventionally used to improve the properties of lubricating oils. Commonly employed additives are the methacrylates as V1.
improvers and pour point depressors, the alkylphenols as 7 RR N and RIIN C R! in which R is an alkyl radical having from 6 to 30 carbon atoms, R is selected from the group consisting of a hydrogen and an alkyl radical having from 1 to 30 carbon atoms and R" is an alkyl radical having from 1 to 30 carbon atoms, the sum of the carbon atoms in the compound represented by (a) and (b) being at least 12, with a mole of a zinc compound selected from the group consisting of zinc silicofluoride, zinc phosphite, zinc hypophosphite, zinc sulfite and zinc thiocyanate.
2. A composition according to claim 1 in which said zinc compound is zinc silicofluoride.
3. A composition according to claim 1 in which said zinc compound is zinc phosphite.
4. A composition according to claim 1 in which said zinc compound is zinc hypophosphite.
5. A composition according to claim 1 in which said zinc compound is zinc sulfite.
6. A composition according to claim 1 in which said zinc compound is zinc thiocyanate.
7. As a new composition, the product produced by reacting 4 moles of a C1844 alkyl primary amine with a mole of zinc silicofluoride.
8. As a new composition, the product produced by reacting 4 moles of a Schifi base with a mole of zinc phosphite, said Schiff base being obtained by reacting a mole of a C1844 alkyl primary amine with a mole of 2-ethy1- hexaldehyde.
9. As a new composition, the product produced by reacting 2 moles of a Schiff base with a mole of zinc thiocyanate, said Schiff base being obtained by reacting a mole of a C alkyl primary amine with a mole of Z-ethylhexaldehyde.
10. A lubricating composition comprising a major proportion of a lubricating oil and 0.05 to 10 percent by Weight of an oil-soluble composition produced by reacting 1 to 6 moles of a compound represented by a formula selected from the group consisting of:
(a) RR N and in which R is an alkyl radical having from 6 to 30 carbon atoms, R is selected from the group consisting of hydrogen and an alkyl radical having from 1 to 30 carbon atoms and R is an alkyl radical having from 1 to 30 carbon atoms, the sum .of the carbon atoms in the compound represented by (a) and (b) being at least 12, with a mole of a zinc compound selected from the group consisting of zinc silicofluoride, zinc phosphite, zinc hypophosphite, zinc sulfite and zinc thiocyanate.
11. A lubricating composition according to claim 10 in which said oil-soluble compound is the product produced by reacting 4 moles of a C1844 alkyl primary amine with a mole of zinc silicofiuoride.
12. A lubricating composition according to claim 10 in which said oil-soluble compound is the product produced by reacting 4 moles of a Schitf base with a mole of Zinc phosphite, said Schiit base being obtained by reacting a mole of a C alkyl primary aminne with a mole of Z-ethylhexaldehyde.
13. A lubricating composition according to claim 10 in which said oil-soluble compound is the product produced by reacting 2 moles of a Schitf base with a mole of. zinc thiocyanate, said Schiff base being obtained by reacting a mole of a C1844 alkyl primary amine with a mole of Z-ethylhexaldehyde.
References Cited by the Examiner UNITED STATES PATENTS 2,112,567 3/1938 Havas 260--429.9 2,725,358 11/1955 Kluge et al 252-42.7 3,107,739 10/ 1963 Mathews 260429.9
DANIEL E. WYMAN, Primary Examiner.
L- G- X L R. 0S v As i tant Exam ner,

Claims (1)

10. A LUBRICATING COMPOSITION COMPRISING A MAJOR PROPORTION OF A LUBRICATING OIL AND 0.05 TO 10 PERCENT BY WEIGHT OF AN OIL-SOLUBLE COMPOSITION PRODUCED BY REACTING 1 TO 6 MOLES OF A COMPOUND REPRESENTED BY A FORMULA SELECTED FROM THE GROUP CONSISTING OF: (A) RR''2N
US314886A 1963-10-09 1963-10-09 Adducts of zinc compounds and lubricants containing same Expired - Lifetime US3301782A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US314886A US3301782A (en) 1963-10-09 1963-10-09 Adducts of zinc compounds and lubricants containing same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US314886A US3301782A (en) 1963-10-09 1963-10-09 Adducts of zinc compounds and lubricants containing same

Publications (1)

Publication Number Publication Date
US3301782A true US3301782A (en) 1967-01-31

Family

ID=23221911

Family Applications (1)

Application Number Title Priority Date Filing Date
US314886A Expired - Lifetime US3301782A (en) 1963-10-09 1963-10-09 Adducts of zinc compounds and lubricants containing same

Country Status (1)

Country Link
US (1) US3301782A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3505223A (en) * 1967-03-30 1970-04-07 Ethyl Corp Lubricant compositions
US4728446A (en) * 1984-07-31 1988-03-01 The Dow Chemical Company Corrosion inhibitor for brines
WO1991018075A1 (en) * 1990-05-16 1991-11-28 N.V. Bekaert S.A. Additive for lubricants containing a metal complex
US9540595B2 (en) 2013-08-26 2017-01-10 The Procter & Gamble Company Compositions comprising alkoxylated polyalkyleneimines having low melting points

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2112567A (en) * 1937-05-25 1938-03-29 Du Pont Complex salts of zinc hydrosulphite and 1,2-aliphatic diamines and process for preparing them
US2725358A (en) * 1952-05-10 1955-11-29 Texas Co Lubricating oils containing hydroxymetal oxyarylalkyl amines
US3107739A (en) * 1960-10-31 1963-10-22 Magnet Cove Barium Corp Well fluids and additive therefor

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2112567A (en) * 1937-05-25 1938-03-29 Du Pont Complex salts of zinc hydrosulphite and 1,2-aliphatic diamines and process for preparing them
US2725358A (en) * 1952-05-10 1955-11-29 Texas Co Lubricating oils containing hydroxymetal oxyarylalkyl amines
US3107739A (en) * 1960-10-31 1963-10-22 Magnet Cove Barium Corp Well fluids and additive therefor

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3505223A (en) * 1967-03-30 1970-04-07 Ethyl Corp Lubricant compositions
US4728446A (en) * 1984-07-31 1988-03-01 The Dow Chemical Company Corrosion inhibitor for brines
WO1991018075A1 (en) * 1990-05-16 1991-11-28 N.V. Bekaert S.A. Additive for lubricants containing a metal complex
BE1004265A3 (en) * 1990-05-16 1992-10-20 Bekaert Sa Nv Additive lubricants comprising metal complex.
TR25289A (en) * 1990-05-16 1993-01-01 Bekaert Sa Nv ADDITIVES WITH A METAL COMPLEX FOR LUBRICANTS
US9540595B2 (en) 2013-08-26 2017-01-10 The Procter & Gamble Company Compositions comprising alkoxylated polyalkyleneimines having low melting points

Similar Documents

Publication Publication Date Title
US3224971A (en) Borate esters and lubricant compositions containing said esters
US2573568A (en) Lubricant composition containing dialkyl trihaloalkane phosphonate as an extreme pressure agent
US4089790A (en) Synergistic combinations of hydrated potassium borate, antiwear agents, and organic sulfide antioxidants
US3185644A (en) Lubricating compositions containing amine salts of boron-containing compounds
US3169923A (en) Oil of lubricating viscosity
US3992307A (en) Lubricant composition of improved antioxidant properties
US3203895A (en) Lubricating oils containing amine salts of phosphates
US2321517A (en) Lubricant composition
US2599761A (en) Extreme pressure lubricant
US2353558A (en) Addition agent for lubricating oil and method of making same
US2628941A (en) Extreme pressure lubricant
US3301782A (en) Adducts of zinc compounds and lubricants containing same
US3134737A (en) Novel titanium compound and lubricating composition containing said compound
US2780597A (en) Lubricating compositions
US4822505A (en) Load-carrying grease
US5763370A (en) Friction-reducing and antiwear/EP additives for lubricants
US3422017A (en) Lubricant compositions containing amine salts
US3216939A (en) Stabilization of lubricants
US3502581A (en) Antioxidant composition and use thereof
US3480551A (en) Lubricating composition
US3269950A (en) Lubricating composition containing amide, imide and thiocyanate complexes of zinc and tin
US3275559A (en) Hydraulic fluid
US3507918A (en) Amine salts of mono- and difluorophosphoric acids
EP0739405A1 (en) Additives for lubricants
US2628939A (en) Mineral oil composition