US20040038835A1 - Engine oils that are non-aggressive towards lead - Google Patents

Engine oils that are non-aggressive towards lead Download PDF

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Publication number
US20040038835A1
US20040038835A1 US10/465,423 US46542303A US2004038835A1 US 20040038835 A1 US20040038835 A1 US 20040038835A1 US 46542303 A US46542303 A US 46542303A US 2004038835 A1 US2004038835 A1 US 2004038835A1
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Prior art keywords
triazole
group
formula
aminomethyl
component
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David Chasan
Sunray Difrancesco
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BASF Corp
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Assigned to CIBA SPECIALTY CHEMICALS CORP. reassignment CIBA SPECIALTY CHEMICALS CORP. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHASAN, DAVID E., DIFRANCESCO, SUNRAY
Publication of US20040038835A1 publication Critical patent/US20040038835A1/en
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    • 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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38—Heterocyclic nitrogen compounds
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised compounds
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    • C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
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    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
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    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
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    • 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
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    • 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
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C10M2219/068—Thiocarbamate metal salts
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
    • C10M2219/083—Dibenzyl sulfide
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    • 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
    • C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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    • 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
    • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
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    • 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
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    • 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
    • C10M2223/047—Thioderivatives not containing metallic elements
    • 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
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    • 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
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    • 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
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/12—Groups 6 or 16
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/14—Metal deactivation
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines

Definitions

  • the present invention relates to engine oil (engine fluid) compositions that are non-aggressive towards lead.
  • Engine oil specifications are becoming more stringent in the way of performance requirements, and new formulations are under development to meet these new specifications.
  • Engine oil specifications are defined in ASTM D 4485.
  • the new engine oil formulations under development comprise certain additive chemistries. Many of these additive chemistries are corrosive to lead. It is difficult for formulators to meet the present engine oil specifications by employing certain beneficial additives while also meeting the specification for lead corrosion.
  • certain components of formulated engine oils that cause lead corrosion include certain detergents, antiwear additives, friction modifiers and antioxidants. Many such desired additive chemistries are disqualified from use due to causing engine oil formulations to not meet industry specifications for limits on lead corrosion.
  • desired additive chemistries that are aggressive towards lead and are otherwise disqualified from use in engine oils include sulfur-containing additives and certain vegetable oil-derived friction modifiers.
  • engine oils that comprise certain 1,2,4-triazole metal deactivators are especially non-aggressive towards lead, for example lead engine parts such as bearings.
  • the engine oils according to this invention meet corrosion protection performance requirements of diesel lubricant specifications defined in ASTM D 4485.
  • the engine oils of this invention are diesel and universal oils. Universal oils encompass both diesel oils and passenger car oils.
  • the engine oils are employed in internal combustion engines, for example, in motor vehicles fitted, for example, with engines of the Otto, Diesel, two-stroke, Wankel or orbital type.
  • the present invention relates to an engine oil composition that is non-aggressive towards lead,
  • composition comprises
  • At least one oil additive that is aggressive towards lead which is selected from the group consisting of antioxidants, antiwear additives, dispersants, detergents, antifoam additives, viscosity index improvers, copper passivators, rust inhibitors, pourpoint depressants, demulsifiers and friction modifiers,
  • R 1 and R 2 are the same or different and are C 1 -C 20 alkyl, C 3 -C 20 alkenyl, C 5 -C 12 cycloalkyl, C 7 -C 13 aralkyl or C 6 -C 10 aryl, or R 1 and R 2 , together with the nitrogen atom to which they are each attached may form a 5-, 6- or 7-membered heterocylic residue, or R 1 and R 2 are a group of formula
  • X is O, S or N
  • R 3 is hydrogen or C 1 -C 20 alkyl
  • R 4 is C 1 -C 12 alkylene
  • n is 0 or an integer from 1 to 6,
  • R 1 and R 2 are a group of formula
  • R 2 is a group of formula (II) and R 1 is a group of formula
  • m is 0 or 1 and, when m is zero, A is a group of formula (II) and, when m is 1, A is alkylene or C 6 -C 10 arylene and R 5 is a group of formula (II), and
  • R 4 is for example a C 1 -C 6 alkylene group, for instance a C 2 -C 3 alkylene.
  • n is for instance 0, 1, 2, 3, 4, 5 or 6.
  • Alkyl is straight or branched chain and is for example methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl or n-eicosyl.
  • Alkenyl is straight or branched chain and is for example prop-2-enyl, but-2-enyl, 2-methyl-prop-2-enyl, pent-2-enyl, hexa-2,4-dienyl, dec-10-enyl or eicos-2-enyl.
  • Cylcoalkyl is for example cyclopentyl, cyclohexyl, cyclooctyl, cyclodecyl, adamantyl or cyclododecyl.
  • Aralkyl is for example benzyl, 2-phenylethyl, benzhydryl or naphthylmethyl.
  • Aryl is for example phenyl or naphthyl.
  • the heterocyclic group is for example a morpholine, pyrrolidine, piperidine or a perhydroazepine ring.
  • Alkylene moieties include for example methylene, ethylene, 1:2- or 1:3-propylene, 1:4-butylene, 1:6-hexylene, 1:8-octylene, 1:10-decylene and 1:12-dodecylene.
  • Arylene moieties include for example phenylene and naphthylene.
  • the present compound of formula (I) is for example 1-(di-isooctylaminomethyl) triazole, that is 1-(di-isooctylaminomethyl)-1,2,4-triazole, or is 1-(di-(2-ethylhexyl)aminomethyl)1,2,4-triazole.
  • the base fluids in accordance with the invention utilize mineral oil based fluids (API Group I, II and III), poly- ⁇ -olefins—PAOs (API Group IV), esters (API Group V), other synthetic fluids, natural oils that are animal or vegetable in origin, and mixtures thereof.
  • the base fluids are of suitable viscosity for utilization in engine oil applications.
  • the present compounds of formula (I) are employed at concentrations of about 0.01 to about 1.0% by weight, based on the weight of the formulated engine oil.
  • the compounds of formula (I) are present from about 0.02 to about 0.5 weight percent.
  • the compounds of formula (I) are present from about 0.02 to about 0.5 weight percent.
  • from about 0.03 to about 0.3 weight percent For instance from about 0.01 to about 0.5 or from about 0.01 to about 0.3 weight percent.
  • from about 0.03 to about 1.0 or from about 0.03 to about 0.5 weigh percent.
  • antioxidants of component (c) are selected from:
  • alkylated monophenols for example 2,6-di-tert-butyl-4-methylphenol, 2-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-iso-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2-(a-methyl-cyclohexyl)-4,6-dimethylphenol, 2,6-di-octadecyl-4-methylphenol, 2,4,6-tri-cyclo-hexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, linear or sidechain-branched nonylphenols, for example 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6-(1′-methyl-undec-1′-yl)phenol,
  • alkylthiomethylphenols for example 2,4-di-octylthiomethyl-6-tert-butylphenol, 2,4-di-octylthiomethyl-6-methylphenol, 2,4-di-octylthiomethyl-6-ethylphenol or 2,6-di-dodecylthiomethyl-4-nonylphenol,
  • hydroquinones and alkylated hydroquinones for example 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butyl-hydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate or bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate,
  • tocopherols for example ⁇ -, ⁇ -, ⁇ - or ⁇ -tocopherol or mixtures thereof (vitamin E),
  • hydroxylated thiodiphenyl ethers for example 2,2′-thiobis(6-tert-butyl-4-methylphenol), 2,2′-thiobis(4-octylphenol), 4,4′-thiobis(6-tert-butyl-3-methylphenol), 4,4′-thiobis-(6-tert-butyl-2-methylphenol), 4,4′-thiobis(3,6-di-sec.-amylphenol) or 4,4′-bis(2,6-dimethyl-4-hydroxyphenyl) disulfide,
  • 2,2′-thiobis(6-tert-butyl-4-methylphenol 2,2′-thiobis(4-octylphenol), 4,4′-thiobis(6-tert-butyl-3-methylphenol), 4,4′-thiobis-(6-tert-butyl-2-methylphenol), 4,4′-thiobis(3,6-di-sec.-amylphenol) or 4,4′-bis
  • alkylidenebisphenols for example 2,2′-methylenebis(6-tert-butyl-4-methylphenol), 2,2′-methylenebis(6-tert-butyl-4-ethylphenol), 2,2′-methylenebis(4-methyl-6-(alpha-methylcyclohexyl)-phenol), 2,2′-methylenebis(4-methyl-6-cyclohexylphenol), 2,2′-methylenebis(6-nonyl-4-methylphenol), 2,2′-methylenebis(4,6-di-tert-butylphenol), 2,2′-ethylidenebis(4,6-di-tert-butylphenol), 2,2′-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2′-methylenebis(6-(alpha-methylbenzyl)-4-nonylphenol), 2,2′-methylene-bis(6-(alpha,alpha-dimethyl
  • O- N- and S-benzyl compounds for example 3,5,3′,5′-tetra-tert-butyl-4,4′-dihydroxydibenzyl ether, octadecyl 4-hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecyl 4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate, tris(3,5-di-tert-butyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl) sulfide or isooctyl 3,5-di-tert-butyl-4-hydroxy-benzylmercaptoacetate,
  • hydroxybenzylated malonates for example-dioctadecyl 2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonate, dioctadecyl 2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)-malonate, di-dodecyl mercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-malonate or di(4-(1,1,3,3-tetramethylbutyl)phenyl)2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate,
  • aromatic hydroxybenzyl compounds for example 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene or 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol,
  • triazine compounds for example 2,4-bisoctylmercapto-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazin e, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,6-
  • benzylphosphonates for example dimethyl 2,5-di-tert-butyl-4-hydroxybenzyl-phosphonate, diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl 5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate or the calcium salt of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid,
  • acylaminophenols for example 4-hydroxylauranilide, 4-hydroxystearanilide or octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate,
  • amides of ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid e.g. N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamine, N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamine or N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine,
  • N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamine N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamine or N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine
  • amine-type antioxidants for example N,N′-diisopropyl-p-phenylenediamine, N,N′-di-sec-butyl-p-phenylenediamine, N,N′-bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N′-bis(1-ethyl-3-methyl-pentyl)-p-phenylenediamine, N,N′-bis(1-methyl-heptyl)-p-phenylendiamine, N,N′-dicyclohexyl-p-phenylenediamine, N,N′-diphenyl-p-phenylenediamine, N,N′-di-(naphth-2-yl)-p-phenylenediamine, N-isopropyl-N′-phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N
  • p,p′-di-tert-octyidiphenyl-amine 4-n-butylaminophenol, 4-butyrylamino-phenol, 4-nonanoylamino-phenol, 4-dodecanoylaminophenol, 4-octadecanoylamino-phenol, di-(4-methoxyphenyl)-amine, 2,6-di-tert-butyl-4-dimethylaminomethyl-phenol, 2,4′-diamino-diphenylmethane, 4,4′-diamino-diphenylmethane, N,N,N′,N′-tetramethyl-4,4′-diamino-diphenylmethane, 1,2-di-((2-methyl-phenyl)-amino)-ethane, 1,2-di-(phenylamino)propane, (o-tolyl)biguanide, di(4-(1′,3′-d
  • antiwear additives of component (c) are selected from:
  • dihydrocarbyl dithiophosphate metal salts where the metal is aluminum, lead, tin manganese, cobalt, nickel, zinc or copper, but most often zinc.
  • the zinc salt (zinc dialkyl dithiophosphate) is represented as
  • R and R′ are independently C 1 -C 20 alkyl, C 3 -C 20 alkenyl, C 5 -C 12 cycloalkyl, C 7 -C 13 aralkyl or C 6 -C 10 aryl, for example R and R′ are independently C 1 -C 12 alkyl,
  • sulfur- and/or phosphorus- and/or halogen-containing compounds such as sulfurized olefins and vegetable oils, tritolyl phosphate, tricresyl phosphate, chlorinated paraffins, alkyl and aryl di- and trisulfides, amine salts of mono- and dialkyl phosphates, amine salts of methylphosphonic acid, diethanolaminomethyltolyltriazole, di(2-ethylhexyl)-aminomethyltolyltriazole, derivatives of 2,5-dimercapto-1,3,4-thiadiazole, ethyl ((bisisopropyloxyphosphinothioyl)thio)propionate, triphenyl thiophosphate (triphenyl phosphorothioate), tris(alkylphenyl) phosphorothioates and mixtures thereof (for example tris(isononylphenyl) phosphorot
  • the dispersants of component (c) are selected from:
  • succinic-based dispersants that are reaction products of a olefin polymer and succinic acylating agent (acid, anhydride, ester or halide) further reacted with an organic hydroxy compound and/or an amine,
  • amides and esters such as reaction products of a hydrocarbyl acylating agent and a a polyhydric aliphatic alcohol (such as glycerol, pentaerythritol or sorbitol).
  • Ashless (metal-free) polymeric materials that usually contain an oil soluble high molecular weight backbone linked to a polar functional group that associates with particles to be dispersed are typically used as dispersants.
  • Commonly used hydrocarbon backbone materials are olefin polymers and copolymers, i.e.—ethylene, propylene, butylene, isobutylene, styrene; there may or may not be further functional groups incorporated into the backbone of the polymer.
  • Polar materials such as amines, alcohols, amides or esters are attached to the backbone via a bridge.
  • the detergents of component (c) are selected from:
  • Calcium, magnesium, barium, sodium or lithium salts of organic acids for example sulphonates, alkylphenates, sulfurised alkyl phenates, carboxylates, salicylates, phosphonates, thiophosphonates and phosphinates.
  • the salts may be neutral or may be overbased by for example metal hydroxides or carbonates.
  • antifoam additives of component (c) are selected from:
  • the viscosity index improvers of component (c) are selected from:
  • the copper passivators of component (c) are selected from:
  • benzotriazoles and their derivatives for example 4- or 5-alkylbenzotriazoles (e.g. tolutriazole) and derivatives thereof, 4,5,6,7-tetrahydrobenzotriazole, 5,5′-methylenebisbenzotriazole; Mannich bases of benzotriazole or tolutriazole, such as 1-(di(2-ethylhexyl)aminomethyl)tolutriazole and 1-(di-(2-ethylhexyl)aminomethyl)-benzotriazole; alkoxyalkylbenzotriazoles, such as 1-(nonyloxymethyl)-benzotriazole, 1-(1-butoxyethyl)-benzotriazole or 1-(1-cyclohexyloxybutyl)-tolutriazole,
  • imidazole derivatives for example 4,4′-methylenebis(2-undecyl-5-methyl-imidazole), bis((N-methyl)imidazol-2-yl)carbinol octyl ether,
  • sulfur-containing heterocyclic compounds for example 2-mercaptobenzothiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2,5-dimercaptobenzothiadiazole and derivatives thereof or 3,5-bis(di(2-ethylhexyl)aminomethyl)-1,3,4-thiadiazolin-2-one,
  • amino compounds for example salicylidenepropylenediamine, salicylaminoguanidine or salts thereof.
  • the rust inhibitors of component (c) are selected from:
  • heterocyclic compounds for example: substituted imidazolines or oxazolines, for instance 2-heptadecenyl-1-(2-hydroxyethyl)-imidazoline,
  • phosphorus-containing compounds for example amine salts of phosphoric acid, phosphoric acid partial esters or phosphonic acid partial esters or zinc dialkyldithiophosphates,
  • sulfur-containing compounds for example barium dinonylnaphthalene-sulfonates, calcium petroleumsulfonates, alkylthio-substituted aliphatic carboxylic acids, esters of aliphatic 2-sulfocarboxylic acids or salts thereof,
  • glycerine derivatives for example glycerine monooleate, 1-(alkylphenoxy)-3-(2-hydroxyethyl)glycerines, 1-(alkylphenoxy)-3-(2,3-dihydroxypropyl)glycerines or 2-carboxyalkyl-1,3-dialkylglycerines.
  • the pour point depressants of component (c) are selected from:
  • the demulsifiers of component (c) are selected from:
  • the friction modifiers of component (c) are selected from:
  • Fatty acids and their derivatives i.e. natural esters of fatty acids such as glycerol monooleate), amides, imides and amines (i.e. oleylamine), sulfur containing organomolybdenum dithiocarbamates, sulfur-phosphorus containing organomolybdenum dithiophosphates, sulfur-nitrogen containing organomolybdenum compounds based on dispersants, molybdenum carboxylate salts, molybdenum-amine complexes, molybdenum amine/alcohol/amid complexes and molybdenum cluster compounds, TeflonTM and molybdenum disulfide.
  • natural esters of fatty acids such as glycerol monooleate
  • amides amides
  • imides and amines i.e. oleylamine
  • sulfur containing organomolybdenum dithiocarbamates sulfur-phosphorus containing organomolybdenum dithio
  • certain additives that are aggressive towards lead are antioxidants, antiwear additives, detergents, copper passivators and friction modifiers.
  • certain additives that are aggressive towards lead are sulfur-containing antioxidants, sulfur-containing antiwear additives and sulfur-containing copper passivators; and vegetable oil-derived friction modifiers.
  • the sulfur-containing antioxidants aggressive towards lead are phenothiazine antioxidants.
  • component (c) are added in the customary amounts in each case in the range from about 0.01 to about 10.0% by weight, based on the engine oil composition.
  • the compounds of the formula (I) can be introduced into the engine oil in manners known per se.
  • the compounds are readily soluble in oils. It is also possible to prepare a so-called additive masterbatch (package) that can be diluted with the corresponding fluid to use concentrations at the rate at which they are required.
  • the compounds of formula (I) may be introduced as part of an additive package.
  • the engine oils comprising components (a) and (c) do not meet or only come close to meeting the lead corrosion specification defined in ASTM D 4485 as measured by ASTM D 6594. That is, the engine oils comprising components (a) and (c), in the absence of the present compounds of formula (I), have in excess of about 100 ppm, about 120 ppm, about 150 ppm, about 180 ppm, or about 210 ppm as measured by ASTM D 6594.
  • the invention also relates to a method of preventing corrosion of lead parts that are in the presence of an engine oil composition
  • an engine oil composition comprising
  • At least one oil additive that is aggressive towards lead which is selected from the group consisting of antioxidants, antiwear additives, dispersants, detergents, antifoam additives, viscosity index improvers, copper passivators, rust inhibitors, pourpoint depressants, demulsifiers and friction modifiers,
  • a fully formulated, non-corrosive engine oil is used as the base formulation for this example.
  • a friction modifier/corrosion inhibitor GMO
  • a sulfur-containing anti wear/extreme pressure additive diternonyltrisulfide (TPS® 27)
  • TPS® 27 diternonyltrisulfide

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  • Oil, Petroleum & Natural Gas (AREA)
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  • Lubricants (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
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WO2017030785A1 (en) 2015-08-14 2017-02-23 Vanderbilt Chemicals, Llc Additive for lubricant compositions comprising an organomolybdenum compound, and a derivatized triazole
US9994531B2 (en) 2015-08-14 2018-06-12 Vanderbilt Chemicals, Llc Antioxidant compositions and lubricating compositions containing the same
EP3334810A4 (en) * 2015-08-14 2018-06-20 Vanderbilt Chemicals, LLC Additive for lubricant compositions comprising a sulfur-containing and a sulfur-free organomolybdenum compound, and a triazole
RU2680133C1 (ru) * 2015-08-14 2019-02-18 ВАНДЕРБИЛТ КЕМИКАЛЗ, ЭлЭлСи Улучшенные антиоксидантные композиции и содержащие их смазочные композиции
US10280381B2 (en) 2015-08-14 2019-05-07 Vanderbilt Chemicals, Llc Additive for lubricant compositions comprising an organomolybdenum compound, and a derivatized triazole
RU2724054C2 (ru) * 2015-08-14 2020-06-19 ВАНДЕРБИЛТ КЕМИКАЛЗ, ЭлЭлСи Присадка для композиций смазочных материалов, содержащая серосодержащее и не содержащее серы органическое соединение молибдена и триазол
US12203045B2 (en) 2020-11-17 2025-01-21 Songwon Industrial Co., Ltd. Compositions comprising alkylated diphenylamines with improved properties

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CN1675341A (zh) 2005-09-28
CA2494639A1 (en) 2004-02-19
KR20050032104A (ko) 2005-04-06
TW200413518A (en) 2004-08-01
EP1532232A1 (en) 2005-05-25
BR0313248A (pt) 2005-07-12
WO2004015043A1 (en) 2004-02-19
AU2003253351A1 (en) 2004-02-25
JP2005534782A (ja) 2005-11-17

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