US3296134A - Mineral lubricating oil containing bisphenol, detergent and phosphite additive - Google Patents

Mineral lubricating oil containing bisphenol, detergent and phosphite additive Download PDF

Info

Publication number
US3296134A
US3296134A US363976A US36397664A US3296134A US 3296134 A US3296134 A US 3296134A US 363976 A US363976 A US 363976A US 36397664 A US36397664 A US 36397664A US 3296134 A US3296134 A US 3296134A
Authority
US
United States
Prior art keywords
lubricating oil
mineral lubricating
bis
detergent
hydroxyphenyl
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
US363976A
Other languages
English (en)
Inventor
Lee Duk Hi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell USA Inc
Original Assignee
Shell Oil Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US363976A priority Critical patent/US3296134A/en
Priority to NL6505404A priority patent/NL6505404A/xx
Priority to FR14984A priority patent/FR1440192A/fr
Application granted granted Critical
Publication of US3296134A publication Critical patent/US3296134A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2209/082—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 monocarboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • 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
    • C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/12—Partial amides of polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
    • C10M2217/023—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group the amino group containing an ester bond
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/043—Mannich bases
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • This invention relates to new and improved mineral lubricating oil compositions containing ashless polymeric detergents.
  • Y- is a methylene radical or sulfur
  • X is a halogen, preferably a middle halogen (C1 or Br)
  • R is a tertiary alkyl radical of from 48 carbon atoms
  • m is an integer of 1-3, preferably 2
  • n is an integer of zero or 1
  • B an organic phosphite having the formula where Z is oxygen and/r sulfur
  • R is an aryl or alkaryl radical having 6-18, preferably 6-12 carbon atoms and the 'sum of x and y is 3 and such that x is at least 2 and y can be zero or 1 and preferably such that x is 3 and y is zero.
  • the alkylated bisphenols represented by Formula I include alkylated bisphenol sulfides such as bis(2,5-dipentyl- 4 hydroxyphenyl) sulfide, bis(2,5 dihexyl 3 hydroxypwhenyDsulfide, bis(2 methyl 5 tertiary butyl- 4-hydroxyphenyl)sulfide, bis(Z-methyl-S-tertiarybutyl-6- hydroxyphenyl)sulfide and particularly bis(3-tertiarybutyl- S-methyl-Z-hydroxyphenyl) sulfide.
  • alkylated bisphenol sulfides such as bis(2,5-dipentyl- 4 hydroxyphenyl) sulfide, bis(2,5 dihexyl 3 hydroxypwhenyDsulfide, bis(2 methyl 5 tertiary butyl- 4-hydroxyphenyl)sulfide, bis(Z-methyl-S-tertiarybutyl
  • the alkylated bisphenols having a methylene bridge include bis(2,3-di-tertiarybutyl-4-hydroxyphenyl)methane, bis(2,S-di-tertiarybutyl-4-hydroxyphenyl)methane, bis(2,- G-di-tertiarybutyl-4-hydroxyphenyl)-methane, bis(3,5-ditertiaryoctyl 4 hydroxyphenyl)methane, bis(3 tertiarybutyl 5 tertiaryoctyl 4 hydroxyephenynmethane,
  • organic phosphites of Formula II and preferably phosphites having the formula P(OR") (Ha)
  • the oil-soluble polymeric detergents which are present 7 in mineral lubricating oils of the present invention and whose detergent life is improved and increased include oxygenor oxygen and nitrogencontaining polymeric detergents.
  • the nitrogen-containing polymeric detergents are copolymers of monomers having polymerized linkages and containing nitrogen-containing groups which may be amino or amido groups. They may be derived from polymerizable monomers containing primary, secondary or tertiary (the latter two are preferred) amino nitrogen, including heterocyclic amino or amido nitrogen-containing substances, having an ethylenically unsaturated polymerizable group.
  • These detergent polymers may be obtained by polymerizing vinyl substituted heterocyclic nitrogen-containing substances such as vinyl pyridine, vinyl picoline and vinyl quinoline, vinyl pyrrolidone or vinyl v arylamines, such as paraaminostyrene, or polyamines prepared by reacting polymeric epoxy compounds with ammonia or primary or secondary amines, with polymeriz able unsaturated alcohols, acids or esters, such as acrylates and methacrylates of long chain fatty acids,- and the like.
  • vinyl substituted heterocyclic nitrogen-containing substances such as vinyl pyridine, vinyl picoline and vinyl quinoline, vinyl pyrrolidone or vinyl v arylamines, such as paraaminostyrene
  • polyamines prepared by reacting polymeric epoxy compounds with ammonia or primary or secondary amines, with polymeriz able unsaturated alcohols, acids or esters, such as acrylates and methacrylates of long chain fatty acids,- and the like.
  • pounds are those containing-tertiary amine groups and particularly those containing heterocyclic amino groups such as obtained by copolymerizing a polymerizable heterocyclic nitrogen base compound with a polymerizable unsaturated material free of heterocyclic nitrogen-containing radicals such as are described in British patent specification 760,554 and US. Patents 2,839,512 and 2,889,282.
  • the copolymers include: (A) copolymer of stearyl methacrylate, and Z-methyl-S-vinyl pyridine; (B) copolymer of stearyl methacrylate, lauryl methacrylate and 2-methyl-5-vinyl pyridine; and those which contain additional C alkyl methacrylates in the polymer, such as (C) copolymers of stearyl met-hacrylate, lauryl methacrylate, methyl methacrylate and Z-methyl-S-vinyl pyridine; and similar copolymers in which the methyl methac- '1lhe preferred polymeric amino or aimido com- W lauryl methacrylate and diethylaminoethylmethacry-late.
  • Particularly preferred detergent polymers are Acryloid 917 and 966 (copolymers of N-vinyl pyrrolidone and lauryl methacrylate in the molecular weight range of 4,000 to 1,000,000) or the copolymers of vinyl pyridine and mixtures of dissimilar methacrylate esters, such as copolymers (B) or (C) prepared by the methods described in US. patents mentioned above and having molecular weight in the range of 450,000 and 850,000 as determined by the light scattering method.
  • the oxygen-containing detergents include copolymers of C alkyl acrylates and w-hydroxy alkyl methacrylates, e.g., (F) copolymer of stearyl methacrylate, lauryl methacrylate and Z-hyd-roxyethyl methacrylate.
  • suitable copolymers are those described in US. Patents 2,800,453 and 3,033,828. These polymers are present in the oil in amounts ranging from about 1% to about 10%, preferably fromabout 1.5% to about 5% by weight.
  • the mineral lubricating oil base may be derived from a variety of petroleum base stocks and are preferably paraflinic and/or naphthenic in character; they may also contain substantial proportions of hydrocarbons having aromatic character.
  • the viscosity may vary within wide limits so that the oils may belong, for example, to SAE classes 5W, W, 20W, 20, 30, 40, 50, 60, or 70.
  • Suitable oils may be derived from highly pa-rafiinic crudes in which case distillation and/ or dewaxing may besuflicient to provide -a suitable base stock; chemical or selective solvent treatment may be used if desired, but is preferably kept to a minimum for economic reasons.
  • compositions of the present invention are as follows:
  • Composition (a) ran for over 100 hours at which time the engine was clean, free of sludge and corrosion and otherwise in excellent condition.
  • Composition (a) was modified by removing the tritolyl phosphite and this modified phosphorus-free composition identified as Composition (X) was used in the LS-3 test and visible sludge formation was noted at end of 40 hours and engine had to be stopped.
  • Compositions (b), (c), or (d) of the present invention were obtained with Composition (a).
  • di-tertiary-butyl 4-hyd-roxyphenyl)methane was substituted with equal amount (0.3% mole) of tritolylphosphite to form Composition (Y) and engine tested (LS-3 condition), operation of the engine had to be terminated.
  • compositions (X) and (Y) are as follows:
  • Additive mixture of the present invention can be also used to improve fuels, fuel oils, greases, asphaltsgoil.
  • a mineral lubricating oil composition comprising a major amount of'mineral lubricating oil and from about 1% to about 10% of a copolymer of Z-hydroxyethyl methacrylate and a mixture of lauryl and stearyl meth acrylates and from about 0.01% to about 2% each'of- (A) an alkylated bisphenol having the formula )n )n where Y is a radical selected from the group consisting of CH and -S, X is a halogen, R is a tertiary alkyl' radical of 4 to 8 carbon atoms and m and n are integers such that m is at least 1 and n can be zero and (B) an organic phosphite having the formula where Z is an element selected from the group consisting of oxygen and sulfur, R is an aryl radical and x-I-y equal 3 and y is at least 2.
  • a mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from about 1% to about 10% of a copolymer of 2-hydroxyethyl. methacrylate and a mixture of lauryl and stearyl methacrylates and from about 0.01% to about 2% eachof 5 bis(3,5-di-tertiary-butyl-4 hydroxypheuyDmethane and tritolyl phosphite.
  • a mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from about 1% to about 10% of a copolymer of Z-hydroxyethyl methacrylate and a mixture of lauryl and stearyl methacrylates and from about 0.01% to about 2% each of bis(3,5-di-tertiarybutyl 4-hydroxyphenyl)methane and ditolyl phosphite.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US363976A 1964-04-30 1964-04-30 Mineral lubricating oil containing bisphenol, detergent and phosphite additive Expired - Lifetime US3296134A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US363976A US3296134A (en) 1964-04-30 1964-04-30 Mineral lubricating oil containing bisphenol, detergent and phosphite additive
NL6505404A NL6505404A (enrdf_load_stackoverflow) 1964-04-30 1965-04-28
FR14984A FR1440192A (fr) 1964-04-30 1965-04-28 Perfectionnements au graissage

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US363976A US3296134A (en) 1964-04-30 1964-04-30 Mineral lubricating oil containing bisphenol, detergent and phosphite additive

Publications (1)

Publication Number Publication Date
US3296134A true US3296134A (en) 1967-01-03

Family

ID=23432522

Family Applications (1)

Application Number Title Priority Date Filing Date
US363976A Expired - Lifetime US3296134A (en) 1964-04-30 1964-04-30 Mineral lubricating oil containing bisphenol, detergent and phosphite additive

Country Status (2)

Country Link
US (1) US3296134A (enrdf_load_stackoverflow)
NL (1) NL6505404A (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3547821A (en) * 1967-11-13 1970-12-15 Texaco Inc Hydrocarbon lubricating oil containing a polymer of a conjugated diolefin as a viscosity index improver
US3903002A (en) * 1973-10-09 1975-09-02 Chevron Res Lubricant

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2188943A (en) * 1935-12-28 1940-02-06 Socony Vacuum Oil Co Inc Lubricant and method of producing same
US2758091A (en) * 1947-10-28 1956-08-07 Shell Dev Lubricating compositions
GB845255A (en) * 1958-09-22 1960-08-17 Shell Res Ltd Lubricating oils
FR1299534A (fr) * 1961-04-11 1962-07-27 Ethyl Corp Nouveaux additifs à action anti-oxydante pour les compositions organiques telles que les carburants, les lubrifiants et les polymères hydrocarburés
US3100749A (en) * 1960-05-16 1963-08-13 Shell Oil Co Lubricating compositions
US3115465A (en) * 1960-04-11 1963-12-24 Ethyl Corp Stabilized compositions of matter
US3215631A (en) * 1963-02-08 1965-11-02 Shell Oil Co Lubricants containing ashless nitrogencontaining polymeric detergents and complexes of acid aryl phosphates

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2188943A (en) * 1935-12-28 1940-02-06 Socony Vacuum Oil Co Inc Lubricant and method of producing same
US2758091A (en) * 1947-10-28 1956-08-07 Shell Dev Lubricating compositions
GB845255A (en) * 1958-09-22 1960-08-17 Shell Res Ltd Lubricating oils
US3115465A (en) * 1960-04-11 1963-12-24 Ethyl Corp Stabilized compositions of matter
US3100749A (en) * 1960-05-16 1963-08-13 Shell Oil Co Lubricating compositions
FR1299534A (fr) * 1961-04-11 1962-07-27 Ethyl Corp Nouveaux additifs à action anti-oxydante pour les compositions organiques telles que les carburants, les lubrifiants et les polymères hydrocarburés
US3215631A (en) * 1963-02-08 1965-11-02 Shell Oil Co Lubricants containing ashless nitrogencontaining polymeric detergents and complexes of acid aryl phosphates

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3547821A (en) * 1967-11-13 1970-12-15 Texaco Inc Hydrocarbon lubricating oil containing a polymer of a conjugated diolefin as a viscosity index improver
US3903002A (en) * 1973-10-09 1975-09-02 Chevron Res Lubricant

Also Published As

Publication number Publication date
NL6505404A (enrdf_load_stackoverflow) 1965-11-01

Similar Documents

Publication Publication Date Title
US2889282A (en) Lubricating oil compositions
US4094799A (en) Solid particles-containing lubricating oil composition and method for using same
US3189544A (en) Non-ash-containing lubricating oil composition
US3198736A (en) Lubricating composition
US3116249A (en) Lubricating oil compositions
US3116248A (en) Lubricating oil composition
US3979308A (en) Lubricant compositions with improved viscosity index
US3296134A (en) Mineral lubricating oil containing bisphenol, detergent and phosphite additive
US3265618A (en) Lubricating oil compositions
US3357920A (en) Non-ash containing lubricating oil compositions
US3282839A (en) Mineral lubricating oil compositions
US3198739A (en) Lubricants and polymeric additives therefor
US3285854A (en) Lubricating oil composition
US3309317A (en) Lubricating composition
US3102863A (en) Lubricating compositions
US3380928A (en) Lubricating oil composition
US3475393A (en) Nitrogen-containing oil-soluble polymeric detergents
US3179591A (en) Lubricating compositions
US3462367A (en) Lubricating oils containing an antioxidant mixture of zinc and antimony dialkyl dithiocarbamates
US3268494A (en) Lubricating compositions
US2822332A (en) Lubricating oil additive and method of preparing the same
US2524563A (en) Lubricant
US3265673A (en) Copolymers of long-chained acrylic esters with sulfur containing acrylates
US3100749A (en) Lubricating compositions
US3100748A (en) Lubricating compositions