EP0815187B1 - Compositions de lubrifiant et de carburant contenant du sulfure de diphenyle portant des substituants organiques - Google Patents

Compositions de lubrifiant et de carburant contenant du sulfure de diphenyle portant des substituants organiques Download PDF

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Publication number
EP0815187B1
EP0815187B1 EP96905480A EP96905480A EP0815187B1 EP 0815187 B1 EP0815187 B1 EP 0815187B1 EP 96905480 A EP96905480 A EP 96905480A EP 96905480 A EP96905480 A EP 96905480A EP 0815187 B1 EP0815187 B1 EP 0815187B1
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EP
European Patent Office
Prior art keywords
composition
substituted
carbon atoms
formula
dithiophosphate
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EP96905480A
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German (de)
English (en)
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EP0815187A1 (fr
EP0815187A4 (fr
Inventor
Andrew Gene Horodysky
Ross Allan Kremer
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ExxonMobil Oil Corp
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ExxonMobil Oil Corp
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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
    • 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
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02—Petroleum 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/72—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing sulfur, selenium or tellurium
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
    • C10M129/95—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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/56—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/20—Thiols; Sulfides; Polysulfides
    • C10M135/28—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
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    • 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
    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • 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
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions used as base material
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
    • C10M2203/1045—Aromatic fractions used as base material
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    • 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
    • C10M2203/1065—Naphthenic fractions used as base material
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • C10M2203/1085—Residual fractions, e.g. bright stocks used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • 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
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    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • 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
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    • 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
    • C10M2219/003—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/021—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • 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
    • C10M2219/0406—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides used as base material
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbasedsulfonic acid salts
    • C10M2219/0463—Overbasedsulfonic acid salts used as base material
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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
    • C10M2219/061—Thio-acids; Thiocyanates; Derivatives thereof used as base material
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    • 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
    • C10M2219/081—Thiols; Sulfides; Polysulfides; Mercaptals used as base material
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    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/101—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring used as base material
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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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    • 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

Definitions

  • This invention relates to fuel and lubricant compositions which are based on specific substituted diphenyl sulfides in combination with succinimide and dithiophosphate additives.
  • the lubricant compositions use substantially monoalkyl ring-substituted diphenyl sulfides as basestocks which achieve particularly good performance, especially improved antiwear and extreme pressure properties, when combined with the specified additives.
  • Alkyldiarylsulfide high temperature lubricants dithiophosphate (or phosphorodithioate) antiwear agents, and polymer-substituted succinic acid derivative ashless detergents are each known in the art individually as components of lubricant compositions.
  • U.S. Patent Nos. 3,172,892 and 3,272,746 disclose polymer-substituted succinamides and succinimides which are useful in lubricant compositions and are prepared by reacting a polymer-substituted succinic acid or succinic anhydride with an alkylene polyamine.
  • U.S. Patent No. 3,194,812 teaches the use of high molecular alkenyl-n-para-aminophenyl succinimide as a dispersing agent in lubricants.
  • U.S. Patent No. 3,216,936 discloses lubricant additives which are predominantly amides and imides prepared by reacting an alkylene amine with a polymer-substituted succinic acid or anhydride and an aliphatic hydrocarbon monocarboxylic acid. The compounds are adapted for use with metal phosphorodithioates.
  • U.S. Patent No. 3,691,220 describes diorganophosphoro- dithioates prepared from the corresponding acid and a basic zinc compound in the presence of isopropyl alcohol, which are used as additives for lubricating oils.
  • U.S. Patent No. 3,804,763 discloses dispersant compositions useful as additives for lubricating oils, prepared by reacting a carboxylic acylating agent having at least 30 carbon atoms, e.g., a polymer-substituted succinic acid, anhydride or ester, with a hydroxy compound, a polyoxyalkylene polyamine, and an alkylene amine.
  • a carboxylic acylating agent having at least 30 carbon atoms, e.g., a polymer-substituted succinic acid, anhydride or ester, with a hydroxy compound, a polyoxyalkylene polyamine, and an alkylene amine.
  • U.S. Patent No. 4,153,564 teaches compounds that act as emulsifiers, detergents, and antioxidants for lubricating compositions, prepared by reacting an alkenylsuccinic anhydride acid with an aromatic amine-aldehyde resin.
  • U.S. Patent No. 4,234,435 describes lubricant additives which are prepared by reacting an acylating agent derived from a polyalkene and a dibasic carboxylic such as maleic acid or derivative, with a polyethylene polyamine, and in which the polyalkene has a number average molecular weight (M n ) of 1300 to 5000 and a ratio of weight average to number average molecular weight (M w /M n ) of 1.5 to 4.
  • U.S. Patent No. 4,255,271 shows phosphorodithioate additives for reducing friction and wear when added to a lubricant, prepared by reacting a phosphosulfurized hydrocarbyl oxazoline with a nitrogen containing compound and an olefin.
  • U.S. Patent No. 4,522,736 discloses products having utility as a dispersant and/or anticorrosion agent when used in a lubricant, which are prepared by reacting a polyalkenylsuccinic compound with an aromatic secondary amine or hindered phenol containing a hydroxyalkyl group, followed by reaction with an alkanolamine or an aminomethane.
  • U.S. Patent No. 4,652,387 teaches borated reaction products of an alkenyl succinic compound, an aryl amine and an aminoalcohol which are described as highly effective dispersant and antioxidant/anticorrosion additives for lubricant compositions.
  • U.S. Patent No. 4,840,744 describes polyamino alkenyl or alkyl succinimides containing carbamate functionalities, which are useful as dispersants in lubricating oils.
  • U.S. Patent No. 4,895,579 discloses products providing dispersant and antioxidant activity to lubricant compositions, which are prepared by reacting an alkenylsuccinic compound with an arylamine and a hindered alcohol.
  • U.S. Patent No. 5,171,915 teaches the alkylation of any of a wide variety of aromatic compounds, including diphenylsulfide, using as an alkylating agent a monoolefinic dimer of an olefin obtained as a by-product in the production of high viscosity index polyalphaolefins (HVI-PAO).
  • HVI-PAO high viscosity index polyalphaolefins
  • the alkylation reaction is carried out in the presence of a Friedel-Crafts compound or zeolite as an alkylation catalyst.
  • the alkylated aromatic compounds are stated to be useful as lubricant additives imparting antioxidant and antiwear properties.
  • British Patent No. 1,093,945 discloses alkyldiarylsulfides useful as high temperature functional fluids such as lubricants.
  • US 5,344,578 discloses alkyl ethers of sulfur-containing hydroxyl-derived aromatics for use as high-performance synthetic lubricant base stocks with superior catalytic thermal/oxidative stabilities, anti-wear and load-carrying properties.
  • US 4,161,451 discloses a lubricating oil additive composition having improved oxidation properties.
  • the composition comprises antioxidents including aromatic sulfides.
  • compositions suitable for use in lubricants and fuels comprising 1) a substantially moalkyl ring-substituted diphenyl sulfide; 2) a succinic dispersant component; and 3) a dithiophosphate, also known as a phosphorodithioate.
  • the succinic dispersant is a polymer-substituted succinic acid derivative, that is, a polymer-substituted succinimide, succinamide, or succinic acid ester in which the alcohol or phenol moiety of the ester group may optionally contain amide, imide or amine nitrogen functionality, or mixtures of the amide, imide and/or ester.
  • Lubricant compositions comprising the foregoing three components, preferably using the alkylated diphenyl sufides as the lubricant basestock, have unexpectedly good antiwear and extreme pressure properties as well as other desirable properties such as those of corrosion resistance and high temperature cleanliness.
  • the substantially monoalkyl groups in the ring substituted diphenyl sulfide are substituted for the hydrogen atoms bonded to ring carbon atoms.
  • Such alkyl groups may be cyclic, linear or branched.
  • one or more hydrogen and/or carbon atoms in such groups may be substituted with S, N, O, P and/or F.
  • the monoalkyl-substituted diphenyl sulfide may contain, for example, 1 to 8, preferably 1 to 2 ring-substituted organo groups, with each substituent organo group containing in the range, for example, of 1 to 500, preferably 5 to 50, and most preferably 10 to 30 carbon atoms.
  • the preferred diphenyl sulfides are the monoalkylated diphenyl sulfides in which the alkyl group is linear and contains from 5 to 40 carbon atoms.
  • the substituted diphenyl sulfide is preferably a monoalkyldiphenyl sulfide in which the alkyl group contains from 10 to 20 carbon atoms.
  • the substantially monoalkyl ring-substituted diphenyl sulfide is generally prepared by reacting diphenyl sulfide in the presence of an alkylation catalyst with an organic substitution reactant having the same structure as the organo group to be substituted except that it contains a preferably terminal double-bonded carbon atom which becomes bonded to a ring carbon atom of the diphenyl sulfide.
  • an n-alkyldiphenyl sulfide the diphenyl sulfide is reacted with an alpha-olefin containing the same number of carbon atoms as the n-alkyl substituent.
  • the molar ratio of organic substitution reactant to diphenyl sulfide varies from 0.5:1.0 to 10.0:1.0 and preferably from 1.0:1.0 to 4.0:1.0.
  • the alkylation catalyst used to prepared the organo-substituted diphenyl sulfide may be, for example, a Friedel-Crafts catalyst such as aluminum trichloride or boron trifluoride.
  • a Friedel-Crafts catalyst such as aluminum trichloride or boron trifluoride.
  • the reaction is carried out in the presence of a zeolite catalyst, to obtain a substantially mono-substituted diphenyl sulfide.
  • Such zeolite catalyst should be at least partly in the acidic (H) form to confer the acidity for the reaction but may contain other cations also such as ammonium (NH 4 +), and is preferably a large pore zeolite such as a faujasite, e.g., zeolite X, Y, USY, UHP-Y, ZSM-20 or zeolite beta.
  • zeolite MCM-22 U.S. Patent Nos. 4,954,325; 5,100,534 and 5,103,066).
  • the reaction is normally effected at temperatures ranging from ambient to 350°C, preferably from 100-250°C and most preferably from 180-240°C.
  • the reaction can be performed, for example, in a batch or semi-batch mode by continuous or partial addition of catalyst or organic substitution reactant to the diphenyl sulfide.
  • Catalyst can be used at levels ranging from 1 gram/mole of aromatic to 100 grams/mole of aromatic, preferably from 5 gram/mole of aromatic to 50 grams/mole of aromatic, and most preferably from 10-30 grams catalyst/mole of aromatic.
  • the catalyst may be steamed, calcined or fresh.
  • the monoalkyldiphenyl sulfides obtained with the zeolite catalysts, exhibit superior properties in comparison to the organo-substituted diphenyl sulfides prepared by reaction of the organic substitution reactant, e.g. alpha-olefin, with the diphenyl sulfide in the presence of AlCl 3 and other proton, and Lewis acids.
  • the organic substitution reactant e.g. alpha-olefin
  • the monoalkyl-substituted diphenyl sulfides obtained with zeolite alkylation catalysts are substantially, i.e., up to 100% and at least 95-98% mono-substituted, e.g., monoalkylated, which can be demonstrated by gas chromatographic methods.
  • the monoalkyl-substituted diphenyl sulfide may be used as the main base stock oil in lubricant or as the main component of a fuel composition or in combination with other synthetic and/or mineral oil fluids. In either case, it will generally have a viscosity in the range, for example, of 2 to 1000 cSt (2 - 1000 x 10 -5 m 2 /s), preferably 3 to 100 cSt (3 - 100 x 10 -5 m 2 /s), and more preferably 3 to 30 cSt (3 - 30 x 10 -5 m 2 /s), at 100°C, and be present in the composition in the range, for example, of 0.5 to 95 wt.% or more, preferably 2 to 90 wt.%, with concentrations of 2 to 20 wt.% being preferred in some applications, particularly when another base stock oil is used with the substituted diphenyl sulfide, and 25 to 90 wt.% in the other applications.
  • the compounds making up the dispersant component singly or in combination, viz., a polymer substituted succinic acid derivative which is the 1) succinimide; 2) succinamide; or 3) succinic acid ester in which the alcohol or phenol moiety of the ester group may optionally contain amide, imide or amine nitrogen functionality, are very complex mixtures of condensation reaction products of the respective reactant.
  • R is the residue of a homopolymer or copolymer of ethylenically unsaturated monomers, e.g., an alkyl or alkenyl group which is the residue of a polyalkene in which the alkene contains, for example, 2 to 20 carbon atoms and R has at least 20, preferably at least 50, and up to 300 or more carbon atoms, and has a number average molecular weight (M n ) of, for example, 300 to 10,000, preferably 500 to 2,000;
  • Z is (separately in formula 2) hydrogen or an aliphatic or aromatic organic radical containing carbon, hydrogen and optionally nitrogen and/or oxygen and/or is the residue of an amino compound which is reacted with a polymer-substituted succinic acid derivative acylating agent, and
  • Y is an aliphatic or aromatic radical containing carbon, hydrogen, nitrogen and optionally oxygen and/or is the residue of an alcohol
  • the dispersant is prepared, for example, by reacting maleic anhydride or acid with a suitable polymer, e.g., of an alkene containing, for example 2 to 20 carbon atoms, which contains a double bond or a halogen atom, e.g., chlorine, to obtain a polymer substituted succinic acid or anhydride acylating agent.
  • a suitable polymer e.g., of an alkene containing, for example 2 to 20 carbon atoms, which contains a double bond or a halogen atom, e.g., chlorine
  • an appropriate hydrocarbyl substituted amine or an alcohol or phenol which may optionally contain amide, imide or amine nitrogen functionality, to obtain the desired dispersant.
  • suitable dispersants are polymer-substituted succinamides and succinimides and disclosed in US Patents Nos.
  • Z in the imides and at least one Z in the amides may be the residue attached to a reactive nitrogen atom of any of a wide variety of polyoxyalkylene polyamines and alkylene polyamines
  • Y in the ester may be the residue attached to a hydroxy group of any of a wide variety of nitrogen-containing and non-nitrogen containing hydroxy compounds, e.g., monohydric and polyhydric alcohols and phenols, polyalkylene glycols, monoesters of polyhydric compounds, aminoalcohols, aminophenols, etc.; polymer substituted succinimides as disclosed in US Patent No.
  • the polymer substituent R is derived from any of a large group of homopolymers and copolymers of a wide variety ethylenically unsaturated monomers, preferably hydrocarbon monomers, which have a number average molecular weight (M n ) of 1300 to 5000 and a ratio of weight average molecular weight (M w ) to M n of from 1.5 to 4, and Z in the imides and at least one Z in the amides is the residue attached to a reactive nitrogen atom of an alkylene polyamine such as those disclosed in several of the other patents cited in this paragraph; polymer-substituted succinamides, succinimides, or succinic acid esters as disclosed in US Patent No.
  • the polymer substituted succinic acid derived dispersant may be present in the composition in an amount, for example, of 0.1 to 25 wt.%, preferably 0.15 to 10 wt.%, and most preferably 1 to 7 wt.% based on the weight of the composition.
  • the dithiophosphate component of the compositions of this invention is in most cases derived from an organodithiophosphoric acid having the formula in which R 1 and R 2 are separate hydrocarbyl radicals or together form with the phosphorus and oxygen atoms monomeric ring structures or polymeric chain structures.
  • the dithiophosphate is a metal salt of a dihydrocarbyl dithiophosphoric acid where the metal is a member of Group II of the Periodic table, particularly zinc and barium and preferably zinc.
  • Ashless dithiophosphates may also be used, e.g., reaction products of an alkylene oxide, an amine or an olefin with an organodithiophosphoric acid as is well-known in the art.
  • the R 1 and R 2 groups may be the same or different and are selected from the group consisting of alkyl, cycloalkyl, aryl, alkaryl and aralkyl radicals, the radicals having from 3 to 30 carbon atoms.
  • R 1 and R 2 groups may be exemplified by n-propyl, iso-propyl, n-butyl, iso-butyl, amyl, hexyl, decyl, dodecyl, octadecyl, eicosyl, pentacosyl, benzyl, phenethyl, cyclohexyl, phenyl, naphthyl, tolyl, t-amylphenyl, didodecylphenyl, wax phenyl, where the wax portion contains 24 carbon atoms, and the like.
  • neoalkyl radicals such as 2,2-dimethyl-1-propyl, 2,2,4-trimethyl-1-butyl, 2,2-dimethyl-1-decyl and 2,2,4-trimethyl-1-hexadecyl, may be used.
  • acids which can be used and in which R 1 and R 2 are the same are the dipropyl, dibutyl, dihexyl, didodecyl, dioctadecyl, dicyclohexyl, dibenzyl, diphenethyl, diphenyl, ditolyl, didodecylphenyl, diwaxphenyl, di(2,2-dimethyl-1-propyl), di(2,2,4-trimethyl-1-butyl), di(2,2-dimethyl-1-decyl) and di(2,2-4-trimethyl-1-hexadecyl) dithiophosphoric acid.
  • Useful acids in which R 1 and R 2 are different are illustrated by the following: n-propyl amyl, amyl decyl, hexyl dodecyl, decyl cyclohexyl, benzyl phenyl and the like dithiophosphoric acids.
  • R 1 and R 2 are alkyl groups containing 1 to 50 carbon atoms, more preferably 3 to 20 carbon atoms.
  • dithiophosphates are known, as shown, for example in US Patents Nos. 3,216,936 and 3,691,220.
  • dithiophosphoric acids in which R 1 and R 2 together define a monomeric ring structure or a polymeric chain structure are those containing one or more oxazoline groups as shown in U.S. Patent No. 4,255,271.
  • the dithiophosphate component may be present in the composition in an amount, for example, 0.05 to 10 wt.%, preferably 0.1 to 5 wt.%, and most preferably 0.2 to 3 wt.% based on the weight of the composition.
  • compositions of this invention may be combined or blended with other synthetic oils and/or mineral oils and particularly with synthetic polyalphaolefins (PAO).
  • PAO synthetic polyalphaolefins
  • Any suitable blending ratio of substituted diphenylsulfide to other synthetic oil and/or mineral oil may be used; for example, a base stock blend of 20 wt.% of substituted diphenylsulfide and 80 wt.% PAO has been found to be very advantageous.
  • the monoalkyl ring-substituted diphenylsulfide may constitute a major proportion of the base stock oil up to 100%.
  • mineral oils both paraffinic, naphthenic and mixtures thereof, employed as part of base stock oil in the lubricant, or grease vehicle, may be of any suitable lubricating viscosity range, as for example, from 1.0 cSt (1 x 10 -5 m 2 /s) at 100°C to 1000 cSt (1 x 10 -2 m 2 /s) at 100°C and preferably, from 2.0 to 60 cSt (2 - 60 x 10 -5 m 2 /s at 100°C.
  • the preferred oils may have viscosity indexes ranging to 150.
  • the average molecular weights of these oils may range from 250 to 800.
  • Suitable synthetic oils include polyalphaolefins, e.g., polyisobutylene, polybutenes, or hydrogenated polydecenes, polypropylene glycol, polyethylene glycol, trimethylpropane esters, neopentyl e.g. pentaerythritol, esters, di(2-ethylhexyl) sebacate, di(2-ethylhexyl) adipate, dibutyl phthalate, fluorocarbons, silicate esters and esters of phosphorus-containing acids and alkylsubstituted diphenyl ethers.
  • polyalphaolefins e.g., polyisobutylene, polybutenes, or hydrogenated polydecenes
  • polypropylene glycol polyethylene glycol
  • trimethylpropane esters neopentyl e.g. pentaerythritol, esters, di(2-ethylhe
  • compositions of the invention may also be used in greases or in any of the foregoing synthetic and/or mineral base stock oils thickened with an appropriate thickener or gelling agents.
  • thickener or gelling agents may include any of the conventional metal salts or soaps, which are dispersed in the lubricating vehicle in grease-forming quantities in an amount to impart to the resulting grease composition the desired consistency.
  • Other thickening agents that may be employed in the grease formulation may comprise the non-soap thickeners, such as surface-modified clays and silicas, aryl ureas, calcium complexes and similar materials.
  • grease thickeners may be employed which do not melt and dissolve when used at the required temperature within a particular environment; however, in all other aspects, any material which is normally employed for thickening or gelling hydrocarbon fluids for forming greases can be used in preparing greases in accordance with the present invention.
  • a mineral oil or synthetic oil base stock oil of lubricating viscosity in addition to the substituted diphenyl sulfide is utilized in the composition, it may be present in an amount, for example of 2 to 98 wt.%, preferably 5 to 90 wt.%, based on the total composition.
  • compositions of this invention may also be included, e.g., additional dispersants, metallic detergents (phenates, sulfonates, and/or salicylates), antioxidants (as exemplified by hindered phenols, arylamines, dithiocarbamates, etc.), polymeric viscosity index improvers (polyisobutylene, styrene-diene copolymers, polymethacrylates, etc.), auxiliary antiwear or extreme pressure additives (heterocyclic triazoles, dimercaptothiadiazoles, dithiocarbamates, phosphites, phosphonates, acid phosphates, thiophosphates, phosphonothionates, borates, etc.), corrosion inhibitors, emulsifiers, demulsifiers, seal swell
  • the composition of this invention can be used in demanding applications such as diesel engine oils which generate large quantities of performance-property robbing particulate soot, or in somewhat less demanding applications such as turbine, circulating, or hydraulic oils, or in thickened lubricants such as greases.
  • compositions of this invention may reside in lubricant applications, use in fuels would also provide many of the same performance advantages. Concentrations of 1 to 1,000 pounds of components per thousand barrels of fuel are preferred. Fuel compositions include hydrocarbon fuels, oxygenated fuels, and mixtures of hydrocarbon and oxygenated fuels. Use of a mixture of aromatic fluid and dispersant would be especially advantageous in fuels.
  • the examples illustrate the effect on lubrication properties of mixing a typical lubricating mineral oil with varying amounts of a substantially monoalkyl ring-substituted diphenyl sulfide.
  • substantially monoalkylated diphenyl sulfide was blended in varying amounts with a paraffinic neutral lubricating base stock mineral oil having a viscosity of 100 Saybolt seconds at 40°C and the blends, together with the pure ADPS and mineral oil were tested for their lubrication properties, using the Four Ball Wear Test described in test method ASTM D2266 and/or U.S. Patent No. 4,761,482.
  • Results are shown in Table I in terms of wear scar diameter and "K" factor which is a function of wear volumes and is a dimensionless number defined as the product of the wear volume times the metal hardness divided by the product of the distance travelled and the load.
  • the "K” factor is relatively independent of test conditions, provided effective lubrication is maintained.
  • the "K” factor allows for Hertzian diameter and permits calculations of wear rates that can be related to machine life under various operating conditions and metallurgy.
  • a fully formulated commercially obtained diesel engine oil derived from mineral oil base stocks and containing both polymer-substituted succinimide ashless dispersant and zinc dithiophosphate was run in a GM 6.2 liter diesel engine for 50 hours at 1,000 rpm with coolant and oil gallery temperatures of 120°C, a fuel flow of 9 kg/hr, and fuel and inlet air temperatures of 35°C and 32°C, respectively.
  • the absolute intake air and exhaust back pressures were 97 kPa and 10-3 kPa, respectively.
  • the wear properties of the oil significantly diminished, due in part to the combustion byproducts (soot) and aging of the lubricant.
  • Example 3 The procedure of Example 3 and Comparative Example M was repeated on a different commercially obtained mineral oil based diesel engine oil also containing a polymer-substituted succinimide dispersant and zinc dithiophosphate, except that only a single wear evaluation was obtained for the partially depleted oil containing no ADPS (Comparative Example N) and that containing 5 wt. ADPS (Example 4).
  • Example 4 Example Alkylated Diphenyl Sulfide, Wt.% Wear Scar Diameter, mm Wear K Factor Wear Ratio N 0 1.31 160 4.37 4 5 0.84 26 2.80

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Claims (13)

  1. Une composition de lubrifiant ou de carburant comprenant 1) un organo, diphenyl sulfure à noyau sensiblement mono-alkylé; 2) un composant dispersant comprenant un succinimide, succinamide et/ou ester d'acide succinique à substitution par un polymère et 3) un dithiophosphate.
  2. La composition selon la revendication 1 dans laquelle le monoalkyle diphényl sulfure contient un groupe alkyle comportant de 10 à 20 atomes de carbone.
  3. La composition selon la revendication 1 dans laquelle le résidu alcool ou phénol du groupe ester de l'ester d'acide succinique contient une fonctionnalité azotée amide, imide ou aminé.
  4. La composition selon la revendication 1 ou 2 dans laquelle le dispersant est un succinimide comprenant au moins un composé ayant la formule
    Figure 00280001
    et/ou un succinamide comprenant au moins un composant ayant la formule:
    Figure 00280002
       dans laquelle R est un groupe alkyle ou alkényle qui est le résidu d'un polyalkylène dont l'alkène contient 2 à 20 atomes de carbone et R comporte au moins 20 atomes de carbone et Z est l'hydrogène ou un radical organique aliphatique ou aromatique contenant du carbone, de l'hydrogène et le cas échéant de l'azote et/ou de l'oxygène, et/ou le résidu est fixé à un atome d'azote réactif d'un dérivé amino qui est mis en réaction avec un agent acylant de l'acide succinique à substitution par un polymère.
  5. La composition selon la revendication 4 dans laquelle Z, dans la formule 1), et/ou au moins un des Z de la formule 2) est le résidu fixé à un atome d'azote actif d'un alkylène polyamine répondant à la formule:
    Figure 00290001
       où n est un entier inférieur à 10, A est un hydrogène ou un radical hydrocarboné, et le groupe alkylène comporte moins de huit atomes de carbone.
  6. La composition selon la revendication 5 dans laquelle le dérivé amino est un alkylène polyamine répondant à la formule:
    Figure 00290002
       où n est un entier inférieur à 10, A est un hydrogène ou un radical hydrocarboné, et le groupe alkylène comporte moins de huit atomes de carbone.
  7. La composition selon une quelconque des revendications 1 à 6 dans laquelle le dithiophosphate est un sel de zinc de l'acide dithiophosporique répondant à la formule:
    Figure 00290003
       où R1 et R2 sont indépendant l'un de l'autre des groupes alkyles comportant 3 à 30 atomes de carbone.
  8. La composition selon la revendication 1 comprenant 0,5 à 95 % en poids d'organo, diphényl sulfure à noyau sensiblement monoalkylé, 0,1 à 25 % en poids du composant dispersant et 0,05 à 10 % en poids de dithiophosphate.
  9. La composition selon la revendication 8 comprenant 2 à 90 % en poids d'organo, diphényl sulfure à noyau sensiblement monoalkylé, 0,15 à 10 % en poids de composant dispersant et 0,1 à 5 % en poids de dithiophosphate.
  10. La composition selon la revendication 9 comprenant 1 à 7 % en poids de composant dispersant et 0,2 à 3 % en poids de dithiophosphate.
  11. La composition selon la revendication 1 comprenant en outre une huile minérale, une huile synthétique, ou un mélange d'huile minérale et d'huile synthétique, de viscosité lubrifiante.
  12. La composition selon la revendication 11 dans laquelle l'huile minérale, l'huile synthétique ou mélange est présent à raison de 2 à 98 % en poids.
  13. La composition selon la revendication 12 dans laquelle l'huile minérale, l'huile synthétique ou le mélange est présent à raison de 5 à 90 % en poids.
EP96905480A 1995-03-20 1996-02-14 Compositions de lubrifiant et de carburant contenant du sulfure de diphenyle portant des substituants organiques Expired - Lifetime EP0815187B1 (fr)

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US8247358B2 (en) 2008-10-03 2012-08-21 Exxonmobil Research And Engineering Company HVI-PAO bi-modal lubricant compositions

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US20070203030A1 (en) * 2006-01-13 2007-08-30 Buck William H Low sulfur, low ash and low phosphorous lubricant additive and composition
JP2010047747A (ja) * 2008-07-22 2010-03-04 Sanyo Chem Ind Ltd 潤滑油添加剤及び潤滑油組成物

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US8247358B2 (en) 2008-10-03 2012-08-21 Exxonmobil Research And Engineering Company HVI-PAO bi-modal lubricant compositions
US8476205B2 (en) 2008-10-03 2013-07-02 Exxonmobil Research And Engineering Company Chromium HVI-PAO bi-modal lubricant compositions

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