EP0351906B1 - Synthetische Schmierölzusammensetzung - Google Patents

Synthetische Schmierölzusammensetzung Download PDF

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Publication number
EP0351906B1
EP0351906B1 EP89201826A EP89201826A EP0351906B1 EP 0351906 B1 EP0351906 B1 EP 0351906B1 EP 89201826 A EP89201826 A EP 89201826A EP 89201826 A EP89201826 A EP 89201826A EP 0351906 B1 EP0351906 B1 EP 0351906B1
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EP
European Patent Office
Prior art keywords
composition
lubricant
ester
engine
present
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
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EP89201826A
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English (en)
French (fr)
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EP0351906A1 (de
Inventor
Joseph Francis Anzenberger, Sr.
Alfred Karl Jung
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Akzo NV
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Akzo NV
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    • C10M169/00Lubricating 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
    • C10M169/04Mixtures of base-materials and additives
    • C10M169/045Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution and non-macromolecular compounds
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    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
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    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
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    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108Phenothiazine
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2221/00Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/041Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving sulfurisation of macromolecular compounds, e.g. polyolefins
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/041Triaryl phosphates
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/043Ammonium or amine salts thereof
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • C10M2223/121Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2225/00Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2225/00Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
    • C10M2225/041Hydrocarbon polymers
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
    • C10N2040/251Alcohol fueled engines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
    • C10N2040/255Gasoline engines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
    • C10N2040/255Gasoline engines
    • C10N2040/28Rotary engines

Definitions

  • the present invention relates to synthetic lubricant compositions for use in high temperature rotary engines using internally lubricated fuel, wherein the lubricant is consumed and combusted during operation.
  • Alkyl trimellitate compositions suitable for use in lubricants and hydraulic fluids are described in Ger. Offen. 2,14O,683, abstracted in Chemical Abstracts, Vol 76, 115812c (1972). Of similar teaching is U.S.S.R. Patent No. 525,663, abstracted in Chemical Abstracts, Vol. 86, 92985b (1977). Blends of penta-erythritol and trimellitate esters as a synthetic lubricating oil base stock for jet engines is described in British Patent No. 1,481,27O.
  • U.S. Patent No. 3,637,5O1 describes complex esters made by reaction of a mixture of neopentyl-type polyol, an aromatic polycarboxylic acid, and an aliphatic monocarboxylic acid. It is suitable for lubricating gas turbine engines.
  • dialkyl diesters of mixtures of isophthalic acid and terephthalic acid are characterized as excellent synthetic oils in U.S. Patent No. 2,936,32O.
  • U.S. Patent No. 3,O21,357 describes novel dialkyl esters of 5-t-alkylisophthalic acid which are suitable as synthetic liquid lubricants and plasticizers for synthetic polymeric resins.
  • a gas turbine lubricant employing, as a base stock, a blend of a carboxylate ester (e.g., an ester of phthalic and/or isophthalic acid) and a low viscosity mineral oil is described in U.S. Patent No. 3,912,64O.
  • British Patent No. 1,44O,129 describes lubricants containing 85-96% triisodecyl trimellitate as a base fluid. Tricresyl phosphate is used in the lubricant of Example 2. In its two exemplified lubricants, inorganic, metal-containing additives are also used. The use of such metal-containing additives would give rise to an undesired ash residue when used under high temperature conditions, e.g., those existing in gas-fired rotary engines, above the decomposition temperature of the lubricant. Such residues lead to wear, deposits, and other problems. Also, the lubricant shown in Example 2 of British Patent No.
  • 1,44O,129 although containing triisodecyl trimellitate (85%) and tricresyl phosphate (1.5%), additionally contains an alkyl methacrylate copolymer as a viscosity improver.
  • an alkyl methacrylate copolymer as a viscosity improver.
  • Use of such a copolymer in a lubricant which is consumed during the ignition cycles of the engine with the fuel will also lead to undesired carbon deposits.
  • the lubricant compositions shown in British Patent No. 1,44O,129 if used in gas-fired rotary engines where the lubricant is sprayed into the combustion chamber for eventual consumption along with the fuel, will lead to residue problems (e.g., ash deposition or ash and carbon deposition).
  • the present lubricant composition is an improved lubricant for such engines, for example, which is consumed with the fuel and leaves essentially no residue in the combustion chamber. It comprises nonmetal containing constituents and is therefore an ashless product when subjected to high temperature conditions above the decomposition temperature of the lubricant. It does not contain polymeric additives in its additives package which, when incinerated, would also give rise to carbon deposits.
  • the present engine lubricant is a blend of a major amount of at least one aromatic tricarboxylic ester, a minor amount of antiwear agents comprising a phosphate ester, and a minor amount of an organic additives package, which is substantially free of metallic moieties or components and polymeric components as a result of which said organic additives package leaves no residue in the engine when the lubricant is incinerated during operation of the engine.
  • the first component for the lubricant of the present invention which is present in major or predominate amount and functions as the base lubricating fluid is at least one aromatic tricarboxylic ester.
  • a preferred triester component is a trimellitate ester component.
  • These esters are aromatic or benzene tricarboxylic acid triesters having the formula Ar[C(O)OR]3, where Ar is a phenyl ring and R is an aryl or an alkyl group, e.g., one having less than about 18 carbon atoms.
  • Preferred alkyl groups in such esters range from about 4 to about 18 carbon atoms in length. This component is present at from about 75 to about 99 percent by weight of the lubricant of the present invention.
  • Preferred triesters are triisodecyl trimellitate and tris-(2-ethylhexyl)trimellitate or their mixtures at ratios providing a desired viscosity.
  • An optional, component of the present invention which can also be present in minor amount, e.g., up to about 15 percent by weight of the lubricant, is at least one thermally and oxidatively stable phthalate ester component. This component is used to adjust the viscosity of the lubricant since the tri-carboxylic triesters tend to be viscous and might not have the desired viscosity characteristics if used without this optional phthalate ester also being present.
  • Such a component is a benzene carboxylic acid diester of the formula Ar(C(O)OR)2, where Ar is a phenyl ring and R is as defined above and is an alkyl group of less than about 18 carbon atoms, e.g., from about 4 to about 1O carbon atoms.
  • the esters that form this component can be derivatives of such benzene dicarboxylic acids as phthalic acid, isophthalic acid and terephthalic acid. Phthalate ester, where the substituents are in the ortho-position is not thermally and oxidatively stable within the purview of the present invention.
  • both of the above-mentioned types of tricarboxylic triesters and phthalate esters should be substantially fully esterified so there is no appreciable unreacted acid functionality in the ester component.
  • both are branch-chain aliphatic esters of the benzene carboxylic type with suitable branch chain groups including 2-ethylhexyl, 2-ethylbutyl, isooctyl, iso-propyl, and isodecyl.
  • branch chain groups derived from "Oxo" alcohols are also useful, as described in U.S. Patent No. 2,76O,934.
  • the second component of the present invention is a phosphate ester component at from about O.5% to about 1O% by weight.
  • This component is present as an antiwear and extreme pressure additive.
  • the phosphate ester is one containing three aryl groups in the form of aryl and/or alkaryl groups.
  • useful phosphate esters are tertiary butylphenyl/ phenylphosphate, secondary butylphenyl/phenylphosphate, and isopropylphenyl/phenylphosphate. These phosphate esters may be prepared in accordance with known alkylation and phosphorylation procedures as described, for example, in U.S. Reissue Patent No. 29,54O.
  • the second antiwear component of the present lubricant compositions preferable also comprises supplemental extreme pressure antiwear agents.
  • Suitable extreme pressure antiwear agents include oil-soluble organosulfur compounds, in particular, sulfurized hydrocarbons of desired molecular weight. These sulfur compounds may contain other groups which are beneficial and include phosphoros atoms.
  • a preferred class of organosulfur compounds is constituted by sulfurized olefins prepared by the reaction of a C3-C6 olefin or a polyolefin derived therefrom, with a sulfur-containing compound, such as sulfur, sulfur monochloride and phosphorpentasulfide.
  • Such extreme pressure additives are commercially available, frequently contained in additive packages designed for gear lubricants. Such commercial additives may directly be used in the present invention provided that no metal-containing components are present. Sulfurized and phosphorized extreme pressure agents are preferred.
  • the third essential component of the present invention is a substantially residue-free additives package which can comprise the following types of components:
  • the components used in the additives package need to be substantially free of metallic moieties or components if ash residues are to be avoided.
  • they are organic, rather than either metalloorganic or inorganic, in nature.
  • the organic additives chosen should not be polymers which, upon incineration, give rise to carbon deposits.
  • the additives package used in the instant lubricant is intended to provide oxidation stability, to enhance load carrying properties, and to prevent corrosion by chemical attack on ferrous surfaces as well as to passivate non-ferrous metals such as copper-containing alloys.
  • the useful load carrying additives include the amine salt of phosphoric and phosphonic acid derivatives. Moreover, certain phosphorus-amine compounds will also function as ashless antiwear additives in the synthetic base stocks of the instant invention. Such phosphorus-amine products will also give anti rust protection. Lubricant compositions containing the optional extreme pressure antiwear agent do not require the addition of a load carrying additive.
  • Aromatic amines have been used for many years to improve the oxidation stability of various synthetic lubricant base stocks.
  • Polyol esters of the type used in aircraft gas turbine engines have a long history of using aromatic amines, such as octylphenylnaphthylamine, phenothiazene, and phenyl- alpha -naphthylamine to enhance the oxidation stability of such fluids.
  • Triarylphosphate esters are good antiwear additives under normal loading conditions in both mineral oil-based and synthetic lubricants.
  • tert-butylphenyl/diphenyl phosphate has the added ability to also give extreme pressure protection under more severe loading conditions.
  • a lubricant composition in accordance with this invention is formed by admixture of the following ingredients:
  • the resulting composition was an amber colored liquid, having an "oily" odor, with an acid number of O.68 mg KOH/g. It had a boiling point of over 6OO°F (315°C), a specific gravity of O.98 at 6O°F (15.6°C), a flash point of over 46O°F (24O°C) and a vapor pressure of under 1.O mm Hg at 25°C. All of the ingredients mentioned above are non-metal containing thereby rendering the entire composition an ashless, high-temperature lubricant.

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

Claims (14)

  1. Maschinenschmiermittel, das einen überwiegenden Anteil an mindestens einem aromatischen Tricarbonsäureester, einen geringeren Anteil eines Phosphatester enthaltenden Antiabnützungsmittels sowie einen geringeren Anteil eines organischen Additivpakets enthält, welches im wesentlichen frei von metallischen Anteilen oder Komponenten sowie von polymeren Komponenten ist, derart, dass das organische Additivpaket bei Verbrennung des Schmiermittels in der laufenden Maschine keine Rückstände hinterlässt.
  2. Mittel nach Anspruch 1, bei welchem der Tricarbonsäureester in einem Anteil von 75 bis 99% des Gewichts des Schmiermittels vorhanden ist.
  3. Mittel nach Anspruch 1 oder 2, bei dem der Tricarbonsäureester ein Trimellithsäurester mit Alkylgruppen ist, die eine Länge von 4 bis 18 Kohlenstoffatomen haben.
  4. Mittel nach einem oder mehreren der Ansprüche 1 bis 3, in welchem das Antiabnützungsmittel in einem Anteil entsprechend 0.5 bis 10% des Gewichts des Schmiermittels vorhanden ist.
  5. Mittel nach einem oder mehreren der Ansprüche 1 bis 4, in welchem der Phosphatester drei Arylgruppen enthält.
  6. Mittel nach einem oder mehreren der Ansprüche 1 bis 5, in welchem das Antiabnützungsmittel ausserdem ein zusätzliches Extremdruck-Antiabnützungsmittel enthält.
  7. Mittel nach einem oder mehreren der Ansprüche 1 bis 6, in welchem das Extremdruck-Antiabnützungsmittel 0.25 bis 5.0% des Gewichtes des Schmiermittels ausmacht.
  8. Mittel nach einem der Ansprüche 6 oder 7, in welchem das Extremdruck-Antiabnützungsmittel ein sulfuriertes Syntheseprodukt ist.
  9. Mittel nach einem oder mehreren der Ansprüche 1 - 8, in welchem das organische Additivpaket in einem Anteil entsprechend 0.1 bis 5 % des Gewichts des Schmiermittels vorhanden ist.
  10. Mittel nach einem oder mehreren der Ansprüche 1-9, in welchem das organische Additivpaket bis 2.0% eines belastbaren Additivs, 0.015 bis 2.0% eines Korrosionsinhibitors, 0.05 bis 20% eines Antioxydationsmittels, 0.002 bis 0.50% eines Metallpassivierungsmittels und bis zu 0.20% eines Netzmittels, bezogen auf das Gewicht des Schmiermittels, enthält.
  11. Mittel nach einem oder mehreren der Ansprüche 1-10, das ausserdem einen geringen Anteil eines thermisch und oxydativ stabilen Phthalatesters enthält.
  12. Mittel nach Anspruch 11, in welchem der Phthalatester in einem Anteil von bis zu 15%, bezogen auf das Gewicht des Schmiermittels, vorhanden ist.
  13. Mittel nach Anspruch 11 oder 12, in welchem der Phthalatester aus der Gruppe der Isophthalsäureester und Terephtalsäureester gewählt ist.
  14. Verwendung eines Maschinenschmiermittels gemäss einem der Ansprüche 1 - 13 zum Schmieren von Hochtemperatur-Rotationsmaschinen durch Einspeisen des Maschinenschmiermittels zusammen mit dem Brennstoff in die Verbrennungskammer der Maschine und Verbrauch des Schmiermittels während des Betriebs der Maschine.
EP89201826A 1988-07-22 1989-07-11 Synthetische Schmierölzusammensetzung Expired - Lifetime EP0351906B1 (de)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8796192B2 (en) 2010-10-29 2014-08-05 Chevron Oronite Company Llc Natural gas engine lubricating oil compositions
US8841243B2 (en) 2010-03-31 2014-09-23 Chevron Oronite Company Llc Natural gas engine lubricating oil compositions

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6207623B1 (en) * 2000-01-14 2001-03-27 Exxonmobil Research And Engineering Company Industrial oils of enhanced resistance to oxidation
FR2946983B1 (fr) * 2009-06-23 2011-12-23 Nyco Agents anti-usure a neurotoxicite reduite
DE102011102540B4 (de) * 2011-05-26 2013-12-12 KLüBER LUBRICATION MüNCHEN KG Hochtemperaturöl

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FR1119412A (fr) * 1955-02-17 1956-06-20 Lubrifiants à haute pression, incongelables
DE2140683A1 (de) * 1970-08-14 1972-02-17 CIBA Geigy AG, Basel (Schweiz) Synthetisches Grundmaterial fur Schmiermittel und funktionell Fluide
US4111821A (en) * 1972-02-07 1978-09-05 Tenneco Chemicals, Inc. Lubricants for reciprocating compressors for oxygen-free gases
GB1440129A (en) * 1972-11-13 1976-06-23 Tenneco Chem Lubricant compositions
US3931023A (en) * 1974-07-22 1976-01-06 Fmc Corporation Triaryl phosphate ester functional fluids
DE3343816C2 (de) * 1983-12-03 1986-12-04 UK Mineralölwerke Wenzel & Weidmann GmbH, 5180 Eschweiler Schmiermittel
US4530772A (en) * 1984-02-22 1985-07-23 Stauffer Chemical Company Method of electrical contact lubrication
US4589990A (en) * 1985-06-21 1986-05-20 National Distillers And Chemical Corporation Mist lubricant compositions

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8841243B2 (en) 2010-03-31 2014-09-23 Chevron Oronite Company Llc Natural gas engine lubricating oil compositions
US8796192B2 (en) 2010-10-29 2014-08-05 Chevron Oronite Company Llc Natural gas engine lubricating oil compositions

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DE68902891D1 (de) 1992-10-22
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