US3852204A - Lubricant compositions - Google Patents

Lubricant compositions Download PDF

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Publication number
US3852204A
US3852204A US00073572A US7357270A US3852204A US 3852204 A US3852204 A US 3852204A US 00073572 A US00073572 A US 00073572A US 7357270 A US7357270 A US 7357270A US 3852204 A US3852204 A US 3852204A
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Prior art keywords
percent
polybutene
lubricant
additive
oil
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US00073572A
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English (en)
Inventor
G Souillard
Quaethoven F Van
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Total Petrochemicals and Refining USA Inc
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Cosden Oil and Chemical Co
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    • 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
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/085—Phosphorus oxides, acids or salts
    • 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
    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen 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
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic 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
    • C10M2203/104—Aromatic fractions
    • C—CHEMISTRY; METALLURGY
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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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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
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    • C10M2203/106—Naphthenic fractions
    • C10M2203/1065—Naphthenic fractions used as base material
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    • C10M2203/108—Residual fractions, e.g. bright stocks
    • C10M2203/1085—Residual fractions, e.g. bright stocks used as base material
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    • C10M2205/0206—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers used as base material
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    • C10M2205/026—Butene
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    • C10M2205/026—Butene
    • C10M2205/0265—Butene used as base material
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    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
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    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027—Neutral salts thereof
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    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • 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
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    • C10M2211/06—Perfluorinated compounds
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    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
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    • C10N2040/25—Internal-combustion engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol fueled engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C10N2040/253—Small diesel engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/26—Two-strokes or two-cycle engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines
    • 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
    • C10N2050/015—Dispersions of solid lubricants
    • C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating

Definitions

  • ABSTRACT Lubricant compositions comprising:
  • This invention relates to lubrication of high and low speed four-stroke, spark-ignition and compressionignition engines, and two-stroke marine diesel engines which operate by having the lubricant directly injected into the cylinders, and particularly to a lubricant comprising a mixture of a liquid polybutene, mineral oil and a lubricant additive; and to operation of' such fourstroke and two-stroke engines with this lubricant.
  • Still another cause of premature wear of the piston and the cylinder walls is due to the lubricating system, which is by injection for the two-stroke marine diesel engines.
  • the lubricating system which is by injection for the two-stroke marine diesel engines.
  • increasingly high pressures exist between the cylinder walls and the piston rings and also larger spacing of the lubrication inlets on the cylinder walls, the size of which are now designed larger and larger, causes the injected lubricant to spread thereover with greater difficulty. This hinders uniformity and complete lubrication and, therefore, leads to an abnormal wear of the engine.
  • the present lubricant is superior to other common lubricants in that occasional contact with water or glycol from the cooling system will not result in precipitation of additives which remain homogeneously sus- 1 pended despite such aqueous contact and contamination.
  • a crankcase lubricant for four-cycle engines, spark-ignited as well as compression-ignited engines, markedly superior to solve the lubrication problems listed is provided by a composition comprising 10 to 24 percent liquid polybutene, 5 to percent mineral lubricating oil and l to 15 percent, preferably 3 to 15 percent, additive as defined below, the proportions being by weight.
  • the polybutene hereof is a light liquid polybutene or polyisobutylene or mixtures thereof; the polybutene is preferably hydrogenated.
  • the polybutene preferably has a viscosity ranging from 30 SSU at 210F (2.0 cst at 989C) to about 600 SSU at 2l0F (130 cst at 989C) and a molecular weight ranging from about 250 to 950.
  • the mineral oil component hereof is selected from any commercial lubricating mineral oil having a preferred viscosity in the range of about 50 to 1,000 SSU at F.
  • the additives useful herein are mineral oil sulfonic acid superbased with an alkali-forming metal oxide or hydroxide such as of an alkali or alkaline earth metal, typically potassium or sodium oxide or hydroxide, or calcium, magnesium, barium or strontium oxide or hy droxide. It is preferred to use the calcium petroleum sulfonic acid herein referred to as calcium sulfonate.
  • Such sulfonate is prepared by sulfonation of crude or fine petroleum fractions at a temperature of 50 200F, by reacting with a sulfonating agent, typically fuming sulfuric acid, for a period of about 30 60 minutes.
  • the mineral oil is a refined petroleum fraction solvent, refined with a solvent such as propane to remove usual impurities such as asphalt and waxes.
  • the base oil to be sulfonated may be any common oil, typically mid-continent oil, having a viscosity range of 50 230 SSUat 210F.
  • the sulfonated product soluble in the oil base is neutralized with calcium or barium oxide or hydroxide.
  • Such calcium petroleum sulfonic acid is available as a commercial product, for instance, Lubrizol 239, formed as described above.
  • the additive may further include a viscosity index improver such as polymethacrylate having a molecular weight range between about l0,000 20,000, typically about 15,000; and zinc dialkyldithiophosphate, typically zinc diethyldithiophosphate and diisobutyl catechol.
  • a viscosity index improver such as polymethacrylate having a molecular weight range between about l0,000 20,000, typically about 15,000
  • zinc dialkyldithiophosphate typically zinc diethyldithiophosphate and diisobutyl catechol.
  • typically useful additives may be a mixture of a superbased phosphonate and sulfonate of barium, both formed from mineral oil, such mixture typically having a sulfur content of 0.9 percent by weight, a phosphorous content of 1.44 percent by weight and a barium content of 7.05 percent by weight.
  • a third useful additive is one of the so-called ashless types, and consists of an alkenyl succinimide formed by reacting an alkylene polyamine consisting typically of triethylene tetramine or tetraethylene pentamine with alkenyl succinic anhydride to form the imide, the alkenyl substituent being an olefine of from about two to about sixteen carbon atoms, usually isobutylene or polyisobutylene. The preparation of that compound is as described in U.S. Pat. No. 3,310,492.
  • the polybutene imparts greater adhesion and rapid spread as well as increased anti-rust properties.
  • the formulation includes a quantity of polybutene in the range of l to 75 percent, preferably 12 to 24 percent.
  • An increased quantity of a specific additive is preferred; namely; a sulfonated mineral oil superbased with an alkaline earth metal oxideor-hydroxide, preferably of calcium, magnesium or barium formed as stated above, which is used in the preferred range of to 30 percent
  • the quantity of the mineral oil component is the remainder and is in the range of 5 to 80 percent, all proportions being by weight.
  • the viscosity and molecular weight characteristics of the preferred polybutene and mineral oil for both types of lubricant are the same as those given above.
  • a preferred method of forming the polybutene is shown in United States patent to Jackson, US. Pat. No. 2,957,930, issued Oct. 23, 1960. Such method forms a superior product in that the polybutene is formed more homogeneously in a narrow molecular weight range.
  • composition hereof adheres to the metal surfaces over long storage periods so that the anti-rust additive the compositioncontains is able to exert its full anti-rust effect.
  • FIG. 1 illustrates graphically the comparative results upon the relative merits of three oils -mineral oil, mineral oil and polyisobutylene, and mineral oil and hydrogenated isobutylene upon a piston skirt;
  • FIG. 2 has the same graphical illustrations as to the effect of these oils upon the piston lands
  • FIG. 3 graphically illustrates the effect of these same oils upon the piston grooves
  • FIG. 4 illustrates graphically the spreading effect of mineral oil containing additive A as identified before Table VI below, and
  • FIG. 5 comparatively graphically identifies a mixture of polyisobutylene and mineral oil.
  • EXAMPLE 1 Thermal Behaviour Test on the Antar Cokefaction Bench The purpose of this test is to determine the tendency of a lubricating oil to form varnish and carbon deposits in contact with a hot surface, such deposits being insoluble in petroleum ether.
  • the projection system is composed of a broom made of fine steel rods which dip into the oil, the broom being rotated at exactly 1,000 rpm by an electric motor.
  • the apparatus is practically closed and the cooling of the walls,.obtained through water circulation, brings about a condensation of the vapors, thereby ensuring an almost thorough recycling of the tested oil.
  • the hot metallic surface is represented by the external part of the bottom of an aluminum alloy Becker (of a composition similar to that of the pistons of a thermal engine) within which heating resistance are installed.
  • a control and regulation system connected to calibrated thermocouples keeps the hot surface within very narrow temperature limits; indeed, the amount of deposits formed increases almost exponentially with the temperature above 220/240C.
  • test conditions for an oil containing additives are as follows:
  • the additive X used below is composed predominantly of mixed barium superbased phosphonate and sulfonate having a sulfur content of 0.9 percent by weight, a barium content of 7.05 percent by weight, and a phosphorous content of 1.44 percent by weight, the balance being mineral oil residues with both phosphonates and sulfonates.
  • the total additive further contains about 2 percent of polymethacrylate having a molecular weight of about 15,000 and 1 percent of zinc diethyldithiophosphate.
  • a four-stroke single-cylinder diesel engine of 553 cm was used in accordance with the modified IP.l75/60T procedure of the War Office. This procedure is more severe than the standard CEC/AT4 method.
  • compositions 2 and 3 containing polybutene gave good results.
  • the additive Y is a commercial additive of the Ba and Ca superbased sulfonated mineral oil having a Ba content of 3.45 percent by wt., a Ca content of 3.55 percent by wt. and a S content of 2.3 percent by wt.
  • compositions 2 and 3 clearly show that the addition of a certain amount of polybutene greatly improves the ratings of the SNCB test.
  • the additive Z is a commercial additive of the Ba and Ca superbased sulfonated mineral oil having a Ba content of 4.3 percent by wt., a Ca content of 3.4 percent by weight and a S content of 2.4 percent by wt.
  • composition 1 Composition 2
  • Composition 3 Composition of the oil W/W 92% mineral oil 76% mineral oil 76% mineral oil 8 additive Y 8% additive Y 8% additive Y 16% polyybutene 16% hydrogenated polybutene Piston ring sticking I35 35 35 35 Scruper-ring sludge I 10 10 10 Carbon deposits in 9 9.25 10 the third groove.
  • the gasoline Petter tests are run with an oil having a paraffinic nature, and refined with a solvent.
  • the Ford test with the Cortina engine is commonly used for the purpose of studying the behaviour of oils at these high temperatures. This test is run on a four cylinder 1,500 cm engine under full load (48 HP at 35,000 r.p.m.) during 100 hours.
  • Additive A is a commercial additive comprising a Zn diethyldithiophosphate antioxidant having a Zn content of 8.6 by weight, and a P content of 7.7 percent by weight, and a detergent which is a Mg and Ca mineral oil sulfonate having an Mg content of 0.68 percent by weight and a Ca content of 0.23 percent by weight.
  • the skirt of the Becher is representative of the piston
  • the results presented in the table below were ob- I5 tained from three base oils having the same final viscosity; namely, 7 E50 or 53 cst at 50C.
  • curves are obtained which can be graphically derived in order to establish the spreading rate.
  • straight lines may be drawn between representative points and the angular coefficients of these straight lines taken as an average of the spreading rate under the test conditions.
  • the fuel used was a 600 Redwood preheated to 60C Lubrication is of the waste lubrication type; each cylinder having a mechanical lubricating system with multiple pumps of the type ASEA n BSP 4, which lubricates the cylinder (through four inlets), the piston trunnion and the big-end bearing.
  • the wear of the cylinder liner and of the rings is measured b. deposit, sludge and varnish on the piston and visiting ports are rated
  • the skirt rating is achieved by using the CRC/AT4 procedure, with a rating of 10 for an absolutely clean piston and a rating of for a piston completely covered with carbon.
  • This diesel engine uses a fuel with a viscosity of up to 3,000 sec.Redwood. It was found that the use of composition n '1 on this engine reduces the wear expressed in millimeters per 100 hrs. running by 50 percent.
  • a lubricant for internal combustion engines comprising from 10 to 75 percent of liquid polybutene having a viscosity in the range of about 30 up to 600 SSU at 210F and a molecular weight of less than about 1,000, to 80 percent mineral lubricating oil having a viscosity in the range of about 50 to 1,000 SSU at 100F, and 3 to 30 percent of a sulfonic acid superbased with an alkaline earth metal selected from the group consisting of calcium, barium and magnesium, the proportions being by weight.
  • Crackcase lubricant as defined in claim 1 for fourstroke spark-ignition and compression ignition engines comprising from to 24 percent of liquid polybutene.
  • Cylinder spray lubricant for low speed marine diesel engines as defined in claim 1 comprising from 10 to 24 percent of said liquid polybutene, 5 to 80 percent of said mineral lubricating oil and 5 to percent of said superbased sulfonate additive, the proportions being by weight.
  • a lubricant for internal combustion engines as defined in claim 1 further containing a small but effective quantity (comprising from 10 to of liquid polybutene having a viscosity in the range of about 30 up to 600 SSU at 210F and a molecular weight of less than about 1000, 5 to mineral lubricating oil having a viscosity in the range of about 50 to 1000 SSU at F, and 3 to 30%) of an alkylene polyamine amide TABLE X]
  • a small but effective quantity comprising from 10 to of liquid polybutene having a viscosity in the range of about 30 up to 600 SSU at 210F and a molecular weight of less than about 1000, 5 to mineral lubricating oil having a viscosity in the range of about 50 to 1000 SSU at F, and 3 to 30%
  • an alkylene polyamine amide TABLE X
  • EXAMPLE 9 The lubricating composition described under n 1 of Example 8 has been used successfully for many months of an alkenyl succinic acid in which the alkylene polyamine is triethylene tetramine or tetraethylene pentamine.
  • a lubricant for internal combustion engines as defined in claim 1 further containing a small but effective quantity of an alkylene polyamine amide of an alkenyl succinic acid in which the alkylene polyamine is triethylene tetramine or tetraethylene pentamine.
US00073572A 1966-02-01 1970-09-18 Lubricant compositions Expired - Lifetime US3852204A (en)

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4031020A (en) * 1974-05-31 1977-06-21 Nippon Oil Company, Ltd. Central system fluid composition
US4261841A (en) * 1979-12-18 1981-04-14 Phillips Petroleum Company Lubricating composition comprising hydrogenated oligomers of 1,3-diolefins and a calcium petroleum sulfonate
US4481122A (en) * 1983-03-21 1984-11-06 Witco Chemical Corporation Lubricant compositions
US4828727A (en) * 1987-10-29 1989-05-09 Birko Corporation Compositions for and methods of lubricating carcass conveyor
EP0331359A1 (de) * 1988-02-23 1989-09-06 Exxon Chemical Patents Inc. Dispersionsmittel für Schmiermittel im Schiffsdieselzylinder
US5089028A (en) * 1990-08-09 1992-02-18 Mobil Oil Corporation Deposit control additives and fuel compositions containing the same
US5347967A (en) * 1993-06-25 1994-09-20 Mcculloch Corporation Four-stroke internal combustion engine
US5599780A (en) * 1992-07-02 1997-02-04 Idemitsu Kosan Co., Ltd. Metal working oil composition
US5624890A (en) * 1994-11-28 1997-04-29 Nippon Oil Company, Ltd Lubricating oil composition for use in two-stroke cycle cylinder injection engine
WO1999006504A1 (en) * 1997-08-01 1999-02-11 Infineum Usa L.P. Lubricating oil compositions
US6140280A (en) * 1996-10-29 2000-10-31 Idemitsu Kosan Co., Ltd. Succinimide compound and method for producing it, lubricating oil additive comprising the compound and lubricating oil composition comprising the compound for diesel engine
US6159911A (en) * 1997-04-16 2000-12-12 Idemitsu Kosan Co., Ltd. Diesel engine oil composition
EP1100856A1 (de) * 1998-06-11 2001-05-23 ExxonMobil Oil Corporation Öl für zylinder eines dieselmotors
US20060270566A1 (en) * 2005-05-27 2006-11-30 Laurent Chambard Method of lubricating a crosshead engine

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US2304874A (en) * 1940-09-26 1942-12-15 Standard Oil Co Lubricant
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US2227692A (en) * 1939-12-19 1941-01-07 Standard Oil Co Diesel oil
US2304874A (en) * 1940-09-26 1942-12-15 Standard Oil Co Lubricant
US3004837A (en) * 1956-08-09 1961-10-17 Lawrence E Riemenschneider Fuel for two-cycle internal combustion engines
US3158572A (en) * 1957-06-10 1964-11-24 Socony Mobil Oil Co Inc High barium content complex salts of sulfonic acids and method for preparing same
US3076841A (en) * 1959-12-28 1963-02-05 Pure Oil Co Preparation of alkaline earth petroleum sulfonates
US3085978A (en) * 1960-02-25 1963-04-16 Phillips Petroleum Co Internal combustion engine lubricant
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US3105049A (en) * 1960-08-01 1963-09-24 Bray Oil Co Colloidal disperesions of salts
US3321399A (en) * 1961-10-20 1967-05-23 Exxon Research Engineering Co Preparation of oil dispersions of metal carbonates
US3285851A (en) * 1963-08-13 1966-11-15 Cosden Oil & Chem Co Lubricant
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US3298951A (en) * 1966-01-24 1967-01-17 Roman D Guminski Stabilized polybutene composition

Cited By (21)

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US4031020A (en) * 1974-05-31 1977-06-21 Nippon Oil Company, Ltd. Central system fluid composition
US4261841A (en) * 1979-12-18 1981-04-14 Phillips Petroleum Company Lubricating composition comprising hydrogenated oligomers of 1,3-diolefins and a calcium petroleum sulfonate
US4481122A (en) * 1983-03-21 1984-11-06 Witco Chemical Corporation Lubricant compositions
US4828727A (en) * 1987-10-29 1989-05-09 Birko Corporation Compositions for and methods of lubricating carcass conveyor
EP0331359A1 (de) * 1988-02-23 1989-09-06 Exxon Chemical Patents Inc. Dispersionsmittel für Schmiermittel im Schiffsdieselzylinder
US4948522A (en) * 1988-02-23 1990-08-14 Exxon Chemical Patents Inc. Dispersant for marine diesel cylinder lubricant
US5089028A (en) * 1990-08-09 1992-02-18 Mobil Oil Corporation Deposit control additives and fuel compositions containing the same
US5599780A (en) * 1992-07-02 1997-02-04 Idemitsu Kosan Co., Ltd. Metal working oil composition
US5347967A (en) * 1993-06-25 1994-09-20 Mcculloch Corporation Four-stroke internal combustion engine
US5579735A (en) * 1993-06-25 1996-12-03 Mcculloch Corporation Four-stroke internal combustion engine
US5624890A (en) * 1994-11-28 1997-04-29 Nippon Oil Company, Ltd Lubricating oil composition for use in two-stroke cycle cylinder injection engine
US6140280A (en) * 1996-10-29 2000-10-31 Idemitsu Kosan Co., Ltd. Succinimide compound and method for producing it, lubricating oil additive comprising the compound and lubricating oil composition comprising the compound for diesel engine
US6159911A (en) * 1997-04-16 2000-12-12 Idemitsu Kosan Co., Ltd. Diesel engine oil composition
WO1999006504A1 (en) * 1997-08-01 1999-02-11 Infineum Usa L.P. Lubricating oil compositions
EP1362906A2 (de) * 1997-08-01 2003-11-19 Infineum USA L.P. Verfahren zur Erhöhung der Kurbelgehäuseschmierölwechselzeit
EP1362906A3 (de) * 1997-08-01 2004-01-07 Infineum USA L.P. Verfahren zur Erhöhung der Kurbelgehäuseschmierölwechselzeit
EP1100856A1 (de) * 1998-06-11 2001-05-23 ExxonMobil Oil Corporation Öl für zylinder eines dieselmotors
US6339051B1 (en) * 1998-06-11 2002-01-15 Mobil Oil Corporation Diesel engine cylinder oils
EP1100856A4 (de) * 1998-06-11 2003-01-29 Exxonmobil Oil Corp Öl für zylinder eines dieselmotors
US20060270566A1 (en) * 2005-05-27 2006-11-30 Laurent Chambard Method of lubricating a crosshead engine
US8377857B2 (en) * 2005-05-27 2013-02-19 Infineum International Limited Method of lubricating a crosshead engine

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