EP0144922B1 - Lubricant - Google Patents

Lubricant Download PDF

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Publication number
EP0144922B1
EP0144922B1 EP84114499A EP84114499A EP0144922B1 EP 0144922 B1 EP0144922 B1 EP 0144922B1 EP 84114499 A EP84114499 A EP 84114499A EP 84114499 A EP84114499 A EP 84114499A EP 0144922 B1 EP0144922 B1 EP 0144922B1
Authority
EP
European Patent Office
Prior art keywords
lubricants
propylene oxide
mol
contain
oxide units
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP84114499A
Other languages
German (de)
French (fr)
Other versions
EP0144922A3 (en
EP0144922A2 (en
Inventor
Manfred Dr. Wildersohn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mineraloelwerke Wenzel und Weidmann Zweigniederla
Original Assignee
Mineralolwerke Wenzel und Weidmann Zweigniederlassung Der Fuchs Mineralolwerke Mannheim GmbH
Wenzel and Weidmann GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mineralolwerke Wenzel und Weidmann Zweigniederlassung Der Fuchs Mineralolwerke Mannheim GmbH, Wenzel and Weidmann GmbH filed Critical Mineralolwerke Wenzel und Weidmann Zweigniederlassung Der Fuchs Mineralolwerke Mannheim GmbH
Priority to AT84114499T priority Critical patent/ATE60081T1/en
Publication of EP0144922A2 publication Critical patent/EP0144922A2/en
Publication of EP0144922A3 publication Critical patent/EP0144922A3/en
Application granted granted Critical
Publication of EP0144922B1 publication Critical patent/EP0144922B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/76—Esters containing free hydroxy or carboxyl groups
    • 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
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/44—Five-membered ring containing nitrogen and carbon only
    • 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
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/44—Five-membered ring containing nitrogen and carbon only
    • C10M133/46—Imidazoles
    • C—CHEMISTRY; METALLURGY
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
    • C—CHEMISTRY; METALLURGY
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    • 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
    • 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
    • C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
    • C10M137/14—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond containing sulfur
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C—CHEMISTRY; METALLURGY
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
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    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2443—Organic compounds containing sulfur, selenium and/or tellurium heterocyclic compounds
    • C10L1/2456—Organic compounds containing sulfur, selenium and/or tellurium heterocyclic compounds sulfur with oxygen and/or nitrogen in the ring, e.g. thiazoles
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    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
    • C10L1/2616—Organic compounds containing phosphorus containing a phosphorus-carbon bond sulfur containing
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    • C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
    • C10L1/265—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) oxygen and/or sulfur bonds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
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    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
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    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
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    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C10M2209/1045—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only used as base material
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • C10M2219/106—Thiadiazoles
    • C—CHEMISTRY; METALLURGY
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    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • C—CHEMISTRY; METALLURGY
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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
    • C10M2223/041—Triaryl phosphates
    • C—CHEMISTRY; METALLURGY
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
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    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • 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
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B75/00—Other engines
    • F02B75/02—Engines characterised by their cycles, e.g. six-stroke
    • F02B2075/022—Engines characterised by their cycles, e.g. six-stroke having less than six strokes per cycle
    • F02B2075/027—Engines characterised by their cycles, e.g. six-stroke having less than six strokes per cycle four

Definitions

  • the invention relates to the use of lubricants based on polyol for two-stroke, four-stroke and rotary piston engines when operating the same with fuels which contain alcohol (s) and / or nitroalkane (s) and / or propylene oxide, the lubricant being added to the fuels and / or is in a separate lubricant circuit and the polyols consist of at least 40 mol% of propylene oxide units.
  • Lubricants with additions of polyols in engines that are operated with conventional hydrocarbon-based fuels are known.
  • DE-AS 17 94 133 describes lubricating oils which contain 0.01-5% by weight of a polyol which contains 10-40% by weight of ethylene oxide units.
  • Another component of the lubricants described in this document are oil-soluble substituted succinic acid compounds.
  • DE-PS 22 20 338 discloses water-soluble lubricants as metalworking and hydraulic fluids which consist of a relatively large mixing block made up of statistically distributed ethylene oxide and propylene oxide units.
  • DE-OS 23 45 540 describes lubricants for closed refrigerant circuits containing refrigerant, which consist of polyglycols.
  • the connecting rod plain bearings, roller bearings, in the crank mechanism and in the cam drive in two-stroke, four-stroke and rotary piston engines, in which fuel and lubricant are mixed, are lubricated by means of the oil coming in from the combustion chamber via the fuel. Blow-by gases when driving with a separate lubricant circuit that come into contact with the oil lead to corrosion in the crankcase when using castor oil and unalloyed synthetic oils as lubricants. Ester oils also do not work satisfactorily due to the formation of deposits on the piston and corrosion on brass parts of the ball bearings and the bronze bearings on the connecting rod.
  • the object of the present invention was therefore to provide a lubricant that meets the requirements in this field.
  • lubricants on polyol bases for the operation of two-stroke engines, four-stroke and rotary piston engines with fuels which contain alcohol (s) and / or nitroalkane (s) and / or propylene oxide, the lubricant being added to the fuels and / or is in a separate lubricant circuit, and the polyol (s) consists of more than 40 mol% propylene oxide units and contains an additive which comprises at least one thermally stable, ash-free detergent as components from nitrogen-containing organic compounds, contains at least one wear protection additive and at least one rust and at least one corrosion inhibitor.
  • Lubricants for two-stroke, four-stroke and rotary piston engines operated with mixed fuel (lubricant contained in the fuel) as well as four-stroke and rotary piston engines with a separate lubricant circuit are subject to numerous requirements. This includes perfect solubility in the fuel, certain viscosities depending on the temperature, good wear protection behavior, maintaining the cleanliness of the combustion chamber, avoiding sticking of the outlet slots, good corrosion protection, no gumming and varnishing, no formation of bridges on spark plugs, no deposits in ring grooves and piston crowns , Freedom of movement of the piston rings, sufficient lubricating effect with the addition of usual amounts of lubricant and self-miscibility with the fuel.
  • Polyester lubricants e.g. Polyester lubricants, polyol ethers and polyols.
  • Numerous polyols are commercially available products, e.g. Polyols which are composed of polyethylene oxide, of mixtures of polyethylene oxide and polypropylene oxide, of mixtures of the oxides mentioned with further olefin oxides, of polypropylene oxide and etherified and partially etherified polyols.
  • lubricants according to the invention were tested on two-stroke engines, four-stroke engines and rotary piston engines operated with particularly high loads using methanol and ethanol fuels.
  • the two-stroke test engines used for the investigation were air-cooled engines with a displacement of 35 cc each, an output of 1.7 KW (2.3 HP) each with a speed of 10,000 rpm.
  • the test runs were carried out at maximum output with new engines without a running-in period and a runtime of 5 hours each in full load operation and 150-200 hours part load operation.
  • Pure methanol was used as fuel, undistilled technical. Methanol (raw methanol), 95% ethanol and pure ethanol, ethanol / gasoline and methanol / gasoline as well as methanol / nitromethane or nitroethane, ethanol / nitromethane or nitroethane, methanol / nitromethane / propylene oxide, methanol / gasoline, propylene oxide, methanol / gasoline / Nitromethane, methanol / gasoline / nitromethane / propylene oxide and ethanol / gasoline / nitromethane / propylene oxide. Other ingredients were additives, small amounts of water and small amounts of ethers and hydrocarbons. The ratio of lubricants to fuel was 1:16, 1:40 and 1:50.
  • Table 1 The test results are summarized in Table 1. In all tests, 2.8% by weight of an additive which contained the above-mentioned components was added to the lubricant.
  • Table 2 shows results obtained with polyglycols from propylene oxide units of different viscosities.
  • Viscosities at 50 ° C are given.
  • the samples examined contained 2.8 and 3.4% by weight of an additive which contained the components indicated above.
  • Table 3 shows the cold behavior when standing for 10 hours with regard to precipitations.
  • the samples contained 3.4% by weight of additive.
  • Table 4 shows the cold behavior when standing for 10 hours with the addition of 10% by volume of ethanol.
  • the amount of additive was 3.4% by weight.
  • Table 2 shows that the lubricants based on propylene oxide provide perfect results even with different viscosities. Less satisfactory results occur only in the case of viscosity 240.
  • Table 3 shows that in the case of viscosity 40 from -15 ° C a slight turbidity occurs when standing for 10 hours, in the case of viscosities 80 and 140 only at -20 ° C. If an additional 10% by weight of ethanol is added to the lubricant, the clouding is eliminated in all cases (Tab. 4). The same was found with 10% additions of methanol, isopropanol and n-butanol.

Abstract

The polyol-based lubricants for two-stroke, four-stroke and rotary-piston engines operated with fuels containing alcohol(s) and/or nitroalkane(s) and/or propylene oxide, are added to the fuels and/or are in a separate lubricant circulation, the polyols consisting to the extent of at least 40 mol % of propylene oxide units.

Description

Gegenstand der Erfindung ist die Verwendung von Schmiermitteln auf Polyolbasis für Zweitakt-, Viertakt- und Rotationskolbenmotoren bei Betrieb derselben mit Kraftstoffen, die Alkohol(e) und/oder Nitroalkan(e) und/oder Propylenoxid enthalten, wobei das Schmiermittel den Kraftstoffen zugesetzt ist und/ oder sich in einem getrennten Schmiermittelkreislauf befindet und wobei die Polyole zu mindestens 40 Mol.-% aus Propylenoxideinheiten bestehen.The invention relates to the use of lubricants based on polyol for two-stroke, four-stroke and rotary piston engines when operating the same with fuels which contain alcohol (s) and / or nitroalkane (s) and / or propylene oxide, the lubricant being added to the fuels and / or is in a separate lubricant circuit and the polyols consist of at least 40 mol% of propylene oxide units.

Schmierstoffe mit Zusätzen von Polyolen in Motoren, die mit üblichen Kraftstoffen auf Kohlenwasserstoffbasis betrieben werden, sind bekannt.Lubricants with additions of polyols in engines that are operated with conventional hydrocarbon-based fuels are known.

So werden in der DE-AS 17 94 133 Schmieröle beschrieben, die 0,01-5 Gew.% eines Polyols enthalten, das zu 10-40 Gew.% Ethylenoxideinheiten enthält.DE-AS 17 94 133 describes lubricating oils which contain 0.01-5% by weight of a polyol which contains 10-40% by weight of ethylene oxide units.

Ein weiterer Bestandteil der in dieser Schrift beschriebenen Schmierstoffe sind öllösliche substituierte Bernsteinsäureverbindungen.Another component of the lubricants described in this document are oil-soluble substituted succinic acid compounds.

In DE-PS 22 20 338 werden wasserlösliche Schmiermittel als Metallbearbeitungs- und HydraulikFlüssigkeiten offenbart, die aus einem relative großen Mischblock aus statistisch verteilten Ethylenoxid-und Propylenoxideinheiten bestehen.DE-PS 22 20 338 discloses water-soluble lubricants as metalworking and hydraulic fluids which consist of a relatively large mixing block made up of statistically distributed ethylene oxide and propylene oxide units.

In DE-OS 23 45 540 werden Schmiermittel für geschlossene ein Kältemittel enthaltende Kältekreisläufe beschrieben, die aus Polyglykolen bestehen.DE-OS 23 45 540 describes lubricants for closed refrigerant circuits containing refrigerant, which consist of polyglycols.

In US-PS 3 287 271 werden kombinierte Detergens/Korrosions-Additive die Aminocarbonsäuren enthalten, als Zusätze zu Schmiermitteln für Benzinkraftstoffe offenbart.In U.S. Patent 3,287,271, combined detergent / corrosion additives containing aminocarboxylic acids are disclosed as additives to lubricants for gasoline fuels.

Zufriedenstellende Schmiermittel für Zweitaktmotoren, die mit Kraftstoffen betrieben werden, die Alkohol(e) und/oder Nitroalkan(e) und/oder Propylenoxid enthalten, sind zum gegenwärtigen Zeitpunkt nicht bekannt, obgleich durch die in vielen Ländern durchgeführten Entwicklungsarbeiten auf dem Gebiet alkoholtiger Kraftstoffe zunehmend ein Bedarf an zuverlässigen Schmiermitteln für mit solchen Kraftstoffen betriebene Motoren besteht. Auch für Viertakt- und Rotationskolbenmotoren, die mit Alkohole enthaltenden Mischungskraftstoffen in Analogie zu Zweitaktmotoren betrieben werden sowie für Viertakt-und Rotationskolbenmotoren mit getrenntem Schmierkreislauf, wobei jedoch Mischbarkeit des Schmiermittels mit dem Kraftstoff vorliegt, sind bisher geeignete Schmiermittel nicht bekannt. Die Schmierung der Pleuelgleitlager, Wälzlager, im Kurbeltrieb und im Nockentrieb in Zweitakt-, Viertakt- und Rotationskolbenmotoren, in denen Kraftstoff und Schmiermittel gemischt sind, erfolgt über das aus dem Brennraum kommende über den Kraftstoff eingebrachte Öl. Blow-by-Gase bei Fahrweise mit getrennten Schmiermittelkreislauf, die mit dem Öl in Berührung kommen, führen bei Einsatz von Rizinusöl und unlegierten Syntheseölen als Schmiermittel zu Korrosion im Kurbelgehäuse. Auch Esteröle wirken nicht zufriedenstellend infolge der Bildung von Ablagerungen am Kolben und Korrosion an Messingteilen der Kugellager und der Bronzelager am Pleuel.Satisfactory lubricants for two-stroke engines that run on fuels containing alcohol (s) and / or nitroalkane (s) and / or propylene oxide are not known at the present time, although the development work in many countries in the field of alcoholic fuels is increasing there is a need for reliable lubricants for engines powered by such fuels. Suitable four-stroke and rotary piston engines, which are operated with mixed fuels containing alcohols in analogy to two-stroke engines, and for four-stroke and rotary piston engines with a separate lubrication circuit, whereby the lubricant is miscible with the fuel, however, no suitable lubricants are known to date. The connecting rod plain bearings, roller bearings, in the crank mechanism and in the cam drive in two-stroke, four-stroke and rotary piston engines, in which fuel and lubricant are mixed, are lubricated by means of the oil coming in from the combustion chamber via the fuel. Blow-by gases when driving with a separate lubricant circuit that come into contact with the oil lead to corrosion in the crankcase when using castor oil and unalloyed synthetic oils as lubricants. Ester oils also do not work satisfactorily due to the formation of deposits on the piston and corrosion on brass parts of the ball bearings and the bronze bearings on the connecting rod.

Wie allgemein bekannt ist, werden aufwendige Untersuchungen durchgeführt zumindest teilweise Kraftstoffe auf Mineralölbasis durch Methanol- und Ethanol enthaltende Kraftstoffe zu ersetzen.As is generally known, complex investigations are carried out to at least partially replace petroleum-based fuels with fuels containing methanol and ethanol.

Aufgabe der vorliegenden Erfindung war es daher, ein Schmiermittel zur Verfügung zu stellen, das die Anforderungen auf diesem Gebiet erfüllt. Es wurde überraschend die Verwendung von Schmiermitteln auf Polyolbais für den Betrieb von Zweitaktmotoren, Viertakt- und Rotationskolbenmotoren mit Kraftstoffen gefunden, die Alkohol(e) und/oder Nitroalkan(e) und/oder Propylenoxid enthalten, wobei das Schmiermittel den Kraftstoffen zugesetzt ist und/oder sich in einem getrennten Schmiermittelkreislauf befindet, und wobei das (die) Polyol (e) aus mehr als 40 Mol.-% Propylenoxideinheiten besteht(en) und ein Additiv enthält (enthalten), das als Komponenten wenigstens ein thermisch stabiles, aschefreies Detergens bestehend aus Stickstoff enthaltenden organischen Verbindungen, wenigstens ein Verschleißschutzadditiv sowie wenigstens einen Rost- und wenigstens einen Korrosionsinhibitor enthält.The object of the present invention was therefore to provide a lubricant that meets the requirements in this field. Surprisingly, the use of lubricants on polyol bases for the operation of two-stroke engines, four-stroke and rotary piston engines with fuels was found, which contain alcohol (s) and / or nitroalkane (s) and / or propylene oxide, the lubricant being added to the fuels and / or is in a separate lubricant circuit, and the polyol (s) consists of more than 40 mol% propylene oxide units and contains an additive which comprises at least one thermally stable, ash-free detergent as components from nitrogen-containing organic compounds, contains at least one wear protection additive and at least one rust and at least one corrosion inhibitor.

An Schmierstoffe für mit Mischungskraftstoff (Schmiermittel im Kraftstoff enthalten) betriebene Zweitakt-, Viertakt- und Rotationskolbenmotoren sowie Viertakt- und Rotationskolbenmotoren mit getrenntem Schmiermittelkreislauf werden zahlreiche Anforderungen gestellt. Hierzu gehören einwandfreie Löslichkeit im Kraftstoff, bestimmte Viskositäten in Abhangigkeit von der Temperatur, gutes Verschleißschutzverhalten, Aufrechterhaltung der Sauberkeit des Brennraumes, Vermeidung von Verklebungen der Auslaßschlitze, guter Korrosionsschutz, kein Verharzungen und Verlackungen, Ausbleiben von Brückenbildungen an Zündkerzen, keine Ablagerungen in Ringnuten und Kolbenböden, Freigängigkeit der Kolbenringe, ausreichende Schmierwirkung bei Zusatz üblicher Schmiermittelmengen sowie Selbstmischbarkeit mit dem Kraftstoff.Lubricants for two-stroke, four-stroke and rotary piston engines operated with mixed fuel (lubricant contained in the fuel) as well as four-stroke and rotary piston engines with a separate lubricant circuit are subject to numerous requirements. This includes perfect solubility in the fuel, certain viscosities depending on the temperature, good wear protection behavior, maintaining the cleanliness of the combustion chamber, avoiding sticking of the outlet slots, good corrosion protection, no gumming and varnishing, no formation of bridges on spark plugs, no deposits in ring grooves and piston crowns , Freedom of movement of the piston rings, sufficient lubricating effect with the addition of usual amounts of lubricant and self-miscibility with the fuel.

Gute Löslichkeit in Alkoholkraftstoffen besitzen z.B. Polyesterschmiermittel, Polyolether sowie Polyole. Zahlreiche Polyole sind marktübliche Produkte, so z.B. Polyole, die aufgebaut sind aus Polyethylenoxid, aus Gemischen von Polyethylenoxid und Polypropylenoxid, aus Gemischen der genannten Oxide mit weiteren Olefinoxiden, aus Polypropylenoxid sowie veretherte und teilweise veretherte Polyole.Have good solubility in alcohol fuels e.g. Polyester lubricants, polyol ethers and polyols. Numerous polyols are commercially available products, e.g. Polyols which are composed of polyethylene oxide, of mixtures of polyethylene oxide and polypropylene oxide, of mixtures of the oxides mentioned with further olefin oxides, of polypropylene oxide and etherified and partially etherified polyols.

Überraschend wurde gefunden, daß nur solche Polyole die genannten Erfordernisse bei Einsatz von Kraftstoffen, die Alkohol(e) und/oder Nitroalkane und/oder Propylenoxid enthalten in hervorragender Weise erfüllen, die aus mehr als 40 Mol.% aus Propylenoxideinheiten aufgebaut sind, wobei bis zu 60% Ethylenoxidoder andere Olefinoxideinheiten enthalten sein können. Ferner haben die Untersuchungen ergeben, daß die geeigneten Additive für solche Schmiermittel thermisch stabile, aschefreie Detergentien im Schmiermittel sind, bestehend aus Stickstoff enthaltenden organischen Verbindungen. Zusätzlich sind in den erfingungsgemäßen Schmiermitteln Verschleißschutzkomponenten sowie Rost- und Korrosionsinhibitoren enthalten. Als Stickstoff enthaltende Detergentien können z.B.Surprisingly, it was found that only those polyols meet the requirements mentioned above when using fuels which contain alcohol (s) and / or nitroalkanes and / or propylene oxide, which are composed of more than 40 mol% of propylene oxide units, with up to may contain 60% ethylene oxide or other olefin oxide units. Furthermore, the studies have shown that the suitable additives for such lubricants are thermally stable, ash-free detergents in the lubricant, consisting of nitrogen-containing organic compounds. In addition are Wear protection components as well as rust and corrosion inhibitors are contained in the lubricants according to the invention. Detergents containing nitrogen can, for example

Reaktionsprodukte durch Umsetzung von Alkylbernsteinsäureanhydrid mit Polyaminen, Benzylamin-Derivate u.a.

  • verwendet werden.
  • Geeignete Verschleißschutzkomponenten sind z.B.
    • Thiophosphor- und Thiophosphonsäureester Triphenylphosphit u.a.
  • Geeignete Rostschutzkomponenten sind z.B.
    • Alkenylbernsteinsäurehalbester
    • Fettsäureamide
    • Alkyl-phenoxycarbonsäuren
    • Substituiertes Imidazolin u.a.
  • Geeignete Korrosionsinhibitoren sind z.B.
    • Benzotriazol, 2-Mercaptobenzothiazol,
    • N-Acylsarcosin u.a.
Reaction products by reacting alkyl succinic anhydride with polyamines, benzylamine derivatives and others
  • be used.
  • Suitable wear protection components are, for example
    • Thiophosphoric and thiophosphonic acid esters triphenyl phosphite and others
  • Suitable rust protection components are, for example
    • Alkenyl succinic acid semiesters
    • Fatty acid amides
    • Alkyl phenoxy carboxylic acids
    • Substituted imidazoline and others
  • Suitable corrosion inhibitors are, for example
    • Benzotriazole, 2-mercaptobenzothiazole,
    • N-acylsarcosine and others

Die angegebenen Additiv-Komponenten sind beispielhaft und nicht als den Schutzumfang der vorliegenden Erfindung einschränkend anzusehen.The indicated additive components are exemplary and should not be viewed as limiting the scope of the present invention.

Die erfindungsgemäße Verwendung von Schmierstoffen sowie die Verwendung von Vergleichsschmierstoffen wurden an besonders hochbeanspruchten mit Methanol- und Ethanolkraftstoffen betriebenen Zweitaktmotoren, Viertakt- und Rotationskolbenmotoren gestestet.The use of lubricants according to the invention and the use of comparative lubricants were tested on two-stroke engines, four-stroke engines and rotary piston engines operated with particularly high loads using methanol and ethanol fuels.

Die zur Untersuchung verwendeten Zweitakt-Testmotoren waren luftgekühlte Motoren mit einem Hubraum von je 35 ccm, einer Leistung von je 1,7 KW (2,3 PS) mit einer Drehzahl von je 10 000 u/min. Die Prüfläufe wurden bei maximaler Leistung mit neuen Motoren ohne Einlaufperiode und einer Laufzeit von jeweils 5 Stunden in Vollastbetrieb und 150-200 Stunden Teillastbetrieb durchgeführt.The two-stroke test engines used for the investigation were air-cooled engines with a displacement of 35 cc each, an output of 1.7 KW (2.3 HP) each with a speed of 10,000 rpm. The test runs were carried out at maximum output with new engines without a running-in period and a runtime of 5 hours each in full load operation and 150-200 hours part load operation.

Desweiteren wurden Versuche in Zweitakt- und Viertakt-Motoren durchgeführt, wie sie z.B. für Modellflugzeuge verwendet werden, nämlich Motoren mitFurthermore, tests were carried out in two-stroke and four-stroke engines, e.g. be used for model aircraft, namely engines with

Figure imgb0001
Figure imgb0001

Die Versuche in einem Rotationskolbenmotor wurden mit einem Wankelmotor durchgeführt mit 0,6 KW Leistung, 25 000 U/min und 5 ccm Kammervolumen. Getestet wurden Schmiermittel aus

  • 1. Esterölen
  • 2. Polyethylenoxid
  • 3. Ethylenoxid-(EO), Propylenoxid-(PO) and Butylenoxid-1,2 (BO)-Einheiten
  • 4. tert.-butyliertem Polyethylenoxid
  • 5. tert.-butyliertem Polypropylenoxid.
The tests in a rotary piston engine were carried out with a Wankel engine with 0.6 KW output, 25,000 rpm and 5 ccm chamber volume. Lubricants were tested out
  • 1. Ester oils
  • 2. polyethylene oxide
  • 3. Ethylene oxide (EO), propylene oxide (PO) and butylene oxide-1,2 (BO) units
  • 4. tert-butylated polyethylene oxide
  • 5. tert-butylated polypropylene oxide.

Als Kraftstoffe wurden verwendet Reinmethanol, nicht destilliertes techn. Methanol (Rohmethanol), 95 %iges Ethanol und Reinethanol, Ethanol/Benzin und Methanol/Benzin sowie Methanol/Nitromethan bzw. Nitroethan, Ethanol/Nitromethan bzw. Nitroethan, Methanol/Nitromethan/Propylenoxid, Methanol/Benzin, Propylenoxid, Methanol/Benzin/Nitromethan, Methanol/Benzin/Nitromethan/Propylenoxid und Ethanol/ Benzin/Nitromethan/Propylenoxid. Weitere Bestandteile waren Additive, kleine Mengen an Wasser bzw. kleine Mengen an Ethern und Kohlenwasserstoffen. Das Verhältnis von Schmiermitteln zu Kraftstoff betrug 1:16, 1:40 und 1:50.Pure methanol was used as fuel, undistilled technical. Methanol (raw methanol), 95% ethanol and pure ethanol, ethanol / gasoline and methanol / gasoline as well as methanol / nitromethane or nitroethane, ethanol / nitromethane or nitroethane, methanol / nitromethane / propylene oxide, methanol / gasoline, propylene oxide, methanol / gasoline / Nitromethane, methanol / gasoline / nitromethane / propylene oxide and ethanol / gasoline / nitromethane / propylene oxide. Other ingredients were additives, small amounts of water and small amounts of ethers and hydrocarbons. The ratio of lubricants to fuel was 1:16, 1:40 and 1:50.

Gepruft wurden:

  • a) Löslichkeit des Schmiermittels im Kraftstoff
  • b) Sauberkeit des Brennraumes
  • c) Sauberkeit der Kolbenringnuten
  • d) Freßstellen und Riefen an den Motorteilen, Verschleiß
  • e) Freigängigkeit der Kolbenringe
  • f) Korrosion an Motorteilen
  • d) Verlackungen an Kolbenboden und -hemd
  • h) Verkleungen an den Auslaßschlitzen
  • i) Brückenbildung an Zündkerzen
  • j) Ablagerungen
The following were checked:
  • a) Solubility of the lubricant in the fuel
  • b) cleanliness of the combustion chamber
  • c) Cleanliness of the piston ring grooves
  • d) Seizure and scoring on the engine parts, wear
  • e) Clearance of the piston rings
  • f) Corrosion on engine parts
  • d) lacquering of the piston crown and shirt
  • h) Gluing at the outlet slots
  • i) Bridging on spark plugs
  • j) deposits

In Tabelle 1 sind die Prüfergebnisse zusammengestellt. In allen Versuchen waren dem Schmiermittel 2,8 Gew.% eines Additivs zugesetzt, das die oben angegebenen Komponenten enthielt. In Tabelle 2 sind Ergebnisse zusammengestellt, die mit Polyglykolen aus Propylenoxideinheiten von unterschiedlicher Viskosität erhalten wurden.The test results are summarized in Table 1. In all tests, 2.8% by weight of an additive which contained the above-mentioned components was added to the lubricant. Table 2 shows results obtained with polyglycols from propylene oxide units of different viscosities.

Angegeben sind Viskositäten bei 50°C. Die untersuchten Proben enthielten 2,8 und 3,4 Gew.% eines Additivs, das die oben angegebenen Komponenten enthielt.Viscosities at 50 ° C are given. The samples examined contained 2.8 and 3.4% by weight of an additive which contained the components indicated above.

In Tabelle 3 ist das Kälteverhalten bei 10-stündigem Stehen in Bezug auf Ausfällungen angegeben. Die Proben enthielten 3,4 Gew.% Additiv.Table 3 shows the cold behavior when standing for 10 hours with regard to precipitations. The samples contained 3.4% by weight of additive.

In Tabelle 4 ist das Kälteverhalten bei 10-stündigem Stehen bei Zusatz von 10 Vol.-% Ethanol angegeben. Die Additivmenge betrug 3,4 Gew.-%.Table 4 shows the cold behavior when standing for 10 hours with the addition of 10% by volume of ethanol. The amount of additive was 3.4% by weight.

Die Untersuchungen zeigen für den Fachmann überraschend, daß Polyglykole, die zu mehr als 40 Mol.- % aus Propylenoxideinheiten aufgebaut sind, bei allen Tests einwandfreie Ergebnisse liefern, wie Tabelle 1 zeigt. Bei allen anderen Schmiermitteln traten zumindest bei einem Teil der durchgeführten Tests Schäden auf.For the person skilled in the art, the investigations surprisingly show that polyglycols which are composed of more than 40 mol% of propylene oxide units give perfect results in all tests, as shown in Table 1. For all other lubricants, damage occurred in at least some of the tests carried out.

Aus Tabelle 2 geht hervor, daß die Schmiermittel auf Propylenoxidbasis auch bei unterschiedlichen Viskositäten einwandfreie Ergebnisse liefern. Nur im Falle der Viskosität 240 treten weniger zufriedenstellende Ergebnisse auf.Table 2 shows that the lubricants based on propylene oxide provide perfect results even with different viscosities. Less satisfactory results occur only in the case of viscosity 240.

Die in den Tabellen 1, 2, 3 und 4 angegebenen Ergebnisse wurden sowohl mit den oben genannten Methanol- als auch Ethanolkraftstoffen erhalten.The results given in Tables 1, 2, 3 and 4 were obtained with both the methanol and ethanol fuels mentioned above.

Tabelle 3 zeigt, daß im Falle der Viskosität 40 ab -15°C eine leichte Trübung bei 10-stündigem Stehen auftritt, im Falle der Viskositäten 80 und 140 erst bei - 20°C. Werden zusätzlich 10 Gew.-% Ethanol zum Schmiermittel zugefügt, unterleibt in allen Fällen die Trübung (Tab. 4). Das gleiche wurde gefunden bei 10- %igen Zusätzen von Methanol, Isopropanol und n-Butanol.Table 3 shows that in the case of viscosity 40 from -15 ° C a slight turbidity occurs when standing for 10 hours, in the case of viscosities 80 and 140 only at -20 ° C. If an additional 10% by weight of ethanol is added to the lubricant, the clouding is eliminated in all cases (Tab. 4). The same was found with 10% additions of methanol, isopropanol and n-butanol.

Die untersuchungen machen deutlich, daß die erfindungsgemäßen Schmiermittel für den Betrieb von Zweitakt-, Viertakt- und Rotationskolbenmotoren mit Alkoholkraftstoffen, denen das Schmiermittel zugesetzt ist oder ein getrennter Schmiermittelkreislauf vorhanden ist, hervorragend geeignet sind.

Figure imgb0002
Figure imgb0003
Figure imgb0004
Figure imgb0005
 The investigations make it clear that the lubricants according to the invention are outstandingly suitable for the operation of two-stroke, four-stroke and rotary piston engines with alcohol fuels to which the lubricant has been added or a separate lubricant circuit is present.
Figure imgb0002
Figure imgb0003
Figure imgb0004
Figure imgb0005

Claims (7)

1. Use of lubricants based on polyols for the operation of two-cycle, four-cycle and rotational piston engines with fuels, which contain alcohol(s) and/or nitroalkanes, in particular nitromethane and/or propyleneoxide, whereby the lubricant is either added to the fuel and/or is present in a separate lubricating cycle and whereby the polyol(s) consist of more than 40 mol-% of propylene oxide units and contain an additive, which contains as components at least one thermally stable detergent free of ash, which consists of a nitrogen containing organic compound, at least one anti-abrasive additive and at least one anti-rust and at least one anti-corrosive agent.
2. Use of lubricants according to claim 1, characterized in that the fuel contains 1-15 parts per volume of the polyol(s) per 100 parts per volume of fuel.
3. Use of lubricants according to claims 1 and 2, characterized in that the polyol(s) consist of at least 75 mol-% of propylene oxide units.
4. Use of lubricants according to claims 1-3, characterized in that the lubricants contain a blend of polyols of different viscosity consisting each of more than 40 mol-% of propylene oxide units.
5. Use of lubricants according to claims 1-4, characterized in that the lubricants contain a blend of polyols of different viscosity consisting each of at least 75 mol-% of propylene oxide units.
6. Use of lubricants according to claims 1-5, characterized in that they in addition contain alcohols.
7. Use of lubricants according to claims 1-6, characterized in that the alcohols added are C1-C6- alcohols.
EP84114499A 1983-12-03 1984-11-29 Lubricant Expired - Lifetime EP0144922B1 (en)

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DE3708338A1 (en) * 1987-03-14 1988-09-22 Basf Ag FUELS CONTAINING LOW QUANTITIES OF ALKOXYLATES AND POLYCARBONIC ACID IMIDES
DE3711985A1 (en) * 1987-04-09 1988-10-20 Union Rheinische Braunkohlen USE OF POLYOLETHERS TO PREVENT OR REDUCE DEPOSITS IN MIXTURE PROCESSING SYSTEMS
US5114436A (en) * 1987-04-20 1992-05-19 Betz Laboratories, Inc. Process and composition for stabilized distillate fuel oils
FR2633638B1 (en) * 1988-06-29 1991-04-19 Inst Francais Du Petrole FORMULATIONS OF NITROGEN ADDITIVES FOR ENGINE FUELS AND THE ENGINE FUELS CONTAINING THE SAME
FR2646434B2 (en) * 1988-06-29 1991-08-30 Inst Francais Du Petrole FORMULATION OF FUEL ADDITIVES COMPRISING AT LEAST ONE COMPOSITION OBTAINED FROM A HYDROXYMIDAZOLINE AND A POLYAMINE AND ITS USE AS A FUEL ADDITIVE
DE68902891T2 (en) * 1988-07-22 1993-03-25 Akzo Nv SYNTHETIC LUBRICANT COMPOSITION.
JPH06212182A (en) * 1993-01-20 1994-08-02 Nippon Oil Co Ltd Lubricating oil for 2-cycle engine
DE19647554A1 (en) * 1996-11-16 1998-05-28 Daimler Benz Ag Functional fluid for lifetime lubricated internal combustion engines
WO2013066702A2 (en) * 2011-11-01 2013-05-10 Dow Global Technologies Llc Oil soluble polyalkylene glycol lubricant compositions

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