EP0636680A1 - Schmiermittel für zweitaktmotor - Google Patents

Schmiermittel für zweitaktmotor Download PDF

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Publication number
EP0636680A1
EP0636680A1 EP94904735A EP94904735A EP0636680A1 EP 0636680 A1 EP0636680 A1 EP 0636680A1 EP 94904735 A EP94904735 A EP 94904735A EP 94904735 A EP94904735 A EP 94904735A EP 0636680 A1 EP0636680 A1 EP 0636680A1
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EP
European Patent Office
Prior art keywords
carbon atoms
groups
integer
nitrogen
containing compound
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.)
Withdrawn
Application number
EP94904735A
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English (en)
French (fr)
Other versions
EP0636680A4 (de
Inventor
Mitsuaki Central Technical Research Ishimaru
Mineo Central Technical Research Kagaya
Noboru Central Technical Research Ishida
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.)
Eneos Corp
Original Assignee
Nippon Oil Corp
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Publication date
Application filed by Nippon Oil Corp filed Critical Nippon Oil Corp
Publication of EP0636680A1 publication Critical patent/EP0636680A1/de
Publication of EP0636680A4 publication Critical patent/EP0636680A4/de
Withdrawn legal-status Critical Current

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    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/063—Complexes of boron halides
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    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
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    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • 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
    • F02B2075/025—Engines characterised by their cycles, e.g. six-stroke having less than six strokes per cycle two
    • 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
    • F02B77/00—Component parts, details or accessories, not otherwise provided for
    • F02B77/04—Cleaning of, preventing corrosion or erosion in, or preventing unwanted deposits in, combustion engines

Definitions

  • the present invention relates to a lubricating oil for two-cycle engines. More specifically, it relates to a lubricating oil for two-cycle engines, by the use of which an engine can remarkably reduce smoke, remarkably improve starting performance, be kept clean, even at high or low temperature, enough to prevent its exhaust system from clogging with carbon, and have an excellent anti-seizure performance.
  • Polybutene has been considered to cause clogging with carbon in an exhaust system less frequently than mineral oils. It, however, has been reported that polybutene produces more emulsion sludge at low temperature than mineral oils when used in particular two-cycle engines, for example, an engine of a motorcycle used for newspaper delivery which is exposed to frequent repetition of start-and-stop. Clogging of an exhaust system with carbon or emulsion causes deterioration of combustion performance of an engine, which leads to reduction of engine power.
  • a lubricating oil whose base oil is a polyalkylene glycol derivative with a particular structure is much more preferable with regard to engine power, starting performance and reduction of carbon clogging of an exhaust system than commercially available, conventional lubricating oils.
  • the present invention provides a lubricating oil for two-cycle engines which contains a polyalkylene glycol derivative of formula (1)(hereinafter referred to as "component A") as a base oil.
  • component A a polyalkylene glycol derivative of formula (1)(hereinafter referred to as "component A") as a base oil.
  • R1 and R2 represent hydrogen atoms; alkyl groups having 1 to 22 carbon atoms; cycloalkyl or alkylcycloalkyl groups having 5 to 20 carbon atoms; or aryl, alkylaryl or arylalkyl groups having 6 to 20 carbon atoms.
  • R1 and R2 include hydrogen atoms; alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl groups, and isomeric forms thereof; alkenyl groups such as propenyl, isopropenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexa
  • R1 and R2 in formula (1) are preferably hydrogen atoms, straight-chain or branched alkyl group having 1 to 18 carbon atoms, phenyl groups, or alkylphenyl groups, whose alkyl chains are straight or branched, having 7 to 18 carbon atmos.
  • R1 and R2 are preferably hydrogen atoms; methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, phenyl, tolyl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, dodecylphenyl or xylyl groups; or isomeric forms thereof.
  • R1 in formula (1) is preferably a hydrogen atom or a straight-chain or branched alkyl group having 1 to 4 carbon atoms (preferably a straight-chain alkyl group), more preferably a hydrogen atom, methyl, ethyl or propyl group or any one of their isomeric forms.
  • R2 in formula (1) is preferably a hydrocarbon group such as a straight-chain or branched alkyl group having 1 to 4 carbon atoms (preferably a straight-chain alkyl group), or an alkylphenyl group having 7 to 18 carbon atoms which consists of a phenyl group substituted by a straight-chain or branched alkyl group, among which methyl, ethyl, propyl, butyl, phenyl, tolyl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, dodecylphenyl or xylyl group, or any one of isomeric forms thereof.
  • a hydrocarbon group such as a straight-chain or branched alkyl group having 1 to 4 carbon atoms (preferably
  • R3, R4, R5 and R6 in formula (1) represent hydrogen atoms, methyl or ethyl groups, and the total number of carbons of R3, R4, R5 and R6 is 1 or 2.
  • a in formula (1) is an integer of 1 to 200, preferably 2 to 100, more preferably 5 to 50.
  • polyoxyalkylene glycol derivatives which can be used in a lubricating oil for two-cycle engines of the present invention have polyalkylene chains of formula (5).
  • the structure of formula (5) is one of the followings.
  • viscosity of component A at 100°C is preferably 1 to 100 mm2/s, more preferably 5 to 50 mm2/s, but not limited to them.
  • the lubricating oils of the present invention which contain component A as a base oil, can contain at least one of mineral lubricating oils, synthetic lubricating oils and/or mineral diluents as base oils, which are soluble in component A.
  • the total amount of the base-oil ingredients other than component A is preferably 100 parts or less to 100 parts of component A by weight, more preferably 50 parts or less as long as they do not deteriorate the characteristics of the lubricating oils of the present invention, but not limited to them.
  • component A At least one of the nitrogen-containing compounds of the following (a)-(d)(hereinafter referred to as "component B") can be added to improve cleanliness of an engine.
  • Component (a) is a nitrogen-containing compound represented by formula (2);
  • R7 is an alkyl group having 1 to 22 carbon atoms, an alkenyl group having 3 to 22 carbon atoms, a cycloalkyl or alkylcycloalkyl group having 5 to 15 carbon atoms, or an aryl, alkylaryl or arylalkyl group having 6 to 18 carbon atoms.
  • R7 is an alkyl group such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl groups, and any one of isomeric forms thereof; an alkenyl group such as propenyl, isopropenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecen
  • R7 in formula (2) is preferably a straight-chain or branched alkyl group having 1 to 18 carbon atoms, phenyl, or an alkylphenyl group having 7 to 18 carbon atoms whose alkyl chains are straight or branched.
  • R7 is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, phenyl, tolyl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, dodecylphenyl or xylyl group, or any one of their isomeric forms.
  • R8 and R 9 in formula (2) include hydrogen atoms or alkyl groups having 2 to 6 carbon atoms, and the total number of carbons of R8 and R9 is 2 to 8, preferably 2 to 6.
  • R8 and R9 are ethyl, propyl, butyl, pentyl or hexyl group, or any one of isomeric forms thereof, most preferably ethyl group.
  • b is an integer of 1 to 8, preferably 1 to 6, and c is an integer of 5 to 40, preferably 10 to 30.
  • component (b) mentioned above is a compound obtained through reaction of component (a) with a boronating agent.
  • an acid such as orthoboric acid(H3BO3), metaboric acid(HBO2), tetraboric
  • the boronating agent is preferably mono-, di- or trimethyl borate; mono-, di- or triethyl borate; mono-, di- or tripropyl borate; mono-, di- or tributyl borate; mono-, di- or tripentyl borate; mono-, di- or trihexyl borate; or any one of mixtures thereof, more preferably, an acid of boron, a lower alkyl ester of boric acid or any one of mixtures thereof.
  • the ratio of boron atoms of a boronating agent to nitrogen atoms of a nitrogen-containing compound of formula (2) is preferably 0.05-10:1, more preferably 0.1-2:1.
  • Boronation with a boronating agent is carried out by heating a nitrogen-containing compound of formula (2) with the boronating agent.
  • the boronation can be carried out in the presence of water, alcohol and/or hydrocarbon, as convenient.
  • water or alcohol is a "reactive solvent” which reacts with the boronating agent to form a reactive intermediate suitable for the boronation, resulting in an increase of yield, while hydrocarbon is an "inert solvent" which can azeotropically remove the water produced during the boronation.
  • Alcohols preferably used in the reaction include methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, pentanol(amyl or iso-amyl alcohol), hexanol, ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol and so forth.
  • Hydrocarbons preferably used in the reaction include those whose boiling point is 60°C or above, for example, benzene, toluene, xylene, benzine, lygroin, mineral spirit, cleaning solvent, petroleum naphtha, cyclohexane, hexane, mineral oil, and naphtha fraction, kerosine fraction, gas oil fraction or lubricating oil fraction of mineral oil.
  • reaction temperature during the boronation reaction should be to some extent higher than ambient temperature, preferably 50 to 250°C, more preferably 80 to 180°C, and a refluxing temperature of the solvent used is usually chosen. Since a boronation reaction can be usually completed in a short period of time, the reaction will be carried out for 0.5 to 8 hours, preferably 2 to 6 hours.
  • the reaction mixture After completing the boronation, the reaction mixture is heated to distill off the water produced during the reaction and any other solvents if used, and the water is usually removed by a desiccant such as sodium sulfate and magnesium sulfate. Then, the desired compound, component (b), can be obtained either 1)by diluting the reaction mixture with organic solvent such as benzene, toluene, xylene, hexane, benzine, gasoline for rubber or petroleum ether and removing the unreacted boronating agent by filtration or solvent extraction, or 2)through purification process such as distillation under a reduced pressure, as appropriate.
  • organic solvent such as benzene, toluene, xylene, hexane, benzine, gasoline for rubber or petroleum ether and removing the unreacted boronating agent by filtration or solvent extraction, or 2)through purification process such as distillation under a reduced pressure, as appropriate.
  • the ratio of the number of nitrogen atoms to the number of boron atoms in the nitrogen-containing compound can be controlled by adjusting the ratio of the amount of a boronating agent to a nitrogen-containing compound, and is preferably from 1:0.05 to 1:5, more preferably from 1:0.1 to 1:2.
  • Component (c) is a nitrogen-containing compound represented by formula (3);
  • X is a hydrogen atom or an acyl group having 6 to 30, preferably 12 to 20 carbon atoms which is derived from a fatty acid;
  • Y is an acyl group having 6 to 30, preferably 12 to 20 carbon atoms which is derived from a fatty acid;
  • R10 is an alkylene group having 2 to 4, preferably 2 or 3 carbon atoms;
  • d is an integer of 0 to 11, preferably 3 to 11, more preferably 4 to 11;
  • e is an integer of 0 to 11; 2 ⁇ d ⁇ + e ⁇ ⁇ 11 ; and one molecule contains at least one acyl group.
  • the fatty acid from which X or Y is derived can be a saturated or unsaturated fatty acid having 6 to 30 carbon atoms, preferably a saturated fatty acid having 12 to 20 carbon atoms, for example, a straight-chain or branched acid such as dodecanoic acid, tridecanoic acid ,tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanic acid, isododecanoic acid, isotridecanoic acid, isotetradecanoic acid, isopentadecanoic acid, isohexadecanoic acid, isoheptadecanoic acid, isooctadecanoic acid, isononadecanoic acid, isoeicosanic acid, or any one of mixtures thereof.
  • the alkylene group, R10 can be ethylene, propylene, trimethylene, tetramethylene, butylene, isobutylene or methyltrimethylene group, preferably ethelene, propylene or trimethylene group, most preferably ethylene group.
  • Component (c) is commercially available, or can be prepared by acylation of a polyalkylenepolyamine whose preferable structure is represented by formula (8).
  • R10 represents the same as R10 in formula (3), and i is an integer of 2 to 11, preferably 3 to 11, more preferably 4 to 11.
  • Examples of the above polyalkylenepolyamine include diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, heptaethyleneoctamine, octaethylenenonamine, nonaethylenedecamine, decaethyleneundecamine, undecaethylenedodecamine, dipropylenetriamine, tripropylenetetramine, tetrapropylenepentamine, pentapropylenehexamine, hexapropyleneheptamine, heptapropyleneoctamine, octapropylenenonamine, nonapropylenedecamine, decapropyleneundecamine, undecapropylenedodecamine, di(trimethylene)triamine, tri(trimethylene)tetramine, penta(trimethylene)hexamine, hexa(trimethylene)heptamine, hepta(trimethylene)octamine
  • acylating agent examples include a fatty acid having 6 to 30, preferably 12 to 20 carbon atoms, and its derivative such as an acid halide and an acid anhydride.
  • An acylating agent for the above polyalkylenepolyamine is used preferably in the amount of 0.1-1 moles per 1 mole of the polyalkylenepolyamine.
  • the acylation can be carried out under the conditions, e. g., reaction temperature, reaction time, catalyst and solvent, analogous to those usually applied to an acylation reaction and which are determined taking into consideration the types of the polyalkylenepolyamine and/or the acylating agent used, as convenient.
  • Component (d) can be obtained by a reaction of component (c) with a boronating agent, in which the boronating agent and the procedure of the boronation can be analogous to those used in the preparation of component (b), except that the amount of the boronating agent is from 0.05 to 5.0, preferably from 0.1 to 3.0 moles per 1 mol of component (c). It is recommended that in the reaction system the ratio of boron atoms to nitrogen atoms of compound (d) in number is 0.02-10, preferably 0.05-5.0, more preferably 0.1-2.
  • Component B is added to a lubricating oil for two-cycle engines comprising compound A as a base oil either directly or in the form of dilution of kerosine, lubricating oil or the like, to form a lubricating oil composition of the present invention, in which the content of compound B is 0.5-30 wt%, preferably 1-20 wt%, more preferably 3-10 wt%. Cleanliness will not be improved very much if the content of component B is below that range, while, if above, compound B does not improve cleanliness in proportion to the amount used, resulting in decrease of an economical efficiency. Hence, neither of these cases are preferable.
  • a process of mixing component A and B to prepare a lubricating oil composition for two-cycle engines of the present invention it can be usually obtained by stirring a mixture of these compounds at 20 to 80°C for 30 min to 3 hours.
  • the lubricating oil composition for two-cycle engines of the present invention which is excellent in cleanliness at low or high temperature, can be obtained by adding at least one nitrogen-containing compound selected from component (c) and (d) preferably to a polyalkylene glycol derivative as a base oil represented by formula (4); wherein R11 and R12 represent hydrogen atoms, alkyl groups having 1 to 4 carbon atoms, aryl, alkylaryl or arylalkyl groups having 6 to 20 carbon atoms, and R11 and/or R12 are aryl, alkylaryl or arylalkyl groups having 6 to 20 carbon atoms; R13, R14, R15 and R16 are hydrogen atoms, methyl groups or ethyl groups, and the total number of carbons of R13, R14, R15 and R16 is 1 or 2; and f is an integer of 1 to 200.
  • additives for lubricating oil such as antioxidant, load-resistant additive, metallic cleaner, ash-free dispersant, metal-inactivating agent, viscosity index improver, pour point depressant and defoaming agent, can be added to the lubricating oil, either solely or in combination of two or more thereof. It is important that these additives except deforming agent can be homogenously dissolved in a base oil of the lubricating oil for two-cycle engines of the present invention without turbidity or precipitation, and that, if added, they should be deliberately chosen. It is preferable to control the total content of the additives below or equal to 20 wt% to the total weight of the composition, but not limited.
  • Two-cycle engines referred to in the present invention are engines having a mechanism by which combustion is completed in one rotation of a crank-shaft.
  • the two-cycle engines can be used for various kinds of machine, for example, motorcycles, carts, snowmobiles, outboard motors, motorboats, marine skis, generators, chain saws, lawn mowers, sprays, pilotless light airplanes, fire pumps and so forth, without particular limitations.
  • the lubricating oil or oil composition for two-cycle engines of the present invention can be used to lubricate two-cycle engines without particular limitations in its usage.
  • the above-mentioned lubricating oil or oil composition( hereinafter referred to as "the Oil") can be fed into an engine in 1) a "mixed-oil system” in which the Oil and fuel are pre-mixed, placed in a fuel tank and vaporized to be fed into a crank case used as a pilot pressure chamber, or 2) a "separate-oil system” in which fuel and the Oil are placed in separate tanks and the Oil is fed into a crank case by an oil pump.
  • the Oil fed into a crank case in a manner described above lubricates bearing portions and frictional portions of the engine.
  • the bearing portions herein include crank bearings, connecting rod small end bearings, connecting rod large end bearings and a piston pin, and the frictional portions include a piston, a cylinder and a piston ring.
  • derivatives A to I used as base oils belong to component A, each of which is specifically shown in Table 1 by specifying R1 to R6 and a in formula (1).
  • nitrogen-containing compound A belongs to component (a) and is represented by formula (9).
  • a boronated nitrogen-containing compound A in the following examples belongs to component (b) and was prepared by the following boronation.
  • Nitrogen-containing compound B used in Example 1 is the compound represented by formula (11), which was prepared by the following process.
  • the contents in the reaction vessel were transferred into a one liter separatory funnel, and the lower layer was removed.
  • the upper benzene layer was washed 5 times with 300ml of purified water. After drying over anhydrous sodium sulfate, benzene was evaporated to obtain a light yellow transparent viscous liquid. Yield was 68g.
  • the result of elemental analysis of the product was carbon 75.2 wt%, hydrogen 13.1 wt% and nitrogen 9.2 wt%.
  • the boronated nitrogen-containing compound B used in the following examples is a compound prepared by boronation of nitrogen-containing compound B according to the process described below.
  • the reaction product was more viscous liquid than nitrogen-containing compound B prepared in the above preparation example.
  • a motorcycle equipped with a two-cycle engine( air-cooling type, 49 cc) was driven on road for about 10km, and was allowed to stand indoors for one hour and then at -5°C for 3 hours.
  • constant current(120 A) was applied to its starter motor for 10 seconds from outside of the cold room to start the engine, and the time required to complete 4 rotations of its crank was recorded.
  • the time was used as a standard for starting performance evaluation. The shorter the time is, the better starting performance is.
  • compositions of Examples 1 to 17 are the lubricating oils for two-cycle engines, which contain polyalkylene glycol derivatives of the present invention as a base oil. As is apparent from the results of the performance evaluation in Table 2, these lubricating oils produce smoke remarkably less in comparison with a mineral oil(Comparative Example 1), and also less in comparison with polybutene(Comparative Example 2) or commercially available low-smoke type of lubricating oils for two-cycle engines containing polybutene as a component of a base oil(Comparative Examples 3 and 4).
  • the time required to start an engine is usually desired to be less than or equal to that of a lubricating oil containing mineral oil(Comparative Example 1).
  • Any of the lubricating oils for two-cycle engines of Examples 1 to 17 of the present invention gave the time less than an oil containing mineral oil(Comparative Example 1) or a commercially available lubricating oil(Comparative Example 3 or 4), showing an excellent starting performance.
  • addition of polybutene has caused deterioration of starting performance of an engine(Comparative Example 2) due to its high viscosity.
  • the lubricating oil for two-cycle engines containing component (c) or (d)(Examples 15 or 17) has provided a low-temperature cleanliness superior to the lubricating oil without component (c) or (d)(Example 14), definitely showing effectiveness of addition of component (c) or (d).
  • the lubricating oils for two-cycle engines of the present invention have provided the time taken to occur clogging of a muffler three or more times longer than a conventional lubricating oil for two-cycle engines containing mineral oil (Comparative Example 1) or a conventional low-smoke type of lubricating oil for two-cycle engines(Comparative Example 3).
  • a lubricating oil for two-cycle engines of the present invention can remarkably inhibit generation of smoke and remarkably improve engine characteristics such as starting performance, cleanliness to prevent clogging with carbon of an exhaust system, high- or low temperature cleanliness of an engine, and anti-seizure performance.
EP94904735A 1993-01-20 1994-01-19 Schmiermittel für zweitaktmotor. Withdrawn EP0636680A4 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP7908/93 1993-01-20
JP5007908A JPH06212182A (ja) 1993-01-20 1993-01-20 ２サイクルエンジン用潤滑油
PCT/JP1994/000063 WO1994017163A1 (en) 1993-01-20 1994-01-19 Lubricant for a two cycle engine

Publications (2)

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EP0636680A1 true EP0636680A1 (de) 1995-02-01
EP0636680A4 EP0636680A4 (de) 1995-10-04

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0718393A1 (de) * 1994-07-06 1996-06-26 Mitsui Petrochemical Industries, Ltd. Einen aromatischen äther enthaltendes schmieröl
WO2009134638A2 (en) * 2008-04-28 2009-11-05 Dow Global Technologies Inc. Polyoxyalkylene glycol diether lubricating composition preparation and use

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001329283A (ja) * 2000-05-25 2001-11-27 Nippon Mitsubishi Oil Corp ２サイクルエンジン用潤滑油組成物
JP4573398B2 (ja) * 2000-05-30 2010-11-04 三洋化成工業株式会社 潤滑油
FR3048977B1 (fr) * 2016-03-15 2020-02-07 Total Marketing Services Composition lubrifiante a base de polyalkylene glycols

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US3871837A (en) * 1971-12-31 1975-03-18 Inst Francais Du Petrole Method for lubricating 2-stroke engines and rotary engines
EP0144922A2 (de) * 1983-12-03 1985-06-19 Mineralölwerke Wenzel und Weidmann Zweigniederlassung der Fuchs Mineralölwerke GmbH, Mannheim Schmiermittel
US4705643A (en) * 1984-08-30 1987-11-10 Standard Oil Company (Indiana) Detergent lubricant compositions
EP0297996A2 (de) * 1987-07-02 1989-01-04 Chevron Research And Technology Company Schmiermittel- und Brennstoffzusammensetzungen, die im wesentlichen geradkettige Alkylphenylpolyoxypropylenaminocarbamate enthalten
WO1991013950A1 (en) * 1990-03-15 1991-09-19 The Lubrizol Corporation Two-cycle engine fuel composition
EP0523560A1 (de) * 1991-07-19 1993-01-20 Idemitsu Kosan Company Limited Schmierölzusammensetzung für Zweitakt- oder Drehkolbenmotoren
US5330667A (en) * 1992-04-15 1994-07-19 Exxon Chemical Patents Inc. Two-cycle oil additive

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BE792960A (en) * 1971-12-31 1973-06-19 Inst Francais Du Petrole Lubrication of 2-stroke and rotary-piston engines - with lubricants contg polyalkylene glycol ethers and/or esters
JPS54160401A (en) * 1978-05-15 1979-12-19 Nippon Oil Co Ltd Two-cycle enging oil composition
JPS5676495A (en) * 1979-11-28 1981-06-24 Nippon Oil Co Ltd Lubricating oil composition for two-cycle engine

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US3871837A (en) * 1971-12-31 1975-03-18 Inst Francais Du Petrole Method for lubricating 2-stroke engines and rotary engines
EP0144922A2 (de) * 1983-12-03 1985-06-19 Mineralölwerke Wenzel und Weidmann Zweigniederlassung der Fuchs Mineralölwerke GmbH, Mannheim Schmiermittel
US4705643A (en) * 1984-08-30 1987-11-10 Standard Oil Company (Indiana) Detergent lubricant compositions
EP0297996A2 (de) * 1987-07-02 1989-01-04 Chevron Research And Technology Company Schmiermittel- und Brennstoffzusammensetzungen, die im wesentlichen geradkettige Alkylphenylpolyoxypropylenaminocarbamate enthalten
WO1991013950A1 (en) * 1990-03-15 1991-09-19 The Lubrizol Corporation Two-cycle engine fuel composition
EP0523560A1 (de) * 1991-07-19 1993-01-20 Idemitsu Kosan Company Limited Schmierölzusammensetzung für Zweitakt- oder Drehkolbenmotoren
US5330667A (en) * 1992-04-15 1994-07-19 Exxon Chemical Patents Inc. Two-cycle oil additive

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0718393A1 (de) * 1994-07-06 1996-06-26 Mitsui Petrochemical Industries, Ltd. Einen aromatischen äther enthaltendes schmieröl
EP0718393A4 (de) * 1994-07-06 1997-07-23 Mitsui Petrochemical Ind Einen aromatischen äther enthaltendes schmieröl
WO2009134638A2 (en) * 2008-04-28 2009-11-05 Dow Global Technologies Inc. Polyoxyalkylene glycol diether lubricating composition preparation and use
WO2009134638A3 (en) * 2008-04-28 2009-12-23 Dow Global Technologies Inc. Polyoxyalkylene glycol diether lubricating composition preparation and use

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WO1994017163A1 (en) 1994-08-04
EP0636680A4 (de) 1995-10-04

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