EP0341574B1 - Schmiermittelzusammensetzung - Google Patents

Schmiermittelzusammensetzung Download PDF

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Publication number
EP0341574B1
EP0341574B1 EP89108062A EP89108062A EP0341574B1 EP 0341574 B1 EP0341574 B1 EP 0341574B1 EP 89108062 A EP89108062 A EP 89108062A EP 89108062 A EP89108062 A EP 89108062A EP 0341574 B1 EP0341574 B1 EP 0341574B1
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EP
European Patent Office
Prior art keywords
oil
lubricating oil
weight
oil composition
mineral oil
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
EP89108062A
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English (en)
French (fr)
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EP0341574A1 (de
Inventor
Hata Hitoshi
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.)
Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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Publication of EP0341574A1 publication Critical patent/EP0341574A1/de
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    • C10M101/00Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02Petroleum fractions
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    • C10M107/00Lubricating compositions characterised by the base-material being a macromolecular compound
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    • C10M111/00Lubrication 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
    • C10M111/04Lubrication 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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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106Thiadiazoles
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00Organic 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
    • C10M2227/06Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061Esters derived from boron
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/04Groups 2 or 12
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/12Groups 6 or 16
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01Physico-chemical properties
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/02Bearings
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/04Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/04Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/04Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/04Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives

Definitions

  • the present invention relates to a lubricating oil composition. More specifically, it is concerned with a lubricating oil composition which is low in fatigue failure of a metal under repeated high contact stress, and also high in a traction coefficient, and yet excellent in oxidation resistance.
  • the lubricating oil composition is suitable for a lubricating oil for power transmitting devices such as gears, bearings, traction drive mechanisms, etc.
  • Lubricating oils using such paraffin type mineral oils are unsatisfactory in pitting resistance or traction coefficient under repeated high contact stress, and there also is a problem that oxidation resistance is not sufficiently satisfied.
  • the present inventor has conducted earnest research to overcome the problems of the aforesaid conventional lubricating oils and to develop a lubricating oil showing high fatigue failure resistance, high traction characteristics and excellent oxidation resistance under repeated high contact stress.
  • the present invention has been accomplished based on such findings.
  • the present invention is to provide a lubricating oil composition which comprises a base oil of
  • the mineral oil alone of the component (A), or a mixture of the component (A) and the component (B), a polybutene having a molecular weight of 200 to 1000 is used as the base oil for the lubricating oil.
  • the mineral oil to be used as the component (A) has the kinematic viscosity at 40°C of 2 to 2000 mm2/s (cSt), preferably 5 to 1000 and more preferably 10 to 500 mm2/s (cSt). If it is less than 2 mm2/s (cSt), oil film forming ability is low so that friction becomes undesirably marked.
  • this mineral oil should have a viscosity index of 70 or higher, preferably 75 or higher.
  • the viscosity index is less than 70, oxidation resistance of the composition is insufficient.
  • the above mineral oil should have a nitrogen content of 20 ppm or less, preferably 10 ppm or less.
  • the bromine value it should have 25 or less, preferably 10 or less. If either the nitrogen content exceeds 20 ppm or the bromine value exceeds 25, it is undesirable since fatigue lifetime lowers.
  • any mineral oils can be used so long as they have the aforesaid properties, but considering a low temperature characteristic, it is preferred that they have a pour point of -20°C or lower, more preferably -30°C or lower.
  • any materials which can be obtained by various methods are acceptable so long as they have the aforesaid properties, but more preferably, there may be mentioned a purified oil which is obtained by purifying a distillate oil with the usual method, said distillate oil having been obtained by atmospheric distillation of a paraffin base crude oil or an intermediate base crude oil, or by vacuum distillation of a residual oil resulting from the atmospheric distillation, and a deep dewaxed oil which is obtained by subjecting the above purified oil to deep dewaxing treatment.
  • the process for purification of the distillate oil is not critical, and various methods can be employed.
  • the distillate oil is purified by applying such treatments as (a) hydrogenation, (b) dewaxing (solvent dewaxing or hydrogenation dewaxing), (c) solvent extraction, (d) alkali distillation or sulfuric acid treatment, and (e) clay filtration, alone or in combination with one another. It is also effective to apply the same treatment repeatedly in multi-stages.
  • a mineral oil obtained by deep dewaxing is preferred as the base oil.
  • This deep dewaxing treatment is carried out by solvent dewaxing under severe conditions, or by catalytic hydrogenation dewaxing using a Zeolite catalyst.
  • the above mineral oil of the component (A) may be singly used as the base oil, and a combination of a polybutene having a molecular weight of 200 to 1000 of the component (B) and the mineral oil may be also used as the base oil.
  • the polybutene of the component (B) has a molecular weight of 200 to 1000 (this corresponds to a kinematic viscosity at 40°C of 2 to 4000 mm2/s (cSt)), and preferably 300 to 800.
  • this polybutene may be one which is hydrogenated or not hydrogenated.
  • the base oil for the lubricating oil of the present invention contains 100 to 5% by weight, preferably 100 to 20% by weight, most preferably 90 to 20% by weight of the mineral oil of the component (A), and 0 to 95% by weight, preferably 0 to 80% by weight, most preferably 10 to 80% by weight of the polybutene of the component (B). If the ratio of the mineral oil is less than 5% by weight, it causes the problem that the anti-wear resistance and anti-seizure property become insufficient under severe conditions (poor lubricating condition).
  • the base oil for the lubricating oil comprising the above component (A) or a mixture of the component (A) and the component (B), at least one additive selected from an extreme pressure agent, an anti-wear agent and an oiliness agent, is necessarily formulated.
  • an extreme pressure agent various compounds can be used.
  • sulfur-based extreme pressure agents such as sulfides, sulfoxides, sulfone, thiophosphinates, thiocarbonates, dithiocarbamates, alkylthiocarbamoyls, fats and oils, sulfurized fats and oils, sulfurized olefin and the like; phosphorus-based extreme pressure agents such as phosphoric acid esters, phosphorous acid esters, phosphoric acid ester amine salts, phosphorous acid ester amine salts, and the like; halogen-based extreme pressure agents such as chlorinated hydrocarbons, chlorinated oils and fats, and the like; organometallic extreme pressure agents such as thiophosphoric acid salts (e.g., zinc dithiophosphate (ZnDTP)) and thiocarbamic acid salts, and so on can be used.
  • phosphorus-based extreme pressure agents such as phosphoric acid esters, phosphorous acid esters, phosphoric acid ester amine salts,
  • Anti-wear agents which can be used include organomolybdenum compounds such as molybdenum dithiophosphate (MoDTP), molybdenum dithiocarbamate (MoDTC) and the like; organoboric compounds such as alkylmercaptyl borate and the like; solid lubricant-based anti-wear agents such as graphite, molybdenum disulfide, antimony sulfide, boron-containing compound, polytetrafluoroethylene and the like, and so on.
  • organomolybdenum compounds such as molybdenum dithiophosphate (MoDTP), molybdenum dithiocarbamate (MoDTC) and the like
  • organoboric compounds such as alkylmercaptyl borate and the like
  • solid lubricant-based anti-wear agents such as graphite, molybdenum disulfide, antimony sulfide, boron-containing compound, polytetraflu
  • oiliness agents which can be used include higher fatty acids such as oleic acid, stearic acid, and the like; higher alcohols such as oleyl alchol and the like; amines; esters; oils and fats and so on.
  • one or more agents selected from these extreme pressure agents, anti-wear agents and oiliness agents may be added in a suitable amount.
  • these agents are added in the range of 0.01 to 20 parts by weight based on 100 parts by weight of the base oil for the lubricating oil.
  • antioxidants various known additives including antioxidants, rust preventives, metal deactivators, viscosity index improvers, pour point depressors, deforming agents, etc. may further be effectively formulated depending on the purpose.
  • antioxidants various kinds thereof are included, for example, phenol-based antioxidants as exemplified by 2,6-di-t-butyl-p-cresol; amine-based antioxidants as exemplified by dioctyldiphenylamine; sulfur, phosphorus-based antioxidants such as zinc dithiophosphate; and so on.
  • rust preventives various compounds can be used.
  • carboxylic acids or esters or salts thereof as exemplified by alkylsuccinic acid, alkenylsuccinic acid and esters thereof, sulfonic acid salts as exemplified by calcium sulfonate, barium sulfonate, sodium sulfonate, alcohols, phosphoric acids or phosphoric acid salts, etc.
  • Metal deactivators may be those which have been employed conventionally and may include, for example, thiazole-based or dithiazole-based metal deactivators.
  • thiazole-based or dithiazole-based metal deactivators may include, for example, thiazole-based or dithiazole-based metal deactivators.
  • viscosity index improvers polymers such as polymethacrylate, etc. can suitably be used.
  • the lubricating oil composition of the present invention when used, fatigue damage of a metal is decreased and it shows good oxidation resistance. Further, it shows a high traction coefficient and also has excellent low temperature properties.
  • the lubricating composition of the present invention can be widely and effectively utilized as a lubricating oil for power transmission devices, particularly as a lubricating oil for gears, rolling bearings and traction drive mechanisms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)

Claims (11)

1. Schmierölzusammensetzung, welche ein Basisöl umfaßt von
(A) 100 bis 5 Gew.-% eines Mineralöls, das bei 40°C eine kinematische Viskosität von 2 bis 2000 mm²/s (cSt), einen Viskositätsindex von 70 oder höher, einen Stickstoffgehalt von 20 ppm oder weniger und einen Bromwert von 25 oder weniger hat, und
(B) 0 bis 95 Gew.-% eines Polybutens, mit einem Molekulargewicht von 200 bis 1000; und
wenigstens ein Additiv ausgewählt aus einem EP-Mittel, einem Anti-Verschleißmittel und einem Öligkeitsmittel.
2. Schmierölzusammensetzung nach Anspruch 1, worin genanntes Mineralöl einen Fließpunkt von  -20°C oder tiefer hat.
3. Schmierölzusammensetzung nach Anspruch 1, worin genanntes Mineralöl einen Fließpunkt von  -30°C oder tiefer hat.
4. Schmierölzusammensetzung nach Anspruch 1, worin genanntes Mineralöl bei 40°C eine kinematische Viskosität von 5 bis 1000 mm²/s (cSt) hat.
5. Schmierölzusammensetzung nach Anspruch 1, worin genanntes Mineralöl einen Viskositätsindex von 75 oder höher hat.
6. Schmierölzusammensetzung nach Anspruch 1, worin genanntes Mineralöl einen Stickstoffgehalt von 10 ppm oder weniger hat.
7. Schmierölzusammensetzung nach Anspruch 1, worin genanntes Mineralöl einen Bromwert von 10 oder weniger hat.
8. Schmierölzusammensetzung nach Anspruch 1, worin genanntes Polybuten ein Molekulargewicht von 300 bis 800 hat.
9. Schmierölzusammensetzung nach Anspruch 1, worin das Basisöl aus (A) 100 bis 20 Gew.-% des Mineralöls und (B) 0 bis 80 Gew.-% des Polybutens zusammengesetzt ist.
10. Schmierölzusammensetzung nach Anspruch 1, worin das Basisöl aus (A) 90 bis 20 Gew.-% des Mineralöls und (B) 10 bis 80 Gew.-% des Polybutens zusammengesetzt ist.
11. Schmierölzusammensetzung nach Anspruch 1, worin das Additiv in Bereich von 0,01 bis 20 Gewichtsteilen bezogen auf 100 Gewichtsteile des Basisöls hinzugefügt ist.
EP89108062A 1988-05-13 1989-05-04 Schmiermittelzusammensetzung Expired - Lifetime EP0341574B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP114739/88 1988-05-13
JP63114739A JP2608098B2 (ja) 1988-05-13 1988-05-13 潤滑油組成物

Publications (2)

Publication Number Publication Date
EP0341574A1 EP0341574A1 (de) 1989-11-15
EP0341574B1 true EP0341574B1 (de) 1991-10-30

Family

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Application Number Title Priority Date Filing Date
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Country Status (5)

Country Link
EP (1) EP0341574B1 (de)
JP (1) JP2608098B2 (de)
KR (1) KR950001712B1 (de)
CA (1) CA1311463C (de)
DE (1) DE68900373D1 (de)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2602102B2 (ja) * 1989-09-20 1997-04-23 日本石油株式会社 内燃機関用潤滑油組成物
FR2657088B1 (fr) * 1990-01-15 1994-04-15 Bp France Huile lubrifiante hydro-synthetique.
JP3259999B2 (ja) * 1993-01-25 2002-02-25 東燃ゼネラル石油株式会社 緩衝器用潤滑油
SG64414A1 (en) * 1996-01-16 1999-04-27 Lubrizol Corp Lubricating compositions
JP3811996B2 (ja) * 1996-07-10 2006-08-23 株式会社コスモ総合研究所 トラクションドライブ用流体
JP3873358B2 (ja) * 1997-03-19 2007-01-24 株式会社コスモ総合研究所 ギヤ油組成物
JPH10316987A (ja) * 1997-05-16 1998-12-02 Cosmo Sogo Kenkyusho:Kk ギヤ油組成物
JP3261340B2 (ja) * 1997-05-30 2002-02-25 東燃ゼネラル石油株式会社 潤滑油組成物
JP2003292984A (ja) * 2003-03-10 2003-10-15 Nsk Ltd 転がり軸受用潤滑剤組成物及び転がり軸受の製造方法
WO2005035700A1 (en) * 2003-10-10 2005-04-21 R.T. Vanderbilt Company, Inc. Lubricating compositions containing synthetic ester base oil, molybdenum compounds and thiadiazole-based compounds
US20050277560A1 (en) * 2004-06-09 2005-12-15 The Lubrizol Corporation Hydrocarbon compositions to reduce scuffing and seizure of the metal on metal interface for continuously variable transmissions
JP5584049B2 (ja) 2010-08-17 2014-09-03 株式会社Adeka 潤滑油用極圧剤及びそれを含有する潤滑油組成物
US8796189B2 (en) * 2011-10-14 2014-08-05 Chevron U.S.A. Inc. Gear lubricant
JP5822706B2 (ja) 2011-12-13 2015-11-24 株式会社Adeka 潤滑油用摩擦摩耗低減剤及びそれを含有する潤滑油組成物
KR101694622B1 (ko) * 2015-06-25 2017-01-09 에스케이이노베이션 주식회사 윤활기유 조성물
EP3425032B1 (de) * 2016-03-04 2021-01-27 Idemitsu Kosan Co., Ltd. Schmierölzusammensetzung

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US3838049A (en) * 1966-02-01 1974-09-24 G Souillard Lubricating compositions
FR1604121A (en) * 1966-02-01 1971-07-12 Two-stroke marine diesel lubricant containing liquid
US3912617A (en) * 1974-02-14 1975-10-14 Sun Oil Co Pennsylvania Blended refrigeration oil composition
JPS6144997A (ja) * 1984-08-09 1986-03-04 Nippon Steel Chem Co Ltd トラクシヨンオイルの製造方法
JPS61200199A (ja) * 1985-03-04 1986-09-04 Idemitsu Kosan Co Ltd 舶用機関ならし運転用潤滑油組成物
JP2555284B2 (ja) * 1987-05-14 1996-11-20 出光興産株式会社 温度特性改良潤滑油組成物

Also Published As

Publication number Publication date
JPH01287196A (ja) 1989-11-17
EP0341574A1 (de) 1989-11-15
CA1311463C (en) 1992-12-15
KR950001712B1 (ko) 1995-02-28
DE68900373D1 (de) 1991-12-05
KR900018346A (ko) 1990-12-21
JP2608098B2 (ja) 1997-05-07

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