EP0757712B1 - Composition de lubrifiant - Google Patents

Composition de lubrifiant Download PDF

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Publication number
EP0757712B1
EP0757712B1 EP95916764A EP95916764A EP0757712B1 EP 0757712 B1 EP0757712 B1 EP 0757712B1 EP 95916764 A EP95916764 A EP 95916764A EP 95916764 A EP95916764 A EP 95916764A EP 0757712 B1 EP0757712 B1 EP 0757712B1
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EP
European Patent Office
Prior art keywords
lubricant composition
component
composition according
alkyl
weight
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
EP95916764A
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German (de)
English (en)
Other versions
EP0757712A1 (fr
Inventor
Andrew Jonathan Markson
John William Anthony Pragnell
Mark Anthony Edwards
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.)
Castrol Ltd
Original Assignee
Castrol Ltd
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    • 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
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • 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
    • 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
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • 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
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/30—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms
    • C10M129/32—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms monocarboxylic
    • 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
    • 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
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/30—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms
    • C10M129/34—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms polycarboxylic
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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    • 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
    • C10M129/26—Carboxylic acids; Salts thereof
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    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/40—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms monocarboxylic
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    • 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
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    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/42—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms polycarboxylic
    • C—CHEMISTRY; METALLURGY
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    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
    • C10M129/52—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring polycarboxylic
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    • C10M129/68—Esters
    • C10M129/70—Esters of monocarboxylic acids
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    • 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
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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    • 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
    • C10M133/30—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms containing a nitrogen-to-oxygen bond
    • C10M133/32—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms containing a nitrogen-to-oxygen bond containing a nitro group
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M133/40—Six-membered ring containing nitrogen and carbon only
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    • C10M133/44—Five-membered ring containing nitrogen and carbon only
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised compounds
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    • C10M137/08—Ammonium or amine salts
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings

Definitions

  • This invention relates to a lubricant composition and is particularly concerned with a transmission lubricant suitable, for example, for helicopter transmission systems.
  • DE-A-2039785 discloses a load carrying additive composition for a gas turbine engine.
  • the load carrying additive composition comprises a synthetic ester base stock fluid having a viscosity of 5.6 to 6.0 cs. at 99 °C (210 °F) (see the examples).
  • US-A-3694382 discloses a lubricant for a gas turbine engine.
  • the lubricant comprises a synthetic ester base stock having a viscosity ranging from 4.0 to 9.1 cs. at 99 °C (210 °F).
  • FR-A-2215462 discloses a lubricant having a mineral oil as its base stock.
  • WO-A-9410270 discloses a corrosion inhibiting lubricating composition
  • a corrosion inhibiting lubricating composition comprising a synthetic base stock having a viscosity of at least 4.9 cSt at 100 °C.
  • the present invention provides a lubricant composition
  • a lubricant composition comprising:
  • At least one base stock of the base component is preferably a synthetic ester base stock, especially a polyol ester base stock.
  • the synthetic polyolester which preferably forms a base stock of the lubricating composition of the present invention may be made from C 5 to C 12 monocarboxylic acids esterified with polyols or polyol ethers such as neopentylglycol, dimethylolpropane, trimethylolpropane, pentaerythritol or dipentaerythritol. These are conventional synthetic ester base stocks.
  • Preferred esters are those which are described in U.S. Patent 4826633.
  • the viscosity may be adjusted to lie within the required range by inclusion of one or more viscosity index improvers.
  • the base component must have a viscosity in the range of 8.5 to 9.5 cSt, preferably 8.75 to 9.25 mm 2 /s (cSt), at 100°C.
  • the base component may comprise a single polyol ester but is more usually a mixture of polyol esters, for example, a mixture of a polyol ester having a viscosity of about 4.0 cSt at 100°C with a polyol ester having a viscosity of about 12.0 mm 2 /s (cSt) at 100°C.
  • Preferred synthetic polyol esters are reaction products of pentaerythritol and/or trimethylolpropane and an acid mixture comprising C 5 to C 10 straight and branched chain acids.
  • the antioxidant component b) may be a hindered phenolic antioxidant such as butylated hydroxytoluene, suitably present in an amount of 0.01 to 5%, preferably 0.4 to 0.8%, by weight of the lubricant composition.
  • component b) may comprise an aromatic amine antioxidant such as mono-octylphenylalphanapthylamine or p,p-dioctyldiphenylamine, used singly or in admixture.
  • the amine anti-oxidant component is suitably present in a range of from 0.01 to 5% by weight of the lubricant composition, more preferably 0.5 to 1.5%.
  • the neutral organic phosphate which forms component c) of the formulation is present in an amount of 1.5 to 2.5% by weight of the composition.
  • the neutral organic phosphate is also a conventional ingredient of lubricating compositions and any such neutral organic phosphate falling within the formula as previously defined may be employed.
  • Tri-cresyl phosphate is a preferred phosphate for use in the present invention.
  • Components d), e) and f) are intended to provide a corrosion inhibiting three component system.
  • the combination has been found to enable the provision of lubricant compositions capable of passing United States Navy corrosion inhibition requirements (Ball Corrosion Test - ARP 4249) in which a result of 50% non corroded specimen is deemed a satisfactory corrosion protection requirement.
  • the dicarboxylic acid forming the first component of the anti-corrosion combination may be any dicarboxylic acid falling within the definition given hereinbefore.
  • the dicarboxylic acid may be present in a proportion of up to 0.15% by weight of the composition. It should be noted however, that it is desirable that sebacic acid or an equivalent thereof should always be present in the composition even if another dicarboxylic acid falling within the above definition is present because sebacic acid or an equivalent of it may be necessary to meet parts of the specification other than the ball corrosion test, for example, for satisfactory lead corrosion resistance.
  • dibasic acids other than sebacic acids, which may be used in the present invention, are adipic acid, azelaic acid, dodecanedioic acid, 3-methyladipic acid, 3-nitrophthalic acid, 1,10-decanedicarboxylic acid, and fumaric acid.
  • the second component of the anti-corrosion combination is a straight or branch-chained, saturated or unsaturated monocarboxylic acid or ester thereof which may optionally be sulphurised in an amount up to 35% by weight.
  • the acid is a C 4 to C 22 straight chain unsaturated monocarboxylic acid.
  • the preferred concentration of this additive is from 0.001% to 0.35% by weight of the total lubricant composition.
  • the preferred monocarboxylic acid is sulphurised oleic acid.
  • other suitable materials are oleic acid itself; valeric acid and erucic acid.
  • the third component of the anti-corrosion combination is a triazole as previously defined.
  • the triazole should be used at a concentration from 0.005% to 0.25% by weight of the total composition.
  • the preferred triazole is benzotriazole.
  • Component g) of the composition comprises at least one phosphorus containing extreme pressure additive.
  • additives are amine phosphate extreme pressure additives such as that known under the trade name IRGALUBE® 349 and/or triphenyl phosphorothionate extreme pressure/anti-wear additives such as that known under the trade name IRGALUBE® TPPT .
  • Such amine phosphates are suitably present in an amount of from 0.01 to 2%, preferably 0.2 to 0.6% by weight of the lubricant composition while such phosphorothionates are suitably present in an amount of from 0.01 to 3%, preferably 0.5 to 1.5% by weight of the lubricant composition.
  • a mixture of an amine phosphate and phosphorothionate is employed.
  • the amounts of the additive are selected so as to comply with the United States Navy requirement for the Ryder gear test, conducted at 100°C, (average of 6 runs) of 200 (relative rating, % Herco® A as reference fluid).
  • the resulting composition was found to give a value of 204.7 in the Ryder gear test, 100°C (as relative rating, % Herco® A) and pass rating in the Ball Corrosion Test (in accordance with ARP method 4249).

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  • General Chemical & Material Sciences (AREA)
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  • Emergency Medicine (AREA)
  • Lubricants (AREA)

Claims (15)

  1. Composition de lubrifiant comprenant :
    a) un composant de base comprenant un ou plusieurs matériaux de base synthétiques, lequel composant de base présente une viscosité située dans l'intervalle allant de 8,5 à 9,5 mm2/s (cSt) à 100°C ;
    b) au moins un antioxydant choisi parmi les amines aromatiques et les composés phénoliques stériquement encombrés ;
    c) au moins un phosphate organique neutre de formule (R1O)3PO dans laquelle R1 représente un groupe tolyle, phényle, xylyle, alkyle ou cycloalkyle, le groupe alkyle ou cycloalkyle comportant jusqu'à 10 atomes de carbone ; le phosphate organique neutre étant présent en une quantité de 1,5 à 2,5% en poids de la composition,
    d) au moins un acide dicarboxylique saturé et/ou insaturé de formule générale
    Figure 00190001
    dans laquelle x+y+z représente un nombre entier dans l'intervalle allant de 2 à 22, bornes incluses, et dans laquelle au moins l'un des groupes R1 à R5 est un groupe acide carboxylique et les groupes R1 à R5 restants sont choisis parmi alkyle, hydroxy, nitro, amino, carboxyle, hydrogène, ou des dérivés alkylés de ceux-ci, le groupe alkyle étant une chaíne courte comportant jusqu'à 5 atomes de carbone ; et/ou un acide dicarboxylique répondant à l'une des trois formules
    Figure 00200001
    dans lesquelles R'1 représente -COOH, alkyle, hydroxy, nitro, amino, hydrogène, ou des dérivés alkylés de ceux-ci ; R'2 représente -COOH ; et n représente un nombre entier de 1 à 4, bornes incluses, lorsque R'1 représente -COOH, ou un nombre entier de 2 à 4, bornes incluses, lorsque R'1 ne représente pas -COOH,
    e) au moins un acide monocarboxylique saturé ou insaturé à chaíne linéaire et/ou ramifiée qui est facultativement sulfuré en une quantité qui peut aller jusqu'à 35% en poids ; et/ou un ester de cet acide ; et
    f) au moins un triazole de formule :
    Figure 00200002
    dans laquelle R''1 représente -COOH ou des dérivés alkylés de celui-ci, ou un alkyle à chaíne courte comportant jusqu'à 5 atomes de carbone ; n représente zéro ou un nombre entier entre 1 et 3, bornes incluses ; et R''2 représente hydrogène, morpholino, alkyle, amido, amino, hydroxy ou des dérivés alkyl- ou aryl-substitués de ceux-ci ; ou un triazole choisi parmi le 1,2,4-triazole, le 1,2,3-triazole, le 5-anilo-1,2,3,4-thiatriazole, le 3-amino-1,2,4-triazole, le 1-H-benzotriazole-1-yl-méthylisocyanure, le méthylène-bis-benzotriazole et le naphtotriazole ; et
    g) au moins un additif extrême-pression contenant du phosphore.
    dans laquelle les composants (b) à (g) sont présents dans des quantités choisies de manière à satisfaire à l'exigence de la United States Navy (Marine des Etats-Unis d'Amérique) pour l'essai Ryder effectué à 100°C, de 200 (classement relatif, % Herco® A comme fluide de référence).
  2. Composition lubrifiante selon la revendication 1, dans laquelle au moins un matériau de base du composant de base est un ester de polyol.
  3. Composition lubrifiante selon la revendication 2, dans laquelle le matériau de base de type ester de polyol comprend un ou plusieurs acides monocarboxyliques en C5 à C12 estérifiés avec un ou plusieurs polyols ou éthers de polyols.
  4. Composition lubrifiante selon l'une quelconque des revendications 1 à 3, dans laquelle le composant de base présente une viscosité située dans la gamme allant de 8,75 à 9,25 mm2/s (cSt) à 100°C.
  5. Composition lubrifiante selon l'une quelconque des revendications précédentes dans laquelle l'antioxydant comprend un antioxydant phénolique stériquement encombré présent en une quantité de 0,4 à 0,8% en poids de la composition.
  6. Composition lubrifiante selon l'une quelconque des revendications précédentes dans laquelle l'antioxydant comprend un antioxydant de type amine aromatique présent en une quantité de 0,5 à 1,5% en poids de la composition.
  7. Composition lubrifiante selon l'une quelconque des revendications précédentes, dans laquelle le composant acide dicarboxylique saturé et/ou insaturé (d) est présent en une quantité allant jusqu'à 0,15% en poids de la composition.
  8. Composition lubrifiante selon l'une quelconque des revendications précédentes dans laquelle le composant acide dicarboxylique saturé et/ou insaturé (d) comprend de l'acide sébacique.
  9. Composition lubrifiante selon l'une quelconque des revendications précédentes dans laquelle le composant acide monocarboxylique (e) est présent en une quantité de 0,001 à 0,35% en poids de la composition.
  10. Composition lubrifiante selon l'une quelconque des revendications précédentes, dans laquelle le composant acide monocarboxylique (e) comprend de l'acide oléique sulfuré.
  11. Composition lubrifiante selon l'une quelconque des revendications précédentes, dans laquelle le composant triazole (f) est présent en une quantité de 0,005 à 0,25% en poids de la composition.
  12. Composition lubrifiante selon l'une quelconque des revendications précédentes, dans laquelle le composant triazole (f) comprend du benzotriazole.
  13. Composition lubrifiante selon l'une quelconque des revendications précédentes, dans laquelle le composant additif extrême-pression (g) comprend un additif extrême-pression phosphate d'amine présent en une quantité de 0,2 à 0,6% en poids de la composition.
  14. Composition lubrifiante selon l'une quelconque des revendications précédentes dans laquelle le composant additif extrême-pression (g) comprend un additif extrême-pression phosphorothionate présent en une quantité de 0,5 à 1,5% en poids de la composition.
  15. Lubrifiant de transmission pour hélicoptère comprenant les composants (a) à (g) tels que définis dans l'une quelconque des revendications précédentes.
EP95916764A 1994-04-26 1995-04-25 Composition de lubrifiant Expired - Lifetime EP0757712B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9408235A GB9408235D0 (en) 1994-04-26 1994-04-26 Lubricant composition
GB9408235 1994-04-26
PCT/GB1995/000941 WO1995029214A1 (fr) 1994-04-26 1995-04-25 Composition de lubrifiant

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EP0757712A1 EP0757712A1 (fr) 1997-02-12
EP0757712B1 true EP0757712B1 (fr) 2000-03-22

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JP (1) JP3780323B2 (fr)
KR (1) KR100339777B1 (fr)
CN (1) CN1043053C (fr)
AT (1) ATE190997T1 (fr)
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DE (1) DE69515861T2 (fr)
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US6043199A (en) * 1997-08-26 2000-03-28 Exxon Research And Engineering Co. Corrosion inhibiting additive combination for turbine oils
US5955403A (en) * 1998-03-24 1999-09-21 Exxon Research And Engineering Company Sulphur-free, PAO-base lubricants with excellent anti-wear properties and superior thermal/oxidation stability
JP2000169871A (ja) * 1998-12-08 2000-06-20 Nippon Mitsubishi Oil Corp 潤滑油組成物
US6074992A (en) * 1999-02-02 2000-06-13 Union Carbide Chemicals & Plastics Technology Corporation Functional fluid compositions
CN1218024C (zh) * 2000-02-09 2005-09-07 西铁城钟表股份有限公司 润滑油组合物及使用该组合物的手表
US6573223B1 (en) * 2002-03-04 2003-06-03 The Lubrizol Corporation Lubricating compositions with good thermal stability and demulsibility properties
GB0226726D0 (en) * 2002-11-15 2002-12-24 Bp Oil Int Method
US7648948B2 (en) 2005-04-08 2010-01-19 Exxonmobil Chemical Patents Inc. Additive system for lubricants
US20080139427A1 (en) * 2006-12-11 2008-06-12 Hutchison David A Lubricating composition
JP5827782B2 (ja) 2009-05-08 2015-12-02 出光興産株式会社 生分解性潤滑油組成物
JP6669343B2 (ja) * 2015-02-27 2020-03-18 出光興産株式会社 生分解性潤滑油組成物
CN106590869A (zh) * 2016-11-28 2017-04-26 广西大学 一种全合成四连杆摆块机构热气机润滑剂组合物

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FR2051665A1 (fr) * 1969-07-10 1971-04-09 Ethyl Corp
BE754710A (fr) * 1969-08-12 1971-02-11 Stauffer Chemical Co Composition de lubrifiant synthetique
FR2215462A1 (fr) * 1973-01-25 1974-08-23 Exxon Research Engineering Co
CN1030934A (zh) * 1987-07-30 1989-02-08 钱江宁 高速车制动液及其生产方法
US4981602A (en) * 1988-06-13 1991-01-01 The Lubrizol Corporation Lubricating oil compositions and concentrates
CN1070679A (zh) * 1991-09-17 1993-04-07 岳江 合成刹车油及其制法
GB2272000B (en) * 1992-10-30 1997-03-26 Castrol Ltd A method of inhibiting corrosion

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CA2188936A1 (fr) 1995-11-02
CN1151174A (zh) 1997-06-04
ES2148513T3 (es) 2000-10-16
CN1043053C (zh) 1999-04-21
WO1995029214A1 (fr) 1995-11-02
EP0757712A1 (fr) 1997-02-12
DE69515861D1 (de) 2000-04-27
GR3033741T3 (en) 2000-10-31
KR100339777B1 (ko) 2002-11-13
AU695511B2 (en) 1998-08-13
JP3780323B2 (ja) 2006-05-31
NZ284520A (en) 1997-09-22
JPH10503535A (ja) 1998-03-31
AU2313595A (en) 1995-11-16
DK0757712T3 (da) 2000-08-28
GB9408235D0 (en) 1994-06-15
ATE190997T1 (de) 2000-04-15
PT757712E (pt) 2000-09-29
DE69515861T2 (de) 2000-12-07

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