WO2001085878A2 - Stabilising compositions for lubricating oils - Google Patents

Stabilising compositions for lubricating oils Download PDF

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Publication number
WO2001085878A2
WO2001085878A2 PCT/GB2001/002058 GB0102058W WO0185878A2 WO 2001085878 A2 WO2001085878 A2 WO 2001085878A2 GB 0102058 W GB0102058 W GB 0102058W WO 0185878 A2 WO0185878 A2 WO 0185878A2
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
alkyl
phosphite
neutral
phosphate
Prior art date
Application number
PCT/GB2001/002058
Other languages
English (en)
French (fr)
Other versions
WO2001085878A3 (en
Inventor
Alan Holt
Gerard Mulqueen
Original Assignee
Great Lakes Chemical (Europe) 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 Great Lakes Chemical (Europe) Gmbh filed Critical Great Lakes Chemical (Europe) Gmbh
Priority to US10/275,368 priority Critical patent/US20030171227A1/en
Priority to JP2001582468A priority patent/JP2004501234A/ja
Priority to AU52441/01A priority patent/AU5244101A/en
Priority to EP01925763A priority patent/EP1280872A2/en
Publication of WO2001085878A2 publication Critical patent/WO2001085878A2/en
Publication of WO2001085878A3 publication Critical patent/WO2001085878A3/en

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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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
    • 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
    • C10M129/12—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring with condensed rings
    • 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
    • C10M129/68—Esters
    • C10M129/76—Esters containing free hydroxy or carboxyl groups
    • 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
    • C10M133/04—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
    • 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
    • C10M135/20—Thiols; Sulfides; Polysulfides
    • C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M135/24—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
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    • C10M135/20—Thiols; Sulfides; Polysulfides
    • C10M135/28—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
    • C10M135/30—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups; Derivatives thereof
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    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
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    • 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
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
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    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
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    • C10M2207/28—Esters
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    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
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    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
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    • C10M2215/066—Arylene diamines
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    • C10M2215/067—Polyaryl amine alkanes
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    • C10M2215/068—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • C10N2040/20—Metal working
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol fueled engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • This invention relates to stabilising compositions for lubricant base stocks and lubricant formulations ⁇
  • lubricant base stocks such as mineral and synthetic base oils chosen from Group I, Group II, Group III, Group IV and Group V base stocks as classified by the American Petroleum Institute, as well as natural and synthetic esters including polyol esters, more particularly, but not limited to automotive oils, circulatory oils, gear oils, greases, hydraulic fluids, turbine fluids and metal working fluids.
  • lubricant formulations is meant a lubricant base stock as described above, plus additional additives including but not limited to antioxidants, rust inhibitors, metal passivators, ashless dispersants, antiwear additives, extreme pressure additives and detergents, viscosity index improvers and antifoam agents.
  • a stabilising composition for lubricant base stocks and lubricant compositions comprises :
  • R ⁇ and R 2 are the same or different and may be H, an alkyl group with 4 to 9 carbon atoms or an aralkyl group with 8 carbon atoms and m and n are 0 to 2 but m + n is not greater than 3, either alone or optionally blended with at least one hindered phenolic antioxidant selected from those corresponding to one of the following general formulae:
  • R 3 , R ⁇ R 5 and 5 are the same or different and may be an alkyl group with 1 to 4 carbon atoms and X is -S- or -CH 2 - or - CH 2 CH 2 -S-CH 2 CH 2 - or - -CH 2 -S-CH 2 - or -CH 2 CH 2 CO 2 CH 2 CH 2 -S-CH 2 CH CO 2 CH 2 CH 2 -
  • R 7 is an alkyl group with 6 to 20 carbon atoms
  • R 9 and Rw are the same or different and may be H, CH 3 , isopropyl or tertiary butyl and m is 0 to 2;
  • R ⁇ , R 12 and R 13 are all the same and are alkyl groups with 4 to 12 carbon atoms; (iii) neutral alkyl aryl phosphates:
  • R 1 is different from R 15 and R 16 and R 14 is an alkyl group with 4 to 12 carbon atoms and R 15 is phenyl or substituted phenyl with 7 to 10 carbon atoms and R 16 may be an alkyl group with 4 to 12 carbon atoms or phenyl or substituted phenyl with 7 to 10 carbon atoms;
  • R 1 is an alkyl group with 5 to 12 carbon atoms and m is 1 or 2 and n is 1 or 2 but m+n is not greater than 3; (v) neutral triaryl phosphites :
  • R 18 , R 1 , R20 are the same or different and are H or alkyl with 1 to 9 carbon atoms;
  • R 21 , R 2 2 and R 23 are the same or different and are alkyl groups with 1 to 18 carbon atoms.
  • R 24 and R 2 are the same or different and are alkyl groups with 1 to 12 carbon atoms or R 24 is phenyl or substituted phenyl where R 26 is alkyl with 1 to 9 carbon atoms.
  • R 2 may be an alkyl group with 4 to 18 carbon atoms, phenyl or substituted phenyl with 7 to 10 carbon atoms and m is 1 or 2, n is 1 or 2 but m + n is not greater than 3, and wherein the antioxidants and the phosphate(s) and/or phosphite(s) are utilised in a weight ratio from 10:1 to 1:10, preferably 1:1 to 1:5.
  • the stabilising composition is prepared by heating the antioxidant(s) and the phosphate(s) and/or phosphite(s) for 0.2 to 6 hours at a temperature range of 40°C to 150°C.
  • the treat rates of the antioxidant(s) and the phosphate(s) and/or phosphite(s) in the lubricant base stocks and lubricant compositions preferably are within the following weight ranges:
  • the amine and hindered phenol antioxidants are used at 0.5 to 2.0% each.
  • the neutral alkyl, aryl and alkyl aryl phosphates and phosphites are used at 0.5 to 4%.
  • the acid phosphates and phosphites at 0.025 to 0.05% (when used together with the neutral phosphates).
  • formula I compounds are 4-tert-butyl, 4'-tert-octyl diphenylamine; 4,4'- di-tert-octyl diphenyl amine and 4,4'-di-iso-nonyl diphenylamine.
  • formula II compounds are 4,4'-methylene bis (2,6 ditertiary butyl phenol); 2,2' thiodiethylene bis [3-(3,5-di-tert-butyl-4-hydroxy-phenyl) propionate]; 4,4'-thiobis (2-t-butyl-5-methyl phenol); 6,6'-thiobis (2-methyl-4-t-butylphenol).
  • Examples of formula III compounds are C 7 . alkyl ester of 3,5-di-tert-butyl-4-hydroxy benzene-3-propionic acid; C ⁇ e alkyl ester of 3,5-di-tert-butyl-4-hydroxybenzene-3- propionic acid.
  • An Example of formula IN compounds is pentaerythritol tetra ester of 3,5 di-tert-butyl- 4-hydroxy benzene-3-propionic acid.
  • Examples of formula N compounds are tri-dimethyl phenyl phosphate; tri-isopropyl phenyl phosphate; mono-phenyl-di (-tert-butyl phenyl) phosphate.
  • Examples of formula NI compounds are tributyl phosphate; trioctyl phosphate.
  • Examples of formula VII compounds are octyldiphenyl phosphate; dibutyl-mono-phenyl phosphate.
  • N ⁇ i compounds dipentyl hydrogen phosphate; di C 10 - 12 alkyl- hydrogen phosphate; C 10-1 2 alkyl-dihydrogen phosphate.
  • An Example of formula LX is tris nonyl phenyl phosphite.
  • Examples of formula X are trilauryl phosphite; trioctyl phosphite.
  • Examples of formula XI are decyl diphenyl phosphite; didecyl monophenyl phosphite.
  • Examples of formula XII are dibutyl hydrogen phosphite; dioctyl hydrogen phosphite; cetyl stearyl hydrogen phosphite.
  • lubricant base stocks and lubricant formulations can have varying levels of stability dependent on:
  • the Table shows the relative oxidation stability results obtained by adding certain antioxidant(s) and phosphate(s) and/or phosphite(s) mixtures to Group III base stocks.
  • the relative oxidation stabilities of the lubricant base stock is determined by the rotating bomb oxidation stability test (RBOT), IP test method number 229.
  • the oxidation stability is defined as the number of minutes required to effect a reduction in oxygen pressure of 25.4 PSI or 1.75 bar when the oil and additives are heated at 150°C in an oxygen pressurised vessel.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
PCT/GB2001/002058 2000-05-10 2001-05-10 Stabilising compositions for lubricating oils WO2001085878A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US10/275,368 US20030171227A1 (en) 2000-05-10 2001-05-10 Stabilizing compositions for lubricating oils
JP2001582468A JP2004501234A (ja) 2000-05-10 2001-05-10 潤滑油用安定剤組成物
AU52441/01A AU5244101A (en) 2000-05-10 2001-05-10 Stabilising compositions for lubricating oils
EP01925763A EP1280872A2 (en) 2000-05-10 2001-05-10 Stabilising compositions for lubricating oils

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0011189.8A GB0011189D0 (en) 2000-05-10 2000-05-10 Anti-oxidant additives
GB0011189.8 2000-05-10

Publications (2)

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WO2001085878A2 true WO2001085878A2 (en) 2001-11-15
WO2001085878A3 WO2001085878A3 (en) 2002-04-11

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US (1) US20030171227A1 (ja)
EP (1) EP1280872A2 (ja)
JP (1) JP2004501234A (ja)
AU (1) AU5244101A (ja)
GB (1) GB0011189D0 (ja)
WO (1) WO2001085878A2 (ja)

Cited By (3)

* Cited by examiner, † Cited by third party
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EP1674556A3 (en) * 2004-12-21 2007-12-19 Chevron Oronite Company LLC An anti-wear additive composition and lubricating oil composition comprising the same
EP1471133A3 (en) * 2003-04-25 2007-12-26 Chevron Oronite Company LLC Gear oil having low copper corrosion properties
EP3778832A4 (en) * 2018-03-30 2022-01-05 Idemitsu Kosan Co.,Ltd. LUBRICATING OIL COMPOSITION

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DE102004039183B4 (de) * 2004-08-12 2009-11-05 Schill + Seilacher Ag Trägerflüssigkeit für Wirkstoffkonzentrate und deren Verwendung
US7799101B2 (en) * 2004-09-29 2010-09-21 Chemtura Corporation Stabilized lubricant compositions
ATE484698T1 (de) * 2005-12-02 2010-10-15 United Technologies Corp Zahnrad mit verbesserter oberflächengüte
US20070232505A1 (en) * 2006-03-31 2007-10-04 Marc-Andre Poirier Method for reducing deposit formation in lubricant compositions
CN101679895B (zh) * 2007-04-25 2013-10-02 陶氏环球技术有限责任公司 润滑剂共混物组合物
US8049041B2 (en) * 2008-06-27 2011-11-01 Chemtura Corporation Phosphite stabilizer for lubricating base stocks and thermoplastic polymers
JP5730283B2 (ja) * 2010-03-26 2015-06-10 株式会社Adeka 潤滑油組成物
CN103045324A (zh) * 2011-10-17 2013-04-17 中国石油天然气股份有限公司 一种可用于金属加工油中的极压抗磨添加剂
CN103184090A (zh) * 2011-12-30 2013-07-03 中国石油天然气股份有限公司 一种螺杆空气压缩机油组合物
JP7444644B2 (ja) * 2020-03-06 2024-03-06 出光興産株式会社 潤滑油組成物、及び潤滑油組成物の使用方法

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US5167844A (en) * 1989-11-08 1992-12-01 Ciba-Geigy Corporation Lubricant formulations
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EP1471133A3 (en) * 2003-04-25 2007-12-26 Chevron Oronite Company LLC Gear oil having low copper corrosion properties
US7871965B2 (en) 2003-04-25 2011-01-18 Chevron Oronite Company Llc Gear oil having low copper corrosion properties
US8389449B2 (en) 2003-04-25 2013-03-05 Chevron Oronite Company Llc Gear oil having low copper corrosion properties
US8536102B2 (en) 2003-04-25 2013-09-17 Chevron Oronite Company Llc Gear oil having low copper corrosion properties
EP1674556A3 (en) * 2004-12-21 2007-12-19 Chevron Oronite Company LLC An anti-wear additive composition and lubricating oil composition comprising the same
US7786059B2 (en) 2004-12-21 2010-08-31 Chevron Oronite Company Llc Anti-wear additive composition and lubricating oil composition containing the same
EP3778832A4 (en) * 2018-03-30 2022-01-05 Idemitsu Kosan Co.,Ltd. LUBRICATING OIL COMPOSITION
US11274264B2 (en) 2018-03-30 2022-03-15 Idemitsu Kosan Co., Ltd. Lubricating oil composition

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US20030171227A1 (en) 2003-09-11
GB0011189D0 (en) 2000-06-28
EP1280872A2 (en) 2003-02-05
WO2001085878A3 (en) 2002-04-11
JP2004501234A (ja) 2004-01-15
AU5244101A (en) 2001-11-20

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