EP0234923B1 - Improved lubricating oil composition - Google Patents
Improved lubricating oil composition Download PDFInfo
- Publication number
- EP0234923B1 EP0234923B1 EP87301610A EP87301610A EP0234923B1 EP 0234923 B1 EP0234923 B1 EP 0234923B1 EP 87301610 A EP87301610 A EP 87301610A EP 87301610 A EP87301610 A EP 87301610A EP 0234923 B1 EP0234923 B1 EP 0234923B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- metal
- basestock
- composition
- sulfide
- lubricating 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
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Classifications
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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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
- C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
- C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/28—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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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
- C10M2219/068—Thiocarbamate metal salts
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/088—Neutral salts
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
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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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/12—Groups 6 or 16
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/14—Group 7
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10
-
- 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
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Abstract
Description
- The present invention relates to a lubricating oil composition (herein also called lube oil composition) and more especially to one having a reduced phosphorus content while exhibiting satisfactory anti-wear and friction reducing properties.
- In currrent lube oil formulations for internal combustion engines, phosphorus-containing compounds such as zinc dialkyldithiophosphate (ZDDP), are added to the lube oil formulation to provide improved anti-wear properties. However, it has been found that phosphorus from phosphorus-containing compounds becomes deposited on the catalyst in catalytic converters, thereby decreasing the efficiency of catalytic converters over time. As a result, vehicle manufacturers have recommended that engine oil contain reduced phosphorus contents. At the present time automotive lube oils typically contain a maximum of about 0.10 to about 0.14 weight percent phosphorus. To reduce the rate at which catalytic converters become fouled by phosphorus, it would be advantageous to reduce the phosphorus content of the lube oils to about 0.08 weight percent, or lower.
- The use of dialkyldithiocarbamates in lube oils is known. U.S. Patent No. 4,178,258 discloses the use of zinc dialkyldithiophosphate (ZDDP) and a wear inhibiting amount of molybdenum bis(dialkydithiocarbamate). This patent also discloses the addition of sulfurized calcium phenates in the lube oil formulation. However, the addition of sulfurized calcium phenates to a lube oil is not desirable because it may reduce the fuel economy and anti-rust properties of the lube oil.
- U.S. Patent No. 3,513,094 also discloses the use of metal dithiocarbamates in lube oils. This patent discloses the use of the metal dithiocarbamates in combination with antimony dihydrocarbylphosphorodi- thioate. This patent also discloses the use of sulfurized sperm oil.
- U.S. Patent No. 3,923,669 discloses the use of zinc dialkyldithiophosphate and a neutral barium salt of a petroleum sulfonate diaryldithiocarbamate. The use of neutral barium salts of a petroleum sulfonate is not desirable because of the toxicity of barium.
- Japanese Patent Publication J54,113,604 discloses the combination of molybdenum sulfide-oxide, ZDDP and dialkydithiocarbamate in a lubricant for internal combustion engines.
- It is desirable to decrease the concentration of phosphate-containing compounds, such as zinc dialkyldithiophosphate, present in lubricating oil to thereby decrease the rate at which phosphates become deposited on the catalyst.
- It also is desirable to provide a lube oil having anti-wear and friction reducing properties comparable to presently available lube oils while also having a reduced phosphorus content.
- In accordance with the present invention, a lubricating oil composition having improved properties comprises:
- A. a major amount of a lubricating oil basestock; and minor amounts of
- B. a metal phosphate;
- C. a metal carbamate; and
- D. an alkyl hydroxy-aryl sulfide.
- The concentration of the metal phosphate, preferably a metal dithiophosphate (MDTP), may be limited to a range of about 0.1 or 0.2, to about 1.0, weight percent of the lube oil so that the concentration of phosphorus is less than about 0.08 weight percent, preferably 0.05 weight percent or less of the lube oil. The present invention also is directed at a method for improving the anti-wear properties of a lube oil basestock comprising the addition to the basestock of an effective amount of:
- A. a metal phosphate;
- B. a metal carbamate; and
- C. an alkyl hydroxy-aryl sulfide.
- In a preferred embodiment the metal salt is a metal dialkyldithiophosphate salt including a Group IB, IIB, VIB or VIIIB metal with zinc, nickel and copper being particularly preferred. The alkyl groups preferably comprise C3-C,o alkyls. The concentration of the metal dialkyldithiophosphate salt relative to the basestock ranges between about 0.1 and about 1.0 weight percent, preferably between about 0.3 and about 0.6 weight percent.
- The metal carbamate preferably comprises a metal dithiocarbamate wherein the metal is selected from Groups IB, IIB, VIB, VIIIB of the Periodic Table and mixtures thereof. Preferred metals include zinc, iron and nickel, with zinc being particularly preferred. The concentration of the metal dithiocarbamate may range between about 0.1 and about 1.3 weight percent, based upon the basestock content, preferably between about 0.2 and about 0.8 weight percent.
- The alkyl hydroxy-aryl sulfide preferably comprises an alkyl phenol sulfide where the alkyl group preferably ranges between about C6 and about C18 with a nonyl phenol sulfide being particularly preferred. The concentration of the alkyl hydroxy, aryl sulfide may range between about 0.2 and about 2.0 weight percent, based upon the basestock content, preferably between about 0.4 and about 0.8 weight percent.
- The Figure represents a plot to average cam lobe wear as a function of time for varying lube oil additive combinations.
- The basestock utilized in the present invention is not critical and may be selected to achieve the desired final properties of the lube oil. The basestock may be natural or synthetic or both.
- The metal phosphate of the present invention preferably comprises a metal dialkyldithiophosphate wherein the metal is selected from the group consisting of Group IB, IIB, VIB, VIIIB and mixtures thereof, with nickel, copper and zinc being particularly preferred. The alkyl groups preferably comprise C3C,o alkyls. Particularly preferred compounds are zinc dialkyldithiophosphates. These compounds and the methods for making the same are well-known by those skilled in the art. The concentration of the metal dialkyldithiophosphate may range between 0.1 and about 1.0 weight percent based upon the basestock content, preferably between about 0.3 and about 0.6 weight percent.
- The metal carbamate preferably comprises a metal dithiocarbamate where the metal preferably is selected from the group consisting of Group IB, IIB, VIIB and VIIB. Preferred metals include zinc, nickel and iron, with zinc dithiocarbamate being particularly preferred. The concentration of the metal carbamate may range between about 0.1 and about 1.3 weight percent, based upon the basestock content, preferably between about 0.2 and about 0.8 weight percent. The zinc dithiocarbamate (ZDTC) is readily available as an article of commerce.
- The alkyl hydroxy-aryl sulfide preferably comprises an alkyl phenol sulfide in which the alkyl groups preferably range between about Ca and C18. Nonyl phenol sulfide is a particularly preferred compound. The concentration of the alkyl hydroxy-aryl sulfide may range between about 0.2 and about 2.0 weight percent, based upon the basestock content, preferably between about 0.4 and about 0.8 weight percent. Nonyl phenol sulfide (NPS) is well-known by those skilled in the art and is readily obtainable as an article of commerce.
- The following comparative examples and examples demonstrate the utility of the present invention. The tests comprised valve train wear tests utilizing a Ford 2.3 liter engine with the pistons and connecting rods removed. The engine was driven with an 11.2 KW (15 horsepower) DC drive motor through a 1.2 timing belt drive. The engine was equipped Oldsmobile valve springs (146.5-148.3 KG) to increase the load between the cam lobes and the followers. Both oil and coolant circulation were accomplished by use of the engine mounted pumps. All test runs were made at 90°C oil temperature, 90°C coolant temperature, approximately 331 kPa oil pressure and an engine speed of 1,000 plus or minus 6 rpm.
- During operation, wear is generated on the lobes of the cam shaft and followers due to the sliding contact. As in the sequence V-D test described in ASTM Test No. STP 315H-Part 3, the disclosure of which is incorporated herein by reference, wear is defined as the reduction of the head-to-toe measurement at the point of maximum lift on the cam shaft. A pre-measured cam shaft is measured at various time intervals during the test to establish the reduction in the head-to-toe distance, i.e. the degree of wear. The tests were conducted with a commercially available lubricating oil from which the anti-wear additive had been removed and which were modified somewhat to simulate actual used oil conditions.
- In this test 0.41 weight percent of zinc dialkyldithiophosphate and 0.80 weight percent of zinc dithiocarbamate were added to the lube oil noted above. The engine was run for only 40 hours to prevent engine seizure due to high wear which had been detected after 20 hours of operation. The average cam lobe wear was 29.5 micrometers (µm) and 95.4 pm after 20 and 40 hours, respectively.
- A test similar to that described in Comparative Example 1 was run in which the lube oil contained 0.41 weight percent of ZDDP and 0.80 weight percent of nonyl phenol sulfide. Again, the test was run for 40 hours after which the cam lobe was measured. The average cam lobe wear was 36 um and 96.2 pm after 20 and 40 hours of testing, respectively.
- This Comparative Example was conducted similar to that of Comparative Example 1, but in this test 0.80 weight percent of zinc dithiocarbamate and 0.41 weight percent nonyl phenol sulfide were added to the lube oil. The average cam lube wear was 39.9 pm and 106 pm after 20 and 40, respectively.
- This test was conducted in a manner similar to that described hereinabove for the Comparative Examples. However, in this test the lube oil had added thereto all three of the above-noted additives, 0.41 weight percent zinc dialkyldithiophosphate, 0.30 weight percent zinc dithiocarbamate and 0.50 weight percent nonyl phenol sulfide. The average cam lobe wear was only 9.2 pm 10.6 pm, 11.6 µm and 11.6 um after 20, 40, 60 and 80 hours of testing, respectively.
- The data obtained in Comparative Examples 1-3 and in Example 1 are plotted on Figure 1. The average cam lobe wear in micrometers is plotted as a function of time. From a review of the data presented in Figure 1 and in Table 1 it can be seen that the combination of zinc dialkyldithiophosphate, zinc dithiocarbamate and nonyl phenol sulfide resulted in lower cam lobe wear than an equal weight of only two of the three additives.
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT87301610T ATE56221T1 (en) | 1986-02-24 | 1987-02-24 | LUBRICATION OIL COMPOSITION. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US83202186A | 1986-02-24 | 1986-02-24 | |
US832021 | 1986-02-24 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0234923A2 EP0234923A2 (en) | 1987-09-02 |
EP0234923A3 EP0234923A3 (en) | 1988-09-14 |
EP0234923B1 true EP0234923B1 (en) | 1990-09-05 |
Family
ID=25260452
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP87301610A Expired - Lifetime EP0234923B1 (en) | 1986-02-24 | 1987-02-24 | Improved lubricating oil composition |
Country Status (12)
Country | Link |
---|---|
EP (1) | EP0234923B1 (en) |
JP (1) | JPS62253691A (en) |
KR (1) | KR950006559B1 (en) |
AT (1) | ATE56221T1 (en) |
AU (1) | AU585699B2 (en) |
BR (1) | BR8700804A (en) |
CA (1) | CA1284489C (en) |
DE (1) | DE3764665D1 (en) |
ES (1) | ES2017713B3 (en) |
GR (1) | GR3001143T3 (en) |
HK (1) | HK24691A (en) |
MY (1) | MY100994A (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2915611B2 (en) * | 1991-04-01 | 1999-07-05 | 協同油脂株式会社 | Grease composition for constant velocity joints |
JP3086727B2 (en) * | 1991-08-09 | 2000-09-11 | オロナイトジャパン株式会社 | Additive composition for producing low phosphorus engine oil |
US7563752B2 (en) | 2002-08-05 | 2009-07-21 | Nippon Oil Corporation | Lubricating oil compositions |
US7625847B2 (en) | 2002-08-05 | 2009-12-01 | Nippon Oil Corporation | Lubricating oil compositions |
WO2004020557A1 (en) | 2002-08-27 | 2004-03-11 | Nippon Oil Corporation | Lubricating composition |
JP2004083746A (en) | 2002-08-27 | 2004-03-18 | Nippon Oil Corp | Lubricant oil composition for internal combustion engine |
JP4578115B2 (en) | 2004-02-04 | 2010-11-10 | Jx日鉱日石エネルギー株式会社 | Lubricating oil composition |
US7294684B2 (en) * | 2005-11-11 | 2007-11-13 | Dover Chemical Corporation | Dimeric and polymeric alkylphenol polysulfides |
CN112680266B (en) * | 2020-12-14 | 2022-10-04 | 常州龙邦润滑科技有限公司 | Flame-retardant hydraulic oil composition and preparation method thereof |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB801151A (en) * | 1955-01-27 | 1958-09-10 | Lubrizol Corp | Gear lubricant improving agents |
US3639240A (en) * | 1969-09-17 | 1972-02-01 | Atlas Chem Ind | Corrosion inhibitors for oil media |
FR2182652B2 (en) * | 1972-04-19 | 1979-01-12 | Telecommunications Sa | |
GB2056482A (en) * | 1979-08-13 | 1981-03-18 | Exxon Research Engineering Co | Lubricating oil compositions |
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1987
- 1987-02-13 CA CA000529695A patent/CA1284489C/en not_active Expired - Lifetime
- 1987-02-20 MY MYPI87000177A patent/MY100994A/en unknown
- 1987-02-20 BR BR8700804A patent/BR8700804A/en unknown
- 1987-02-23 AU AU69158/87A patent/AU585699B2/en not_active Ceased
- 1987-02-24 AT AT87301610T patent/ATE56221T1/en not_active IP Right Cessation
- 1987-02-24 KR KR1019870001542A patent/KR950006559B1/en active IP Right Grant
- 1987-02-24 EP EP87301610A patent/EP0234923B1/en not_active Expired - Lifetime
- 1987-02-24 ES ES87301610T patent/ES2017713B3/en not_active Expired - Lifetime
- 1987-02-24 JP JP62039315A patent/JPS62253691A/en active Pending
- 1987-02-24 DE DE8787301610T patent/DE3764665D1/en not_active Expired - Lifetime
-
1990
- 1990-11-30 GR GR90401007T patent/GR3001143T3/en unknown
-
1991
- 1991-04-04 HK HK246/91A patent/HK24691A/en unknown
Also Published As
Publication number | Publication date |
---|---|
AU6915887A (en) | 1987-08-27 |
AU585699B2 (en) | 1989-06-22 |
DE3764665D1 (en) | 1990-10-11 |
JPS62253691A (en) | 1987-11-05 |
KR870008012A (en) | 1987-09-23 |
EP0234923A3 (en) | 1988-09-14 |
CA1284489C (en) | 1991-05-28 |
GR3001143T3 (en) | 1992-06-25 |
EP0234923A2 (en) | 1987-09-02 |
BR8700804A (en) | 1987-12-15 |
MY100994A (en) | 1991-06-29 |
ES2017713B3 (en) | 1991-03-01 |
KR950006559B1 (en) | 1995-06-16 |
ATE56221T1 (en) | 1990-09-15 |
HK24691A (en) | 1991-04-12 |
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