WO1996020265A1 - Overbased alkyl oxy benzene sulfonates as detergents - Google Patents
Overbased alkyl oxy benzene sulfonates as detergents Download PDFInfo
- Publication number
- WO1996020265A1 WO1996020265A1 PCT/US1995/016162 US9516162W WO9620265A1 WO 1996020265 A1 WO1996020265 A1 WO 1996020265A1 US 9516162 W US9516162 W US 9516162W WO 9620265 A1 WO9620265 A1 WO 9620265A1
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- WIPO (PCT)
- Prior art keywords
- alkyl
- oxy benzene
- overbased
- alkyl oxy
- sulfonate
- Prior art date
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- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/28—Rotary engines
Definitions
- the present invention relates to an additive especially useful in a marine lubricating oil.
- British 1 ,372,532 teaches that mixtures of overbased, alkyl hydroxy benzene sulfonates and alkylsalicylic acids are useful in lubricating oils.
- the alkyl groups of the sulfonates appear to be attached at either the .- op ⁇ position of the alkyl groups.
- the TBN appears to be about 200.
- British 1 ,332,473 teaches that overbased, alkyl hydroxy benzene sulfonates are useful as an oil-soluble dispersant in lubricating oils.
- the patent is silent as to where the alkyl groups are attached.
- the TBN appears to be about 400, with a very high base ratio.
- U.S. 4,751 ,010 teaches that partial sulfonation of alkylphenol results in the formation of an alkyl hydroxy benzene sulfonate that can be overbased using sulfurization and carbonation.
- the patent is silent as to where the alkyl groups are attached.
- the TBN appears to be in the range of from 200 to 250.
- U.S. 5,330,663 and 5,330,664 teach overbased alkylphenoxy sulfonates that have alkyl groups derived from substantially straight-chained olefins that are either internal or alpha. It does not teach using olefins that are partially internal olefins.
- the present invention provides a lubricating oil having a major amount of base oil of lubricating viscosity, and a minor amount of an overbased, alkyl oxy benzene sulfonate having a TBN of at least 200, preferably at least 250, between 40 wt % and 80 wt % of the alkyl group is attached at the 4- position and higher positions of the alkyl group Preferably, between 45 wt % and 70 wt % of the alkyl group is attached at the 4- position and higher positions of the alkyl group
- This lubricating oil is especially useful as a marine lubricating oil
- the oxy group can be either hydroxy, methoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy Preferably, it is hydroxy
- the alkyl group of the overbased, alkyl oxy benzene sulfonate has from eighteen to thirty carbon atoms per alkyl group More preferably, it has from twenty to twenty-four carbon atoms per alkyl group
- One process for making this overbased, alkyl oxy benzene sulfonate comprises alkylating an oxy benzene with an olefin between 40 wt % and 80 wt % internal olefins to produce an alkyl oxy benzene, then sulfonating the alkyl oxy benzene to produce an alkyl oxy benzene sulfonic acid, and overbasing the alkyl oxy benzene sulfonic acid to produce the overbased, alkyl oxy benzene sulfonate
- the internal olefin is produced by isome ⁇ zing an olefin using an iron pentacarbonyl catalyst
- an additive is produced by alkylating an oxy benzene with a polyalpha olefin having an activity of at least 80% to produce an alkyl oxy benzene, sulfonating the alkyl oxy benzene to produce an alkyl oxy benzene sulfonic acid, and overbasing the alkyl oxy benzene sulfonic acid to produce an overbased, alkyl oxy benzene sulfonate having a TBN of at least 200, preferably at least 250
- the present invention involves highly overbased, alkyl oxy benzene sulfonate detergents where at least 40 wt % of the alkyl groups are attached at the 4- position and higher positions of the alkyl group.
- the viscosity is lowered significantly.
- At least 20 wt.% of the alkyl groups should be attached at the 1-, 2-, and 3- position in order to reduce high temperature deposit formation. While Applicants do not wish to be bound by any particular theory of operation, it is believed that too high of internal attachment leads to structures that are similar to materials derived from branched olefins. Such materials tend to decompose readily at the branching.
- between 40 wt.% and 80 wt. % (preferably between 45 wt.% and 70 wt. %) of the alkyl group is attached at the 4- position and higher positions of the alkyl group.
- This type of additive can be produced by alkylating an oxy benzene with an olefin containing between between 40 wt.% and 80 wt.
- An olefin containing between 20 wt.% and 60 wt. % internal olefins can be formed by isomerizing an alpha olefin using an iron pentacarbonyl catalyst.
- the additive is produced by alkylating an oxy benzene with a polyalpha olefin having an activity of at least 80% to produce an alkyl oxy benzene, sulfonating the alkyl oxy benzene to produce an alkyl oxy benzene sulfonic acid; and overbasing the alkyl oxy benzene sulfonic acid to produce an overbased, alkyl oxy benzene sulfonate having a TBN of at least 250.
- the present invention comes out of work in trying to find an inexpensive alternative to the use of salicylates in lube oils for marine applications. That alternative should have a TBN of over 250, have a viscosity of less than 600 cSt, and have comparative properties with commercial salicylates.
- the lubricating oil has a minor amount of an overbased, alkyl oxy benzene sulfonate having a TBN of at least 200, preferably at least 250, wherein at least 40 wt.% of the alkyl group of the sulfonate is attached at the 4- position and higher positions of the alkyl group.
- the oxy group can be either hydroxy, methoxy, ethoxy, propoxy, butoxy, pentoxy, or hexoxy. Preferably, it is hydroxy.
- TBN Total Base Number
- Total Base Number refers to the amount of base equivalent to one milligram of KOH in one gram of additive.
- internal olefins we mean an olefin wherein the double bond is at the 4- position and higher positions of the alkene, instead of at the 1-, 2-, or
- the alkyl group of the overbased, alkyl oxy benzene sulfonate has from eighteen to thirty carbon atoms per alkyl group. More preferably, the alkyl group has from twenty to twenty-four carbon atoms per alkyl group.
- the additive of the present invention can be produced by alkylating an oxy benzene with an olefin containing between 40 wt.% and 80 wt. % internal olefins to produce an alkyl oxy benzene, sulfonating the alkyl oxy benzene to produce an alkyl oxy benzene sulfonic acid; and overbasing the alkyl oxy benzene sulfonic acid to produce the overbased, alkyl oxy benzene sulfonate.
- An olefin containing between 40 wt.% and 80 wt. % internal olefins can be formed by isome zing an alpha olefin using an iron pentacarbonyl catalyst.
- a neutralized slurry of alkyl oxy benzene sulfonic acid is added to a slurry of xylenes, methanol, and calcium hydroxide.
- the resulting slurry is then carbonated during which a second slurry of alkyl oxy benzene sulfonic acid and a second slurry of xylenes, methanol, and calcium hydroxide are added.
- the material is stripped to remove methanol and water.
- Lube oil is then added and the solids removed. The remainder of the solvents are then stripped off and additional lube oil added to adjust the product to the final base number.
- the oil-soluble, highly overbased, alkyl oxy benzene sulfonate additive compositions produced by the process of this invention are useful lubricating oil additives imparting detergency and dispersency properties when added to the lubricating oil composition employed in the crank case of an internal combustion engine.
- Such lubricating oil compositions comprise a major amount of base oil of lubricating viscosity; and a minor amount of oil-soluble, highly overbased, alkyl oxy benzene sulfonate additive compositions.
- These lubricating oil compositions are useful in diesel engines, gasoline engines, as well as in marine engines.
- Such lubricating oil compositions employ a finished lubricating base oil oil of lubricating viscosity which may be single or multigrade. Multigrade lubricating base oils are prepared by adding viscosity index (VI) improvers.
- VI viscosity index
- Typical viscosity index improvers are polyalkyl methacrylates, ethylene and propylene copolymers, styrene-diene copolymers, and the like.
- the lubricating base oils used in such compositions may be mineral oils or synthetic oils of viscosity suitable for use in the crank case of an internal combustion engine such as gasoline engines and diesel engines which include marine engines. Crank case lubricating oils ordinarily have a viscosity of about 1300 cSt at 0° F to 24 cSt at 210° F (99° C).
- the lubricating base oils may be derived from synthetic or natural sources.
- Mineral oils for use as the base oil in the invention includes paraffinic, naphthenic and other oils that are ordinarily used in lubricating oil compositions.
- Synthetic oils include both hydrocarbon synthetic oils and synthetic esters. Useful synthetic hydrocarbon oils include liquid polymers of ⁇ -olefins having the proper viscosity.
- the hydrogenated liquid oligomers of C 6 to C, 2 ⁇ -olefins such as 1-decene trimer.
- alkylbenzenes of proper viscosity such as didodecyl benzene
- useful synthetic esters include esters of both monocarboxylic acids and polycarboxylic acids as well as monohydroxy alkenols and polyols. Typical examples are didodecyl adipate, pentaerythritol tetracaproate, di-2-ethylhexyl adipate, dilaurylsebacate and the like.
- Complex esters prepared from mixtures of mono and dicarboxylic acid and mono and dihydroxy alkanols can also be used,
- Blends of hydrocarbon oils with synthetic oils are also useful. For example, blends of 10 to 25 wt. % hydrogenated 1 -decene trimer with 75 to 90 wt. % 150 SUS (100° F) mineral oil gives an excellent lubricating base oil.
- the lubricating oil also has an ashless dispersant and a zinc dialkyldithiophosphate.
- the lubricating oil also has a detergent selected from the group consisting of metal phenates, metal sulfonates, and metal salicylates.
- a detergent selected from the group consisting of metal phenates, metal sulfonates, and metal salicylates.
- Other additives which may be present in the formulation include rust inhibitors, foam inhibitors, corrosion inhibitors, metal deactivators, pour point depressants, anti-oxidants, and a variety of other well-known additives
- Phenol type phenolic) oxidation inhibitors 4,4'-methylenebis (2,6-di-tert-butylphenol), 4,4'-bis(2,6-di-tert-butylphenol),
- Diphenylamine type oxidation inhibitor alkylated diphenylamine, phenyl- ⁇ -naphthylamine, and alkylated ⁇ - naphthylamine.
- metal dithiocarbamate e.g., zinc dithiocarbamate
- methylenebis dibutyldithiocarbamate
- Nonionic polyoxyethylene surface active agents polyoxyethylene lauryl ether, polyoxyethylene higher alcohol ether, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene octyl stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene sorbitol monostearate, polyoxyethylene sorbitol mono-oleate, and polyethylene glycol monooleate.
- Demulsifiers addition product of alkylphenol and ethyleneoxide, poloxyethylene alkyl ether, and polyoxyethylene sorbitane ester.
- Extreme pressure agents EP agents: zinc dialkyldithiophosphate (Zn-DTP, primary alkyl type & secondary alkyl type), sulfurized oils, diphenyl sulfide, methyl trichlorostearate, chlorinated naphthalene, benzyl iodide, fluoroalkylpolysiloxane, and lead naphthenate.
- Friction modifiers fatty alcohol, fatty acid, amine, borated ester, and other esters
- Multifunctional additives sulfurized oxymolybdenum dithiocarbamate, sulfurized oxymolybdenum organo phosphoro dithioate, oxymolybdenum monoglyceride, oxymolybdenum diethylate amide, amine-molybdenum complex compound, and sulfur-containing molybde ⁇ ym complex compound
- Viscosity index improvers polymethacrylate type polymers, ethylene-propylene copolymers, styrene-isoprene copolymers, hydrated styrene-isoprene copolymers, polyisobutylene, and dispersant type viscosity index improvers.
- High overbased alkyl hydroxy benzene sulfonates were prepared using an alkylphenol derived by contacting 3.0 moles of phenol per each mole of a normal C 20 to C 24 ⁇ -olefin mixture using Amberlyst-36 catalyst [a polystyrene cross-linked sulfonic acid resin having a Hammett acid function ( ⁇ o ) of less than -2.2 and an acid number of 5.4 milliequivalents per gram].
- Amberlyst-36 resin catalyst is commercially available from Rohm & Haas,
- the olefin mixture had the following olefinic positions, determined by using a macro program using Nuclear Magnetic Resonance Spectroscopy (NMR).
- the alkylation reactions were conducted at 100° C using a batch alkylation unit. The reaction time was six hours. Afterwards, the alkylated phenol was recovered by filtering and then stripping the excess phenol from the product stream at 400° F and 1 torr. The recovered alkylphenol products were analyzed for monoalkyl and dialkyl content and ortho/para substitution by superfluid chromatography (SFC) and fourier transform infrared spectroscopy (FT-IR) respectively.
- SFC superfluid chromatography
- FT-IR Fourier transform infrared spectroscopy
- the alkylphenol was analyzed using gas chromatography and mass spectrometry. Average positional attachment results for the C 22 carbon are as follows:
- the alkylated phenol was sulfonated using a falling film reactor.
- Feed rate of alkylphenol was 4.26 gms/min
- Air to sulfur trioxide ratio was 4:1 Reaction temperature was 90° C
- Cyclohexamine analysis for this product indicates that a sulfonate as Ca value of 3.79 wt. % was obtained.
- the reactor was equipped with a condenser for stripping and the temperature was ramped to 200° F over two hours. At 200° F, the temperature was then ramped to 270° F over 30 minutes. At 270° F, 215 grams of 100 Neutral oil was added and the entire batch was then filtered through a Buchner filter. The filtrate was then stripped to 400° F at 40mm Hg vacuum. The base number was then measured with a resulting number of 318. An additional 45 grams of 100 Neutral oil was added to adjust the base number to 312.5.
- the final product had a viscosity that was too viscous to measure at 00° C at a TBN of 312.5. It had 22.37% of the alkyl group of the sulfonate attached at the 4- position and higher positions of the alkyl group.
- the final product had a viscosity of 581 cSt at 100° C at a TBN of 300. It had 49.33 % of the alkyl group of the sulfonate attached at 4- position and higher positions of the alkyl group.
- the procedures of the Comparative Example were repeated using a polyalpha olefin derived from C ⁇ 0 dimer.
- the polyalpha olefin had the following olefinic positions, determined by using a macro program using NMR.
- the alkylphenol was analyzed using gas chromatography and mass spectrometry. Average positional attachment results for the C 22 carbon are as follows:
- the final product had a viscosity of 109 cSt at 100° C at a TBN of 296.
- Example 10 verbased phenoxy sulfonate of invention which is described in Example 1 of Specification
- Phenate I Commercially available overbased phenate Phenate ILAnother commercially available overbased phenate Sulfonate: Commercially available overbased sulfonate Salicylate I: Commercially available overbased salicylate Salicylate 11: Another commercially available overbased salicylate
- Salicylate I 1.09 Salicylate II __2
- Test method Panel coker test Oil for test: TBN 33 in SAE #40 Test conditions: 320°C, 3 hours
- SAE 10W30 oil is prepared by compounding a succinimide ashless dispersant, a low overbased calcium sulfonate, zinc dialkyldithiophosphate, and a viscosity index improver into 150 neutral oil. To the compounded oil is added the metal-containing detergent in an amount corresponding to TBN 10. Results: set forth in the following table Metal-Containing Fricti on Coefficient
- Salicylate II — —
- Test conditions 100 g of the test oil (its TBN is previously determined) and 5 g of distilled water are placed in a pressure-resistant bottle. The bottle is placed in an air thermostat at 93°C, for 24 hrs. under the condition that the bottle is rotated with upside down at 5 r.p.m., for hydrolyzing the test oil.
- the hydrolyzed test oil is then determined for its TBN. Decrease of TBN per the original TBN is calculated.
- wt.% is based on the amount of an active component, namely, with neither process oil nor diluent oil.
- the phenoxy sulfonate employed is that described in Example 1
- Phenoxy sulfonate 65.0 wt.% Primary alkyl Zn-DTP 5.9 wt.% Diluent oil 29.1 wt.%
- Phenol type oxidation inhibitor 9 1 wt.% Diluent oil 27.3 wt.%
- Phenoxy sulfonate 53.5 wt.% Alkylated diphenylamine-type oxidation inhibitor 16.3 wt % Diluent oil 30.2 wt %
- Phenol-type oxidation inhibitor 5.0 wt.%
- Alkenylsuccinimide ashless dispersant 5.8 wt.%
- Alkylated diphenylamine-type oxidation inhibitor 8.3 wt.%
- Diluent oil 27.5 wt.%
- Phenoxy sulfonate 57.0 wt.% Primary alkyl Zn-DTP 5.2 wt.% Alkenylsuccinic ester ashless dispersant 5.7 wt.% Phenol-type oxidation inhibitor 2.1 wt.%
- Alkylated diphenylamine-type oxidation inhibitor 2.0 wt.%
- Phenoxy sulfonate 37.0 wt.%
- Overbased sulfurized alkylsalicylate 28.0 wt.%
- Phenoxy sulfonate 25.3 wt.%
- Alkenylsuccinimide ashless dispersant 35.9 wt.%
- Primary alkyl Zn-DTP 11.2 wt.%
- Dithiocarbamate type anti-wear agent 3.6 wt.%
- Dithiocarbamate type anti-wear agent 0 9 wt %
- Alkenylsuccinimide ashless dispersant 37 9 wt %
- Phenol type oxidation inhibitor 1 0 wt %
- Alkylated diphenylamine-type oxidation inhibitor 4 1 wt %
- Dithiocarbamate type anti-wear agent 1 0 wt %
- Boron-containing friction modifier 2 1 wt %
- Triazol type corrosion inhibitor 3.8 wt.%
- Demulsifier 3.3 wt.%
- Nonionic anti-rust agent 3.3 wt.%
- Phenoxy sulfonate 2.3 wt.% Basic sulfurized alkylphenate 2.5 wt.% Primary alkyl Zn-DTP 49.6 wt.%
- Phenol type oxidation inhibitor 7.3 wt.% Sulfur-containing extreme pressure agent 6.0 wt.%
- Triazol type corrosion inhibitor 3.4 wt.% Demulsifier 5.0 wt.%
- Nonionic anti-rust agent 3.0 wt.%
- Diphenylamine type oxidation inhibitor 7.4 wt.% Sulfur-containing extreme pressure agent 4.5 wt.% Phosphorous-containing extreme pressure agent 39.2 wt.%
- Triazol type corrosion inhibitor 1.0 wt.%
- Nonionic anti-rust agent 4.5 wt.% Diluent oil 9.4 wt.% 4) Phenoxy sulfonate 8.5 wt.%
- Nonionic anti-rust agent 4.3 wt.%
- Polyol type friction modifier 17.9 wt.% Sulfur-containing extreme pressure agent 5.8 wt.%
- Amide type friction modifier 13.9 wt.% Sulfur-containing extreme pressure agent 6.0 wt.%
- Amide type friction modifier 10.4 wt.%
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69531043T DE69531043T2 (en) | 1994-12-28 | 1995-12-07 | OVERBASIC ALKYLOXYBENZENE SULFONATES AS DETERGENTS |
JP8520479A JPH09511015A (en) | 1994-12-28 | 1995-12-07 | Overbased alkyloxybenzene sulfonates as detergents |
EP95943415A EP0748365B1 (en) | 1994-12-28 | 1995-12-07 | Overbased alkyl oxy benzene sulfonates as detergents |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US36527294A | 1994-12-28 | 1994-12-28 | |
US08/365,272 | 1994-12-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996020265A1 true WO1996020265A1 (en) | 1996-07-04 |
Family
ID=23438179
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1995/016162 WO1996020265A1 (en) | 1994-12-28 | 1995-12-07 | Overbased alkyl oxy benzene sulfonates as detergents |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0748365B1 (en) |
JP (1) | JPH09511015A (en) |
CA (1) | CA2184159A1 (en) |
DE (1) | DE69531043T2 (en) |
WO (1) | WO1996020265A1 (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999038940A1 (en) * | 1998-02-02 | 1999-08-05 | Elf Antar France | Marine lubricant for two-stroke engine |
EP1016706A2 (en) * | 1998-12-28 | 2000-07-05 | Oronite Japan Limited | Lubricating oil composition for internal combustion engines having improved thermal oxidation durability and detergency |
US6162769A (en) * | 1998-03-26 | 2000-12-19 | B.V. Chevron Centrale Laboratoria | Lubricating oil compositions suitable for use in medium speed diesel engines |
EP1298190A1 (en) * | 2001-09-28 | 2003-04-02 | Infineum International Limited | Lubricating oil compositions for marine diesel engines |
EP1298189A1 (en) * | 2001-09-28 | 2003-04-02 | Infineum International Limited | Lubricating oil compositions for marine diesel engines |
EP1314773A1 (en) * | 2001-11-14 | 2003-05-28 | Chevrontexaco Japan Ltd. | Marine diesel engine lubrication oil composition having improved high temperature performance |
US7053027B2 (en) | 2000-05-09 | 2006-05-30 | Infineum International Limited | Lubricating oil compositions |
EP1803794A1 (en) * | 2005-12-28 | 2007-07-04 | ChevronTexaco Japan Ltd | Diesel engine lubricating oil composition for large-bore two-stroke cross-head diesel engines |
EP1803795A1 (en) * | 2005-12-28 | 2007-07-04 | Chevron Texaco Japan Ltd. | Diesel engine lubricating oil composition for large-bore two-stroke cross-head diesel engines |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8778856B2 (en) * | 2009-12-02 | 2014-07-15 | Chevron Oronite Company Llc | Low temperature performance lubricating oil detergents and method of making the same |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US3523898A (en) * | 1966-04-05 | 1970-08-11 | Phillips Petroleum Co | Increased base number metal petroleum sulfonate and process for its preparation |
US4751010A (en) * | 1985-07-08 | 1988-06-14 | Orogil | Sulfonated and sulfurized detergent-dispersant additives for lubricating oils |
US5330663A (en) * | 1992-09-02 | 1994-07-19 | Chevron Research And Technology Company | Neutral and low overbased alkylphenoxy sulfonate additive compositions |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB709587A (en) * | 1951-01-29 | 1954-05-26 | Bataafsche Petroleum | Lubricating oil compositions |
US5320762A (en) * | 1993-03-12 | 1994-06-14 | Chevron Research And Technology Company | Low viscosity Group II metal overbased sulfurized C12 to C22 alkylphenate compositions |
-
1995
- 1995-12-07 DE DE69531043T patent/DE69531043T2/en not_active Expired - Fee Related
- 1995-12-07 CA CA002184159A patent/CA2184159A1/en not_active Abandoned
- 1995-12-07 JP JP8520479A patent/JPH09511015A/en not_active Ceased
- 1995-12-07 WO PCT/US1995/016162 patent/WO1996020265A1/en active IP Right Grant
- 1995-12-07 EP EP95943415A patent/EP0748365B1/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3523898A (en) * | 1966-04-05 | 1970-08-11 | Phillips Petroleum Co | Increased base number metal petroleum sulfonate and process for its preparation |
US4751010A (en) * | 1985-07-08 | 1988-06-14 | Orogil | Sulfonated and sulfurized detergent-dispersant additives for lubricating oils |
US5330663A (en) * | 1992-09-02 | 1994-07-19 | Chevron Research And Technology Company | Neutral and low overbased alkylphenoxy sulfonate additive compositions |
Non-Patent Citations (2)
Title |
---|
"Lubricant Additives", by SMALHEER AND SMITH, 1967, page 1-11. * |
See also references of EP0748365A4 * |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999038940A1 (en) * | 1998-02-02 | 1999-08-05 | Elf Antar France | Marine lubricant for two-stroke engine |
FR2774387A1 (en) * | 1998-02-02 | 1999-08-06 | Elf Antar France | MARINE LUBRICANT FOR TWO STROKE ENGINES |
US6528459B1 (en) | 1998-02-02 | 2003-03-04 | Elf Antar France | Marine lubricant for two-stroke engine |
US6162769A (en) * | 1998-03-26 | 2000-12-19 | B.V. Chevron Centrale Laboratoria | Lubricating oil compositions suitable for use in medium speed diesel engines |
EP1016706A2 (en) * | 1998-12-28 | 2000-07-05 | Oronite Japan Limited | Lubricating oil composition for internal combustion engines having improved thermal oxidation durability and detergency |
EP1016706A3 (en) * | 1998-12-28 | 2001-01-17 | Oronite Japan Limited | Lubricating oil composition for internal combustion engines having improved thermal oxidation durability and detergency |
US7053027B2 (en) | 2000-05-09 | 2006-05-30 | Infineum International Limited | Lubricating oil compositions |
EP1298189A1 (en) * | 2001-09-28 | 2003-04-02 | Infineum International Limited | Lubricating oil compositions for marine diesel engines |
EP1298190A1 (en) * | 2001-09-28 | 2003-04-02 | Infineum International Limited | Lubricating oil compositions for marine diesel engines |
EP1314773A1 (en) * | 2001-11-14 | 2003-05-28 | Chevrontexaco Japan Ltd. | Marine diesel engine lubrication oil composition having improved high temperature performance |
EP1803794A1 (en) * | 2005-12-28 | 2007-07-04 | ChevronTexaco Japan Ltd | Diesel engine lubricating oil composition for large-bore two-stroke cross-head diesel engines |
EP1803795A1 (en) * | 2005-12-28 | 2007-07-04 | Chevron Texaco Japan Ltd. | Diesel engine lubricating oil composition for large-bore two-stroke cross-head diesel engines |
US7956021B2 (en) | 2005-12-28 | 2011-06-07 | Chevron Japan Ltd. | Diesel engine lubricating oil composition for large-bore two-stroke cross-head diesel engines |
Also Published As
Publication number | Publication date |
---|---|
EP0748365B1 (en) | 2003-06-11 |
EP0748365A4 (en) | 1998-12-16 |
JPH09511015A (en) | 1997-11-04 |
DE69531043D1 (en) | 2003-07-17 |
EP0748365A1 (en) | 1996-12-18 |
DE69531043T2 (en) | 2003-12-04 |
CA2184159A1 (en) | 1996-07-04 |
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