EP0748365A1 - Sulfonates de benzene oxy alkyle hyperbasiques utilises comme detergents - Google Patents

Sulfonates de benzene oxy alkyle hyperbasiques utilises comme detergents

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Publication number
EP0748365A1
EP0748365A1 EP95943415A EP95943415A EP0748365A1 EP 0748365 A1 EP0748365 A1 EP 0748365A1 EP 95943415 A EP95943415 A EP 95943415A EP 95943415 A EP95943415 A EP 95943415A EP 0748365 A1 EP0748365 A1 EP 0748365A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
oxy benzene
overbased
alkyl oxy
sulfonate
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.)
Granted
Application number
EP95943415A
Other languages
German (de)
English (en)
Other versions
EP0748365A4 (fr
EP0748365B1 (fr
Inventor
William F. King
Richard J. Nelson
Steven G. Lockett
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.)
Chevron Phillips Chemical Co LP
Original Assignee
Chevron Chemical Co LLC
Chevron Oronite Co LLC
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 Chevron Chemical Co LLC, Chevron Oronite Co LLC filed Critical Chevron Chemical Co LLC
Publication of EP0748365A1 publication Critical patent/EP0748365A1/fr
Publication of EP0748365A4 publication Critical patent/EP0748365A4/fr
Application granted granted Critical
Publication of EP0748365B1 publication Critical patent/EP0748365B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C10M129/04—Hydroxy compounds
    • C10M129/06—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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    • 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-fuelled 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
    • C10N2040/252—Diesel 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
    • C10N2040/252—Diesel engines
    • C10N2040/253—Small diesel 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

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
  • Metallic detergents overbased sulfurized alkylphenates, overbased sulfonates, and overbased salicylates.
  • Ashless dispersants alkenyl succinimides, alkenyl succinimides modified with other organic compounds, and alkenyl succinimides modified with boric acid, alkenyl succinic ester.
  • 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.%

Landscapes

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

Abstract

La présente invention concerne un lubrifiant pour moteurs marins constitué, pour une majeure partie, d'une huile dont la viscosité lui confère un pouvoir lubrifiant, et pour une partie mineure, d'un sulfonate de benzène oxy alkyle possédant un indice de basicité totale (TBN) au moins égal à 200. Entre 40 et 80 % en poids du groupe alkyle est fixé au niveau de la position 4 ou des positions d'ordre supérieur du groupe alkyle. Le groupe oxy peut être un groupe hydroxy, méthoxy, éthoxy, propoxy, butoxy, pentoxy ou hexoxy.
EP95943415A 1994-12-28 1995-12-07 Sulfonates de benzene oxy alkyle hyperbasiques utilises comme detergents Expired - Lifetime EP0748365B1 (fr)

Applications Claiming Priority (3)

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US36527294A 1994-12-28 1994-12-28
US365272 1994-12-28
PCT/US1995/016162 WO1996020265A1 (fr) 1994-12-28 1995-12-07 Sulfonates de benzene oxy alkyle hyperbasiques utilises comme detergents

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FR2774387B1 (fr) * 1998-02-02 2000-12-01 Elf Antar France Lubrifiant marin pour moteur deux temps
EP0945499B1 (fr) * 1998-03-26 2011-05-11 Chevron Oronite Company LLC Compositions lubrifiantes utilisable dans les moteurs diesel à vitesse moyenne
JP2000192069A (ja) * 1998-12-28 2000-07-11 Oronite Japan Ltd ディ―ゼル内燃機関用潤滑油組成物及び添加剤組成物
US6551965B2 (en) * 2000-02-14 2003-04-22 Chevron Oronite Company Llc Marine diesel engine lubricating oil composition having improved high temperature performance
GB0011115D0 (en) 2000-05-09 2000-06-28 Infineum Int Ltd Lubricating oil compositions
EP1298189A1 (fr) * 2001-09-28 2003-04-02 Infineum International Limited Composition lubrifiante pour la lubrification d'un moteur diesel marin
EP1298190B1 (fr) * 2001-09-28 2005-10-12 Infineum International Limited Compositions lubrifiantes pour la lubrification d'un moteur diesel marin
US7875577B2 (en) * 2005-12-28 2011-01-25 Chevron Japan Ltd. Diesel engine lubricating oil composition for large-bore two-stroke cross-head diesel engines
JP4787016B2 (ja) 2005-12-28 2011-10-05 シェブロンジャパン株式会社 ディーゼル内燃機関用潤滑油組成物
US8778856B2 (en) * 2009-12-02 2014-07-15 Chevron Oronite Company Llc Low temperature performance lubricating oil detergents and method of making the same

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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

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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
FR2584414B1 (fr) * 1985-07-08 1987-10-30 Orogil Nouveaux additifs detergents-dispersants sulfones et sulfurises pour huiles lubrifiantes
US5330663A (en) * 1992-09-02 1994-07-19 Chevron Research And Technology Company Neutral and low overbased alkylphenoxy sulfonate additive compositions

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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

Non-Patent Citations (1)

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Title
See also references of WO9620265A1 *

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WO1996020265A1 (fr) 1996-07-04
EP0748365A4 (fr) 1998-12-16
DE69531043T2 (de) 2003-12-04
JPH09511015A (ja) 1997-11-04
DE69531043D1 (de) 2003-07-17
EP0748365B1 (fr) 2003-06-11
CA2184159A1 (fr) 1996-07-04

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