EP0323088A1 - Préparation de sulfonate de magnésium superbasique - Google Patents

Préparation de sulfonate de magnésium superbasique Download PDF

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Publication number
EP0323088A1
EP0323088A1 EP88311968A EP88311968A EP0323088A1 EP 0323088 A1 EP0323088 A1 EP 0323088A1 EP 88311968 A EP88311968 A EP 88311968A EP 88311968 A EP88311968 A EP 88311968A EP 0323088 A1 EP0323088 A1 EP 0323088A1
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EP
European Patent Office
Prior art keywords
magnesium
sulphonate
reaction mixture
acid
ashless dispersant
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.)
Ceased
Application number
EP88311968A
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German (de)
English (en)
Inventor
John Arthur Cleverley
John Frederick Marsh
Joseph Marian Swietlik
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ExxonMobil Chemical Patents Inc
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Exxon Chemical Patents Inc
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Filing date
Publication date
Priority claimed from GB878730231A external-priority patent/GB8730231D0/en
Priority claimed from GB888806971A external-priority patent/GB8806971D0/en
Application filed by Exxon Chemical Patents Inc filed Critical Exxon Chemical Patents Inc
Publication of EP0323088A1 publication Critical patent/EP0323088A1/fr
Ceased legal-status Critical Current

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    • 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
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention related to improved overbased magnesium sulphonates and to compositions containing them, particularly for use in lubricating oils for use in transport applications.
  • Magnesium sulphonates are well-known lubricant additives, and are described as "overbased” when they contain a stoichiometric excess of magnesium compared to that required to neutralize the sulphonic acid.
  • Overbased magnesium sulphonates are commonly used as detergents in lubricating oils. They are generally prepared by carbonation of a reaction mixture comprising a sulphonic acid or sulphonate and an excess of a magnesium compound such as an alkoxide, oxide or hydroxide in oil, typically with a hydrocarbon solvent and usually in the presence of a promoter. Examples of preparations are found in US-A-3158009, GB-A-1166744, GB-A-1297150, GB-A-1399092, EP-A-0013808 and EP-A-0015341.
  • Lubricating oils for automobile are having to pass increasingly severe tests, usually engine tests, for approval by automobile manufacturers, and/or to meet industry standards.
  • tests for sludge and varnish inhibition are becoming more severe requiring the use of more potent dispersants.
  • the oils are also being required to be more resistant to thickening caused by oxidation, requiring the use of potent antioxidants.
  • the SC quality level in the API Engine Service Categories for service station oils developed by API in conjunction with ASTM and SAE reflects this increased severity in requirements for passenger car applications.
  • API in conjunction with ASTM and SAE has developed a more stringent engine test (Sequence 6 Test) for determining fuel economy performance, and a pass at the so-called "Tier II" level of fuel economy for a lubricating oil requires a 2.7 percent minimum improvement in fuel economy versus a standard lubricating oil run in the Sequence 6 engine test.
  • overbased magnesium sulphonates in lubricating oils designed to meet these more stringent criteria can give rise to problems of interactions between the additives, either in concentrated form or in the finished lubricants, which may result in undesirable sediment or haze formation.
  • This invention relates to overbased magnesium sulphonates having increased resistance to interactions, to modifications to the manufacture of overbased magnesium sulphonates to reduce interactions and to compositions comprising overbased magnesium sulphonate, particularly in combination with high molecular weight dispersants and/or friction modifiers.
  • the invention may provide stable sediment-free lubricating oil compositions (including lubricants and concentrates therefor) which can meet the proposals for SG quality and the Tier II fuel economy requirement (as defined hereinbefore).
  • the high molecular weight dispersants which may be used in the invention include those of number average molecular weight (M n ) of greater than 1300, e.g. those described in EP-A-0208560.
  • Friction modifiers are well known and include polar materials such as partial esters of fatty acids such as glyceryl mono-oleate, various straight chain acids such as oleic acid and stearic acid and derivatives of linoleic acid dimers.
  • the overbased magnesium sulphonate is prepared by a process as described hereinbefore in which the reaction mixture for carbonation contains an effective amount, preferably 0.5 to 10 wt% (of the formed overbased magnesium sulphonate) of an ashless dispersant.
  • the ashless dispersant is preferably a reaction product of:
  • an ashless dispersant comprising a hydrocarbyl-substituted C4 to C10 mono-unsaturated acid or anhydride may, without further reaction, be used in the reaction mixture in the preparation of an overbased magnesium sulphonate according to the invention.
  • ashless is used in connection with dispersants herein as it is used in the field of lubricating compositions - that is, to refer to dispersants which do not form any significant amounts of ash, sulphated ash- (as measured e.g. by ASTM D482 and 874) on combustion, and are not metal salts.
  • the term does not exclude borated materials as described herein, or dispersants containing incidental amounts of metal salts, such as zinc salts, which are occasionally used in preparing ashless dispersants as catalysts and may be present in the product typically in an amount of 0.01 to 0.5 wt % of the dispersant.
  • the hydrocarbyl-substituted C4 to C10 mono-unsaturated acid or anhydride is preferably a hydrocarbyl succinic acid or anhydride comprising a hydrocarbon group substituted with one or more moles, per mole of hydrocarbon, of maleic acid.
  • the preferred hydrocarbon is a long chain hydrocarbon having at least 50 carbon atoms, and polyolefins having a molecular weight of at least 900 are more preferred.
  • the preferred polyolefin is polyisobutylene, and for convenience hereinafter polyisobutenyl succinic anhydride or acid will be referred to as PIBSA.
  • a preferred category of PIBSA has a number average molecular weight of from 900 to 5000, and more preferably also comprises at least 1 succinic moiety per polyisobutene.
  • b) is a polyamine (hereinafter referred to as PAM).
  • PAMs are polyalkyleneamines with alkylene groups containing 2 to 6 carbon atoms and with 2 to 8 nitrogen atoms per molecule.
  • the polyamines used may comprise a single polyalkyleneamine, or a commercial mixture comprising two more more such amines.
  • M n number average weight
  • a wide range of ashless dispersant, and particularly PIBSA based dispersants, may be used in the invention. Each of these products may be used in a borated form or without boration.
  • the preferred process of the invention comprises carbonating a reaction mixture comprising:
  • the sulphonic acid or sulphonate may be natural or synthetic with synthetic alkylaryl sulphonic acids and sulphonates being preferred.
  • the alkyl substituent in such alkylaryl moieties may have 15 or more carbon atoms and is typically a polyolefin formed from an olefin having 2 to 5 carbon atoms.
  • the magnesium compound provides the basicity to the formed overbased magnesium sulphonate and is therefore present in excess of the amount stoichiometrically required to react with the sulphonic acid, the amount in the product dictating the total base number (TBN) of the product. It may however be introduced in stages with intervening carbonation steps.
  • the solvent is typically present in an amount of from 0.1 to 10 parts by weight of solvent per part of magnesium in the reaction mixture.
  • the promoter is typically present in an amount of from 0.01 to 5 parts by weight per part of magnesium in the reaction mixture.
  • Water may be present in an amount of from 0 to 2 parts by weight per part of magnesium in the reaction mixture.
  • An additional surfactant such as an alkyl phenol may be present in an amount of from 0 to 1 part by weight per part of magnesium present in the reaction mixture.
  • the reaction mixture is carbonated by passing carbon dioxide gas through the mixture at a typical temperature of 25° to 200°C, with a preferred range being 50° to 150°C.
  • the product may be stripped to remove volatiles, and filtered to remove solids, but these operations may be carried out in either order. Further carbonation may be carried out during stripping and further oil may be added to replace material lost in stripping.
  • the formed product may be post-treated with a carboxylic acid and/or a glycol to improve the water tolerance and/or stability and/or foaming performance and/or seal compatibility thereof.
  • the overbased magnesium sulphonate preferably has a total base number (TBN) as measured by ASTM D2896 of at least 300, more preferably 300 to 450, and most preferably about 400.
  • TBN total base number
  • overbased magnesium sulphonates may be used in oleaginous compositions, e.g. lubricants and concentrates therefor, and in particular those comprising:-
  • the overbased magnesium sulphonate will typically comprise from 0.01 to 5 wt % of such compositions for use as crankcase lubricants, but concentrates may contain up to 50 wt % of the overbased magnesium sulphonate.
  • the tendency for such compositions and concentrates to give interactions may be tested by blending the additives required for the composition or concentrate which are then stored at an elevated temperature, typically 54°C or 66°C and observing the appearance of haze/sediment.
  • a lubricating oil composition or concentrate may be regarded as being acceptably stable if it is clear and substantially free from haze and/or sediment after at least 3 months at 66°C.
  • the compositions of the invention may provide a means of meeting more severe testing regimes with acceptably stable formulations and packages.
  • compositions contain a major amount of a lubricating oil which may be a mineral lubricating oil, a synthetic lubricating oil or mixtures thereof.
  • the synthetic oils include polyalpha olefins, diester oils, such as di(2-ethylhexyl) sebacate, azelate and adipate, complex ester oils such as those formed from dicarboxylic acids, glycols and either monobasic acids or monohydric alcohols and silicone oils.
  • compositions may contain additives such as viscosity modifiers, corrosion inhibitors, other oxidation inhibitors, other friction modifiers, other dispersants, anti-foaming agents, anti-wear agents, pour point depressants, detergents, rust inhibitors and the like.
  • additives such as viscosity modifiers, corrosion inhibitors, other oxidation inhibitors, other friction modifiers, other dispersants, anti-foaming agents, anti-wear agents, pour point depressants, detergents, rust inhibitors and the like.
  • Viscosity modifiers impart high and low temperature operability to the lubricating oil and permit it to remain shear stable at elevated temperatures and also exhibit acceptable viscosity or fluidity at low temperatures.
  • Viscosity modifiers are generally high molecular weight hydrocarbon polymers including polyesters.
  • the viscosity modifiers may also be derivatized to include other properties or functions, such as the addition of dispersancy properties.
  • oil soluble viscosity modifying polymers will generally have number average molecular weights of from 103 to 106, preferably 104 to 106, e.g. 20,000 to 250,000, as determined by gel permeation chromatrography or membrane osmometry.
  • suitable viscosity modifiers are any of the types known to the art including polyisobutylene, copolymers of ethylene and propylene, polymethacrylates, methacrylate copolymers, copolymers of an unsaturated dicarboxylic acid and vinyl compound, interpolymers of styrene and acrylic esters, and styrene/isoprene copolymers.
  • Corrosion inhibitors also known as anti-corrosive agents, reduce the degradation of the metallic parts contacted by the lubricating oil composition.
  • Illustrative of corrosion inhibitors are phosphosulphurized hydrocarbons and the products obtained by reaction of a phosphosulphurized hydrocarbon with an alkaline earth metal oxide or hydroxide, preferably in the presence of an alkylated phenol or of an alkylphenol thioester, and also preferably in the presence of carbon dioxide.
  • Phosphosulphurized hydrocarbons are prepared by reacting a suitable hydrocarbon such as terpene, a heavy petroleum fraction of a C2 to C6 olefin polymer such as polyisobutylene, with from 5 to 30 wt % of a sulfide of phosphorus for 1/2 to 15 hours, at a temperature in the range of 150°F to 600°F.
  • a suitable hydrocarbon such as terpene, a heavy petroleum fraction of a C2 to C6 olefin polymer such as polyisobutylene
  • Neutralization of the phosphosulphurized hydrocarbon may be effected in the manner taught in US Patent No. 1,969,324.
  • Oxidation inhibitors reduce the tendency of mineral oils to deteriorate in service which deterioration can be evidenced by the products of oxidation such as sludge and varnish-like deposits on the metal surfaces and by viscosity growth.
  • oxidation inhibitors include ZDDP's, aromatic amines such alkylated diphenylamines and phenyl alpha naphthylamine, hindered phenols, copper compounds, alkaline earth metal salts of alkylphenolthioesters having preferably C5 to C12 alkyl side chains, eg, calcium nonylphenol sulphide, barium t-octylphenyl sulphide, dioctylphenyl-amine, phenylalphanaphthylamine and phosphosulphurized or sulphurized hydrocarbons.
  • Friction modifiers serve to impact the proper friction characteristics to lubricating oil compositions such as automatic transmission fluids.
  • Dispersants maintain oil insolubles, resulting from oxidation during use, in suspension in the fluid thus preventing sludge flocculation and precipitation or deposition on metal parts.
  • High molecular weight ashless dispersants for use in the invention have a number average molecular weight of at least 1300 and preferably comprise an alkenyl succinimide, the reaction product of oil-soluble polyisobutylene succinic anhydride with an amine such as an ethylene amine which may optionally be borated.
  • Pour point depressants lower the temperature at which the fluid will flow or can be poured.
  • Such depressants are well known.
  • those additives which usefully optimize the low temperature fluidity of the fluid are C8-C18 dialkylfumarate vinyl acetate copolymers, polymethacrylates, and wax naphthalene.
  • Foam control can be provided by an antifoamant of the polysiloxane type, eg silicone oil and polydimethyl siloxane.
  • Additional detergents and metal rust inhibitors may be present including the metal salts of sulphonic acids, alkyl phenols, sulphurized alkyl phenols, alkyl saliscylates, naphthenates and other oil soluble mono- and di-carboxylic acids.
  • Highly basic (viz, overbased) metal salts such as highly basic alkali and alkaline earth metal sulphonates (especially Na, Ca and Mg salts) are frequently used as detergents, alone and in combination. Mixtures of calcium and magnesium salts, and of calcium, magnesium and sodium salts are preferred.
  • Copper and lead corrosion inhibitors and antiwear agents include borate esters, thiadiazoles such as derivatives of 2, 5 dimercapto 1,3,4-thiadiazole and benzotriazoles.
  • compositions when containing these conventional additives are typically blended into the base oil in amounts which are effective to provide their normal attendant function.
  • Representative effective amounts of such additives are illustrated as follows: Additive Vol % Wt % a.i. Viscosity Modifier .01-4 .01-4 Corrosion Inhibitor 0.01-1 .01-1.5 Oxidation Inhibitor 0.01-1 .01-1.5 Dispersant 0.1-7 0.1-8 Pour Point Depressant 0.01-1 .01-1.5 Anti-Foaming Agents 0.001-0.1 .001-0.15 Anti-Wear Agents 0.001-1 .001-1.5 Friction Modifiers 0.01-1 .01-1.5 Detergents/Rust Inhibitors .01-2.5 .01-3 Mineral Oil Base Balance Balance Balance
  • additive concentrates comprising concentrated solutions or dispersions of the dispersant (in concentrate amounts hereinabove described), together with one or more of said other additives (said concentrate when constituting an additive mixture being referred to herein as an additive-package) whereby several additives can be added simultaneously to the base oil to form the lubricating oil composition. Dissolution of the additive concentrate into the lubricating oil may be facilitated by solvents and by mixing accompanied with mild heating, but this is not essential.
  • the concentrate or additive-package will typically be formulated to contain the dispersant additive and optional additional additives in proper amounts to provide the desired concentration in the final formulation when the additive-package is combined with a predetermined amount of base lubricant.
  • additives of the present invention can be added to small amounts of base oil or other compatible solvents along with other desirable additives to form additive-packages containing active ingredients in collective amounts of typically from about 2.5 to about 90%, and preferably from about 5 to about 75%, and most preferably from about 8 to about 50% by weight additives in the appropriate proportions with the remainder being base oil.
  • the final formulations may employ typically about 10 wt % of the additive-package with the remainder being base oil.
  • weight percents expressed herein are based on active ingredient (a.i.) content of the additive, and/or upon the total weight of any additive-package, or formulation, which will be the sum of the a.i. weight of each additive plus the weight of total oil or diluent.
  • An overbased magnesium sulphonate was prepared by carbonation at 40-70°C of a reaction mixture comprising:
  • the formed overbased magnesium sulphonates were blended into a typical service station oil additive package including in addition to other conventional additives 18.2% of a borated PIBSA/PAM dispersant in which the polyisobutene moiety has a number average molecular weight of about 2200, 120 ppm of added copper as antioxidant and 0.75 wt % of glyceryl monooleate as friction modifier.
  • the overbased magnesium sulphonate comprised 9.85 wt % of this package.
  • PIBSA 3.0% 40+ 7 2200 M.W. PIBSA 5.0% 40+ 8 900 M.W. PIBSA 2.5% 5 9 1300 M.W. PIBSA 2.5% 12 10 Borated 1300 M.W. PIBSA/PAM 5% 12 1. as wt. percentage of 400 TBN overbased magnesium sulphonate product 2. average of 10 repeats 3. M.W. number average molecular weight.

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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)
  • Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
  • Lubricants (AREA)
EP88311968A 1987-12-29 1988-12-16 Préparation de sulfonate de magnésium superbasique Ceased EP0323088A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8730231 1987-12-29
GB878730231A GB8730231D0 (en) 1987-12-29 1987-12-29 Improved overbased magnesium sulphonate
GB888806971A GB8806971D0 (en) 1988-03-23 1988-03-23 Improved overbased magnesium sulphonate
GB8806971 1988-03-23

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0461842A1 (fr) * 1990-06-11 1991-12-18 Ethyl Petroleum Additives, Inc. Lubrifiants à teneur en cendres réduite
WO1992018588A1 (fr) * 1991-04-19 1992-10-29 The Lubrizol Corporation Compositions lubrifiantes
WO1993006195A1 (fr) * 1991-09-19 1993-04-01 Exxon Chemical Patents Inc. Detergents surbasiques contenant des metaux
EP0652279A1 (fr) * 1993-06-07 1995-05-10 Ethyl Corporation Economie de carburant et inhibition de l'oxydation dans des compositions lubrifiantes pour moteurs à combustion interne
US5490945A (en) * 1991-04-19 1996-02-13 The Lubrizol Corporation Lubricating compositions and concentrates
US5562864A (en) * 1991-04-19 1996-10-08 The Lubrizol Corporation Lubricating compositions and concentrates
US5614480A (en) * 1991-04-19 1997-03-25 The Lubrizol Corporation Lubricating compositions and concentrates
WO2011068732A2 (fr) 2009-12-03 2011-06-09 Chevron Oronite Company Llc Alkyltoluènesulfonates de magnésium fortement surbasifiés
EP3153568A1 (fr) * 2015-10-05 2017-04-12 Infineum International Limited Concentrés d'additif pour la formulation de compositions d'huile lubrifiante
EP3339403A1 (fr) * 2016-12-22 2018-06-27 Infineum International Limited Synthèse de sulfonate de magnésium

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1139172A (en) * 1966-01-28 1969-01-08 Monsanto Chemicals Process for the production of oil solutions of sulphonate/carbonate complexes
FR2265848A1 (en) * 1974-03-29 1975-10-24 Inst Francais Du Petrole Over based detergent additive for lubricants - obtd by carbonating metal hydroxide-oil soluble metal sulphonate-polyalkenyl-succinimide-amine salt
GB2023169A (en) * 1978-06-14 1979-12-28 Lubrizol Corp Concentrates lubricant composotions and mathods for improving fuel economy of internal combustion engines
EP0047126A2 (fr) * 1980-08-29 1982-03-10 Exxon Research And Engineering Company Procédé pour la production de sulfonate de calcium
FR2580291A1 (fr) * 1985-04-11 1986-10-17 Witco Corp Sulfonates de magnesium superbasiques contenant un promoteur d'anhydride succinique et huiles contenant ces sulfonates
EP0212922A2 (fr) * 1985-08-13 1987-03-04 Exxon Chemical Patents Inc. Additifs surbasiques
WO1987006256A2 (fr) * 1986-04-11 1987-10-22 The Lubrizol Corporation Compositions de graisse et de lubrifiants pour engrenage comprenant au moins une composition contenant un metal et au moins un compose organique sulfure

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1139172A (en) * 1966-01-28 1969-01-08 Monsanto Chemicals Process for the production of oil solutions of sulphonate/carbonate complexes
FR2265848A1 (en) * 1974-03-29 1975-10-24 Inst Francais Du Petrole Over based detergent additive for lubricants - obtd by carbonating metal hydroxide-oil soluble metal sulphonate-polyalkenyl-succinimide-amine salt
GB2023169A (en) * 1978-06-14 1979-12-28 Lubrizol Corp Concentrates lubricant composotions and mathods for improving fuel economy of internal combustion engines
EP0047126A2 (fr) * 1980-08-29 1982-03-10 Exxon Research And Engineering Company Procédé pour la production de sulfonate de calcium
FR2580291A1 (fr) * 1985-04-11 1986-10-17 Witco Corp Sulfonates de magnesium superbasiques contenant un promoteur d'anhydride succinique et huiles contenant ces sulfonates
EP0212922A2 (fr) * 1985-08-13 1987-03-04 Exxon Chemical Patents Inc. Additifs surbasiques
WO1987006256A2 (fr) * 1986-04-11 1987-10-22 The Lubrizol Corporation Compositions de graisse et de lubrifiants pour engrenage comprenant au moins une composition contenant un metal et au moins un compose organique sulfure

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0461842A1 (fr) * 1990-06-11 1991-12-18 Ethyl Petroleum Additives, Inc. Lubrifiants à teneur en cendres réduite
WO1992018588A1 (fr) * 1991-04-19 1992-10-29 The Lubrizol Corporation Compositions lubrifiantes
AU657333B2 (en) * 1991-04-19 1995-03-09 Lubrizol Corporation, The Lubricating compositions
US5490945A (en) * 1991-04-19 1996-02-13 The Lubrizol Corporation Lubricating compositions and concentrates
US5562864A (en) * 1991-04-19 1996-10-08 The Lubrizol Corporation Lubricating compositions and concentrates
US5614480A (en) * 1991-04-19 1997-03-25 The Lubrizol Corporation Lubricating compositions and concentrates
WO1993006195A1 (fr) * 1991-09-19 1993-04-01 Exxon Chemical Patents Inc. Detergents surbasiques contenant des metaux
EP0652279A1 (fr) * 1993-06-07 1995-05-10 Ethyl Corporation Economie de carburant et inhibition de l'oxydation dans des compositions lubrifiantes pour moteurs à combustion interne
WO2011068732A2 (fr) 2009-12-03 2011-06-09 Chevron Oronite Company Llc Alkyltoluènesulfonates de magnésium fortement surbasifiés
EP3153568A1 (fr) * 2015-10-05 2017-04-12 Infineum International Limited Concentrés d'additif pour la formulation de compositions d'huile lubrifiante
US11168280B2 (en) 2015-10-05 2021-11-09 Infineum International Limited Additive concentrates for the formulation of lubricating oil compositions
EP3339403A1 (fr) * 2016-12-22 2018-06-27 Infineum International Limited Synthèse de sulfonate de magnésium

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BR8806939A (pt) 1989-08-29
JPH01308820A (ja) 1989-12-13

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