EP3470499A1 - Utilisation des détergents dans les huiles lubrifiantes de moteur à combustion interne - Google Patents
Utilisation des détergents dans les huiles lubrifiantes de moteur à combustion interne Download PDFInfo
- Publication number
- EP3470499A1 EP3470499A1 EP18195639.2A EP18195639A EP3470499A1 EP 3470499 A1 EP3470499 A1 EP 3470499A1 EP 18195639 A EP18195639 A EP 18195639A EP 3470499 A1 EP3470499 A1 EP 3470499A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- lubricant
- detergent
- engine
- active ingredient
- mass
- 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
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- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000629 steam reforming Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010729 system oil Substances 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical class CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- MQHSFMJHURNQIE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) silicate Chemical compound CCCCC(CC)CO[Si](OCC(CC)CCCC)(OCC(CC)CCCC)OCC(CC)CCCC MQHSFMJHURNQIE-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- ZAGXLQIHXTXRFW-UHFFFAOYSA-N tris(2-ethyl-4-methylhexyl)-tris(2-ethyl-4-methylhexyl)silyloxysilane Chemical compound CCC(C)CC(CC)C[Si](CC(CC)CC(C)CC)(CC(CC)CC(C)CC)O[Si](CC(CC)CC(C)CC)(CC(CC)CC(C)CC)CC(CC)CC(C)CC ZAGXLQIHXTXRFW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- 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
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
-
- 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
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/04—Detergent property or dispersant property
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- 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
- C10N2040/252—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
- C10N2040/255—Gasoline engines
- C10N2040/26—Two-strokes or two-cycle 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
- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
- C10N2060/10—Chemical after-treatment of the constituents of the lubricating composition by sulfur or a compound containing sulfur
Definitions
- Natural oils include animal oils and vegetable oils (e.g., castor oil, lard oil); liquid petroleum oils and hydrorefined, solvent-treated or acid-treated mineral oils of the paraffinic, naphthenic and mixed paraffinic-naphthenic types. Oils of lubricating viscosity derived from coal or shale also serve as useful base oils.
- Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(1-hexenes), poly(1-octenes), poly(l-decenes)); alkybenzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl)benzenes); polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenols); and alkylated diphenyl ethers and alkylated diphenyl sulphides and derivatives, analogues and homologues thereof.
- esters includes dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid.
- Unrefined, refined and re-refined oils can be used in lubricants of the present invention.
- Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment. For example, a shale oil obtained directly from retorting operations; petroleum oil obtained directly from distillation; or ester oil obtained directly from esterification and used without further treatment are unrefined oils.
- the present invention preferably embraces Group I or Group II base stocks or oils.
- the oil of lubricating viscosity in this invention contains 50 mass % or more of said basestocks. It may contain 60, such as 70, 80 or 90, mass % or more of said basestock or a mixture thereof.
- the oil of lubricating viscosity may be substantially all of said basestock or a mixture thereof.
- the invention is not however limited to use of the above-mentioned base stocks; thus it may, for example, include use of Group III, IV or V basestocks and of bright stock. They also include basestocks derived from hydrocarbons synthesised by the Fischer-Tropsch process.
- the syngas may, for example, be made from gas such as natural gas or other gaseous hydrocarbons by steam reforming, when the basestock may be referred to as gas-to-liquid (“GTL”) base oil; or from gasification of biomass, when the basestock may be referred to as biomass-to-liquid (“BTL” or “BMTL”) base oil; or from gasification of coal, when the basestock may be referred to as coal-to-liquid (“CTL”) base oil.
- GTL gas-to-liquid
- BTL biomass-to-liquid
- CTL coal-to-liquid
- the TBN of the lubricant is preferably in the range of 5 to 160, and the total detergent concentration in the additive package is preferably from greater than 50 up to 99, such as 60 to 98 or 70 to 95, as a percentage by mass of the total active ingredient.
- the lubricant may further comprise an overbased sulfonate (preferably calcium) detergent, for example having a TBN in the range of 250 to 800 on an active ingredients basis and, for example, in a concentration of 20 to 95, such as 30 to 90 or 40 to 85, % as a percentage by mass of the total active ingredient.
- an overbased sulfonate (preferably calcium) detergent for example having a TBN in the range of 250 to 800 on an active ingredients basis and, for example, in a concentration of 20 to 95, such as 30 to 90 or 40 to 85, % as a percentage by mass of the total active ingredient.
- Marine cylinder lubricants are routinely formulated with high base number metal detergents as the main additive constituents to neutralise the acid produced from the high sulfur fuels used in operation of the engines.
- a preferred class of olefin polymers is constituted by polybutenes, specifically polyisobutenes (PIB) or poly-n-butenes, such as may be prepared by polymerization of a C 4 refinery stream.
- PIB polyisobutenes
- poly-n-butenes such as may be prepared by polymerization of a C 4 refinery stream.
- Dispersants include, for example, derivatives of long chain hydrocarbon-substituted carboxylic acids, examples being derivatives of high molecular weight hydrocarbyl-substituted succinic acid.
- a noteworthy group of dispersants is constituted by hydrocarbon-substituted succinimides, made, for example, by reacting the above acids (or derivatives) with a nitrogen-containing compound, advantageously a polyalkylene polyamine, such as a polyethylene polyamine.
- Hydrocarbon-substituted succinimides such as those described above may be post-treated to improve their properties, such as through boration (as described in US-A-3,087,936 and - 3,254,025 ).
- boration may be accomplished by treating an acyl nitrogen-containing dispersant with a boron compound selected from boron oxide, boron halides, boron acids and esters of boron acids.
- Sulfonate detergents are metal salts and may contain a substantially stoichiometric amount of the metal when they are usually described as normal or neutral salts and would typically have a total base number or TBN (as may be measured by ASTM D2896) of from 0 to 80.
- TBN total base number
- Large amounts of a metal base can be included by reaction of an excess of a metal compound, such as an oxide or hydroxide, with an acidic gas such as carbon dioxide.
- the resulting overbased detergent comprises neutralised detergent as an outer layer of a metal base (e.g. carbonate) micelle.
- Such overbased sulfonate detergents may have a TBN of 150 or greater, and typically of from 250 to 800 or more on an active ingredient basis.
- Phenate Detergent B is an overbased sulfurized calcium phenate detergent derived from tetrapropenylphenol.
- the detergent is synthesised according to well established two stage methods (i.e. sulfurization and overbasing stages are conducted independently as described in EP 2682451 B1 and US 3,801,507 ). It has the same generalised structure as Phenate Detergent A. It is characterised by a TBN of 375 to 425 on an active ingredients basis.
- the HT-HFRR rig is run at elevated temperatures and the friction coefficient (Fc) is recorded.
- the friction co-efficient decreases with increasing temperature due to the viscosity decrease of the MDCL, until a temperature at which oil film break-down begins and the friction coefficient (Fc) starts to increase with increasing temperature.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP17196562 | 2017-10-16 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP3470499A1 true EP3470499A1 (fr) | 2019-04-17 |
EP3470499B1 EP3470499B1 (fr) | 2021-01-13 |
Family
ID=60117569
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP18195639.2A Active EP3470499B1 (fr) | 2017-10-16 | 2018-09-20 | Utilisation des détergents dans les huiles lubrifiantes de moteur à combustion interne |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP3470499B1 (fr) |
JP (1) | JP2019073703A (fr) |
CN (1) | CN109666525B (fr) |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3024237A (en) | 1959-08-24 | 1962-03-06 | California Research Corp | Alkenyl succinimides of piperazines |
US3087936A (en) | 1961-08-18 | 1963-04-30 | Lubrizol Corp | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
US3154560A (en) | 1961-12-04 | 1964-10-27 | Monsanto Co | Nu, nu'-azaalkylene-bis |
US3172892A (en) | 1959-03-30 | 1965-03-09 | Reaction product of high molecular weight succinic acids and succinic anhydrides with an ethylene poly- amine | |
US3202678A (en) | 1959-08-24 | 1965-08-24 | California Research Corp | Alkenyl succinimides of tetraethylene pentamine |
US3216936A (en) | 1964-03-02 | 1965-11-09 | Lubrizol Corp | Process of preparing lubricant additives |
US3801507A (en) | 1972-08-18 | 1974-04-02 | Chevron Res | Sulfurized metal phenates |
EP2682451A1 (fr) | 2012-07-06 | 2014-01-08 | Infineum International Limited | Modification de détergent |
EP2719751A2 (fr) | 2012-06-07 | 2014-04-16 | Infineum International Limited | Lubrification de moteur marin |
US20140360451A1 (en) * | 2013-06-06 | 2014-12-11 | James C. Dodd | Marine Engine Lubrication |
WO2017105948A1 (fr) * | 2015-12-15 | 2017-06-22 | The Lubrizol Corporation | Détergents de catécholate sulfuré pour compositions lubrifiantes |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9611318D0 (en) * | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
CN102690709B (zh) * | 2011-03-24 | 2013-12-25 | 中国石油化工股份有限公司 | 一种燃气发动机润滑油组合物 |
GB2498635A (en) * | 2011-12-21 | 2013-07-24 | Infineum Int Ltd | A method of reducing the rate of depletion of basicity of a lubricating oil composition for use in an engine |
-
2018
- 2018-09-20 EP EP18195639.2A patent/EP3470499B1/fr active Active
- 2018-10-15 CN CN201811193836.2A patent/CN109666525B/zh active Active
- 2018-10-16 JP JP2018195066A patent/JP2019073703A/ja active Pending
Patent Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3172892A (en) | 1959-03-30 | 1965-03-09 | Reaction product of high molecular weight succinic acids and succinic anhydrides with an ethylene poly- amine | |
US3219666A (en) | 1959-03-30 | 1965-11-23 | Derivatives of succinic acids and nitrogen compounds | |
US3024195A (en) | 1959-08-24 | 1962-03-06 | California Research Corp | Lubricating oil compositions of alkylpiperazine alkenyl succinimides |
US3202678A (en) | 1959-08-24 | 1965-08-24 | California Research Corp | Alkenyl succinimides of tetraethylene pentamine |
US3024237A (en) | 1959-08-24 | 1962-03-06 | California Research Corp | Alkenyl succinimides of piperazines |
US3254025A (en) | 1961-08-18 | 1966-05-31 | Lubrizol Corp | Boron-containing acylated amine and lubricating compositions containing the same |
US3087936A (en) | 1961-08-18 | 1963-04-30 | Lubrizol Corp | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
US3154560A (en) | 1961-12-04 | 1964-10-27 | Monsanto Co | Nu, nu'-azaalkylene-bis |
US3216936A (en) | 1964-03-02 | 1965-11-09 | Lubrizol Corp | Process of preparing lubricant additives |
US3801507A (en) | 1972-08-18 | 1974-04-02 | Chevron Res | Sulfurized metal phenates |
EP2719751A2 (fr) | 2012-06-07 | 2014-04-16 | Infineum International Limited | Lubrification de moteur marin |
EP2682451A1 (fr) | 2012-07-06 | 2014-01-08 | Infineum International Limited | Modification de détergent |
EP2682451B1 (fr) | 2012-07-06 | 2015-11-18 | Infineum International Limited | Modification de détergent |
US20140360451A1 (en) * | 2013-06-06 | 2014-12-11 | James C. Dodd | Marine Engine Lubrication |
WO2017105948A1 (fr) * | 2015-12-15 | 2017-06-22 | The Lubrizol Corporation | Détergents de catécholate sulfuré pour compositions lubrifiantes |
Non-Patent Citations (1)
Title |
---|
"Engine Oil Licensing and Certification System", December 1996, INDUSTRY SERVICES DEPARTMENT |
Also Published As
Publication number | Publication date |
---|---|
JP2019073703A (ja) | 2019-05-16 |
CN109666525A (zh) | 2019-04-23 |
EP3470499B1 (fr) | 2021-01-13 |
CN109666525B (zh) | 2022-05-17 |
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