US20140165943A1 - Marine Engine Lubrication - Google Patents

Marine Engine Lubrication Download PDF

Info

Publication number
US20140165943A1
US20140165943A1 US14/085,853 US201314085853A US2014165943A1 US 20140165943 A1 US20140165943 A1 US 20140165943A1 US 201314085853 A US201314085853 A US 201314085853A US 2014165943 A1 US2014165943 A1 US 2014165943A1
Authority
US
United States
Prior art keywords
oil
lubricating oil
basestock
mass
lubricating
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.)
Abandoned
Application number
US14/085,853
Other languages
English (en)
Inventor
James C. Dodd
Joshua L. Bradley-Shaw
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.)
Infineum International Ltd
Original Assignee
Infineum International Ltd
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 Infineum International Ltd filed Critical Infineum International Ltd
Publication of US20140165943A1 publication Critical patent/US20140165943A1/en
Assigned to INFINEUM INTERNATIONAL LIMITED reassignment INFINEUM INTERNATIONAL LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DODD, JAMES C., BRADLEY-SHAW, JOSHUA L.
Abandoned legal-status Critical Current

Links

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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • 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
    • C10M129/68—Esters
    • C10M129/72—Esters of polycarboxylic acids
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • 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
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
    • C10M129/54—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy 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
    • 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
    • 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
    • C10M169/045—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution and non-macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions used as base material
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C10M2207/127—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids polycarboxylic
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • 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
    • C10M2207/26—Overbased carboxylic acid salts
    • C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
    • 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
    • C10M2207/28—Esters
    • C10M2207/2805—Esters used as base material
    • 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
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • 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
    • C10N2030/78—Fuel contamination
    • 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

Definitions

  • This invention relates to a trunk piston marine engine lubricating composition for a medium-speed four-stroke compression-ignited (diesel) marine engine and lubrication of such an engine.
  • Heavy Fuel Oil is the heaviest fraction of petroleum distillate and comprises a complex mixture of molecules including up to 15% of asphaltenes, defined as the fraction of petroleum distillate that is insoluble in an excess of aliphatic hydrocarbon (e.g. heptane) but that is soluble in aromatic solvents (e.g. toluene). Asphaltenes can enter the engine lubricant as contaminants either via the cylinder or the fuel pumps and injectors, and asphaltene precipitation can then occur, manifested in ‘black paint’ or ‘black sludge’ in the engine.
  • asphaltenes can enter the engine lubricant as contaminants either via the cylinder or the fuel pumps and injectors, and asphaltene precipitation can then occur, manifested in ‘black paint’ or ‘black sludge’ in the engine.
  • trunk piston engine oils (‘TPEO's) prevent or inhibit asphaltene precipitation.
  • TPEO's using Group 1 basestocks may have the ability to solubilise asphaltenes.
  • TPEO's using high saturate basestocks e.g. Group II or III
  • WO 2010/115594 (“594”) and WO 2010/115595 (“595”) describe the use, in trunk piston marine engine lubricating oil compositions that contain 50 mass % or more of a Group II basestock, of respective minor amounts of a calcium salicylate detergent and of a polyalkenyl-substituted carboxylic and anhydride.
  • the data in “594” and “595” show that the combination gives rise to improved asphaltene dispersancy.
  • a problem in the art is to improve still further the asphaltene dispersancy performance of TPEO's that employ high saturate basestocks.
  • the invention meets the above problem by employing an anhydride and an ester in a TPEO: a synergistic effect is observed as demonstrated in the data herein.
  • a first aspect of the invention is a trunk piston marine engine lubricating oil composition for improving asphaltene handling in use thereof in operation of the engine when fuelled by a heavy fuel oil, which composition comprises or is made by admixing
  • a second aspect of the invention is a method of operating a trunk piston medium-speed compression-ignited marine engine comprising
  • a third aspect of the invention is a method of dispersing asphaltenes in a trunk piston marine lubricating oil composition during its lubrication of surfaces of the combustion chamber of a medium-speed compression-ignited marine engine and operation of the engine, which method comprises:
  • a fourth aspect of the invention is the use of detergent (B) in combination with component (C) as defined in and in the amounts stated in the first aspect of the invention in a trunk piston marine lubricating oil composition for a medium-speed compression-ignited marine engine, which composition comprises an oil of lubricating viscosity (A) in a major amount as defined in the first aspect of the invention, to provide comparable or improved asphaltene handling during operation of the engine, fuelled by a heavy fuel oil, and its lubrication by the composition, in comparison with that of a comparable oil where the basestock is a Group I basestock.
  • active ingredients or “(a.i.)” refers to additive material that is not diluent or solvent
  • KV100 means kinematic viscosity at 100° C. as measured by ASTM D445.
  • organic ester basestocks that include but are not limited to monoesters, diesters and polyolesters, and also polymer esters. They are generally considered to be Group V basestocks and are typically derived from animal or vegetable sources. Naturally-occurring organic esters can be found in animal fats or in vegetable oils. Organic esters can be synthesised by reacting organic acids with alcohols.
  • Monesters may be prepared by reacting monohydric alcohols with monobasic fatty acids to create a molecule with a single ester linkage and linear or branched alkyl groups.
  • Diesters may be prepared by reacting monohydric alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol) with dibasic acids (e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkylmalonic acids, alkenyl malonic acids) to create a molecule which may be linear, branched or aromatic with two ester groups.
  • monohydric alcohols e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol
  • 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.
  • Polyol esters may be prepared by esterifying one or more polyols such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol and tripentaerythritol with one or more organic acids such as C 5 to C 12 monocarboxylic acids. See, for example, U.S. Pat. No. 6,462,001.
  • polyol esters include trimethylolpropane (TMP) esters.
  • Tricarboxylic acid esters are also preferred.
  • the tricarboxylic acid ester is preferably a benzene tricarboxylic acid.
  • a preferred benzene tricarboxylic acid ester is 1,2,4-benzenetricarboxylic acid having alkyl chain lengths ranging from 5 to 10, preferably from 7 to 9.
  • a preferred 1,2,4-benzenetricarboxylic acid is trioctyl trimellitate.
  • ester basestocks for use in the present invention are those having a kinematic viscosity of 2 to 10 mm 2 s ⁇ 1 at 100° C. or those having a kinematic viscosity of greater than 10 to 100 mm 2 s ⁇ 1 at 100° C.
  • suitable polyol ester is Priolube® 3970, which is an ester of a neopentyl polyol, suitably TMP, with at least one aliphatic, saturated monocarboxylic acid and having 6 to 12 carbon atoms and a kinematic viscosity of 4.4 mm 2 s ⁇ 1 at 100° C.
  • the ester basestock may be present in an amount in the range of 2 to 85, preferably 5 to 50, more preferably 8 to 40 mass %.
  • viscosity may range in viscosity from light distillate mineral oil to heavy lubricating oil. Generally, the viscosity of the oil ranges from 2 to 40 mm 2 s ⁇ 1 , as measured at 100° C.
  • 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(1-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 derivative, analogues and homologues thereof.
  • 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.
  • a shale oil obtained directly from retorting operations; and petroleum oil obtained directly from distillation are unrefined oils.
  • Refined oils are similar to unrefined oils except that the oil is further treated in one or more purification steps to improve one or more properties.
  • Many such purification techniques such as distillation, solvent extraction, acid or base extraction, filtration and percolation, are known to those skilled in the art.
  • Re-refined oils are obtained by processes similar to those used to provide refined oils but begin with oil that has already been used in service. Such re-refined oils are also known as reclaimed or reprocessed oils and are often subjected to additional processing using techniques for removing spent additives and oil breakdown products.
  • Group I base stocks contain less than 90 percent saturates and/or greater than 0.03 percent sulphur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in Table E-1.
  • Group II base stocks contain greater than or equal to 90 percent saturates and less than or equal to 0.03 percent sulphur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in Table E-1.
  • Group III base stocks contain greater than or equal to 90 percent saturates and less than or equal to 0.03 percent sulphur and have a viscosity index greater than or equal to 120 using the test methods specified in Table E-1.
  • Group IV base stocks are polyalphaolefins (PAO).
  • Group V base stocks include all other base stocks not included in Group I, II, III, or IV.
  • the basestocks (A2) embraces Group II, Group III and Group IV basestocks and also basestocks derived from hydrocarbons synthesised by the Fischer-Tropsch process.
  • synthesis gas containing carbon monoxide and hydrogen or ‘syngas’
  • hydrocarbons typically require further processing in order to be useful as a base oil.
  • they may, by methods known in the art, be hydroisomerized; hydrocracked and hydroisomerized; dewaxed; or hydroisomerized and dewaxed.
  • 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 basestock (A2) when used in this invention, contains 50 mass % or more of the defined basestock or a mixture thereof. Preferably, it contains 60, such as 70, 80 or 90, mass % or more of the defined basestock or a mixture thereof. (A2) may comprise substantially all the defined basestock or a mixture thereof.
  • a metal detergent is an additive based on so-called metal “soaps”, that is metal salts of acidic organic compounds, sometimes referred to as surfactants. They generally comprise a polar head with a long hydrophobic tail.
  • Overbased metal detergents which comprise neutralized metal detergents as the outer layer of a metal base (e.g. carbonate) micelle, may be provided by including large amounts of metal base by reacting an excess of a metal base, such as an oxide or hydroxide, with an acidic gas such as carbon dioxide.
  • a metal base e.g. carbonate
  • detergents include metal salicylates, phenates and salicylates and combinations thereof.
  • overbased metal detergents (B) are preferably overbased metal hydrocarbyl-substituted hydroxybenzoate, more preferably hydrocarbyl-substituted salicylate, detergents.
  • the metal may be an alkali metal (e.g. Li, Na, K) or an alkaline earth metal (e.g. Mg, Ca).
  • Hydrocarbyl means a group or radical that contains carbon and hydrogen atoms and that is bonded to the remainder of the molecule via a carbon atom. It may contain hetero atoms, i.e. atoms other than carbon and hydrogen, provided they do not alter the essentially hydrocarbon nature and characteristics of the group.
  • hydrocarbyl there may be mentioned alkyl and alkenyl.
  • a preferred overbased metal hydrocarbyl-substituted hydroxybenzoate is a calcium alkyl-substituted salicylate and has the structure shown:
  • R is a linear alkyl group.
  • R group There may be more than one R group attached to the benzene ring.
  • the COO ⁇ group can be in the ortho, meta or para position with respect to the hydroxyl group; the ortho position is preferred.
  • the R group can be in the ortho, meta or para position with respect to the hydroxyl group.
  • Salicylic acids are typically prepared by the carboxylation, by the Kolbe-Schmitt process, of phenoxides, and in that case will generally be obtained (normally in a diluent) in admixture with uncarboxylated phenol. Salicylic acids may be non-sulphurized or sulphurized, and may be chemically modified and/or contain additional substituents. Processes for sulphurizing an alkyl salicylic acid are well known to those skilled in the art, and are described in, for example, US 2007/0027057.
  • the alkyl groups advantageously contain 5 to 100, preferably 9 to 30, especially 14 to 24, carbon atoms.
  • overbased is generally used to describe metal detergents in which the ratio of the number of equivalents of the metal moiety to the number of equivalents of the acid moiety is greater than one.
  • low-based is used to describe metal detergents in which the equivalent ratio of metal moiety to acid moiety is greater than 1, and up to about 2.
  • an “overbased calcium salt of surfactants” is meant an overbased detergent in which the metal cations of the oil-insoluble metal salt are essentially calcium cations. Small amounts of other cations may be present in the oil-insoluble metal salt, but typically at least 80, more typically at least 90, for example at least 95, mole % of the cations in the oil-insoluble metal salt, are calcium ions. Cations other than calcium may be derived, for example, from the use in the manufacture of the overbased detergent of a surfactant salt in which the cation is a metal other than calcium.
  • the metal salt of the surfactant is also calcium.
  • Carbonated overbased metal detergents typically comprise amorphous nanoparticles. Additionally, the art discloses nanoparticulate materials comprising carbonate in the crystalline calcite and vaterite forms.
  • the basicity of the detergents may be expressed as a total base number (TBN), sometimes referred to as base number (BN).
  • TBN total base number
  • BN base number
  • a total base number is the amount of acid needed to neutralize all of the basicity of the overbased material.
  • the TBN may be measured using ASTM standard D2896 or an equivalent procedure.
  • the detergent may have a low TBN (i.e. a TBN of less than 50), a medium TBN (i.e. a TBN of 50 to 150) or a high TBN (i.e. a TBN of greater than 150, such as 150-500).
  • the bascicity may also be expressed as basicity index (BI), which is the molar ratio of total base to total soap in the overbased detergent.
  • the anhydride may constitute at least 1 to 7, preferably 2 to 6 mass % of the lubricating oil composition. Preferably it constitutes 3 to 5, even more preferably 4 to 5, mass %.
  • the anhydride may be mono or polycarboxylic, preferably dicarboxylic.
  • the polyalkenyl group preferably has from 8 to 400, such as 8 to 100, carbon atoms.
  • R 1 represents a C 8 to C 100 branched or linear polyalkenyl group.
  • the polyalkenyl moiety may have a number average molecular weight of from 200 to 3000, preferably from 350 to 950.
  • Suitable hydrocarbons or polymers employed in the formation of the anhydrides used in the present invention to generate the polyalkenyl moieties include homopolymers, interpolymers or lower molecular weight hydrocarbons.
  • One family of such polymers comprise polymers of ethylene and/or at least one C 3 to C 28 alpha-olefin having the formula H 2 C ⁇ CHR 1 wherein R 1 is straight or branched-chain alkyl radical comprising 1 to 26 carbon atoms and wherein the polymer contains carbon-to-carbon unsaturation, preferably a high degree of terminal ethenylidene unsaturation.
  • such polymers comprise interpolymers of ethylene and at least one alpha-olefin of the above formula, wherein R 1 is alkyl of from 1 to 18 carbon atoms, and more preferably is alkyl of from 1 to 8 carbon atoms, and more preferably still of from 1 to 2 carbon atoms.
  • useful alpha-olefin monomers and comonomers include, for example, propylene, butene-1, hexene-1, octene-1,4-methylpentene-1, decene-1, dodecene-1, tridecene-1, tetradecene-1, pentadecene-1, hexadecene-1, heptadecene-1, octadecene-1, nonadecene-1, and mixtures thereof (e.g., mixtures of propylene and butene-1, and the like).
  • Exemplary of such polymers are propylene homopolymers, butene-1 homopolymers, ethylene-propylene copolymers, ethylene-butene-1 copolymers, propylene-butene copolymers and the like, wherein the polymer contains at least some terminal and/or internal unsaturation.
  • Preferred polymers are unsaturated copolymers of ethylene and propylene and ethylene and butene-1.
  • the interpolymers may contain a minor amount, e.g. 0.5 to 5 mole %, of a C 4 to C 18 non-conjugated diolefin comonomer.
  • the polymers comprise only alpha-olefin homopolymers, interpolymers of alpha-olefin comonomers and interpolymers of ethylene and alpha-olefin comonomers.
  • the molar ethylene content of the polymers employed is preferably in the range of 0 to 80%, and more preferably 0 to 60%.
  • the ethylene content of such copolymers is most preferably between 15 and 50%, although higher or lower ethylene contents may be present.
  • These polymers may be prepared by polymerizing an alpha-olefin monomer, or mixtures of alpha-olefin monomers, or mixtures comprising ethylene and at least one C 3 to C 28 alpha-olefin monomer, in the presence of a catalyst system comprising at least one metallocene (e.g., a cyclopentadienyl-transition metal compound) and an alumoxane compound.
  • a catalyst system comprising at least one metallocene (e.g., a cyclopentadienyl-transition metal compound) and an alumoxane compound.
  • the percentage of polymer chains exhibiting terminal ethenylidene unsaturation may be determined by FTIR spectroscopic analysis, titration, or C 13 NMR.
  • Interpolymers of this latter type may be characterized by the formula POLY-C(R 1 ) ⁇ CH 2 wherein R 1 is C 1 to C 26 alkyl, preferably C 1 to C 18 alkyl, more preferably C 1 to C 8 alkyl, and most preferably C 1 to C 2 alkyl, (e.g., methyl or ethyl) and wherein POLY represents the polymer chain.
  • the chain length of the R 1 alkyl group will vary depending on the comonomer(s) selected for use in the polymerization.
  • a minor amount of the polymer chains can contain terminal ethenyl, i.e., vinyl, unsaturation, i.e. POLY-CH ⁇ CH 2 , and a portion of the polymers can contain internal monounsaturation, e.g. POLY-CH ⁇ CH(R 1 ), wherein R 1 is as defined above.
  • terminally unsaturated interpolymers may be prepared by known metallocene chemistry and may also be prepared as described in U.S. Pat. Nos. 5,498,809; 5,663,130; 5,705,577; 5,814,715; 6,022,929 and 6,030,930.
  • Another useful class of polymers is that of polymers prepared by cationic polymerization of isobutene, styrene, and the like.
  • Common polymers from this class include polyisobutenes obtained by polymerization of a C 4 refinery stream having a butene content of 35 to 75 mass %, and an isobutene content of 30 to 60 mass %, in the presence of a Lewis acid catalyst, such as aluminum trichloride or boron trifluoride.
  • a preferred source of monomer for making poly-n-butenes is petroleum feedstreams such as Raffinate II. These feedstocks are disclosed in the art such as in U.S. Pat. No. 4,952,739.
  • Polyisobutylene is a most preferred backbone because it is readily available by cationic polymerization from butene streams (e.g., using AlCl 3 or BF 3 catalysts). Such polyisobutylenes generally contain residual unsaturation in amounts of one ethylenic double bond per polymer chain, positioned along the chain.
  • a preferred embodiment utilizes polyisobutylene prepared from a pure isobutylene stream or a Raffinate I stream to prepare reactive isobutylene polymers with terminal vinylidene olefins.
  • these polymers referred to as highly reactive polyisobutylene (HR-PIB)
  • HR-PIB highly reactive polyisobutylene
  • these polymers have a terminal vinylidene content of at least 65%, e.g., 70%, more preferably at least 80%, most preferably, at least 85%.
  • the preparation of such polymers is described, for example, in U.S. Pat. No. 4,152,499.
  • HR-PIB is known and HR-PIB is commercially available under the tradenames GlissopalTM (from BASF) and UltravisTM (from BP-Amoco).
  • Polyisobutylene polymers that may be employed are generally based on a hydrocarbon chain of from 400 to 3000. Methods for making polyisobutylene are known. Polyisobutylene can be functionalized by halogenation (e.g. chlorination), the thermal “ene” reaction, or by free radical grafting using a catalyst (e.g. peroxide), as described below.
  • halogenation e.g. chlorination
  • the thermal “ene” reaction e.g. peroxide
  • a catalyst e.g. peroxide
  • the hydrocarbon or polymer backbone may be functionalized with carboxylic anhydride-producing moieties selectively at sites of carbon-to-carbon unsaturation on the polymer or hydrocarbon chains, or randomly along chains using any of the three processes mentioned above or combinations thereof, in any sequence.
  • the polymer or hydrocarbon may be functionalized, with carboxylic acid anhydride moieties by reacting the polymer or hydrocarbon under conditions that result in the addition of functional moieties or agents, i.e., acid anhydride, onto the polymer or hydrocarbon chains primarily at sites of carbon-to-carbon unsaturation (also referred to as ethylenic or olefinic unsaturation) using the halogen assisted functionalization (e.g. chlorination) process or the thermal “ene” reaction.
  • halogen assisted functionalization e.g. chlorination
  • Selective functionalization can be accomplished by halogenating, e.g., chlorinating or brominating, the unsaturated ⁇ -olefin polymer to 1 to 8, preferably 3 to 7, mass % chlorine, or bromine, based on the weight of polymer or hydrocarbon, by passing the chlorine or bromine through the polymer at a temperature of 60 to 250° C., preferably 110 to 160° C., e.g., 120 to 140° C., for 0.5 to 10, preferably 1 to 7 hours.
  • halogenating e.g., chlorinating or brominating
  • the halogenated polymer or hydrocarbon (hereinafter backbone) is then reacted with sufficient monounsaturated reactant capable of adding the required number of functional moieties to the backbone, e.g., monounsaturated carboxylic reactant, at 100 to 250° C., usually 180° C. to 235° C., for 0.5 to 10, e.g., 3 to 8 hours, such that the product obtained will contain the desired number of moles of the monounsaturated carboxylic reactant per mole of the halogenated backbones.
  • the backbone and the monounsaturated carboxylic reactant are mixed and heated while adding chlorine to the hot material.
  • chlorination normally helps increase the reactivity of starting olefin polymers with monounsaturated functionalizing reactant, it is not necessary with some of the polymers or hydrocarbons contemplated for use in the present invention, particularly those preferred polymers or hydrocarbons which possess a high terminal bond content and reactivity.
  • the backbone and the monounsaturated functionality reactant, (carboxylic reactant) are contacted at elevated temperature to cause an initial thermal “ene” reaction to take place. Ene reactions are known.
  • the hydrocarbon or polymer backbone can be functionalized by random attachment of functional moieties along the polymer chains by a variety of methods.
  • the polymer in solution or in solid form, may be grafted with the monounsaturated carboxylic reactant, as described above, in the presence of a free-radical initiator.
  • the grafting takes place at an elevated temperature in the range of 100 to 260° C., preferably 120 to 240° C.
  • free-radical initiated grafting would be accomplished in a mineral lubricating oil solution containing, e.g., 1 to 50, preferably 5 to 30, mass % polymer based on the initial total oil solution.
  • the free-radical initiators that may be used are peroxides, hydroperoxides, and azo compounds, preferably those that have a boiling point greater than 100° C. and decompose thermally within the grafting temperature range to provide free-radicals.
  • Representative of these free-radical initiators are azo butyronitrile, 2,5-dimethylhex-3-ene-2,5-bis-tertiary-butyl peroxide and dicumene peroxide.
  • the initiator, when used, is typically in an amount of between 0.005% and 1% by weight based on the weight of the reaction mixture solution.
  • the aforesaid monounsaturated carboxylic reactant material and free-radical initiator are used in a weight ratio range of from 1.0:1 to 30:1, preferably 3:1 to 6:1.
  • the grafting is preferably carried out in an inert atmosphere, such as under nitrogen blanketing.
  • the resulting grafted polymer is characterized by having carboxylic acid (or derivative) moieties randomly attached along the polymer chains, it being understood, of course, that some of the polymer chains remain ungrafted.
  • the free radical grafting described above can be used for the other polymers and hydrocarbons used in the present invention.
  • the preferred monounsaturated reactants that are used to functionalize the backbone comprise mono- and dicarboxylic acid material, i.e., acid, or acid derivative material, including (i) monounsaturated C 4 to C 10 dicarboxylic acid wherein (a) the carboxyl groups are vicinyl, (i.e., located on adjacent carbon atoms) and (b) at least one, preferably both, of the adjacent carbon atoms are part of the mono unsaturation; (ii) derivatives of (i) such as anhydrides or C 1 to C 5 alcohol derived mono- or diesters of (i); (iii) monounsaturated C 3 to C 10 monocarboxylic acid wherein the carbon-carbon double bond is conjugated with the carboxy group, i.e., of the structure —C ⁇ C—CO—; and (iv) derivatives of (iii) such as C 1 to C 5 alcohol derived mono- or diesters of (iii).
  • Mixtures of monounsaturated carboxylic materials (i)-(iv) also may be used.
  • the monounsaturation of the monounsaturated carboxylic reactant becomes saturated.
  • maleic anhydride becomes backbone-substituted succinic anhydride
  • acrylic acid becomes backbone-substituted propionic acid.
  • Such monounsaturated carboxylic reactants are fumaric acid, itaconic acid, maleic acid, maleic anhydride, chloromaleic acid, chloromaleic anhydride, acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, and lower alkyl (e.g., C 1 to C 4 alkyl) acid esters of the foregoing, e.g., methyl maleate, ethyl fumarate, and methyl fumarate.
  • lower alkyl e.g., C 1 to C 4 alkyl
  • the monounsaturated carboxylic reactant typically will be used in an amount ranging from equimolar amount to 100 mass % excess, preferably 5 to 50 mass % excess, based on the moles of polymer or hydrocarbon. Unreacted excess monounsaturated carboxylic reactant can be removed from the final dispersant product by, for example, stripping, usually under vacuum, if required.
  • the lubricating oil composition of the invention may comprise further additives, different from and additional to (B) and (C).
  • additional additives may, for example include ashless dispersants, other metal detergents, anti-wear agents such as zinc dihydrocarbyl dithiophosphates, anti-oxidants and demulsifiers. In some cases, an ashless dispersant need not be provided.
  • additives (B) and (C) can be added simultaneously to the base oil to form the lubricating oil composition. Dissolution of the additive package(s) into the lubricating oil may be facilitated by solvents and by mixing accompanied with mild heating, but this is not essential.
  • the additive package(s) will typically be formulated to contain the additive(s) in proper amounts to provide the desired concentration, and/or to carry out the intended function in the final formulation when the additive package(s) is/are combined with a predetermined amount of base oil.
  • additives (B) and (C), in accordance with the present invention may be admixed with small amounts of base oil or other compatible solvents together with other desirable additives to form additive packages containing active ingredients in an amount, based on the additive package, of, for example, from 2.5 to 90, preferably from 5 to 75, most preferably from 8 to 60, mass % of additives in the appropriate proportions, the remainder being base oil.
  • the final formulation as a trunk piston engine oil may typically contain 30, preferably 10 to 28, more preferably 12 to 24, mass % of the additive package(s), the remainder being base oil.
  • the trunk piston engine oil may have a compositional TBN (using ASTM D2896) of 20 to 60, such as, 30 to 55. For example, it may be 40 to 55 or 35 to 50.
  • Trunk Piston Marine Engine Lubricating Oils TPEO's
  • Test trunk piston marine engine lubricating oils were evaluated for asphaltene dispersancy using light scattering according to the Focused Beam Reflectance Method (“FBRM”), which predicts asphaltene agglomeration and hence ‘black sludge’ formation.
  • FBRM Focused Beam Reflectance Method
  • the FBRM test method was disclosed at the 7 th International Symposium on Marine Engineering, Tokyo, 24 th -28 th Oct. 2005, and was published in “The Benefits of Salicylate Detergents in TPEO Applications with a Variety of Base Stocks” in the Conference Proceedings. Further details were disclosed at the CIMAC Congress, Vienna, 21 St -24 May 2007 and published in “Meeting the Challenge of New Base Fluids for the Lubrication of Medium Speed Marine Engines—An Additive Approach” in the Congress Proceedings.
  • the FBRM probe contains fibre optic cables through which laser light travels to reach the probe tip. At the tip, an optic focuses the laser light to a small spot. The optic is rotated so that the focussed beam scans a circular path between the window of the probe and the sample. As particles flow past the window, they intersect the scanning path giving backscattered light from the individual particles.
  • the scanning laser beam travels much faster than the particles; this means that the particles are effectively stationary. As the focussed beam reaches one edge of the particle, the amount of backscattered light increases; the amount will decrease when the focussed beam reaches the other edge of the particle.
  • the instrument measures the time of the increased backscatter.
  • the time period of backscatter from one particle is multiplied by the scan speed and the result is a distance or chord length.
  • a chord length is a straight line between any two points on the edge of a particle. This is represented as a chord length distribution, a graph of numbers of chord lengths (particles) measured as a function of the chord length dimensions in microns.
  • FBRM typically measures tens of thousands of chords per second, resulting in a robust number-by-chord length distribution. The method gives an absolute measure of the particle size distribution of the asphaltene particles.
  • the Focused beam Reflectance Probe (FBRM), model Lasentec D600L, was supplied by Mettler Toledo, Leicester, UK. The instrument was used in a configuration to give a particle size resolution of 1 ⁇ m to 1 mm. Data from FBRM can be presented in several ways. Studies have suggested that the average counts per second can be used as a quantitative determination of asphaltene dispersancy. This value is a function of both the average size and level of agglomerate. In this application, the average count rate (over the entire size range) was monitored using a measurement time of 1 second per sample.
  • test TPEO's were heated to 60° C. and stirred at 400 rpm; when the temperature reached 60° C. the FBRM probe was inserted into the sample and measurements made for 15 minutes.
  • An aliquot of heavy fuel oil (10% w/w) was introduced into the TPEO under stirring using a four-blade stirrer (at 400 rpm). A value for the average counts per second was taken when the count rate had reached an equilibrium value (typically overnight).
  • Each TPEO tested had a BN of 40, contained 1.23 mass % (in terms of calcium) of calcium salicylate of BI 8.0 and 0.24 mass % (in terms of calcium) of calcium salicylate of BI 3.0, and contained the same amount of Zn and of silicone antifoam.
  • Each TPEO tested had a BN of 40, contained 0.75 mass % (in terms of calcium) of calcium salicylate of BI 8.0 and 0.68 mass % (in terms of calcium) of calcium salicylate of BI 3.0, and contained the same amount of Zn.
  • Example 14 shows the applicability of the invention to a Group III base oil eyond that of Ref 6 (a Group I oil) and Example 15 shows the applicability of the invention to esters other than Priolube 3970.
  • Each TPEO treated had a BN of 30, contained 0.56 mass % (in terms of calcium) of calcium salicylate of BI 8.0 and 0.51 mass % (in terms of calcium) of calcium salicylate of BI 3.0, and contained the same amount of Zn.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
US14/085,853 2012-11-21 2013-11-21 Marine Engine Lubrication Abandoned US20140165943A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12193607 2012-11-21
EP12193607.4 2012-11-21

Publications (1)

Publication Number Publication Date
US20140165943A1 true US20140165943A1 (en) 2014-06-19

Family

ID=47189824

Family Applications (1)

Application Number Title Priority Date Filing Date
US14/085,853 Abandoned US20140165943A1 (en) 2012-11-21 2013-11-21 Marine Engine Lubrication

Country Status (10)

Country Link
US (1) US20140165943A1 (fr)
EP (1) EP2735603B1 (fr)
JP (1) JP6279888B2 (fr)
KR (1) KR102160538B1 (fr)
CN (1) CN103834458A (fr)
AU (1) AU2013260695B2 (fr)
CA (1) CA2833977C (fr)
DK (1) DK2735603T3 (fr)
ES (1) ES2586531T3 (fr)
SG (1) SG2013085915A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140128301A1 (en) * 2012-11-02 2014-05-08 Infineum International Limited Marine engine lubrication
US11066614B2 (en) * 2018-12-20 2021-07-20 Infineum International Limited Hydrocarbon marine fuel oil
US11198831B2 (en) * 2019-01-31 2021-12-14 Kvi Llc Lubricant for a device

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2620681T3 (es) * 2014-12-04 2017-06-29 Infineum International Limited Lubricación de motores marinos
US10160926B2 (en) * 2016-11-25 2018-12-25 Hyundai Motor Company Axle oil composition having enhanced fuel efficiency and low viscosity
FR3159974A1 (fr) 2024-03-06 2025-09-12 Totalenergies Onetech Utilisation d’une composition lubrifiante dans un moteur à combustion à ammoniac

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090305924A1 (en) * 2006-08-07 2009-12-10 Alexandra Mayhew Method of Lubricating an Internal Combustion Engine
US20110077179A1 (en) * 2009-09-29 2011-03-31 Chevron Oronite Technology B.V. Trunk piston engine lubricating oil compositions
US20110319304A1 (en) * 2010-06-29 2011-12-29 Chevron Oronite Technology B.V. Trunk piston engine lubricating oil compositions
US20120028522A1 (en) * 2009-04-07 2012-02-02 Terence Garner Marine engine lubrication

Family Cites Families (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1248643B (de) 1959-03-30 1967-08-31 The Lubrizol Corporation, Cleveland, Ohio (V. St. A.) Verfahren zur Herstellung von öllöslichen aeylierten Aminen
US3231587A (en) 1960-06-07 1966-01-25 Lubrizol Corp Process for the preparation of substituted succinic acid compounds
US3215707A (en) 1960-06-07 1965-11-02 Lubrizol Corp Lubricant
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
US3381022A (en) 1963-04-23 1968-04-30 Lubrizol Corp Polymerized olefin substituted succinic acid esters
NL296139A (fr) 1963-08-02
US3574576A (en) 1965-08-23 1971-04-13 Chevron Res Distillate fuel compositions having a hydrocarbon substituted alkylene polyamine
US3272746A (en) 1965-11-22 1966-09-13 Lubrizol Corp Lubricating composition containing an acylated nitrogen compound
US3442808A (en) 1966-11-01 1969-05-06 Standard Oil Co Lubricating oil additives
US3912764A (en) 1972-09-29 1975-10-14 Cooper Edwin Inc Preparation of alkenyl succinic anhydrides
US4110349A (en) 1976-06-11 1978-08-29 The Lubrizol Corporation Two-step method for the alkenylation of maleic anhydride and related compounds
DE2702604C2 (de) 1977-01-22 1984-08-30 Basf Ag, 6700 Ludwigshafen Polyisobutene
US4234435A (en) 1979-02-23 1980-11-18 The Lubrizol Corporation Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation
US4952739A (en) 1988-10-26 1990-08-28 Exxon Chemical Patents Inc. Organo-Al-chloride catalyzed poly-n-butenes process
CA1335895C (fr) 1989-02-07 1995-06-13 Exxon Chemical Patents Inc. Methode basse temperature utilisant un melange en zone multiple pour l'obtention de derives de substitution par une longue chaine hydrocarbylee d'acides mono- ou dicarboxyliques
CA1338288C (fr) 1989-02-07 1996-04-30 Jai Gopal Bansal Methode de preparation de derives de substitution hydrocarbyles a longue chaine d'acides dicarboxyliques
IL107927A0 (en) 1992-12-17 1994-04-12 Exxon Chemical Patents Inc Oil soluble ethylene/1-butene copolymers and lubricating oils containing the same
CA2110654C (fr) 1992-12-17 2006-03-21 Albert Rossi Procede pour la polymerisation d'un copolymere ethylene-alpha-olefine utilisant des catalyseurs a base de metallocene, en milieu dilue
TW291486B (fr) 1992-12-17 1996-11-21 Exxon Chemical Patents Inc
GB9503993D0 (en) * 1995-02-28 1995-04-19 Bp Chem Int Ltd Lubricating oil compositions
US5777025A (en) 1996-02-09 1998-07-07 Exxon Chemical Patents Inc. Process for preparing polyalkenyl substituted C4 to C10 dicarboxylic acid producing materials
US5891953A (en) 1996-02-09 1999-04-06 Exxon Chemical Patents Inc Process for preparing polyalkenyl substituted mono- and dicarboxylic acid producing materials (PT-1302)
DE69816843T2 (de) 1997-10-01 2004-04-15 Unichema Chemie B.V. Komplexaster, diese enthaltende zusammensetzungen und ihre verwendung
EP1197545A1 (fr) * 2000-10-13 2002-04-17 Infineum International Limited Compositions d'huile lubrifiante
US20040121918A1 (en) * 2002-07-08 2004-06-24 Salvatore Rea Lubricating oil composition for marine engines
US7956022B2 (en) 2005-07-29 2011-06-07 Chevron Oronite Company Llc Low sulfur metal detergent-dispersants
EP2048218A1 (fr) 2007-10-09 2009-04-15 Infineum International Limited Composition d'huile de lubrification
EP2424965B1 (fr) * 2009-05-01 2015-05-20 Infineum International Limited Lubrification de moteur marin
DK2447346T3 (en) 2010-10-28 2014-03-24 Infineum Int Ltd Lubricating a marine engine

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090305924A1 (en) * 2006-08-07 2009-12-10 Alexandra Mayhew Method of Lubricating an Internal Combustion Engine
US20120028522A1 (en) * 2009-04-07 2012-02-02 Terence Garner Marine engine lubrication
US20110077179A1 (en) * 2009-09-29 2011-03-31 Chevron Oronite Technology B.V. Trunk piston engine lubricating oil compositions
US20110319304A1 (en) * 2010-06-29 2011-12-29 Chevron Oronite Technology B.V. Trunk piston engine lubricating oil compositions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140128301A1 (en) * 2012-11-02 2014-05-08 Infineum International Limited Marine engine lubrication
US11066614B2 (en) * 2018-12-20 2021-07-20 Infineum International Limited Hydrocarbon marine fuel oil
US11198831B2 (en) * 2019-01-31 2021-12-14 Kvi Llc Lubricant for a device

Also Published As

Publication number Publication date
EP2735603B1 (fr) 2016-06-08
AU2013260695A1 (en) 2014-06-05
SG2013085915A (en) 2014-06-27
AU2013260695B2 (en) 2017-03-02
CN103834458A (zh) 2014-06-04
CA2833977C (fr) 2020-04-21
EP2735603A1 (fr) 2014-05-28
JP2014101513A (ja) 2014-06-05
CA2833977A1 (fr) 2014-05-21
ES2586531T3 (es) 2016-10-17
JP6279888B2 (ja) 2018-02-14
KR102160538B1 (ko) 2020-09-28
KR20140065350A (ko) 2014-05-29
DK2735603T3 (en) 2016-08-29

Similar Documents

Publication Publication Date Title
EP2417234B1 (fr) Lubrification de moteurs marins
EP2735603B1 (fr) Lubrification de moteur marin
EP2765179B1 (fr) Lubrification de moteur marin
EP2727984B1 (fr) Lubrification de moteur marin
US9534185B2 (en) Marine engine lubrication
CA2913603C (fr) Lubrification de moteur marin
US10364404B2 (en) Marine engine lubrication
US9879202B2 (en) Marine engine lubrication

Legal Events

Date Code Title Description
AS Assignment

Owner name: INFINEUM INTERNATIONAL LIMITED, UNITED KINGDOM

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:DODD, JAMES C.;BRADLEY-SHAW, JOSHUA L.;SIGNING DATES FROM 20140113 TO 20140117;REEL/FRAME:036966/0982

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION