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
  • 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
  • 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
  • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen 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
  • 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
  • C10M2205/022—Ethene
• • 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
  • C10M2205/024—Propene
• • 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
  • C10M2205/026—Butene
• • 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
• • 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
  • C10M2205/08—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing non-conjugated dienes
• • 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
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
  • C10M2209/084—Acrylate; Methacrylate
• • 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
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
  • C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
• • 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
  • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
  • C10N2020/01—Physico-chemical properties
  • C10N2020/04—Molecular weight; Molecular weight distribution
• • 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
  • C10N2030/08—Resistance to extreme temperature

Definitions

• the present invention relates to lubricant compositions having improved flow properties, particularly lubricant compositions comprising American Petroleum Institute (API) Group III base stocks which exhibit improved low temperature flow properties.
• API American Petroleum Institute
• Lubricant compositions are used in various applications such as automotive applications, industrial applications, etc. Lubricant compositions are typically formulated from a base stock and one or more additives.
• additives for use in lubricant compositions are well known in the art.
• additives include, but are not limited to, lube oil flow improvers (LOFIs), viscosity modifiers (VMs), etc.
• LOFIs lube oil flow improvers
• VMs viscosity modifiers
• WO98/28386A disclose (di)alkyl fumarate-vinyl acetate copolymers for use as a lube oil flow improver.
• the present invention provides a lubricant composition having improved low temperature flow performance properties comprising (a) an API Group III base stock; (b) a semi-crystalline viscosity modifier; and (c) one or more LOFIs having a side-chain distribution which satisfies certain requirements.
• the present invention provides a lubricant composition
• a lubricant composition comprising (a) an API Group III base stock;
• the lubricant composition comprises an automotive lubricating oil composition, more especially an automotive lubricating oil composition for use in piston engines, especially gasoline (spark-ignited) and diesel (compression-ignited), crankcase lubrication, such compositions being referred to as crankcase lubricants.
• the present invention provides a method of lubricating a compression-ignited or spark-ignited combustion engine, comprising operating the engine with a lubricant composition according to the first aspect of the invention.
• the method according to the second aspect of the present invention comprises lubricating the crankcase of a compression-ignited or spark-ignited internal combustion engine.
• the present invention provides the use, in a lubricant composition which comprises an API Group III base stock, of (b) a semi-crystalline viscosity modifier as defined in accordance with the first aspect of the present invention; in combination with (c) one or more LOFIs as defined in accordance with the first aspect of the present invention, to improve the low temperature flow properties of the lubricant composition.
• the low temperature flow properties of the lubricant composition are measured using the MRV Pumpability Test according to ASTM D4684.
• the use in accordance with the third aspect of the present invention enables the lubricant composition to pass the MRV Pumpability Test according to ASTM D4684.
• lubricant composition as used herein represents a “lubricating oil composition”.
• polymer includes copolymers unless otherwise specifically stated to be limited to a polymer derived solely from the polymerization of a single monomer and encompasses branched as well as linear polymers.
• copolymer refers to a polymer resulting from the polymerization reaction of two chemically different monomers.
• ethylene alphaolefin copolymers it is understood that such copolymers can optionally contain a minor amount (for example, greater than zero but less than 10% by weight) of a nonconjugated polyene, in which case the copolymer is sometimes referred to as a terpolymer.
• ethylene alphaolefin polymers it is understood both copolymers and terpolymers of ethylene with at least one other alpha-olefin are included.
• average carbon number refers to the average carbon number weighted by molar fraction.
• lubricating oil flow improver covers all additives which modify the size, number, and growth of wax crystals in lubricating (or lube for short) oils in such a way as to impart improved low temperature handling, pumpability, and/or vehicle operability as measured by such tests as pour point, Mini-Rotary Viscometer (MRV), and Scanning Brookfield Viscometer.
• the majority of lubricating oil flow improvers are polymers or copolymers, or contain polymers or copolymers. These polymers are generally side chain, backbone or mixtures thereof.
• base oil refers to a refined fluid that is free of additives and is used as a component in a lubricant blend.
• base stock refers to a blend, mixture, or similar of base oils.
• bi-modal refers to a carbon chain length frequency distribution which has two distinct peaks (or modes) with each peak being a carbon chain length (or carbon chain lengths adjacent in terms of sequential even number of carbons) which has a higher mole percentage than neighboring carbon chain lengths.
• the bi-modal carbon chain length frequency distribution has a "lower portion of the distribution” and an "upper portion of the distribution”.
• lower portion of the distribution refers to the portion of the bi-modal distribution which is composed of the mode with the lower carbon chain length (or lengths) and adjacent carbon chain lengths (in terms of sequential even number chain lengths) of lower mole percent.
• the highest carbon chain length in the lower portion of the distribution is C 14 .
• upper portion of the distribution refers to the portion of the bi-modal distribution which is composed of the mode with the higher carbon chain length (or lengths) and adjacent carbon chain lengths of lower mole percent.
• the lowest carbon chain length in the upper portion of the distribution is C 16 .
• primarily means the amount of one component present in the composition, compound, etc. is more than the amounts of any other component present on a component-by-component basis.
• the lubricant composition comprises (a) a Group III base stock; (b) a semi-crystalline viscosity modifier; and (c) one or more LOFIs that meet certain specifications.
• the lubricant composition comprises an API Group III base stock.
• Group III base stocks as defined by the API have a viscosity index that is open-ended.
• the viscosity index of the base stock is greater than 120.
• the base stocks has a viscosity index of equal to or greater than 120 and equal to or less than 200.
• Suitable, commercially available Group III base stocks include, but are not limited to: the Visom brand of base stocks commercially available from ExxonMobil (Fawley, U.K.); the Yubase brand of base stocks commercially available from SK Corporation (Ulsan, South Korea); the Ultra-S brand of base stocks are commercially available from ConocoPhillips (Westlake, LA (USA)); and the Nexbase brand of base stocks commercially available from Neste (Porvoo, Finland).
• the base stock is made using gas-to-liquids (“GTL”) process.
• GTL gas-to-liquids
• GTL is a refinery process used to convert natural gas or other gaseous hydrocarbons into longer-chain hydrocarbons.
• GTL can be used to convert methane-rich gases into liquid fuels either via direct conversion or via syngas as an intermediate using the Fischer Tropsch process.
• isomerization catalyst can be used with GTL to make Group III base stocks
• the lubricant composition comprises a semi-crystalline viscosity modifier.
• the semi-crystalline viscosity modifier comprises one or more high molecular weight hydrocarbon polymers as is well known in the art.
• suitable hydrocarbon polymers include copolymers of ethylene copolymerized with at least one additional alphaolefin monomer having from 3 to 30, for example, from 3 to 8 carbon atoms and which may be straight or branched.
• a low concentration, e.g., less than about 10 wt. %, of a nonconjugated diene can be present.
• these copolymers are those comprising ethylene and propylene.
• Ethylene copolymers suitable for the present invention include tapered or block copolymers (including terpolymers, tetrapolymers, etc.) as well as those that have controlled compositional homogeneity and/or heterogeneity within and among copolymer chains which are well known in the art.
• Such copolymers are described in " Polymers as Lubricating Oil Viscosity Modifiers", G. VerStrate, M. J. Struglinski, Chapter 15; in “Polymers as Rheology Modifiers", D. N. Schulz and J. E. Glass, editors, American Chemical Society, Washington, D.C., 1991 .
• the semi-crystalline viscosity modifier is an oil-soluble polymer comprised of ethylene and a C 3 to C 18 alpha-olefin, the polymer being characterized by the following combination of parameters: (a) an average ethylene content within the range between 60 to 80 mole percent, wherein said polymer contains no more than 1.3% by weight of a polymer fraction which is insoluble in normal decane at 45°C; (b) a degree of crystallinity less than 25%; (c) a weight average molecular weight/number average molecular weight ratio less than 4.0; and (d) a viscosity average molecular weight within the range between 10,000 and 200,000 Daltons.
• Suitable viscosity modifiers are disclosed in US Patent No. 3,551,336 .
• the semi-crystalline viscosity modifier is a segmented copolymer of ethylene and at least one other alpha-olefin monomer; each copolymer is intramolecularly heterogeneous and intermolecularly homogeneous and at least one segment of the copolymer, constituting at least 10% of the copolymer's chain, is a crystallizable segment.
• Suitable viscosity modifiers are disclosed in US Patent No. 4,804,794 .
• the semi-crystalline viscosity modifier is included in combination with an amorphous viscosity modifier.
• an oil-soluble polymer composition comprising a first copolymer of ethylene and a C 3 to C 18 alpha-olefin having an ethylene content of 50-95 mole percent and a second copolymer of ethylene and a C 3 to C 18 higher alpha-olefin having an ethylene content of 5-80 mole percent, the ethylene content of the first copolymer being at least 5 mole percent more than the ethylene content of the second polymer.
• Suitable amorphous viscosity modifiers are disclosed in US Patent No. 3,697,429 .
• the semi-crystalline viscosity modifier has a number average molecular weight ranging from 20,000 to 500,000 Daltons, for example, from 25,000 to 400,000 Daltons or from 30,000 to 300,000 Daltons as determined by gel permeation chromatography.
• the semi-crystalline viscosity modifier can be present in the lubricant composition in an amount ranging from 0.05 to 5 wt. % of the polymer
• the lubricant composition comprises one or more LOFIs having a side-chain distribution which satisfies the following requirements:
• the amount of C 14 must be less than 20 mole %, for example, less than 10 mole % of the total side chain distribution.
• the side chains comprise even carbon number segments ranging from C 8 to C 18 , i.e., C 8 , C 10 , C 12 , C 14 , C 16 , C 18 .
• the LOFI comprises a dialkyl fumarate-vinyl acetate copolymer.
• the dialkyl fumarate-vinyl acetate copolymer can be formed from a mixture of alcohols having carbon numbers ranging from 8 to 18, with an average carbon number from 12.4 to 14.4, for example, from 12.8 to 14.0, or from 13.0 to 13.8.
• the copolymer is a sidechain copolymer having methylene segments as the side chains.
• LOFIs can contain pendent ester groups derived from a mixture of alcohols whereby the alcohol residue can be characterized as repeating methylene units, and which are oil soluble, or dispersible, polymeric compositions that generally have weight average molecular weights ranging from 50,000 to 350,000 Daltons as determined by gel permeation chromatography.
• the dialkyl fumarate-vinyl acetate copolymer has a specific viscosity ranging from 0.3 to 1.5, for example, from 0.3 to 1.0 or from 0.45 to 0.7.
• the dialkyl fumarate-vinyl acetate copolymer has a weight average molecular weight ranging from 50,000 to 350,000 Daltons, for example, from 50,000 to 200,000 Daltons or from 75,000 to 120,000 Daltons.
• additives The LOFI and one or more other components, excluding the base stock, in a lubricant composition are referred to as "additives".
• the LOFI has a weight average molecular weight, as determined by gel permeation chromatography, ranging from 50,000 to 350,000 Daltons, for example from 80,000 to 200,000 Daltons.
• the LOFI has a specific viscosity ranging from 0.3 to 1.0, for example, from 0.4 to 0.8.
• the LOFI can be present in the lubricant composition in an amount ranging from 0.005 to 1.0 weight percent, for example from 0.05 to 0.5 weight percent.
• the lubricant composition of the present invention can further comprise one or more of the optional components: corrosion inhibitors, oxidation inhibitors, friction modifiers, dispersants, anti-foaming agents, anti-wear agents, detergents, rust inhibitors, etc.
• the lubricant composition of the present invention comprises a corrosion inhibitor.
• 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 phosphosulfurized hydrocarbons and the products obtained by reaction of a phosphosulfurized 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.
• Phosphosulfurized hydrocarbons are prepared by reacting a suitable hydrocarbon such as a terpene, a heavy petroleum fraction of a C 2 to C 6 olefin polymer such as polyisobutylene, with from 5 to 30 wt. percent of a sulfide of phosphorus for 1/2 to 15 hours, at a temperature in the range of 150°F to 600°F (66°C to 316°C). Neutralization of the phosphosulfurized hydrocarbon may be effected in the manner taught in U.S. Pat. No. 1,969,324 .
• the lubricant composition of the invention can comprise an oxidation inhibitor.
• 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 alkaline earth metal salts of alkylphenolthioesters having preferably C 5 to C 12 alkyl side chains, e.g., calcium nonylphenol sulfide, barium t-octylphenyl sulfide, dioctylphenylamine, phenylalphanaphthylamine, phosphosulfurized or sulfurized hydrocarbons, etc.
• the lubricant of the present invention comprises a friction modifier.
• Friction modifiers serve to impart the proper friction characteristics to lubricating oil compositions such as automatic transmission fluids.
• suitable friction modifiers are found in U.S. Pat. No. 3,933,659 that discloses fatty acid esters and amides; U.S. Pat. No. 4,176,074 that describes molybdenum complexes of polyisobutenyl succinic anhydride-amino alkanols; U.S. Pat. No. 4,105,571 that discloses glycerol esters of dimerized fatty acids; U.S. Pat. No. 3,779,928 that discloses alkane phosphonic acid salts; U.S. Pat.
• Preferred friction modifiers include succinate esters, or metal salts thereof, of hydrocarbyl substituted succinic acids or anhydrides and thiobis alkanols such as described in U.S. Pat. No. 4,344,853 as well as various molybdenum compounds.
• the lubricant composition of the present invention comprises a dispersant.
• Dispersants maintain compounds resulting from oxidation during use that are insoluble or substantially insoluble in the oil, in suspension in the fluid thus preventing sludge flocculation and precipitation or deposition on metal parts.
• Suitable dispersants include high molecular weight alkyl succinates, the reaction product of oil-soluble polyisobutylene succinic anhydride with ethylene amines such as tetraethylene pentamine and borated salts thereof.
• the lubricant composition of the present invention comprises a component to provide foam control.
• Foam control can be provided by an antifoamant of the polysiloxane type, e.g., silicone oil and polydimethyl siloxane.
• the lubricant composition of the present invention comprises an anti-wear agent.
• Anti-wear agents as their name implies, reduce wear of metal parts.
• Representatives of conventional anti-wear agents are zinc dialkyldithiophosphate and zinc diaryldithiophosphate.
• the lubricant composition of the present invention comprises a detergent and metal rust inhibitor.
• Detergents and metal rust inhibitors include the metal salts of sulphonic acids, alkyl phenols, sulfurized alkyl phenols, alkyl salicylates, naphthenates and other oil soluble mono- and dicarboxylic acids.
• Highly basic (viz., overbased) metal salts such as highly basic alkaline earth metal sulfonates (especially Ca and Mg salts) are frequently used as detergents. Representative examples of such materials, and their methods of preparation, are found in U.S. Pat. No. 6,127,321 .
• Lubricant composition of the present invention can be made using methods and techniques which are well known in the art.
• Lubricant compositions according to the present invention are typically made by blending individual components into the base stock.
• the components can be added directly to the base stock by dispersing, or dissolving the additives at the desired level of concentration at room temperature or elevated temperatures.
• the present invention is illustrated by the following non-limiting examples.
• the lubricant compositions comprised a Group III base stock (Yubase base stock); a semi-crystalline viscosity modifier (Paratone 8451 from Chevron Oronite Company); and a LOFI which was prepared as described below.
• Each lubricant composition contained a different LOFI.
• the lubricant composition of Example 1 contains LOFI 1
• the lubricant composition of Example 2 contains LOFI 2 and so on.
• LOFIs Five LOFIs (LOFIs 1-5) were prepared by first making five dialkyl fumarate monomers (Dialkyl Fumarate Monomers 1-5) using a blend of alcohols having a distribution of carbon atoms as shown in Table I. Alcohol 1 in Table I is used to prepare Dialkyl Fumarate Monomer 1, Alcohol 2 in Table I is used to prepare Dialkyl Fumarate Monomer 2 and so on. 232 g of fumaric acid, 824 g of the specified alcohol blend, and 0.2 g Fascat 4100® were added to the round bottom flask equipped with a Dean-Stark apparatus. The slurry was stirred under a stream of nitrogen and slowly heated to 220°C.
• the esterification reaction was monitored by measuring the amount of water collected in the Dean-Stark trap. When the evolution of water ceased (typically 4 to 6 hours), the dialkyl fumarate monomer was decanted from the reactor and analyzed for neutralization number (2.0 mg KOH/g) and saponification number (223 mg KOH/g). Dialkyl Fumarate Monomers 1-5 were formed in this way.
• Dialkyl Fumarate Monomer 1 was used to prepare Dialkyl Fumarate Vinyl Acetate Copolymer 1
• Dialkyl Fumarate Monomer 2 was used to prepare Dialkyl Fumarate Vinyl Acetate Copolymer 2 and so on.
• 150 g of a Dialkyl Fumarate Monomer (Dialkyl Fumarate Monomers 1-5) were added to a Parr® brand, 300 cm 3 stainless steel reactor. The reactor was sealed, heated to 50°C, and flushed with nitrogen for 10 minutes.
• Dialkyl Fumarate Vinyl Acetate Copolymers 1-5 were blended as is well known in the art with a Group III base stock (Yubase base stock) and a semi-crystalline viscosity modifier (Paratone 8451 from Chevron Oronite Company) to form the SAE 5W-30 lubricant compositions of Examples 1-5.
• a Group III base stock Yubase base stock
• a semi-crystalline viscosity modifier Paratone 8451 from Chevron Oronite Company
• the distribution contains side chains ranging from C 8 to C 18 with an average carbon number from 12.4 to 14.4 ⁇ ⁇ ⁇ ⁇ ⁇ (2) the side chain distribution is bi-modal with the lower portion of the bi-modal distribution made up primarily of C 12 and the upper portion of the distribution made up primarily of C 16 , C 18 or combinations thereof ⁇ ⁇ ⁇ X X (3) the sum of the upper portion of the distribution must be less than the lower portion of the distribution.
• the amount of C 14 must be less than 20% or less than 10% when the essential components of the bi-modal distribution are made up of mixtures of (a) C 12 and C 16 or (b) C 12 , C 16 and C 18 and must be less than the sum of C 16 and C 18 ; ⁇ ⁇ ⁇ X X (4) the amount of C 12 must be at least 40 mole % or at least 50 mole % of the total side chain distribution. ⁇ ⁇ ⁇ ⁇ X
• the LOFIs in the lubricant compositions of Examples 1-3 satisfy all of the requirements and are encompassed by the present invention.
• the LOFIs in the lubricant compositions of Examples 4 and 5 do not satisfy all of the requirements and fall outside of the present invention.
• MRV Pumpability Test Ex. 1 Ex. 2 Ex. 3 Ex. 4 Ex. 5 At a Treat Rate of 0.50% Viscosity [mPa ⁇ s] 27,200 -- 24,400 161,100 54,200 Yield Stress [Pa] ⁇ 35 -- ⁇ 35 ⁇ 350 ⁇ 140 At a Treat Rate of 0.20% Viscosity [mPa ⁇ s] 23,800 21,400 22,400 -- -- Yield Stress [Pa] ⁇ 35 ⁇ 35 ⁇ 35 -- -- -- means yield stress and viscosity were not tested.
• a lubricant composition In order to pass the MRV Pumpability Test, a lubricant composition must exhibit a viscosity equal to or less than 60,000 mPa ⁇ s and a yield stress of less than 35 Pa. At a treat rate of 0.50%, only Examples land 3 passed the MRV Pumpability Test. At a treat rate of 0.20%, only Examples 1-3 pass the MRV Pumpability Test. As stated above, Examples 1-3 are encompassed by the present invention.

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)

Publications (3)

Family

ID=40512878

Family Applications (1)

Country Status (6)

Families Citing this family (4)

Citations (1)

Family Cites Families (30)

• 2007
  • 2007-12-03 US US11/949,083 patent/US20090143263A1/en not_active Abandoned
• 2008
  • 2008-12-02 CA CA2645580A patent/CA2645580C/en active Active
  • 2008-12-02 EP EP08105917.2A patent/EP2071013B1/en active Active
  • 2008-12-02 CN CN2008101816647A patent/CN101451086B/zh active Active
  • 2008-12-02 SG SG200808923-7A patent/SG153029A1/en unknown
  • 2008-12-03 JP JP2008308406A patent/JP5517440B2/ja active Active

Patent Citations (1)

Also Published As

Similar Documents

Legal Events