US20150232781A1 - Lubricating Composition Including Esterified Copolymer And Method - Google Patents

Lubricating Composition Including Esterified Copolymer And Method Download PDF

Info

Publication number
US20150232781A1
US20150232781A1 US14/422,390 US201314422390A US2015232781A1 US 20150232781 A1 US20150232781 A1 US 20150232781A1 US 201314422390 A US201314422390 A US 201314422390A US 2015232781 A1 US2015232781 A1 US 2015232781A1
Authority
US
United States
Prior art keywords
monomer
carboxylic acid
copolymer
units
lubricating composition
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
US14/422,390
Other languages
English (en)
Inventor
William R.S. Barton
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.)
Lubrizol Corp
Original Assignee
Lubrizol Corp
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 Lubrizol Corp filed Critical Lubrizol Corp
Priority to US14/422,390 priority Critical patent/US20150232781A1/en
Assigned to THE LUBRIZOL CORPORATION reassignment THE LUBRIZOL CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BARTON, WILLIAM R.S.
Publication of US20150232781A1 publication Critical patent/US20150232781A1/en
Abandoned legal-status Critical Current

Links

Images

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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/22—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/28—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
    • 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
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—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
    • C10M145/12—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 monocarboxylic
    • 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
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—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
    • C10M145/16—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 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
    • 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
    • C10M2203/108—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
    • 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
    • C10M2205/0225—Ethene 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
    • C10M2205/028—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
    • C10M2205/02—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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
    • 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
    • C10M2209/082—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 monocarboxylic
    • 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
    • C10N2020/019—Shear stability
    • 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
    • C10N2030/02—Pour-point; 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
    • C10N2030/54—Fuel economy
    • 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
    • C10N2030/68—Shear stability
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • C10N2040/20—Metal working
    • 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
    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/06—Chemical after-treatment of the constituents of the lubricating composition by epoxydes or oxyalkylation reactions
    • 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
    • C10N2060/09—Treatment with nitrogen containing compounds

Definitions

  • the exemplary embodiment relates to a lubricating composition comprising an esterified copolymer.
  • the lubricating composition finds particular application in driveline devices, such as transmissions, but may also be employed in other devices, such as crankcase lubricants for engine oils. Also disclosed are a method and a use of the lubricating composition.
  • Viscosity modifiers also known as viscosity index (VI) improvers
  • VI viscosity index improvers
  • the viscosity modifier is combined, in the lubricating oil composition, with a base oil, together with other performance additives, such as dispersants, detergents, friction modifiers, corrosion inhibitors, pour point depressants, and so forth, depending on the particular application.
  • Typical viscosity modifiers include polymers of alkyl methacrylates, alkyl acrylates, olefins (such as copolymers of ethylene and propylene), copolymers of styrene and conjugated dienes, and copolymers of maleic anhydride with alpha-olefins or styrene, and their esterified derivatives.
  • Viscosity modifiers comprising ester groups tend to incorporate ester functional groups in pendent/grafted/branched groups.
  • the ester functional groups may be derived from linear or branched alkyl alcohols with 1 to 40 carbon atoms. Examples of such polymers are disclosed in U.S. Pat. Nos. 5,435,928; 6,174,843; 6,419,714; 6,544,935; and 7,254,249; and International Application Nos. WO 07/133999 and WO 2010/014655.
  • Compositions have been formulated to achieve minimum high temperature/high shear rate (HTHS) viscosity to protect against excessive wear in various areas of an automobile, such as driveline devices and in the engine.
  • HTHS viscosity lubricating compositions although good for wear protection, tend to suffer from poor fuel economy.
  • fluids with relatively low HTHS viscosities typically also exhibit low kinematic viscosity (KV), resulting in formation of a thinner lubricating film, which can improve fuel economy but negatively impact wear protection.
  • KV kinematic viscosity
  • FIG. 4 is a graph showing the viscosity of the fluids of Example 2 under high shear rates at 150° C.
  • a method for determining viscosity index (VI) of a lubricating composition is according to the procedure outlined in ASTM D2270, “Standard Practice for Calculating Viscosity Index From Kinematic Viscosity at 40 and 100° C.,” ASTM International, West Conshohocken, Pa., DOI: 10.1520/D2270-10E01.
  • the viscosity at low temperatures can be measured using the Brookfield Viscosity method as described in ASTM method D2983-09, “Standard Test Method for Low-Temperature Viscosity of Lubricants Measured by Brookfield Viscometer.” According to SAE J306, “Automotive Gear Lubricant Viscosity Classification,” for SAE 75W automotive gear oils, the maximum viscosity measured at ⁇ 26° C. is also 150,000 cP.
  • an esterified copolymer according to embodiments of the invention can provide a lubricant with at least one (or at least two, or all) of acceptable or improved HTHS, KV, shear stability, acceptable or improved viscosity index control, and acceptable or improved low temperature viscosity.
  • An exemplary lubricating composition can include from 0.1 to 50 wt. %, or 1.0 to 20 wt. %, or 1.5 to 10 wt. % of the exemplary viscosity modifier, such as less than 5 wt. % of the viscosity modifier.
  • the exemplary viscosity modifier is an esterified copolymer.
  • the exemplary esterified copolymer (A) disclosed herein includes a polymeric backbone comprising units (A1) derived from a vinyl monomer and units (A2) derived from a carboxylic acid monomer, which can be an ethylenically unsaturated carboxylic acid or derivative thereof.
  • the vinyl monomer can be selected from polymerizable aromatic and aliphatic vinyl monomers.
  • Exemplary aliphatic vinyl monomers include alpha-olefins.
  • the exemplary copolymer can include a polymeric backbone derived from 1-dodecene and maleic anhydride, as the carboxylic acid monomer.
  • the polymeric backbone can be an alternating structure whereby each carboxylic acid unit is spaced from the next carboxylic acid unit by at least one unit derived from a vinyl monomer, such as an alpha-olefin.
  • the exemplary esterified copolymer can have at least 20 or at least 100 units derived from these monomers in its backbone.
  • the backbone chain of monomer units derived from the selected monomers is of no more than 10,000 such monomer units, or no more than 1000 such monomer units.
  • the ester groups and nitrogen containing groups are sufficient to provide 0.01 wt. % to 1.5 wt. % (or 0.02 wt. % to 0.75 wt. %, or 0.04 wt. % to 0.25 wt. %) nitrogen to the esterified copolymer.
  • An exemplary vinyl aromatic monomer where present, is a polymerizable aromatic monomer, specifically, an aromatic compound substituted with a vinyl group (—CH ⁇ CH 2 ).
  • the exemplary ethylenically unsaturated carboxylic acid or derivative thereof used in forming the carboxylic acid units (A2) of the exemplary esterified copolymer (A) may be a mono- or dicarboxylic acid or an anhydride or other derivative thereof that may be wholly esterified, partially esterified, or a mixture thereof.
  • other functional groups may include acids, salts or mixtures thereof.
  • Suitable salts include alkali metals, alkaline earth metals, and mixtures thereof.
  • the salts may include lithium, sodium, potassium, magnesium, calcium or mixtures thereof.
  • the functional groups defined by X in Formula II above may comprise at least one of —CO 2 —, —C(O)N ⁇ or —(CH 2 ) v —, wherein v is an integer in the range of 1 to 20, or 1 to 10, or 1 to 2.
  • the pendent groups may be esterified, amidated or imidated functional groups.
  • the exemplary esterified copolymer (A) includes a nitrogen-containing group, such as an amino-, amido- and/or imido-group.
  • the nitrogen-containing group may be derived from a nitrogen-containing compound capable of being incorporated during copolymerization (or through reaction with the carboxylic acid units to form a salt), such as an amine, to form a salt, amide, imide, or mixture thereof.
  • Suitable amines include 3-amino-N-(4-anilinophenyl)-N-isopropyl butanamide, and N-(4-anilinophenyl)-3- ⁇ (3-aminopropyl)-(cocoalkyl)amino ⁇ butanamide.
  • Other aromatic amines which can be used include various aromatic amine dye intermediates containing multiple aromatic rings linked by, for example, amide structures. Examples include materials of the general structure:
  • ⁇ -alanine alkyl esters may be represented by the general structure:
  • Copolymerization of 1-dodecene and maleic anhydride in toluene under conventional free radical polymerization techniques leads to a low molecular weight copolymer.
  • Esterification (or transesterification, when the copolymer backbone already contains ester groups and those of a different type are desired) of the exemplary copolymer backbone can be accomplished by heating any of the copolymers described above and one or more desired alcohols and/or alkoxylates under conditions typical for effecting esterification.
  • Such conditions include, for example, a temperature of at least 80° C., such as up to 150° C. or higher, provided that the temperature is maintained below the lowest decomposition temperature of any component of the reaction mixture or products thereof. Water or lower alcohol is normally removed as the esterification proceeds.
  • the lubricating composition may include the oil of lubricating viscosity as a minor or major component thereof, such as at least 5 wt. %, or at least 20 wt. %, or at least 30 wt. %, or at least 40 wt. %, or at least 60 wt. % of the lubricating composition.
  • the base oil (C) in the lubricating composition can be for example, from 10 to 95 wt. %, or 20-80 wt. %.
  • Other performance additives other than the viscosity modifier can be for example, from 0.2 to 40 wt. %, or 0.5-5 wt. % of the lubricating composition.
  • the total combined amount of the performance additives present ranges from 0 wt. % to 30 wt. %, or from 1 wt. % to 25 wt. %, or from 2 wt. % to 20 wt. %, or from 3 wt. % to 10 wt. % of the lubricating composition. Although one or more of the performance additives may be present, it is common for the performance additives to be present in different amounts relative to each other.
  • Suitable foam inhibitors include silicones, copolymers of ethyl acrylate and 2-ethylhexylacrylate which optionally further include vinyl acetate; and demulsifiers including polyethylene glycols, polyethylene oxides, polypropylene oxides and (ethylene oxide-propylene oxide) polymers.
  • the procedure for testing the samples is as follows: temperature and shear rate parameters are assigned in the computer. The application allows for multiple temperatures and shear rates to be assigned, but as stated individual temperatures and shear rates are used. Once the temperature and shear rate profile has been loaded, the new sample is loaded. Numerous flushing steps of the current test fluid are required before the sample (0.5 mL) is loaded into the test chamber. Once loaded and set to run, the motor and flywheel are set to spin to provide the appropriate shear rate. A clutch engages the rotor and three pulses, approximately five second apart, are applied to the sample. The viscosity is determined by calculating the average of the resistance on the rotor.
  • substituted hydrocarbon substituents that is, substituents containing non-hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon nature of the substituent (e.g., halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulfoxy);

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)
US14/422,390 2012-08-20 2013-08-14 Lubricating Composition Including Esterified Copolymer And Method Abandoned US20150232781A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US14/422,390 US20150232781A1 (en) 2012-08-20 2013-08-14 Lubricating Composition Including Esterified Copolymer And Method

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261684876P 2012-08-20 2012-08-20
PCT/US2013/054865 WO2014031402A1 (en) 2012-08-20 2013-08-14 Lubricating composition including esterified copolymer and method
US14/422,390 US20150232781A1 (en) 2012-08-20 2013-08-14 Lubricating Composition Including Esterified Copolymer And Method

Publications (1)

Publication Number Publication Date
US20150232781A1 true US20150232781A1 (en) 2015-08-20

Family

ID=49004067

Family Applications (1)

Application Number Title Priority Date Filing Date
US14/422,390 Abandoned US20150232781A1 (en) 2012-08-20 2013-08-14 Lubricating Composition Including Esterified Copolymer And Method

Country Status (8)

Country Link
US (1) US20150232781A1 (ko)
EP (1) EP2885387B1 (ko)
JP (1) JP2015526564A (ko)
KR (1) KR20150043496A (ko)
CN (1) CN104781380A (ko)
AU (1) AU2013306169B2 (ko)
CA (1) CA2882135C (ko)
WO (1) WO2014031402A1 (ko)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11999920B2 (en) 2020-09-14 2024-06-04 Ecolab Usa Inc. Cold flow additives for plastic-derived synthetic feedstock
US12031097B2 (en) 2021-10-14 2024-07-09 Ecolab Usa Inc. Antifouling agents for plastic-derived synthetic feedstocks

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3074809B1 (fr) * 2017-12-11 2019-12-13 Total Marketing Services Composition de graisse presentant une adhesivite amelioree
CN109535297B (zh) * 2018-11-06 2021-03-30 江南大学 一种侧链含酰胺键的共聚物及其制备方法和应用
EP3705557A1 (en) * 2019-03-07 2020-09-09 Sasol Performance Chemicals GmbH Use of polymers as additives for lubricant oil compositions

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010014655A1 (en) * 2008-07-31 2010-02-04 The Lubrizol Corporation Novel copolymers and lubricating compositions thereof

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0762373A (ja) * 1993-08-20 1995-03-07 Sanyo Chem Ind Ltd 潤滑油添加剤および潤滑油組成物
MXPA02000223A (es) * 1999-07-09 2002-06-21 Lubrizol Corp Interpolimeros con contenido en carboxi esterificados con contenido en nitrogeno que tienen una mejor estabilidad oxidante y lubricantes que los contienen.
WO2005103093A2 (en) * 2004-04-19 2005-11-03 The Lubrizol Corporation Dispersant viscosity modifiers based on maleic anhydride-styrene copolymers
US8293689B2 (en) * 2006-05-08 2012-10-23 The Lubrizol Corporation Lubricating composition containing a polymer and antiwear agents
EP2014750B1 (en) * 2007-06-13 2012-08-08 Italmatch Chemicals S.P.A. High viscosity lubricant copolymers
JP5483662B2 (ja) * 2008-01-15 2014-05-07 Ｊｘ日鉱日石エネルギー株式会社 潤滑油組成物
JP5689592B2 (ja) * 2009-09-01 2015-03-25 Ｊｘ日鉱日石エネルギー株式会社 潤滑油組成物
CN106010746A (zh) * 2009-11-24 2016-10-12 路博润公司 含有粘度改进剂组合的润滑组合物
US9181510B2 (en) * 2010-05-20 2015-11-10 The Lubrizol Corporation Lubricating composition containing a dispersant
JP2015507073A (ja) * 2012-02-17 2015-03-05 ザ ルブリゾル コーポレイションＴｈｅ Ｌｕｂｒｉｚｏｌ Ｃｏｒｐｏｒａｔｉｏｎ 動力伝達用途に適切な、エステル化コポリマーおよび少量の分散剤を含む潤滑組成物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010014655A1 (en) * 2008-07-31 2010-02-04 The Lubrizol Corporation Novel copolymers and lubricating compositions thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11999920B2 (en) 2020-09-14 2024-06-04 Ecolab Usa Inc. Cold flow additives for plastic-derived synthetic feedstock
US12031097B2 (en) 2021-10-14 2024-07-09 Ecolab Usa Inc. Antifouling agents for plastic-derived synthetic feedstocks

Also Published As

Publication number Publication date
CA2882135A1 (en) 2014-02-27
EP2885387B1 (en) 2018-10-03
CA2882135C (en) 2020-10-13
AU2013306169A1 (en) 2015-03-05
CN104781380A (zh) 2015-07-15
JP2015526564A (ja) 2015-09-10
WO2014031402A1 (en) 2014-02-27
AU2013306169B2 (en) 2017-03-30
EP2885387A1 (en) 2015-06-24
KR20150043496A (ko) 2015-04-22

Similar Documents

Publication Publication Date Title
EP2310425B1 (en) Novel copolymers and lubricating compositions thereof
US9758743B2 (en) Mixtures of olefin-ester copolymer with polyolefin as viscosity modifier
US8354362B2 (en) Polymer and lubricating compositions thereof
US20160040089A1 (en) Lubricating Composition Including Esterified Copolymer And Low Dispersant Levels Suitable For Driveline Applications
CA2882135C (en) Lubricating composition including esterified copolymer and method
US20150240183A1 (en) Lubricant comprising a mixture of an olefin-ester copolymer with an ethylene alpha-olefin copolymer
US20150203784A1 (en) Lubricating Composition Including Esterified Copolymer And Diene Rubber Polymer

Legal Events

Date Code Title Description
AS Assignment

Owner name: THE LUBRIZOL CORPORATION, OHIO

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:BARTON, WILLIAM R.S.;REEL/FRAME:035111/0311

Effective date: 20131010

STCB Information on status: application discontinuation

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