EP2376611B1 - Friction modifiers and/or wear inhibitors derived from hydrocarbyl amines and glycerol carbonate - Google Patents

Friction modifiers and/or wear inhibitors derived from hydrocarbyl amines and glycerol carbonate Download PDF

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Publication number
EP2376611B1
EP2376611B1 EP09837831.8A EP09837831A EP2376611B1 EP 2376611 B1 EP2376611 B1 EP 2376611B1 EP 09837831 A EP09837831 A EP 09837831A EP 2376611 B1 EP2376611 B1 EP 2376611B1
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Prior art keywords
lubricating oil
oil composition
hydrocarbyl
amine
carbon atoms
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EP09837831.8A
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German (de)
English (en)
French (fr)
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EP2376611A2 (en
EP2376611A4 (en
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William R. Ruhe Jr.
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Chevron Oronite Co LLC
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Chevron Oronite Co LLC
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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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
    • C10M133/18—Amides; Imides of carbonic or haloformic 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/10—Amides of carbonic or haloformic 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/09—Complexes with metals
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • 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
    • C10N2020/069—Linear chain compounds
    • 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
    • C10N2020/071—Branched chain compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—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
    • C10N2040/08—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
    • C10N2040/25—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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • the present invention relates to carbamates having improved wear inhibition and friction modifier properties as part of a lubricating oil composition.
  • Antiwear additives and friction modifying additives are frequently blended with lubricants in order to prevent wear, reduce fuel consumption, and increase the operating life of machinery.
  • Glycerol esters such as glycerol monooleate, are well known in the art as friction modifiers and as wear inhibitors. The problem associated with these compounds is that the ester functionality is easily hydrolyzed which results in the production of free oleic acid, a corrosive agent.
  • US5962379 relates to carbonates which have been prepared by reacting alkylamines with dialkylcarbonates and/or alkylene carbonates, and their use as friction reducing additives in fuels and lubes.
  • This invention is directed to a lubricating oil composition
  • a lubricating oil composition comprising a major amount of base oil of lubricating viscosity and a minor amount of an additive comprising the reaction product obtained by reacting glycerol carbonate and a hydrocarbyl amine having the formula: R 1 R 2 NH in which R 1 is hydrogen, or a hydrocarbyl group containing 1 to 40 carbon atoms, and R 2 is a hydrocarbyl group containing 1 to 40 carbon atoms.
  • the hydrocarbyl amine is oleylamine
  • the reaction product is glycerol carbamate.
  • Glycerol carbmates have improved wear inhibition and friction modifier properties as part of the lubricating oil composition.
  • a carbamate which is a reaction product of a cyclic carbonate, such as ethylene carbonate, and a hydrocarbyl amine such as 2-ethylhexamine or oleylamine.
  • This invention relates to a carbamate additive, comprising the reaction product of glycerol carbonate and a hydrocarbyl amine, which may be incorporated into a lubricating oil composition.
  • a carbamate additive comprising the reaction product of glycerol carbonate and a hydrocarbyl amine, which may be incorporated into a lubricating oil composition.
  • Such lubricating oil compositions having this additive are particularly beneficial for reducing wear in tractor hydraulic fluids, and may be useful in other lubricating oil applications such as engine oils and gear oils.
  • Such lubricating oil compositions having this additive may also provide for excellent friction reduction properties in the aforesaid applications.
  • hydrocarbyl denotes a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character.
  • groups may include the following: (1) Hydrocarbon groups; that is, aliphatic, (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl or cycloalkenyl), aromatic, aliphatic- and alicyclic-substituted aromatic, aromatic-substituted aliphatic and alicyclic groups, and the like.
  • Such groups are known to those skilled in the art, and non-limiting examples include methyl, ethyl, octyl, decyl, octadecyl, cyclohexyl, phenyl, individually or in combinations thereof, etc.; (2) Substituted hydrocarbon groups; that is, groups containing non-hydrocarbon substituents which do not alter the predominantly hydrocarbon character of the group.
  • substituents include halo, hydroxyl, nitro, cyano, alkoxy, acyl, etc., and optionally, (3) Hetero groups; that is, groups which, while predominantly hydrocarbon in character within the context of this invention, contain atoms other than carbon in a chain or ring otherwise composed of carbon atoms.
  • Suitable hetero atoms will be apparent to those skilled in the art and non-limiting examples include nitrogen, oxygen and sulfur.
  • Cyclic carbonates include those having the formula (I) below.
  • An example of a cyclic carbonate wherein R 3 and R 4 are hydrogen is ethylene carbonate.
  • Propylene carbonate is an example of a cyclic carbonate wherein R 3 is hydrogen and R 4 is a methyl group.
  • Glycerol carbonate is an example of a cyclic carbonate wherein R 3 is hydrogen and R 4 is a CH 2 -OH group.
  • Carbamates are prepared by reaction of a hydrocarbyl amine and a cyclic carbonate.
  • the hydrocarbyl amine is shown by the following formula (II): Formula (II) R 1 R 2 NH in which R 1 is hydrogen, or a hydrocarbyl group containing 1 to 40 carbon atoms, and more preferably, 8 to 28 carbon atoms and R 2 is a hydrocarbyl group containing 1 to 40 carbon atoms, and more preferably 8 to 28 carbon atoms.
  • the hydrocarbyl group in R 1 and R 2 may be a linear and/or branched, alkyl and/or alkenyl group.
  • the hydrocarbyl amine is oleylamine
  • the carbamate is glycerol carbamate.
  • Glycerol carbamates which are obtained by reaction of glycerol carbonate with a primary, and optionally a secondary, hydrocarbyl amine, such as saturated or unsaturated mono-amines, or mixtures of hydrocarbyl amines derived from fatty acids, such as coco, oleyl, or tallow, preferably, oleylamine.
  • Non limiting examples of primary and secondary hydrocarbyl amines include octylamine, decylamine, dodecyl-amine, tetradecylamine, hexadecylamine, octadecylamine, benzylamine, phenylamine, oleylamine (for example Armeen ® OLD from Akzo Nobel), stearylamine (for example Armeen 18 D from Akzo Nobel), cocoamine, 2-ethylhexylamine, isotridecylamine, 2-butyloctylamine, 2-hexyldecylamine, 2-octyldodeylamine, cyclohexylamine, , dibenzylamine, diphenylamine, dicocoamine (for example Armeen 2C from Akzo Nobel), di-2-ethylhexylamine, and N-methylcyclohexylamine,.
  • carbamates obtained by reaction of ethylene carbonate with a primary hydrocarbyl amine preferably 2-ethylhexylamine.
  • carbamates obtained by reaction of ethylene carbonate with a primary hydrocarbyl amine preferably oleylamine.
  • Glycerol carbonate can be produced by methods known from the prior art as described, for example, in U.S. Pat. No. 6,025,504 .
  • Ethylene carbonate can be produced by methods known from the prior art as described, for example, in U.S. Pat. No. 4,314,945 and U.S. Pat. No. 4,233,221 .
  • glycerol carbamates are prepared by reaction of oleylamine 1 and glycerol carbonate 2 , in reaction scheme (I) below.
  • the reaction occurs at a molar ratio of oleylamine to glycerol carbonate of 0.5:1 to 2:1, preferably 0.75:1 to 1.5:1 and more particularly 1:1, and at a temperature range of between 60 °C and 180 °C, and more preferably between 80 °C and 120 °C.
  • a mixture of products is obtained.
  • the major products are glycerol carbamates, some general structures of which are shown as 3 and 4 .
  • Minor products may include glycerol, hydroxyethylamines, and dioleyl urea. Hydrocarbon solvents or other inert solvents may be used in the reaction, such as benzene, toluene, and xylenes.
  • carbamate compounds of this invention may be incorporated into a lubricating oil composition comprising a base oil of lubricating viscosity and other additive components, by the direct blending of the carbamate compounds with the lubricating oil composition.
  • the amount of carbamate additive compounds in the lubricating oil composition is present in a "minor amount,” which refers to a concentration of the additive within the lubricating oil composition of less than about 40 wt %.
  • a “minor amount” of additive refers to a concentration of the additive within the lubricating oil composition of less than about 30 wt%, of less than about 20 wt %, of less than about 10 wt %, of less than about 1 wt %, or of less than about 0.5 wt %.
  • the base oil of lubricating viscosity employed in the present invention may be mineral oils or synthetic oils.
  • a base oil having a viscosity of at least 10 cSt (mm 2 /s) at 40° C and a pour point below 20° C, preferably at or below 0° C is desirable.
  • the base oils may be derived from synthetic or natural sources.
  • Mineral oils for use as the base oil in this invention include, for example, paraffinic, naphthenic and other oils that are ordinarily used in lubricating oil compositions.
  • Synthetic oils include, for example, both hydrocarbon synthetic oils and synthetic esters and mixtures thereof having the desired viscosity.
  • Hydrocarbon synthetic oils may include, for example, oils prepared from the polymerization of ethylene or higher alpha olefins (polyalphaolefin or PAO), or from hydrocarbon synthesis procedures using carbon monoxide and hydrogen gases such as in a Fisher-Tropsch process.
  • Useful synthetic hydrocarbon oils include liquid polymers of alpha olefins having the proper viscosity. Especially useful are the hydrogenated liquid oligomers of C 6 to C 12 alpha olefins such as 1-decene trimer.
  • alkyl benzenes of proper viscosity such as didodecyl benzene, can be used.
  • Useful synthetic esters include the esters of monocarboxylic acids and polycarboxylic acids, as well as mono-hydroxy alkanols and polyols. Typical examples are didodecyl adipate, pentaerythritol tetracaproate, di-2-ethylhexyl adipate, dilaurylsebacate, and the like. Complex esters prepared from mixtures of mono and dicarboxylic acids and mono and dihydroxy alkanols can also be used. Blends of mineral oils with synthetic oils are also useful. For example, blends of 10 wt % to 25 wt % hydrogenated 1-decene trimer with 75 wt % to 90 wt % 150 SUS (100F.) mineral oil make excellent lubricating oil bases.
  • additive components are examples of some other additive components that can be favorably employed in the present invention. These examples of additives are provided to illustrate the present invention, but they are not intended to limit it:
  • the base oil of the present invention is present in a "major amount.”
  • a “major amount” of a base oil of lubricating viscosity refers to a concentration of the oil within the lubricating oil composition of at least about 40 wt %.
  • "a major amount" of a base oil of lubricating viscosity refers to a concentration of the oil within the lubricating oil composition of at least about 50 wt %, at least about 60 wt %, at least about 70 wt %, at least about 80 wt %, or at least about 90 wt %.
  • a 1 L glass reactor equipped with an agitator was charged with oleylamine (473.96 g, 1.80 mole based on an amine value of 213 mg KOH/g; available from Akzo Nobel as Armeen ® OLD) under a nitrogen atmosphere and heated to 100°C.
  • Glycerol carbonate (212.47 g, 1.80 mole; available from Huntsman as JEFFSOL ® glycerol carbonate) was added via an addition funnel over 2 hours. The reaction mixture was heated at 100°C for an additional 5 h.
  • a 500 mL glass reactor equipped with an agitator was charged with oleylamine (221.63 g, 0.84 mol based on an amine value of 213 mg KOH/g) under a nitrogen atmosphere and heated to 100°C.
  • Glycerol carbonate 99.35 g, 0.84 mol was added via an addition funnel over several minutes. The reaction mixture was heated at 100°C for an additional 4 h.
  • a 500 mL glass reactor equipped with an agitator was charged with oleylamine (217.53 g, 0.826 mole based on amine value of 213 mg KOH/g) under a nitrogen atmosphere and heated to 155°C.
  • Glycerol carbonate (97.52 g, 0.826 mol) was added via a syringe pump over 2 hours. The reaction mixture was heated at 160°C for an additional 4 h.
  • a 500 mL glass reactor equipped with an agitator was charged with dodecylamine (281.35 g, 1.52 mol) under a nitrogen atmosphere and heated to about 70°C.
  • Glycerol carbonate (179.24 g, 1.52 mol) was added via an addition funnel over several minutes. The reaction mixture was heated at 70°C for an additional 2.5 h.
  • a 1 L glass reactor equipped with an agitator was charged with oleylamine (462.61 g, 1.76 mol) under a nitrogen atmosphere and heated to about 160°C.
  • Glycerol carbonate (207.38 g, 1.76 mol) was added via an addition funnel over several minutes. The reaction mixture was heated at 160°C for an additional 4.5 h.
  • a 500 mL glass reactor equipped with an agitator was charged with oleylamine (256.15 g, 0.97 mol based on amine value of 213 mg KOH/g) under a nitrogen atmosphere and heated to about 70°C.
  • the reactor was placed in a cooling water bath to remove the heat of reaction and keep the reaction mixture temperature below 90°C.
  • Glycerol carbonate (114.83 g, 0.97 mol) was added via an addition funnel over several minutes. The reaction mixture was heated at 70°C for approximately an additional 3 h.
  • a 500 mL glass reactor equipped with an agitator was charged with oleylamine (327.20 g, 1.24 mol based on amine value of 213 mg KOH/g) under a nitrogen atmosphere and heated to about 70°C.
  • the reactor was placed in a cooling water bath to remove the heat of reaction and keep the reaction mixture temperature at about 70°C.
  • Ethylene carbonate (109.38 g, 1.24 mol) was added via a syringe pump over several minutes. The reaction mixture was heated at 70°C for approximately an additional 4 h.
  • a 500 mL glass reactor equipped with an agitator was charged with oleylamine (164.06 g, 1.27 mol) under a nitrogen atmosphere and heated to about 70°C.
  • the reactor was placed in a cooling water bath to remove the heat of reaction and keep the reaction mixture temperature at about 70°C.
  • Ethylene carbonate 111.8 g, 1.27 mol was added via a syringe pump over several minutes. The reaction mixture was heated at 70°C for approximately an additional 4 h.
  • This formulated oil comprised a lubricating oil and additives in their typical amounts for particular purpose; this included a zinc dialkyldithiophosphate, a mixture of calcium-containing detergents, a seal swell additive and a corrosion inhibitor.
  • the lubricating oil composition containing glycerol carbamate of Example 2 demonstrated comparable anti-wear properties to the lubricating oil composition containing glycerol monooleate.
  • This formulated oil comprised a 45N Group II lubricating oil and additives in their typical amounts for particular purpose; this included 4.0 wt. % succinimide 48.5 millimoles of a mixture of calcium containing detergents, 7 millimoles of a mixture of primary and secondary zinc dithiophosphates, 1.2 wt. % of an antioxidant, 0.5 wt. % of a suflurized/molybdated succinimide complex , 0.3 wt. % of a pour point depressant, 10 ppm of a foam inhibitor and 4.8 wt. % of a viscosity index improver.
  • This formulated oil comprised a 45N Group II lubricating oil and additives in their typical amounts for particular purpose; this included 4.0 wt. % succinimide 48.5 millimoles of a mixture of calcium containing detergents, 7 millimoles of a mixture of primary and secondary zinc dithiophosphates, 1.2 wt.
  • the formulated baseline oil was then top-treated with either 0.5 wt. % of Example 2 or 0.5 wt % of a borated glycerol monooleate, a conventional friction modifier.
  • the three formulations were then evaluated in a proprietary mini traction machine (MTM) friction test available from PCS Instruments.
  • MTM friction test applies a certain load between a steel ball and disk. The ball is rolling as well as sliding relative the disk. The load, speed is designed into a profile that covers all the friction conditions of a gasoline engine. While testing, the ball and the disk are immersed in the lubricating oil to evaluate the lubricating effect of this oil (meaning that the friction coefficient between the ball and disk is measured under this profile with the lubricating oil).
  • the lubricating oil composition containing glycerol carbamate demonstrated superior anti-friction properties to the lubricating oil composition containing glycerol monooleate.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
EP09837831.8A 2008-12-18 2009-12-09 Friction modifiers and/or wear inhibitors derived from hydrocarbyl amines and glycerol carbonate Active EP2376611B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12/337,813 US20100160198A1 (en) 2008-12-18 2008-12-18 Friction modifiers and/or wear inhibitors derived from hydrocarbyl amines and cyclic carbonates
PCT/US2009/067253 WO2010080308A2 (en) 2008-12-18 2009-12-09 Friction modifiers and/or wear inhibitors derived from hydrocarbyl amines and cyclic carbonates

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EP2376611A2 EP2376611A2 (en) 2011-10-19
EP2376611A4 EP2376611A4 (en) 2012-07-25
EP2376611B1 true EP2376611B1 (en) 2014-06-18

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US (1) US20100160198A1 (enExample)
EP (1) EP2376611B1 (enExample)
JP (1) JP5438773B2 (enExample)
CN (1) CN102282243B (enExample)
CA (1) CA2746937C (enExample)
SG (2) SG10201400731QA (enExample)
WO (1) WO2010080308A2 (enExample)

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SG10201400731QA (en) 2014-07-30
WO2010080308A3 (en) 2010-10-07
EP2376611A2 (en) 2011-10-19
EP2376611A4 (en) 2012-07-25
SG172245A1 (en) 2011-07-28
US20100160198A1 (en) 2010-06-24
CA2746937C (en) 2018-01-23
JP5438773B2 (ja) 2014-03-12
CN102282243B (zh) 2016-09-21
CN102282243A (zh) 2011-12-14
WO2010080308A2 (en) 2010-07-15
CA2746937A1 (en) 2010-07-15
JP2012512945A (ja) 2012-06-07

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