EP1354023A2 - Lubricating oil composition - Google Patents

Lubricating oil composition

Info

Publication number
EP1354023A2
EP1354023A2 EP02715390A EP02715390A EP1354023A2 EP 1354023 A2 EP1354023 A2 EP 1354023A2 EP 02715390 A EP02715390 A EP 02715390A EP 02715390 A EP02715390 A EP 02715390A EP 1354023 A2 EP1354023 A2 EP 1354023A2
Authority
EP
European Patent Office
Prior art keywords
oil composition
lubricating oil
propionic acid
weight
composition according
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.)
Ceased
Application number
EP02715390A
Other languages
German (de)
English (en)
French (fr)
Inventor
Yoshiharu Baba
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of EP1354023A2 publication Critical patent/EP1354023A2/en
Ceased legal-status Critical Current

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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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • 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
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02—Petroleum fractions
    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • C10M137/105—Thio derivatives not containing metal
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    • 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
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    • 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
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    • 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
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
    • C10M2203/1045—Aromatic fractions used as base material
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
    • C10M2203/1065—Naphthenic fractions used as base material
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • C10M2203/1085—Residual fractions, e.g. bright stocks used as base material
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    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/046—Hydroxy ethers
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    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2215/064—Di- and triaryl amines
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    • 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
    • C10M2215/30—Heterocyclic compounds
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    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for 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
    • C10N2040/135—Steam engines or turbines

Definitions

  • the present invention relates to a lubricating oil composition which exhibits excellent lubricating performance, even under severe high pressure/high load working conditions .
  • the use of industrial machines at higher speeds, under higher pressures, and the miniaturization thereof has resulted in machine elements such as hydraulic machines, compressors, turbines, gear elements and bearings being operated under severer conditions.
  • the lubricating oil used must therefore exhibit excellent lubricating performance to sufficiently guarantee the life of these machines over long periods even when they are used at high pressure, high speed, high load and high temperatures .
  • zinc dialkyl dithiophosphates have been used in anti-wear lubricating oil compositions for lubricating oils for industrial machines .
  • these compounds are disadvantageous in terms of their instability to hydrolysis on contamination with water and their instability to thermal oxidation at high temperature and high pressure, and in that an unpleasant odour is generated as the lubricating oil deteriorates .
  • Anti-wear lubricating oil compositions comprising sulphur compounds, phosphorous compounds and phosphorous- sulphur-based combinations thereof are already known as zinc-free anti-wear lubricating oils which do not contain zinc dialkyl dithiophosphates .
  • the present invention therefore aims to provide a lubricating oil composition which contains as little ash (e.g. zinc) as possible and has excellent anti-wear properties, even when used under severe high pressure, high speed and high load conditions, and which is excellent in terms of its thermal oxidation stability, water resistance and odour and also in terms of the 1 ⁇ environment, safety and its lubricating oil performance in practice.
  • as little ash e.g. zinc
  • the present invention provides a lubricating oil composition, comprising ⁇ -dithiophosphorylated propionic acid (A) , triaryl phosphate (B) and base oil comprising mineral oil and/or synthetic oil.
  • ⁇ -dithiophosphorylated propionic acid (A) is represented by the general formula (1) below: -
  • R 1 represents a branched alkyl group of from 3 to 8 carbon atoms, preferably from 3 to 4 carbon atoms
  • R 2 represents a hydrogen atom or an alkyl group of from 1 to 4 carbon atoms
  • Rl can be chosen from the following branched alkyl groups:- isopropyl group, branched butyl group, branched pentyl group, branched hexyl group, branched heptyl group, and branched octyl group.
  • R 2 include hydrogen, methyl, ethyl, propyl and butyl groups .
  • R 2 is a methyl group, ethyl group or hydrogen group. It is particularly preferred that R 2 is methyl .
  • Such compounds include 3- (O,0-diisopropyldithiophosphoryl) propionic acid,
  • (A) added in the present invention is preferably from 0.001 to 1.0 % by weight, more preferably from 0.001 to 0.5 % by weight, even more preferably from 0.001 to 0.1 % by weight, and most preferably from 0.005 to 0.05 % by weight, with respect to the total amount of lubricating oil composition.
  • the triaryl phosphate (B) is represented by the general formula (2) below: -
  • 0 P(-0-R 3 ) 3 (2) wherein each 3 is independently a phenyl group or a phenyl group having alkyl group (s) of from 1 to 9 carbon atoms .
  • suitable triaryl phosphates (B) include triphenyl phosphate ester, tricresyl phosphate ester, triethyl phenyl phosphate ester, tripropyl phenyl phosphate ester, tributyl phenyl phosphate ester, triheptyl phenyl phosphate ester, trihexyl phenyl phosphate ester, triheptyl phenyl phosphate ester, trioctyl phenyl phosphate ester and trinonyl phenyl phosphate ester .
  • the amount of triaryl phosphate (B) used in the present invention is preferably from 0.05 to 10 % by weight, more preferably from 0.05 to 5 % weight and most preferably from 0.1 to 2 % by weight with respect to the total amount of lubricating oil base oil.
  • the lubricating oil composition exhibits wear corresponding to no more than 150 mg, which meets DIN 51524 (Part 2) standard, in a "Vickers V104 C" vane pump test (according to IP 281) .
  • the lubricating oil composition exhibits vane wear corresponding to no more than 15 mg and ring wear corresponding to no more than 75 mg, which meets "Vickers" standard M-2950-S, in a "Vickers 35VQ25A” vane pump test (according to "Vickers” M-2950-S) .
  • the lubricating oil composition exhibits vane wear corresponding to no more than 10 mg and ring wear corresponding to no more than 50 mg, which meets "General Motors” Standard LS-2LH.03.04.06, in a "Vickers 35VQ25A" vane pump test (according to "Vickers” M-2950-S) .
  • the lubricating oil composition according to the present invention may be used as a hydraulic oil composition, a compressor oil composition, a turbine oil composition, a bearing oil composition, and/or a gear oil composition.
  • said base oil in the lubricating oil composition of the present invention.
  • said base oil is petroleum-based, synthetic hydrocarbon-based and/or ester-based.
  • the preferred physical properties of the base oil are as follows : a kinematic viscosity of from 2 to 680 mm 2 /s (40°C) , preferably from 5 to 320 mm 2 /s (40°C) and more preferably from 8 to 220 mm 2 /s (40 °C) ; a total sulphur content (% by weight) of from 0 to 1% and preferably from 0 to 0.3%; a total nitrogen content (weight ppm) of from 0 to
  • Petroleum-based lubricating oil base oils which can be used in the present invention include solvent purified base oil, hydrogenation purified base oil and highly hydrocracked base oil. Such base oils can be used individually or as mixtures.
  • Highly hydrocracked base oil is a base oil having a viscosity index of at least 130 (typically from 145 to
  • Said base oil can be obtained by taking a starting material wax (slack wax) which has been separated by solvent dewaxing, and hydrogenating said wax in the presence of a catalyst (catalytic degradation) to convert linear paraffin to branched paraffin.
  • said base oil can be obtained by taking as starting material the hydrogen and carbon monoxide obtained by subjecting natural gas (methane or the like) to the gas formation process (partial oxidation) , then subjecting said starting material to Fischer-Tropsch polymerisation to yield heavy linear paraffin, and then modifying said heavy linear paraffin to catalytic degradation as described above .
  • the synthetic hydrocarbon-based base oil used in the present invention can be an olefin oligomer obtained by homopolymerizing or copolymerizing monomer chosen from linear or branched olefinic hydrocarbons of from 3 to 15, preferably from 4 to 12 , carbon atoms .
  • petroleum-based base oil or synthetic hydrocarbon-based base oil can be used individually, or in mixtures thereof.
  • Triaryl phosphate esters have long been known as anti-wear agents for use under relatively mild conditions, and, as disclosed in US Patent Number 5922657 (corresponding to Japanese Unexamined Patent Application Number H10-67993) , ⁇ -dithiophosphorylated propionic acid is known to improve extreme pressure performance and prevent gear seizure.
  • the anti-wear properties under severe high pressure/high load conditions can be improved to equivalent to or better than those achieved when ⁇ -dithiophosphorylated propionic acid is used alone, by the combined use of the abovementioned anti-wear component triarylphosphate ester.
  • various other commonly used additives may also be added if necessary in the present invention in order to further improve performance .
  • lubricating oil additives such as antioxidant, rust preventer, metal deactivator, detergent dispersant, anti- wear agent, extreme-pressure agent, friction regulator, flow point depressor, viscosity index improver, anti- emulsification agent and defoamer.
  • examples of amine-based antioxidants include dialkyldiphenylamines such as p,p' -dioctyl- diphenylamine (manufactured by Seiko Kagaku under the trade designation "Nonflex OD-3"), p,p'-di- ⁇ - methylbenzyldiphenylamine and N-p-butylphenyl-N-p' - octylphenylamine; monoalkyldiphenylamines such as mono-t- butyldiphenylamine and monooctyldiphenylamines; bis (dialkylphenyl) amines such as di(2,4- diethylphenyl) amine and di (2-ethyl-4-nonylphenyl) amine; alkylphenyl-1-naphthylamines such as octylphenyl-1- naphthylamine and N-t-dodecylpheny
  • sulphur-based antioxidants examples include dialkyl sulphates such as didodecyl sulphate and dioctadecyl sulphate, thiodipropionic acid esters such as didodecyl thiodipropionate, dioctadecyl thiodipropionate, dimyristyl thiodipropionate and dodecyloctadecyl thiodipropionate, and 2-mercaptobenzimidazole.
  • dialkyl sulphates such as didodecyl sulphate and dioctadecyl sulphate
  • thiodipropionic acid esters such as didodecyl thiodipropionate, dioctadecyl thiodipropionate, dimyristyl thiodipropionate and dodecyloctadecyl thiodipropionate
  • phenol-based antioxidants examples include 2,6- di-t-butyl-4-alkylphenols such as 2-t-butylphenol, 2-t- butyl-4-methylphenol, 2-t-butyl-5-methylphenol, 2,4-di-t- butylphenol, 2, 4-dimethyl-6-t-butylphenol, 2-t-butyl-4- methoxyphenol , 3-t-butyl-4-methoxyphenol, 2,5-di-t- butylhydroquinone (manufactured by Kawaguchi Kagaku under the trade designation "Antage DBH") , 2,6-di-t- butylphenol, 2, 6-di-t-butyl-4-methylphenol and 2,6-di-t- butyl-4-ethylphenol; 2, 6-di-t-butyl-4-alkoxyphenols such as 2, 6-di-t-butyl-4-methoxyphenol and 2, 6-di-t-butyl-4- ethoxyphenol
  • phosphorous-based antioxidants examples include triaryl phosphites such as triphenyl phosphite and tricresyl phosphite, trialkyl phosphites such as trioctadecyl phosphite and tridecyl phosphite, and tridodecyl trithiophosphite .
  • antioxidants can be used individually, or a plurality can be used in combination, and the amount added thereof may conveniently be from 0.01 to 2.0 parts by weight per 100 parts by weight of base oil.
  • (dodecyldithio) benzimidazole, and 2- (alkyldithio) - toluimidazoles such as 2- (octyldithio) toluimidazole, 2- decyldithio) toluimidazole and 2- (dodecyldithio) - toluimidazole; indazole, and indazole derivatives, for example, toluindazoles such as 4-alkyl-indazole and 5- alkyl-indazole; benzothiazole, and benzothiazole derivatives, for example, 2- (alkyldithio) benzothiazoles such as 2-mercaptobenzothiazole derivative (manufactured by Chiyoda Kagaku under the trade designation "Thiolite B-3100"), 2- (hexyldithio) -benzothiazole and 2-
  • metal deactivators can be used individually, or a plurality can be used in combination, and the amount added thereof may conveniently be from 0.005 to 0.5 parts by weight per 100 parts by weight of base oil.
  • defoamers which can be used include organosilicates such as dimethylpolysiloxane, diethyl silicate and fluorosilicone, and non-silicone defoamers such as polyalkyl acrylates . These can be used individually or a plurality can be used in combination, and the amount added thereof may conveniently be from
  • viscosity index improvers examples include non- dispersant-type viscosity index improvers for example, polymethacrylates and olefin copolymers such as ethylene/propylene copolymer and styrene/diene copolymer, and dispersion-type viscosity index improvers such as those obtained by copolymerizing these with nitrogen- containing monomers .
  • the amount added thereof may conveniently be from 0.05 to 20 parts by weight per 100 parts by weight of base oil .
  • flow point depressors examples include polymethacrylate-based polymers. The amount added thereof may conveniently be from 0.01 to 5 parts by weight per 100 parts by weight of base oil. '
  • detergent dispersants include metal- based detergents, for example, neutral or basic alkaline earth metal sulphonates, alkaline earth metal phenates and alkaline earth metal salicylates, and ashless dispersants, for example modified products obtained from alkenyl succinate imides, alkenyl succinate esters or boron compounds, sulphur compounds etc. thereof. These can be used individually or a plurality can be used in combination, and the amount added thereof may conveniently be from 0.01 to 1 parts by weight per 100 parts by weight of base oil .
  • extreme-pressure agents and friction regulators include sulphur-based extreme-pressure agents such as dialkyl sulphides, dibenzyl sulphide, dialkyl polysulphides, dibenzyl disulphide, alkyl mercaptans, dibenzothiophene and 2, 2' -dithiobis (benzothiazole) ,- phosphorous-based extreme-pressure agents such as trialkyl phosphates, trialkyl phosphonates, trialkyl phosphites, triaryl phosphites, dialkyl hydrogen phosphites, trialkyl trithiophosphites and triaryl phosphorothioates; aliphatic friction regulators such as fatty acid amides and fatty acid esters; amine-based friction regulators such as primary to tertiary alkylamines and alkylene oxide adducts of alkyl amines; and extreme-pressure agents such as zinc alkyl dithiophosphates.
  • rust preventers examples include N-alkylsarcosinic acids, alkylate phenoxy acetates, imidazolines, "KX1031" manufactured by King Industry and alkaline earth metal salts thereof and amine salts thereof, the N-acyl-N-alkoxyalkyl asparginate esters disclosed in Japanese Unexamined Patent Application Number H6-200268, the alkaline earth metal salts of phosphate esters disclosed in EP-A-0801116 and alkenyl succinate ester-based rust preventers . These rust preventers can be used individually or a plurality can be used in combination, and the amount added may conveniently be in the range of from 0.005 to 1.0 parts by weight can be used per 100 parts by weight of base oil.
  • anti-emulsifying agents used to break up emulsions to allow separation into two liquid layers
  • examples of anti-emulsifying agents include commonly known substances which are usually used as lubricating oil additives, for example, polyalkylene glycol-based nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers and polyoxyethylene alkyl naphthyl ethers .
  • the amount added may conveniently be in the range of from 0.0005 to 0.5 parts by weight per 100 parts by weight of base oil. It is particularly appropriate to use the lubricating oil composition of the present invention as a hydraulic oil composition as described above.
  • said lubricating oil composition can also be used in other ways, for example, as a compressor oil composition, turbine oil composition, bearing oil composition or gear oil composition.
  • test oil having a kinematic viscosity of 32 mm 2 /s at 40°C.
  • the pump test was performed for 50 h at a pressure of 210 kgf/cm 2 , 2400 rpm, oil temperature 93 °C using a "Vickers 35VQ-25A" pump, and the wear on the vane and ring was measured after the test .
  • the "Vickers" M-2950-S criterion is that the vane wear be equivalent to no more than 15 mg and the ring wear be equivalent to no more than 75 mg.
  • the "General Motors" LS-2 LH.03.04.06 criteria are stricter: vane wear corresponding to no more than 10 mg and ring wear corresponding to no more than 50 mg.
  • Component 1 is a ⁇ - dithiophosphorylated propionic acid represented by general formula (1) in which R 1 is an isobutyl group and R 2 is a methyl group .
  • Component 2 in Tables 2 and 3 is a triarylphosphate sold under the trade designation "Reofos 65" ex. Aj inomoto .
  • Component 3 is a ⁇ -dithiophosphorylated propionic acid represented by the general formula (1) in which R ⁇ is an isobutyl group and R 2 is a hydrogen group.
  • Triphenylphosphorothioate in Table 3 is that sold under the trade designation "Irgalube TPPT" ex. Ciba. TABLE 4
  • Comparative Examples 1 and 2 did not exhibit adequate anti-wear properties in the "Vickers V104C” vane pump test and did not have the anti-wear properties required to pass German Standard DIN 51524 (part 2) .
  • Comparative Examples 3 and 4 did pass German Standard DIN 51524 (part 2) in the "Vickers V104C” vane pump test, but did not exhibit adequate anti-wear properties in the "Vickers 35VQ25A” vane pump test and did not pass the "Vickers” M-2950-S standard or "General Motors" LS-2 LH.03.04.06 standard.
  • Comparative Examples 7 and 8 exhibited anti-wear properties sufficient to pass German Standard DIN 51524 (part 2) in the V104C vane pump test, but their anti-wear properties were not sufficient to pass the "Vickers” M-2950-S standard or the "General Motors” LS-2-LH.03.04.06 standard.
  • the lubricating oil composition according to the present invention (Working Examples 1 and 2) have excellent anti-wear properties sufficient to pass German Standard DIN 51524 (Part 2) , "Vickers” M-2950-S standard and “General Motors” LS-2 LH.03.04.06 standard, in vane pump tests “Vickers” V104C and 35VQ25A, and their lubricating oil performance is sufficient for use as a hydraulic oil in high-pressure applications. Comparative Example 5 shows increased total wear in both tests when compared to Working Examples 1 and 2.
  • Comparative Examples 9 and 10 were performed in order to see whether the thermal oxidative stability is better when R 2 in the ⁇ -dithiophosphorylated propionic acid is hydrogen or when it is a methyl group.
  • the composition and results for Comparative Examples 9 and 10 are shown in Table 6.
  • the thermal oxidative stability test was performed as follows: 200 ml of test oils of Comparative Examples 9 and 10, obtained by combining ⁇ -dithiophosphorylated propionic acid and antioxidant and rust preventer, were independently introduced into 250 ml beakers, a steel sample and copper sample of diameter 0.6 mm and length 7.6 mm, which had been polished using # 240 alumina polishing paper, washed and dried, were intersected and the test oils were applied thereto, and the test oils were subjected to thermal oxidative deterioration for 336 hours in a 140°C oven, and after the test the test oils were suction-filtered using a 0.8 ⁇ m hole diameter filter and the amount of sludge obtained, the external appearance of the copper sample and steel sample and the colour of the test oil (ASTM D1500) were measured.
  • the compound of Comparative Example 10 in which one of the hydrogen atoms on the ⁇ -carbon of the ⁇ -dithiophosphorylated propionic acid has been substituted by an alkyl group undergoes less change in colour and produces less sludge, that is, is more stable, than the compound of Comparative Example 9 in which there is no alkyl substitution of the hydrogen atoms on the ⁇ -carbon. If there are too many carbon atoms in the alkyl group substitutions on the ⁇ - carbon, anti-wear properties deteriorate and so in order to achieve both thermal oxidative stability and anti-wear properties, the alkyl group substituent is most preferably a methyl group .
  • Lubricating oil compositions of the present invention contain no, or almost no, ash-forming substances such as zinc dialkyl dithiophosphates, in view of environmental and safety considerations; the resulting anti-wear lubricating oil compositions exhibit excellent anti-wear with respect to various machine elements even when used under severe high pressure, high speed and high load conditions. Accordingly, the lubricating oil compositions of the present invention are highly effective in the provision of lubricating oil which can guarantee the reliability of equipment over long periods, in response to the recently developed high speed, high pressure and high precision industrial machines.

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WO2002053687A2 (en) 2002-07-11
JP2002265971A (ja) 2002-09-18
CN1484688A (zh) 2004-03-24
JP4789335B2 (ja) 2011-10-12
WO2002053687A3 (en) 2002-09-19
US20040053794A1 (en) 2004-03-18
AU2002224973B2 (en) 2006-08-31
KR20030065589A (ko) 2003-08-06
BR0206298A (pt) 2004-01-13
CA2433447A1 (en) 2002-07-11
KR100850654B1 (ko) 2008-08-07

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