WO2008095966A1 - Lubricating oil composition - Google Patents

Lubricating oil composition Download PDF

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Publication number
WO2008095966A1
WO2008095966A1 PCT/EP2008/051470 EP2008051470W WO2008095966A1 WO 2008095966 A1 WO2008095966 A1 WO 2008095966A1 EP 2008051470 W EP2008051470 W EP 2008051470W WO 2008095966 A1 WO2008095966 A1 WO 2008095966A1
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WO
WIPO (PCT)
Prior art keywords
lubricating oil
oil composition
composition according
group
carbon number
Prior art date
Application number
PCT/EP2008/051470
Other languages
English (en)
French (fr)
Inventor
Mitsuhiro Nagakari
Hiroshi Kaneko
Yoshiharu Baba
Original Assignee
Showa Shell Sekiyu K.K.
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 Showa Shell Sekiyu K.K. filed Critical Showa Shell Sekiyu K.K.
Priority to US12/447,636 priority Critical patent/US20100105590A1/en
Priority to EP08708758A priority patent/EP2109657A1/en
Publication of WO2008095966A1 publication Critical patent/WO2008095966A1/en

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    • 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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • 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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/02—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic oxygen-containing compound
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
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    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
    • C—CHEMISTRY; METALLURGY
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    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
    • C—CHEMISTRY; METALLURGY
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    • C10M141/12—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic compound containing atoms of elements not provided for in groups C10M141/02 - C10M141/10
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    • 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
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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
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    • 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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    • 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
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    • C10M2205/17—Fisher Tropsch reaction products
    • C10M2205/173—Fisher Tropsch reaction products used as base material
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C10M2207/127—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids polycarboxylic
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • 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
    • 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
    • C10N2040/30—Refrigerators lubricants or compressors lubricants

Definitions

  • the present invention relates to lubricating oil compositions, in particular to be used as industrial lubricating oils, in particular to lubricating oil compositions used as for example machine oil, hydraulic fluid, turbine oil, compressor oil, gear oil, sliding surface oil, bearing oil or calibration oil.
  • Lubricating oil employed for mechanical equipment is required to be essentially rustproof in order to maintain its performance.
  • Reasons for this include: raising and lowering of the lubricating oil temperature in the tank in the mechanical equipment, depending on conditions of use, which may cause admixture of condensed water with the lubricating oil in the tank; and admixture of moisture that may occur due to leakage of water from the cooling water piping.
  • Aspartic acid esters etc are employed in order to obtain such rustproofing. See Laid- open Japanese Patent Application No. H. 6-200268.
  • a problem that the invention intends to solve is to obtain an industrial lubricating oil having excellent anti-rust properties and low friction, thereby permitting a high degree of energy-saving.
  • a lubricating oil composition that solves this problem is employed as the hydraulic fluid in hydraulic equipment, it becomes possible to control the hydraulic equipment accurately without phenomena such as hydraulic cylinder chattering, vibration, squeaking, or generation of abnormal noise.
  • the present invention seeks to obtain a lubricating oil composition whereby generation of rust is suppressed, and that has excellent energy-saving properties and operating efficiency .
  • a lubricating oil composition that is ideal as an industrial lubricating oil such as for example hydraulic fluid can be obtained by adding as additives an aspartic acid derivative and aliphatic amine compound to highly refined base oil and/or synthetic base oil.
  • a primary amine, secondary amine, diamine, or tertiary amine etc. may be employed as the aliphatic amine compound referred to above.
  • an excellent lubricating oil composition whereby generation of rust is suppressed and that is of low coefficient of friction can be obtained.
  • the frictional losses that are generated in various types of industrial equipment can be effectively decreased, making it possible to achieve energy-saving.
  • phenomena such as chattering of the hydraulic cylinder, vibration, squeaking, or generation of abnormal noise can be eliminated and the hydraulic eguipment can be controlled accurately.
  • base oil of the present lubricating oil composition mineral oil, called highly refined base oil, or synthetic oil may be employed: in particular, base oil in the base oil category of the API (American Petroleum Institute) belonging to Group I, Group II, Group III or Group IV etc. may be employed, either alone or as a mixture.
  • the base oil that is here employed may be of elementary sulphur content no more than 700 ppm, preferably no more than 500 ppm. Its density may be 0.8 to 0.9.
  • the aromatic fraction may be less than 5%, preferably less than 3%.
  • Group I base oil includes for example paraffin-type mineral oil obtained by suitable combination of refining means such as solvent refining, hydrofining, and dewaxing of the lubricating oil fraction obtained by normal pressure distillation of crude oil.
  • the index of viscosity may be 80 to 120, preferably 95 to 110 (ASTM D2270) .
  • the kinetic viscosity at 40 0 C is preferably 2 to 680 mm 2 /s, and even more preferably 8 to 220 mm 2 /s (ASTM D445) .
  • the total sulphur may be less than 700 ppm, preferably less than 500 ppm.
  • the total nitrogen may be less than 50 ppm, preferably less than 25 ppm.
  • the aniline point may be 80 to 150 0 C, preferably 90 to 122 0 C.
  • Group II base oil includes for example paraffin-type mineral oil obtained by suitable combination of refining means such as hydrocracking and dewaxing of the lubricating oil fraction obtained by normal pressure distillation of crude oil.
  • Group II base oil refined by for example Gulf Oil's hydrofining method has total sulphur of less than 10 ppm and aromatic content less than 5% and is ideal in the present invention.
  • the viscosity of such base oil and the viscosity index may be 80 to 120, preferably 100 to 120.
  • the kinetic viscosity at 40 0 C is preferably 2 to 680 mm 2 /s and even more preferably 8 to 220 mm 2 /s.
  • the total sulphur may be less than 300 ppm, preferably less than 200 ppm, and even more preferably less than 10 ppm.
  • the total nitrogen may be less than 10 ppm, preferably less than 1 ppm.
  • the aniline point may be 80 to 150 0 C, preferably 100 to 135 0 C.
  • Group III base oil and Group II base oil there may suitably be employed for example paraffin-type mineral oil manufactured by a high degree of hydrofining of the lubricating oil fraction obtained by normal pressure distillation of crude oil or base oil generated by a dewaxing process, involving refining by the ISODEWAX process, in which dewaxing is performed by converting wax to isoparaffins, or base oil refined by Mobil's wax isomerization process .
  • the viscosity index may be 95 to 145, preferably 100 to 140.
  • the kinetic viscosity at 40 0 C is preferably 2 to 680 mm 2 /s and even more preferably 8 to 220 mm 2 /s.
  • the total sulphur may be 0 to 100 ppm, preferably less than 10 ppm.
  • the total nitrogen may be less than 10 ppm, preferably less than 1 ppm.
  • the aniline point may be 80 to 150 0 C, preferably 100 to 135 0 C.
  • GTL Gas To Liquid
  • Tropsch technique of converting natural gas to a liquid is ideal as the base oil according to the present invention, since it has extremely low sulphur content and aromatic content and its paraffin constituent ratio is extremely high, and since it is of excellent oxidation stability and shows very little evaporation loss, compared with mineral base oil refined from crude oil.
  • the viscosity index will be 130 to 180, more preferably 140 to 175.
  • the kinetic viscosity at 40 0 C is preferably 2 to 680 mm 2 /s and even more preferably 5 to 120 mm 2 /s.
  • the total sulphur is usually less than 10 ppm, and the total nitrogen less than 1 ppm.
  • An example of such a GTL base oil product is SHELL XHVI (Registered Trademark) .
  • synthetic oils examples include: polyolefins, alkyl benzenes, alkyl naphthalenes, esters, polyoxyalkylene glycols, polyphenyl esters, dialkyl diphenyl ethers, fluorine-containing compounds (for example perfluoro polyethers, or polyolefin fluorides), or silicone oils.
  • the polyolefins referred to above include polymers of various types of olefins and hydrides of these. Although the olefins may be chosen at will, specific examples that may be given include ethylene, propylene, butene, or ⁇ -olefins of carbon number 5 or more. In the manufacture of the polyolefins, one of the above olefins may be employed alone, or two or more may be employed in combination. In particular, polyolefins called poly- ⁇ - olefins (PAO) are ideal: these constitute Group IV base oils .
  • PAO poly- ⁇ - olefins
  • the content of the above base oil in the lubricating oil composition according to the present invention may be 60 weight%, preferably at least 80 weight%, more preferably at least 90 weight% and yet more preferably at least 95 weight% with reference to the total amount of the lubricating oil composition.
  • Xi and X 2 are respectively hydrogen or alkyl groups, alkenyl groups or hydroxyalkyl groups of carbon number 3 to 6, that may be the same or different, and may preferably respectively be 2-methyl propyl groups or tertiary butyl groups.
  • X 3 may be an alkyl group or alkenyl group, alkyl group having an ether bond, or a hydroxyalkyl group, of carbon number 1 to 30.
  • X 4 may be a saturated or unsaturated carboxylic acid group of carbon number 1 to 30, or an alkyl group, alkenyl group or hydroxyalkyl group of carbon number 1 to 30.
  • Examples are a propionic acid group or propionylic acid group .
  • the aspartic acid derivative may be of acid value 10 to 200 mgKOH/g, preferably 50 to 150 mgKOH/g, as determined by JIS K2501.
  • the aspartic acid derivative may be employed in the amount of about 0.01 to 5 weight%, preferably about 0.05 to 2 weight%, in the lubricating oil composition.
  • a single aspartic acid derivative, or a mixture of derivatives of a number of types may be employed.
  • This lubricating oil composition may be blended with an aliphatic amine compound.
  • aliphatic amine compounds that may be mentioned include primary amines indicated by the general formula (2), secondary amines indicated by the general formula (3), diamines indicated by the general formula (4) and tertiary amines indicated by the general formula (5) .
  • X 5 is an alkyl group or alkenyl group of carbon number 1 to 30. Examples that may be mentioned include: laurylamine, coconut amine, n- tridecylamine, myristylamine, n-pentadecylamine, n- palmitylamine, n-heptadecylamine, n-stearylamine, isostearylamine, n-nonadecylamine, n-eicosylamine, n- heneicosylamine, n-docosylamine, n-tricosylamine, n- pentacosylamine, oleylamine, tallow amine, tallow amine hydride, and soybean amine.
  • X 5 is of carbon number 8 to 24 and more preferably of carbon number 12 to 18.
  • X 5 may be a straight chain aliphatic, a branched chain aliphatic or tertiary alkyl group.
  • X 6 and X 7 are an alkyl group or alkenyl group of carbon number 1 to 30. Examples that may be cited include: dilaurylamine, di- coconut amine, di-n-tridecylamine, di-myristylamine, di- n-pentadecylamine, di-n-palmitylamine, di-n- heptadecylamine, di-n-stearylamine, di-isostearylamine, di-n-nonadecylamine, di-n-eicosylamine, di-n- heneicosylamine, di-n-docosylamine, di-n-tricosylamine, di-n-pentacosylamine, di-oleylamine, di-tallow amine, di- tallow amine hydride, and di-soybean amine.
  • X 6 and X 7 are of carbon number 8 to 24 and more preferably of carbon number 12
  • X 8 may be an alkyl group or alkenyl group of carbon number 1 to 30.
  • X 8 is of carbon number 8 to 24 and more preferably of carbon number 12 to 18.
  • X 9 is an alkylene group of carbon number 1 to 12.
  • X 9 is of carbon number 1 to 8, and more preferably of carbon number 2 to 4.
  • Examples that may be cited include ethylene diamines such as: N-octyl-1, 2-ethylene diamine, N-nonyl-1,2- ethylene diamine, N-decyl-1, 2-ethylene diamine, N- undecyl-1, 2-ethylene diamine, N-lauryl-1, 2-ethylene diamine, N-tridecyl-1, 2-ethylene diamine, N-myristyl-1, 2- ethylene diamine, N-tetradecyl-1, 2-ethylene diamine, N- pentadecyl-1, 2-ethylene diamine, N-palmityl-1, 2-ethylene diamine, N-heptadecyl-1, 2-ethylene diamine, N-oleyl-1, 2- ethylene diamine, N-stearyl 1, 2-ethylene diamine, N- isostearyl 1, 2-ethylene diamine, N-nonadecyl 1, 2-ethylene diamine, N-eicosyl 1, 2-ethylene diamine, N-coconut-1, 2- ethylene diamine, N-tallow 1, 2-ethylene
  • propylene diamines such as: N-octyl-1, 3-propylene diamine, N-nonyl- 1, 3-propylene diamine, N-decyl-1, 3-propylene diamine, N- undecyl-1, 3-propylene diamine, N-lauryl-1, 3-propylene diamine, N-tridecyl-1, 3-propylene diamine, N-myristyl- 1, 3-propylene diamine, N-tetradecyl-1, 3-propylene diamine, N-pentadecyl-1, 3-propylene diamine, N-palmityl- 1, 3-propylene diamine, N-heptadecyl-1, 3-propylene diamine, N-oleyl-1, 3-propylene diamine, N-stearyl 1,3- propylene diamine, N-isostearyl 1, 3-propylene diamine, N- nonadecyl 1, 3-propylene diamine, N-e
  • examples that may be cited include butylene diamines such as: N-octyl-1, 4-butylene diamine, N-nonyl- 1,4-butylene diamine, N-decyl-1, 4-butylene diamine, N- undecyl-1, 4-butylene diamine, N-lauryl-1, 4-butylene diamine, N-tridecyl-1, 4-butylene diamine, N-myristyl-1, 4- butylene diamine, N-tetradecyl-1, 4-butylene diamine, N- pentadecyl-1, 4-butylene diamine, N-palmityl-1, 4-butylene diamine, N-heptadecyl-1, 4-butylene diamine, N-oleyl-1, 4- butylene diamine, N-stearyl 1, 4-butylene diamine, N- isostearyl 1, 4-butylene diamine, N-nonadecyl 1, 4-butylene diamine, N-
  • Xi 0 may be an alkyl group or alkenyl group of carbon number 1 to 30.
  • Xi 0 is of carbon number 1 to 20, but is more preferably of carbon number 1 to 8 or 12 to 18.
  • Xn is an alkyl group, alkenyl group, or hydroxyalkyl group of carbon number 1 to 20: preferably the carbon number of Xn is 1 to 8 or 12 to 18.
  • Xi 0 is a methyl group
  • dialkyl methylamines such as : dioctyl methylamine, dinonyl methylamine, didecyl methylamine, diundecyl methylamine, dilauryl methylamine, ditridecyl methylamine, dimyristyl methylamine, ditetradecyl methylamine, dipentadecyl methylamine, dipalmityl methylamine, diheptadecyl methylamine, dioleyl methylamine, distearyl methylamine, diisostearyl methylamine, dinonadecyl methylamine, dieicosyl methylamine, di-coconut-methylamine, di-tallow methylamine, di-tallow methylamine hydride, and di- soybean methylamine.
  • examples of the case where Xn is a methyl group include alkyl dimethylamines such as : octyl dimethylamine, nonyl dimethylamine, decyl dimethylamine, undecyl dimethylamine, lauryl dimethylamine, tridecyl dimethylamine, myristyl dimethylamine, tetradecyl dimethylamine, pentadecyl dimethylamine, palmityl dimethylamine, heptadecyl dimethylamine, oleyl dimethylamine, stearyl dimethylamine, isostearyl dimethylamine, nonadecyl dimethylamine, eicosyl dimethylamine, coconut-dimethylamine, tallow dimethylamine, tallow dimethylamine hydride, and soybean dimethylamine .
  • alkyl dimethylamines such as : octyl dimethylamine, nonyl dimethylamine, decyl dimethylamine, undecyl dimethylamine, lauryl dimethylamine, tri
  • examples of the case where Xn is a hydroxyalkyl group include N-alkyl diethanolamines such as: N-octyl diethanolamine, N-nonyl diethanolamine, N- decyl diethanolamine, N-undecyl diethanolamine, N-lauryl diethanolamine, N-tridecyl diethanolamine, N-myristyl diethanolamine, N-tetradecyl diethanolamine, N-pentadecyl diethanolamine, N-palmityl diethanolamine, N-heptadecyl diethanolamine, N-oleyl diethanolamine, N-stearyl diethanolamine, N-isostearyl diethanolamine, N-nonadecyl diethanolamine, N-eicosyl diethanolamine, N-coconut diethanolamine, N-tallow diethanolamine, N-tallow diethanolamine hydride, and N-soybean diethanolamine; and N-alkyl dipropano
  • the aliphatic amine referred to above may be of base value 10 to 800 mg KOH/g as determined by JIS K2501, but is preferably of base value of 100 to 500 mg KOH/g. At least one such aliphatic amine, selected from the above group, may be employed in an amount of about 0.05 to 5 weight%, preferably about 0.01 to 1 weight%, in the lubricating oil composition, either alone or in suitable combination .
  • additives may be suitably employed as required.
  • these additives include antioxidants, metal deactivators, extreme pressure agents, oiliness improvers, anti-foaming agents, viscosity index improvers, pour-point depressants, detergent-dispersants, rust inhibitors, anti-rust agents, demulsifiers etc. or other known lubricating oil additives.
  • antioxidants that are employed in lubricating oils are practically preferable; examples that may be mentioned include: phenol-based antioxidants, aromatic amine-based antioxidants, sulphur-based antioxidants and phosphorus-based antioxidants .
  • One or a combination of more than one of these antioxidants may be employed in the range of 0.01 to 5 weight% with respect to 100 weight% of base oil.
  • aromatic amine-based antioxidants examples include: dialkyl diphenylamines such as p, p ' -dioctyl diphenylamine (manufactured by Seiko Chemicals Inc: Non-flex OD-3), p, p ' -di- ⁇ -methylbenzyl diphenylamine, or N-p-butylphenyl-N-p ' -octylphenylamine; monoalkyl diphenylamines such as mono-t-butyl diphenylamine or mono-octyl diphenylamine; bis (dialkylphenyl) amines such as di(2,4- diethylphenyl) amine, or di (2-ethyl-4-nonylphenyl) amine; alkylphenyl-1-naphthylamines such as octylphenyl-1- naphthylamine or N-t-dodec
  • phenol-based antioxidants examples include 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-butyl hydroquinone (manufactured by Kawaguchi Chemicals Inc: Antage DBH), 2,6-di-t- butylphenol, 2, 6-di-t-butyl-4-alkylphenols, such as 2,6- di-t-butyl-4-methylphenol, or 2, 6-di-t-butyl-4- ethylphenol; or 2, 6-di-t-butyl-4-alkoxyphenols such as 2, 6-di-t-butyl-4-methoxyphenol or 2, 6-di-t-butyl-4- ethoxyphenol .
  • alkyl-3- 3-, 5-di-t-butyl-4- hydroxyphenyl) propionates such as 3, 5-di-t-butyl-4- hydroxybenzyl mercapto-octyl acetate, n-octadecyl-3- (3,
  • 5-di-t-butyl-4-hydroxyphenyl) propionate (manufactured by Yoshitomi Seiyaku Inc: Yoshinox SS), n-dodecyl-3- (3, 5-di- t-butyl-4-hydroxyphenyl) propionate, 2 ' -ethylhexyl-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate, or benzene propanoate 3, 5-bis ( 1, 1-dimethyl-ethyl) -4-hydroxy-C7 to C9 side-chain alkyl ester (manufactured by Ciba Speciality Chemicals Inc: Irganox L135), or 2, 2 ' -methylene bis (bis 4-alkyl-6-t-butylphenol) such as 2, 6-di-t-butyl- ⁇ - dimethylamino-p-cresol, 2, 2 ' -methylene bis ( 4-methyl-6-t- butylphenol) (
  • Yet further examples include bisphenols such as 4, 4 ' -butylidene bis (3-methyl-6-t-butylphenol) (manufactured by Kawaguchi Chemicals Inc: Antage W-300), 4, 4 ' -methylene bis (2, 6-di-t-butylphenol) (manufactured by Shell Japan Inc: Ionox 220 AH), 4 , 4 ' -bis (2, 6-di-t-butylphenol) , 2,2- (di-t-hydroxyphenyl ) propane (manufactured by Shell Japan Inc: bisphenol A), 2, 2-bis (3, 5-di-t-butyl-4- hydroxyphenyl) propane, 4, 4 ' -cyclohexylidene bis(2,6-t- butylphenol ) , hexamethylene glycol bis [3- ( 3, 5-di-t-butyl- 4-hydroxyphenyl) propionate] (manufactured by Ciba), 4, 4 ' -buty
  • polyphenols such as tetrakis [methylene-3- (3, 5-di-t- butyl-4-hydroxyphenyl ) propionate] methane (manufactured by Ciba Speciality Chemicals Inc: Irganox L 110), 1,1,3- tris (2-methyl-4-hydroxy-5-t-butylphenyl) butane (manufactured by Yoshitomi Chemicals Inc: Yoshinox 930), 1, 3, 5-trimethyl-2, 4, 6-tris (3, 5-di-t-butyl-4- hydroxybenzyl) benzene (manufactured by Shell Japan Inc: Ionox 330), bis-[3,3'-bis-(4'-hydroxy-3'-t- butylphenyl ) butyric acid] glycol ester, 2- (3 ' , 5 ' -di-t- butyl-4-hydroxyphenyl ) methyl-4- ( 2 " , 4 " -di-t)
  • sulphur-based antioxidants there may be mentioned by way of example dialkyl sulphides such as didodecyl sulphide or dioctadecyl sulphide, thiodipropionic acid esters such as didodecyl thiodipropionate, dioctadecyl thiodipropionate, dimyristyl thiodipropionate, or dodecyl octadecyl thiodipropionate, or 2-mercapto benzoimidazole .
  • dialkyl sulphides such as didodecyl sulphide or dioctadecyl sulphide
  • thiodipropionic acid esters such as didodecyl thiodipropionate, dioctadecyl thiodipropionate, dimyristyl thiodipropionate, or dodecyl o
  • triaryl phosphites such as triphenyl phosphite, or tricresyl phosphite
  • trialkyl phosphites such as trioctadecyl phosphite, or tridecyl phosphite, or tridodecyl trithiophosphite .
  • indazole or indazole derivatives such as toluindazoles such as 4-alkyl- indazoles or 5-alkyl-indazoles, benzothiazole, or benzothiazole derivatives such as 2-mercapto benzothiazole derivatives (Chiyoda Chemicals Inc:
  • 2-(alkyl dithio) benzothiazoles such as 2-(hexyl dithio) benzothiazole, 2- (alky1 dithio) toluthiazoles such as 2-(octyl dithio) benzothiazole, 2- (hexyl dithio) toluthiazole, 2-(octyl dithio) toluthiazole, 2- (N, N-dialkyl dithiocarbamyl) benzothiazoles such as 2- (N,N-diethyl dithiocarbamyl) benzothiazole, 2- (N, N-dibutyl dithiocarbamyl) benzothiazole or 2- (N, N-dihexyl dithiocarbamyl) benzothiazole, or 2- (N, N-dialkyl dithiocarbamyl) toluthiazoles such as 2- (N, N-diethyl dithiocarbamyl) toluthiazoles, or 2- (
  • benzo-oxazole derivatives such as 2-(alkyl dithio) -benzo-oxazoles such as 2-(octyl dithio) benzo-oxazole, 2-(decyl dithio) benzo-oxazole, or 2-(dodecyl dithio) benzo-oxazole, or 2- (alkyl dithio) -toluoxazoles such as 2-(octyl dithio) toluoxazole, 2-(decyl dithio) toluoxazole, or 2-(dodecyl dithio) toluoxazole, thiadiazole derivatives such as 2,5- bis(alkyl dithio) -1, 3, 4-thiadiazoles such as 2,5- bis (pentyl dithio) -1, 3, 4-thiadiazole, 2, 5-bis (nonyl dithio) -1, 3, 4-thiadiazole, 2, 5-bis (didi
  • One, or a combination of more than one, of these metal deactivators may be employed in a range of 0.01 to 0.5 weight% with respect to 100 weight% of base oil.
  • a phosphorus compound may be added to the lubricating oil composition according to the present invention and further improvement in wear-resistance and extreme pressure performance may thereby be conferred.
  • suitable phosphorus compounds according to the present invention include: phosphoric acid esters, acid phosphoric acid esters, amine salts of acid phosphoric acid esters, phosphorous acid esters, phosphorothionates, zinc dithiophosphates, phosphorus-containing carboxylic acids, and phosphorus- containing carboxylic acid esters.
  • One, or a combination of more than one, of these phosphorus compounds may be employed in a range of 0.01 to 2 weight% with respect to 100 weight% of base oil.
  • Examples of the above phosphoric acid esters that may be given include: tributyl phosphate, tripentyl phosphate, trihexyl phosphate, triheptyl phosphate, trioctyl phosphate, trinonyl phosphate, tridecyl phosphate, triundecyl phosphate, tridodecyl phosphate, tritridecyl phosphate, tritetradecyl phosphate, tripentadecyl phosphate, trihexadecyl phosphate, triheptadecyl phosphate, trioctadecyl phosphate, trioleyl phosphate, or triphenyl phosphate, tris (isopropylphenyl) phosphate, triallyl phosphate, tricresyl phosphate, trixylenyl phosphate, cresyl diphenyl phosphate, or xylenyl diphenyl phosphate
  • acid phosphoric acid esters that may be given include: monobutyl acid phosphate, monopentyl acid phosphate, monohexyl acid phosphate, monoheptyl acid phosphate, mono-octyl acid phosphate, monononyl acid phosphate, monodecyl acid phosphate, monoundecyl acid phosphate, monododecyl acid phosphate, monotridecyl acid phosphate, monotetradecyl acid phosphate, monopentadecyl acid phosphate, monohexadecyl acid phosphate, monoheptadecyl acid phosphate, mono-octadecyl acid phosphate, mono-oleyl acid phosphate, dibutyl acid phosphate, dipentyl acid phosphate, dihexyl acid phosphate, diheptyl acid phosphate, dioctyl acid phosphate, dinonyl acid phosphat
  • amine salts of acid phosphoric acid esters there may be mentioned for example salts of the acidic phosphoric acid esters with amines such as methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, octylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, trimethylamine, triethylamine, tripropylamine, tributylamine, tripentylamine, trihexylamine, triheptylamine and trioctylamine .
  • amines such as methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, octylamine, dimethylamine, diethylamine, di
  • phosphorous acid esters there may be mentioned for example dibutyl phosphite, dipentyl phosphite, dihexyl phosphite, diheptyl phosphite, dioctyl phosphite, dinonyl phosphite, didecyl phosphite, diundecyl phosphite, didodecyl phosphite, dioleyl phosphite, diphenyl phosphite, dicresyl phosphite, tributyl phosphite, tripentyl phosphite, trihexyl phosphite, triheptyl phosphite, trioctyl phosphite, trinonyl phosphite, tridecyl phosphite, triundecyl phosphite, trid
  • phosphorothionates include tributyl phosphorothionate, tripentyl phosphorothionate, trihexyl phosphorothionate, triheptyl phosphorothionate, trioctyl phosphorothionate, trinonyl phosphorothionate, tridecyl phosphorothionate, triundecyl phosphorothionate, tridodecyl phosphorothionate, tritridecyl phosphorothionate, tritetradecyl phosphorothionate, tripentadecyl phosphorothionate, trihexadecyl phosphorothionate, triheptadecyl phosphorothionate, trioctadecyl phosphorothionate, trioleyl phosphorothionate, triphenyl phosphorothionate, tricresyl phosphorothionate, trixylenyl phospho
  • zinc dithiophosphates typically include zinc dialkyl dithiophosphates, zinc diaryl dithiophosphates, or zinc arylalkyl dithiophosphates.
  • zinc dialkyl dithiophosphates may be employed wherein the alkyl group of the zinc dialkyl dithiophosphate is a primary or secondary alkyl group of carbon number 3 to 22, or having an alkylaryl group substituted by an alkyl group of carbon number 3 to 18.
  • zinc dialkyl dithiophosphates that may be mentioned include zinc dipropyl dithiophosphate, zinc dibutyl dithiophosphate, zinc dipentyl dithiophosphate, zinc dihexyl dithiophosphate, zinc diisopentyl dithiophosphate, zinc diethylhexyl dithiophosphate, zinc dioctyl dithiophosphate, zinc dinonyl dithiophosphate, zinc didecyl dithiophosphate, zinc didodecyl dithiophosphate, zinc dipropylphenyl dithiophosphate, zinc dipentylphenyl dithiophosphate, zinc dipropylmethylphenyl dithiophosphate, zinc dinonylphenyl dithiophosphate, zinc didodecylphenyl dithiophosphate, or zinc didodecylphenyl dithiophosphate.
  • phosphorus-containing carboxylic acids or phosphorus-containing carboxylic acid compounds such as esters thereof, so long as these contain both a carboxylic group and a phosphorus atom in the same molecule, there is no particular restriction as to their structure; however, from the point of view of extreme pressure performance and heat/oxidation stability, phosphorylated carboxylic acids or phosphorylated carboxylic acid esters are preferable.
  • phosphorylated carboxylic acids and phosphorylated carboxylic acid esters compounds represented by for example the following formula (6) may be mentioned by way of example.
  • R4 and R5 may be the same or different and respectively indicate a hydrogen atom or hydrocarbon group of carbon number 1 to 30, R6 indicates an alkylene group of carbon number 1 to 20, R7 indicates a hydrogen atom or a hydrocarbon group of carbon number 1 to 30, Xl, X2, X3 and X4 may be the same or different, and respectively indicate an oxygen atom or a sulphur atom.
  • hydrocarbon groups of carbon number 1 to 30 in R4 and R5 in the above general formula (6) examples that may be given include alkyl groups, alkenyl groups, aryl groups, alkylaryl groups or arylalkyl groups.
  • useful ⁇ -dithio phosphorylated propanoic acids have the structure of the following general formula (7) .
  • ⁇ -dithiophosphorylated propanoic acid examples include 3-(di- isobutoxy-thiophosphorylsulfanyl) -2-methyl-propanoic acid.
  • phosphorus-containing carboxylic acid compounds in the present lubricating oil composition, but this content is preferably 0.001 to 1 weight%, more preferably 0.002 to 0.5 weight% with respect to 100 weight% of base oil.
  • the content of compounds in which R7 is a hydrogen atom is 0.001 to 0.1 weight%, preferably more 0.002 to 0.08 weight%, more preferably 0.003 to 0.07 weight%, even more preferably 0.004 to 0.06 weight%, and yet more preferably 0.005 to 0.05 weight%.
  • Polyhydric alcohol fatty acid esters may be blended with the lubricating oil composition according to the present invention with the object of improving oiliness.
  • esters of saturated or unsaturated fatty acids of carbon number 1 to 24 of polyhydric alcohols such as glycerol, sorbitol, alkylene glycols, neopentyl glycol, trimethylol propane, pentaerythritol or xylitol may be employed.
  • glycerol esters there may be mentioned by way of example glycerol monolaurate, glycerol monostearate, glycerol monopalmitate, glycerol mono-oleate, glycerol dilaurate, glycerol distearate, glycerol dipalmitate or glycerol dioleate .
  • sorbitol esters there may be mentioned by way of example sorbitol monolaurate, sorbitol monopalmitate, sorbitol monostearate, sorbitol monooleate, sorbitol dilaurate, sorbitol dipalmitate, sorbitol distearate, sorbitol dioleate, sorbitol tristearate, sorbitol trilaurate, sorbitol trioleate, or sorbitol tetraoleate.
  • alkylene glycol esters there may be mentioned by way of example ethylene glycol monolaurate, ethylene glycol monostearate, ethylene glycol mono-oleate, ethylene glycol dilaurate, ethylene glycol distearate, ethylene glycol dioleate, propylene glycol monolaurate, propylene glycol monostearate, propylene glycol mono- oleate, propylene glycol dilaurate, propylene glycol distearate or propylene glycol dioleate.
  • neopentyl glycol esters there may be mentioned by way of example neopentyl glycol monolaurate, neopentyl glycol monostearate, neopentyl glycol mono-oleate, neopentyl glycol dilaurate, neopentyl glycol distearate, or neopentyl glycol dioleate .
  • trimethylol propane esters there may be mentioned by way of example trimethylol propane monolaurate, trimethylol propane monostearate, trimethylol propane mono-oleate, trimethylol propane dilaurate, trimethylol propane distearate, trimethylol propane dioleate, or pentaerythritol monolaurate.
  • pentaerythritol esters there may be mentioned by way of example pentaerythritol monostearate, pentaerythritol mono-oleate, pentaerythritol dilaurate, pentaerythritol distearate, pentaerythritol dioleate, or pentaerythritol mono-oleate.
  • fatty acid esters of such polyhydric alcohols preferably partial esters of polyhydric alcohols and unsaturated fatty acids are employed.
  • pour- point depressants or viscosity index improving agents may be added.
  • viscosity index improving agents there may be mentioned by way of example non-dispersive viscosity index improving agents such as polymethacrylate or ethylene-propylene copolymer, styrene-diene copolymer, or olefin polymers such as poly-isobutylene, or polystyrene, or dispersive viscosity index improving agents obtained by copolymerization of a nitrogen-containing monomer with these. These may be employed in a range of 0.05 to
  • pour-point depressants there may be mentioned by way of example polymethacrylate-based polymers. These may be employed in a range of 0.01 to 5 weight% with respect to 100 weight% of base oil.
  • an anti-foaming agent may be added.
  • anti- foaming agents suitable in the present invention there may be mentioned by way of example organosilicates such as dimethyl polysiloxane, diethyl silicate, or fluorosilicones, or non-silicone anti-foaming agents such as polyalkylacrylates . These may be employed either alone or in a combination of two or more thereof, in a range of 0.0001 to 0.1 weight% with respect to 100 weight% of base oil.
  • anti-emulsifiers suitable in the present invention there may be mentioned by way of example known anti-emulsifiers that are employed as ordinary lubricating oil additives. These may be employed in a range of 0.005 to 0.5 weight% with respect to 100 weight% of base oil . Practical Examples
  • Base oil 1 paraffin-based mineral oil obtained by application in suitable combination of purifying means such as hydrocracking and dewaxing to a lubricating oil fraction obtained by distillation of crude oil at normal pressure, classified in Group II (Gp II) in the API (American Petroleum Institute) base oil classification.
  • Base oil 2 paraffin-based mineral oil obtained by application in suitable combination of purifying means such as hydrocracking and dewaxing to a lubricating oil fraction obtained by distillation of crude oil at normal pressure, classified in Group III (Gp III) in the API (American Petroleum Institute) base oil classification.
  • Gp III Group III
  • API American Petroleum Institute
  • Base oil 3 this is a GTL base oil synthesised using the Fischer-Tropsch method: classified as Group III in the API (American Petroleum Institute) base oil classification.
  • Base oil 4 poly- ⁇ -olefins (PAO) of synthetic oil, general name PAO6 classified as Group IV in the API (American Petroleum Institute) base oil classification.
  • PAO poly- ⁇ -olefins
  • API American Petroleum Institute
  • Base oil 5 paraffin-based mineral oil obtained by application in suitable combination of purifying means such as dewaxing to a lubricating oil fraction obtained by distillation of crude oil at normal pressure, classified in Group I (Gp I) in the API
  • additive A2 aspartic acid derivative: COLACOR93 manufactured by Colonial Chemicals Inc (acid value in accordance with the method of JIS K2501: 75 mg KOH/g) ; (2-3) Additive A3: aspartic acid derivative:
  • MONACOR39 manufactured by Unichema Inc (acid value in accordance with the method of JIS K2501: 60 mg KOH/g)
  • Additive B2 oleylamine: primary alkyl primary amine compound (base value in accordance with the method of JIS K2501: 215 mg KOH/g)
  • Additive B3 tallow amine (chief constituent: oleylamine, stearylamine, palmitylamine) : primary alkyl primary amine compounds (base value in accordance with the method of JIS K2501: 215 mg KOH/g)
  • Additive B4 primary amine of C18 tertiary alkyl group: tertiary alkyl primary amine compound (base value in accordance with the method of JIS K2501: 155 mg KOH/g)
  • Additive B5 coconut secondary amine (chief constituent didodecylamine ) : primary alkyl secondary amine compound (base value in accordance with the method of JIS K2501: 160 mg KOH/g)
  • Additive B6 coconut diamine (chief constituent N-dodecyl-1, 3-propylene diamine) (base value in accordance with the method of JIS K2501: 440 mg KOH/g) (2-10)
  • Additive B7 tallow diamine (chief constituents N-oleyl-1, 3-propylene diamine, N- stearylamine-1, 3-propylene diamine, N-palmityl-1, 3- propylene diamine) (base value in accordance with the method of JIS K2501: 330 mg KOH/g)
  • Additive B8 N-alkyl diethanolamines (chief constituent N-dodecyl dimethylamine) : tertiary amine compound (base value in accordance with the method of JIS K2501: 160 mg KOH/g)
  • Additive B9 N-alkyl diethanolamines (chief constituent N-oleyl diethanolamine) : tertiary amine compound (base value in accordance with the method of JIS K2501: 160 mg KOH/g)
  • the coefficient of friction was measured at 25 0 C by a Masuda type pendulum oil properties testing machine, manufactured by Shinko Zoki Inc. In this test, the sample oil is supplied to the friction location of the pendulum fulcrum, the pendulum is oscillated, and the coefficient of friction is found from the damping of the oscillations.
  • Examples 1 to 3 of Table 1 by use of an aspartic acid derivative and aliphatic amine with the base oil 1, anti-rust properties are provided that pass the anti-rust properties test, and the coefficient of friction can be lowered. Also, it can be seen that an aspartic acid derivative can be employed alone as shown in Examples 1 to 3, or a mixture thereof can be employed, as shown in Example 4. Furthermore, as shown in Example 5, good results are obtained even when a mixture of both an aspartic acid derivative and aliphatic amine is employed.
PCT/EP2008/051470 2007-02-07 2008-02-06 Lubricating oil composition WO2008095966A1 (en)

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WO2016096753A1 (en) * 2014-12-17 2016-06-23 Shell Internationale Research Maatschappij B.V. α-OLEFIN ADSORPTION INHIBITING LUBRICANT COMPOSITION, ADSORPTION INHIBITING METHOD AND ADSORPTION INHIBITOR
EP3037507A4 (en) * 2013-08-23 2017-02-08 Idemitsu Kosan Co., Ltd Lubricating oil composition for shock absorber
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JP6723097B2 (ja) * 2016-06-30 2020-07-15 日立オートモティブシステムズ株式会社 油圧装置用作動油およびその油圧装置用作動油を用いた油圧装置
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