US20090176670A1 - Biodegradable lubricating oil composition - Google Patents

Biodegradable lubricating oil composition Download PDF

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Publication number
US20090176670A1
US20090176670A1 US10/585,203 US58520305A US2009176670A1 US 20090176670 A1 US20090176670 A1 US 20090176670A1 US 58520305 A US58520305 A US 58520305A US 2009176670 A1 US2009176670 A1 US 2009176670A1
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lubricating oil
oil composition
mass
test
biodegradable lubricating
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US10/585,203
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English (en)
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Hiroshi Kawasaki
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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Publication of US20090176670A1 publication Critical patent/US20090176670A1/en
Assigned to IDEMITSU KOSAN CO., LTD. reassignment IDEMITSU KOSAN CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KAWASAKI, HIROSHI
Priority to US14/176,432 priority Critical patent/US20140155307A1/en
Abandoned legal-status Critical Current

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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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/44—Five-membered ring containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
    • C10M2207/0225—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • 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
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • 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
    • C10M2207/2895—Partial esters containing free hydroxy groups used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbasedsulfonic acid salts
    • 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
    • C10N2020/081—Biodegradable 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
    • C10N2030/02—Pour-point; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • 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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2030/64—Environmental friendly compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • 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

Definitions

  • the present invention relates to a biodegradable lubricating oil composition. More specifically, it relates to a synthetic ester-based biodegradable lubricating oil composition which has excellent biodegradability, a high viscosity index, a low pour point, a high flash point, being satisfactory with lubricity, oxidative stability, property of preventing the corrosion of iron and non-ferrous metals, and suitability for use with sealing materials.
  • Vegetable oils such as rapeseed oil, synthetic esters and polyalkyleneglycols have been used as a biodegradable base oil.
  • vegetable oils have a problem of thermal or oxidative instability as well as unstable supply despite low cost
  • polyalkyleneglycols have a problem of a poor suitability for use with sealing materials despite low cost and good thermal stability. Therefore, although synthetic esters are becoming more popular as biodegradable lubricating oils in Japan, they still have a substantial weakness against a mineral oil-based lubricating oil in terms of the cost and oxidative stability.
  • the biodegradability standard was changed from the partial biodegradation test, “CEC Test Guideline” (reference degree of biodegradability: 67% or more) to the inherent biodegradation test, “OECD Test Guideline 301C method” (reference degree of biodegradability: 60% or more), and (2) The acute toxicity test for Japanese medaka ( Oryzias latipes ), JIS K 0102 (reference: LC 50 ⁇ 100 mg/L) was added.
  • a lubricating oil composition comprising a polyol ester base oil composed of a carboxylic acid having 5 to 14 carbon atoms and a carboxylic acid having 15 to 38 carbon atoms in a weight ratio of 0.1:99.9 to 50:50, in which at least one of the compounds selected from the group consisting of a sulfonate, a condensate between an alkanolamine and a carboxylic acid having 5 to 14 carbon atoms and a polybutenyl succinimide is contained at 0.1 to 15 weight % (for example, Patent Document 1), a fire-resistant hydraulic fluid comprising a hydraulic base oil containing, as a main component, a polyol partial ester having a hydroxyl value of 35 mg KOH/g or more, a flash point of 290° C.
  • ester is composed of a polyol having 3 to 12 carbon atoms and 3 to 6 total hydroxyl groups and a linear-chain monocarboxylic acid having 6 to 22 carbon atoms (for example, Patent Document 2), a lubricating oil comprising a synthetic ester having a kinematic viscosity of 20 to 40 mm 2 /s at 40° C., a viscosity index of 120 or more and a pour point of ⁇ 30° C.
  • ester is composed of a dimethylol alkane wherein the alkane has 5 to 7 carbon atoms and a linear-chain fatty acid having 10 to 20 carbon atoms (for example, Patent Document 3), a non-aqueous hydraulic fluid comprising a base oil composed of trimethylolpropane trioleate or neopentylglycol dioleate and a surfactant such as polyoxyethylene alkyl ether (for example, Patent Document 4) and the like.
  • biodegradable lubricating oils are satisfactory with respect to lubricity and oxidative stability, they still have problems of a high pour point, substantial metal dissolution of non-ferrous metals used for materials for hydraulic machinery, extreme swelling of sealing materials, and so on.
  • Patent Document 1 JP Kokai 1993-339591
  • Patent Document 2 JP Kokai 1994-228579
  • Patent Document 3 JP Kokai 1997-249889
  • Patent Document 4 JP kokai 1999-323373
  • the present invention was completed under these circumstances with an object to provide a biodegradable lubricating oil composition which has excellent biodegradability, a high viscosity index, a low pour point, a high flash point, being satisfactory with lubricity, oxidative stability, property of preventing the corrosion of iron and non-ferrous metals, and suitability for use with sealing materials.
  • the present inventor studied intensively in order to develop a biodegradable lubricating oil composition which meets the aforementioned preferable properties, and found that a lubricating oil composition having a certain value or more of the biodegradability that is determined according to the OECD Test Guideline 301C method satisfies the purpose of the study, wherein the lubricating oil composition is composed of a synthetic ester base oil comprising mainly an ester composed of an aliphatic hindered polyol having a specific structure and an aliphatic monocarboxylic acid, to which a specific additive is admixed in a predetermined ratio.
  • the present invention has been accomplished based on the aforementioned findings. That is, the present invention provides:
  • R 1 and R 2 represent independently a hydrocarbon group having 1 to 6 carbon atoms or a methylol group, and n is an integer of 0 to 4
  • a synthetic ester-based biodegradable lubricating oil composition which has excellent biodegradability, a high viscosity index, a low pour point, a high flash point, being satisfactory with lubricity, oxidative stability, property of preventing the corrosion of iron and non-ferrous metals, and suitability for use with sealing materials.
  • the biodegradable lubricating oil composition of the present invention comprises; (A) a synthetic ester base oil and (B) ingredients comprising a combination of (a) a phenolic antioxidant, (b) calcium sulfonate having a low base number and (c) a triazole compound.
  • the synthetic ester base oil used as component (A) of the present invention comprises at least 50 mass % hindered ester of an aliphatic monocarboxylic acid with an aliphatic hindered polyol which has one or more quaternary carbon atoms per molecule and in which at least one of the quaternary carbon atoms has one to four methylol groups bonded thereto.
  • the aliphatic hindered polyol which has one or more quaternary carbon atoms per molecule and in which at least one of the quaternary carbon atoms has one to four methylol groups bonded thereto of the present invention (which may be referred to simply as the hindered polyol hereinafter) is preferably a compound represented by general formula (I):
  • R 1 and R 2 independently represent a hydrocarbon group having 1 to 6 carbon atoms or a methylol group, and n is an integer of 0 to 4.
  • hydrocarbon group having 1 to 6 carbon atoms among R 1 and R 2 in general formula (I) a linear or branched alkyl or alkenyl group is preferable, and especially, an alkyl group is preferable.
  • hindered polyols refers to a hindered polyol such as neopentyl glycol, trimethylolalkane (the alkane has 2 to 7 carbon atoms) and pentaerythritol or a dehydrated condensate thereof.
  • neopentyl glycol 2-ethyl-2-methyl-1,3-propanediol; 2,2-diethyl-1,3-propanediol; trimethylolethane; trimethylolpropane; trimethylolbutane; trimethylolpentane; trimethylolhexane; trimethylolheptane; pentaerythritol; 2,2,6,6-tetramethyl-4-oxa-1,7-heptanediol; 2,2,6,6,10,10-hexamethyl-4,8-dioxa-1,1′-undecanediol; 2,2,6,6,10,10,14,14-octamethyl-4,8,12-trioxa-1,15-pentadecanediol; 2,6-dihydroxymethyl-2,6-dimethyl-4-oxa-1,7-heptanediol; 2,6,10-trihydroxymethyl-2,
  • the hindered polyols may be used singly or as a mixture of 2 or more thereof in the esterification.
  • a preferable number of n is 0 to 2.
  • Preferred hindered polyols are trimethylolpropane, neopentyl glycol, pentaerythritol and dehydrated condensates thereof, wherein preferable dehydrated condensates are bimolecular or trimolecular condensates.
  • the above-described hindered polyols can be synthesized according to the conventional method.
  • the dehydrated condensates of the hindered polyols can be synthesized by dehydration condensation of the hindered polyols in the presence of a catalyst at about 180° C. by heating the hindered polyols at a temperature above the melting point and dispersing them in a solvent.
  • aliphatic monocarboxylic acids used in the esterification of the aliphatic hindered polyols mentioned above saturated or unsaturated monocarboxylic acids having 6 to 22 carbon atoms are used preferably.
  • the acyl group of the monocarboxylic acids may be linear or branched.
  • aliphatic monocarboxylic acids examples include linear saturated monocarboxylic acids such as caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, nonadecanoic acid, arachic acid and behenic acid, linear unsaturated monocarboxylic acids such as undecenoic acid, oleic acid, elaidic acid, cetoleic acid, erucic acid, brassidic acid, linoleic acid and linolenic acid, branched saturated monocarboxylic acids such as isomyristic acid, isopalmitic acid, isostearic acid, 2,2-dimethylbutanoic acid, 2,2-dimethylpentanoic acid, 2,2-dimethyloctanoic acid
  • the hindered ester synthesized by esterification reaction of the above-mentioned hindered polyol with the aliphatic monocarboxylic acid may be a fully-esterified or partially-esterified compound.
  • a preferable hindered ester is the fully-esterified compound.
  • the hindered esters may be used singly or as a mixture of two or more thereof in the biodegradable lubricating oil composition of the present invention. Further, the amount of the hindered ester in the synthetic ester base oil is 50 mass % or more, preferably 70 mass % or more, and furthermore preferably 80 mass % or more in order to satisfy the predetermined properties of the biodegradable lubricating oil composition described below.
  • an ester base oil which can be used together with the hindered ester there may be cited an ester composed of an aliphatic polyol other than the hindered polyol mentioned above and the above-described monocarboxylic acid from the viewpoint of biodegradability, etc. of the lubricating oil composition.
  • Kinematic viscosity of the synthetic ester base oil used as the component (A) in the lubricating oil composition depends on the purpose of use of the lubricating oil composition, and is approximately in the range from 10 to 200 mm 2 /s at 40° C. in general, preferably in the range from 10 to 100 mm 2 /s, and more preferably in the range from 15 to 80 mm 2 /s in the case of hydraulic fluid application.
  • An acid value of the synthetic ester base oil is preferably 3 mg KOH/g or less and particularly preferably 1 mg KOH/g or less in terms of prevention of corrosion of machinery. Further, there is no particular limitation for a hydroxyl value, but it is preferably 50 mg KOH/g or less and particularly preferably 20 mg KOH/g or less from a viewpoint of lubricity.
  • phenolic antioxidant as component (a) of the ingredient (B) is not particularly limited, and phenolic antioxidant known in the art can be used with suitable selection.
  • phenolic antioxidant include 4,4-methylenebis(2,6-di-t-butylphenol); 4,4′-bis(2,6-di-t-butylphenol); 4,4′-bis(2-methyl-6-t-butylphenol); 2,2′-methylenebis(4-ethyl-6-t-butylphenol); 2,2′-methylenebis(4-methyl-6-t-butylphenol); 4,4′-butylidenebis(3-methyl-6-t-butylphenol); 4,4′-isopropylidenebis(2,6-di-t-butylphenol); 2,2′-methylenebis(4-methyl-6-t-nonylphenol); 2,2′-isobutylidenebis(4,6-dimethylpenol); 2,2′-methylene
  • these phenolic antioxidants may be used singly or in a combination of two or more thereof.
  • the aforementioned hindered ester used for the synthetic ester base oil has satisfactory oxidative stability by itself, and the oxidative stability of the lubricating oil composition can further be improved by admixing such a phenolic antioxidant, which also results in the increase in thermal stability.
  • the amount of the phenolic antioxidant added is in the range from 0.1 to 5.0 mass % based on the total amount of the present composition. When the amount of the phenolic antioxidant is in the range mentioned above, the effect of improvement in the oxidative stability is exhibited and the balance between cost and effectiveness becomes excellent.
  • the preferable amount of the phenolic antioxidant admixed is in the range from 0.5 to 3.0 mass %.
  • the phenolic antioxidants are used in the present invention from a viewpoint of impact on ecosystems.
  • the low base number calcium sulfonate as the component (b) in the ingredient (B) is added to give anti-rust effect to the lubricating oil composition and has also detergency and dispersion function.
  • the calcium sulfonate is a calcium salt of a sulfonated alkyl-substituted aromatic compound.
  • the calcium sulfonate having a low base number such that the total base number (TBN) is in the range from 0 to 100 mg KOH/g (preferably in the range from 0 to 50 mg KOH/g) is used in the present invention.
  • the low base number calcium sulfonates may be used singly or in a combination of two or more thereof.
  • the amount of the calcium sulfonate added is in the range from 0.01 to 2.0 mass % based on the total amount of the composition.
  • the amount of the low base number calcium sulfonate is preferably in the range from 0.05 to 1.0 mass %.
  • the triazole compound as (c) component in the ingredient (B) is added as a metal deactivator and is used to give corrosion-prevention effect for non-ferrous metals to the lubricating oil composition.
  • the triazole compounds are benzotriazole and its derivatives.
  • the triazole compound may be used singly or in a combination of two or more kinds thereof.
  • the amount of the triazole compound admixed is in the range from 0.01 to 1.0 mass % based on the total amount of the composition. When the amount of the triazole compound is in the aforementioned range, satisfactory corrosion-prevention effect can be exhibited and excellent balance between cost and effectiveness is obtained.
  • the amount of the triazole compound admixed is preferably in the range from 0.05 to 0.5 mass %.
  • the base oil itself has a level of lubricity equivalent to that of a conventional mineral oil-based antiwear hydraulic fluid, and in order to further improve the lubricity, an extreme-pressure agent and/or an antiwear agent may be added.
  • sulfur-based or phosphorus-based extreme-pressure agents can be used.
  • the sulfur-based extreme-pressure agent are sulfurized fats and oils, sulfurized fatty acids, sulfurized esters, polysulfides, sulfurized olefins, thiocarbamates, thioterpenes, dialkylthiodipropionates and the like.
  • sulfurized fats and oils, polysulfides and sulfurized olefins are preferred.
  • Examples of the phosphorus-based extreme-pressure agent are phosphates, (mono-, di-, or tri-)thiophosphates, amine salts of acidic phosphates, amine salts of (mono-, or di-)thiophosphates, phosphites, (mono-, di-, or tri-)thiophosphites and the like.
  • examples of the antiwear agent are zinc dithiophosphate (ZnDTP), zinc dithiocarbamate (ZnDTC), sulfurized molybdenum dithiophosphate (MoDTP), sulfurized molybdenum dithiocarbamate (MoDTC), and the like.
  • the extreme-pressure agent or antiwear agent may be used singly or in a combination of two or more kinds thereof. Further, the total amount of these agents admixed is in the range from 0.1 to 5.0 mass % based on the total amount of the composition. When the amount of the extreme-pressure agent and/or antiwear agent is in the aforementioned range, improvement in the antiwear effect is exhibited and excellent balance between cost and effectiveness is obtained. The amount of the extreme-pressure agent and/or antiwear agent is preferably in the range from 0.5 to 3.0 mass %.
  • additives such as viscosity index improver, pour point depressant, ash-free dispersant, surfactant, anti-foaming agent, demulsifier and so on can be added in such a range of the amount that no drawback to the effect of the present invention is brought about.
  • the degree of biodegradation of the lubricating oil composition as determined by the microbial degradation test of chemical substances according to the OECD Test Guideline 301C method is 70% or more (the reference degree of biodegradability is 60% or more), and has excellent biodegradability. Further, the 96-h LC 50 value of the acute toxicity test for usually 100 mg/L or more, and has low impact on living organisms. Therefore, it can be said that the lubricating oil composition is a very environmentally friendly lubricating oil.
  • the viscosity index is usually 130 or more, preferably 140 or more
  • the pour point is ⁇ 40° C. or lower, preferably ⁇ 45° C. or lower
  • the flash point is usually 250° C. or higher, preferably 260° C. or higher.
  • the synthetic ester base oil of the aforementioned component (A) has a viscosity index of 130 or more by itself, so addition of a viscosity index improver to the present composition is usually not necessary.
  • the lubricating oil composition has such a low pour point as mentioned above so that machinery startability at lower temperatures is excellent with the present composition when it is used as a hydraulic fluid. Also, the present composition has such a high flash point as mentioned above so that it has high flame retardance and hence it belongs to the category of a safe combustible liquid having VG of 32 or more according to the Fire Service Law.
  • the biodegradable lubricating oil composition of the present invention has excellent biodegradability, low impact to ecosystems, a high viscosity index, a low pour point, a high flash point, being satisfactory with lubricity, oxidative stability, property of preventing the corrosion of non-ferrous metals, and suitability for use with sealing materials. It has thus an excellent balance of those different properties.
  • the lubricating oil composition is preferable, for example, as a hydraulic fluid that is a power transmission fluid used in power transmission, power control, shock absorption and the like in a hydraulic system such as hydraulic machinery or equipment, a lubricating oil for automobiles used in automatic transmission, buffer, driving machinery such as power steering, gears and the like, a metal-working oil for cutting, polishing or plasticizing, and the like.
  • the degree of biodegradation was determined according to the modified MITI test method, OECD301C. According to the authorized standard of “ECOMARK” revised in July, 1998, the degree of biodegradation is required to be 60% or more.
  • LC 50 half lethal concentration after 96 hours was determined according to JIS K 0102 test method using Japanese medaka ( Oryzias latipes ). According to the authorized standards of “ECOMARK” revised in July, 1988, the LC 50 value is required to be 100 mg/L or more.
  • the relative kinematic viscosity at 40° C. (kinematic viscosity after the test/kinematic viscosity before the test) was determined, wherein 300 mL of a sample oil filled in a cylinder (45 mm in diameter, 500 mm in length) was subjected to a test in the presence of copper and iron as a catalyst, under the conditions either at 130° C. for 48 hours or at 150° C. for 48 hours with air intake rate of 10 L/hour.
  • the relative kinematic viscosity at 40° C. was determined after a test sample was subjected to a test under the following conditions:
  • Air intake rate 1 NL/h
  • Catalyst Cu coil (1.6 mm in diameter, 60 m in length), and
  • the test duration to measure the time when either the relative kinematic viscosity the test duration to measure the time when either the relative kinematic viscosity reaches 1.1, or the acid value reaches 2.0 mg KOH/g, or the Millipore value reaches 10 mg/100 mL of the sample (wherein the Millipore value is defined as a weight of fine powdery residue obtained by filtering out the residue with 0.8 ⁇ m membrane filter by vacuum filtration, followed by washing with n-hexane and drying), from which the service life was determined.
  • Lubricating oil compositions with compositions shown in Tables 1-1 and 1-2 were prepared along with commercially-available products. General properties and biodegradability of these lubricating oil compositions are listed in Tables 2-1 and 2-2.
  • PET denotes pentaerythritol
  • TMP denotes trimethylolpropane
  • NPG denotes neopentyl glycol
  • ZnDTP denotes zinc dithiophosphate
  • POE denotes polyoxyethylene
  • Tables 3-1 and 3-2 indicate the test results of lubricity, oxidative stability and corrosion prevention of non-ferrous metals for each lubricating oil composition.
  • Table 4 indicates the test results of suitability for use with sealing materials of the lubricating oil composition of Example 1 and the lubricating oil compositions of Comparative examples 1 to 4.
  • the lubricating oil compositions of the present invention have a well-balanced properties such as excellent biodegradability, a high viscosity index, a low pour point, a high flash point, being satisfactory with lubricity, oxidative stability, property of preventing the corrosion of iron and non-ferrous metals, and suitability for use with sealing materials.
  • the biodegradable lubricating oil composition of the present invention comprises a synthetic ester base oil having excellent biodegradability, has well-balanced properties including lubricating performance, and is preferably used, for example, as a hydraulic fluid, automotive lubricating oil, metal-working oil, and so on.

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US8987177B2 (en) 2009-05-08 2015-03-24 Idemitsu Kosan Co., Ltd. Biodegradable lubricant composition
US9139795B2 (en) 2009-05-15 2015-09-22 Idemitsu Kosan Co., Ltd. Biodegradable lubricant composition
US20170218294A1 (en) * 2014-08-06 2017-08-03 The Lubrizol Corporation Industrial Gear Lubricant Additive Package with Biodegradable Sulfur Component
US20180044606A1 (en) * 2015-02-27 2018-02-15 Idemitsu Kosan Co., Ltd. Biodegradable lubricating oil composition
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JP2020059835A (ja) * 2018-10-04 2020-04-16 カングー カンパニー リミテッドＫｗａｎｇｗｏｏ Ｃｏ．， Ｌｔｄ． 環境にやさしく、低粘度であり、高引火性の非水溶性加工油
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