US20070042918A1 - Lubricating oil additive and lubricating oil composition - Google Patents

Lubricating oil additive and lubricating oil composition Download PDF

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Publication number
US20070042918A1
US20070042918A1 US10/574,843 US57484304A US2007042918A1 US 20070042918 A1 US20070042918 A1 US 20070042918A1 US 57484304 A US57484304 A US 57484304A US 2007042918 A1 US2007042918 A1 US 2007042918A1
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Prior art keywords
lubricating oil
additive
oil additive
mass
group
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US10/574,843
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English (en)
Inventor
Shinichi Yanagi
Hiroaki Koshima
Izumi Terada
Toshihiko Ichihashi
Nobuaki Watanabe
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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Publication of US20070042918A1 publication Critical patent/US20070042918A1/en
Assigned to IDEMITSU KOSAN CO., LTD. reassignment IDEMITSU KOSAN CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ICHIHASHI, TOSHIHIKO, KOSHIMA, HIROAKI, TERADA, IZUMI, WATANABE, NOBUAKI, YANAGI, SHINICHI
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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/123—Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds
    • 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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/085—Phosphorus oxides, acids or 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
    • 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
    • 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
    • C10M2207/287—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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • 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
    • 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
    • C10M2215/02—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
    • C10M2215/064—Di- and triaryl amines
    • 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
    • C10M2215/08—Amides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/049—Phosphite
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—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
    • C10N2040/045—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for continuous variable transmission [CVT]
    • 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
    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition

Definitions

  • the present invention relates to a lubricating oil additive and to a lubricating oil composition. More specifically, the present invention is directed to a lubricating oil additive which can afford a lubricating oil composition, such as an automatic transmission fluid or a continuously variable transmission fluid, having a particularly high wet friction material torque capacity and excellent ⁇ (friction coefficient)-V (sliding velocity) performances, and to a lubricating oil composition containing such a lubricating oil additive and having the above properties.
  • a lubricating oil composition such as an automatic transmission fluid or a continuously variable transmission fluid, having a particularly high wet friction material torque capacity and excellent ⁇ (friction coefficient)-V (sliding velocity) performances
  • the transmission is built in a torque converter.
  • Such a lock-up clutch has a function to transmit the driving power from an engine directly to the transmission according to the running conditions. By shifting between the torque converter drive and the direct drive at proper timings, the efficiency of the torque converter can be improved.
  • a metal-type detergent such as calcium sulfonate has been incorporated for the purpose of improving the transmission torque capacity.
  • a lubricating oil composition containing a bisimide and a monoimide having a hydrocarbyl group with 8 to 30 carbon atoms is disclosed (for example, see JP-A-2002-105478) as a composition exhibiting both high torque capacity of a wet clutch and good transmission performances while maintaining the shudder vibration preventing performance in a low speed range.
  • a lubricating oil composition containing a bisimide compound having a hydrocarbyl group with 8 to 30 carbon atoms and a boron-modified ashless dispersant is disclosed (for example, see JP-A-2001-288489) as a composition capable of maintaining shudder vibration preventing performance in a low speed range and of preventing delamination in the clutch.
  • the present invention has been made in the above situation and has as its object the provision of a lubricating oil additive which can afford a lubricating oil composition, such as an automatic transmission fluid or a continuously variable transmission fluid, having a particularly high wet friction material torque capacity and excellent ⁇ -V performances, and of a lubricating oil composition containing such a lubricating oil additive and having the above properties.
  • a lubricating oil additive which can afford a lubricating oil composition, such as an automatic transmission fluid or a continuously variable transmission fluid, having a particularly high wet friction material torque capacity and excellent ⁇ -V performances
  • the present inventors have made an intensive study to achieve the foregoing objects and, as a result, have found that a reaction product of a succinimide compound and a phosphorus atom-containing compound can serve as a lubricating oil additive meeting with the objects.
  • the present invention has been completed on the basis of such a finding.
  • the present invention provides:
  • a lubricating oil additive which can afford a lubricating oil composition, such as an automatic transmission fluid or a continuously variable transmission fluid, having a particularly high wet friction material torque capacity and excellent ⁇ -V performances, and a lubricating oil composition containing such a lubricating oil additive and having the above properties.
  • the lubricating oil additive of the present invention is a reaction product of (A) a succinimide compound and (B) a phosphorus atom-containing compound.
  • the succinimide compound used as the raw material (A) may be a boron-free succinimide compound or a boron-containing succinimide compound.
  • the boron-free succinimide compound may be, for example, a succinimide represented by the general formula (I): or by the general formula (II):
  • R 1 and R 3 each represent an alkyl group or an alkenyl group having 5 to 350 carbon atoms and R 4 represents hydrogen, or an alkyl group or an alkenyl group having 5 to 350 carbon atoms.
  • R 3 and R 4 may be the same with or different from each other.
  • R 2 , R 5 and R 6 each represent a divalent organic group and R 5 and R 6 may be the same with or different from each other.
  • n is an integer of 1 to 10.
  • the above alkyl or alkenyl group is preferably a polyalkenyl group, particularly a polybutenyl group or a polyisobutenyl group.
  • the succinimide represented by the general formula (I) or (II) may be produced by reacting an alkenyl or alkyl succinic acid or alkenyl or alkyl succinic anhydride with a corresponding amine.
  • amine there may be mentioned, for example, ethylenediamine, propanediamine, butanediamine, N-methyl-1,3-propanediamine, N,N-dimethyl-1,3-propanediamine and a polyalkylenepolyamine such as diethylenetriamine, triethylenetetramine, aminoethylpiperazine or tetraethylenepentamine.
  • the boron-containing succinimide compound may be obtained by reacting the boron-free succinimide compound with a boron-containing compound generally at a temperature of 50 to 250° C., preferably 100 to 200° C.
  • boron-containing compound there may be used at least one compound selected from a boron oxide, a boron halide, boric acid, boric anhydride, a borate ester, etc.
  • the above-described succinimide compounds may be used singly or in combination with two or more thereof.
  • the phosphorus atom-containing compound used as the raw material (B) there may be mentioned, for example, a phosphorus sulfide, a phospho sulfurized hydrocarbon compound, a phosphate ester, a phosphite ester and a dithiophosphate ester.
  • the alkyl group or groups incorporated into the phosphorus atom-containing compound may be linear or branched and may contain a cyclic structure. Further, an ether bond and/or a thioether bond may be also contained in the alkyl group or groups.
  • P 2 S 3 As the phosphorus sulfide, there may be mentioned P 2 S 3 , P 2 S 5 , P 4 S 7 and P 4 S 10 . Above all, P 2 S 5 is preferred.
  • phospho sulfurized hydrocarbon compound there may be used various compounds.
  • Phospho sulfurized hydrocarbon compounds having a structure in which two alkyl groups are bonded to a phosphorus atom are preferable.
  • Such compounds may include reaction products of an olefin and a phosphorus sulfide.
  • a phospho sulfurized hydrocarbon compound may be obtainable by using propylene, butene, isobutylene, a polymer or copolymer thereof, decene, cetene, octadecene, a terpene (such as pinene), vinylnorbornene or camphene as an olefin and P 2 S 3 , P 2 S 5 , P 4 S 7 or P 4 S 10 as a phosphorus sulfide, and by reacting them at a temperature of about 100 to 300° C. under a stream of nitrogen gas.
  • the particularly preferred olefin is ⁇ -pinene and the preferred phosphorus sulfide is P 2 S 5 .
  • phosphate ester, phosphite ester and dithiophosphate ester be each a diester.
  • R 7 and R 8 each represent a hydrocarbyl group having 1 to 20 carbon atoms.
  • R 7 and R 8 may be a linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a linear or branched alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms.
  • alkyl group having 1 to 20 carbon atoms examples include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a 2-ethylhexyl group, a decyl group, a dodecyl group, a tetradecyl group, a hexadecyl group, an octadecyl group and an eicosyl group.
  • Examples of the cycloalkyl group having 3 to 20 carbon atoms include a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group and a cyclooctyl group.
  • alkenyl group having 2 to 20 carbon atoms examples include an allyl group, a propenyl group, a butenyl group, an octenyl group, a decenyl group and an oleyl group.
  • Examples of the aryl group having 6 to 20 carbon atoms include a phenyl group, a tolyl group, a xylyl group and a naphthyl group.
  • Examples of the aralkyl group having 7 to 20 carbon atoms include a benzyl group, a phenethyl group and a naphthylmethyl group.
  • the hydrocarbyl group having 1 to 20 carbon atoms may be interrupted by one or more oxygen atoms and/or sulfur atoms.
  • the main chain may contain at least one ether bond or thioether bond or contain both ether and thioether bonds.
  • Examples of such a hydrocarbyl group include a hexyloxymethyl group, a hexyloxyethyl group, an octyloxymethyl group, an octyloxyethyl group, a dodecyloxymethyl group, a dodecyloxyethyl group, a hexadecyloxymethyl group, a hexadecyloxyethyl group, a hexylthiomethyl group, a hexylthioethyl group, an octylthiomethyl group, an octylthioethyl group, a dodecylthiomethyl group, a dodecylthioethyl group, a hexadecylthiomethyl group and a hexadecylthioethyl group.
  • acidic phosphate ester represented by the general formula (III) there may be mentioned, for example, dihexyl phosphate, dioctyl phosphate, di(2-ethylhexyl) phosphate, didodecyl phosphate, dihexadecyl phosphate, di(hexylthioethyl) phosphate, di(octylthioethyl) phosphate, di(dodecylthioethyl) phosphate, di(hexadecylthioethyl) phosphate, dioctenyl phosphate, dioleyl phosphate, dicyclohexyl phosphate, diphenyl phosphate, ditolyl phosphate, dibenzyl phosphate and diphenethyl phosphate.
  • dihexyl phosphate dioctyl phosphate
  • di(2-ethylhexyl) phosphate did
  • an acidic phosphite ester represented by the general formula (IV): wherein R 7 and R 8 are as defined above.
  • acidic phosphite ester represented by the general formula (IV) there may be mentioned, for example, dihexyl hydrogen phosphite, dioctyl hydrogen phosphite, di(2-ethylhexyl) hydrogen phosphite, didodecyl hydrogen phosphite, dihexadecyl hydrogen phosphite, di(hexylthioethyl) hydrogen phosphite, di(octylthioethyl) hydrogen phosphite, di(dodecylthioethyl) hydrogen phosphite, di(hexadecylthioethyl) hydrogen phosphite, dioctenyl hydrogen phosphite, dioleyl hydrogen phosphite, dicyclohexyl hydrogen phosphite, diphenyl hydrogen phosphite, ditolyl hydrogen pho
  • dithiophosphate ester As the preferred dithiophosphate ester, there may be mentioned a dithiophosphate ester represented by the general formula (V): wherein R 7 and R 8 are as defined above.
  • dithiophosphate ester represented by the general formula (V) there may be mentioned, for example, dihexyl dithiophosphate, dioctyl dithiophosphate, di(2-ethylhexyl) dithiophosphate, didodecyl dithiophosphate, dihexadecyl dithiophosphate, di(hexylthioethyl) dithiophosphate, di(octylthioethyl) dithiophosphate, di(dodecylthioethyl) dithiophosphate, di(hexadecylthioethyl) dithiophosphate, dioctenyl dithiophosphate, dioleyl dithiophosphate, dicyclohexyl dithiophosphate, diphenyl dithiophosphate, ditolyl dithiophosphate, dibenzyl dithiophosphate and diphenethyl dithiophosphate.
  • the above-described phosphorus atom-containing compounds may be used singly or in combination with two or more thereof.
  • the lubricating oil additive of the present invention is a reaction product obtained by reacting the above-described raw material (A) with raw material (B) in a molar ratio of preferably 1:10 to 10:1, more preferably 1:3 to 3:1.
  • a lubricating oil additive having the desired performance may be obtained.
  • the reaction may be carried out at a temperature of generally about 50 to 250° C., preferably 100 to 200° C.
  • an organic solvent such as a hydrocarbon compound may be used, if necessary.
  • the lubricating oil additive of the present invention thus obtained can afford a lubricating oil composition, such as an automatic transmission fluid or a continuously variable transmission fluid, having a particularly high wet friction material torque capacity and excellent ⁇ -V performances.
  • the lubricating oil composition of the present invention comprises a mineral oil and/or a synthetic base oil, and the above-described lubricating oil additive.
  • the content of the lubricating oil additive in the lubricating oil composition is preferably 0.01 to 50% by mass, more preferably 0.1 to 20% by mass, from the standpoint of capability of effectively showing the above effects.
  • both mineral oil and synthetic oil may be used.
  • mineral oil any of various conventionally known mineral oils may be used and there may be mentioned, for example, a paraffinic mineral oil, an intermediate mineral oil and a naphthenic mineral oil.
  • specific examples of the mineral oil include solvent-refined or hydrogen-refined light neutral oil, medium neutral oil, heavy neutral oil or bright stock and the like.
  • any of various conventionally known synthetic oils may be used and there may be used, for example, poly( ⁇ -olefin) (including a copolymer of ⁇ -olefin), polybutene, a polyol ester, an ester of a dibasic acid, a phosphate ester, a polyphenyl ether, an alkylbenzene, an alkylnaphthalene, a polyoxyalkylene glycol, neopentyl glycol, silicone oil, trimethylol propane, pentaerythritol and, further, a hindered ester.
  • poly( ⁇ -olefin) including a copolymer of ⁇ -olefin
  • polybutene e.g., polybutene, a polyol ester, an ester of a dibasic acid, a phosphate ester, a polyphenyl ether, an alkylbenzene, an alkylnaphthalene, a
  • base oils may be used singly or in combination of two or more thereof.
  • a mineral oil and a synthetic oil may be also used in combination.
  • the base oil have a kinematic viscosity at 100° C. of 1 to 30 mm 2 /s and % C A of 20% or less.
  • the kinematic viscosity is in the above range, it is possible to sufficiently reduce the friction in a sliding part, such as a gear bearing or a clutch, of an automatic transmission. Additionally, the low-temperature characteristics are good.
  • the kinematic viscosity at 100° C. is more preferably 2 to 20 mm 2 /s, particularly preferably 3 to 10 mm 2 /s.
  • the % C A is 20% or less, the low-temperature characteristics are good.
  • the % C A is particularly preferably 10% or less.
  • additives other than the lubricating oil additive of the present invention may be incorporated, singly or in combination of a plurality thereof, into the lubricating oil composition of the present invention for the purpose of further improving the performance thereof.
  • Representatives of such additives include an ashless dispersant, a metallic detergent, a friction modifier, a viscosity index improver, an extreme pressure additive, a corrosion inhibitor, an antifoaming agent and a colorant.
  • the lubricating oil additive of the present invention would not hinder the effects of such other additives.
  • the lubricating oil composition of the present invention thus formulated is suited as an automatic transmission fluid or a continuously variable transmission fluid having a high wet friction material torque capacity and excellent ⁇ -V performances and may be also used as a lubricating oil for construction or agricultural machines equipped with a transmission having a wet clutch or a wet brake, manual transmissions, motorcycle gasoline engines, diesel engines, gas engines and shock absorbers.
  • Designated as ⁇ 1 is a friction coefficient at 1 rpm, while as ⁇ 50 is a friction coefficient at 50 rpm.
  • Friction material commercially available cellulose wet paper material and steel plate
  • a lubricating oil additive (b) was prepared in the same manner as that described in Example 1-(1) except that di(2-ethylhexyl) hydrogen phosphite was substituted for dioleyl hydrogen phosphite in Example 1-(1).
  • a lubricating oil additive (c) was prepared in the same manner as that described in Example 1-(1) except that di(octylthioethyl) hydrogen phosphite was substituted for dioleyl hydrogen phosphite in Example 1-(1).
  • a lubricating oil composition containing 90.0% by mass of the mineral oil and 10.0% by mass of the lubricating oil additive (c) obtained in (1) above was prepared, so that the content of nitrogen derived from the lubricating oil additive (c) was 1,500 ppm by mass.
  • the performance of the composition was evaluated. The results are shown in Table 1.
  • a lubricating oil additive (d) was prepared in the same manner as that described in Example 1-(1) except that a phosphorus compound represented by the following formula was substituted for dioleyl hydrogen phosphite in Example 1-(1).
  • a lubricating oil additive (f) was prepared in the same manner as that described in Example 5-(1) except that di(2-ethylhexyl) dithiophosphate was substituted for phospho sulfurized pinene in Example 5-(1).
  • a lubricating oil composition containing 91.2% by mass of the mineral oil and 8.8% by mass of the lubricating oil additive (g) obtained in (1) above was prepared, so that the content of nitrogen derived from the lubricating oil additive (g) was 1,500 ppm by mass.
  • the performance of the composition was evaluated. The results are shown in Table 1.
  • a lubricating oil additive (h) was prepared in the same manner as that described in Example 5-(1) except that borated succinimide (boron content: 0.6% by mass) was substituted for borated succinimide (boron content: 0.4% by mass) in Example 5-(1).
  • a lubricating oil composition containing 92.5% by mass of the mineral oil and 7.5% by mass of the lubricating oil additive (h) obtained in (1) above was prepared, so that the content of nitrogen derived from the lubricating oil additive (h) was 1,500 ppm by mass.
  • the performance of the composition was evaluated. The results are shown in Table 1.
  • a lubricating oil additive (j) which was a reaction product of borated succinimide and diphosphorus pentasulfide.
  • a lubricating oil composition containing 92.5% by mass of the mineral oil and 7.5% by mass of the lubricating oil additive (j) obtained in (1) above was prepared, so that the content of nitrogen derived from the lubricating oil additive (j) was 1,500 ppm by mass.
  • the performance of the composition was evaluated. The results are shown in Table 1.
  • a lubricating oil additive (k) was prepared in the same manner as that described in Example 10-(1) except that borated succinimide (boron content: 0.6% by mass) was substituted for borated succinimide (boron content: 1.0% by mass) in Example 10-(1).
  • lubricating oil compositions having the formulations shown in Table 3 were prepared, so that the content of nitrogen derived from the additive (1) was 1,500 ppm by mass. The performance of each of the compositions was evaluated. The results are shown in Table 3.
  • the lubricating oil compositions of Examples 1 to 11 containing the lubricating oil additive of the present invention can maintain the transmission torque capacity at a high level and show a ⁇ ratio ( ⁇ 50/ ⁇ 1) of greater than 1.
  • Automatic transmission fluid compositions which contained lubricating oil additives (the reaction products of borated succinimide and phospho sulfurized pinene, giving the highest ⁇ d value in Examples 1 to 11) and which were compounded with various additives shown in Table 4 (polymethacrylate, calcium sulfonate, isostearamide and oleyl glyceride; numerals are % by mass) were prepared and evaluated for the purpose of confirming the performance as automatic transmission fluid compositions.
  • lubricating oil additives the reaction products of borated succinimide and phospho sulfurized pinene, giving the highest ⁇ d value in Examples 1 to 11
  • additives shown in Table 4 polymethacrylate, calcium sulfonate, isostearamide and oleyl glyceride; numerals are % by mass
  • the automatic transmission fluid compositions were further compounded with 1.1% by mass of a mixture containing 30% by mass of a phenol antioxidant, 30% by mass of an amine antioxidant, 30% by mass of a sulfur antioxidant, 3% by mass of a thiadiazole copper inactivation agent and 10% by mass of a silicone antifoaming agent.
  • the automatic transmission fluid compositions were each compounded with a mixture, as a base oil, containing 12.5% by mass of a mineral oil corresponding to 60 neutral and the balance of a mineral oil corresponding to 100 neutral.
  • a lubricating oil additive (n) was prepared in the same manner as that described in Example 13-(1) except that borated succinimide (boron content: 1.0% by mass) was substituted for borated succinimide (boron content: 0.6% by mass) in Example 13-(1).
  • the lubricating oil additive of the present invention can afford a lubricating oil composition, such as an automatic transmission fluid or a continuously variable transmission fluid, having a particularly high wet friction material torque capacity and excellent ⁇ -V performances.
  • the lubricating oil composition of the present invention containing the above lubricating oil additive is usable as an automatic transmission fluid or a continuously variable transmission fluid and as a lubricating oil for construction or agricultural machines equipped with a transmission having a wet clutch or a wet brake, manual transmissions, motorcycle gasoline engines, diesel engines, gas engines and shock absorbers.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
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WO2013147165A1 (ja) * 2012-03-29 2013-10-03 Ｊｘ日鉱日石エネルギー株式会社 コハク酸イミド化合物、潤滑油添加剤および潤滑油組成物
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