WO2008072740A1 - Additif pour huile et huile lubrifiante renfermant cet additif - Google Patents

Additif pour huile et huile lubrifiante renfermant cet additif Download PDF

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Publication number
WO2008072740A1
WO2008072740A1 PCT/JP2007/074158 JP2007074158W WO2008072740A1 WO 2008072740 A1 WO2008072740 A1 WO 2008072740A1 JP 2007074158 W JP2007074158 W JP 2007074158W WO 2008072740 A1 WO2008072740 A1 WO 2008072740A1
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Prior art keywords
carbon atoms
substituent
oil
additive
same
Prior art date
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PCT/JP2007/074158
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English (en)
Japanese (ja)
Inventor
Akira Hiyoshi
Shingo Nakayama
Nobuhito Amemiya
Shigeaki Kato
Toshihiro Inayama
Yukihiro Isogai
Ichiro Minami
Shigeyuki Mori
Original Assignee
Kyowa Hakko Chemical Co., Ltd.
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Priority claimed from JP2007123388A external-priority patent/JP2008169366A/ja
Application filed by Kyowa Hakko Chemical Co., Ltd. filed Critical Kyowa Hakko Chemical Co., Ltd.
Publication of WO2008072740A1 publication Critical patent/WO2008072740A1/fr

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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
    • 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
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
    • C10L1/2418—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides containing a carboxylic substituted; derivatives thereof, e.g. esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
    • C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • 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
    • C10M129/68—Esters
    • C10M129/72—Esters of polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/0206—Well-defined aliphatic 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • C10M2203/065—Well-defined aromatic 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
    • 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
    • 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
    • C10M2203/104—Aromatic fractions
    • C10M2203/1045—Aromatic fractions 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/003—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/17—Fisher Tropsch reaction products
    • C10M2205/173—Fisher Tropsch reaction products 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
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates 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
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/401—Fatty vegetable or animal oils 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
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
    • 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
    • C10M2215/20—Containing nitrogen-to-oxygen bonds
    • C10M2215/202—Containing nitrogen-to-oxygen bonds containing nitro 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
    • 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
    • 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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/003—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/02—Esters of silicic acids
    • C10M2227/025—Esters of silicic acids 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
    • 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
    • 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
    • C10M2229/025—Unspecified siloxanes; Silicones used as base material
    • 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
    • C10N2040/25—Internal-combustion engines

Definitions

  • the present invention relates to an additive for oils added to oils such as lubricating oil and fuel oil, and a lubricating oil containing the same.
  • lubricating oils especially automobile engine oils, are also strongly required to have fuel savings, long drains, etc., and at the same time, the upper limit concentration of metal, phosphorus and sulfur contained in the lubricating oil is limited. (See Non-Patent Documents 1 and 2). Therefore, there is a demand for lubricating oils that do not contain these components, particularly metals and phosphorus.
  • Lubricating oil is generally obtained by adding an additive to a lubricating base oil.
  • a lubricating base oil In order to improve the fuel efficiency of lubricating oils, it is said that it is effective to select a lubricating base oil with low viscosity and excellent heat resistance.
  • polar base oils such as esters are used. Is known (see Patent Document 1).
  • Patent Document 1 JP-A-2005-48192
  • Patent Document 2 Japanese Patent Publication No. 6-4867
  • Patent Document 3 Japanese Patent No. 2563295
  • Patent Document 4 Japanese Unexamined Patent Application Publication No. 2004-262964
  • Patent Document 5 Japanese Patent Publication No. 1 501319
  • Non-Patent Document 1 “Lubrication Economy”, 2005, July, p7
  • Non-Patent Document 2 "Monthly Trypology", 2005, December, p36
  • An object of the present invention is to provide an oil additive containing an ester that does not contain a metal component and a phosphorus component, and that contains an ester capable of imparting wear resistance to an oil such as a lubricating base oil. Another object is to provide a lubricating oil containing additives.
  • the present inventors have found that the above problems can be solved by using an ester into which a nitrogen atom has been introduced as an additive for oils, and have completed the present invention. That is, the present invention provides the following (1) to (; 16).
  • R 1 and R 2 are the same or different and each represents a hydrocarbyl which may contain one or more selected from the group consisting of an oxygen atom and a sulfur atom, and a and b are the same or Differently, it represents an integer of 0 to 5, X and Y are the same or different and each represents a sulfur atom or a single bond, W and Z are the same or different, a hydrogen atom, formula (II)
  • R 3 and R 4 are the same or different and represent a hydrogen atom, an optionally substituted hydrocarbyl, an optionally substituted hydrocarbylcarbonyl, or a substituent.
  • R 5 and R 6 are the same or different and represent a hydrogen atom, a hydrocarbyl optionally having substituent (s), a hydrocarbylcarbonyl optionally having substituent (s), Or R 5 and R 6 together with the adjacent carbon atom have a substituent! /, May ! / Form a cyclic hydrocarbyl ⁇ ,
  • n represents an integer of 1 to 10; R 7 and R 8 are the same or different and represent a hydrogen atom, an optionally substituted hydrocarbyl, and a substituent.
  • R 2 are the same or different and represent alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, or aryl having 4 to 20 carbon atoms. (1) to (4)! /, An additive for oils according to any one of the above.
  • (6) 1 ⁇ and R 2 are the same or different and each represents alkyl having 1 to 20 carbons or alkenyl having 2 to 20 carbons. Additives.
  • W and / or Z represents the formula (II), R 3 and R 4 forces are the same or different, a hydrogen atom, an optionally substituted alkyl having 1 to 20 carbon atoms, May have a substituent
  • alkenyl having 2 to 20 carbon atoms, having a substituent may be! /, Cycloalkyl having 3 to 20 carbon atoms, aryl having 4 to 20 carbon atoms which may have a substituent, It may have a substituent, aralkyl having 5 to 20 carbon atoms, having a substituent! /, May! /, An alkanol having 2 to 21 carbon atoms, having a substituent Alkenol of 3 to 21 carbon atoms, which may have a substituent! /, Aroyl of 5 to 21 carbon atoms, which has a substituent! /, May!
  • 5 to W and / or Z represents the formula (IV), R 7 and R 8 1S same or different, a hydrogen atom, a substituted An alkyl having 1 to 20 carbon atoms which may have a group, an alkenyl having 2 to 20 carbon atoms which may have a substituent, and an aryl having 4 to 20 carbon atoms which may have a substituent. Or R 7 and R 8 together with two adjacent carbon atoms, each having a substituent, may be! /, A cycloalkane having 3 to 20 carbon atoms, or The additive for oils according to any one of (1) to (6), which has a substituent and may form an aromatic ring having 4 to 20 carbon atoms.
  • W and / or Z represents the formula (II), R 3 and R 4 forces are the same or different, a hydrogen atom, an optionally substituted alkyl having 1 to 20 carbon atoms, May have a substituent
  • V alkenyl having 2 to 20 carbon atoms, having a substituent! /, May! /
  • Alkano having 2 to 21 carbon atoms May have a substituent, may have a C 5-21 aryl, or may have a substituent.
  • V alkylsulfonyl having 1 to 20 carbon atoms, or having a substituent! /, May! /, (1) to (6)! /, Representing arylarylsulfonyl having 4 to 20 carbon atoms Oil additive for crabs.
  • W and / or Z represents the formula (II), and R 3 and R 4 forces are the same or different and are a hydrogen atom or a hydrocarbylcarbonyl optionally having a substituent (1) to (The additive for oils as described in any one of 6).
  • W and / or Z represents the formula (IV), R 7 and R 8 are the same or different, and a hydrogen atom or an optionally substituted alkyl having 1 to 20 carbon atoms, a substituent A force representing alkenyl having 2 to 20 carbon atoms, or R 7 and R 8 together with two adjacent carbon atoms each having an alkyl substituent having 1 to 20 carbon atoms.
  • the additive for oils according to any one of (11).
  • W and / or Z represents the formula (III), and R 5 and R 6 are the same or different and are a hydrogen atom or a C 1-20 alkyl which may have a substituent. , May have a substituent, alkenyl having 2 to 20 carbon atoms, may have a substituent! /, May ! /, Aryl having 4 to 20 carbon atoms, or R 5 and R 6 may have a substituent attached to the adjacent carbon atom.
  • W and / or Z represents the formula (III), and R 5 and R 6 are the same or different and are a hydrogen atom or an optionally substituted carbon atom having 1 to 10 alkyls, substituted 2 to 10 carbon atoms that may have a group; 10 to alkenyl, or 4 to 4 carbon atoms that may have a substituent; Oil additive for crabs.
  • a lubricating oil comprising the additive for oils according to any one of (1) to (; 14) and a lubricating base oil.
  • Lubricating oil base oil is from mineral oil, vegetable oil, poly ⁇ -olefin, fatty acid ester, polyalkylene glycol, phosphate ester, silicone, silicate ester, polyphenyl ether, alkylbenzene, synthetic naphthene, gas-to-liquid.
  • an additive for oils containing an ester which does not contain a metal component and a phosphorus component and which can impart wear resistance properties to oils such as lubricating base oils, and the oil It is possible to provide a lubricating oil containing a general additive.
  • an ester represented by the formula (I) may be referred to as an ester (I).
  • the additive for oils of the present invention is added to oils such as lubricating base oils and fuel oils, and imparts wear resistance properties to these oils. Containing an ester represented by
  • the oils include, for example, engine oil, automatic transmission oil, continuously variable transmission oil, gear oil, power steering oil, shock absorber oil, turbine oil, hydraulic oil, refrigerating machine oil, rolling Oil, bearing oil, metal processing lubricant, sliding surface oil, grease, bio-lubricant, etc.
  • Hydrocarbyl in the definition of ester (I) is a monovalent group formed by removing one hydrogen atom from a hydrocarbon, which may have a substituent, may be saturated or not. It may be saturated, or may have a linear, branched, cyclic or cyclic structure. Hydrocarbyl having 1-30 carbon atoms is preferred, and having 1-20 carbon atoms is more preferred. More preferably, examples include alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, aryl and the like.
  • saturated hydrocarbyl examples include alkyl, cycloalkyl and the like.
  • Examples of the unsaturated hydrocarbyl include anolekenyl, anolequinyl, aryl, cycloalkenyl, aralkyl and the like.
  • linear hydrocarbyl for example, linear alkyl, linear alkenyl, A linear alkynyl is mentioned, A C1-C20 thing is more preferable.
  • branched hydrocarbyl include branched alkyl, branched alkenyl, and branched alkynyl.
  • cyclic hydrocarbyl examples include cycloalkyl, cycloalkenyl, aryl and the like.
  • hydrocarbyl having a ring structure examples include hydrogen atoms of alkyl or alkenyl, those substituted by a cyclic hydrocarbyl, and those having 4 to 20 carbon atoms are preferable. Specific examples thereof include phenylbenzyl, biphenylmethyl, naphthylmethyl, 2-phenylvinyl-1-yl and the like.
  • the hydrocarbyl may contain one or more of an oxygen atom and a sulfur atom.
  • Examples of the hydrocarbyl containing an oxygen atom include those containing an ether bond.
  • Examples of the hydrocarbyl containing a sulfur atom include those containing a disulfide bond, a sulfide bond, a polysulfide bond, and the like.
  • hydrocarbyl part of the hydrocarbyl carbonyl has the same meaning as the hydrocarbyl.
  • hydrocarbylcarbonyl those having 2 to 21 carbon atoms are preferable, for example, alkenol, alkenol, aroyl and the like.
  • hydrocarbyl part of hydrocarbyloxycarbonyl has the same meaning as the hydrocarbyl.
  • Hydrocarbyloxycarbonyl having 2 to 21 carbon atoms is preferred, for example, alkoxycarbonyl, cycloalkyloxycarbonyl, alkenyloxycarbonyl, aryloxycarbonyl, aralkyloxycarbonyl and the like. It is done.
  • hydrocarbyl moiety of hydrocarbylsulfonyl has the same meaning as the hydrocarbyl.
  • hydrocarbylsulfonyl those having 1 to 20 carbon atoms are preferable, for example, alkynolsulfonyl, alkenylsulfonyl, and allylsulfonyl.
  • Examples of the alkyl include linear or branched alkyl having 1 to 20 carbon atoms.
  • the linear alkyl having 1 to 20 carbon atoms is preferably, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, noel, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl.
  • Octadecyl Doro force S is mentioned. More preferably, methyl, octadecyl, etc. are mentioned.
  • Preferred examples of the branched alkyl having 3 to 20 carbon atoms include isobutyl, sec butyl, tert butynole and neopentyl.
  • alkenyl examples include force S such as linear or branched alkenyl having 2 to 20 carbon atoms.
  • As the straight chain alkenyl having 2 to 20 carbon atoms preferably, for example, vinyl, vinylol, 3-butene 1-yl, 2-butene 1-yl, 1-butene 1-yl, 4-pentene 1-yl, 3-pentene 1-yl, 2-pentene 1-yl, 1-pentene 1-yl, octadecenyl, oleyl, octadecadienyl. More preferred are octadecenyl, oleyl and the like, and even more preferred is force S such as oleyl.
  • Preferred examples of the branched alkenyl having 3 to 20 carbon atoms include isopropenyl and 2-methyl-1-propene-1-yl.
  • alkynyl examples include linear or branched alkynyl having 2 to 20 carbon atoms.
  • straight chain alkynyl having 2 to 20 carbon atoms examples include tetradecininole, hexadecynyl, and octadecynyl.
  • Preferred examples of the branched alkynyl having 4 to 20 carbon atoms include 3-methyl-1-butyne 1yl.
  • cycloalkanes having 3 to 20 carbon atoms include cyclohexanone, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclootatan, cyclononane, cyclodecane, cyclohexane. Pentadecane, cycloicosane, etc.
  • cycloalkyl having 3 to 20 carbon atoms include cyclopropynole, cyclof, chinole, cyclopentinole, cyclohexinole, cyclopentinole, cyclooctyl, cyclononyl. , Cyclodecyl, cyclopentadecyl, cycloicosyl and the like.
  • cycloalkenyl having 3 to 20 carbon atoms include cyclopropeninole, cyclopteninole, cyclopenteninole, cyclohexeninole, and cyclopente. Ninole, cyclootateninole, cyclononeninole, cyclodeceninole, cyclopentadecenole, cyclicosenyl and the like can be mentioned.
  • the alkyl part of the alkanoyl has the same meaning as the above alkyl.
  • alkanoyl those having 2 to 21 carbon atoms are preferred.
  • examples include tridecanol, tetradecanol, hexadecanol, octadecanol, and oleo oil. More preferably, acetyl
  • alkenyl part of the alkenol is as defined above.
  • alkenol those having 3 to 21 carbon atoms are preferable, for example, attaylroyl, methacroroyl, octadecenoyl, octadecadenoyl and the like.
  • aryl having 4 to 20 carbon atoms are phenyl, biphenyl, triphenyl, naphthyl, biranyl and the like.
  • the alkyl part of the aralkyl has the same meaning as the alkyl, and the aryl part has the same meaning as the aryl.
  • aralkyl those having 5 to 20 carbon atoms are preferred, and examples thereof include benzyl, phenethanol, 3-phenylpropyl, naphthylmethyl, biphenylmethyl and the like.
  • the reel part of the alloy is synonymous with the reel.
  • aroyl those having 5 to 21 carbon atoms are preferred, for example, benzoyl, naphthoyl, toluoyl, xyloyl and the like.
  • the cycloalkyl portion of the cycloalkyl carbonyl has the same meaning as the above cycloalkyl.
  • the cycloalkylcarbonyl is preferably one having 4 to 21 carbon atoms.
  • cyclopropinorecanoleponinore, cyclobutinorecano Examples include reponinore, cyclopentinorecanoleponinole, cyclohexylcarbonyl and the like.
  • alkyl moiety of alkoxycarbonyl has the same meaning as the above alkyl.
  • alkoxycarbonyl those having 2 to 21 carbon atoms are preferable, for example, methoxycanoleboninore, ethoxycanoleponinore, propinoreoxycanoleponinore, tert-butoxycanoleponi Nore (BOC).
  • the cycloalkyl part of the cycloalkyloxycarbonyl is the same as the above cycloalkyl.
  • cycloalkyloxycarbonyl examples include those having 4 to 21 carbon atoms, such as cyclopropinoreoxycanoleponinole, cyclopentinoreoxycanoleponinole, cyclohexyloxycarbonyl and the like.
  • alkenyl part of alkenyloxycarbonyl has the same meaning as the above alkenyl.
  • alkenyloxycarbonyl those having 3 to 21 carbon atoms are preferable, for example, alkoxycarbonyl and the like.
  • aryl portion of the aryl boron is synonymous with the aryl.
  • aryloxycarbonyl examples include those having 5 to 21 carbon atoms, preferably phenyloxycarbonyl, naphthyloxycarbonyl, biphenyloxycarbonyl and the like.
  • aralkyl portion of the aralkyloxycarbonyl is synonymous with the aralkyl.
  • aralkyloxycarbonyl those having 8 to 21 carbon atoms are preferable, for example, benzyloxycarbonyl, naphthylmethyloxycarbonyl and the like.
  • alkyl moiety of the alkylsulfonyl has the same meaning as the above alkyl.
  • alkylsulfonyl examples include those having 1 to 20 carbon atoms, preferably methanesulfonyl, ethanesulfonyl, and isopropylsulfonyl.
  • alkenyl part of alkenylsulfonyl is as defined above.
  • alkenylsulfonyl examples include those having 2 to 20 carbon atoms, preferably vinylsulfonyl and arylsulfonyl.
  • aryl moiety of arylsulfonyl is as defined above.
  • arylsulfonyl examples include those having 4 to 20 carbon atoms, preferably p-toluenesulfonyl and benzenesulfonyl.
  • aromatic hydrocarbons having 4 to 20 carbon atoms, preferably
  • nitrogen-containing heterocyclic group in addition to one nitrogen atom, for example, a nitrogen atom, an oxygen atom, and A 5- or 6-membered monocyclic heterocyclic group which may contain an atom selected from a sulfur atom and a bicyclic or tricyclic condensed 3- to 8-membered ring and selected from a nitrogen atom, an oxygen atom and a sulfur atom
  • examples include condensed heterocyclic groups that may contain atoms, and more specifically, aziridinyl, azetiduyl, pyrrolidinyl, piperidino, piperidinyl, azepanyl, 1, 2, 5, 6-tetrahydropyridyl, imidazolidinyl, pyrazolidinyl, Perajul, Homopiperadul, Birazolinyl, Oxazolidinyl, Morpholino, Thiazolidinyl, Thiomorpholino, 2H-Oxazolyl, 2H-thiazolyl
  • Having a substituent may be, a substituent of cycloalkylcarbonyl,
  • Each is the same or different and has 1 to 5 substitutions of hydroxyl, formyl, epoxy, force noreboxinore, menorecapto, amino, hydrazino, imino, azo, nitro, nitrinore, talented quix, Funoleo mouth and so on.
  • Each may be the same or different and may be substituted or substituted 1-5 alkyl, alkenyl, alkynole, hydroxyl, formyl, epoxy, carboxyl, mercapto, amino, hydrazino, imino, azo, nitro, nitrile, oxime, fluoro, etc. .
  • the alkynole, alkenyl, and alkynyl shown here are as defined above.
  • a benzene ring optionally having an alkyl substituent of 1 to 20 carbon atoms
  • alkyl having 1 to 20 carbon atoms examples include, for example, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, noel, and decyl, each having the same or different number. , Pentadecyl, icosyl, etc.
  • esters (I) as a more preferred example, a and b are simultaneously 1 or
  • esters (I 1 1) to esters (I 1 11) may be mentioned.
  • R represents a saturated or unsaturated hydrocarbyl having 1 to 10 carbon atoms, or an aryl having 4 to 10 carbon atoms.
  • MsOH represents methanesulfonic acid.
  • ester (I) described above can be used as an additive for oils or the like as it is, but it can also be used after being modified into a salt, for example.
  • salts examples include acid addition salts and amino acid addition salts.
  • Examples of acid addition salts include organic acid salts and inorganic acid salts.
  • Examples of the organic acid salt include carboxylate and sulfonate, and preferably, formate, acetate, trifluoroacetate, propionate, methanesulfonate, p-toluenesulfonate, and triflurate.
  • chloromethane sulfonate and more preferably methane sulfonate.
  • examples of inorganic acid salts include hydrochloride and hydrobromide
  • amino acid addition salts include lysine, glycine, phenylalanine, and aspartic acid.
  • the salt of the ester (I) has been obtained! /
  • the ester (I) can be purified as it is, or when it is obtained in the free form, the ester (I ) Is dissolved or suspended in a suitable solvent, and an acid or base is added to isolate and purify.
  • the ester (I) and its salt may exist in the form of an adduct with water or various solvents, and these adducts can also be used as the additive for oils of the present invention.
  • esters (I) may have stereoisomers such as geometrical isomers, optical isomers, tautomers, etc. In the present invention, all possible isomerisms including these are possible. Bodies and mixtures thereof can also be used as additives for oils.
  • the ester (I) can be produced by reacting a dibasic acid corresponding to this ester with an alcohol in the presence of a basic compound at 0-100 ° C using a condensing agent.
  • the corresponding dibasic acid is not limited as long as it corresponds to the ester (I), that is, R 1 and R 2 in the formula (I) are hydrogen atoms.
  • dibasic acid having an amino group examples include S-carboxymethylcysteine, lanthionine, cystine, homocystine, penicillamine disulfide and the like.
  • substituent of the amino group which may have a substituent include hydrocarbyl, hydrocarbylcarbonyl, hydrocarbyloxycarbonyl, hydrocarbylsulfonyl and the like.
  • Most of the dibasic acids can be produced according to the methods described in, for example, JP-A-62-48394 and JP-A-51-136619.
  • esters (I) those corresponding to the ester (I), that is, those consisting of R 1 or R 2 and hydroxyl (R 1 — OH or R 2 — OH) in the formula (I) are not limited. Absent. Many of these alcohols are commercially available, and can be produced according to the methods described in, for example, JP-A Nos. 2000-344695 and 2001-89403. .
  • Examples of the basic compound include amine compounds such as pyridine lutidine, 4-dimethylaminopyridine, and triethylamine.
  • Examples of the condensing agent include 1-ethyl-3- (N, N, -dimethylaminopropyl) carbopositimide, and calpositimide compounds such as N, N'-dicyclohexylcarbopositimide.
  • ester (I) for example, a dibasic acid and an alcohol corresponding to this ester are mixed in the presence of an acid catalyst such as methanesulfonic acid or p-toluenesulfonic acid.
  • an acid catalyst such as methanesulfonic acid or p-toluenesulfonic acid.
  • the method of making it react at ° C is also mentioned.
  • a method using hydrogen chloride, thionyl chloride, or the like as the catalyst can be used.
  • the introduction and removal of the protecting group from the active group can be carried out by a known method [for example, Protective Groups In Organic Synthesis, third edition, Green, ⁇ . W. Greene ) By John Wiley & Sons Inc. (1999).
  • Examples of the protecting group include benzyloxycarbonyl, pmethoxybenzyloxy canoleponinole, tert butoxycanoleponinole, 9 fluorenolemethoxycanoleponinole, 3-dinitro 2-pyridinesulfenyl, 2 —Bendioxycarbonyl halide, tert-butyl, benzyl, benzyl halide, tosyl, 4-methoxy 2, 3, 6 trimethylbenzenesulfonyl, 2, 2, 5, 7, 8 pentamethylchroman 6 sulfonyl, 2, 4 Dinitrophenyl, Tritinole, Benzyloxymethylenole, 4 Methylbenzyl, 4-Methoxybenzinole, Acetamidomethylenole, Honoreminole, Acetinole, 4, 4, Dimethoxybenzhydrinore, 2, 4, 6-Trimethoxybenzyl Can be mentioned.
  • the ester (I) described above can impart antiwear characteristics to oils such as lubricating base oils and fuel oils when used as an additive for oils. It can be used in place of friction modifiers (friction reducing agents, oil-based agents), wear reducing agents (extreme pressure agents, etc.). Further, depending on the case where the wear resistance can be imparted only by using the ester (I), these conventional products and the ester (I) may be used in combination.
  • esters (I) having different structures in the present invention may be used as a mixture.
  • the lubricating oil of the present invention comprises a lubricating base oil and an oil additive containing the ester (I) described above.
  • the content of the additive for oils in the lubricating oil is preferably 0.00;! To 300 mmol (millimono), more preferably 0.0;! To 200 mmol, and 0.; More preferably, lOOmmol. If it is within this range, the force S will give sufficient wear resistance.
  • the lubricating base oil for example, various lubricating base oils represented by natural base oil and synthetic base oil can be used. These may be either polar base oils or nonpolar base oils.
  • Examples of natural base oils include mineral oils, vegetable oils, and animal oils, and examples of mineral oils include, for example, paraffin-based crude oils, intermediate-based crude oils, and naphthenic-based crude oils. It is not limited.
  • a solvent refined oil obtained by treating a lubricating oil raw material derived by atmospheric pressure or vacuum distillation with an aromatic extraction solvent such as phenol or furfural, and hydrogen under severe cracking reaction conditions in the presence of a hydrocracking catalyst.
  • hydrotreating catalyst such as cobalt and molybdenum as silica-alumina support, the lubricating oil feedstock is treated with hydrogen under hydrotreating conditions.
  • Hydrotreated oil obtained by contact by a method using multiple stages of hydrotreating, by hydrotreating or solvent purification, followed by alkali distillation or sulfuric acid washing, or by hydrotreating after catalyst removal
  • the resulting highly refined oil can be preferably used.
  • vegetable oils include, but are not limited to, rapeseed oil, sunflower oil, soybean oil, olive oil, palm oil, and corn oil.
  • Synthetic base oils include polybutene, polypropylene, poly-olefins such as ⁇ -olefin oligomers having 8 to 14 carbon atoms; fatty acid monoesters, aromatic monoesters, fatty acid diesters, aromatic diesters, and aliphatic polyesters.
  • Esters such as basic acid esters, aromatic polybasic acid esters and polyol polyesters; polyalkylene glycols, phosphate esters, silicones, silicate esters, polyphenyl ethers, alkylbenzenes, synthetic naphthenes, gas-to-liquid (GTL), Forces that include fluorocarbons, ionic liquids, etc.
  • preferable lubricant base oils include solvent refined oil, hydrocracked oil, highly refined oil, vegetable oil, poly- ⁇ -olefin, fatty acid ester (fatty acid monoester, fatty acid diester, Basic acid esters), polyalkylene glycols, phosphate esters, silicones, silicate esters, polyphenyl ethers, alkylbenzenes, synthetic naphthenes, gas-to-liquids (GTUs), one or more of which may be used I like it.
  • solvent refined oil hydrocracked oil, highly refined oil, vegetable oil, poly- ⁇ -olefin, fatty acid ester (fatty acid monoester, fatty acid diester, Basic acid esters), polyalkylene glycols, phosphate esters, silicones, silicate esters, polyphenyl ethers, alkylbenzenes, synthetic naphthenes, gas-to-liquids (GTUs), one or more of which may be used I like it.
  • GTUs gas-to-liquids
  • the lubricating oil of the present invention includes the additive for oils containing the lubricating base oil and ester (I).
  • detergent dispersant, antioxidant, wear reducing agent (antiwear agent, anti-seizure agent, extreme pressure agent, etc.), friction modifier (friction reducing agent, oily agent), antifungal agent It may contain additives such as a phase inhibitor, a pour point depressant, a viscosity index improver, a thickener, an antiseptic, an antifoaming agent, a demulsifier, a dye, and a fragrance.
  • the addition amount of these additives can be set as appropriate, but is preferably contained in the lubricating oil from 0.00;
  • the cleaning dispersant is a dispersion action that stably disperses sludge in oil generated over time and suppresses the accumulation of these sludges; unstable intermediates such as water, organic acids, sludge precursors, etc. Solubilization of the varnish and sludge by solubilization; Lubricating base oil, organic acid produced by deterioration of additives, neutralization of sulfuric acid and corrosion of the base material and corrosion It is an additive mainly intended for acid neutralization and the like that suppresses causative wear.
  • Cleaning dispersants can be broadly divided into metal-based detergents that contain metals and ashless dispersants that do not contain metals.
  • Typical examples of the former are neutral / basic sulfonates and overbased ones.
  • This is a colloidal dispersion of metal hydroxides and carbonates in sulfonate, overbased phenate, overbased salicylate, phosphonate, overbased strength lupoxylate and the like.
  • the metal include calcium, magnesium, and sodium.
  • the ashless dispersant include monosuccinimide and bissuccinimide. As the detergent dispersant, one of these may be used alone, or two or more may be used in combination.
  • the antioxidant is an additive whose main purpose is to suppress degradation and decomposition caused by the reaction of the lubricating base oil or additive with oxygen in the air.
  • the mechanism of action is to stop the chain transfer reaction, decompose peroxides, and inactivate metal compounds that can serve as oxidation catalysts.
  • Those that act as chain terminators include phenolic and aromatic amine compounds.
  • substances that act as peroxide decomposing agents include sulfur-based and sulfur-phosphorus-based compounds.
  • the metal deactivator include compounds having the ability to form a complex with a metal such as benzotriazole. As the antioxidant, one of these may be used alone, or two or more may be used in combination.
  • a wear reducing agent is a frictional surface of friction generated by relative motion, and forms a film of an inorganic compound by chemically reacting with a metal or metal oxide forming the friction surface, thereby reducing wear and burning. It is an additive mainly intended to prevent sticking. Mainly intended to suppress wear Anti-seizure agents are mainly intended to prevent seizures, and anti-seize agents are primarily intended to prevent seizures, and those that are primarily intended to prevent seizures and suppress wear under severe conditions. Sometimes called pressure agents. Wear reducing agents are broadly classified into sulfur, phosphorus, chlorine, and organometallic, and sulfur compounds include olefin sulfide and sulfide. Typical examples include dibenzyl disulfide (DBDS). Can be mentioned.
  • DBDS dibenzyl disulfide
  • Phosphorous compounds include phosphites, phosphates, and amine phosphates, and typical examples include tricresyl phosphate (TCP).
  • Chlorinated compounds include chlorinated paraffins.
  • Typical examples of organometallic materials include zinc-dialkyldithiophosphate (ZnDTP), zincate (MoDTC), and molybdenum-dialkyldithiophosphate (MoDTP). As the wear reducing agent, one of these may be used alone, or two or more may be used in combination.
  • the additive for oils of the present invention containing ester (I) When the additive for oils of the present invention containing ester (I) is used, these sulfur-based, phosphorus-based, chlorine-based, and organometallic wear-reducing agents may be used in combination. If the additive for oils of the present invention is used, excellent wear reduction properties can be imparted to oils such as lubricating base oils without using these known wear reducing agents in combination. Therefore, for example, it is possible to prevent an increase in the concentration of metal or phosphorus in oils by using a phosphorus-based or organometallic wear-reducing agent in combination.
  • the friction modifier mainly reduces or increases friction by physical adsorption or chemical adsorption on the metal or metal oxide forming the friction surface in the friction surface of friction generated by relative motion.
  • the target additive Those whose main purpose is to reduce friction may be referred to as oiliness agents or friction reducing agents.
  • Friction modifiers can be broadly classified into ashless friction modifiers that do not contain metals, metal-based friction modifiers that contain metals, and solid lubricants. Ashless friction modifiers have a structure that has both a polar group that binds strongly to the metal surface in the molecule and a long-chain carbon chain.
  • Typical examples include stearic acid, oleic acid, stearylamine, oleyl alcohol, And oleylamine, oleylamide, glycerin monooleate (GMO) and the like.
  • metal friction modifiers include MoDTC and MoDTP.
  • solid lubricants include graphite and molybdenum disulfide. Friction As the preparation, one of these may be used alone, or two or more may be used in combination.
  • a friction modifier such as an ashless friction modifier, a metal friction modifier, or a solid lubricant is used in combination.
  • a friction modifier such as an ashless friction modifier, a metal friction modifier, or a solid lubricant is used in combination.
  • an excellent friction reducing property is imparted to oils such as lubricating base oils without using these known friction modifiers in combination. can do. Therefore, for example, it is possible to prevent an increase in the concentration of metals in oils by using a metal friction modifier in combination.
  • the antifungal agent is an additive whose main purpose is to prevent the base material from being distorted mainly due to oxygen and moisture present in the air.
  • Antifungal agents include alkyl succinic acid derivatives, metal soaps, esters, sulfonates, phosphites, amines and the like.
  • the pour point depressant is an additive whose main purpose is to further improve the low temperature fluidity by further lowering the wax pour point of the lubricating oil and further lower the minimum usable temperature of the lubricating oil.
  • Typical examples include polyalkyl metatalates, polyalkyl acrylates, polybutyl acetates, polyalkyl styrenes, polybutenes, condensates of chlorinated paraffins and naphthalene, condensates of chlorinated paraffins and phenols, and the like.
  • a viscosity index improver is an additive whose main purpose is to reduce the viscosity change due to the temperature of the lubricating oil by increasing the viscosity index, and to further expand the usable temperature range of the lubricating base oil.
  • Typical examples include polyalkylmetatalylate, polyisobutylene, polyalkylstyrene, ethylene-propylene copolymer, styrene-hydrogenated copolymer, styrene-maleic anhydride ester copolymer, and the like. These can be used alone or in combination.
  • Anti-foaming agents are the main causes of bubbling of lubricant base oil, oil shortage and increased compressibility resulting in machine malfunction due to wear and seizure, lubricant base oil overflow, oxidation deterioration It is an additive whose main purpose is prevention.
  • Typical examples include dimethylsiloxane, fluorosilicone, polyacrylate, perfluoroalkyl ether and the like.
  • Antifungal agents, pour point depressants, viscosity index improvers, antifoaming agents are V, among those exemplified for deviation
  • One type may be used alone, or two or more types may be used in combination.
  • the lubricating oil of the present invention includes, for example, engine oil, automatic transmission oil, continuously variable transmission oil, gear oil, power steering oil, shock absorber oil, turbine oil, hydraulic oil, refrigerating machine oil, rolling oil, bearing It can be used for various applications such as oil, lubricating oil for metal processing, sliding surface oil, grease, and biological lubricant.
  • Engine oil refers to automobiles, motorcycles, trains, ships, submersibles and other 4-cycle gasoline engines, 2-cycle gasoline engines, diesel engine piston ring and cylinder sliding parts, connecting rods and crankshaft bearings, cams Lubricant used to lubricate valve lifter valve systems and other parts.
  • Automatic transmission oil is lubricating oil used for power transmission, wear adjustment, and lubrication of various gears consisting of a fluid transmission, a gear unit, a wet clutch and a hydraulic mechanism that controls them. is there.
  • the continuously variable transmission oil is a lubricating oil used for a continuously variable transmission.
  • the belt drive type and the traction drive type, which are used as speed changers for automobiles, machine tools, and industrial machines.
  • a belt-driven continuously variable transmission consists of two pulleys on the engine side and drive wheel side and a belt hung between them.
  • Lubricating oil is used for lubrication and hydraulic operation of the belt, clutch plate, and hydraulic system.
  • Traction drive type continuously variable transmissions transmit torque between rolling elements through an oil film. Lubricating oil is used to transmit torque, prevent seizure of the rolling elements, and wear.
  • Gear oil is lubricating oil used for the purpose of lubricating gears and bearings, and is roughly classified into automobile gear oil and industrial gear oil.
  • Automobile gear oil is used to lubricate helical gears and hypoid gears used in manual transmissions, automatic transmission axles, and final reduction gears (diffs).
  • Industrial gear oil is used to lubricate helical gears, bevel gears, worm gears, etc. used in industrial machinery, including steel equipment, and gears in equipment.
  • the power steering oil is a lubricating oil used in the power steering device for the purpose of reducing the force applied to the steering wheel.
  • Shock absorber oil is used for the purpose of providing maneuverability, stability and ride comfort. It is a lubricating oil used for shock absorbers in pension equipment.
  • Turbine oil is lubricating oil used to lubricate turbine bearings and reduction gears, and is used in steam turbines, gas turbines, nuclear turbines, etc. for generators, ships and aircraft.
  • Hydraulic oil is lubricating oil used to lubricate the sliding parts of hydraulic equipment and devices, such as construction machinery, machine tools, metal and plastic processing machines, vehicles, ships and aircraft. Used for hydraulic equipment and devices.
  • Refrigerating machine oil is a lubricating oil that is used in the presence of coexistence with refrigerants in compressors of refrigerators, and is used in refrigerators for air conditioning, refrigerators, freezing and refrigeration for food processing and distribution, industrial use, etc. Used
  • the rolling oil is a lubricating oil used for the purpose of imparting lubricity to an excessive rubbing portion between the material and the roll when rolling a metal material such as steel or aluminum alloy.
  • Bearing oil is a lubricating oil that is the main lubrication object of bearings.
  • oil film bearings used for large sliding bearings of rolling mill roll necks.
  • oil is a lubricating oil used as a fluid bearing oil (dynamic pressure bearing oil) for bearings of precision machines such as spindle motors built into hard disk drives such as personal computers.
  • the metal working lubricant is a lubricant used for lubrication and cooling in metal machining, and includes cutting oil, rolling oil, press working oil, and drawing oil.
  • Sliding surface oil is used to impart friction characteristics to the stable surface of the table of various machine tools such as lathes and grinding machines where the sliding speed is very slow and no oil film is formed.
  • Lubricating oils include dedicated oils and hydraulic oils that serve both as stable surface lubrication and hydraulic fluids.
  • Grease is a semi-solid or solid dispersion of a thickening agent in lubricating oil.
  • wheel bearings constant velocity ball joints, universal joints, propeller shaft center supports, clutches Release bearings, water pump bearings, steering and accelerator linkage mechanisms, electrical equipment bearings, propeller shaft splines, instrument wire cables, wind regulators, body parts such as door mirrors, brake parts
  • body parts such as door mirrors, brake parts
  • brake parts For industrial use, rolling force, plain bearings, gears and Used in equipment with joints such as chains and machine sliding surfaces.
  • Biolubricants are lubricants used for artificial joints, artificial cartilage, and artificial tears-type eye drops, and materials that not only have lubricity and durability but also have no impact on the body are required.
  • the additive for oils containing ester (I) imparts wear resistance characteristics to the lubricating base oil even though it does not contain metal or phosphorus. You can. Therefore, it is very preferable in terms of the environment and the use of conventional additives containing heavy metal phosphorus such as zinc and molybdenum is restricted due to concerns about influence on the human body and contamination of lubricating oil. It is also very effective for various applications (work machines such as belt competitors used in food processing and pharmaceutical manufacturing, medical equipment, etc.).
  • the additive for oils containing ester (I) can reduce friction by adding to the lubricating base oil whether it is a polar base oil or a non-polar base oil. Wear resistance that combines wear resistance and wear resistance can be imparted. Therefore, conventionally, it is necessary to select and add both compatible friction modifiers and wear reducers (antiwear agents, anti-seizure agents, extreme pressure agents, etc.) according to the type of lubricant base oil. However, by adopting this oil additive, such complications can be eliminated.
  • oils of the present invention can be added to other oils such as fuel oils that use only the lubricating base oil.
  • Examples of the fuel oil include highly hydrorefined, for example, high performance turbine fuel oil. Fuel oil that is highly hydrorefined in this way tends to have a particularly insufficient lubrication performance, and fuel pumps using such fuel oil are subject to wear. Therefore, the addition of the additive for oils of the present invention is very effective.
  • the content of the additive for oils is in fuel derived 100 mass 0/0, 0. 00001 ⁇ ; 10 mass 0/0 Ca preferably ⁇ further (or 0.0000;! ⁇ 5 mass 0/0 good Furthermore, it is preferably 0.00000 ;! to 1% by mass, and within this range, sufficient wear resistance can be imparted.
  • the fuel oil may contain various additives in addition to the oil additives of the present invention.
  • the additive for oils of the present invention can be used as a solid lubricant as well as an additive to oils such as lubricating base oils and fuel oils.
  • solid lubricants can cause friction and wear on materials such as plastics and fibers, or on recording media, paints such as ink and film. It is added, coated or impregnated for the purpose of reducing.
  • sliding members such as plastic gears, bearings, and cams, thermal recording media, magnetic recording media, transfer media, lithographic printing plate precursors, image receiving sheets, and toners used in electrophotographic parts It can be used in various applications such as protective coating layers such as photoconductors and electrophotographic photoreceptors or cleaning members, optical fiber optical fiber drop cables, polarizers, protective coating layers such as endoscopes, and optical films.
  • N, N, monodi (tert-butoxycarbonyl) cystine (compound A) 18.5 g, 4 dimethylaminoviridine 10.3 g (Wako Pure Chemical Industries), and oleyl alcohol 22.6 g (Wako Pure Chemical Industries, Ltd.) methylene chloride Dissolve in lOOmL (manufactured by Wako Pure Chemical Industries, Ltd.) and stir well. Then add 1 ⁇ 7g of 1-ethyl-3— (N, ⁇ '-dimethylaminopropyl) carpositimide (manufactured by Aiby) for 3 hours at room temperature, then Heated and stirred at 40 ° C for 3 hours.
  • Prototype oil is prepared in the same manner as (1) above, and tested according to the method specified in (ASTM D4172) (load; 40 kgf, number of revolutions: 1200 rpm, time: 60 minutes, temperature: 75 ° C). The subsequent wear scar diameter was measured. A shell-type four-ball friction tester (manufactured by Takachiho Seiki) was used as the tester. The wear scar diameter was the average value of all three fixed spheres in the vertical and horizontal directions. The results are shown in Table 1.
  • N, N, monodi (tert-butoxycarbonyl) cystine (compound A) 18.5 g, 4 dimethylaminoviridine 10.3 g (manufactured by Wako Pure Chemical Industries, Ltd.), and n octyl alcohol 11.2 g (manufactured by Wako Pure Chemical Industries, Ltd.) are chlorinated After dissolving in methylene lOOmL (manufactured by Wako Pure Chemical Industries, Ltd.) and stirring well, add 1 ⁇ 9g of 1-ethinole — 3— (N, ⁇ '-dimethylaminopropyl) carpositimide (manufactured by Ibai), room temperature, then 40 ° Heat at C. Stir.
  • the reaction solution was cooled to room temperature and washed with 0.5 mol / L hydrochloric acid and distilled water.
  • the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C to obtain 26.2 g of N, N'-di (tert-butoxycarbonyl) cystinedioctyl (yield: 93.6%). It was.
  • the obtained N, N′-di (tertbutoxycarbonyl) cystinedioctyl 10 ⁇ Og was dissolved in methylene chloride and stirred until uniform.
  • Trifluoroacetic acid (manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto until the disappearance of the raw material was confirmed by thin layer chromatography (addition amount of trifluoroacetic acid: 32.0 g). After completion of the reaction, the reaction solution was washed with distilled water, saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain ester (I 2): 6.4 g (yield: 91.4%). The physical properties of this were as follows.
  • a trial oil was prepared in the same manner as in Example 1 except that the ester (I2) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 1.
  • Example 1 The same as Example 1 except that the ester (I3) thus obtained was used as an additive for oils. In this manner, a trial oil was prepared and evaluated in the same manner as in Example 1. However, only lubricating base oil A was used as the lubricating base oil. The results are shown in Table 1.
  • a trial oil was prepared in the same manner as in Example 1 except that the ester (I4) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. However, only lubricating base oil A was used as the lubricating base oil. The results are shown in Table 1.
  • N, N, monodi (tert-butoxycarbonyl) cystine (compound A) 18.5 g, 4 dimethylaminoviridine 10.3 g (manufactured by Wako Pure Chemical Industries), and stearyl alcohol 22.8 g (manufactured by Wako Pure Chemical Industries) 1-Ethyl-3- (N, ⁇ '-dimethylaminopropyl) carpositimide (Ibai) 17 ⁇ 7g was added, and the temperature was 3 hours at room temperature, then 40 ° C. And stirred for 3 hours. The reaction solution was cooled to room temperature and washed with 0.5 mol / L hydrochloric acid and distilled water.
  • N, N′-di (tert-butoxycarbonyl) cystine distearyl was obtained by dissolved in 150 mL of methylene chloride and stirred until uniform.
  • Trifluoroacetic acid manufactured by Wako Pure Chemical Industries, Ltd. was added thereto until the disappearance of the raw material was confirmed by thin layer chromatography (amount of trifluoroacetic acid: 40.2 g).
  • a trial oil was prepared in the same manner as in Example 1 except that the ester (I5) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 2.
  • N, N 'Di (tert-butoxycarbonyl) cystine (compound A) 4 ⁇ 4 g and 4-dimethylaminoamino lysine 2.4 g (manufactured by Wako Pure Chemical Industries, Ltd.) in methanol 1. Og (manufactured by Wako Pure Chemical Industries, Ltd.) and methyl chloride 25 mL After dissolving in (Wako Pure Chemical Industries, Ltd.) and stirring well, add 1-ethyl 3- (N, N'-dimethylaminopropyl) carpositimide (Ibai) 4.2g and then at room temperature for 2 hours, then Heated at 40 ° C for 3 hours and stirred.
  • 1-ethyl 3- (N, N'-dimethylaminopropyl) carpositimide (Ibai) 4.2g and then at room temperature for 2 hours, then Heated at 40 ° C for 3 hours and stirred.
  • N, N′-di (tert-butoxycarbonyl) cystine dimethyl (2.3 g) was dissolved in 30 mL of methyl chloride and stirred until uniform. Trifluoroacetic acid (manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto until thinning chromatography confirmed the disappearance of the raw material (amount of trifluoroacetic acid-added caroten: 5.7 g). After completion of the reaction, the reaction solution is distilled water, saturated aqueous sodium hydrogen carbonate solution, saturated food. Washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain cystine dimethyl: 0.6 g (yield: 25.8%).
  • a trial oil was prepared in the same manner as in Example 1 except that the ester (I6) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 2.
  • a trial oil was prepared in the same manner as in Example 1 except that the ester (I7) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 2.
  • a trial oil was prepared in the same manner as in Example 1 except that the ester (I11) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 3.
  • a trial oil was prepared in the same manner as in Example 1 except that the ester (8) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 4.
  • a trial oil was prepared in the same manner as in Example 1 except that the ester (9) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 4.
  • Suberic acid 5 Og (Wako Pure Chemical Industries), 4-dimethylaminopyridine 7.0 g (Wako Pure Chemical Industries), and alcohol alcohol 15.4 g (Wako Pure Chemical Industries) methylene chloride lOOmL (Wako Pure Chemical Industries, Ltd.) Medicinal product) 1-Ethyl-3- (N, N'-dimethylamino) propylcarbodiimide (manufactured by Aiby) (12 lg) was added, and the mixture was heated and stirred at room temperature and then at 40 ° C. The reaction solution was cooled to room temperature and washed with 0.5 mol / L hydrochloric acid, distilled water, saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain ester (10): 18. lg (yield: 93.2%). The physical properties of this were as follows.
  • a trial oil was prepared in the same manner as in Example 1 except that the ester (10) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 4.
  • a trial oil was prepared in the same manner as in Example 1 except that dibenzyldisulfide (DBDS) manufactured by Tokyo Chemical Industry was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 5.
  • DBDS dibenzyldisulfide
  • the additive for oils containing the ester of the present invention does not contain metal and phosphorus, and imparts wear resistance (friction reduction and wear reduction) to the oils. be able to. Therefore, according to the present invention, it is possible to provide oils such as lubricating oil and fuel oil having good wear resistance.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
  • Lubricants (AREA)

Abstract

Additif pour les huiles renfermant un ester de formule (I). Ledit additif est utilisé dans les huiles comme l'huile de graissage pour conférer, aux huiles, des propriétés de réduction des frottements et des propriétés de résistance à l'usure. R1 et R2 sont chacun un groupe hydrocarbyle, etc. ; a et b sont chacun un nombre entier de 0 à 5 ; X et Y sont chacun un atome de soufre ou une liaison simple ; et W et Z sont chacun un atome d'hydrogène, -NR3R4, etc. ; dans la mesure où W et Z ne sont pas tous les deux un atome d'hydrogène et que lorsque W ou Z est un atome d'hydrogène, alors X et Y ne sont pas tous les deux une liaison simple et R3 et R4 sont chacun un atome d'hydrogène, un groupe hydrocarbyle, etc.(I)
PCT/JP2007/074158 2006-12-14 2007-12-14 Additif pour huile et huile lubrifiante renfermant cet additif WO2008072740A1 (fr)

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JP2006337118 2006-12-14
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JP2007123388A JP2008169366A (ja) 2006-12-14 2007-05-08 油類用添加剤およびこれを含有する潤滑油

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009139433A1 (fr) * 2008-05-14 2009-11-19 協和発酵ケミカル株式会社 Additif pour huile et lubrifiant le contenant

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01501319A (ja) * 1986-11-07 1989-05-11 ザ　ルブリゾル　コーポレーション イオウ含有組成物，潤滑剤，燃料および機能流体組成物
JP2002322486A (ja) * 2001-04-27 2002-11-08 Sanyo Chem Ind Ltd 潤滑油用基油
JP2004262964A (ja) * 2003-02-05 2004-09-24 Idemitsu Kosan Co Ltd 潤滑油用及び燃料油用添加剤、並びに潤滑油組成物及び燃料油組成物
WO2005078054A1 (fr) * 2004-02-03 2005-08-25 Chemtura Corporation Compositions lubrifiantes comportant un melange antioxydant
JP2006045335A (ja) * 2004-08-04 2006-02-16 Idemitsu Kosan Co Ltd 潤滑油用及び燃料油用添加剤、並びに潤滑油組成物及び燃料油組成物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01501319A (ja) * 1986-11-07 1989-05-11 ザ　ルブリゾル　コーポレーション イオウ含有組成物，潤滑剤，燃料および機能流体組成物
JP2002322486A (ja) * 2001-04-27 2002-11-08 Sanyo Chem Ind Ltd 潤滑油用基油
JP2004262964A (ja) * 2003-02-05 2004-09-24 Idemitsu Kosan Co Ltd 潤滑油用及び燃料油用添加剤、並びに潤滑油組成物及び燃料油組成物
WO2005078054A1 (fr) * 2004-02-03 2005-08-25 Chemtura Corporation Compositions lubrifiantes comportant un melange antioxydant
JP2006045335A (ja) * 2004-08-04 2006-02-16 Idemitsu Kosan Co Ltd 潤滑油用及び燃料油用添加剤、並びに潤滑油組成物及び燃料油組成物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009139433A1 (fr) * 2008-05-14 2009-11-19 協和発酵ケミカル株式会社 Additif pour huile et lubrifiant le contenant

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