WO2005073351A1 - Additif pour huile lubrifiante et composition pour huile lubrifiante contenant celui-ci - Google Patents

Additif pour huile lubrifiante et composition pour huile lubrifiante contenant celui-ci Download PDF

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Publication number
WO2005073351A1
WO2005073351A1 PCT/JP2005/000913 JP2005000913W WO2005073351A1 WO 2005073351 A1 WO2005073351 A1 WO 2005073351A1 JP 2005000913 W JP2005000913 W JP 2005000913W WO 2005073351 A1 WO2005073351 A1 WO 2005073351A1
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acid
lubricating oil
oil
quaternary ammonium
group
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PCT/JP2005/000913
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English (en)
Japanese (ja)
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Naomi Koishikawa
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Adeka Corporation
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Application filed by Adeka Corporation filed Critical Adeka Corporation
Priority to EP05709314A priority Critical patent/EP1717298A4/fr
Priority to CA002552671A priority patent/CA2552671A1/fr
Priority to US10/587,020 priority patent/US20070155636A1/en
Publication of WO2005073351A1 publication Critical patent/WO2005073351A1/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
    • 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
    • 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
    • C10M133/16—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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • 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
    • C10M2207/26—Overbased carboxylic acid salts
    • C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
    • 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
    • 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
    • C10M2215/02—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
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    • 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
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated 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
    • 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
    • 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
    • C10M2215/28—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
    • C10M2219/046—Overbasedsulfonic acid 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
    • 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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04—Detergent property or dispersant property
    • 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
    • C10N2030/04—Detergent property or dispersant property
    • C10N2030/041—Soot induced viscosity control
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/52—Base number [TBN]
    • 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
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines

Definitions

  • the present invention relates to a lubricating oil additive and a lubricating oil composition containing the same.
  • metal-based detergents have been added to engine oil for the purpose of extending the life of the engine oil.
  • the metal-based detergent has a function of preventing sludge from accumulating inside the engine and a function of neutralizing acidic substances that are by-products of fuel combustion and deterioration of engine oil.
  • Overbased sulfonates, phenates, salicylates and the like are used in such metal detergents.
  • metal detergents such as overbased calcium sulfonate, calcium salicylate, and magnesium sulfonate are most commonly used because they are relatively inexpensive and have excellent cleaning performance.
  • the metal content in the metallic detergents causes various problems. Specifically, the metal released together with the exhaust gas adheres to the exhaust gas catalyst and reduces the exhaust gas purification performance. Also, in diesel engines, the particulate matter of the diesel particulate filter (DPF) is used. There is a problem that not only does the (PM) removal performance decrease, but it also hinders the reuse of DPF. For this reason, reducing the amount of metal syrup added by a metal detergent has become a major issue.
  • a lubricating oil composition containing an ashless dispersant and a phenol-based ashless antioxidant for example, see Patent Document 1
  • Patent Document 2 and 3 See, for example, Patent Literatures 2 and 3
  • Patent Document 4 lubricating oil compositions having a low total sulfated ash content containing an ashless dispersant, an oil-soluble antioxidant, and an oil-soluble dihydrocarbyl dithiophosphate have been proposed (for example, see Patent Document 4). ).
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2000-256690
  • Patent Document 2 Japanese Patent Application Laid-Open No. 9-100485
  • Patent Document 3 Japanese Patent Application Laid-Open No. 9-013067
  • Patent Document 4 Japanese Patent No. 2877887
  • the present invention has been made to solve the above-described problems, and does not contain a metal component such as calcium or magnesium, and has excellent cleaning performance, and a lubricating oil composition containing the same.
  • the present inventors diligently studied the above problem, and found that a quaternary ammonium salt having a specific base number and no metal content has a cleaning performance equal to or higher than that of a conventional metal-based detergent. And found that the present invention was completed.
  • the present invention is a lubricating oil additive comprising a quaternary ammonium salt having a base number of at least 10 mgK ⁇ H / g.
  • the present invention is also a lubricating oil composition containing the lubricating oil additive in an amount of 0.1 to 10% by mass based on the base oil.
  • metal refers to “typical metal element” and “transition metal element”. The invention's effect
  • a lubricating oil composition containing a quaternary ammonium salt having a base number of at least lOmgKOHZg and containing extremely small amounts of metals such as calcium and magnesium and having excellent cleaning performance is provided. can do.
  • the lubricating oil additive according to the present invention contains a quaternary ammonium salt having a base number of at least 10 mgK ⁇ H / g.
  • This quaternary ammonium salt may be used as it is as a lubricating oil additive, or may be used as a base oil or other additive used in a lubricating oil composition described later. And may be used as a lubricating oil additive mixed with.
  • the quaternary ammonium salt preferably has a high base number from the viewpoints of sludge dispersibility and acid neutralization.However, if the base number is too high, the friction coefficient of the lubricating oil may increase, or the base oil It is not preferable because the solubility in water may be deteriorated. For this reason, the base number of the quaternary ammonium salt is more preferably 30-600 mgKOHZg, more preferably 50-300 mgKOH / g.
  • the base number in the present invention is the number of milligrams (mg) of hydrochloric acid and an equivalent amount of potassium hydroxide required to neutralize the basic component contained in the quaternary ammonium salt lg, and J IS K2501 ( Petroleum products and lubricating oils-Neutralization number test method).
  • quaternary ammonium salt for example, a quaternary ammonium salt obtained by salt-exchanging a counterion contained in a cationic surfactant such as tetraalkylammonium chloride or tetraalkylammonium sulfate can be used. And quaternary ammonium salts. Among them, a quaternary ammonium salt represented by the following general formula (1) is preferable.
  • R 1 to R 4 each independently represent a hydrocarbon group having 1 to 30 carbon atoms, —R 90 —CO—R 10 or 1 R U NH—CO—R 12 ; At least one of 1 to R 4 is a hydrocarbon group having 1 to 30 carbon atoms, R 9 and R 11 are a hydrocarbon group having 1 to 4 carbon atoms, and R 1Q and R 12 are 1 to 1 carbon atoms. Represents a hydrocarbon group or a hydrogen atom of 30.
  • X— represents an anionic group.
  • Examples of the hydrocarbon group having 130 carbon atoms as R 1 —R 4 , R 1Q and R 12 include, for example, methinole, ethylenole, propyl, isopropyl, butyl, isobutyl, secondary butyl, tertiary Butyl, pentyl, isopentyl, secondary pentyl, neopentyl, tertiary pentyl, hexyl, secondary hexyl, heptyl, secondary heptyl, octyl, 2-ethylhexyl, secondary octyl, noninole, secondary nonyl, Decyl, secondary decyl, pendecyl, secondary condecyl, dodecyl, secondary dodecyl, tridecyl, isotridecyl, secondary tridecyl, tetradecyl,
  • X— represents an anionic group.
  • X— an anionic group, is an acid When expressed as an acidic compound HX, any compound having a value of pk (equilibrium constant), which is an index of acidity, greater than 0 may be used.
  • anionic groups include, for example, inorganic compounds such as carbonic acid, boric acid and citric acid; carbonic esters such as monomethyl carbonate and monoethyl carbonate; formic acid, acetic acid, propionic acid, butanoic acid (butyric acid), pentanoic acid ( Valeric acid), isopentanoic acid (isovaleric acid), hexanoic acid (caproic acid), heptanoic acid, isoheptanoic acid, octanoic acid (caprolic acid), 2-ethylhexanoic acid, isooctanoic acid, nonanoic acid (pelargone) Acid), isononanoic acid, decanoic acid (potassic acid), isodecanoic acid, pendecanoic acid, isopendecanoic acid, dodecanoic acid (lauric acid), isododecanoic acid, tridecanoic acid, isotridecanoic acid,
  • the quaternary ammonium salt represented by the general formula (1) of the present invention includes a tertiary amine compound, a tertiary amine amide compound, a tertiary amine ester compound and a tertiary amamide ester compound.
  • salt exchange may be performed by a known method.
  • the anionic group of the quaternary ammonium salt obtained by quaternization or salt exchange is a hydroxyl group
  • the hydroxyl group is neutralized with the above acidic compound HX, and the generated water is dehydrated to convert the hydroxyl group. It can be replaced with an anionic group derived from an organic carboxylic acid.
  • the tertiary amine compound as a starting material include, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, trihexynoleamine, triheptylamine, trioctylamine, trinonylamine, tridecinorea.
  • Amines triphenylamine, tritonolenoleamine, trixylinoleamine, tritamenoleamine, tribenzinoleamine, tristyrylamine, tricinnaminoleamine, tribenzhydrylamine, triethylphenylamine, Tripro Pyrphenamine, tributynolepheninoleamine, trihexylphenylamine, trioctylphenylamine, trinoylphenylamine, tridecylphenylamine, tridodecylphenylamine, tristyrenated phenylamine, Tri p-cuminorefeninoleamine, tribenzylphenylamine, triphenylnaphthinoleamine, trij3_naphthinoleamine, monomethyldiphenylamine, monomethylditolylamine, monomethyldixylylamine, monomethyldicumenylamine, monomethyamine Rudibenz
  • the tertiary amine amide compound as a starting material can be produced by the following method.
  • Triamines having two primary amine groups and one secondary amine group such as diethylenetriamine, dipropylenetriamine and ethylenepropylenetriamine; bis (3-aminopropyl) methinoleamine, bis (3-aminopropyl) ethylamine, bis (3-aminopropyl) ethylamine
  • Examples of the tertiary amine ester compound as a starting material include triethanolamine, N-methyljetanolamine, N-ethylethylanolamine, N-propyldiethanolamine, and N-isopropyldiethanolamine.
  • N-Butyl Jetanolamine N, N-Dimethylethanolamine, N, N-Diethylethanolamine, N, N-Dipropylethanolanolamine, N, N-Dibutylethanolamine, N— Tertiary such as cyclohexyl jetanolamine, N-benzyldiethanolamine, tripropanolamine, triisopropanolamine, N-cyclohexyldiisopropanolamine, N-benzyldiisopropanolamine, tributanolamine, etc. Alkanolamines.
  • a tertiary amine ester compound can also be obtained by reacting with a fatty acid, a fatty acid chloride or a fatty acid ester after esterification with a dani hydrocarbon or a dialkyl sulfate or the like to esterify the hydroxyl group of the amine compound.
  • the tertiary amido amide ester conjugate which is a starting material, can be produced by the following method. N-methanol ethylene diamine, N-ethanol ethylene diamine, N-propanol ethylene diamine, N-butanol ethylene diamine, N, ⁇ -dimethanol ethylene diamine, N, N-diethanol ethylene diamine, N, N-dipropanolethylenediamine, N, N-dibutanolethylenediamine, N-methanolpropylenediamine, N-ethanolpropylenediamine, N-propanolpropylenediamine, N-butanolpropylene Alkanol diamines such as diamine, N, N-dimethanol propylene diamine, N, N-diethanol propylene diamine, N, N-dipropanol propylene diamine, N, N-dibutanol propylene diamine; Alkanoldiamine by reacting with fatty acid,
  • an amide amide ester conjugate By subjecting the primary amine group and the hydroxyl group to an amidation and an esterification reaction, an amide amide ester conjugate can be obtained.
  • the obtained compound is a secondary amine amide ester conjugate
  • a tertiary amine amide ester compound is obtained by tertiary conversion of the secondary amine group with a halogenated hydrocarbon or dialkyl sulfate. Can be.
  • Fatty acids used for amidation of a primary amine group or amidation of a primary amine group with a hydroxyl group and esterification include, for example, formic acid, acetic acid, propionic acid, butanoic acid (butyric acid), and pentanoic acid Herbic acid), isopentanoic acid (isovaleric acid), hexanoic acid (caproic acid), heptanoic acid, isoheptanoic acid, octanoic acid (caprylic acid), 2-ethylhexanoic acid, isooctanoic acid, nonanoic acid (pelargonic acid) ), Isononanoic acid, decanoic acid (capric acid), isodecanoic acid, pendecane Acid, isopendecanoic acid, dodecanoic acid (lauric acid), isododecanoic acid, tridecanoic acid, isotridecanoic acid, tetrade
  • Natural fats and oils include, for example, linseed oil, eno oil, deer oil, olive oil, cacao butter, kapok oil, whitening lash oil, sesame oil, rice oil, safflower oil, cyanat oil, cinnamon oil, soybean oil Vegetable oils such as teaseed oil, camellia oil, corn oil, rapeseed oil, palm oil, palm kernel oil, castor oil, sunflower oil, cottonseed oil, coconut oil, wood wax, peanut oil, etc .; horse fat, tallow, beef tallow And animal fats such as beef tallow, lard, goat fat, sheep fat, milk fat, fish oil and whale oil.
  • quaternization reaction method As a quaternization reaction method, a known method can be used. Generally, after tertiary amine is charged into an autoclave, a quaternizing agent is added at 60 ° C to 200 ° C and ripened until the reaction is completed. In addition, in order to increase the reaction rate or the reaction rate, it may be pressurized with an inert gas such as nitrogen or helium.
  • the addition amount of the quaternizing agent is 1.0 to 4.0 monoles, preferably 1.1 to 2.5 monoles, and more preferably 1.1 to 1. mol. 8 monoles. If the added amount of the quaternizing agent is too small, the reaction will not be completed. If the added amount is too large, a large amount of unreacted quaternizing agent will remain and may be adversely affected on the environment, such as being released into the atmosphere.
  • the quaternizing agent used for quaternization includes, for example, organic halides such as methyl chloride, benzyl chloride, cyclohexyl chloride, methyl bromide, benzyl bromide and cyclohexyl bromide; Dialkyl sulfates such as dimethyl acid and getyl sulfate; dialkyl carbonates such as dimethyl carbonate and getyl carbonate; and trialkyl phosphates such as trimethyl phosphate and triethyl phosphate. Of these, use of methyl chloride or dimethyl carbonate is preferred from the viewpoint of easy availability of raw materials and handling.
  • a known method can be used without limitation.
  • a halogenated quaternary ammonium salt obtained by reacting a tertiary amine with an alkyl halide is subjected to an electrolysis method (Japanese Patent Publication No. 45-28564) and an ion exchange resin method (Japanese Patent Application Laid-Open No. 52-28564).
  • — 300 No. 9 a method of synthesizing a quaternary ammonium hydroxide and neutralizing the same with an acidic compound HX to remove generated water, and a method of removing a quaternary ammonium halide salt and sodium hydroxide.
  • a reaction with an inorganic alkali such as potassium hydroxide in a solvent to remove the generated inorganic salt, and neutralize the quaternary ammonium hydroxide obtained with the acidic compound HX.
  • organic solvent in a range that does not inhibit the reaction.
  • the organic solvent that can be used here is not particularly limited, and examples thereof include aliphatic, alicyclic, aromatic, and heterocyclic compounds or a mixture thereof, or a general lubricating oil.
  • alkane such as petroleum ether, methanol, ethanol, propanol, 2-propanol, butanol, 2-butanol, pentano, Alcohols such as hexanol, heptanol, octanol, and 2-ethylhexanol
  • alkyl ethers such as dimethyl ether, ethyl methyl ether, getyl ether, methyl isobutyl ether, and ethyl isopropyl ether
  • acetone, ethyl methyl ketone Ketones such as methyl isobutyl ketone, benzene, Aromatics such as ruene, xylene and ethylbenzene, poly- ⁇ -olefin, ethylene- ⁇ -olefin copolymer, polybuten
  • alkanes such as hexane, heptane, and petroleum ether, methanol, ethanol, monopropane, propanol, and 2-propanol, benzene, tonolen, xylen, and the like.
  • Preferred are aromatics, paraffinic mineral oils, naphthenic mineral oils, and the like. It is preferable to add these solvents in order to effectively remove by-products and impurities and to dissolve solid reaction products.
  • the lubricating oil composition according to the present invention contains the lubricating oil additive in an amount of 0.110% by mass, preferably 0.2-8% by mass, based on the base oil. Within this range, it is possible to improve the cleaning performance such as sludge dispersibility and acid neutralizing property without impairing the lubricity.
  • Examples of the base oil include mineral oil, hydrocarbon-based synthetic oil, and mixtures thereof that are commonly used as a base oil for lubricating oils. More specifically, poly-Ct-olefin, ethylene-co-olefin copolymer, polybutene, alkylbenzene, alkylnaphthalene, polyalkylene glycol, polyphenyl ether, alkyl-substituted diphenyl ether, polyol ester, dibasic acid ester And synthetic oils such as phosphate esters, phosphites, carbonates, silicone oils, fluorinated oils, paraffinic mineral oils, naphthenic mineral oils, and refined mineral oils obtained by refining these.
  • the lubricating oil composition of the present invention does not refuse the addition of known lubricating oil additives.
  • an antioxidant an organic molybdenum-based additive, an extreme pressure agent, Oiliness improvers, metal detergents, dispersants, viscosity index improvers, pour point depressants, corrosion inhibitors, corrosion inhibitors, defoamers, etc. may be added.
  • antioxidants examples include zinc dithiophosphate antioxidant IJ, phenolic antioxidant, and amine antioxidant.
  • the preferred content of these antioxidants is 0.1 to 5% by mass based on the base oil.
  • organic molybdenum-based additive examples include, for example, oxymolybdenum dithiocarbamate, oxymolybdenum dithiophosphate, fatty acid molybdenum salt, oxymolybdenum sulfide xanthate, and reaction of molybdenum trioxide with an acid phosphate.
  • reaction product reaction product of molybdenum trioxide and fatty acid diethanolamide, reaction product of molybdenum trioxide and glycerin monofatty acid ester, succinimide, carboxylic acid amide, Mannich base, or the reaction of molybdenum trioxide with molybdenum trioxide Reaction products, such as reaction products of an amine with a molybdenum compound having a pentavalent or hexavalent molybdenum atom, and the like.
  • the preferred compounding amount of these organic molybdenum-based additives is 0.001 to 5% by mass based on the base oil.
  • the extreme pressure agent examples include sulfur compounds such as sulfurized fats and oils, olefin polysulfide, dibenzyl sulfide and the like; monooctyl phosphate, tributyl phosphate, triphenyl phosphite, and tributyl phosphite. Compounds such as thiophosphoric acid and thiophosphoric acid esters; organometallic compounds such as thiophosphoric acid metal salts, thiocarbamic acid metal salts and acidic phosphoric acid ester metal salts And the like. The preferable blending amount of these extreme pressure agents is 0.1 to 10% by mass based on the base oil.
  • oiliness improver examples include higher alcohols such as oleyl alcohol and stearyl alcohol; fatty acids such as oleic acid and stearic acid; oleyl glycerin ester, laurinoleglycerin ester, oleyl sorbitan ester, oleyl trimethylol Esters such as propaneester; amides such as laurylamide, oleinoleamide, and stearylamide; amines such as laurinoleamine, oleylamine, and stearylamine; and ethers such as laurylglycerin ether and oleylglycerin ether.
  • the preferred blending amount of these oiliness improvers is 0.110% by mass with respect to the base oil.
  • the metal-based detergent examples include sulfonates such as calcium, magnesium, and barium, phenates, salicylates, phosphonates, and overbased salts thereof.
  • the amount of these metallic detergents is preferably small from the viewpoint of reducing the environmental load.
  • 0 to 10% by mass based on the base oil 0 to 5% by mass.
  • Examples of the dispersant include succinimide, benzylamine, succinate, and boron-modified products thereof.
  • the preferred compounding amount of these dispersants is 0.5 to 10% by mass based on the base oil.
  • viscosity index improver examples include poly (C118) alkyl methacrylate, (C118) alkyl acrylate / (C118) alkyl methacrylate copolymer, getylaminoethyl methacrylate Tallylate / (C118) alkyl methacrylate copolymer, ethylene / (C118) alkyl methacrylate copolymer, polyisobutylene, polyalkylstyrene, ethylene / propylene copolymer, styrene Z maleic acid
  • examples include an ester copolymer, a styrene / maleic acid amide copolymer, a hydrogenated styrene Z-butadiene copolymer, a hydrogenated styrene / isoprene copolymer, and the like.
  • the average molecular weight is about 10,000 1,500,000.
  • the preferred compounding amount of these viscosity index improvers is
  • pour point depressant examples include polyalkyl methacrylate, polyalkyl atalylate, polyalkyl styrene, and polybutyl acetate. Average molecular weight 1000 It is about 100,000. The blending amount of the pour point depressant is 0. 005- 3 mass 0/0 with respect to the base oil.
  • Examples of the protective agent include sodium nitrite, calcium oxide paraffin wax, magnesium oxide paraffin wax, alkali metal salt of tallow fatty acid, alkaline earth metal salt or amine salt, alkenyl succinic acid and alkenyl succinic acid.
  • Examples thereof include a half ester (the molecular weight of an alkenyl group is about 100 to 300), sorbitan monoester, pentaerythritol monoester, nourphenol ethoxylate, lanolin fatty acid ester, and lanolin fatty acid calcium salt.
  • the preferred blending amount of these protective agents is 0.01 to 5% by mass based on the base oil.
  • corrosion inhibitor examples include benzotriazole, benzimidazole, benzothiazole, tetraalkylthiuram disulfide, and the like.
  • the preferred compounding amount of these corrosion inhibitors is 0.013% by mass based on the base oil.
  • antifoaming agent examples include polydimethyl silicone, trifluoropropyl methyl silicone, colloidal silica, polyalkyl atalylate, polyanolequinolemethallate, alcohol ethoxy / propoxylate, and fatty acid ethoxy / propoxylate. And a sorbitan moiety fatty acid ester.
  • the preferred blending amount of these defoamers is 0.001 to 1% by mass based on the base oil.
  • the lubricating oil composition of the present invention includes a lubricating oil for an internal combustion engine, a lubricating oil for a drive system (such as a manual transmission oil, a differential gear oil, an automatic transmission oil, etc.), a lubricating oil for metal application, and a constant velocity joint.
  • Grease for automobiles including industrial grease, and industrial use grease. Among them, it can be suitably used as a lubricating oil for internal combustion engines such as gasoline engines, diesel engines, and jet engines.
  • a lubricating oil for internal combustion engines such as gasoline engines, diesel engines, and jet engines.
  • a reference oil having the following composition was prepared.
  • lubricating oil compositions of Examples 115 and Comparative Examples 115 were prepared with the formulations shown in Table 1 below using the following reference oils and additives.
  • all salts of the lubricating oil composition were used. Additives were added so that the base value was 5 mgKOH / g.
  • Zinc dithiophosphate 1.0 parts by mass
  • the metal content is derived from the detergent.
  • the total base number of the reference oil and B-5 is about 1 before the test and 0 or less after the test, so the difference is not entered.
  • the lubricating oil composition of the present invention has a kinematic viscosity difference of 0.4-0.9 mm 2 / S, a reduction in total base number of 1.91-2.05 mgKOH / g, and excellent oxidation stability. Slur It exhibited excellent sludge dispersibility of 0.0338-0.421 g.
  • the lubricating oil composition of the present invention does not contain a metal component derived from a detergent, even when used as an internal combustion engine lubricating oil, the exhaust gas purifying performance of an exhaust gas catalyst and the particulate matter removing performance of a diesel particulate removing device are reduced. I will not let you down.
  • Comparative Example 4 in which a tertiary amine compound (B-4) having a base number of 105 mgK ⁇ H / g was added, and a quaternary ammonium salt (B Comparative Example 5 to which —5) was added was inferior in oxidation stability and sludge dispersibility.

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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)

Abstract

Est décrit un additif pour huile lubrifiante ayant une excellente capacité de nettoyage sans composant métallique tel que le calcium ou le magnésium. Est également décrite une composition pour huile lubrifiante contenant ce type d’additif pour huile lubrifiante. L’additif pour huile lubrifiante est caractérisé par le fait qu’il contient un sel d’ammonium quaternaire ayant un indice d’alcalinité d’au moins 10 mgKOH/g. Les exemples de ce type de sel d’ammonium quaternaire comprennent les sels d’ammonium quaternaire obtenus par échange de sels des contre-anions contenus dans les tensioactifs cationiques tels que le chlorure de tétraalkylammonium et le sulfate de tétraalkylammonium.
PCT/JP2005/000913 2004-01-30 2005-01-25 Additif pour huile lubrifiante et composition pour huile lubrifiante contenant celui-ci WO2005073351A1 (fr)

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EP05709314A EP1717298A4 (fr) 2004-01-30 2005-01-25 Additif pour huile lubrifiante et composition pour huile lubrifiante contenant celui-ci
CA002552671A CA2552671A1 (fr) 2004-01-30 2005-01-25 Additif pour huile lubrifiante et composition pour huile lubrifiante contenant celui-ci
US10/587,020 US20070155636A1 (en) 2004-01-30 2005-01-25 Lubricating oil additive and lubricating oil composition containing the same

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JP2004-024309 2004-01-30
JP2004024309A JP4594626B2 (ja) 2004-01-30 2004-01-30 内燃機関潤滑油用又は駆動系潤滑油用潤滑油組成物

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EP1970432A1 (fr) * 2006-12-19 2008-09-17 Castrol Limited Compositions lubrifiantes et utilisations
JP2010053352A (ja) * 2008-07-31 2010-03-11 Sanyo Chem Ind Ltd 潤滑油添加剤及び潤滑油組成物
PL2514807T5 (pl) * 2009-05-15 2021-03-08 The Lubrizol Corporation Czwartorzędowe amidowe sole amonowe
US20120010112A1 (en) 2010-07-06 2012-01-12 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
JP5808775B2 (ja) * 2013-07-05 2015-11-10 株式会社椿本チエイン チェーン用潤滑剤組成物及びチェーン
US9677020B2 (en) 2014-06-25 2017-06-13 Afton Chemical Corporation Hydrocarbyl soluble quaternary ammonium carboxylates and fuel compositions containing them
KR102622894B1 (ko) 2015-04-09 2024-01-08 더루브리졸코오퍼레이션 사차 암모늄 화합물을 함유하는 윤활제
CN108026473A (zh) * 2015-07-20 2018-05-11 路博润公司 无锌润滑组合物

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EP1717298A4 (fr) 2012-07-11
US20070155636A1 (en) 2007-07-05

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