US20070155636A1 - Lubricating oil additive and lubricating oil composition containing the same - Google Patents

Lubricating oil additive and lubricating oil composition containing the same Download PDF

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Publication number
US20070155636A1
US20070155636A1 US10/587,020 US58702005A US2007155636A1 US 20070155636 A1 US20070155636 A1 US 20070155636A1 US 58702005 A US58702005 A US 58702005A US 2007155636 A1 US2007155636 A1 US 2007155636A1
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Prior art keywords
lubricating oil
acid
group
oil
additive according
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US10/587,020
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Naomi Koishikawa
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Adeka Corp
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Adeka Corp
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Publication of US20070155636A1 publication Critical patent/US20070155636A1/en
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • 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
    • C10M2207/10—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
    • 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
    • C10M2215/02—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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines

Definitions

  • the present invention relates to a lubricating oil additive and a lubricating oil composition containing the same.
  • a metal-based cleaning agent has been conventionally added to engine oil for the purpose of lengthening the lifetime of the engine oil.
  • the metal-based cleaning agent functions to prevent the deposition of sludge in an engine and to neutralize acid substances as by-products of the burning of fuel or as products obtained as a result of deterioration of the engine oil.
  • Perbasic sulfonate, phenate, salicylate, or the like has been used in such metal-based cleaning agents.
  • a metal-based cleaning agent composed of perbasic calcium sulfonate, calcium salicylate, magnesium sulfonate, or the like has been most generally used because it is relatively inexpensive and has excellent cleaning performance.
  • part of a metal-based cleaning agent is burnt together with fuel, and metal components in the metal-based cleaning agent cause various problems.
  • metal components released together with exhaust gas adhere to an exhaust gas catalyst to reduce exhaust gas clarifying performance, and, in a diesel engine, reduces the particulate matter (PM) removal performance of a diesel particulate filter (DPF) and inhibits the reuse of the DPF. Therefore, a reduction in amount of a metal-based cleaning agent to be added is of great concern.
  • PM particulate matter
  • DPF diesel particulate filter
  • Patent Document 1 JP 2000-256690 A
  • Patent Document 2 JP 09-100485 A
  • Patent Document 3 JP 09-013067 A
  • Patent Document 4 JP 2877887 B
  • the present invention has been made with a view to solving such problems as described above, and an object of the present invention is to provide a lubricating oil additive which is free of metal components such as calcium or magnesium and is excellent in cleaning performance and a lubricating oil composition containing the same.
  • a quaternary ammonium salt having a specific base number and containing no metal components has cleaning performance comparable to or higher than that of a conventional metal-based cleaning agent, to complete the invention.
  • the present invention relates to a lubricating oil additive containing a quaternary ammonium salt having a base number of at least 10 mgKOH/g.
  • the present invention provides a lubricating oil composition containing 0.1 to 10% by mass of the above lubricating oil additive based on a base oil.
  • metal refers to a “typical metal element” and a “transition metal element”.
  • a lubricating oil additive containing a quaternary ammonium salt having a base number of at least 10 mgKOH/g can provide a lubricating oil composition having an extremely small amount of metal components such as calcium or magnesium and excellent cleaning performance.
  • the lubricating oil additive according to the present invention contains a quaternary ammonium salt having a base number of at least 10 mgKOH/g.
  • the quaternary ammonium salt may be directly used as the lubricating oil additive, or may be mixed with base oil or any other additive to be used in a lubricating oil composition described later before being used as the lubricating oil additive.
  • the base number of the quaternary ammonium salt is preferably high from the viewpoint of sludge dispersibility or acid neutralizing properties. However, an excessively high base number is not preferable because such base number may increase the frictional coefficient of lubricating oil, or may deteriorate solubility into base oil. Therefore, the base number of the quaternary ammonium salt is preferably 30 to 600 mgKOH/g, or more preferably 50 to 300 mgKOH/g.
  • base number refers to the number of milligrams (mg) of potassium hydroxide in an amount equivalent to that of hydrochloric acid needed for neutralizing a basic component in 1 g of a quaternary ammonium salt.
  • the base number can be measured by means of the total base number measuring method of JIS K2501 (petroleum product and lubricating oil-neutralization number testing method).
  • quaternary ammonium salts obtained by subjecting counter anions in cationic surfactants such as tetraalkylammonium chloride and tetraalkylammonium sulfate to salt-exchange.
  • 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 9 O—CO—R 10 , or —R 11 NH—CO—R 12 (provided that at least one of R 1 to R 4 represents a hydrocarbon group having 1 to 30 carbon atoms), R 9 and R 11 each represent a hydrocarbon group having 1 to 4 carbon atoms, R 10 and R 12 each represent a hydrocarbon group having 1 to 30 carbon atoms or a hydrogen atom, and X ⁇ represents an anionic group.
  • Examples of a hydrocarbon group having 1 to 30 carbon atoms represented by each of R 1 to R 4 , R 10 , and R 12 include: alkyl groups such as a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, secondary butyl group, tertiary butyl group, pentyl group, isopentyl group, secondary pentyl group, neopentyl group, tertiary pentyl group, hexyl group, secondary hexyl group, heptyl group, secondary heptyl group, octyl group, 2-ethylhexyl group, secondary octyl group, nonyl group, secondary nonyl group, decyl group, secondary decyl group, undecyl group, secondary undecyl group, dodecyl group, secondary dodecyl group, tridecyl group, isotri
  • Examples of a hydrocarbon group having 1 to 4 carbon atoms represented by each of R 9 and R 11 includes a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, or secondary butyl group. Of those, a linear alkyl group is preferable, and an ethyl group, propyl group, and isopropyl group are more preferable because of easy availability of raw materials for them.
  • X ⁇ represents an anionic group.
  • X ⁇ as an anionic group may have a value of pk a (equilibrium constant) that is an index of acidity of more than 0 when X ⁇ is represented as an acidic compound HX.
  • anionic group examples include groups derived from: inorganic compounds such as carbonic acid, boric acid, and silicic acid; carbonates such as monomethyl carbonate and monoethyl carbonate; and organic carboxylic acids such as formic acid, acetic acid, propionic acid, butanoic acid (butyric acid), pentanoic acid (valeric acid), isopentanoic acid (isovaleric acid), hexanoic acid (capronic 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, undecylic acid, isoundecylic acid, dodecanoic acid (lauric acid), isododecanoic acid, tridecanoic acid,
  • a quaternary ammonium salt represented by the general formula (1) of the present invention can be manufactured as follows. At least one tertiary amine selected from the group consisting of tertiary amine compounds, tertiary amineamide compounds, tertiary amine ester compounds, and tertiary amineamide ester compounds is used as a starting material. Then, the tertiary amine is quaternized with a quaternizing agent. It should be noted that well-known methods may be used for salt-exchange when a counter anion of the compound obtained by quaternization is a group other than the above-described anionic groups.
  • an 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-described acidic compound HX and produced water is dehydrated.
  • the hydroxyl group can be replaced with an anionic group derived from an organic carboxylic acid.
  • Examples of a tertiary amine compound which is a starting material include: alkyl tertiary amines such as trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, tridodecylamine, tritetradecylamine, trihexadecylamine, trioctadecylamine, trieicosylamine, tridocosylamine, tritetracosylamine, trihexacosylamine, trioctacosylamine, triacontylamine, monomethyldiethylamine, monomethyldibutylamine, monomethyldihexylamine, monomethyldioctylamine, monomethyldidecylamine, monomethyldidodecylamine, monomethylditetradecylamine, monomethyldihex
  • a tertiary amineamide compound which is a starting material can be manufactured by the following method.
  • An amine compound such as: triamine having two primary amine groups and one secondary amine group such as diethylenetriamine, dipropylenetriamine, or ethylenepropylenetriamine; a triamine having two primary amine groups and one tertiary amine group such as bis(3-aminopropyl)methylamine, bis(3-aminopropyl)ethylamine, bis(3-aminopropyl)propylamine, bis(3-aminopropyl)butylamine, or bis (3-aminopropyl)benzylamine; or a diamine having one primary amine group such as N,N-dimethylethylenediamine, N,N-diethylethylenediamine, N,N-dipropylethylenediamine, N,N-dibutylethylenediamine, N,N-dimethylpropylenediamine, N,N
  • an amineamide compound is obtained.
  • the secondary amine group can be tertiarized with halogenated hydrocarbon, dialkylsulfate, or the like to thereby obtain a tertiary amineamide compound.
  • tertiary amine ester compound which is a starting material examples include tertiary alkanolamines such as triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, N-propyldiethanolamine, N-isopropyldiethanolamine, N-butyldiethanolamine, N,N-dimethylethanolamine, N,N-diethylethanolamine, N,N-dipropylethanolamine, N,N-dibutylethanolamine, N-cyclohexyldiethanolamine, N-benzyldiethanolamine, tripropanolamine, triisopropanolamine, N-cyclohexyldiisopropanolamine, N-benzyldiisopropanolamine, and tributanolamine.
  • tertiary alkanolamines such as triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, N-propy
  • the tertiary amine ester compound can also be obtained as follows.
  • a primary alkanolamine or secondary alkanolamine such as monoethanolamine, diethanolamine, N-methylethanolamine, N-ethylethanolamine, N-propylethanolamine, N-isopropylethanolamine, N-butylethanolamine, N-cyclohexylethanolamine, N-benzylethanolamine, monopropanolamine, dipropanolamine, monoisopropanolamine, diisopropanolamine, N-cyclohexylisopropanolamine, N-benzylisopropanolamine, monobutanolamine, or dibutanolamine is tertiarized with halogenated hydrocarbon, dialkylsulfate, or the like. After that, the resultant is allowed to react with aliphatic acid, aliphatic acid chloride, or aliphatic acid ester to esterify a hydroxyl group of the amine compound
  • a tertiary amineamide ester compound which is a starting material can be manufactured by the following method.
  • An alcanoldiamine such as N-methanolethylenediamine, N-ethanolethylenediamine, N-propanolethylenediamine, N-butanolethylenediamine, N,N-dimethanolethylenediamine, N,N-diethanolethylenediamine, N,N-dipropanolethylenediamine, N,N-dibutanolethylenediamine, N-methanolpropylenediamine, N-ethanolpropylenediamine, N-propanolpropylenediamine, N-butanolpropylenediamine, N,N-dimethanolpropylenediamine, N,N-diethanolpropylenediamine, N,N-dipropanolpropylenediamine, or N,N-dibutanolpropylenediamine is allowed to react with aliphatic acid, aliphatic acid
  • a primary amine group and a hydroxyl group of the alcanoldiamine are subjected to an amidation reaction and an esterification reaction.
  • an amineamide ester compound can be obtained.
  • the secondary amine group can be tertiarized with halogenated hydrocarbon, dialkylsulfate, or the like to thereby obtain a tertiary amineamide ester compound.
  • Examples of an aliphatic acid to be used in the amidation of a primary amine group or in the amidation and esterification of a primary amine group and a hydroxyl group include formic acid, acetic acid, propionic acid, butanoic acid (butyric acid), pentanoic acid (valeric acid), isopentanoic acid (isovaleric acid), hexanoic acid (capronic 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, undecanoic acid, isoundecanoic acid, dodecanoic acid (lauric acid), isododecanoic acid, tridecanoic acid, isotridecanoic acid,
  • natural fats and oils include: vegetable fats and oils such as linseed oil, perilla oil, oiticica oil, olive oil, cacao oil, kapok oil, white mustard oil, sesame oil, rice bran oil, safflower oil, shea nut oil, china wood oil, soybean oil, tea oil, camellia oil, corn oil, rapeseed oil, palm oil, palm kernel oil, castor oil, sunflower oil, cottonseed oil, coconut oil, haze wax, and peanut oil; and animal fats and oils such as horse tallow, beef tallow, hoof oil, ghee, lard, goat tallow, mutton tallow, milk fat, fish oil, and whale oil.
  • vegetable fats and oils such as linseed oil, perilla oil, oiticica oil, olive oil, cacao oil, kapok oil, white mustard oil, sesame oil, rice bran oil, safflower oil, shea nut oil, china wood oil, soybean oil, tea oil,
  • a known method can be used as a reaction method for quaternarization.
  • the method involves: loading tertiary amine into an autoclave; adding a quaternarizing agent at 60° C. to 200° C.; and aging the resultant till the completion of a reaction.
  • Pressurization may be performed in an inert gas such as nitrogen or helium with a view to increasing a reaction velocity or a reaction rate.
  • the amount of the quaternarizing agent to be added is 1.0 to 4.0 mol, preferably 1.1 to 2.5 mol, or more preferably 1.1 to 1.8 mol with respect to 1 mol of the tertiary amine.
  • An excessively small amount of the quaternarizing agent to be added may fail to complete the reaction.
  • An excessively large amount of the quaternarizing agent to be added may cause a large amount of an unreacted quaternarizing agent to remain to have an adverse effect on an environment such as the release of the agent to the atmosphere.
  • Examples of a quaternarizing agent to be used for quaternarization include: organic halides such as methyl chloride, benzyl chloride, cyclohexyl chloride, methyl bromide, benzyl bromide, and cyclohexyl bromide; dialkyl sulfates such as dimethyl sulfate and diethyl sulfate; dialkyl carbonates such as dimethyl carbonate and diethyl carbonate; and trialkyl phosphates such as trimethyl phosphate and triethyl phosphate.
  • organic halides such as methyl chloride, benzyl chloride, cyclohexyl chloride, methyl bromide, benzyl bromide, and cyclohexyl bromide
  • dialkyl sulfates such as dimethyl sulfate and diethyl sulfate
  • dialkyl carbonates such as dimethyl carbonate and diethyl carbonate
  • quaternary ammonium hydroxide examples include: a method involving synthesizing quaternary ammonium hydroxide from a quaternary ammonium halide salt, which is obtained by reacting a tertiary amine and an alkyl halide, by means of an electrolytic method (JP 45-28564 B), an ion-exchange resin method (JP 52-3009 A), or the like, neutralizing the quaternary ammonium hydroxide with an acid compound HX, and removing produced water; and a method involving reacting a quaternary ammonium halide salt and an inorganic alkali such as sodium hydroxide or potassium hydroxide, removing the produced inorganic salt to provide quaternary ammonium hydroxide, and neutralizing the quaternary ammonium hydroxide with an acid compound HX.
  • an organic solvent can be used in a quaternarization reaction and a salt-exchange reaction as long as the solvent does not inhibit any one of the reactions.
  • the organic solvent that can be used in the reactions is not particularly limited. Specific examples of such solvent include: aliphatic, alicyclic, aromatic, and heterocyclic compounds, or a mixture of them; and general lubricating oil.
  • solvent examples include: alkanes such as pentane, hexane, heptane, cyclopentane, cyclohexane, ligroin, and petroleum ether; alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, 2-butanol, pentanol, hexanol, heptanol, octanol, and 2-ethylhexanol; alkyl ethers such as dimethyl ether, ethylmethyl ether, diethyl ether, methyl isobutyl ether, and ethyl isopropyl ether; ketones such as acetone, ethyl methyl ketone, and methyl isobutyl ketone; aromatic compounds such as benzene, toluene, xylene, and ethylbenzene; synthetic oils such as poly- ⁇ -olef
  • alkanes such as hexane, heptane, and petroleum ether
  • alcohols such as methanol, ethanol, propanol, and 2-propanol
  • aromatic compounds such as benzene, toluene, and xylene
  • paraffin-based mineral oil naphthene-based mineral oil, and the like
  • adding any one of those solvents is preferable for effectively removing by-products and impurities and for dissolving solid reaction products.
  • the lubricating oil composition according to the present invention contains 0.1 to 10%, or preferably 0.2 to 8% by mass of the above lubricating oil additive based on a base oil. Within the content range, cleaning performance such as sludge dispersibility or acid neutralizing property can be improved without any impairment of lubricity.
  • the base oil has only to be a base oil generally used in lubricating oil.
  • the base oil include mineral oil, hydrocarbon-based synthetic oil, and a mixture of them. More specific examples of the base oil include: synthetic oils such as poly- ⁇ -olefin, ethylene- ⁇ -olefin copolymers, polybutene, alkylbenzene, alkylnaphthalene, polyalkylene glycol, polyphenyl ether, an alkyl-substituted diphenyl ether, polyol ester, dibasic ester, phosphate, phosphite, carbonate, silicone oil, and fluorinated oil; and paraffin-based mineral oil and naphthene-based mineral oil, or purified mineral oils obtained by purifying them.
  • the lubricating oil composition of the present invention does not inhibit the addition of any known lubricating oil additive.
  • the composition may be added with, for example, antioxidants, organic molybdenum-based additives, extreme pressure agents, oiliness improvers, metal-based cleaning agents, dispersants, viscosity index improvers, pour depressants, rust inhibitors, corrosion inhibitors, or defoaming agents for an intended purpose.
  • antioxidants examples include a zinc dithiophosphate-based antioxidant, a phenol-based antioxidant, and an amine-based antioxidant.
  • the preferable loading of any one of those antioxidants is 0.1 to 5% by mass based on the base oil.
  • Examples of the organic molybdenum-based additive include: oxymolybdenum dithiocarbamate sulfide; oxymolybdenum dithiophosphate sulfide; aliphatic molybdenum salts; oxymolybdenum xanthate sulfide; reaction products between molybdenum trioxide and acid phosphate; reaction products between molybdenum trioxide and aliphatic diethanol amide; reaction products between molybdenum trioxide and glycerin monoaliphatic acid ester; reaction products between succinimide, amide carboxylate, Mannich base, or a boride of any one of them and molybdenum trioxide; and reaction products between amine and a molybdenum compound having a pentavalent or hexavalent molybdenum atom.
  • the preferable loading of any one of those organic molybdenum-based additives is 0.001 to 5% by mass based on the base
  • extreme pressure agent examples include: sulfur-based compounds such as sulfurized fats and oils, olefin polysulfide, and dibenzyl sulfide; phosphor compounds such as monooctyl phosphate, tributyl phosphate, triphenyl phosphite, tributyl phosphite, and thiophosphate; and organometallic compounds such as metal thiophosphates, metal thiocarbamates, and acid metal phosphates.
  • the preferable loading of any one of those 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; aliphatic acids such as oleic acid and stearic acid; esters such as oleyl glycerin ester, lauryl glycerin ester, oleyl sorbitan ester, and oleyl trimethylolpropane ester; amides such as laurylamide, oleylamide, and stearylamide; amines such as laurylamine, oleylamine, and stearylamine; and ethers such as lauryl glycerin ether and oleyl glycerin ether.
  • the preferable loading of any one of those oiliness improvers is 0.1 to 10% by mass based on the base oil.
  • the metal-based cleaning agent examples include the sulfonates, phenates, salicylates, phosphonates, and perbasic salts of calcium, magnesium, barium, and the like.
  • the loading of any one of those metal-based cleaning agents is preferably small from the viewpoint of the alleviation of the load on the environment.
  • the composition may be blended with 0 to 10%, or preferably 0 to 5% by mass of anyone of those metal-based cleaning agents based on the base oil.
  • dispersant examples include succinimide, benzylamine, succinate, and boron-denatured products of them.
  • the preferable loading of any one of those dispersants is 0.5 to 10% by mass based on the base oil.
  • viscosity index improver examples include: polyalkyl methacrylate (having 1 to 18 carbon atoms), alkyl acrylate (having 1 to 18 carbon atoms)/alkyl methacrylate (having 1 to 18 carbon atoms) copolymers; diethylaminoethyl methacrylate/alkyl methacrylate (having 1 to 18 carbon atoms) copolymers; ethylene/alkyl methacrylate (having 1 to 18 carbon atoms) copolymers; polyisobutylene; polyalkylstyrene; ethylene/propylene copolymers; styrene/maleate copolymers; styrene/maleic acid amide copolymers; styrene/butadiene hydrogenated copolymers; and styrene/isoprene hydrogenated copolymers.
  • Each of those viscosity index improvers has an average molecular weight of about 10,000
  • pour depressant examples include polyalkyl methacrylate, polyalkyl acrylate, polyalkylstyrene, and polyvinyl acetate. Each of those pour depressants has an average molecular weight of about 1,000 to 100,000. The preferable loading of any one of those pour depressants is 0.005 to 3% by mass based on the base oil.
  • rust inhibitor examples include: sodium nitrite; oxidized paraffin wax calcium salts; oxidized paraffin wax magnesium salts; beef tallow aliphatic acid alkali metal salts, alkali earth metal salts, or amine salts; alkenyl succinic acid or alkenyl succinic acid half esters (in which an alkenyl group has a molecular weight of about 100 to 300); sorbitan monoesters; pentaerythritol monoesters; nonyl phenol ethoxylates; lanolin aliphatic acid esters; and lanolin aliphatic acid calcium salts.
  • the preferable loading of any one of those rust inhibitors is 0.01 to 5% by mass based on the base oil.
  • corrosion inhibitor examples include benzotriazole, benzoimidazole, benzothiazole, and tetraalkylthiuram disulfide.
  • the preferable loading of any one of those corrosion inhibitors is 0.01 to 3% by mass based on the base oil.
  • defoaming agent examples include polydimethyl silicone, trifluoropropylmethyl silicone, colloidal silica, polyalkyl acrylate, polyalkyl methacrylate, alcohol ethoxy/propoxylate, aliphatic acid ethoxy/propoxylate, and sorbitan partial aliphatic acid ester.
  • the preferable loading of any one of those defoaming agents is 0.001 to 1% by mass based on the base oil.
  • the lubricating oil composition of the present invention can be suitably used in any one of automobile and industrial greases typified by internal combustion engine lubricating oil, driving system lubricating oil (such as manual transmission oil, differential gear oil, or automatic transmission oil), lubricating oil for metal working, and grease for constant velocity joints.
  • driving system lubricating oil such as manual transmission oil, differential gear oil, or automatic transmission oil
  • lubricating oil for metal working such as oil for metal working
  • grease for constant velocity joints lubricating oil
  • the composition can be suitably used in lubricating oil for internal combustion engines such as gasoline engines, diesel engines, or jet engines.
  • % means “% by mass” unless otherwise stated.
  • a reference oil having the formulation shown below was prepared.
  • a lubrication oil composition of each of Examples 1 to 5 and Comparative Examples 1 to 5 was prepared by means of the following reference oil and each additive according to the formulation shown in Table 1 below.
  • an additive was added in such a manner that the total base number of a lubricating oil composition would be 5 mgKOH/g.
  • Base oil 100 parts by mass Succinimide-based dispersant 5.0 parts by mass Phenol-based antioxidant 0.3 part by mass Amine-based antioxidant 0.3 part by mass Zinc dithiophosphate 1.0 part by mass ⁇ Additive>
  • Oxidation stability is higher as a difference between the dynamic viscosity before the test and the dynamic viscosity after the test is smaller and the amount of a reduction in total base number is smaller.
  • the corrosion of a metal is reduced and dispersibility is higher as the amount of produced sludge is smaller. Table 1 shows the results.
  • a metal component shown is derived from a cleaning agent. * The difference in total base number of each of the reference oil and B-5 is not written because the total base number of each of them before the test is about 1 and the total base number of each of them after the test is equal to or less than 0.
  • the lubricating oil composition of the present invention had a difference in dynamic viscosity of 0.4 to 0.9 mm 2 /S and an amount of a reduction in total base number of 1.91 to 2.05 mgKOH/g. That is, the composition showed excellent oxidation stability.
  • the composition had a sludge amount of 0.0338 to 0.0421 g. That is, the composition showed excellent sludge dispersibility.
  • the composition was comparable to or better than any one of the lubricating oil compositions with the conventional metal-based cleaning agents added (B-1 to B-3) in terms of all of a difference in dynamic viscosity, a sludge amount, and the amount of a reduction in total base number.
  • the lubricating oil composition of the present invention does not reduce the exhaust gas clarifying performance of an exhaust gas catalyst or the particulate matter removing performance of a diesel particulate filter even when the composition is used in internal combustion engine lubricating oil because the composition does not contain any metal components derived from a cleaning agent.
  • each of the lubricating oil compositions of Comparative Example 4 added with the tertiary amine compound (B-4) having a base number of 105 mgKOH/g and the lubricating oil composition of Comparative Example 5 added with the quaternary ammonium salt (B-5) having a base number of 0 mgKOH/g was poor in oxidation stability and sludge dispersibility.

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  • General Chemical & Material Sciences (AREA)
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  • Organic Chemistry (AREA)
  • Lubricants (AREA)
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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
PCT/JP2005/000913 WO2005073351A1 (ja) 2004-01-30 2005-01-25 潤滑油添加剤及びそれを含有する潤滑油組成物

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US9255236B2 (en) 2010-07-06 2016-02-09 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
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WO2016164345A1 (en) 2015-04-09 2016-10-13 The Lubrizol Corporation Lubricants containing quaternary ammonium compounds
US9677020B2 (en) 2014-06-25 2017-06-13 Afton Chemical Corporation Hydrocarbyl soluble quaternary ammonium carboxylates and fuel compositions containing them

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WO2010132259A1 (en) * 2009-05-15 2010-11-18 The Lubrizol Corporation Quaternary ammonium amide and/or ester salts
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US9988589B2 (en) 2010-07-06 2018-06-05 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
US9587194B2 (en) 2010-07-06 2017-03-07 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
US10344241B2 (en) 2010-07-06 2019-07-09 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
US9255236B2 (en) 2010-07-06 2016-02-09 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
US20160137948A1 (en) * 2013-07-05 2016-05-19 Tsubakimoto Chain Co. Lubricant composition for chains, and chain
US9677020B2 (en) 2014-06-25 2017-06-13 Afton Chemical Corporation Hydrocarbyl soluble quaternary ammonium carboxylates and fuel compositions containing them
WO2016164345A1 (en) 2015-04-09 2016-10-13 The Lubrizol Corporation Lubricants containing quaternary ammonium compounds

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