WO2015014629A1 - Composition d'huile lubrifiante ayant une meilleure résistance à la corrosion - Google Patents

Composition d'huile lubrifiante ayant une meilleure résistance à la corrosion Download PDF

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Publication number
WO2015014629A1
WO2015014629A1 PCT/EP2014/065386 EP2014065386W WO2015014629A1 WO 2015014629 A1 WO2015014629 A1 WO 2015014629A1 EP 2014065386 W EP2014065386 W EP 2014065386W WO 2015014629 A1 WO2015014629 A1 WO 2015014629A1
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Prior art keywords
lubricating oil
oil composition
weight
ppm
alkyl
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PCT/EP2014/065386
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English (en)
Inventor
Thomas RÜHLE
Matthias Hof
Reiner KRIPP
Andreas Minke
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Basf Se
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Publication of WO2015014629A1 publication Critical patent/WO2015014629A1/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
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/40—Six-membered ring containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic 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
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/0206—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers 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
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms 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
    • C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
    • C10M2205/223—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/2805—Esters used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C10M2207/2825—Esters of (cyclo)aliphatic oolycarboxylic 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2223/0405—Phosphate esters 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
    • 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
    • C10N2030/12—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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for 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
    • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/242—Hot working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/243—Cold working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2040/252—Diesel engines
    • 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
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • 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
    • C10N2040/32—Wires, ropes or cables lubricants
    • 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
    • C10N2040/36—Release agents or mold release agents
    • 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
    • C10N2040/46—Textile oils
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • the presently claimed invention relates to a lubricating oil composition
  • a lubricating oil composition comprising 1 ,8- diazabicyclo-5,4,0-undecene-7, at least one base stock and one or more performance additives; the use of 1 ,8-diazabicyclo-5,4,0-undecene-7 to prevent corrosion in a lubricating oil composition and a method for enhancing the corrosion resistance of a lubricating oil formulation comprising the addition of 1 ,8-diazabicyclo-5,4,0-undecene-7.
  • Lubricating oil compositions perform numerous functions. In engines they function to reduce friction and wear of numerous parts in moving contact with each other such as piston rings and cylinder walls, valves, cams, bearings, etc. They also function to cool the engine by operating as a heat sink and to clean the engine by carrying away combustion products and engine wear debris. Consequently, engine oils accumulate various and numerous contaminants which are or can be harmful to the engine. Similarly, engine oils by being exposed to extremes of heat are subjected to oxidation which further increases the concentrations of various contaminants in the oil. The same can be said for lubricating oil compositions other than engine oils. Transmission fluids, hydraulic oils, gear oils, turbine oils, functional fluids, industrial oils all function to lubricate parts in moving relationship with each other and in the course of their use accumulate various contaminants which are or can be harmful to the parts being lubricated.
  • Corrosion can occur at the very beginning of the lubricating process if the oil contains an additive which, while desirable for some purpose such as antiwear or friction reduction, also by its very chemical make-up is corrosive to metal, or the oil can become corrosive over time as contaminants build up in the oils as a consequence of accumulation of combus- tion products (and their conversion into corrosive materials) or during lubricant aging, oxidation and normal deterioration.
  • an additive which, while desirable for some purpose such as antiwear or friction reduction, also by its very chemical make-up is corrosive to metal, or the oil can become corrosive over time as contaminants build up in the oils as a consequence of accumulation of combus- tion products (and their conversion into corrosive materials) or during lubricant aging, oxidation and normal deterioration.
  • Lubricating oil compositions are formulated to include anti-corrosion additives.
  • Surface active metal passivators are included into the lubricating oil composition to interact with the surfaces of the metal parts and render the metal resistant to the action of corrosive materials, be they other additives or accumulated contaminants, in the lubricating oil compositions.
  • Anti-rust additives corrosion inhibitors
  • Some anti-rust additives are polar compounds that wet the metal surface preferentially, protecting the metal surface with a hydrocarbona- ceous-type or oil-type film.
  • anti-rust/anti-corrosion additives absorb water by incorporat- ing it into a water-in-oil emulsion so that only the continuous oil phase is in contact with the metal surface.
  • anti-rust additives chemically adhere to the metal to produce a non- reactive surface.
  • Suitable additives include zinc dithiophosphates, metal phenolates, basic metal sulfonates, weak fatty acids, amines.
  • Other metal corrosion inhibitors include thiadiazoles, e.g., dialkyl dimercapto thiadiazoles, tria- zoles, e.g., benzotriazole, tolyltriazole.
  • Such anti-corrosion materials are commonly incorporated into oils in an amount in the range of about 0.01 to 5.0 wt.-%, preferably about 0.01 to 1 .5 wt.-%, more commonly, especially in the case of the surface active corrosion inhibitors, in an amount in the range of about 0.01 to 1 .0 wt.-%.
  • Lubricating oil compositions contain a wide range of base stocks that are very different in their chemical nature in order to fulfill different performance characteristics.
  • Ester base stocks for example, the neopentyl polyol esters and the pentaerythritol esters of monobasic carboxylic acids, have excellent high performance properties as indicated by their common use in gas turbine lubricants. They also provide excellent anti-wear characteristics when conventional anti-wear additives are present and they do not have any adverse effect on the performance of rust inhibitors. On the other hand, esters have relatively poor hydrolytic stability, undergoing hydrolysis readily in the presence of water at even moderate tempera- tures. They are, therefore, less well suited for use in wet applications such as paper-making machinery.
  • Hydrolytic stability can be improved by the use of hydrocarbon base stocks.
  • alkyl aromatics in combination with the other hydrocarbon base stocks such as hydrogenated poly- alphaolefin (PAO) synthetic hydrocarbons and the improved hydrolytic stability of these combinations is described, for example, in US 5,602,086.
  • PAO hydrogenated poly- alphaolefin
  • hydrolytic stability of hydrocarbon base stocks including PAO's is superior to that of the esters, it is frequently difficult to obtain a good balance of the surface-related properties such as anti-wear and anti-rust because, as noted above, these surface-related properties are dependent upon the extent to which the additives present in the base stock compete for sites on the metal surfaces which they are intended to protect and high quality hydrocarbon base stocks such as PAO's do not favorably interact with the additives used for this purpose.
  • PAO's high quality hydrocarbon base stocks
  • PAO's do not favorably interact with the additives used for this purpose.
  • lubricating oil compositions comprising optionally substituted 1 ,8-diazabicyclo-5,4,0-undecene-7.
  • the presently claimed invention is directed to a
  • R1 denotes hydrogen or branched or straight-chain and unsubstituted or at least
  • the presently claimed invention is directed to a lubricating oil composition
  • a lubricating oil composition comprising a) ⁇ 10 ppm to ⁇ 10 000 ppm of a compound of general formula (I),
  • R1 denotes hydrogen or branched or straight-chain and unsubstituted or at least mono-substituted C1-30 alkyl
  • % by weight of at least one base stock selected from the group consisting of mineral oils, polyalphaolefins, polymerized and interpolymerized olefins, alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters, and c) ⁇ 0.0 to ⁇ 25 % by weight of one or more performance additives, whereby the % by weight of the components a), b) and c) is in each case related to the overall weight of the lubricating oil, 9 composition and the sum of the weight of all components a), b) and c) adds up to 100 %.
  • the compound of general formula (I) is present in its base form, i.e. the compound of general formula (I) is not presented in its protonated form.
  • the inventively claimed lubricating oil composition does not contain any water.
  • lubricating oil composition refers to the combination of at least one base stock plus performance additives such as dispersants, metal deactivators, detergents, viscosity modifiers, extreme pressure agents (typically boron- and/or sulfur- and/or phosphorus- containing), antiwear agents, antioxidants (such as hindered phenols, aminic antioxidants or molybdenum compounds), corrosion inhibitors, foam inhibitors, de- mulsifiers, pour point depressants, seal swelling agents and friction modifiers.
  • performance additives such as dispersants, metal deactivators, detergents, viscosity modifiers, extreme pressure agents (typically boron- and/or sulfur- and/or phosphorus- containing), antiwear agents, antioxidants (such as hindered phenols, aminic antioxidants or molybdenum compounds), corrosion inhibitors, foam inhibitors, de- mulsifiers, pour point depressants, seal swelling agents and friction modifiers.
  • performance additives such as dispersants, metal deactivators, detergents
  • alkyl covers acyclic saturated hydrocarbon residues, which may be branched or straight-chain and unsubstituted or at least mono- substituted with, as in the case of C1-30 alkyl, 1 to 30 (i.e. 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 1 1 , 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27, 28, 29 or 30) C atoms.
  • substituents may be selected mutually independently from the group consisting of F, CI, Br, I,— N0 2 ,— CN,—OH,— SH,— NH 2 ,— N(CH 3 ) 2 ,— N(C 2 H 5 ) 2 and— N(CH 3 )(C 2 H 5 ).
  • branched denotes a chain of atoms with one or more side chains attached to it. Branching occurs by the replacement of a substituent, e.g., a hydrogen atom, with a covalent- ly bonded alkyl radical.
  • R1 denotes hydrogen or straight-chain, unsubstituted Ci -2 o alkyl; more preferably R1 denotes hydrogen or straight-chain, unsubstituted C1-10 alkyl; most preferably R1 denotes hydrogen.
  • R1 denotes hydrogen
  • the compound of general formula (I) is 1 ,8-diazabicyclo- 5,4,0-undecene-7.
  • the compound of general formula (I), preferably 1 ,8-diazabicyclo-5,4,0-undecene-7 is present in an amount of ⁇ 10 ppm to ⁇ 10 000 ppm, more preferably in an amount of ⁇ 10 ppm to ⁇ 5000 ppm, even more preferably in an amount of ⁇ 40 ppm to ⁇ 2500 ppm, most preferably in an amount of ⁇ 50 ppm to ⁇ 1000 ppm, in particular in an amount of ⁇ 100 ppm to ⁇ 500 ppm, related to the overall weight of the lubricating oil composition.
  • a lubricating oil composition can comprise base stocks and a variety of different performance additives in varying ratios.
  • the lubricating oil composition further comprises base stocks selected from the group consisting of mineral oils (Group I, II or III oils), polyalphaolefins (Group IV oils), polymerized and interpolymerized olefins, alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters (Group V oils).
  • base stocks selected from the group consisting of mineral oils (Group I, II or III oils), polyalphaolefins (Group IV oils), polymerized and interpolymerized olefins, alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters (Group V oils).
  • the lubricating oil comprises ⁇ 80 % to ⁇ 99 % by weight or ⁇ 80 % to ⁇ 99.99 % by weight or ⁇ 90 % to ⁇ 99 % by weight base stocks, related to the total amount of the lubricating oil composition.
  • Group I base stocks contain less than 90 percent saturates and/or greater than 0.03 percent sulfur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in the following table
  • Group II base stocks contain greater than or equal to 90 percent saturates and less than or equal to 0.03 percent sulfur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in the following table
  • Group III base stocks contain greater than or equal to 90 percent saturates and less than or equal to 0.03 percent sulfur and have a viscosity index greater than or equal to 120 using the test methods specified in the following table Analytical Methods for Base Stock
  • Group IV base stocks contain polyalphaolefins.
  • Synthetic lower viscosity fluids suitable for the present invention include the polyalphaolefins (PAOs) and the synthetic oils from the hy- drocracking or hydroisomerization of Fischer Tropsch high boiling fractions including waxes. These are both stocks comprised of saturates with low impurity levels consistent with their synthetic origin.
  • the hydroisomerized Fischer Tropsch waxes are highly suitable base stocks, comprising saturated components of iso-paraffinic character (resulting from the isomerization of the predominantly n-paraffins of the Fischer Tropsch waxes) which give a good blend of high viscosity index and low pour point.
  • Polyalphaolefins suitable for the present invention include known PAO materials which typically comprise relatively low molecular weight hydrogenated polymers or oligomers of alphaole- fins which include but are not limited to C2 to about C32 alphaolefins with the Cs to about C 16 alphaolefins, such as 1 -octene, 1 -decene, 1 -dodecene and the like being preferred.
  • the preferred polyalphaolefins are poly-1 -octene, poly-1 -decene, and poly-1 -dodecene, although the dimers of higher olefins in the range of C14 to C18 provide low viscosity base stocks.
  • Low viscosity PAO fluids suitable for the present invention may be conveniently made by the polymerization of an alphaolefin in the presence of a polymerization catalyst such as the Friedel- Crafts catalysts including, for example, aluminum trichloride, boron trifluoride or complexes of boron trifluoride with water, alcohols such as ethanol, propanol or butanol, carboxylic acids or esters such as ethyl acetate or ethyl propionate.
  • a polymerization catalyst such as the Friedel- Crafts catalysts including, for example, aluminum trichloride, boron trifluoride or complexes of boron trifluoride with water, alcohols such as ethanol, propanol or butanol, carboxylic acids or esters such as ethyl acetate or ethyl propionate.
  • a polymerization catalyst such as the Friedel- Crafts catalysts including, for example, aluminum t
  • Patents 3,742,082 (Brennan); 3,769,363 (Brennan); 3,876,720 (Heilman); 4,239,930 (Allphin); 4,367,352 (Watts); 4,413,156 (Watts); 4,434,408 (Lar- kin); 4,910,355 (Shubkin); 4,956,122 (Watts); and 5,068,487 (Theriot).
  • Group V base stocks contain any base stocks not described by Groups I to IV.
  • Examples of Group V base stocks include alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters.
  • Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(l -hexenes), poly(1 - octenes), poly(l -decenes)); alkylbenzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl)benzenes); polyphenyls (e.g., biphenyls,
  • carboxylic acid esters suitable for the present invention include the esters of mono and polybasic acids with monoalkanols (simple esters) or with mixtures of mono and polyalkanols (complex esters), and the polyol esters of monocarboxylic acids (simple esters), or mixtures of mono and polycarboxylic acids (complex esters).
  • Esters of the mono/polybasic type include, for example, the esters of monocarboxylic acids such as heptanoic acid, and dicarboxylic acids such as phthalic acid, succinic acid, alkyl succinic acid, alkenyl succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acid, alkenyl malonic acid, etc., with a variety of alcohols such as butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, or mixtures thereof with polyalkanols, etc.
  • monocarboxylic acids such as heptanoic acid
  • dicarboxylic acids such as phthalic acid, succinic acid, alkyl succinic acid, alkenyl succinic acid, maleic acid, azelaic acid,
  • esters include nonyl heptanoate, dibutyl adipate, di(2- ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, dibutyl -TMP- adipate, di- isodecyl adipate, di-propyladipate, di-isotridecyl adipate, tri methyl propyl tricaprylate, di-isooctyl adipate, di-ethylhexyl adipate and di-nonyl adipate.
  • esters such as those obtained by reacting one or more polyhydric alcohols, preferably the hindered polyols such as the neopentyl polyols, e.g. neopentyl glycol, trimethylol ethane, 2-methyl-2-propyl-1 ,3-propanediol, trimethylol propane, trimethylol butane, pentaerythritol and dipentaerythritol with monocarboxylic acids containing at least 4 carbons, normally the Cs to C30 acids such as saturated straight chain fatty acids including caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, and behenic acid, or the corresponding branched chain fatty acids or unsaturated fatty acids such as oleic acid, or mixtures thereof, with polycarboxylic acids.
  • the hindered polyols such as the neopentyl poly
  • Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc. constitute another class of known synthetic lubricating oils. These are exemplified by polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide, and the alkyl and aryl ethers of polyox- yalkylene polymers (e.g., methyl-polyiso-propylene glycol ether having a molecular weight of 1000 or diphenyl ether of poly-ethylene glycol having a molecular weight of 1000 to 1500); and mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C3-C8 fatty acid esters and C13 Oxo acid diester of tetraethylene glycol.
  • polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide
  • Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy- or polyaryloxysilicone oils and silicate oils comprise another useful class of synthetic lubricants; such oils include tetraethyl silicate, tetraisopropyl silicate, tetra-(2- ethylhexyl)silicate, tetra-(4-methyl-2-ethylhexyl)silicate, tetra-(p-tert-butyl-phenyl) silicate, hexa-(4-methyl-2-ethylhexyl)disiloxane, oly(methyl)siloxanes and poly(methylphenyl)siloxanes.
  • oils include tetraethyl silicate, tetraisopropyl silicate, tetra-(2- ethylhexyl)silicate, tetra-(4-methyl-2-ethy
  • Other synthetic lubricating oils include liquid esters of phos- phorous-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid) and polymeric tetrahydrofurans.
  • phos- phorous-containing acids e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid
  • polymeric tetrahydrofurans e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid
  • the lubricating oil composition of the invention optionally further includes at least one other performance additive.
  • the other performance additives include dispersants, metal deactivators, detergents, viscosity modifiers, extreme pressure agents (typically boron- and/or sulfur- and/or phosphorus- containing), antiwear agents, antioxidants (such as hindered phenols, aminic antioxidants or molybdenum compounds), corrosion inhibitors, foam inhibitors, demulsifiers, pour point depressants, seal swelling agents, friction modifiers and mixtures thereof.
  • the total combined amount of the other performance additives (excluding the viscosity modifiers) present on an oil free basis may include ranges of ⁇ 0 % by weight to ⁇ 25 % by weight, or > 0.01 % by weight to ⁇ 20 % by weight, or > 0.1 % by weight to ⁇ 15 % by weight or > 0.5 % by weight to ⁇ 10 % by weight, or > 1 to ⁇ 5 % by weight of the composition.
  • the other performance additives may be present, it is common for the other performance additives to be present in different amounts relative to each other.
  • the lubricating oil composition further includes one or more viscosity modifiers.
  • Viscosity modifiers include (a) polymethacrylates, (b) esterified copolymers of (II) a vinyl aromatic monomer and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, (c) esterified interpolymers of (II) an alpha-olefin; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, or (d) hydrogenated copolymers of styrene-butadiene, (e) eth- ylene- propylene copolymers, (f) polyisobutenes, (g) hydrogenated styrene-isoprene polymers, (h) hydrogenated isoprene polymers, or (II) mixtures thereof.
  • the viscosity modifier includes (a) a polymethacrylate, (b) an esterified copolymer of (II) a vinyl aromatic monomer; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, (c) an esterified interpolymer of (II) an alpha-olefin; and (ii) an unsaturated carboxylic acid, anhydride, or derivatives thereof, or (d) mixtures thereof.
  • Viscosity modifier are preferably present in the lubricating oil composition in an amount of 0.01 to 8.0 % by weight, more preferably in an amount of 0.01 to 4.0 % by weight.
  • Extreme pressure agents include compounds containing boron and/or sulfur and/or phospho- rus.
  • the extreme pressure agent may be present in the lubricating oil composition at 0 % by weight to 20 % by weight, or 0.05 % by weight to 10 % by weight, or 0.1 % by weight to 8 % by weight of the lubricating oil composition.
  • the extreme pressure agent is a sulfur-containing compound.
  • the sulfur-containing compound may be a sulfurised olefin, a polysulfide, or mixtures thereof.
  • the sulfurised olefin include a sulfurised olefin derived from propylene, isobutylene, pentene; an organic sulfide and/or polysulfide including benzyldisulfide; bis- (chlorobenzyl) disulfide; dibutyl tetrasulfide; di-tertiary butyl polysulfide; and sulfurised methyl ester of oleic acid, a sulfurised alkylphenol, a sulfurised dipentene, a sulfurised terpene, a sulfurised Diels-Alder adduct, an alkyl sulphenyl N'N- dialkyl dithiocarbamates; or mixtures thereof.
  • the sulfurised olefin includes a sulfurised alkyl
  • the extreme pressure agent sulfur-containing compound includes a dimer- captothiadiazole or derivative, or mixtures thereof.
  • dimercaptothiadiazole include compounds such as 2,5-dimercapto-1 ,3,4-thiadiazole or a hydrocarbyl-substituted 2,5-dimercapto-1 ,3,4-thiadiazole, or oligomers thereof.
  • the oligomers of hydrocarbyl- substituted 2,5-dimercapto-1 ,3,4-thiadiazole typically form by forming a sulfur-sulfur bond between 2, 5-dimercapto-1 ,3,4-thiadiazole units to form derivatives or oligomers of two or more of said thiadiazole units.
  • Suitable 2, 5-dimercapto-1 ,3,4-thiadiazole derived compounds include for example 2, 5-bis(tert-nonyldithio)-1 ,3,4-thiadiazole or 2-tert-nonyldithio-5-mercapto-1 ,3,4- thiadiazole.
  • the number of carbon atoms on the hydrocarbyl substituents of the hydrocarbyl- substituted 2,5-dimercapto-1 ,3,4-thiadiazole typically include 1 to 30, or 2 to 20, or 3 to 16.
  • the dimercaptothiadiazole may be a thiadiazole-functionalised dispersant.
  • a detailed description of the thiadiazole- functionalised dispersant is described is paragraphs [0028] to [0052] of International Publication WO 2008/014315.
  • the thiadiazole-functionalised dispersant may be prepared by a method including heating, reacting or complexing a thiadiazole compound with a dispersant substrate.
  • the thiadiazole compound may be covalently bonded, salted, complexed or otherwise solubilised with a dispersant, or mixtures thereof.
  • the relative amounts of the dispersant substrate and the thiadiazole used to prepare the thiadiazole-functionalised dispersant may vary. In one embodiment the thiadiazole compound is present at 0.1 to 10 parts by weight relative to 100 parts by weight of the dispersant substrate. In different embodiments the thiadiazole compound is present at greater than 0.1 to 9, or greater than 0.1 to less than 5, or 0.2 to less than 5: to 100 parts by weight of the dispersant substrate.
  • the relative amounts of the thiadiazole compound to the dispersant substrate may also be expressed as (0.1 -10):100, or (>0.1 -9):100, (such as (>0.5-9):100), or (0.1 to less than 5): 100, or (0.2 to less than 5): 100.
  • the dispersant substrate is present at 0.1 to 10 parts by weight relative to 1 part by weight of the thiadiazole compound. In different embodiments the dispersant substrate is present at greater than 0.1 to 9, or greater than 0.1 to less than 5, or about 0.2 to less than 5: to 1 part by weight of the thiadiazole compound.
  • the relative amounts of the dispersant substrate to the thiadiazole compound may also be expressed as (0.1 -10): 1 , or (>0.1 -9):1 , (such as (>0.5-9):1 ), or (0.1 to less than 5): 1 , or (0.2 to less than 5): 1.
  • the thiadiazole-functionalised dispersant may be derived from a substrate that includes a suc- cinimide dispersant (for example, N-substituted long chain alkenyl succinimides, typically a pol- yisobutylene succinimide), a Mannich dispersant, an ester-containing dispersant, a condensation product of a fatty hydrocarbyl monocarboxylic acylating agent with an amine or ammonia, an alkyl amino phenol dispersant, a hydrocarbyl-amine dispersant, a polyether dispersant, a polyetheramine dispersant, a viscosity modifier containing dispersant functionality (for example polymeric viscosity index modifiers (VMs) containing dispersant functionality), or mixtures thereof.
  • the dispersant substrate includes a succinimide dispersant, an ester-containing dispersant or a Mannich dispersant.
  • the extreme pressure agent includes a boron- containing compound.
  • the boron-containing compound includes a borate ester (which in some embodiments may also be referred to as a borated epoxide), a borated alcohol, a borated dispersant, a borated phospho- lipid or mixtures thereof.
  • the boron-containing compound may be a borate ester or a borated alcohol.
  • the borate ester may be prepared by the reaction of a boron compound and at least one compound selected from epoxy compounds, halohydrin compounds, epihalohydrin compounds, alcohols and mixtures thereof.
  • the alcohols include dihydric alcohols, trihydric alcohols or higher alcohols, with the proviso for one embodiment that hydroxyl groups are on adjacent carbon atoms, i.e., vicinal.
  • Boron compounds suitable for preparing the borate ester include the various forms selected from the group consisting of boric acid (including metaboric acid, orthoboric acid and tetraboric acid), boric oxide, boron trioxide and alkyl borates.
  • the borate ester may also be prepared from boron halides.
  • suitable borate ester compounds include tripropyl borate, tributyl borate, tripentyl borate, trihexyl borate, triheptyl borate, trioctyl borate, trinonyl borate and tridecyl borate.
  • the borate ester compounds include tributyl borate, tri-2-ethylhexyl borate or mixtures thereof.
  • the boron-containing compound is a borated dispersant, typically derived from an N-substituted long chain alkenyl succinimide.
  • the borated dispersant includes a polyisobutylene succinimide. Borated dispersants are described in more detail in US Patents 3,087,936; and Patent 3,254,025.
  • the borated dispersant may be used m combination with a sulfur- containing compound or a borate ester.
  • the extreme pressure agent is other than a borated dispersant.
  • the number average molecular weight of the hydrocarbon from which the long chain alkenyl group was derived includes ranges of 350 to 5000, or 500 to 3000, or 550 to 1500.
  • the long chain alkenyl group may have a number average molecular weight of 550, or 750, or 950 to 1000.
  • the N-substituted long chain alkenyl succinimides are borated using a variety of agents including boric acid (for example, metaboric acid, orthoboric acid and tetraboric acid), boric oxide, boron trioxide, and alkyl borates.
  • boric acid for example, metaboric acid, orthoboric acid and tetraboric acid
  • boric oxide for example, boron trioxide
  • alkyl borates alkyl borates.
  • the borating agent is boric acid which may be used alone or in combination with other borating agents.
  • the borated dispersant may be prepared by blending the boron compound and the N- substituted long chain alkenyl succinimides and heating them at a suitable temperature, such as, 80 °C to 250 °C, or 90 °C to 230 °C, or 100 °C to 210 °C, until the desired reaction has oc- curred.
  • the molar ratio of the boron compounds to the N-substituted long chain alkenyl succinimides may have ranges including 10:1 to 1 :4, or 4:1 to 1 :3; or the molar ratio of the boron compounds to the N-substituted long chain alkenyl succinimides may be 1 :2.
  • the ratio of moles B : moles N (that is, atoms of B : atoms of N) in the borated dispersant may be 0.25:1 to 10:1 or 0.33:1 to 4:1 or 0.2:1 to 1 .5:1 , or 0.25:1 to 1 .3:1 or 0.8:1 to 1 .2:1 or about 0.5:1
  • An inert liquid may be used in performing the reaction.
  • the liquid may include toluene, xylene, chlorobenzene, dimethylformamide or mixtures thereof.
  • the lubricating oil composition further includes a borated phospholipid.
  • the borated phospholipid may be derived from boronation of a phospholipid (for example borona- tion may be carried out with boric acid).
  • Phospholipids and lecithins are described in detail in Encyclopedia of Chemical Technology, Kirk and Othmer, 3rd Edition, in “Fats and Fatty Oils", Volume 9, pages 795-831 and in “Lecithins", Volume 14, pages 250-269.
  • the phospholipid may be any lipid containing a phosphoric acid, such as lecithin or cephalin, or derivatives thereof.
  • phospholipids include phosphatidylcholine, phosphatidylser- ine, phosphatidylinositol, phosphatidylethanolamine, phosphotidic acid and mixtures thereof.
  • the phospholipids may be glycerophospholipids, glycerol derivatives of the above list of phospholipids. Typically, the glycerophospholipids have one or two acyl, alkyl or alkenyl groups on a glycerol residue.
  • the alkyl or alkenyl groups may contain 8 to 30, or 8 to 25, or 12 to 24 carbon atoms.
  • suitable alkyl or alkenyl groups include octyl, dodecyl, hexadecyl, octade- cyl, docosanyl, octenyl, dodecenyl, hexadecenyl and octadecenyl.
  • Phospholipids may be prepared synthetically or derived from natural sources. Synthetic phospholipids may be prepared by methods known to those in the art. Naturally derived phospholipids are often extracted by procedures known to those in the art. Phospholipids may be derived from animal or vegetable sources. A useful phospholipid is derived from sunflower seeds. The phospholipid typically contains 35 % to 60 % phosphatidylcholine, 20 % to 35 % phosphatidyl- inositol, 1 % to 25 % phosphatidic acid, and 10 % to 25 % phosphatidylethanolamine, wherein the percentages are by weight based on the total phospholipids.
  • the fatty acid content may be 20 % by weight to 30 % by weight palmitic acid, 2 % by weight to 10 % by weight stearic acid, 15 % by weight to 25 % by weight oleic acid, and 40 % by weight to 55 % by weight linoleic acid.
  • the lubricating oil composition contains a friction modifier.
  • a friction modifier is any material or materials that can alter the coefficient of friction of a surface lubricated by any lubricant or fluid containing such material(s). Friction modifiers, also known as fric- tion reducers, or lubricity agents or oiliness agents, and other such agents that change the ability of base oils, formulated lubricant compositions, or functional fluids, to modify the coefficient of friction of a lubricated surface may be effectively used in combination with the base oils or lubricant compositions of the present invention if desired. Friction modifiers may include metal- containing compounds or materials as well as ashless compounds or materials, or mixtures thereof.
  • Metal-containing friction modifiers may include metal salts or metal-ligand complexes where the metals may include alkali, alkaline earth, or transition group metals. Such metal- containing friction modifiers may also have low-ash characteristics. Transition metals may include Mo, Sb, Sn, Fe, Cu, Zn, and others.
  • Ligands may include hydrocarbyl derivative of alcohols, polyols, glycerols, partial ester glycerols, thiols, carboxylates, carbamates, thiocarba- mates, dithiocarbamates, phosphates, thiophosphates, dithiophosphates, amides, imides, amines, thiazoles, thiadiazoles, dithiazoles, diazoles, triazoles, and other polar molecular functional groups containing effective amounts of O, N, S, or P, individually or in combination.
  • Mo-containing compounds can be particularly effective such as for example Mo- dithiocarbamates, Mo(DTC),
  • Mo-dithiophosphates Mo(DTP), Mo-amines, Mo (Am), Mo-alcoholates, Mo- alcohol-amides, etc.
  • Ashless friction modifiers may have also include lubricant materials that contain effective amounts of polar groups, for example, hydroxyl-containing hydrocarbyl base oils, glycerides, partial glycerides, glyceride derivatives, and the like.
  • Polar groups in friction modifiers may include hydrocarbyl groups containing effective amounts of O, N, S, or P, individually or in com- bination.
  • Other friction modifiers that may be particularly effective include, for example, salts (both ash-containing and ashless derivatives) of fatty acids, fatty alcohols, fatty amides, fatty esters, hydroxyl-containing carboxylates, and comparable synthetic long-chain hydrocarbyl acids, alcohols, amides, esters, hydroxy carboxylates, and the like.
  • fatty organic acids, fatty amines, and sulfurized fatty acids may be used as suitable friction modifiers.
  • the lubricating oil composition may contain phosphorus- or sulfur- containing antiwear agents other than compounds described as an extreme pressure agent of the amine salt of a phosphoric acid ester described above.
  • antiwear agent may include a non-ionic phosphorus compound (typically compounds having phosphorus atoms with an oxidation state of +3 or +5), a metal dialkyldithiophosphate (typically zinc dialkyldithiophos- phates), amine dithiophosphate, ashless dithiophosphates and a metal mono- or di- alkylphosphate (typically zinc phosphates), or mixtures thereof.
  • the non-ionic phosphorus compound includes a phosphite ester, a phosphate ester, or mix- tures thereof.
  • the lubricating oil composition of the invention further includes at least one antioxidant.
  • Antioxidants retard the oxidative degradation of base stocks during service. Such degradation may result in deposits on metal surfaces, the presence of sludge, or a viscosity increase in the lubricant.
  • One skilled in the art knows a wide variety of oxidation inhibitors that are useful in lubricating oil compositions.
  • Useful antioxidants include hindered phenols. These phenolic antioxidants may be ashless (metal-free) phenolic compounds or neutral or basic metal salts of certain phenolic com- pounds. Typical phenolic antioxidant compounds are the hindered phenolics which are the ones which contain a sterically hindered hydroxyl group, and these include those derivatives of dihydroxy aryl compounds in which the hydroxyl groups are in the o- or p-position to each other. Typical phenolic antioxidants include the hindered phenols substituted with Ce+ alkyl groups and the alkylene coupled derivatives of these hindered phenols.
  • phenolic materials of this type 2-t-butyl-4-heptyl phenol; 2-t-butyl-4-octyl phenol; 2-t-butyl-4- dodecyl phenol; 2,6-di-t-butyl-4-heptyl phenol; 2,6-di-t-butyl-4-dodecyl phenol; 2-methyl-6- t-butyl-4-heptyl phenol; and 2-methyl-6-t-butyl-4-dodecyl phenol.
  • Other useful hindered mono-phenolic antioxidants may include for example hindered 2,6-di-alkyl- phenolic propionic ester derivatives.
  • Bis-phenolic antioxidants may also be advantageously used in combination with the instant invention.
  • ortho-coupled phenols include: 2,2'-bis(4- heptyl-6-t-butyl-phenol); 2,2'-bis(4- octyl-6-t-butyl-phenol); and 2,2'-bis(4-dodecyl-6-t-butyl- phenol).
  • Para-coupled bisphenols include for example 4,4'-bis(2,6-di-t-butyl phenol) and 4,4'- methylene-bis(2,6-di-t-butyl phenol).
  • Non-phenolic oxidation inhibitors which may be used include aromatic amine antioxidants and these may be used either as such or in combination with phenolics.
  • Typical examples of non- phenolic antioxidants include: alkylated and non-alkylated aromatic amines such as aromatic monoamines of the formula R 8 R 9 R 10 N, where R 8 is an aliphatic, aromatic or substituted aromatic group, R 9 is an aromatic or a substituted aromatic group, and R 10 is H, alkyl, aryl or R 11 S(0)xR 12 , where R 11 is an alkylene, alkenylene, or aralkylene group, R 12 is a higher alkyl group, or an alkenyl, aryl, or alkaryl group, and x is 0, 1 or 2.
  • the aliphatic group R 8 may con- tain from 1 to about 20 carbon atoms, and preferably contains from about 6 to 12 carbon atoms.
  • the aliphatic group is a saturated aliphatic group.
  • both R 8 and R 9 are aromatic or substituted aromatic groups, and the aromatic group may be a fused ring aromatic group such as naphthyl.
  • Aromatic groups R 8 and R 9 may be joined together with other groups such as S.
  • Typical aromatic amines antioxidants have alkyl substituent groups of at least about 6 carbon atoms.
  • Examples of aliphatic groups include hexyl, heptyl, octyl, nonyl, and decyl. Generally, the aliphatic groups will not contain more than about 14 carbon atoms.
  • the general types of amine antioxidants useful in the present compositions include diphenylamines, phenyl naph- thylamines, phenothiazines, imidodibenzyls and diphenyl phenylene diamines. Mixtures of two or more aromatic amines are also useful. Polymeric amine antioxidants can also be used.
  • aromatic amine antioxidants useful in the present invention include: ⁇ , ⁇ '-dioctyldiphenylamine; t-octylphenyl-alpha-naphthylamine; phenyl-alphanaphthylamine; and p-octylphenyl-alpha-naphthylamine.
  • Sulfurized alkyl phenols and alkali or alkaline earth metal salts thereof also are useful antioxidants.
  • the lubricating oil composition of the invention further includes a dispersant.
  • the dispersant may be a succinimide dispersant (for example N-substituted long chain alkenyl succinimides), a Mannich dispersant, an ester-containing dispersant, a condensation product of a fatty hydrocarbyl monocarboxylic acylating agent with an amine or ammonia, an alkyl amino phenol dispersant, a hydrocarbyl-amine dispersant, a polyether dispersant or a polyetheramine dispersant.
  • succinimide dispersant for example N-substituted long chain alkenyl succinimides
  • Mannich dispersant for example N-substituted long chain alkenyl succinimides
  • an ester-containing dispersant for example N-substituted long chain alkenyl succinimides
  • the succinimide dispersant includes a polyisobutylene-substituted succin- imide, wherein the polyisobutylene from which the dispersant is derived may have a number average molecular weight of 400 to 5000, or 950 to 1600.
  • Succinimide dispersants and their methods of preparation are more fully described in U.S. Patents 4,234,435 and 3,172,892.
  • Suitable ester-containing dispersants are typically high molecular weight esters. These materials are described in more detail in U.S. Patent 3,381 ,022.
  • the dispersant includes a borated dispersant.
  • the borated dispersant includes a succinimide dispersant including a polyisobutylene succinimide, wherein the polyisobutylene from which the dispersant is derived may have a number average molecular weight of 400 to 5000. Borated dispersants are described in more detail above within the ex- treme pressure agent description.
  • Dispersant viscosity modifiers include functionalised polyolefins, for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine, a polymethacrylate functionalised with an amine, or es- terified styrene- maleic anhydride copolymers reacted with an amine may also be used in the composition of the invention.
  • functionalised polyolefins for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine, a polymethacrylate functionalised with an amine, or es- terified styrene- maleic anhydride copolymers reacted with an amine may also be used in the composition of the invention.
  • Corrosion inhibitors which are necessary components ofthe present invention can be described as any materials (additives, functionalized fluids, etc.) that form a protective film on a surface that prevents corrosion agents from reacting or attacking that surface with a resulting loss of surface material.
  • Protective films may be absorbed on the surface or chemically bonded to the surface.
  • Protective films may be constituted from mono-molecular species, oligo- meric species, polymeric species, or mixtures thereof.
  • Protective films may derive from the intact corrosion inhibitors, from their combination products, or their degradation products, or mixtures thereof.
  • Surfaces that may benefit from the action of corrosion inhibitors may include metals and their alloys (both ferrous and non-ferrous types) and non-metals.
  • Corrosion inhibitors may include various oxygen-, nitrogen-, sulfur-, and phosphorus- containing materials, and may include metal-containing compounds (salts, organometallics, etc.) and nonmetal-containing or ashless materials.
  • Corrosion inhibitors may include, but are not limited to, additive types such as, for example, hydrocarbyl-, aryl-, alkyl-, arylalkyl-, and alkylaryl- versions of detergents (neutral, overbased), sulfonates, phenates, salicylates, alco- holates, carboxylates, salixarates, phosphites, phosphates, thiophosphates, amines, amine salts, amine phosphoric acid salts, amine sulfonic acid salts, alkoxylated amines, etheramines, polyetheramines, amides, imides, azoles, diazoles, triazoles, benzotriazoles, benzothi
  • Corrosion inhibitors are used to reduce the degradation of metallic parts that are in contact with the lubricating oil composition.
  • Suitable corrosion inhibitors include thiadiazoles.
  • Aromatic triazoles, such as tolyltriazole are suitable corrosion inhibitors for non-ferrous metals, such as copper.
  • Metal deactivators include derivatives of benzotriazoles (typically tolyltriazole), 1 ,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles, thiadiazoles or 2-alkyldithiobenzothiazoles.
  • Foam inhibitors may advantageously be added to the lubricating oil composition. These agents retard the formation of stable foams. Silicones and organic polymers are typical foam inhibitors. For example, polysiloxanes, such as silicon oil, or polydimethyl siloxane, provide foam inhibiting properties. Further foam inhibitors include copolymers of ethyl acrylate and 2- ethylhexyl acrylate and optionally vinyl acetate.
  • Demulsifiers include trialkyi phosphates, and various polymers and copolymers of ethylene glycol, ethylene oxide, propylene oxide, or mixtures thereof.
  • pour point depressants including esters of maleic anhydride-styrene, polymethacrylates, poly- acrylates or polyacrylamides.
  • Seal compatibility agents help to swell elastomeric seals by causing a chemical reaction in the fluid or physical change in the elastomer.
  • Suitable seal compatibility agents for lubricating oils include organic phosphates, aromatic esters, aromatic hydrocarbons, esters (butylbenzyl phthalate, for example), and polybutenyl succinic anhydride.
  • Such additives may preferably be used in an amount of 0.01 to 3 % by weight, more preferably 0.01 to 2 % by weight.
  • the presently claimed invention is directed to a lubricating oil composition
  • a lubricating oil composition comprising a) ⁇ 10 ppm to ⁇ 10 000 ppm a compound of general formula (I) as defined in one
  • mineral oils Group I, II or III oils
  • polyalphaolefins Group IV oils
  • polymer- ized and interpolymerized olefins alkyl naphthalenes
  • alkylene oxide polymers silicone oils
  • silicone oils phosphate esters and carboxylic acid esters
  • one or more performance additives selected from the group consisting of dispersants, metal deactivators, detergents, viscosity modifiers, extreme pressure agents (typically boron- and/or sulfur- and/or phosphorus- containing), antiwear agents, antioxidants (such as hindered phenols, aminic antioxidants or molybdenum compounds), corrosion inhibitors, foam inhibitors, demulsifiers, pour point depressants, seal swelling agents and friction modifiers, whereby the % by weight of the components a), b) and c) is in each case related to the overall weight of the lubricating oil composition and the sum of the weight of all components a), b) and c) adds up to 100 %.
  • one or more performance additives selected from the group consisting of dispersants, metal deactivators, detergents, viscosity modifiers, extreme pressure agents (typically boron- and/or sulfur- and/or phosphorus- containing), antiwear agents, antioxidants (such as hindered phenols,
  • the presently claimed invention is directed to a lubricating oil composition
  • a lubricating oil composition comprising
  • At least one base stock selected from the group consisting of mineral oils (Group I, II or III oils), polyalphaolefins (Group IV oils), polymerized and interpolymerized olefins, alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters (Group V oils), and
  • % by weight of one or more performance additives selected from the group consisting of dispersants, metal deactivators, detergents, viscosity modifiers, extreme pressure agents (typically boron- and/or sulfur- and/or phosphorus- containing), antiwear agents, antioxidants (such as hindered phenols, aminic antioxidants or molybdenum compounds), corrosion inhibitors, foam inhibitors, demulsifiers, pour point depressants, seal swelling agents and friction modifiers, whereby the % by weight of the components a), b) and c) is in each case related to the overall weight of the lubricating oil composition and the sum of the weight of all components a), b) and c) adds up to 100 %.
  • one or more performance additives selected from the group consisting of dispersants, metal deactivators, detergents, viscosity modifiers, extreme pressure agents (typically boron- and/or sulfur- and/or phosphorus- containing), antiwear agents, antioxidants (such as hindered
  • the lubricating oil compositions comprising at least one compound of general formula (I) as defined above can be used for various applications such as light, medium and heavy duty engine oils, industrial engine oils, marine engine oils, automotive engine oils, crankshaft oils, compressor oils, refrigerator oils, hydrocarbon compressor oils, very low-temperature lubricating oils and fats, high temperature lubricating oils and fats, wire rope lubricants, textile machine oils, refrigerator oils, aviation and aerospace lubricants, aviation turbine oils, transmission oils, gas turbine oils, spindle oils, spin oils, traction fluids, transmission oils, plastic transmission oils, passenger car transmission oils, truck transmission oils, industrial transmission oils, industrial gear oils, insulating oils, instrument oils, brake fluids, transmission liquids, shock absorber oils, heat distribution medium oils, transformer oils, fats, chain oils, minimum quantity lubricants for metalworking operations, oil to the warm and cold working, oil for neat oil metalworking fluids, oil for semi-synthetic metalworking fluids, oil for synthetic metalworking fluids, drilling detergents for the soil exploration
  • the lubricating oil composition is preferably in contact with at least one metal selected from the group consisting of copper, aluminum, zinc, magnesium, nickel, titanium, lead, cobalt and tin, more preferably with copper.
  • the aforementioned metals may also be present in the form of mixtures containing one or more of the aforementioned metals, i.e. the aforementioned metals can also be present in the form of their alloys.
  • R1 denotes hydrogen or branched or straight-chain and unsubstituted or at least
  • a metal selected from the group consisting of copper, aluminum, zinc, magnesium, nickel, titanium, lead, cobalt and tin in a lubricating oil composition.
  • corrosion is defined as a phenomenon such that a metal is eroded in a chemical or electrochemical manner by an environmental substance surrounding it, for example reactive species containing oxygen or sulfur, or the metal is de- graded in the lubricating oil composition.
  • copper can be eroded to CuO, CU2O, CuS and Cu 2 S.
  • the presently claimed invention is directed to a method for enhancing the corrosion resistance of a metal selected from the group consisting of copper, aluminum, zinc, magnesium, nickel, titanium, lead, cobalt and tin in a lubricating oil composition comprising the addition of a compound of general formula (I)
  • R1 denotes hydrogen or branched or straight-chain and unsubstituted or at least
  • the metal corrosion test is a modified ASTM D130 copper corrosion test, the ASTM visual rating being outlined in Table A.
  • the test is designed to measure the corrosiveness to copper in the presence of hydrocarbons.
  • a clean, dry copper strip is placed in 30 mL test solution comprising example formulations A to G as described below in accordance with the invention and heated for 3 hours at 100°C. Any sulfur that is present is added as pure sulfur (Ss). Results are determined by comparison with the ASTM Copper Strip Corrosion Standards and giving the appropriate classification.

Abstract

La présente invention concerne une composition d'huile lubrifiante comprenant du 1,8- diazabicyclo-5,4,0-undecène-7, au moins une huile de base et un ou plusieurs additifs de rendement; l'utilisation de 1,8- diazabicyclo-5,4,0-undecène-7 pour prévenir la corrosion dans la composition d'huile lubrifiante et un procédé pour améliorer la résistance à la corrosion d'une formulation d'huile lubrifiante comprenant l'ajout de 1,8- diazabicyclo-5,4,0-undecène-7.
PCT/EP2014/065386 2013-07-29 2014-07-17 Composition d'huile lubrifiante ayant une meilleure résistance à la corrosion WO2015014629A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP13178383 2013-07-29
EP13178383.9 2013-07-29

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WO2015014629A1 true WO2015014629A1 (fr) 2015-02-05

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110157527A (zh) * 2018-02-11 2019-08-23 中国海洋石油集团有限公司 一种柴油机油

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1257978A (fr) * 1968-08-06 1971-12-22
JP2001254091A (ja) * 2000-03-09 2001-09-18 Sanyo Chem Ind Ltd ブレーキ液用組成物
JP2011149019A (ja) * 2009-12-25 2011-08-04 Sanyo Chem Ind Ltd シリコンインゴット用水性切削液

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1257978A (fr) * 1968-08-06 1971-12-22
JP2001254091A (ja) * 2000-03-09 2001-09-18 Sanyo Chem Ind Ltd ブレーキ液用組成物
JP2011149019A (ja) * 2009-12-25 2011-08-04 Sanyo Chem Ind Ltd シリコンインゴット用水性切削液

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110157527A (zh) * 2018-02-11 2019-08-23 中国海洋石油集团有限公司 一种柴油机油

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