EP2937408B1 - Composition lubrifiante comprenant un ester de mélange d'alcools en C17 - Google Patents

Composition lubrifiante comprenant un ester de mélange d'alcools en C17 Download PDF

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Publication number
EP2937408B1
EP2937408B1 EP14165470.7A EP14165470A EP2937408B1 EP 2937408 B1 EP2937408 B1 EP 2937408B1 EP 14165470 A EP14165470 A EP 14165470A EP 2937408 B1 EP2937408 B1 EP 2937408B1
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EP
European Patent Office
Prior art keywords
oil
component
acid
lubricant composition
lubricant
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Not-in-force
Application number
EP14165470.7A
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German (de)
English (en)
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EP2937408A1 (fr
Inventor
Dr. Markus SCHERER
Dr. Boris BREITSCHEIDEL
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BASF SE
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BASF SE
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Priority to ES14165470.7T priority Critical patent/ES2620009T3/es
Priority to EP14165470.7A priority patent/EP2937408B1/fr
Publication of EP2937408A1 publication Critical patent/EP2937408A1/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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/36—Esters of polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/72—Esters of polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—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
    • C10M2205/028—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
    • 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
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    • 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
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    • 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
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
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    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/081—Biodegradable compounds
    • 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
    • C10N2030/02—Pour-point; Viscosity index
    • 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
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    • 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
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    • 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
    • C10N2030/36—Seal compatibility, e.g. with rubber
    • 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
    • C10N2030/62—Food grade properties
    • C—CHEMISTRY; METALLURGY
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/66—Hydrolytic stability
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/243—Cold working
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
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    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
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    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
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    • C10N2040/30—Refrigerators lubricants or compressors lubricants
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    • C10N2040/32—Wires, ropes or cables lubricants
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    • C10N2040/36—Release agents or mold release agents
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/46—Textile oils

Definitions

  • the present invention relates to the field of lubricant compositions.
  • the present invention relates to a lubricant composition
  • a lubricant composition comprising an ester component derived from (a) an alcohol component, which is a C 17 alcohol mixture having an average iso-index of 2.8 to 3.7 and (b) an acid component, which is an aliphatic C 4 -C 10 dicarboxylic acid or cyclohexanedicarboxylic acid.
  • the invention relates to the use of the above ester component for improving the seal compatibility of lubricant compositions.
  • the lubricant compositions can be used in a variety of different formulations required in motor vehicles.
  • lubricant compositions are based on a multitude of different natural or synthetic components. The resulting properties of the various existing lubricant compositions are tailored to the specific technical requirements by the addition of further components and selected combinations thereof. In this way, lubricant compositions are obtained which can fulfill the complex requirements associated with the various special technical applications in the field of motor vehicles, automotive engines and other machinery.
  • lubricant compositions are needed that provide highest shear stability, improved low-temperature viscosity, minimum degree of evaporation loss, good fuel efficiency, acceptable seal compatibility and excellent wear protection.
  • PAO polyalphaolefin
  • PIB polyisobutenes
  • OCPs oligomeric co-polymers
  • PMAs polymethacrylates
  • high viscosity esters complex esters
  • US 5451630 further suggests oligomeric copolymers which are demonstrated to provide good shear stability to lubricant compositions.
  • lubricant compositions including a variety of different thickening agents like PIBs, OCPs, PMAs and high viscosity esters which have been demonstrated to be useful as viscosity index improvers.
  • low viscosity esters like DIDA (diisodecyl adipate), DITA (diisotridecyl adipate) or TMTC (trimethyllolpropane caprylate) have also been added to lubricant compositions as solubilizers for polar additive types while further providing lubricity and seal compatibility.
  • DIDA diisodecyl adipate
  • DITA diisotridecyl adipate
  • TMTC trimethyllolpropane caprylate
  • ester component for lubricants providing a good balance of thermal stability, low temperature viscosity, hydrolysis stability and seal compatibility.
  • Ester components should ideally have a kinematic viscosity around 46 mm 2 /s, which is typical for hydraulic liquids.
  • Current hydraulic liquids are normally formulated with ester components of lower viscosity and are then adjusted to the required viscosity using thickeners resulting in disadvantageous low temperature viscosities as well as higher complexity in formulating the lubricant compositions.
  • esters of dicarboxylic acids with 2-propylheptanol which provide good thermal stability, hydrolysis stability and low viscosity at low temperature.
  • these ester disadvantageously show a low seal compatibility.
  • An alternative approach is to employ diesters of so-called Guerbet alcohols or mixtures thereof.
  • the trivial name of Guerbet alcohol is used for 2-alkyl-substituted 1-alkanols whose industrial synthesis is described inter alia in H. Machemer, Angewandte Chemie, Vol. 64, pages 213-220 (1952 ) and in G. Dieckelmann and H.J. Heinz in "The Basics of Industrial Oleochemistry", pages 145-145 (1988 ).
  • Guerbet diesters show a favorable seal compatibility, they have a kinematic viscosity significantly below the desired value of 46 mm 2 /s.
  • lubricant compositions including an ester component having a kinematic viscosity in the typical range of hydraulic fluids even without the additional use of thickeners and at the same time providing high seal compatibility, good hydrolysis or oxidation stability, favorable low temperature viscosity and a low pour point.
  • the present invention relates to a lubricant composition
  • a lubricant composition comprising an ester component derived from (a) an alcohol component, which is a C 17 alcohol mixture having an average iso-index of 2.8 to 3.7 and (b) an acid component, which is an aliphatic C 4 -C 10 dicarboxylic acid or cyclohexanedicarboxylic acid.
  • the lubricant composition according to the present invention comprises the ester component derived from an alcohol component additionally comprising a polyol.
  • the polyol may be selected e.g. from trimethylol propane, neopentyl glycol, pentaerythrit or dipentaerythrol.
  • the alcohol component is free from a polyol and essentially consists of the C 17 alcohol mixture having an average iso-index of 2.8 to 3.7.
  • the ester component in the inventive lubricant composition has a kinematic viscosity determined according to DIN 51562-1 at 40°C of 20 to 70 mm 2 /s. In a preferred embodiment, the ester component has a kinematic viscosity of 35 to 55 mm 2 /s, preferably 40 to 50 mm 2 /s. Most preferably, the ester component has a kinematic viscosity of about 46 mm 2 /s.
  • the C 17 alcohol mixture has an average iso-index of 2.9 to 3.6, preferably 3.01 to 3.5, more preferably 3.05 to 3.4.
  • examples the acid component include but are not limited to cyclohexane-1,2-dicarboxylic acid, cyclohexane-1,3-dicarboxylic acid or cyclohexane-1,4-dicarboxylic acid or an aliphatic dicarboxylic acid selected from glutaric acid, adipic acid, pimelic acid, azeleic, sebacic acid.
  • the acid component is derived from an aliphatic C 5 -C 7 dicarboxylic acid or cyclohexanedicarboxylic acid.
  • acids examples include cyclohexane-1,2-dicarboxylic acid, cyclohexane-1,3-dicarboxylic acid or cyclohexane-1,4-dicarboxylic acid or an aliphatic dicarboxylic acid selected from glutaric acid, adipic acid, pimelic acid, most preferably adipic acid.
  • the lubricant composition comprises the above ester component, a base oil component and optionally an additive component.
  • the lubricant composition comprises based on the total weight of the lubricant composition:
  • the lubricant composition comprises based on the total weight of the lubricant composition:
  • the additive component may be selected from the group consisting of antioxidants, dispersants, foam inhibitors, demulsifiers, seal swelling agents, friction reducers, anti-wear agents, detergents, corrosion inhibitors, extreme pressure agents, metal deactivators, rust inhibitors, pour point depressants and mixtures thereof.
  • the additive component includes antioxidants, corrosion inhibitors for nonferrous metals and steel, additives for modifying air separation behavior, foam behavior and demulsifying power and EP/AW additives.
  • the base oil component may be selected from the group consisting of a Group I mineral oil, a Group II mineral oil, a Group III mineral oil, a Group IV oil, a Group V oil, and mixtures thereof.
  • the base oil component comprises a polyalphaolefin (Group IV oil), more preferably a polyalphaolefin 4, polyalphaolefin 6 and/or polyalphaolefin 8, preferably a polyalphaolefin 6.
  • the lubricant composition comprises said ester component in an amount of 50 to 99 wt%, preferably 80 to 99 wt%, based on the total weight of the lubricant composition.
  • the lubricant composition comprises said base oil component in an amount of 0 to 30 wt%, preferably 0 to 19 wt%, based on the total weight of the lubricant composition.
  • the lubricant composition comprises said additive component in an amount of 0.1 to 20 wt%, preferably 1 to 20 wt%, based on the total weight of the lubricant composition.
  • the present invention also relates to the use of the ester component as defined above for improving the seal compatibility of lubricant compositions.
  • the lubricant composition shows a seal compatibility with nitrile-butadiene-copolymer determined according to ISO 1817 at 100°C for 168 hours resulting in a mass change of 20% or lower, preferably 10% or lower.
  • the lubricant composition shows a seal compatibility with nitrile-butadiene-copolymer determined according to ISO 1817 at 100°C for 168 hours resulting in a volume change of 30% or lower, preferably 15% or lower.
  • the lubricant composition shows a seal compatibility with nitrile-butadiene-copolymer determined according to ISO 1817 at 100°C for 168 hours resulting in a hardness change of 12% or lower, preferably 8% or lower.
  • the data regarding the mass change, volume change or hardness change is obtained from a comparison of the nitrile-butadiene-copolymer based seal before being subjected to the lubricant composition and after being exposed to the lubricant composition for 168 hours at 100°C.
  • the lubricant compositions and uses according to the invention may in one embodiment be implemented in the context of a light, medium and heavy duty engine oil, industrial engine oil, marine engine oil, automotive engine oil, crankshaft oil, compressor oil, refrigerator oil, hydrocarbon compressor oil, very low-temperature lubricating oil and fat, high temperature lubricating oil and fat, wire rope lubricant, textile machine oil, aviation and aerospace lubricant, aviation turbine oil, transmission oil, gas turbine oil, spindle oil, spin oil, traction fluid, plastic transmission oil, passenger car transmission oil, truck transmission oil, industrial transmission oil, industrial gear oil, insulating oil, instrument oil, brake fluid, transmission liquid, shock absorber oil, heat distribution medium oil, transformer oil, fat, chain oil, minimum quantity lubricant for metalworking operations, oil to the warm and cold working, oil for a water-based metalworking liquid, oil for a neat oil metalworking fluid, oil for a semi-synthetic metalworking fluid, oil for a synthetic metalworking fluid, drilling detergent for the soil exploration, hydraulic oil, bio
  • the invention relates to the use of the inventive lubricant as a hydraulic oil, especially a biohydraulic oil.
  • a biohydraulic oil in the sense of the present invention is a biodegradable hydraulic oil. This is determined, for example, by the standard OECD 301 test or by the EPA 560/6-82-003 test, and preferably by OECD test 301 B.
  • the biohydraulic oil shows a biological degradability of at least 60%, preferably at least 70% and, more particularly, at least 75%. This can be achieved according to the invention e.g. by employing the ester component in high amounts such as 80 to 99.9 wt% in addition to the additive component in amounts of 0.1 to 20 wt% in the absence of base oil component.
  • the lubricant compositions according to the present invention include the following components which are described below in more detail.
  • the lubricant composition of the present invention comprises an ester component derived from (a) an alcohol component, which is a C 17 alcohol mixture having an average iso-index of 2.8 to 3.7 and (b) an acid component, which is an aliphatic C 4 -C 10 dicarboxylic acid or cyclohexanedicarboxylic acid.
  • the alcohol component can be obtained as described in WO 2009/124979 . In one embodiment, the alcohol component is obtained by
  • the above C 17 alcohol component may be used in combination with one or more polyols.
  • Suitable polyols include e.g. trimethylol propane, neopentyl glycol, pentaerythrit, or dipentaerythrol.
  • the alcohol component includes up to 15 wt%, such as 10 wt% of polyol.
  • the alcohol component is free from a polyol and essentially consists of the C 17 alcohol mixture having an average iso-index of 2.8 to 3.7.
  • the C 17 alcohol mixture has an average iso-index of 2.9 to 3.6, more preferably 3.01 to 3.5, still more preferably 3.05 to 3.4, such as 3.1.
  • the acid component in the ester component of the inventive lubricant composition is derived from an aliphatic C 4 -C 10 dicarboxylic acid, preferably C 5 -C 7 dicarboxylic acid, or cyclohexanedicarboxylic acid.
  • the present inventors surprisingly have found that esters of such acids with the above C 17 alcohol component have a desired kinematic viscosity and high hydrolysis and oxidation stability and at the same time provide superior seal compatibility.
  • the cyclohexanedicarboxylic acid is cyclohexane-1,2-dicarboxylic acid, cyclohexane-1,3-dicarboxylic acid or cyclohexane-1,4-dicarboxylic acid.
  • the aliphatic dicarboxylic acid is selected from glutaric acid, adipic acid, pimelic acid, azeleic, sebacic acid. More preferably, the aliphatic dicarboxylic acid is selected from glutaric acid, adipic acid, and pimelic acid. Most preferably, the acid component is derived from adipic acid.
  • Esterification can be effected as well known in the art.
  • the acid component may be reacted with an excess of alcohol component at elevated temperature in the presence of a suitable catalyst. Water generated during esterification is continually removed. After completion of the reaction excess alcohol is separated from the ester and the product is dried and/ or purified as needed.
  • the kinematic viscosity of the resulting ester component at 40 °C is preferably from 20 to 70 mm 2 /s.
  • the ester component has a kinematic viscosity of 35 to 55 mm 2 /s, still more preferably 40 to 50 mm 2 /s.
  • the ester component has a kinematic viscosity of about 46 mm 2 /s.
  • the ester component is present in the inventive lubricant composition in an amount of preferably 5 to 99.9 wt%, more preferably 50 to 99 wt%, such as 80 to 99 wt%.
  • the lubricant composition of the present invention may also comprise a base oil component.
  • the lubricant composition comprises 0 to 75 wt%, preferably 0 to 19 wt% of a base oil component.
  • the base oil component may be included in higher amounts.
  • an alternative lubricant composition may comprise 20 to 80 wt%, preferably 40 to 60 wt% of base oil component.
  • Such alternative lubricant compositions may comprise the ester component in an amount of 5 to 29 wt%, preferably 5 to 20 wt%, and additive component in an amount of 1 to 50 wt%, preferably 10 to 45 wt%.
  • the lubricant compositions according to the present invention further comprise base oils 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 base oil (or base stock) to be used in the lubricant compositions according to the present invention is an inert, solvent-type oil component in the lubricant compositions according to the present invention.
  • the base oil component of the lubricant composition comprises a PAO and/or a group II and/or Group III mineral oil, preferably a PAO 4, PAO 6 and/or PAO 8, wherein a PAO 6 is especially preferred base oil.
  • Polyalphaolefins suitable for the lubricant compositions according to the present invention include known PAO materials which typically comprise relatively low molecular weight hydrogenated polymers or oligomers of alphaolefins which include but are not limited to C 2 to about C 32 alphaolefins with the C 8 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 C 14 to C 18 provide low viscosity base stocks.
  • PAO 6 refers to the class of polyalphaolefins which typically has viscosity in the range of 6 mm 2 /s at 100°C.
  • a variety of commercially available compositions are available for these specifications.
  • Low viscosity PAO fluids suitable for the lubricant compositions according to 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.
  • 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 (Larkin ); 4,910,355 (Shubkin ); 4,956,122 (Watts ); and 5,068,487 (Theriot ).
  • Carboxylic acid esters which are also widely considered in the literature to belong to the Group V base oils are not understood according to the present invention as base oils (base stocks) or even group V base oils but are separately listed as the ester component being essential to the present invention.
  • Synthetic base oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(1-hexenes), poly(1-octenes), poly(1-decenes)); alkylbenzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl)benzenes); polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenols); and alkylated diphenyl ethers and alkylated diphenyl sulfides and derivative, analogs and homologs thereof.
  • polymerized and interpolymerized olefins e.g., 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 base oils. These are exemplified by polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide, and the alkyl and aryl ethers of polyoxyalkylene polymers (e.g., methyl-polyiso-propylene glycol ether having a molecular weight of 1000 or diphenyl ether of polyethylene glycol having a molecular weight of 1000 to 1500); and mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C 3 -C 8 fatty acid esters and C 13 Oxo acid diester of tetraethylene glycol.
  • polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide
  • alkyl and aryl ethers of polyoxyalkylene polymers e.g., methyl-
  • Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy- or polyaryloxysilicone oils and silicate oils comprise another useful class of synthetic base oils; such base 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.
  • base oils include tetraethyl silicate, tetraisopropyl silicate, tetra-(2- ethylhexyl)silicate, tetra-(4-methyl-2-ethy
  • Other synthetic base oils include liquid esters of phosphorous-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid) and polymeric tetrahydrofurans.
  • the relative amount of base oil in the lubricant compositions according to the present invention is in the range of 0 to 75 wt%, preferably 0 to 19 wt%, based on the total amount of lubricant composition.
  • the lubricant composition according to the present invention may further comprise an additive component.
  • the additive component is selected from the list consisting of antioxidants, dispersants, foam inhibitors, demulsifiers, seal swelling agents, friction reducers, anti-wear agents, detergents, corrosion inhibitors, extreme pressure agents, metal deactivators, rust inhibitors, pour point depressants and mixtures thereof.
  • the additive component as used in the present invention also includes an additive package and/or performance additives.
  • the additive package as used in the present invention as well as the compounds relating to performance additives are considered mixtures of additives that are typically used in lubricant compositions in limited amounts for mechanically, physically or chemically stabilizing the lubricant compositions while special performance characteristics can be further established by the individual or combined presence of such selected additives.
  • Additive packages are separately defined in the present invention since a variety of such additive packages are commercially available and typically used in lubricant compositions.
  • One such preferred additive package that is commercially available is marketed under the name Anglamo16004J®.
  • the individual components contained in the additive packages and/or the compounds further defined in the present invention as so-called performance additives include a larger number of different types of additives including dispersants, metal deactivators, detergents, extreme pressure agents (typically boron- and/or sulfur- and/or phosphorus- containing), anti-wear 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 additive component as the sum of all additives contained in the lubricant compositions according to the present invention also including all additives contained in an additive package or added separately is present in the lubricant compositions of the present invention in an amount of 0.1 to 20 wt%, preferably 1 to 20 wt%, such as 2 to 15 wt%, and 3 to 12 wt%.
  • Extreme pressure agents include compounds containing boron and/or sulfur and/or phosphorus.
  • the extreme pressure agent may be present in the lubricant compositions at 0 % by weight to 15 % by weight, or 0.05 % by weight to 10 % by weight, or 0.1 % by weight to 8 % by weight of the lubricant 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 olefin derived from propylene, isobutylene, pentene or mixtures thereof.
  • the extreme pressure agent sulfur-containing compound includes a dimercaptothiadiazole 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 succinimide dispersant (for example, N-substituted long chain alkenyl succinimides, typically a polyisobutylene 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 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 phospholipid 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 in 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 Mn (GPC; kg/mol) 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 Mn 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 occurred.
  • 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 additive component in the lubricant composition according to the present invention further includes a borated phospholipid.
  • the borated phospholipid may be derived from boronation of a phospholipid (for example boronation 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, phosphatidylserine, phosphatidylinositol, phosphatidyl-ethanolamine, 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, octadecyl, 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 % phosphatidylinositol, 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 performance additive in the lubricant compositions according to the present invention may include 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 friction 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, thiocarbamates, 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), Modithiophosphates, Mo(DTP), Mo-amines, Mo (Am), Mo-alcoholates, Mo- alcohol-amides, and the like.
  • Ashless friction modifiers may 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 combination.
  • 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 performance additive in the lubricant compositions according to the present invention may include phosphorus- or sulfur- containing anti-wear agents other than compounds described as an extreme pressure agent of the amine salt of a phosphoric acid ester described above.
  • the anti-wear 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 dialkyldithiophosphates), 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 mixtures thereof.
  • the performance additive in the lubricant composition according to the present invention may further include 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 compounds. 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 C 6+ 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-butylphenol).
  • 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(O) x R 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 contain 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 naphthylamines, 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: p,p'-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 performance additive in the lubricant compositions according to the present 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 hydrocarbylamine 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 succinimide, 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 extreme pressure agent description.
  • Dispersant viscosity modifiers are considered additives in the context of the present invention due to their additional functionalisation and are therefore not considered viscosity improving agents according to the present invention.
  • 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 esterified styrene-maleic anhydride copolymers reacted with an amine.
  • corrosion inhibitors 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, oligomeric 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, alcoholates, 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, benzothiadoles,
  • Corrosion inhibitors are used to reduce the degradation of metallic parts that are in contact with the lubricant 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 also advantageously be added as a performance additive to the lubricant compositions according to the present invention. These agents retard the formation of stable foams. Silicones and organic polymers are typical foam inhibitors. For example, polysiloxanes, such as silicon oil, or polydimethylsiloxane, provide foam inhibiting properties. Further foam inhibitors include copolymers of ethyl acrylate and 2-ethylhexyl acrylate and optionally vinyl acetate.
  • Demulsifiers include trialkyl phosphates, and various polymers and copolymers of ethylene glycol, ethylene oxide, propylene oxide, or mixtures thereof.
  • esters of maleic anhydride-styrene, or polyacrylamides are included.
  • 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 lubricant compositions 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 of the total amount of the lubricant composition.
  • ester component derived from (a) an alcohol component, which is a C 17 alcohol mixture having an average iso-index of 2.8 to 3.7 and (b) an acid component, which is an aliphatic C 4 -C 10 , preferably C 5 -C 7 dicarboxylic acid or cyclohexanedicarboxylic acid for improving the seal compatibility of lubricant compositions.
  • Ester components are typically employed in lubricant compositions e.g. as a solubilizer or co-solvent for other components assisting in solubilization of polar additives and modifying rheological properties of the lubricant composition.
  • an ester component derived from (a) an alcohol component, which is a C 17 alcohol mixture having an average iso-index of 2.8 to 3.7 and (b) an acid component, which is an aliphatic C 4 -C lO , preferably C 5 -C 7 dicarboxylic acid or cyclohexanedicarboxylic acid surprisingly provides a better seal compatibility.
  • the ester component as described herein is used for improving compatibility towards nitrile-butadiene-copolymer.
  • lubricant compositions modified using said ester component show a seal compatibility with nitrile-butadiene rubber determined according to ISO 1817 at 100°C for 168 hours resulting in a mass change of 20% or lower, preferably 10% or lower.
  • the lubricant composition shows a seal compatibility with nitrile-butadiene-copolymer determined according to ISO 1817 at 100°C for 168 hours resulting in a volume change of 30% or lower, preferably 15% or lower.
  • the lubricant composition shows a seal compatibility with nitrile-butadiene-copolymer determined according to ISO 1817 at 100°C for 168 hours resulting in a hardness change of 12% or lower, preferably 8% or lower.
  • the data regarding the mass change, volume change or hardness change is obtained from a comparison of the nitrile-butadiene-copolymer based seal before being subjected to the lubricant composition and after being exposed to the lubricant composition for 168 hours at 100°C.
  • the lubricant compositions according to the present invention may be used in 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 water-based metalworking liquids, oil for neat oil metalworking fluids, oil for semi-synthetic metalworking fluids, oil for synthetic metalworking fluids, drilling detergents for the soil exploration, hydraulic oils, in
  • the iso-index is determined by derivatizing an alcohol sample with trichloroacetylisocyanate (TAI), thus transferring the alcohols into carbamine esters.
  • TAI trichloroacetylisocyanate
  • the alcohol sample is dissolved in CDCl 3 and a small amount of TMS is added as frequency standard in accordance is common practice. Then 0.2 ml TAI are added to the solution before a 1 H-NMR spectrum is recorded.
  • the total acid number is determined by titrating a sample with KOH according to DIN 51558-1.
  • the kinematic viscosity is determined in accordance with DIN 51562 (kinematic viscosity at 40°C and 100°C: DIN 51562-1, at 20°C: DIN 51562-2, at 0°C: DIN 51562-3).
  • the viscosity index is determined according to DIN ISO 2909.
  • the pour point is determined according to ASTM D97.
  • NBR nitrile-butadiene-rubber
  • An ester component typically used in conventional lubricant compositions was obtained by estrification of adipic acid with an excess of an alcohol mixture containing 2-propylheptanol and 15 wt% of trimethylol propane resulting in an ester having similar viscosity than the ester in the inventive example.
  • the ester component according to the invention exhibits a rheological profile similar to ester components currently employed in lubricant compositions.
  • the ester component has a kinematic viscosity at 40°C of about 46 mm 2 /s.
  • the ester component according to the inventive example shows significantly improved seal compatibility.
  • the ester component can advantageously be employed for replacing conventional ester components in lubricant compositions.
  • the ester component of the inventive example was tested for hydrolysis stability by determining the acid value in a reaction with water at 100°C. An acid value of 1 or lower, preferably 0.5 or lower after a 12-day reaction is considered sufficient for practical use.
  • the ester component of the inventive example shows excellent hydrolysis stability.
  • the oxidation stability of the ester component of the inventive example including 2 wt% additives was determined using the turbine oil stability test (TOST) Dry according to ASTM-D 943.
  • Table 3 Hours Ethanol Ethanol increase 0 0.44 - 168 0.43 -0.01 336 0.42 -0.02 504 0.41 -0.03 672 0.39 -0.05
  • the ester component of the inventive example shows sufficient oxidation stability for practical use.
  • Lubricant suitable is exemplified in the following: Table 4 Lubricant composition I E2 Ester component [wt%] 10 Base oil component [wt%] 50.6 Additive component Thickener 1 [wt%] 12.7 Thickener 2 [wt%] 12.7 Additive package [wt%] 14.0
  • the ester component described in inventive example 1 was used.
  • the base oil component is a polyalphaolefin 6 available from Neste Oil under the trade designation Nexbase ® 2006.
  • the additive component comprises two thickeners and an additive package.
  • Thickener 1 is Lubrizol ® 8406 available from Lubrizol.
  • Thickener 2 is Lubrizol ® 8407 from Lubrizol.
  • the additive package is Anglamol ® 6004 available from Lubrizol.

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Claims (15)

  1. Composition de lubrifiant comprenant un constituant ester dérivé de (a) un constituant alcool, qui est un mélange d'alcools en C17 ayant un indice moyen de ramification calculé comme défini dans les exemples de 2, 8 à 3, 7 et (b) un constituant acide, qui est un acide dicarboxylique aliphatique en C4-C10 ou l'acide cyclohexanedicarboxylique.
  2. Composition de lubrifiant selon la revendication 1, dans laquelle le constituant alcool comprend en outre un polyol, de préférence choisi parmi le triméthylolpropane, le néopentylglycol, le pentaérythritol ou le dipentaérythtol.
  3. Composition de lubrifiant selon la revendication 1 ou 2, dans laquelle le constituant ester a une viscosité cinématique déterminée selon la norme DIN 51562-1 à 40 °C de 20 à 70 mm2/s, de préférence de 35 à 55 mm2/s, de préférence encore de 40 à 50 mm2/s, de préférence même encore d'environ 46 mm2/s.
  4. Composition de lubrifiant selon l'une quelconque des revendications 1 à 3, dans laquelle le constituant alcool a un indice moyen de ramification de 2,9 à 3,6, de préférence de 3,01 à 3,5, de préférence encore de 3,05 à 3,4.
  5. Composition de lubrifiant selon l'une quelconque des revendications 1 ou 4, dans laquelle le constituant acide est dérivé d'acide cyclohexane-1,2-dicarboxylique, d'acide cyclohexane-1,3-dicarboxylique ou d'acide cyclohexane-1,4-dicarboxylique ou d'un acide dicarboxylique aliphatique choisi parmi l'acide glutarique, l'acide adipique, l'acide pimélique, l'acide azélaïque et l'acide sébacique, de préférence dans laquelle le constituant acide est dérivé d'un acide dicarboxylique aliphatique en C5-C7 ou d'acide cyclohexanedicarboxylique, de préférence encore d'acide cyclohexane-1,2-dicarboxylique, d'acide cyclohexane-1,3-dicarboxylique ou d'acide cyclohexane-1,4-dicarboxylique ou d'un acide dicarboxylique aliphatique choisi parmi l'acide glutarique, l'acide adipique, l'acide pimélique, de préférence par-dessus tout d'acide adipique.
  6. Composition de lubrifiant selon l'une quelconque des revendications 1 à 5, la composition de lubrifiant comprenant le constituant ester, un constituant additif et éventuellement un constituant huile de base.
  7. Composition de lubrifiant selon la revendication 6, comprenant par rapport au poids total de la composition de lubrifiant :
    (i) 5 à 99,9 % en poids du constituant ester,
    (ii) 0 à 75 % en poids d'un constituant huile de base, de préférence choisi dans le groupe constitué par une huile minérale du groupe I, une huile minérale du groupe II, une huile minérale du groupe III, une huile du groupe IV, une huile du groupe V et les mélanges de celles-ci, et
    (iii) 0,1 à 20 % en poids d'un constituant additif, de préférence choisi dans le groupe constitué par les antioxydants, les dispersants, les antimousses, les désémulsifiants, les agents gonflants de joints d'étanchéité, les agents abaissant le coefficient de frottement, les agents antiusure, les détergents, les inhibiteurs de corrosion, les agents extrême pression, les désactivateurs de métaux, les antirouilles, les agents abaissant le point d'écoulement et les mélanges de ceux-ci.
  8. Composition de lubrifiant selon l'une quelconque des revendications 1 à 7, dans laquelle ledit constituant ester est compris en une quantité de 50 à 99 % en poids, de préférence de 80 à 99 % en poids, par rapport au poids total de la composition de lubrifiant.
  9. Composition de lubrifiant selon la revendication 6 ou 7, dans laquelle le constituant huile de base comprend une poly-alpha-oléfine (huile du groupe IV), de préférence encore une poly-alpha-oléfine 4, une poly-alpha-oléfine 6 et/ou une poly-alpha-oléfine 8, de préférence une poly-alpha-oléfine 6.
  10. Composition de lubrifiant selon l'une quelconque des revendications 6 à 9, dans laquelle ledit constituant huile de base est compris en une quantité de 0 à 19 % en poids, par rapport au poids total de la composition de lubrifiant.
  11. Composition de lubrifiant selon l'une quelconque des revendications 6 à 10, dans laquelle ledit constituant additif est compris en une quantité de 1 à 20 % en poids, par rapport au poids total de la composition de lubrifiant.
  12. Utilisation du constituant ester tel que défini dans l'une quelconque des revendications 1 à 5 pour l'amélioration de la compatibilité de compositions de lubrifiant avec des joints d'étanchéité.
  13. Utilisation selon la revendication 12, dans laquelle la composition de lubrifiant présente une compatibilité avec des joints d'étanchéité en copolymère de nitrile-butadiène déterminée selon la norme ISO 1817 à 100 °C pendant 168 heures de
    (i) un changement de masse inférieur ou égal à 20 %, de préférence inférieur ou égal à 10 %, et/ou
    (ii) un changement de volume inférieur ou égal à 30 %, de préférence inférieur ou égal à 15 %, et/ou
    (iii) un changement de dureté inférieur ou égal à 12 %, de préférence inférieur ou égal à 8 %.
  14. Utilisation selon la revendication 12 ou 13, dans laquelle la composition de lubrifiant est telle que définie dans l'une quelconque des revendications 6 à 11.
  15. Utilisation selon l'une quelconque des revendications 12 à 14, dans laquelle la composition de lubrifiant est une huile pour moteurs légèrement puissants, moyennement puissants et très puissant, une huile pour moteurs industriels, une huile pour moteurs marins, une huile pour moteurs d'automobiles, une huile pour vilebrequins, une huile pour compresseurs, une huile pour machines frigorifiques, une huile pour compresseurs d'hydrocarbures, une huile de graissage et une graisse pour les très basses températures, une huile de graissage et une graisse pour les hautes températures, un lubrifiant pour câbles métalliques, une huile pour machines textiles, un lubrifiant pour l'aviation et l'aérospatial, une huile pour turbines d'aviation, une huile pour transmissions, une huile pour turbines à gaz, une huile à broche, une huile d'ensimage, un fluide de traction, une huile pour transmissions en plastique, une huile pour transmissions de voitures automobiles, une huile pour transmissions de camions, une huile pour transmissions industrielles, une huile pour engrenages industriels, une huile isolante, une huile pour instruments, un liquide de frein, un liquide de transmission, une huile pour amortisseurs, une huile caloporteuse, une huile pour transformateurs, une graisse, une huile pour chaînes, un lubrifiant en quantité minimale pour des opérations de travail des métaux, une huile pour le formage après préchauffage et à froid, une huile pour un liquide de travail des métaux à base d'eau, une huile pour un fluide de travail des métaux de type huile pure, une huile pour un fluide de travail des métaux semi-synthétique, une huile pour un fluide de travail des métaux synthétique, un détergent de forage pour l'exploration du sol, une huile hydraulique, un lubrifiant ou une graisse ou cire lubrifiante biodégradables, une huile pour tronçonneuses à chaîne, un agent de démoulage, un fluide pour le moulage, un lubrifiant pour revolvers, pistolets et fusils ou un lubrifiant de montres et un lubrifiant homologué de qualité alimentaire.
EP14165470.7A 2014-04-22 2014-04-22 Composition lubrifiante comprenant un ester de mélange d'alcools en C17 Not-in-force EP2937408B1 (fr)

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