EP3555249A1 - Ether-based lubricant compositions, methods and uses - Google Patents

Ether-based lubricant compositions, methods and uses

Info

Publication number
EP3555249A1
EP3555249A1 EP17816809.2A EP17816809A EP3555249A1 EP 3555249 A1 EP3555249 A1 EP 3555249A1 EP 17816809 A EP17816809 A EP 17816809A EP 3555249 A1 EP3555249 A1 EP 3555249A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
lubricant composition
lubricant
cycloalkyl
ether
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.)
Withdrawn
Application number
EP17816809.2A
Other languages
German (de)
English (en)
French (fr)
Inventor
Gordon David Lamb
John Michael REDSHAW
Kevin Richard West
Rebecca YATES
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Castrol Ltd
Original Assignee
Castrol Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Castrol Ltd filed Critical Castrol Ltd
Publication of EP3555249A1 publication Critical patent/EP3555249A1/en
Withdrawn legal-status Critical Current

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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
    • 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
    • C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06—Metal compounds
    • C10M2201/065—Sulfides; Selenides; Tellurides
    • C10M2201/066—Molybdenum sulfide
    • 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
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/028—Overbased salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/066—Arylene diamines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbasedsulfonic acid salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/12—Groups 6 or 16
    • 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
    • C10N2030/04—Detergent property or dispersant property
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/52—Base number [TBN]
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/54—Fuel economy
    • 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
    • C10N2030/74—Noack Volatility
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines

Definitions

  • the present invention relates to lubricant compositions containing base oils comprising certain ether base stocks which are suitable for use in a lubricant composition intended for use in an internal combustion engine. Also provided are methods and uses of the lubricant compositions and of the ether base stocks.
  • Lubricating compositions generally comprise a base oil of lubricating viscosity together with one or more additives to deliver properties including for example, reduced friction and wear, improved viscosity index, improved dispersancy, detergency, and resistance to oxidation and corrosion.
  • a lubricant base oil may comprise one or more lubricating base stocks.
  • Lubricant base stocks used in automotive engine lubricants are generally obtained from petrochemical sources, for example they may be obtained as the higher boiling fractions isolated during the refining of crude oil or as the products of chemical reactions of feedstocks from petrochemical sources. Lubricant base stocks can also be made from Fischer-Tropsch wax.
  • Lubricant base stocks may be classified as Group I, II, III, IV and V base stocks according to API standard 1509, "ENGINE OIL LICENSING AND CERTIFICATION SYSTEM", 17 th Edition, Annex E (October 2013 with Errata March 2015), as set out in Table 1.
  • Group I base stocks are typically manufactured by known processes including, for example, solvent extraction and solvent dewaxing, or solvent extraction and catalytic dewaxing.
  • Group II and Group III base stocks are typically manufactured by known processes including, for example, catalytic hydrogenation and/or catalytic hydrocracking, and catalytic hydroisomerisation.
  • Group IV base stocks include for example,
  • a combination of properties is desirable in a base stock for conferring to a lubricant composition comprising it.
  • a base stock for example in passenger car engine oils, it may be desirable for a base stock to confer a low viscosity profile on the lubricant composition, since this leads to improved fuel economy, for instance, as a result of a thinner oil film.
  • base stocks it is desirable for base stocks to have a low kinematic viscosity as well as good low-temperature viscosity characteristics, for example a low pour point or low viscosity as measured using a mini-rotary viscometer (MRV).
  • MMV mini-rotary viscometer
  • the general trend is for an improvement in the viscosity profile (i.e.
  • turbochargers which operate at high temperatures, promote coking related deposit formation which can, amongst other things, lead to scuffing related engine failure.
  • lubricant compositions it is also desirable for lubricant compositions to exhibit good high temperature stability performance so as to reduce high temperature induced deposit formation.
  • a lubricant composition having low volatility for a given viscosity profile, but which is also suitable for use in an internal combustion engine.
  • a lubricant composition which offers good fuel economy performance together with high temperature stability.
  • the present invention provides a lubricant composition for an internal combustion engine comprising a base oil of lubricating viscosity, wherein the base oil comprises an ether base stock of formula (A): (A) where: R a and R b are aliphatic hydrocarbyl groups and may be the same or different; wherein at least one of R a and R b is branched-chain alkyl, alkoxy-substituted-alkyl or cycloalkyl-substituted-alkyl;
  • the lubricant composition further comprising:
  • At least one polymethacrylate compound as a lubricant additive which is present in an amount of from 0.1 to 7.5 % by weight of the lubricant composition.
  • the ether base stock of the lubricant composition is selected from a subset of the compounds of formula (A), namely a compound of formula (1):
  • Ri and R 2 are alkyl or, together with the carbon atom to which they are
  • R 3 , R ( and R 5 are H or alk l;
  • R6 is alkyl or
  • R 7 and Rs are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
  • Rg is H or alkyl
  • X is alkylene or is absent
  • p 0, 1, 2 or 3;
  • n and n are 0, 1 , 2 or 3 provided that m is 0 when R 4 and R 5 are H. Also provided are methods of preparing lubricant compositions. Also provided is a method for lubricating a surface using a lubricant composition, as well as the use of a lubricant composition for lubricating a surface.
  • a lubricant composition for an internal combustion engine comprising a base oil of lubricating viscosity, wherein the base oil comprises an ether base stock of formula (A):
  • R a and R b are aliphatic hydrocarbyl groups and may be the same or different; wherein at least one of R a and R b is branched-chain alkyl, alkoxy-substituted-alkyl or cycloalkyl-substituted-alkyl;
  • the lubricant composition further comprising:
  • aliphatic hydrocarbyl refers to a group comprising hydrogen and carbon atoms, where one or more carbon atoms may optionally be replaced with -0-, which group may be saturated or unsaturated, preferably saturated, and contains from 1 to 40 carbon atoms.
  • hydrocarbyl groups include hydrocarbyl groups containing from 2 to 28 carbon atoms, such as from 3 to 26 carbon atoms or from 4 to 24 carbon atoms. Where one or more of the carbon atoms is replaced with -0-, from 2% to 35 % of the carbon atoms are preferably replaced with -0-, or from 5 % to 25%.
  • the aliphatic hydrocarbyl group has 1 to 3 carbon atoms replaced with -0-, for example 2 carbon atoms replaced with -0-. In other examples, none of the carbon atoms are replaced with -0-.
  • Examples of aliphatic hydrocarbyl groups include acyclic groups, non-aromatic cyclic groups and groups comprising both an acyclic portion and a non-aromatic cyclic portion.
  • the aliphatic hydrocarbyl group may be straight chain or branched chain.
  • the aliphatic hydrocarbyl group includes monovalent groups and polyvalent groups as specified. Examples of monovalent hydrocarbyl groups include alkyl, alkenyl, alkynyl and carbocyclyl (e.g. cycloalkyl or cycloalkenyl).
  • alkyl refers to a monovalent straight or branched chain alkyl moiety containing from 1 to 40 carbon atoms.
  • alkyl groups include alkyl groups containing from 1 to 30 carbon atoms, e.g. from 2, 3 or 4 carbon atoms to 24, 25, or 26 carbon atoms, e.g. from 1 to 20 carbon atoms, from 1 to 14 carbon atoms, from 2 to 26 carbon atoms and from 3 to 24 carbon atoms.
  • Particular examples include alkyl groups containing 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 and 30 carbon atoms.
  • alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert- butyl, pentyl, hexyl and the like. Unless specifically indicated otherwise, the term "alkyl" does not include optional substituents.
  • cycloalkyl refers to a monovalent saturated aliphatic hydrocarbyl moiety containing from 3 to 40 carbon atoms and containing at least one ring, wherein said ring has at least 3 ring carbon atoms.
  • the cycloalkyl groups mentioned herein may optionally have alkyl groups attached thereto.
  • Examples of cycloalkyl groups include cycloalkyl groups containing from 3 to 16 carbon atoms, e.g. from 3 to 10 carbon atoms. Particular examples include cycloalkyl groups containing 3, 4, 5 or 6 ring carbon atoms.
  • Examples of cycloalkyl groups include groups that are monocyclic, polycyclic (e.g. bicyclic) or bridged ring system.
  • Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
  • alkenyl refers to a monovalent straight or branched chain alkyl group containing from 2 to 40 carbon atoms and containing, in addition, at least one carbon-carbon double bond, of either E or Z configuration unless specified.
  • alkenyl groups include alkenyl groups containing from 2 to 28 carbon atoms, e.g. from 3 to 26 carbon atoms, e.g. from 4 to 24 carbon atoms.
  • Particular examples include alkenyl groups containing 2, 3, 4, 5 or 6 carbon atoms.
  • alkenyl groups include ethenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 1- hexenyl, 2-hexenyl, 3-hexenyl and the like.
  • alkylene refers to a divalent straight or branched chain saturated hydrocarbyl group consisting of hydrogen and carbon atoms and containing from 1 to 30 carbon atoms.
  • alkylene groups include alkylene groups that contain from 1 to 20 carbon atoms, e.g. from 1 to 12 carbon atoms, e.g. from 1 to 10 carbon atoms.
  • Particular examples include alkylene groups that contain 1, 2, 3, 4, 5 or 6 carbon atoms.
  • alkoxy refers to -O-alkyl, wherein alkyl is as defined herein.
  • an alkoxy group contains from 1 to 40 carbon atoms, e.g. from 1 to 28 carbon atoms, or from 1 to 26 carbon atoms, or from 1 to 24 carbon atoms e.g. from 1 to 10 carbon atoms.
  • Particular examples include alkoxy groups that contain 1, 2, 3, 4, 5 or 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentoxy, hexoxy and the like.
  • alkoxy-substituted-alkyl and "cycloalkyl-substituted-alkyl” refer to a straight or branched chain alkyl group in which one of the hydrogens of the alkyl chain is replaced with an alkoxy or cycloalkyl group as described herein, respectively.
  • Ra and Rb of formula (A) are independently selected from alkyl, alkoxy-substituted-alkyl and cycloalkyl-substituted-alkyl, provided that where Ra and Rb are both alkyl at least one of R a and Rb is branched-chain alkyl. In preferred embodiments, when Ra and Rb are both alkyl, both Ra and Rb are branched-chain alkyl.
  • Ra and Rb of formula (A) are independently selected from Ci_3o alkyl, such as C2-20 alkyl, C5-30 cycloalkyl-substituted-alkyl, such as C5-25 cycloalkyl- substituted-alkyl, or C2-30 alkoxy-substituted-alkyl, such as C 2 _ 2 o alkoxy-substituted-alkyl.
  • Ra of formula (A) contains more carbon atoms than Rb. In some embodiments, Ra of formula (A) contains from 12 to 30 carbon atoms, preferably from 12 to 26 carbon atoms, and/or Rb contains from 2 to 20 carbon atoms, preferably from 2 to 12 carbon atoms.
  • the ether base stock of the lubricant composition is a compound of formula (1): (1) where: Ri and R 2 are alkyl or, together with the carbon atom to which they are
  • R 5 are H or alkyl
  • Re is alkyl
  • R 7 and Rs are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
  • R9 is H or alkyl
  • X is alkylene or is absent
  • p 0, 1, 2 or 3;
  • Ri and R 2 are C 1-15 alkyl or, together with the carbon atom to which they are attached, C 5 _ 30 cycloalkyl, such as C 2-12 alkyl or, together with the carbon atom to which they are attached, Cs_ 2 5 cycloalkyl.
  • R 3 , R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
  • R 5 is H.
  • R 6 is Ci_ 2 o alkyl or , such as
  • R 7 and Rs are H, Ci_ 2 o alkyl or, together with the carbon atom to which they are attached, C5-30 cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, Cs_ 2 5 cycloalkyl.
  • R 7 and Rs are Ci_ 2 o alkyl, such as C 2-12 alkyl.
  • R9 is H or Ci_ 2 o alkyl, such as H or C 2-12 alkyl.
  • R9 is H.
  • X is Ci_ 2 o alkylene, such as C 3-15 alkylene.
  • p is 0, 1 or 2, such as 0 or 1.
  • m and n are 0, 1 or 2, such as 0 or 1.
  • Ri and R 2 are as described as alkyl or, together with the carbon atom to which they are attached, cycloalkyl. It will be understood that, where Ri and R 2 are both alkyl groups, they may be the same as or different from one another. Similar considerations apply to other substituents which are defined as part of a group of substituents. Thus, the considerations apply, for example, to R3, R 4 and R 5 ; to R 7 and Rg; and to the values taken by m and n.
  • R3, R4 and R 5 are described as being H or alkyl, it will be understood that each of R3, R4 and R 5 may be H, each of R3, R4 and R 5 may be alkyl, or a subset of R3, R 4 and R5 may be H and another subset of R3, R4 and R5 may be alkyl.
  • R3, R 4 and R 5 are alkyl
  • each of R3, R4 and R 5 may be the same alkyl group or they may be different alkyl groups.
  • Ri or any other notation
  • Ri is used at a number of locations in a formula, it is used to denote the presence of the same group at each of these locations.
  • the ether compounds of the lubricant compositions may contain a total number of carbons atoms of from about 20 to about 50.
  • the total number of carbons in the ether compounds may be from about 25 to about 45, such as from about 28 to about 40 or from about 28 to about 36.
  • alkyl and alkylene groups mentioned herein i.e. those that may be represented by Ra, Rb, Ri, R 2 , R 3 , R , R 5 , Re, R7, Rs, R and X, may be straight chain alkyl or alkylene groups, though they may also be branched.
  • each alkyl group and each alkylene group contains a single branch point or is a straight chain alkyl or alkylene group.
  • Ra and R b are both alkyl groups, at least one of these alkyl groups is branched, preferably both.
  • the alkyl and alkylene groups are straight chain alkyl or alkylene groups. It will be understood that, aside from alkyl branching (if present), the alkyl and alkylene groups are unsubstituted unless otherwise indicated and so may not contain any atoms other than carbon or hydrogen.
  • the ether compounds described herein may be used for improving the high temperature stability of a lubricant composition, for reducing or preventing scuffing in the piston system of an engine or for reducing or preventing deposits in the turbochargers or other hot surfaces, for example piston undercrowns, of an engine.
  • a molybdenum compound or polymethacrylate compound as defined herein, as well as phenate and/or neutral sulphonate detergents, in the lubricant compositions of the invention have also been found to enhance high temperature stability in the ether based lubricant compositions and/or be better tolerated in terms of high temperature stability in ether based compositions as defined herein in comparison with conventional non-ether based lubricant compositions.
  • the lubricant compositions of the invention may also be used for reducing or preventing scuffing in the pistons of an engine or for reducing or preventing deposits in the turbochargers or other hot surfaces of an engine.
  • a method of reducing or preventing i) scuffing in the pistons of an engine and/or ii) deposits in the turbochargers of an engine comprising the step of providing to the engine a lubricant composition as described herein.
  • a method of improving the fuel economy performance and/or piston cleanliness performance and/or turbocharger cleanliness performance of an engine and/or a vehicle, such as an automotive vehicle associated with an internal combustion engine comprising the step of providing the engine and/or the vehicle with a lubricant composition as described herein.
  • the compounds of formula (A) and/or formula (1) may have a kinematic viscosity at 40 °C of less than about 25 cSt, such as less than about 20 cSt, or less than about 17 cSt.
  • the compounds may have a kinematic viscosity at 100 °C of less than about 7 cSt, such as less than about 5 cSt, or less than about 4 cSt.
  • the compounds may have a viscosity index of greater than about 100, such as greater than about 110, or greater than about 120.
  • the kinematic viscosity at 40 °C and the kinematic viscosity at 100 °C may be measured according to ASTM D7279.
  • the viscosity index may be measured according to ASTM D2270.
  • the compounds may have a Noack volatility of less than about 26%, such as less than about 20%, less than about 16 %, or less than about 12 % by weight. Noack volatility may be measured according to CEC-L-40-A-93.
  • the compounds may have a viscosity at 150 °C and a shear rate of 10 6 s "1 of no greater than 1.7 cP, such as no greater than 1.5 cP.
  • This high temperature high shear viscosity may be measured according to CEC-L-36-A-90.
  • the ether compounds described herein may have a pour point of less than -10 °C, such as less than about -25 °C, or less than about -35 °C. Pour point may be measured according to ASTM D5950.
  • the ether compounds may have a cold-crankcase simulator viscosity at -35 °C of less than about 1800 cP, such as less than about 1500 cP, or less than about 1200 cP, for example as measured according to ASTM D5293.
  • the ether compounds may have a DSC oxidation onset temperature of greater than about 165 °C, such as greater than about 175 °C, or greater than about 185 °C, for example as measured according to ASTM E2009 (method B).
  • the ether compounds of formula (A) or formula (1) may have a kinematic viscosity at 100 °C of about 3 to about 4 cSt and a Noack volatility of less than about 20%>, such as less than about 16 %>, or less than about 12 %>, by weight; or a kinematic viscosity at 100 °C of about 2 to about 3 cSt, and a Noack volatility of less than about 40 %>, such as less than about 30 %>, by weight.
  • the ether compounds of formula (A) or formula (1) are particularly suited for blending into a lubricant composition.
  • the compounds are miscible with conventional base stocks, including hydrocarbon base stocks, as well as with conventional lubricant additives.
  • the compounds may be used in a lubricant composition in a relatively high amount (for example, in an amount of greater than about 10 % by weight, such as greater than about 20 %> by weight or greater than about 30 %> by weight) whilst meeting elastomer compatibility requirements for lubricant compositions.
  • the compounds of formula (A) and formula (1) may be prepared from a wide range of commercially available feedstocks.
  • the compounds are prepared from bio-derived feedstocks.
  • the compounds may contain greater than about 50 %, such as greater than about 70 %, or greater than about 80 % by weight of biobased carbon.
  • the biobased carbon content of the compounds may be measured according to ASTM D6866.
  • the compounds of formula (1) are derived from ⁇ - alkylated alcohols.
  • the compound may have the formula (2):
  • Ri and R 2 are alkyl or, together with the carbon atom to which they are
  • R 3 and R 5 are H or alkyl
  • R4 is alkyl
  • Re is alkyl or ;
  • R 7 and Rs are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
  • R9 is H or alkyl
  • X is alkylene or is absent
  • p 0, 1, 2 or 3;
  • n 0, 1, 2 or 3.
  • Ri and R 2 are C 1-15 alkyl or, together with the carbon atom to which they are attached, C 5 - 3 o cycloalkyl, such as C 2 _i 2 alkyl or, together with the carbon atom to which they are attached, C 5 _ 2 5 cycloalkyl.
  • Ri and R 2 are C 1-15 alkyl, such as C 2 _i 2 alkyl.
  • R 3 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
  • R 3 and R 5 are H.
  • R 4 is C 1-15 alkyl, such as C -12 alkyl.
  • R 6 is C 1-15 alkyl or such as
  • R 7 and Rs are H, Ci_ 2 o alkyl or, together with the carbon atom to which they are attached, C 5 - 3 o cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, Cs_ 2 5 cycloalkyl.
  • R 7 and Rs are Ci_ 2 o alkyl, such as C 2-12 alkyl.
  • Rg is H or Ci_ 2 o alkyl, such as H or C 2-12 alkyl.
  • Rg is H.
  • X is Ci_ 2 o alkylene, such as C 3 _i 5 alkylene.
  • p is 0, 1 or 2, such as 0 or 1.
  • n is 0, 1 or 2, such as 0 or 1.
  • the compound is derived from a ⁇ -alkylated alcohol, it is preferably derived, at least in part, from a Guerbet alcohol.
  • Compounds which are derived, at least in part, from Guerbet alcohols may have the formula (3):
  • Ri is alkyl
  • P 3 and P 5 are H or alkyl
  • R 4 is alkyl
  • Re is alkyl
  • R 7 and Rg are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
  • R9 is H or alkyl
  • X is alkylene or is absent
  • p 0, 1 , 2 or 3;
  • n 0, 1 , 2 or 3.
  • Ri is C 1-12 alkyl, such as C 2-10 alkyl.
  • R 3 is H or C 1-12 alkyl, such as H or C 2-10 alkyl. Preferably, R 3 is H.
  • R 4 is C 1-15 alkyl, such as C 2-12 alkyl.
  • R 5 is H or C 1-15 alkyl, such as H or C 2-12 alkyl. Preferably, R 5 is H.
  • R 6 is C 1-15 alkyl or such as
  • R 6 is C 1-15 alkyl, such as C 1-12 alkyl.
  • R 7 and Rg are H, Ci_ 2 o alkyl or, together with the carbon atom to which they are attached, C 5 _ 30 cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, Cs_ 2 5 cycloalkyl.
  • R 7 and Rg are Ci_ 2 o alkyl, such as C 2-12 alkyl.
  • R 9 is H or Ci_ 2 o alkyl, such as H or C 2 _i 2 alkyl.
  • R 9 is H.
  • X is Ci_ 2 o alkylene, such as C 3-15 alkylene.
  • p is 0, 1 or 2, such as 0 or 1.
  • n is 0, 1 or 2, such as 0 or 1.
  • One portion of the compound of formula (3) has a structure which may be derived from a Guerbet alcohol (i.e. the portion containing Ri and R 3 ), whereas the other portion need not be derived from a Guerbet alcohol (i.e. the portion containing R 4 , R 5 and R ⁇ ).
  • the compound may be derived from a combination of two Guerbet alcohols.
  • a compound prepared in this way may have the formula (4):
  • Ri and R 4 are alkyl
  • R 3 and R5 are H or alkyl.
  • Ri and R 4 are C 1-12 alkyl, such as C 2 _io alkyl.
  • R 3 and R 5 are H or C 1-12 alkyl, such as H or C 2 _io alkyl.
  • R 3 and R 5 are H.
  • Ri is C 4 _i 2 alkyl, such as C 6 _io alkyl;
  • R 3 is H
  • R 4 is Ci_io alkyl, such as C 2 _g alkyl.
  • R 5 is H.
  • Ri and R 4 may be different.
  • R 3 and R5 may be different.
  • Ri and R 4 are different and R 3 and R 5 are also different.
  • the compound may be derived from a reaction in which the same Guerbet alcohols are combined.
  • a compound prepared in this way may have the formula (5):
  • Ri is alkyl
  • R 3 is H or alkyl.
  • Ri is C 1-10 alkyl, such as C 2 -9 alkyl.
  • R 3 is H or Ci_g alkyl, such as H or C 2 _8 alkyl.
  • R 3 is
  • Ri is C 3 _io alkyl, such as C4-8 alkyl; and R 3 is H.
  • Compounds that are derived from Guerbet alcohols include compounds GE1-GE3, GE5, GE7-GE9, SE1, SE2 and TE1 as shown in Table 2.
  • Guerbet alcohols may be prepared, for example, by dimerising primary alcohols to form a ⁇ -alkylated alcohol product in a Guerbet reaction:
  • the compound may be prepared from the Guerbet alcohol, for example, according to the following reaction:
  • Y is a leaving group
  • Ri, R 3 , R4, R 5 , R6 and n are as defined previously for the compound of formula (3).
  • one of the Guerbet alcohols may first be modified so that it contains a leaving group, Y, and the compound then prepared:
  • Y is a leaving group
  • Ri, R 3 , R4 and R 5 are as defined previously for the compound of formula (4). Where the same Guerbet alcohols are combined to form a compound, they may be combined, for example, according to the following reactions:
  • Y is a leaving group
  • Ri and R 3 are as defined previously for the compound of formula (5).
  • a mesylate group may be introduced by reacting the Guerbet alcohol with mesyl chloride in the presence of triethylamine.
  • a bromide group may be introduced by reacting the Guerbet alcohol with N-bromosuccinimide and triphenyl phosphine.
  • a base for example potassium hydroxide or potassium tert- butoxide
  • a catalyst for example Starks' catalyst: N-Methyl-N,N,N-trioctyloctan-l- ammonium chloride
  • a base for example potassium hydroxide or potassium tert- butoxide
  • a catalyst for example Starks' catalyst: N-Methyl-N,N,N-trioctyloctan-l- ammonium chloride
  • Y may be any suitable leaving group, such as a halogen (for example bromine, chlorine or iodine) or a sulfonate ester (for example mesylate or tosylate).
  • a halogen for example bromine, chlorine or iodine
  • a sulfonate ester for example mesylate or tosylate
  • the compounds of formula (1) are secondary or tertiary ether compounds.
  • the compound may have the formula (6):
  • Ri and R 2 are alkyl or, together with the carbon to which they are attached, cycloalkyl
  • R 3 , R4 and R 5 are H or alkyl; Re is alkyl or
  • R 7 and Rs are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
  • R9 is H or alkyl
  • X is alkylene or is absent
  • p 0, 1, 2 or 3;
  • n 0, 1, 2 or 3.
  • Ri and R 2 are C 1-15 alkyl or, together with the carbon atom to which they are attached, C5-30 cycloalkyl, such as C 2-12 alkyl or, together with the carbon atom to which they are attached, Cs_ 2 5 cycloalkyl.
  • Ri and R 2 are C 1-15 alkyl, such as C2-12 alkyl.
  • R3, R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
  • R 5 is H.
  • R 6 is Ci_ 2 o alkyl or , such as
  • R 7 and Rg are H, Ci_ 2 o alkyl or, together with the carbon atom to which they are attached, C5-30 cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, Cs_ 2 5 cycloalkyl.
  • R 7 and Rs are Ci_ 2 o alkyl, such as C 2-12 alkyl.
  • R 9 is H or Ci_ 2 o alkyl, such as H or C 2-12 alkyl.
  • R 9 is H.
  • X is Ci_ 2 o alkylene, such as C 3-15 alkylene.
  • p is 0, 1 or 2, such as 0 or 1. In some embodiments, n is 0, 1 or 2, such as 0 or 1.
  • Secondary and tertiary ether compounds may have the formula (7):
  • Ri and R 2 are alkyl or, together with the carbon to which they are attached, cycloalkyl
  • R 3 , R4 and R 5 are H or alkyl
  • Ri and R 2 are C 1-15 alkyl or, together with the carbon to which they are attached, C 5 - 3 o cycloalkyl, such as C 2-12 alkyl or, together with the carbon to which they are attached, Cs_ 2 5 cycloalkyl.
  • R 3 , R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
  • R5 is H.
  • R 6 is Ci_ 2 o alkyl, such as C 1-16 alkyl.
  • the compounds may be secondary ether compounds of formula (8):
  • Ri and R 2 are alkyl or, together with the carbon to which they are attached, cycloalkyl
  • R 4 and R 5 are H or alkyl
  • Ri and R 2 are C 1-15 alkyl, such as C 2-12 alkyl.
  • the secondary ether may be obtained from a cyclic compound.
  • Ri and R 2 together with the carbon to which they are attached, form a cycloalkyl group, such as a C 5 -30 cycloalkyl or a C 5 -25 cycloalkyl.
  • the cycloalkyl group may contain a cyclopentyl, cyclohexyl or cycloheptyl group optionally having one or more alkyl groups, such as C 1-12 alkyl or Ci_g alkyl, attached thereto.
  • R 4 and R5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
  • R 5 is H.
  • R 6 is Ci_ 2 o alkyl, such as C 1-16 alkyl.
  • Ri and R 2 are C3_i 2 alkyl, such as C 5 _io alkyl;
  • R 4 and R5 are H;
  • R 6 is C 4 _2o alkyl, such as C 6-15 alkyl.
  • Ri and R 2 are C3_i 2 alkyl, such as C 5 _io alkyl;
  • R 4 is C3-12 alkyl, such as C 5-10 alkyl
  • R 5 is H
  • R 6 is C 3 _i2 alkyl, such as C 5 _i 0 alkyl.
  • the compounds may be tertiary ether compounds of formula (9):
  • Ri and R 2 are alkyl or, together with the carbon to which they are attached, cycloalkyl
  • R 3 is alkyl
  • R 4 and R 5 are H or alkyl
  • Ri and R 2 are C 1-15 alkyl or, together with the carbon to which they are attached, C 5 -30 cycloalkyl, such as C 2-12 alkyl or, together with the carbon to which they are attached, C 5 -25 cycloalkyl.
  • Ri and R 2 are C 1-15 alkyl, such as C 2-12 alkyl.
  • R3 is C 1-12 alkyl, such as C 1-10 alkyl.
  • R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
  • R 6 is Ci_ 2 o alkyl, such as C 1-16 alkyl.
  • Ri and R 2 are C 2 _i 2 alkyl, such as C4_io alkyl;
  • R 3 is Ci_io alkyl, such as Ci_g alkyl
  • R 4 and R 5 are H;
  • R 6 is C 4 _ 20 alkyl, such as C 6-15 alkyl.
  • Ri, R 2 and R 3 are C 2 _i 2 alkyl, such as C 4 _io alkyl;
  • R 3 is Ci_io alkyl, such as Ci_g alkyl
  • R 4 is C 3-12 alkyl, such as C 5-10 alkyl
  • R 5 is H
  • R 6 is C 3-12 alkyl, such as C 5-10 alkyl.
  • secondary and tertiary ether compounds examples include SEl , SE2 and TEl as shown in Table 2.
  • the secondary and tertiary ether compounds may be prepared according to the following reactions:
  • Y is a leaving group
  • Ri, R 2 , R 3 , R4, R5, 5 and n are as defined previously for the compound of formula (6).
  • Y is a leaving group
  • Ri, R 2 , R3, R4, R5 and Re are as defined previously for the compound of formula (7).
  • reaction may be carried out in the presence of magnesium sulfate, sulfuric acid and dichloromethane.
  • Secondary and tertiary alcohol starting materials for use in etherification reactions will generally be commercially available, or they may be obtained from commercially available ketones.
  • the groups may be prepared by introducing a leaving group, Y, into the alcohol starting materials. Methods and reaction conditions for introducing the leaving group into alcohol are known to the skilled person.
  • Y may be any suitable leaving group, such as a halogen (for example bromine, chlorine or iodine) or a sulfonate ester (for example mesylate or tosylate).
  • a halogen for example bromine, chlorine or iodine
  • a sulfonate ester for example mesylate or tosylate
  • the compound may comprise an ether which is derived on one side from a secondary or tertiary alcohol and is derived on the other side from a Guerbet alcohol.
  • the compound may have the formula (10):
  • Ri and R4 are alkyl
  • R 3 and R 5 are H or alkyl; Re is alkyl or
  • R 7 and Rs are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
  • R9 is H or alkyl
  • X is alkylene or is absent
  • Ri is C 1-12 alkyl, such as C 2-10 alkyl.
  • R 3 is H or C 1-12 alkyl, such as H or C 2-10 alkyl. Preferably, R 3 is H.
  • R 4 is C 1-15 alkyl, such as C 2-12 alkyl.
  • R 5 is H or C 1-15 alkyl, such as H or C 2-12 alkyl. Preferably, R 5 is H.
  • R 6 is C 1-15 alkyl or such as
  • R 7 and Rs are H, Ci_ 2 o alkyl or, together with the carbon atom to which they are attached, C 5 _ 30 cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, Cs_ 2 5 cycloalkyl.
  • R 7 and Rs are Ci_ 2 o alkyl, such as C 2-12 alkyl.
  • R9 is H or Ci_ 2 o alkyl, such as H or C 2-12 alkyl.
  • R9 is H.
  • X is Ci_ 2 o alkylene, such as C 3-15 alkylene.
  • p is 0, 1 or 2, such as 0 or 1.
  • Examples of secondary and tertiary ether compounds derived from a Guerbet-alcohol include compounds SE1, SE2 and TE1 as shown in Table 2.
  • the compounds of formula (1) are monoethers.
  • the compound is a diether compound.
  • Such compounds may have the formula (11):
  • Ri and R 2 are alkyl or, together with the carbon atom to which they are
  • R 3 , R4 and R 5 are H or alkyl
  • R 7 and Rg are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
  • R9 is H or alkyl
  • X is alkylene or is absent
  • p 0, 1, 2 or 3;
  • n 0, 1, 2 or 3.
  • Ri and R 2 are C 1-15 alkyl or, together with the carbon to which they are attached, C 5 - 3 o cycloalkyl, such as C 2 _i 2 alkyl or, together with the carbon to which they are attached, C 5 - 2 5 cycloalkyl.
  • Ri and R 2 are C 1-15 alkyl, such as C 2 _i 2 alkyl.
  • R 3 , R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2 _i 2 alkyl.
  • R 3 and R 5 are H.
  • R 7 and Rs are H, Ci_ 2 o alkyl or, together with the carbon atom to which they are attached, C 5 _ 30 cycloalkyl, such as H, C 2 _i 2 alkyl or, together with the carbon atom to which they are attached, C 5 _25 cycloalkyl.
  • R 7 and Rs are Ci_ 2 o alkyl, such as C 2-12 alkyl.
  • Rg is H or Ci_ 2 o alkyl, such as H or C 2-12 alkyl.
  • Rg is H.
  • X is Ci_ 2 o alkylene, such as C 3-15 alkylene.
  • p is 0, 1 or 2, such as 0 or 1.
  • m and n are 0, 1 or 2, such as 0 or 1.
  • the diether compound may contain two ether groups, at least one of which is derived from a ⁇ -alkylated alcohol.
  • the compound may have the formula (12):
  • Ri and R 2 are alkyl or, together with the carbon atom to which they are
  • R 3 , R4 and R 5 are H or alkyl
  • R 7 and Rg are H, alkyl or, together with the carbon atom to which they are attached, cycloalkyl;
  • R9 is H or alkyl
  • X is alkylene or is absent
  • p 0, 1, 2 or 3;
  • n 0, 1, 2 or 3.
  • Ri and R 2 are C 1-15 alkyl or, together with the carbon atom to which they are attached, C 5 - 3 o cycloalkyl, such as C 2-12 alkyl or, together with the carbon atom to which they are attached, Cs_ 2 5 cycloalkyl.
  • Ri and R 2 are C 1-15 alkyl, such as C2-12 alkyl.
  • R 3 , R 4 and R 5 are H or C 1-15 alkyl, such as H or C 2-12 alkyl.
  • R 3 and R 5 are H.
  • R 4 is C 1-15 alkyl, such as C 2-12 alkyl
  • R 7 and Rs are H, Ci_ 2 o alkyl or, together with the carbon atom to which they are attached, C 5 _ 30 cycloalkyl, such as H, C 2-12 alkyl or, together with the carbon atom to which they are attached, Cs_ 2 5 cycloalkyl.
  • R 7 and Rs are Ci_ 2 o alkyl, such as C 2-12 alkyl.
  • Rg is H or Ci_ 2 o alkyl, such as H or C 2-12 alkyl.
  • Rg is H.
  • X is Ci_ 2 o alkylene, such as C 3 _i 5 alkylene.
  • p is 0, 1 or 2, such as 0 or 1.
  • n is 0, 1 or 2, such as 0 or 1.
  • Guerbet-derived base stocks GEl - GE9 examples of Guerbet-derived base stocks GEl - GE9, secondary ether base stocks SEl and SE2, and tertiary ether base stock TEl of formula (1), which may preferably be used in connection with the present application, are shown in Table 2.
  • the ether compounds of formula (A), or the subset thereof of formula (1), are used as part of a base oil in accordance with the present invention.
  • the base oils may contain an amount of compound of formula (A), or a compound of the subset thereof of formula (1), which is sufficient to impart beneficial properties of the compound onto the base oil.
  • the base oil comprises greater than about 5 %, such as greater than about 25 %, greater than about 40 %, or greater than 50 % by weight of ether compound of formula (A), or the subset thereof of formula (1).
  • the base oil may comprise up to about 100 %, such as up to about 90 % of compound of formula (A), or of the subset thereof of formula (1).
  • the compound of formula (A), or of the subset thereof of formula (1), in the base oil may be composed of a single compound or a combination of compounds of formula (A), or of the subset thereof of formula (1).
  • the remainder of the base oil may be made up with base stocks which are not compounds of formula (A) and formula (1).
  • Base stocks other than those of formula (A) and formula (1) which are suitable for use in the base oil include non-aqueous base stocks, such as Group I, Group II, Group III, Group IV and Group V base stocks.
  • the remainder of the base oil may comprise a single base stock or a combination of base stocks other than those of formula (A) and formula (1).
  • the base oils are used as part of the lubricant composition in accordance with the present invention.
  • the lubricant compositions may contain an amount of base oil which is sufficient to impart beneficial properties of the compound of formula (A), or a compound of the subset thereof of formula (1), onto the lubricating composition.
  • the lubricant composition comprises greater than about 50 %, such as greater than about 65 %, or greater than about 80 % by weight of base oil.
  • the base oil may be composed of a single base oil or a combination of base oils comprising compound of formula (A), or of the subset thereof of formula (1).
  • a particular advantage of the present invention relates to the high temperature stability conferred to the lubricant composition by the presence of ether compounds of formula (A), or of the subset thereof of formula (1).
  • the presence of at least one molybdenum compound or at least one polymethacrylate compound is better tolerated in the ether based compositions of the invention compared to conventional non-ether compositions from a high temperature stability perspective.
  • the at least one molybdenum compound or at least one polymethacrylate compound may be used to enhance high temperature stability in the lubricant compositions defined herein, or provide desirable properties to the composition without impacting the high temperature stability of the lubricant composition.
  • molybdenum compounds are well known to those skilled in the art of oil formulation to function as friction modifiers to lower engine friction and promote fuel economy.
  • too high a level of molybdenum in conventional non-ether compositions can contribute to deposits which can lead to excess wear and shorten engine life.
  • polymethacrylates are known for use as viscosity index improvers as well as pour point depressants, but their use beyond a certain amount can lead to unwanted deposit formation on hot surfaces of the engine, for example turbochargers.
  • the present invention allows the benefits of molybdenum or polymethacrylate compounds to be taken advantage of without lessening high temperature stability of the lubricant composition to the same extent as in conventional non-ether based compositions and the presence of molybdenum or polymethacrylate compounds has been found to enhance high temperature stability in some cases.
  • engine scuffing in particular, piston scuffing and deposits in high temperature regions of the engine, particularly in the turbochargers.
  • ASTM Terminology standard G40 defines scuffing as a form of wear occurring in inadequately-lubricated tribosystems that is characterized by macroscopically observable changes in texture, with features related to the direction of motion.
  • Engine scuffing is intrinsically linked with the presence of deposits in high temperature regions of the engine and therefore scuffing can be impacted by the choice of lubricant oil that is used for lubricating the engine.
  • piston scuffing or piston system scuffing it will be appreciated that this refers to scuffing on the piston ring, skirt or cylinder liner.
  • KHT Komatsu hot-tube test
  • JPI-5S-55-99 The KHT test evaluates the high temperature stability of a lubricant and is described in detail in: Ohkawa, S., Seto, K., Nakashima, T., and Takase, K., ""Hot Tube Test”- Analysis of Lubricant Effect on Diesel Engine Scuffing," SAE Technical Paper 840262, 1984, doi: 10.4271/840262.
  • the results of the KHT test correspond to deposit merit ratings which can be related to engine scuffing as described in the above paper.
  • a deposit merit rating of 0 refers to heavy deposit formation whilst a deposit merit rating of 10 means a clean glass tube at the end of the test.
  • the level of lacquer formation in the tube reflects the high temperature stability of the oil and its tendency during service to form deposits in high temperature regions of the engine, thereby causing scuffing.
  • Engine oils which pass the KHT test will have lower propensity to cause scuffing engine failure in Heavy Duty applications from scuffing as a result of deposits.
  • the KHT test also evaluates the 'hot surface deposit control', which includes surfaces associated with turbochargers, for JASO engine oil specifications (DH-1-05, DH- 2-08, DH-1-08, available in document JASO M 355:2008).
  • 'Engine Failure Analysis Internal Combustion Engine Failures and Their Causes' by Ernst Greuter and Stefan Zima, published by SAE International, 2012, page 493, ISBN 978-0-7860-0885-2, also describes carbon deposit formation on turbochargers as a result of hot surface deposit formation and supports the connection between hot surface deposits and engine scuffing which underlies the KHT test.
  • Thermo-oxidation Engine oil Simulation Test (TEOST) 33C which corresponds to standard method ASTM D6335, is a bench test which simulates the oxidation and carbonaceous deposit-forming characteristics of engine oils in the turbochargers of modern high-performance engines.
  • the TEOST 33C test generates physical measurements of deposits and represents another test through which to determine an oil's susceptibility to deposit formation in the turbochargers specifically.
  • Hot Liquid Process Simulator (HLPS)_testing may also be used as a means for characterising the propensity of an oil to create deposits in an engine by running oil over a hot surface.
  • Lubricant compositions according to the present invention have been found to outperform corresponding conventional non-ether based compositions in KHT and HLPS testing without adversely affecting the TEOST 33C, indicating that the ether compositions of the invention have greater high temperature stability than conventional lubricant compositions differing only in the absence of ether base stock. Moreover, the presence of at least one molybdenum compound or at least one polymethacrylate compound in accordance with the present invention is better tolerated in the ether compositions of the present invention than in corresponding conventional non-ether based compositions.
  • the lubricant composition according to the invention comprises the at least one molybdenum compound, on a molybdenum element basis, in an amount of at least 0.06 % by weight of the lubricant composition, when present.
  • the lubricant composition according to the invention comprises the at least one polymethacrylate compound in an amount of from 0.1 to 7.5 % by weight of the lubricant composition, when present.
  • the at least one molybdenum compound when the lubricant composition comprises at least one molybdenum compound as a lubricant additive, is present, on a molybdenum element basis, in an amount from 0.06 % to 0.25 %, from 0.075 % to 0.175 %, or from 0.075 % to 0.125 %, by weight of the lubricant composition.
  • the amount of molybdenum element present in the lubricant compositions of the invention may, for example, be determined according to method ASTM D5185.
  • the at least one polymethacrylate compound is present in an amount of from 0.25 to 7 %, from 1 to 6 %, from 2 to 4 % by weight of the lubricant composition.
  • the lubricant composition comprises at least one molybdenum compound. Any molybdenum compound may be used which is suitable for use as an additive for a lubricant composition intended for use in an internal combustion engine.
  • molybdenum compound used herein refers to a
  • molybdenum-containing compound or complex which has oil-solubility or oil- dispersibility properties.
  • Molybdenum compounds for use in the lubricant compositions of the present invention include organo molybdenum compounds, molybdenum
  • molybdenum-sulfur compounds particularly tri-nuclear molybdenum-sulfur cluster compounds as, for instance, described in EP 1 040 115 and WO 99/31113.
  • trinuclear molybdenum-sulfur compounds are also disclosed in WO98/26030, W099/31113, WO99/66013, EP 1 138 752 and EP 1 138 686.
  • such compounds may be added to a base oil fully formed or such compounds may be formed in situ as a result of the presence of sulfur-containing compounds or complexes (e.g. ZDDP), for example by means of ligand exchange.
  • the lubricant composition comprises a polymethacrylate compound.
  • polymethacrylate compound used herein refers to
  • the at least one polymethacrlyate compound may be a comb-type polymer.
  • a comb-type polymer refers to a polymer having a linear main chain (back bone) with a number of branches along the chain.
  • the at least one polymethacrylate compound may be functionalized.
  • “functionalized” in this context refers to a polymethacrylate compound with modified side chains for the purpose of imparting dispersancy to the polymer or for conferring properties of a pour point depressant.
  • preferred functionalized polymethacrylate compounds contain amine
  • the present invention also provides a lubricant composition for an internal combustion engine comprising a base oil of lubricating viscosity, wherein the base oil comprises an ether base stock of formula (A):
  • R a and R b are aliphatic hydrocarbyl groups and may be the same or different; wherein at least one of R a and R b is branched-chain alkyl, alkoxy-substituted- alkyl or cycloalkyl-substituted-alkyl;
  • the lubricant composition further comprising:
  • Metallic and non-metallic phenate and neutral sulphonate detergents may be used in accordance with this aspect of the invention.
  • Metal phenates include alkali or alkaline earth metal phenates, preferably wherein the metal is selected from barium, sodium, potassium, lithium, calcium, and magnesium, most preferably calcium and magnesium.
  • Phenols employed in the preparation of phenate detergents include hydrocarbyl substituted phenols, such as para-substituted phenols, phenols with more than one hydroxyl group, phenols with fused aromatic rings and/or alkylene bridged biphenols, any of which may be sulphurised (for example, mono- and di- sulphide bridged biphenols).
  • Suitable phenate detergents for use in the present invention include those described, for example, in US 4,221,673, US 4,104,180 and US 4,973,411.
  • the phenate detergent may have a base number (BN) of from 0.1 to 400 mg KOH/g, or from 50 to 200 mg KOH/g, for example 150 mg KOH/g, as measured in accordance with ASTM D2896.
  • BN base number
  • an overbased phenate detergent is employed having a base number (BN) of from 150 to 400 mg KOH/g, preferably 200 to 300 mg KOH/g, for example from 240 to 260 mg KOH/g, as measured in accordance with ASTM D2896.
  • Neutral metal sulphonate detergents are well-known for their use as lubricant additives and include alkali or alkaline earth metal sulphonates, preferably wherein the metal is selected from barium, sodium, potassium, lithium, calcium, and magnesium, most preferably calcium and magnesium.
  • Neutral sulphonates for use in the present invention may have a TBN of less than 60 mg KOH/g, preferably less than 40 mg KOH/g, as measured in accordance with ASTM D2896.
  • sulphonates may be prepared from sulfonic acids which are typically obtained by the sulphonation of alkyl substituted aromatic hydrocarbons, such as those obtained by alkylating benzene, toluene, xylene, naphthalene, diphenyl or their halogen derivatives such as chlorobenzene, chlorotoluene and chloronaphthalene.
  • alkyl substituted aryl sulphonates typically contain from about 9 to about 80 or more carbon atoms, preferably from about 16 to about 60 carbon atoms.
  • the lubricant composition according to the different aspects of the invention comprises a phenate detergent, preferably the phenate detergent is present in an amount of from 0.1 to 5 %, more preferably in an amount of from 0.25 to 2.5 %, most preferably in an amount of from 0.5 to 1.5 %, by weight of the lubricant composition.
  • the lubricant composition according to the different aspects of the invention comprises a neutral sulphonate detergent, preferably the neutral sulphonate detergent is present in an amount of from 0.01 to 5 %, more preferably in an amount of from 0.1 to 2.5 %, most preferably in an amount of from 0.25 to 1.5 %, by weight of the lubricant composition.
  • the lubricant compositions according to the present invention may also comprise additional lubricant additives, in addition to those referred to herein (i.e. the at least one molybdenum compound/polymethacrylate compound or neutral sulphonate/phenate detergent).
  • additional lubricant additives will typically be present in the lubricant composition in an amount of from about 2 % to about 40 % by weight, such as about 5 % to about 30 % by weight.
  • Suitable additional lubricant additives include detergents (including metallic and non-metallic detergents), friction modifiers, viscosity modifiers, dispersants (including metallic and non-metallic dispersants), dispersant viscosity modifiers, viscosity index improvers, pour point depressants, anti-wear additives, rust inhibitors, corrosion inhibitors, antioxidants (sometimes also called oxidation inhibitors), anti-foams (sometimes also called anti-foaming agents), seal swell agents (sometimes also called seal compatibility agents), extreme pressure additives (including metallic, non-metallic, phosphorus containing, non-phosphorus containing, sulphur containing and non-sulphur containing extreme pressure additives), surfactants, demulsifiers, anti-seizure agents, wax modifiers, lubricity agents, anti-staining agents, chromophoric agents, metal deactivators, and mixtures of two or more thereof.
  • detergents including metallic and non-metallic detergents
  • friction modifiers
  • the lubricant composition comprises a detergent.
  • detergents include ashless detergents (that is, non-metal containing detergents) and metal-containing detergents. Suitable non-metallic detergents are described for example in US 7,622,431.
  • Metal-containing detergents comprise at least one metal salt of at least one organic acid, which is called soap or surfactant.
  • Suitable organic acids include for example, sulphonic acids, phenols (suitably sulphurised and including for example, phenols with more than one hydroxyl group, phenols with fused aromatic rings, phenols which have been modified for example, alkylene bridged phenols, and Mannich base- condensed phenols and saligenin-type phenols, produced for example by reaction of phenol and an aldehyde under basic conditions) and sulphurised derivatives thereof, and carboxylic acids including for example, aromatic carboxylic acids (for example
  • hydrocarbyl-substituted salicylic acids and derivatives thereof for example hydrocarbyl substituted salicylic acids and sulphurised derivatives thereof).
  • the lubricant composition comprises a friction modifier.
  • Suitable friction modifiers include for example, ash-producing additives and ashless additives.
  • suitable friction modifiers include fatty acid derivatives including for example, fatty acid esters, amides, amines, and ethoxylated amines.
  • suitable ester friction modifiers include esters of glycerol for example, mono-, di-, and trioleates, mono-palmitates and mono-myristates.
  • a particularly suitable fatty acid ester friction modifier is glycerol monooleate.
  • Suitable friction modifiers also include molybdenum compounds for example, organo molybdenum compounds, molybdenum dialkyldithiocarbamates, molybdenum dialkylthiophosphates, molybdenum disulphide, tri-molybdenum cluster dialkyldithiocarbamates, non-sulphur molybdenum compounds and the like.
  • molybdenum-containing compounds are described for example, in EP 1533362 Al for example in paragraphs [0101] to [0117].
  • additional molybdenum-containing compounds may be present which are added, in particular, for their friction modifier properties. Alternatively, the presence of additional molybdenum compounds may be unnecessary.
  • the lubricant composition comprises a dispersant.
  • suitable ashless dispersants include oil soluble salts, esters, amino-esters, amides, imides and oxazolines of long chain hydrocarbon-substituted mono- and polycarboxylic acids or anhydrides thereof; thiocarboxylate derivatives of long chain hydrocarbons; long chain aliphatic hydrocarbons containing polyamine moieties attached directly thereto; Mannich condensation products formed by condensing a long chain substituted phenol with formaldehyde and polyalkylene polyamine; Koch reaction products and the like.
  • Particularly preferred dispersants for use in the present invention are long chain aliphatic hydrocarbons containing polyamine moieties attached directly thereto such as polyisobutylene succinyl anhydride-polyamines (PIBSA-PAM).
  • PIBSA-PAM polyisobutylene succinyl anhydride-polyamines
  • borated dispersants may also be used in the lubricant
  • the lubricant composition may contain boron in an amount from 0.005 wt.% to 0.05 wt.%, preferably from 0.015 wt.% to 0.035 wt.%.
  • This level of elemental boron may be derived from the use of a borated dispersants and/or boron-containing anti- wear additives or otherwise.
  • the lubricant composition comprises a dispersant viscosity modifier.
  • a dispersant viscosity modifier examples include WO 99/21902, WO 2003/099890 and WO 2006/099250.
  • the lubricant composition comprises a viscosity index improver.
  • suitable viscosity modifiers include high molecular weight hydrocarbon polymers (for example polyisobutylene, copolymers of ethylene and propylene and higher alpha-olefms); polyesters (for example polymethacrylates);
  • Oil- soluble viscosity modifying polymers generally exhibit number average molecular weights of at least about 15,000 to about 1,000,000, such as about 20,000 to about 600,000 as determined by gel permeation chromatography or light scattering methods.
  • additional methacrylate polymers may be present which are added, in particular, for their viscosity index improver properties. Alternatively, the presence of additional methacrylate polymers may be unnecessary.
  • the lubricant composition comprises a pour point depressant.
  • suitable pour point depressants include C 8 to C 18 dialkyl fumarate/vinyl acetate copolymers, methacrylates, polyacrylates, polyarylamides, polymethacrylates, polyalkyl methacrylates, vinyl fumarates, styrene esters, condensation products of haloparaffin waxes and aromatic compounds, vinyl carboxylate polymers, terpolymers of dialkyfumarates, vinyl esters of fatty acids and allyl vinyl ethers, wax naphthalene and the like.
  • the lubricant composition comprises the at least one polymethacrylate compound
  • additional methacrylate polymers may be present which are added, in particular, for their pour point depressant properties. Alternatively, the presence of additional methacrylate polymers may be unnecessary.
  • the lubricant composition comprises at least one anti-wear additive.
  • suitable anti-wear additives include non-phosphorus containing additives for example, sulphurised olefins.
  • suitable anti-wear additives also include phosphorus-containing anti-wear additives.
  • suitable ashless phosphorus-containing anti-wear additives include trilauryl phosphite and
  • triphenylphosphorothionate and those disclosed in paragraph [0036] of US 2005/0198894.
  • suitable ash-forming, phosphorus-containing anti-wear additives include dihydrocarbyl dithiophosphate metal salts.
  • dihydrocarbyl dithiophosphate metal salts include alkali and alkaline earth metals, aluminium, lead, tin, molybdenum, manganese, nickel, copper and zinc.
  • Particularly suitable dihydrocarbyl dithiophosphate metal salts are zinc dihydrocarbyl dithiophosphates (ZDDP).
  • ZDDP zinc dihydrocarbyl dithiophosphates
  • additional molybdenum-containing compounds may be present which are added, in particular, for their anti-wear properties. Alternatively, the presence of additional molybdenum compounds may be unnecessary.
  • the amount of phosphorus contained in the lubricant composition is less than 0.5 wt.%, preferably from 0.001 to 0.3 wt.%, more preferably from 0.025 to 0.2 wt.%, based on the total weight of the lubricant composition.
  • the lubricant composition comprises a rust inhibitor.
  • Suitable rust inhibitors include non-ionic polyoxyalkylene polyols and esters thereof, polyoxyalkylene phenols, polyoxyalkylene polyols, anionic alky sulphonic acids, zinc dithiophosphates, metal phenolates, basic metal sulphonates, fatty acids and amines.
  • the lubricant composition comprises a corrosion inhibitor.
  • suitable corrosion inhibitors include phosphosulphurised hydrocarbons and the products obtained by the reaction of phosphosulphurised hydrocarbon with an alkaline earth metal oxide or hydroxide, non-ionic polyoxyalkylene polyols and esters thereof, polyoxyalkylene phenols, thiadiazoles, triazoles and anionic alkyl sulphonic acids.
  • the lubricant composition comprises an antioxidant.
  • antioxidants examples include alkylated diphenylamines, N- alkylated phenylenediamines, phenyl-a-naphthylamine, alkylated phenyl-a- naphthylamines, dimethylquinolines, trimethyldihydroquinolines and oligomeric compositions derived therefrom, hindered phenolics (including ashless (metal-free) phenolic compounds and neutral and basic metal salts of certain phenolic compounds), aromatic amines (including alkylated and non-alkylated aromatic amines), sulphurised alkyl phenols and alkali and alkaline earth metal salts thereof, alkylated hydroquinones, hydroxylated thiodiphenyl ethers, alkylidenebisphenols, thiopropionates, metallic dithiocarbamates, 1 ,3,4- dimercaptothiadiazole and derivatives, oil soluble copper compounds (for example, copper dihydrocar
  • the lubricant composition comprises an antifoam agent.
  • suitable anti-foam agents include silicones, organic polymers, siloxanes (including poly siloxanes and (poly) dimethyl siloxanes, phenyl methyl siloxanes), acrylates and the like.
  • the lubricant composition comprises a seal swell agent.
  • seal swell agents examples include long chain organic acids, organic phosphates, aromatic esters, aromatic hydrocarbons, esters (for example butylbenzyl phthalate) and polybutenyl succinic anhydride.
  • the lubricant composition may comprise lubricant additives in the amounts shown in Table 3. Table 3
  • the lubricant compositions may have a kinematic viscosity at 40 °C of less than about 60 cSt, such as less than about 55 cSt, or less than about 50 cSt.
  • the lubricant compositions may have a kinematic viscosity at 100 °C of less than about 12 cSt, such as less than about 10 cSt, or less than about 9.5 cSt.
  • the lubricant compositions may have a viscosity index of greater than about 100, such as greater than about 110, or greater than about 120.
  • the kinematic viscosity at 40 °C and the kinematic viscosity at 100 °C may be measured according to ASTM D445.
  • the viscosity index may be calculated according to ASTM D2270.
  • the lubricant compositions may have a Noack volatility of less than about 25 %, such as less than about 15 %, or less than about 10 % by weight. Noack volatility may be measured according to CEC-L-40-A-93.
  • the lubricant compositions may have a viscosity at 150 °C and a shear rate of 10 6 s "1 of no greater than 3 cP, such as no greater than 2.8 cP.
  • This high temperature high shear viscosity may be measured according to CEC-L-36-A-90.
  • the lubricant composition may have at least one of:
  • the lubricant compositions may have a cold-crankcase simulator performance at -30 °C of less than about 3000, such as less than about 2800, or less than about 2750, for example as measured according to ASTM D5293.
  • Preferred lubricant compositions meet the requirements set out in SAE J300.
  • the lubricant compositions may be used in a method of lubricating a surface.
  • Suitable surfaces include those in power transmission systems for example drive lines and gear boxes for example for vehicles including for example passenger vehicles and heavy duty vehicles; and those in internal combustion engines, for example the crankcases of internal combustion engines. Suitable surfaces also include those in turbine bearings for example in water turbine bearings.
  • Suitable internal combustion engines include, for example, engines used in automotive applications, engines used in marine applications and engines used in land- based power generation plants.
  • the lubricant compositions are particularly suited to use in an automotive internal combustion engine.
  • the lubricant compositions may be used to improve the fuel economy and/or piston cleanliness performance and/or turbocharger cleanliness performance of an internal combustion engine and/or a vehicle, such as an automotive vehicle associated with an internal combustion engine. Accordingly, there are provided methods of improving the fuel economy and/or piston cleanliness performance and/or turbocharger cleanliness performance of an internal combustion engine and/or a vehicle, such as an automotive vehicle associated with an internal combustion engine, comprising the step of providing or supplying to the engine and/or vehicle at least one of the lubricant compositions.
  • Fig. 1 is a graph of Maximum Deposit Thickness (MDT) observed in HLPS analysis of blended compositions containing Guerbet-derived base stock (GE3) and/or a Group III base stock (Yubase 4) together with different detergents; and
  • Fig. 2 is a graph of deposit volume (cm 3 x 10 ⁇ 17 ) observed in HLPS analysis of blended compositions containing Guerbet-derived base stock (GE3) and/or a Group III base stock (Yubase 4) together with different detergents.
  • GE3 Guerbet-derived base stock
  • Yubase 4 a Group III base stock
  • Guerbet-derived base stock GE3 of formula (1) was prepared, the structure of which is shown in Table 4.
  • Viscosity index (VI) was calculated according to ASTM D2270. Pour point was determined according to ASTM D7346.
  • DSC Differential scanning calorimetry
  • Noack volatility was measured using a method which was based on IP 393 and was considered similar to CEC-L-40-A-93. According to the method, reference oils of known Noack volatility were heated from 40 °C to 550 °C to determine the temperature at which the Noack volatility weight loss of each of the reference oils was reached. The base stocks were subjected to the same process as the reference oils. The Noack weight of the base stocks could be determined based on the results obtained from the reference oils.
  • the Guerbet-derived base stock ether has a lower volatility, lower pour point and lower kinematic viscosity as compared to the conventional base oil, although the DSC oxidation onset temperature is lower in Guerbet-derived base stock than the conventional based oil.
  • Example 2 Properties of lubricant compositions containing ether base stocks
  • Guerbet-derived ether base stock GE3 was blended with conventional base oil additives (additive A, a commercially available additive package providing a dispersant level representative of high performance engine oil between 7 and 10 wt% based on the total weight of the lubricant composition; additive B, a cold-flow improver; additive C, an oxidation inhibitor; and additive D, a viscosity index improver) and conventional base oils (Yubase 4, a Group III base oil; and Yubase 6, a Group III base oil) to form a lubricant blend.
  • a Baseline blend was also prepared. Yubase 4 was chosen as the main component of the Baseline blend, since it exhibits a similar KV100 to Guerbet-derived ether base stock, GE3.
  • the Baseline blend was believed to be a stringent baseline for comparison, since it is a 5W-30 formulation which meets certain specifications (ACEA A5/B5, API- SN/GF-4). The details of the blended compositions are shown in Table 6 in % by weight
  • Viscosity index (VI) was calculated according to ASTM D2270.
  • CCS Cold-cranking simulator
  • High temperature high shear (HTHS) analysis was carried out according to CEC-L- 36-A-90.
  • Total base number was determined according to ASTM D2896.
  • the properties of the Guerbet-derived base stock are also exhibited in the blended composition. In particular, beneficial viscosity, volatility and cold-flow properties are observed.
  • the Guerbet-derived base stock also exhibited similar HTHS measurements, TBNs and sulphated ash contents to the Baseline blend.
  • compositions comprising Guerbet-derived base stock (GE3) and/or a Group III base stock (Yubase 4) together with varying amounts of a molybdenum- sulfur compound and/or a polymethacrylate compound (a comb-type copolymer of alkyl methacrylates in solution - approximately 1 : 1 dilution ratio) as well as additional lubricant additives including (non-borated) dispersant, ZDDP, detergents, antioxidants and viscosity modifier (VM) were subjected to the KHT test in accordance with JPI-5S-55-99 and SAE Technical Paper 840262. Results obtained from the KHT testing in the form of deposit merits are shown in Table 8 (compositional data shown in % by weight). Table 8
  • the ether containing lubricant composition 2 exhibits a significantly higher KHT merit rating (7.5) compared to that of the non-ether containing lubricant composition 1.
  • KHT merit rating 7.5
  • the ether-containing lubricant composition 4 containing an amount of 0.08 wt.% of molybdenum, exhibits the same KHT deposit merit rating (6.5) as the corresponding non-ether containing composition 3. This is particularly advantageous since the ether composition exhibits a lower viscosity profile than the non-ether composition and yet exhibits equivalent high temperature stability.
  • the results of the KHT testing demonstrate a significant advantage in the presence of the at least one polymethacrylate compound, particular in the case of the ether- containing compositions.
  • the ether-containing lubricant composition 6 also containing a polymethacrylate compound exhibits a substantially higher deposit merit rating (7.5) in the KHT test compared to the non-ether containing composition 5.
  • the ether composition is able to out-perform the corresponding non-ether composition in terms of high temperature stability.
  • ether composition exhibits a lower viscosity profile than the non-ether composition and so the present invention is able to benefit from increased fuel economy without increasing deposits in hot regions of the engine, such as in turbochargers, or causing piston scuffing which would otherwise shorten engine lifetime.
  • Example 4 TEOST 33C test
  • compositions comprising Guerbet-derived base stock (GE3) and/or a Group III base stock (Yubase 4) together with varying amounts of a molybdenum- sulfur compound and/or a polymethacrylate (a comb-type copolymer of alkyl
  • the results of the TEOST 33C generally demonstrate the benefit of increasing dispersant and detergent levels while decreasing antioxidant levels, particularly aminic antioxidant, for reducing deposit formation in turbochargers in non-ether containing compositions, in line with expectations (for instance, compare results for compositions F and G or compare composition D with A-C and E to G).
  • the results demonstrate that the presence of the at least one polymethacrylate compound, alone or also in combination with the at least one molybdenum compound, is tolerated better by the ether composition than the corresponding non-ether composition (compare results of compositions H and J as well as I and K) in the TEOST 33C test.
  • Blended compositions comprising Guerbet-derived base stock (GE3) and/or a
  • HLPS testing corresponds to a hot-tube test in which all oil compositions were subjected to the same heating stress, for the same period of time. HLPS testing is used as a means for characterising the propensity of an oil to create deposits in a hotregion of the engine by simulating pressurized oil lines.
  • the results of the HLPS tests demonstrate that, for a given TBN value, the ether based compositions comprising a phenate detergent exhibit significantly lower deposit levels than the corresponding non-ether based compositions.
  • the ether compositions comprising a typical level of neutral sulphonate also perform markedly better than the corresponding non-ether based compositions.
  • the results shown in Table 10 are also shown in the graphs of Figures 1 and 2 which show Maximum Deposit Thickness and deposit volume for each of the compositions tested respectively.

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Organic Chemistry (AREA)
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EP17816809.2A 2016-12-16 2017-12-14 Ether-based lubricant compositions, methods and uses Withdrawn EP3555249A1 (en)

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