WO2011071756A1 - Procédé de lubrification d'une boîte de vitesses à commande manuelle - Google Patents

Procédé de lubrification d'une boîte de vitesses à commande manuelle Download PDF

Info

Publication number
WO2011071756A1
WO2011071756A1 PCT/US2010/058820 US2010058820W WO2011071756A1 WO 2011071756 A1 WO2011071756 A1 WO 2011071756A1 US 2010058820 W US2010058820 W US 2010058820W WO 2011071756 A1 WO2011071756 A1 WO 2011071756A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
hydrocarbyl group
hydrogen
lubricating
oil
Prior art date
Application number
PCT/US2010/058820
Other languages
English (en)
Inventor
Paul A. Robinson
Robert W. Alger
Simon D. Evans
Malcolm G.J. Macduff
Original Assignee
The Lubrizol Corporation
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 The Lubrizol Corporation filed Critical The Lubrizol Corporation
Priority to EP10788468.6A priority Critical patent/EP2510078B1/fr
Priority to US13/513,661 priority patent/US20120302479A1/en
Publication of WO2011071756A1 publication Critical patent/WO2011071756A1/fr

Links

Classifications

    • 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
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
    • C10M129/14—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring containing at least 2 hydroxy 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
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/18—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/20—Condensation polymers of aldehydes or ketones
    • 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
    • C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
    • 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
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
    • 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
    • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
    • C10M2209/062—Vinyl esters of saturated carboxylic or carbonic acids, e.g. vinyl acetate
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
    • 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
    • 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
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • the present invention relates to a method of lubricating a driveline device comprising supplying to the driveline device a lubricating composition comprising an oil of lubricating viscosity and an aromatic hydroxy-substituted compound.
  • the invention further provides for the use of the lubricating composition comprising the aromatic hydroxy-substituted compound as at least one of a filterability aid and a wax crystal growth modifier/gelation inhibitor in the driveline device.
  • U.S. 6,495,495 discloses a filterability improver for mineral oil distillates and heavy base oils containing wax material consisting essentially of a blend containing from about 30% to about 70% of an alkyl ester polymer and from about 70% to about 30% naphthenic oil, based upon the total weight of said blend, wherein such filterability improver prevents filter blockage due to wax formation at ambient temperatures.
  • the filterability improver may be used in manual transmission oils, axle factory fill oils, and extended drain oils.
  • German Patent No. DE 1 1 47 799 Bl discloses oil-soluble copolymers of ethylene and vinyl acetate, having molecular masses between 1 ,000 and 3,000 g/mol, that are added to petroleum distillate propellants or fuels.
  • the copoly- mers that contain 60% to 99% by weight of ethylene and 1% to 40% by weight of vinyl acetate.
  • polymers employed as agents which improve flow contain, for example, 1 -hexene, as described in EP 184,083, or diisobutylene, as set forth in EP 203,554, in addition to ethylene and vinyl acetate.
  • Copolymers of ethylene, alkenecarboxylic acid esters, vinyl esters and/or vinyl ketones are also used as pour-point depressants and for improving the flow properties of crude oils and middle distillates.
  • EP 1 1 1 ,883 discloses that ethylene and vinyl acetate, copolymers of ethylene, alkenecarboxylic acid esters, vinyl esters and/or vinyl ketones are also used as pour -point depressants and for improving the flow properties of crude oils and middle distillates.
  • U.S. Patents 5,039,437 and 5,082,470 disclose alkyl phenol- formaldehyde condensates additives for improving the low temperature flow properties of hydrocarbon oils.
  • the polymer composition has a number average molecular weight of at least about 3,000 and a molecular weight distribution of at least about 1.5; in the alkylated phenol reactant the alkyl groups are essentially linear, have between 6 and 50 carbon atoms, and have an average number of carbon atoms between about 12 and 26; and not more than about 10 mole % of the alkyl groups on the alkylated phenol have less than 12 carbon atoms and not more than about 10 mole % of the alkyl groups on the alkylated phenol have more than 26 carbon atoms.
  • U.S. Patents 4,565,460; 4,559, 155; 4,575,526 and 4,613,342 all disclose additive combinations for improving the cold flow properties of hydrocarbon fuel compositions.
  • the composition includes a pour point depressant which can be a hydrocarbyl-substituted phenol of the formula (R*)a— Ar— (OH)b wherein R* is a hydrocarbyl group selected from the group consisting of hydrocarbyl groups of from about 8 to about 39 carbon atoms and polymers of at least 30 carbon atoms.
  • Ar is an aromatic moiety which can include linked polynuclear aromatic moieties represented by the general formula ar— (— Lng— ar— )— w (Q)mw wherein w is an integer of 1 to about 20.
  • Each Lng is a bridging linkage of the type including alkylene linkages (e.g.,— CH 2 — among others).
  • U.S. Patent 5,171 ,330 discloses methacyclophanes with substituents, obtained from the condensation reaction of a resorcin with a product containing an aldehyde group, followed by a reaction with halides of organic acids or alkyl halides.
  • U.S. Patent 5,707,946 discloses a pour point depressant which is the reaction product of a hydrocarbyl-substituted phenol having a number average of greater than 30 carbon atoms in the hydrocarbyl-substituent, and an aldehyde of 1 to about 12 carbon atoms, or a source therefore.
  • the lubricating composition disclosed herein may be capable of at least one of increased filterability, wax crystal growth reduction or modification, and reduced or minimised gelation in a driveline device.
  • linear hydrocarbyl means that the hydrocar- byl group has a carbon chain that is substantially free of branching, apart from the carbon atom that is the point of attachment to the phenol ring shown in formula (1) below.
  • the invention provides a method of lubricating a driveline device comprising supplying to the driveline device a lubricating composition comprising an oil of lubricating viscosity and a compound represented by formula (1):
  • each R 1 is independently hydrogen or a linear hydrocarbyl group containing at least 1 , or at least 3 , or at least 4, or at least 6, or at least 8, or at least 10 carbon atoms (typically R 1 is a linear hydrocarbyl group containing at least 1 carbon atom);
  • each R is independently a linear hydrocarbyl group containing at least 10, or at least 12, or at least 14, or at least 16 carbon atoms (R may contain carbon atoms in the range of 10 to 60, or 16 to 50, or 16 to 40, or 16 to 30, or 18 to 24, or 20 to 28, or 22 to 26);
  • each R 3 and R 4 is independently hydrogen or a linear hydrocarbyl group containing 1 to 5, or 1 to 2 carbon atoms (typically R 3 and R 4 are both hydrogen);
  • each R 5 is independently hydrogen or a linear hydrocarbyl group containing 1 to 10, or 1 to 5, or 1 to 2 carbon atoms (typically R 5 may be methyl or hydrogen, or R 5 may be hydrogen); and
  • n 1 to 20, or 3 to 15, or 4 to 8, or 6 to 8.
  • the compound of formula (1) during preparation, may have a portion of compounds that alkylate phenol at the ortho- position relative to a hydroxy group of phenol. Compounds having alkylated ortho- substitution may then couple at the para-position relative to the hydroxyl group. Consequently, a person skilled in the art will realize that compounds of this type are also encompassed by the present invention.
  • a portion of phenol groups may not be alkyated; and, if incorporated into the structure of formula (1), would contain a portion of unsubstituted phenol in formula (1).
  • the phenol may contain lower alkylated impurities (e.g., methyl, or ethyl, or propyl groups) that may also become incorporated into the structure of formula (1). Consequently, a person skilled in the art will realize that compounds of this type are also encompassed by the present invention.
  • lower alkylated impurities e.g., methyl, or ethyl, or propyl groups
  • the compound of formula (1) as defined above is the dominant product (typically present at least 50 mole % or at least 70 mole %) in the reaction to prepare compounds of the present invention.
  • the invention provides a method of lubricating a driveline device comprising supplying to the driveline device a lubricating composition comprising an oil of lubricating viscosity and a compound represented by formula (l a):
  • each R 1 is independently hydrogen or a linear hydrocarbyl group containing at least 1 , or at least 3 , or at least 4, or at least 6, or at least 8, or at least 10 carbon atoms (typically R 1 is a linear hydrocarbyl group containing at least 1 carbon atoms); and each R is independently a linear hydrocarbyl group containing at least 10, or at least 12, or at least 14, or at least 16 carbon atoms (R may contain carbon atoms in the range of 16 to 50, or 16 to 40, or 16 to 30, or 18 to 24).
  • the mechanical device may be an axle gear or a manual transmission (typically a manual transmission).
  • the lubricating composition may have a SAE viscosity grade from XW-Y, wherein X is 70, 75, 80 or 85 and Y is 80, 85, 90, or 140. Typically, Y is greater than X.
  • the oil of lubricating viscosity may be bright stock.
  • the bright stock may be present from 10 wt % to 97 wt %, or 20 wt % to 95 wt %, or 80 wt % to 95 wt % of the lubricating composition.
  • the invention provides for the use of a lubricating composition comprising an oil of lubricating viscosity and a compound of formula (1) as at least one of a filterability aid and a wax crystal growth/gelation inhibitor (may also be referred to as a wax crystal growth modifier/gelation modifier) in a driveline device (typically a manual transmission), wherein the compound of formula (1) is represented by:
  • the present invention provides a method and use as disclosed herein.
  • the compound of the invention may be represented by the formula (1) herein, wherein R 1 may be hydrogen; R 2 may be a linear hydrocarbyl group containing at least 10 carbon atoms (typically 10 to 100, or 16 to 70, or 16 to 40 carbon atoms); R 3 and R 4 may be hydrogen; R 5 may be hydrogen; and n may be 4 to 8, or 6 to 8.
  • the compound of the invention may be represented by the formula (1) described herein, wherein R 1 may independently be a linear hydrocarbyl group containing at least 1 (or at least 3, or at least 6) carbon atoms; R may be a linear hydrocarbyl group containing at least 10 carbon atoms (typically R may contain carbon atoms in the range of 10 to 60, or 16 to 50, or 16 to 40, or 16 to 30, or 18 to 24, or 20 to 28, or 22 to 26); R 3 and R 4 may be hydrogen; R 5 may be hydrogen; and n may be 1 to 20, or 3 to 15, or 4 to 8, or 6 to 8.
  • R 1 and R 2 may be derived from an olefin or polyolefin (typically an olefin), where the polyolefin or olefin is reacted with a phenol to form the hydrocarbyl-substituted phenol of the present invention.
  • an olefin or polyolefin typically an olefin
  • Examples of a suitable olefin include dodecene, tetradecene, hexade- cene, octadecene, eicosene, doeicosene, tetraeicosene, hexaeicosene or octaeico- sene, or mixtures thereof.
  • the olefin may be a mixture of 15 to 18, or 16 to 18, or 16 to 22, or 24 to 28, or 26 to 30 carbon atoms. In one embodiment the olefin may be a mixture of 24 to 28 carbon atoms.
  • the carbon atom bonded to both R 1 and R 2 may be a carbon atom of the olefin.
  • the structural unit R 1 R 2 HC-, the point of attachment to the phenol ring in the formula above may vary the number of carbon
  • the resultant product may have R 1 having 9 carbon atoms, R 2 having 10 carbon atoms and it may be represented by formula (2):
  • the resultant product may have R 1 having 8 carbon atoms, R 2 having 1 1 carbon atoms, or R 1 having 5 carbon atoms, R2 having 14 carbon atoms, or R 1 having 3 carbon atoms, R2 having 16 carbon atoms, R 1 having 1 carbon atoms, R having 18 carbon atoms and so on.
  • the carbocation is more stable if it is a secondary carbocation (rather than a primary carbocation) there is likely to be a tendency for the carbocation to react when in a more central (or internal) position.
  • the compound of the invention may be considered as a mixture of varying
  • hydrocarbyl groups represented by the structural unit R R HC- Often the carbocation may favour one end of the hydrocarbyl group such as at the second, third, fourth or fifth carbon.
  • the mole percent of compounds defined by formula (1) that is, in which R 1 is H or Ci or higher may be at least 30 mole percent, or at least 40 mole percent, or at least 45 mole percent, or at least 50 mole percent of molecules formed during preparation of compounds of the invention.
  • the mole percent of compounds of formula (1) may be 30 to 99.9 mole percent, or 40 to 90 mole percent, or 55 to 75 mole percent of molecules formed during preparation of compounds of the invention.
  • the attachment of a hydrocarbyl group to the phenol group of the compound of the invention may be accomplished by a number of techniques well known to those skilled in the art, for example, a Friedel-Crafts reaction.
  • the Friedel-Crafts reaction may react an olefin (e.g., a polymer containing an olefinic bond), or halogenated or hydrohalogenated derivative thereof, with a phenol in the presence of a Lewis acid catalyst.
  • Methods and conditions for carrying out such reactions are well known to those skilled in the art. See, for example, the discussion in the article entitled, "Alkylation of Phenols" in "Kirk-Othmer Encyclopedia of Chemical Technology", Third Edition, Vol. 2, pages 65 -66, Interscience Publishers.
  • the compound of the invention may be prepared by known processes to prepare novolak chemistry.
  • the compound may be prepared by reacting an aromatic hydroxy-substituted compound and an aldehyde.
  • International publication WO 2009/064827, and U.S. Patents 5,707,946; 5, 171,330; 4,565,460; 4,559, 155; 4,575,526; 4,613,342; 5,039,437 and 5,082,470 all disclose methods of preparing aromatic hydroxy-substituted compounds.
  • the aldehyde may have 1 to 5 or 1 to 2 carbon atoms.
  • suitable aldehyde include formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, and pentanal.
  • Formaldehyde may be supplied as a solution, but is more commonly used in the polymeric form, as paraformaldehyde.
  • Polymeric aldehydes, such as paraformaldehyde may be considered a reactive equivalent of, or a source for, an aldehyde.
  • Aqueous solutions of aldehydes such as formalin may also be considered a reactive equivalent of, or a source for, an aldehyde.
  • the compound may be present in the lubricating composition in a range including 100 ppm to 2000 ppm, or 200 ppm to 1000 ppm, or 300 ppm to 750 ppm or 400 ppm to 600 ppm.
  • the lubricating composition comprises an oil of lubricating viscosity.
  • the oil of lubricating viscosity in one embodiment includes bright stock.
  • the oil of lubricating viscosity may include oils such as natural and synthetic oils, oil derived from hydrocracking, hydrogenation, and hydrofinishing, unrefined, refined, re-refined oils or mixtures thereof.
  • oils such as natural and synthetic oils, oil derived from hydrocracking, hydrogenation, and hydrofinishing, unrefined, refined, re-refined oils or mixtures thereof.
  • a more detailed description of unrefined, refined and re -refined oils is provided in International Publication WO2008/147704, paragraphs [0054] to [0056].
  • a more detailed description of natural and synthetic lubricating oils is described in paragraphs [0058] to [0059] respectively of WO2008/147704.
  • Synthetic oils may also be produced by Fischer-Tropsch reactions and typically may be hydroisom- erised Fischer-Tropsch hydrocarbons or waxes.
  • oils may be prepared by a Fischer-Tropsch gas-to-liquid synthetic procedure as well as other gas-to-liquid oils.
  • Oils of lubricating viscosity may also be defined as specified in April 2008 version of "Appendix E - API Base Oil Interchangeability Guidelines for Passenger Car Motor Oils and Diesel Engine Oils", section 1.3 Sub-heading 1.3. "Base Stock Categories”.
  • the oil of lubricating viscosity may be an API Group II or Group III oil.
  • the oil of lubricating viscosity may be an API Group III base oil (typically including hydrocracked/hydroisomerized base oil).
  • the amount of the oil of lubricating viscosity present is typically the balance remaining after subtracting from 100 wt % the sum of the amount of the compound of the invention and the other performance additives.
  • the lubricating composition may be in the form of a concentrate and/or a fully formulated lubricant. If the lubricating composition of the invention (comprising the additives disclosed herein) is in the form of a concentrate which may be combined with additional oil to form, in whole or in part, a finished lubricant), the ratio of the of these additives to the oil of lubricating viscosity and/or to diluent oil include the ranges of 1 :99 to 99: 1 by weight, or 80:20 to 10:90 by weight.
  • the lubricating composition described herein optionally further includes at least one other performance additives.
  • the other performance additives include at least one of metal deactivators, detergents, dispersants, viscosity modifiers, friction modifiers, corrosion inhibitors, dispersant viscosity modifiers, antiwear agents, extreme pressure agents, antiscuffing agents, antioxidants, foam inhibitors, demulsifiers, pour point depressants (other than the compound of formula (1)), seal swelling agents and mixtures thereof.
  • fully-formulated lubricating oil will contain one or more of these performance additives.
  • Dispersants include for example an N-substituted long chain alkenyl succinimide, a Mannich base, or mixtures thereof.
  • N- substituted long chain alkenyl succinimides include polyisobutylene succini- mides, wherein the polyisobutylene from which it is derived has a number average molecular weight in the range 350 to 5000, or 500 to 3000, or 750 to 1 150.
  • the dispersants may also be post-treated by conventional methods by a reaction with any of a variety of agents.
  • agents such as boric acid, urea, thiourea, dimercaptothiadiazoles, carbon disulphide, aldehydes, ketones, carboxylic acids such as terephthalic acid, hydrocarbon- substituted succinic anhydrides, maleic anhydride, nitriles, epoxides, and phosphorus compounds.
  • the post-treated dispersant is borated.
  • the post-treated dispersant is reacted with dimercap- tothiadiazoles.
  • Detergents are known and include neutral or overbased detergents, i.e., ones prepared by conventional processes known in the art.
  • Suitable detergent substrates include, phenates, sulphur containing phenates, sulphonates, salix- arates, salicylates, carboxylic acids, phosphorus acids, alkyl phenols, sulphur coupled alkyl phenol compounds, or saligenins.
  • the detergent includes a magnesium or calcium sulphonate, or mixtures thereof.
  • Antioxidant compounds include sulphurised olefins, diphenylamines (such as dinonyl diphenylamine), hindered phenols, molybdenum dithiocarbamates, and mixtures thereof. Antioxidant compounds may be used alone or in combination.
  • the hindered phenol antioxidant often contains a secondary butyl and/or a tertiary butyl group as a sterically hindering group.
  • the phenol group is often further substituted with a hydrocarbyl group and/or a bridging group linking to a second aromatic group.
  • hindered phenol antioxidants examples include 2,6-di-tert-butylphenol, 4-methyl-2,6-di-tert-butylphenol, 4- ethyl-2,6-di-tert-butylphenol, 4-propyl-2,6-di-tert-butylphenol or 4-butyl-2,6-di- tert-butylphenol, or 4-dodecyl-2,6-di-tert-butylphenol.
  • the hindered phenol antioxidant may be an ester and may include, e.g., IrganoxTM L- 135 from Ciba.
  • molybdenum dithiocarbamates which may be used as an antioxidant include commercial materials sold under the trade names such as Vanlube 822TM and MolyvanTM A from R. T. Vanderbilt Co., Ltd., and Adeka Sakura-LubeTM S-100, S-165 and S-600 from Asahi Denka Kogyo K. K and mixtures thereof.
  • the lubricating composition may optionally further contain other known viscosity modifiers.
  • the viscosity modifiers may be hydrogenated styrene -butadiene rubbers, ethylene-propylene copolymers, hydrogenated styrene-isoprene polymers, hydrogenated diene polymers, polyalkyl styrenes, polyolefins, esters of maleic anhydride-styrene copolymers, or mixtures thereof.
  • the lubricating composition optionally further includes at least one antiwear agent.
  • suitable antiwear agents include oil soluble amine salts of phosphorus compounds, sulphurised olefins, metal dihydrocarbyldithiophosp hates (such as zinc dialkyldithiophosphates), thiocarbamate-containing compounds such as thiocarbamate esters, thiocarbamate amides, thiocarbamic ethers, alkylene- coupled thiocarbamates, and bis(S-alkyldithiocarbamyl) disulp hides.
  • the oil soluble phosphorus amine salt antiwear agent includes an amine salt of a phosphorus acid ester or mixtures thereof.
  • the amine salt of a phosphorus acid ester may include phosphoric acid esters and amine salts thereof; dialkyldithiophosphoric acid esters and amine salts thereof; amine salts of phosphites; and amine salts of phosphorus-containing carboxylic esters, ethers, and amides; and mixtures thereof.
  • the amine salt of a phosphorus acid ester may be used alone or in combination.
  • the oil soluble phosphorus amine salt includes partial amine salt-partial metal salt compounds or mixtures thereof.
  • the phosphorus compound further includes a sulphur atom in the molecule.
  • the amine salt of the phosphorus compound may be ashless, i.e., metal-free (prior to being mixed with other components).
  • the amines which may be suitable for use as the amine salt include primary amines, secondary amines, tertiary amines, and mixtures thereof.
  • the amines include those with at least one hydrocarbyl group, or, in certain embodiments, two or three hydrocarbyl groups.
  • the hydrocarbyl groups may contain 2 to 30 carbon atoms, or in other embodiments 8 to 26, or 10 to 20, or 13 to 19 carbon atoms.
  • Primary amines include ethylamine, propylamine, butylamine, 2-ethylhexylamine, octylamine, and dodecylamine, as well as such fatty amines as n-octylamine, n-decylamine, n-dodecylamine, n-tetradecylamine, n-hexadecyl- amine, n-octadecylamine and oleyamine.
  • fatty amines include commercially available fatty amines such as "Armeen®” amines (products available from Akzo Chemicals, Chicago, Illinois), such as Armeen C, Armeen O, Armeen OL, Armeen T, Armeen HT, Armeen S and Armeen SD, wherein the letter designation relates to the fatty group, such as coco, oleyl, tallow, or stearyl groups.
  • suitable secondary amines include dimethylamine, di ethylamine, dipropylamine, dibutylamine, diamylamine, dihexylamine, diheptyl- amine, methylethylamine, ethylbutylamine and ethylamyl amine.
  • the secondary amines may be cyclic amines such as piperidine, piperazine and morpholine.
  • the amine may also be a tertiary-aliphatic primary amine.
  • the aliphatic group in this case may be an alkyl group containing 2 to 30, or 6 to 26, or 8 to 24 carbon atoms.
  • Tertiary alkyl amines include monoamines such as tert- butylamine, tert-hexylamine, 1 -methyl- 1 -amino -cyclohexane, tert-octylamine, tert-decylamine, tertdodecylamine, tert-tetradecylamine, tert-hexadecylamine, tert-octadecylamine, tert-tetracosanylamine, and tert-octacosanylamine.
  • the phosphorus acid amine salt includes an amine with C I 1 to C 14 tertiary alkyl primary amino groups or mixtures thereof. In one embodiment the phosphorus acid amine salt includes an amine with C 14 to C 18 tertiary alkyl primary amines or mixtures thereof. In one embodiment the phosphorus acid amine salt includes an amine with C 18 to C22 tertiary alkyl primary amines or mixtures thereof.
  • amines may also be used in the invention.
  • a useful mixture of amines is "Primene® 81R” or “Primene® JMT.”
  • Primene® 81R and Primene® JMT are mixtures of C I 1 to C 14 tertiary alkyl primary amines and C 18 to C22 tertiary alkyl primary amines respectively.
  • oil soluble amine salts of phosphorus compounds include a sulphur-free amine salt of a phosphorus-containing compound which may be obtained/obtainable by a process comprising: reacting an amine with either (i) a hydroxy-substituted di-ester of phosphoric acid, or (ii) a phosphorylated hydroxy- substituted di- or tri- ester of phosphoric acid.
  • a process comprising: reacting an amine with either (i) a hydroxy-substituted di-ester of phosphoric acid, or (ii) a phosphorylated hydroxy- substituted di- or tri- ester of phosphoric acid.
  • the hydrocarbyl amine salt of an alkylphosphoric acid ester is the reaction product of a C 14 to C 18 alkylated phosphoric acid with Primene 81RTM.
  • hydrocarbyl amine salts of dialkyldithiophosphoric acid esters include the reaction product(s) of isopropyl, methyl-amyl (4-methyl-2- pentyl or mixtures thereof), 2-ethylhexyl, heptyl, octyl or nonyl dithiophosphoric acids with ethylene diamine, morpholine, or Primene 81RTM, and mixtures thereof.
  • the dithiophosphoric acid may be reacted with an epoxide or a glycol. This reaction product is further reacted with a phosphorus acid, anhydride, or lower ester.
  • the epoxide includes an aliphatic epoxide or a styrene oxide. Examples of useful epoxides include ethylene oxide, propylene oxide, butene oxide, octene oxide, dodecene oxide, and styrene oxide. In one embodiment the epoxide may be propylene oxide.
  • the glycols may be aliphatic glycols having from 1 to 12, or from 2 to 6, or 2 to 3 carbon atoms.
  • dithiophosphoric acids glycols, epoxides, inorganic phosphorus reagents and methods of reacting the same are described in U.S. Patent numbers 3,197,405 and 3,544,465.
  • the resulting acids may then be salted with amines.
  • An example of suitable dithiophosphoric acid is prepared by adding phosphorus pentoxide (about 64 grams) at 58 °C over a period of 45 minutes to 514 grams of hydroxypropyl 0,0-di(4-methyl-2-pentyl)phosphorodithioate (prepared by reacting di(4-methyl- 2-pentyl)-phosphorodithioic acid with 1.3 moles of propylene oxide at 25 °C).
  • the mixture may be heated at 75 °C for 2.5 hours, mixed with a diatomaceous earth and filtered at 70 °C.
  • the filtrate contains 1 1.8% by weight phosphorus, 15.2% by weight sulphur, and an acid number of 87 (bromophenol blue).
  • the dithiocarbamate-containing compounds may be prepared by reacting a dithiocarbamate acid or salt with an unsaturated compound.
  • the dithiocarbamate containing compounds may also be prepared by simultaneously reacting an amine, carbon disulphide and an unsaturated compound. Generally, the reaction occurs at a temperature from 25 °C to 125 °C.
  • Suitable olefins that may be sulphurised to form an the sulphurised olefin include propylene, butylene, isobutylene, pentene, hexane, heptene, octane, nonene, decene, undecene, dodecene, undecyl, tridecene, tetrad e- cene, pentadecene, hexadecene, heptadecene, octadecene, nonadecene, eicosene or mixtures thereof.
  • hexadecene, heptadecene, octadecene, eicosene or mixtures thereof and their dimers, trimers and tetramers are especially useful olefins.
  • the olefin may be a Diels-Alder adduct of a diene such as 1 ,3 -butadiene and an unsaturated ester, such as butyl acrylate.
  • Another class of sulphurised olefin includes fatty acids and their esters.
  • the fatty acids are often obtained from vegetable oil or animal oil; and typically contain 4 to 22 carbon atoms.
  • suitable fatty acids and their esters include triglycerides, oleic acid, linoleic acid, palmitoleic acid or mixtures thereof.
  • the fatty acids are obtained from lard oil, tall oil, peanut oil, soybean oil, cottonseed oil, sunflower seed oil or mixtures thereof.
  • fatty acids and/or ester are mixed with olefins.
  • the ashless antiwear agent may be a monoester of a polyol and an aliphatic carboxylic acid, often an acid containing 12 to 24 carbon atoms.
  • the monoester of a polyol and an aliphatic carbox- ylic acid is in the form of a mixture with a sunflower oil or the like, which may be present in the friction modifier mixture from 5 to 95, in several embodiments from 10 to 90, or from 20 to 85, or 20 to 80 weight percent of said mixture.
  • the aliphatic carboxylic acids (especially a monocarboxylic acid) which form the esters are those acids typically containing 12 to 24, or from 14 to 20 carbon atoms. Examples of carboxylic acids include dodecanoic acid, stearic acid, lauric acid, behenic acid, and oleic acid.
  • Polyols include diols, triols, and alcohols with higher numbers of alcoholic OH groups.
  • Polyhydric alcohols include ethylene glycols, including di-, tri- and tetraethylene glycols; propylene glycols, including di-, tri- and tetrapropylene glycols; glycerol; butane diol; hexane diol; sorbitol; arabitol; mannitol; sucrose; fructose; glucose; cyclohexane diol; erythritol; and penta- erythritols, including di- and tripentaerythritol.
  • the polyol is diethylene glycol, triethylene glycol, glycerol, sorbitol, penta erythritol or dipentaerythritol.
  • the commercially available monoester known as "glycerol monoo- leate” is believed to include 60 + 5 percent by weight of the chemical species glycerol monooleate, along with 35 + 5 percent glycerol dioleate, and less than 5 percent trioleate and oleic acid.
  • the amounts of the monoesters, described above, are calculated based on the actual, corrected, amount of polyol monoester present in any such mixture.
  • EP agents that are soluble in the oil include sulphur- and chlorosulphur-containing EP agents, chlorinated hydrocarbon EP agents and phosphorus EP agents.
  • EP agents include chlorinated wax; sulphurised olefins (such as sulphurised isobutylene), organic sulphides and polysulphides such as dibenzyldisulphide, bis-(chlorobenzyl) disulphide, dibutyl tetrasulphide, sulphurised methyl ester of oleic acid, sulphurised alkylphenol, sulphurised dipentene, sulphurised terpene, and sulphurised Diels-Alder adducts; phosphosulphurised hydrocarbons such as the reaction product of phosphorus sulphide with turpentine or methyl oleate; phosphorus esters such as the dihydrocarbon and trihydrocarbon phosphites,
  • Corrosion inhibitors that may be useful in the compositions of the invention include fatty amines, octyl octanamide, condensation products of dodecenyl succinic acid or anhydride and/or a fatty acid such as oleic acid with a polyamine.
  • Foam inhibitors that may be useful in the compositions of the invention include copolymers of ethyl acrylate and 2-ethylhexylacrylate and optionally vinyl acetate; demulsifiers including trialkyl phosphates, polyethylene glycols, polyethylene oxides, polypropylene oxides and (ethylene oxide -propylene oxide) polymers.
  • pour point depressants may include polyalphaolefins, esters of maleic anhydride -styrene copolymers, poly(meth)acrylates, polyacrylates or polyacrylamides.
  • the pour point depressant may be (i) esters of maleic anhydride -styrene copolymers, or (ii) polymethacrylates.
  • the pour point depressant may be present at 0 wt % to 0.5 wt %, or 0.1 wt % to 0.4 wt % of the lubricating composition.
  • Friction modifiers that may be useful in the compositions of the invention include fatty acid or fatty alkyl derivatives such as amines, esters, epoxides, fatty imidazolines, condensation products of carboxylic acids and polyalkylene-polyamines and amine salts of alkylphosphoric acids.
  • a suitable lubricating composition includes the compound of the formula disclosed herein that may be present (on an actives basis) in ranges as shown in the following table.
  • Preparative Example 1 A 3L flask under nitrogen is charged with a C 2 4_28 alkylphenol (lOOOg, 2.222 mol) and heated to 85 °C. Sulphuric acid (3.46 g) is added dropwise over approximately 10 minutes. The flask is then heated to 105 °C and paraformal- dehyde (81.6 g, 2.717 mol) is charged over four hours. The flask is then heated to 135 °C over two hours and then held at this temperature for a further two hours to collect any aqueous distillate.
  • Sulphuric acid 3.46 g
  • paraformal- dehyde 81.6 g, 2.717 mol
  • the reaction is then cooled to 121 °C and solid calcium hydroxide (3.16 g) charged to the flask, followed by a 50% aqueous solution of sodium hydroxide 30 minutes later.
  • the flask is then held at 121 °C for two hours, then heated to 152°C and held there for a further two hours with a high nitrogen sparge to quench the reaction and collect any additional/remaining aqueous distillate.
  • the flask is then cooled to about 70°C and an aromatic solvent (SolvessoTM 150, 1022 g) charged to the flask. After 30 minutes the mixture is discharged and filtered to give a dark oil.
  • Comparative lubricant 1 is a manual transmission lubricant comprising 7 wt % of a commercially available additive package, 400 ppm of a vinyl acetate copolymer (commercially available from The Lubrizol Corporation under the trade name LZ®8056F, 0.3 wt % of a pour point depressant (derived from a polymefhacrylate) and the balance to 100 wt % with bright stock lubricant.
  • Comparative lubricant 2 is a manual transmission lubricant comprising 7 wt % of a commercially available additive package, 400 ppm of the material of Example 1 of International publication WO 2009/064827, and the balance to 100 wt % with bright stock lubricant.
  • Inventive lubricant 1 is a manual transmission lubricant comprising 7 wt % of a commercially available additive package, 400 ppm of the product of preparative example 1 , 0.3 wt % of a pour point depressant (derived from an esterified maleic anhydride styrene), and the balance to 100 wt % with bright stock lubricant.
  • Lubricants COMPL1 , COMPL2 and INVL1 are evaluated to determine filterability by the methodology described in ISO Standard IS013357-2: 1998(E), except the filter pressure is 2 bar (or 200 kPa) and a 5 ⁇ membrane is used.
  • Stage 2 filterability (as noted in section 4.3 of the procedure) is a ratio expressed as a percent- age between the flow rate at the start of the filtration and the flow rate between 200 ml and 300 ml of filtered volume. The ratio is calculated by the formula given in section 10.2 of the procedure. The results obtained are:
  • Unfilterable indicates that the filtration time exceeds 7200 seconds.
  • hydrocarbyl substituent or “hydrocarbyl group” is used in its ordinary sense, which is well-known to those skilled in the art. Specifically, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character.
  • hydrocarbyl groups include: hydrocarbon substituents, including aliphatic, alicyclic, and aromatic substituents; substituted hydrocarbon substitu- ents, that is, substituents containing non-hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon nature of the substituent; and hetero substituents, that is, substituents which similarly have a predominantly hydrocarbon character but contain other than carbon in a ring or chain.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

La présente invention concerne un procédé de lubrification d'un organe de transmission consistant à fournir à l'organe de transmission une composition lubrifiante comprenant une huile visqueuse et un composé aromatique à substitution hydroxy. L'invention concerne également l'utilisation de la composition lubrifiante comprenant le composé aromatique à substitution aromatique comme au moins une aide à la filtrabilité, un modificateur de croissance/inhibiteur de gélification des cristaux de paraffine dans l'organe de transmission.
PCT/US2010/058820 2009-12-07 2010-12-03 Procédé de lubrification d'une boîte de vitesses à commande manuelle WO2011071756A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP10788468.6A EP2510078B1 (fr) 2009-12-07 2010-12-03 Methode de lubrifier un transmission manuel
US13/513,661 US20120302479A1 (en) 2009-12-07 2010-12-03 Method of Lubricating a Manual Transmission

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US26714309P 2009-12-07 2009-12-07
US61/267,143 2009-12-07

Publications (1)

Publication Number Publication Date
WO2011071756A1 true WO2011071756A1 (fr) 2011-06-16

Family

ID=43640257

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/058820 WO2011071756A1 (fr) 2009-12-07 2010-12-03 Procédé de lubrification d'une boîte de vitesses à commande manuelle

Country Status (3)

Country Link
US (1) US20120302479A1 (fr)
EP (1) EP2510078B1 (fr)
WO (1) WO2011071756A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017106255A1 (fr) * 2015-12-15 2017-06-22 Donaldson Company, Inc. Système de filtrabilité de fluide hydrocarbure

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8980803B2 (en) 2013-03-12 2015-03-17 Exxonmobil Research And Engineering Company Lubricant base stocks with improved filterability
US11680222B2 (en) * 2020-10-30 2023-06-20 Afton Chemical Corporation Engine oils with low temperature pumpability

Citations (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1147799B (de) 1959-08-03 1963-04-25 Exxon Research Engineering Co Erdoeldestillat-Treib- bzw. -Brennstoff
US3197405A (en) 1962-07-09 1965-07-27 Lubrizol Corp Phosphorus-and nitrogen-containing compositions and process for preparing the same
US3544465A (en) 1968-06-03 1970-12-01 Mobil Oil Corp Esters of phosphorodithioates
EP0111883A1 (fr) 1982-12-23 1984-06-27 Hoechst Aktiengesellschaft Utilisation de copolymères d'éthylène comme additifs pour les huiles minérales
US4559155A (en) 1982-08-09 1985-12-17 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4565460A (en) 1984-03-05 1986-01-21 Kline Alva C Convex key top configurations
US4575526A (en) 1982-08-09 1986-03-11 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same
EP0184083A2 (fr) 1984-11-29 1986-06-11 Hoechst Aktiengesellschaft Terpolymères de l'éthylène, leur procédé de fabrication et leur application
US4613342A (en) 1982-08-09 1986-09-23 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
EP0203554A1 (fr) 1985-05-29 1986-12-03 Hoechst Aktiengesellschaft Utilisation de terpolymères d'éthylène, comme additifs pour huiles minérales et distillats d'huiles minérales
US5039437A (en) 1987-10-08 1991-08-13 Exxon Chemical Patents, Inc. Alkyl phenol-formaldehyde condensates as lubricating oil additives
US5082470A (en) 1987-10-08 1992-01-21 Exxon Chemical Patents Inc. Alkyl phenol-formaldehyde condensates as fuel additives
WO1992007047A1 (fr) * 1990-10-10 1992-04-30 Exxon Chemical Patents Inc. Procede de preparation de condensats de phenole alkyle-formaldehyde
US5171330A (en) 1990-06-08 1992-12-15 Societa' Italiana Additivi Per Carburanti Compositions of refinery hydrocarbons endowed with improved fluidity at low temperatures containing methacyclophanes
US5707946A (en) 1996-04-08 1998-01-13 The Lubrizol Corporation Pour point depressants and their use
US6495495B1 (en) 1999-08-20 2002-12-17 The Lubrizol Corporation Filterability improver
US20080182770A1 (en) 2007-01-26 2008-07-31 The Lubrizol Corporation Antiwear Agent and Lubricating Compositions Thereof
WO2008147704A1 (fr) 2007-05-24 2008-12-04 The Lubrizol Corporation Composition lubrifiante contenant un agent anti-usure
WO2009064827A1 (fr) 2007-11-16 2009-05-22 The Lubrizol Corporation Nouveaux matériaux couplés à base de phénol substitué par un groupe hydrocarbyle en tant qu'inhibiteurs de cires de champ pétrolifère

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5817605A (en) * 1991-06-03 1998-10-06 Ethyl Petroleum Additives, Inc. Automatic transmission and wet brake fluids and additive package therefor
JPH11116982A (ja) * 1997-10-09 1999-04-27 Mitsubishi Oil Co Ltd 潤滑油組成物
JP3501275B2 (ja) * 1998-11-26 2004-03-02 出光興産株式会社 自動変速機用潤滑油組成物
US7141157B2 (en) * 2003-03-11 2006-11-28 Chevron U.S.A. Inc. Blending of low viscosity Fischer-Tropsch base oils and Fischer-Tropsch derived bottoms or bright stock
CA2509735C (fr) * 2004-06-11 2012-09-25 Infineum International Limited Additifs detergents pour compositions d'huile lubrifiante
US20060046941A1 (en) * 2004-08-26 2006-03-02 Laurent Chambard Lubricating oil compositions
US7732390B2 (en) * 2004-11-24 2010-06-08 Afton Chemical Corporation Phenolic dimers, the process of preparing same and the use thereof
DE102005035275B4 (de) * 2005-07-28 2007-10-11 Clariant Produkte (Deutschland) Gmbh Mineralöle mit verbesserter Leitfähigkeit und Kältefließfähigkeit
JP5062650B2 (ja) * 2005-07-29 2012-10-31 東燃ゼネラル石油株式会社 ギヤ油組成物
US7582591B2 (en) * 2006-04-07 2009-09-01 Chevron U.S.A. Inc. Gear lubricant with low Brookfield ratio

Patent Citations (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1147799B (de) 1959-08-03 1963-04-25 Exxon Research Engineering Co Erdoeldestillat-Treib- bzw. -Brennstoff
US3197405A (en) 1962-07-09 1965-07-27 Lubrizol Corp Phosphorus-and nitrogen-containing compositions and process for preparing the same
US3544465A (en) 1968-06-03 1970-12-01 Mobil Oil Corp Esters of phosphorodithioates
US4559155A (en) 1982-08-09 1985-12-17 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4575526A (en) 1982-08-09 1986-03-11 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same
US4613342A (en) 1982-08-09 1986-09-23 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
EP0111883A1 (fr) 1982-12-23 1984-06-27 Hoechst Aktiengesellschaft Utilisation de copolymères d'éthylène comme additifs pour les huiles minérales
US4565460A (en) 1984-03-05 1986-01-21 Kline Alva C Convex key top configurations
EP0184083A2 (fr) 1984-11-29 1986-06-11 Hoechst Aktiengesellschaft Terpolymères de l'éthylène, leur procédé de fabrication et leur application
EP0203554A1 (fr) 1985-05-29 1986-12-03 Hoechst Aktiengesellschaft Utilisation de terpolymères d'éthylène, comme additifs pour huiles minérales et distillats d'huiles minérales
US5039437A (en) 1987-10-08 1991-08-13 Exxon Chemical Patents, Inc. Alkyl phenol-formaldehyde condensates as lubricating oil additives
US5082470A (en) 1987-10-08 1992-01-21 Exxon Chemical Patents Inc. Alkyl phenol-formaldehyde condensates as fuel additives
US5171330A (en) 1990-06-08 1992-12-15 Societa' Italiana Additivi Per Carburanti Compositions of refinery hydrocarbons endowed with improved fluidity at low temperatures containing methacyclophanes
WO1992007047A1 (fr) * 1990-10-10 1992-04-30 Exxon Chemical Patents Inc. Procede de preparation de condensats de phenole alkyle-formaldehyde
US5707946A (en) 1996-04-08 1998-01-13 The Lubrizol Corporation Pour point depressants and their use
US6495495B1 (en) 1999-08-20 2002-12-17 The Lubrizol Corporation Filterability improver
US20080182770A1 (en) 2007-01-26 2008-07-31 The Lubrizol Corporation Antiwear Agent and Lubricating Compositions Thereof
WO2008147704A1 (fr) 2007-05-24 2008-12-04 The Lubrizol Corporation Composition lubrifiante contenant un agent anti-usure
US20100197536A1 (en) 2007-05-24 2010-08-05 Mosier Patrick E Lubricating Composition Containing Ashfree Antiwear Agent Based on Hydroxypolycarboxylic Acid Derivative and a Molybdenum Compound
WO2009064827A1 (fr) 2007-11-16 2009-05-22 The Lubrizol Corporation Nouveaux matériaux couplés à base de phénol substitué par un groupe hydrocarbyle en tant qu'inhibiteurs de cires de champ pétrolifère

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Kirk-Othmer Encyclopedia of Chemical Technology", vol. 2, INTCRSCICNCC PUBLISHERS, article "Alkylation of Phenols", pages: 65 - 66

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017106255A1 (fr) * 2015-12-15 2017-06-22 Donaldson Company, Inc. Système de filtrabilité de fluide hydrocarbure

Also Published As

Publication number Publication date
US20120302479A1 (en) 2012-11-29
EP2510078A1 (fr) 2012-10-17
EP2510078B1 (fr) 2017-02-15

Similar Documents

Publication Publication Date Title
EP2021387B1 (fr) Nouveaux polymères et procédés de modulation de la viscosité
US8304374B2 (en) Antiwear agent and lubricating composition thereof
CN107109284B (zh) 用于润滑剂用途的混合磷酯
US9540585B2 (en) Lubricating composition containing an antiwear agent
US20120172265A1 (en) Lubricating Composition Containing a Compound Derived from a Hydroxy-carboxylic Acid
KR101941437B1 (ko) 내마모제를 함유하는 윤활 조성물
US20190177651A1 (en) Lubricant compositions comprising olefin copolymer dispersants in combination with additives
JP2009509027A (ja) 内燃機関を潤滑する方法
JP6055774B2 (ja) 官能化コポリマーおよびその潤滑組成物
AU2011349660B2 (en) Lubricating composition containing a detergent
AU2009274134B2 (en) Method of lubricating a tractor hydraulic
EP2467458A1 (fr) Composition anti-usure et procédé de lubrification d'un dispositif de transmission
WO2008021737A1 (fr) Procédé de lubrification d'un moteur à combustion interne
EP2510078B1 (fr) Methode de lubrifier un transmission manuel
EP2655579B1 (fr) Copolymeres functioalises et compositions lubrifiantes les contenantes

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10788468

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

REEP Request for entry into the european phase

Ref document number: 2010788468

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2010788468

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 13513661

Country of ref document: US