EP0523213B1 - Emulsionsspaltung von ölen - Google Patents

Emulsionsspaltung von ölen Download PDF

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Publication number
EP0523213B1
EP0523213B1 EP92903475A EP92903475A EP0523213B1 EP 0523213 B1 EP0523213 B1 EP 0523213B1 EP 92903475 A EP92903475 A EP 92903475A EP 92903475 A EP92903475 A EP 92903475A EP 0523213 B1 EP0523213 B1 EP 0523213B1
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EP
European Patent Office
Prior art keywords
anhydride
lubricating composition
oil
demulsifier
dicarboxylic acid
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.)
Expired - Lifetime
Application number
EP92903475A
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English (en)
French (fr)
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EP0523213A1 (de
Inventor
Alan Aries
Adrian Dunn
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ExxonMobil Chemical Patents Inc
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Exxon Chemical Patents Inc
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Publication of EP0523213A1 publication Critical patent/EP0523213A1/de
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    • C10M167/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound, a non-macromolecular compound and a compound of unknown or incompletely defined constitution, each of these compounds being essential
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    • 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
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/30—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms
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    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
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Definitions

  • the invention relates to improvements in oil compositions, particularly in lubricating oil compositions.
  • the invention has particular relevance to lubricating oils for marine engines, but is not limited thereto.
  • Oils for use in marine engines generally fall into one of three main classes, namely marine diesel cylinder lubricants (MDCLs) and trunk piston engine oils (TPEOs), and system oils.
  • MDCLs marine diesel cylinder lubricants
  • TPEOs trunk piston engine oils
  • system oils Under the crankcase conditions in which TPEOs are normally used (the presence of condensation, the possibility of water contamination, and the use of a lubricant purification system), there is a tendency for water to form an emulsion with the oil, which will normally contain a dispersant and a metal-containing detergent. Emulsion formation may also be a problem with system oils, although, as system oils normally contain less metal-containing detergent than TPEOs, or no metal-containing detergent at all, the tendency of system oils to form emulsions is generally lower than for TPEOs.
  • emulsions are undesirable, as an emulsion may interfere with the working of the oil and/or of parts of the engine, and/or the intimate association of the oil and the water in the emulsion may result in an increased tendency for additives in the oil to become dissolved or dispersed in the water and to be lost from the oil when the oil is purified by the removal of water. Further, the presence of an emulsion may also result in blocking of filters and reduced efficiency of centrifuges used in purification of the oil.
  • 4 398 921 discloses the use in fuels of a specified Mannich dispersant and a two-component demulsifying agent comprising a specified oil-soluble oxyalkylene polyether and a specified oxyalkylated phenol formaldehyde resin.
  • the fuels also contain a corrosion inhibitor which is a hydrocarbyl succinic acid or anhydride having from 12 to 30 carbon atoms.
  • European Specification No. 330 522 A discloses an oil-soluble mixture useful as an oil additive which comprises a specified lubricating oil ashless additive, a demulsifier additive comprising the reaction product of an alkylene oxide and an adduct of a bis-epoxide and a polyhydric alcohol, and a compatibility additive for enhancing the solubility of the demulsifier in the oil solutions in which it is used.
  • the compatibility additive comprises an alcohol, for example, a glycol, ester or hydroxyamide derivative of a carboxylic acid having a total of from 24 to 90 carbon atoms and at least one carboxylic group per molecule, preferred compatibility additives being dimer acid esters, the dimer acids being cyclohexene dicarboxylic acids formed from C18 to C22 unsaturated fatty acids.
  • the starting materials from which the demulsifiers are prepared include dicarboxylic acids or derivatives thereof, the acids/derivatives reacting with one or more other components during the preparation of the demulsifiers.
  • U.S. Specification No. 4 440 902 discloses the use of a bisester of an alkenylsuccinic anhydride of specified formula and an ethylene oxide/propylene oxide block polymer of specified formula as a demulsifier for oil-water emulsions.
  • U.S. Specification No. 4 885 110 discloses the use of the reaction product of specified proportions of an oxyalkylated primary fatty amine of specified formula, an at least trihydric oxyalkylated alkanol containing specified units, and a dicarboxylic acid/anhydride, as a demulsifier for breaking crude oil emulsions.
  • British Specification No. 2 008 146 A discloses a demulsifier for water-in-oil emulsions, especially water-in-crude oil emulsions, which comprises a polyester obtained by the condensation of an alk(en)yl succinic anhydride wherein the alk(en)yl group has 9 to 18 carbon atoms, a polyalkylene glycol of specified molecular weight and properties, and a polyhydric alcohol having three or more hydroxyl groups capable of reacting with the anhydride, the reactants being used in specified proportions.
  • U.S. Specification No. 4 705 834 discloses the use of crosslinked oxyalkylated polyalkylenepolyamines for breaking water-in-oil emulsions which occur in oil production.
  • the crosslinked compounds are prepared by crosslinking polyalkylene polyamines, which are completely oxyalkylated at the nitrogen atoms, with a crosslinking compound which possesses two or more functional groups which are capable of reacting with the terminal alcohol groups of the oxyalkylated polyalkylenepolyamines.
  • crosslinking compounds there are mentioned aliphatic and aromatic diisocyanates, dicarboxylic acids, diesters of dicarboxylic acids with lower alcohols, and bisglycidyl ethers of aliphatic and aromatic polyhydroxy compounds.
  • German Specification No. 3 635 489 A discloses demulsifiers for water-containing crude oils, the demulsifiers being formed by a process in which free hydroxyl groups in copolymers of (meth)acrylic esters of mixtures of polyglycols and polyglycol ethers with ethylenically unsaturated monomers are etherified, esterified or converted to urethane groups and/or an acid used as a catalyst is neutralised by addition of an amine.
  • European Specification No. 333 135 A discloses reaction products of (1) alkoxylated primary fatty amines, (2) adducts of ethylene oxide/propylene block copolymers and glycidyl ethers and (3) dicarboxylic acids.
  • the reaction products may be used as demulsifiers.
  • British Specification No. 1 186 659 discloses the use of demulsifiers, particularly polyoxyalkylene polyol block copolymers, in lubricating compositions containing dispersants comprising specified derivatives of succinic acids having a substituent containing at least fifty aliphatic carbon atoms.
  • the present invention provides the use of a free (as hereinafter defined) dicarboxylic acid or anhydride to enhance the action of a demulsifier for a water-in-oil emulsion containing an ashless dispersant additive, the demulsifier comprising a crosslinked polyoxyalkylene polyol.
  • the invention also provides a lubricating composition
  • a lubricating composition comprising an oil of lubricating viscosity, an ashless dispersant additive, a demulsifier comprising a crosslinked polyoxyalkylene polyol, and a free (as hereinafter defined) dicarboxylic acid or anhydride.
  • the invention further provides a lubricating composition
  • a lubricating composition comprising a blend of an oil of lubricating viscosity, a lubricating oil ashless dispersant additive, a demulsifier comprising a crosslinked polyoxyalkylene polyol, and a dicarboxylic acid or anhydride.
  • a lubricating composition in accordance with the invention may comprise one or more additional additives, particularly one or more overbased metal detergent additives and/or one or more zinc dihydrocarbyl dithiophosphates (ZDDPs).
  • additional additives particularly one or more overbased metal detergent additives and/or one or more zinc dihydrocarbyl dithiophosphates (ZDDPs).
  • ZDDPs zinc dihydrocarbyl dithiophosphates
  • the lubricating oil is suitable for marine use, particularly for use as a TPEO or a system oil, and is formulated using constituents, and proportions of constituents, appropriate to such use.
  • a lubricating oil suitable for use as a TPEO will normally contain at least one overbased metal detergent and at least one ZDDP, and will normally a Total Base Number (TBN) in the range of from 9 to 40.
  • TBN of a system oil will normally be in the range of from 0 to 6. All TBNs indicated in this specification are measured according to ASTM D2896.
  • the invention also provides a concentrate useful as an additive for a lubricating oil which concentrate comprises an ashless dispersant additive, a demulsifier comprising a crosslinked polyoxyalkylene polyol, a free (as hereinafter defined) dicarboxylic acid or anhydride, an overbased metal detergent, a ZDDP, and base oil.
  • a lubricating oil is a TPEO
  • the concentrate preferably has a TBN in the range of from 150 to 250.
  • the invention further provides a method for preparing a lubricating composition which comprises blending, in any order, an oil of lubricating viscosity, an ashless dispersant additive, a demulsifier and a free (as hereinafter defined) dicarboxylic acid or anhydride.
  • the demulsifier is preferably added to a mixture of the ashless dispersant additive, the dicarboxylic acid and the overbased metal detergent additive, and the ZDDP is then added to the mixture so obtained.
  • a demulsifier and a dicarboxylic acid/anhydride makes it possible to obtain oil compositions, particularly lubricating oil compositions, and especially TPEOs and system oils, with little or no tendency to form emulsions, even when used in the presence of water or water vapour.
  • a free dicarboxylic acid or anhydride is meant an acid or anhydride which is mixed as such with at least the first of the other components of the composition or blend.
  • the acid or anhydride is introduced as such into the vessel or other container in which a mixture of components is to be prepared.
  • dicarboxylic acids or anhydrides are used in the preparation of certain demulsifiers.
  • Dicarboxylic acid/anhydride-derived groups which are chemically incorporated in demulsifiers or other components by reaction at one or both of the carboxyl groups before the dicarboxylic acid/anhydride is blended with the ashless dispersant additive and the demulsifier used in accordance with the invention, or with whichever of the dispersant additive and the demulsifier is blended first with the acid/anhydride, are not free dicarboxylic acids/anhydrides.
  • the dicarboxylic acid used in accordance with the invention (or the dicarboxylic acid from which an anhydride used in accordance with the invention is derived) preferably has the general formula HO2C-(R)-CO2H wherein R represents a divalent hydrocarbyl group.
  • R represents a divalent hydrocarbyl group.
  • a hydrocarbyl group consists essentially of hydrogen and carbon atoms but may, if desired, contain other atoms as or in substituents or as chain members provided that the presence of such atoms or groups containing them does not result in undesired reactions occurring during the use of the dicarboxylic acid or anhydride.
  • the hydrocarbyl group may be, for example, a divalent aromatic group, but is advantageously a straight or branched chain, saturated or unsaturated, divalent aliphatic radical.
  • a divalent aromatic group but is advantageously a straight or branched chain, saturated or unsaturated, divalent aliphatic radical.
  • at most three chain atoms separate the two carboxyl groups, and, in preferred acids/anhydrides, the carboxyl groups are separated by two chain carbon atoms.
  • alk(en)yl succinic acids and anhydrides Especially advantageous for use in accordance with the invention are alk(en)yl succinic acids and anhydrides, the alk(en)yl radical preferably having 9 to 18 carbon atoms.
  • Anhydrides containing an alkenyl radical may be prepared, for example, by an addition reaction between a monoolefin and maleic acid or anhydride at an elevated temperature, usually in the presence of a catalyst; if desired, such acids or anhydrides can then be hydrogenated to give the corresponding alkyl compounds.
  • Straight or branched-chain mono-olefins may be used, although in some cases the branched-chain olefins may be preferred as giving liquid anhydrides.
  • Suitable monoolefins for use in preparing the succinic anhydrides are alpha-olefins, for example, those obtained from cracking wax.
  • suitable alpha-olefins are 1-dodecene, 1-tridecene, 1-tetradecene and 1-pentadecene.
  • Other suitable olefins are low molecular weight polymers of a C2 to C4 olefin (that is, an oligomer of a C2 to C4 olefin), examples of such oligomers being tetrapropylene, triisobutylene and tetraisobutylene.
  • a preferred alkenyl succinic anhydride is dodecenyl succinic anhydride (DDSA), especially the branched chain form thereof, tetrapropenyl succinic anhydride (TPSA).
  • the optimum amount of dicarboxylic acid/anhydride to be used for a particular oil will depend on the nature of the acid/anhydride and the nature and proportions of the other constituents of the oil, and can be determined by routine experiment.
  • the acid/anhydride and demulsifier will generally be used in a mass ratio of about 0.1:1 to 10:1, on an active ingredient basis, more specifically, 0.5:1 to 5:1.
  • a ratio in the range of from about 1:1 to 3:1 was found to be advantageous.
  • Mixtures of two or more acids or anhydrides, or at least one acid and at least one anhydride may of course be used.
  • the demulsifiers used in accordance with the invention comprise at least one crosslinked polyoxyalkylene polyol, and may also comprise one or more other constituents which, together with the crosslinked polyoxyalkylene polyol, impart demulsifying properties to the mixture.
  • polyoxyalkylene polyol any compound containing at least two oxyalkylene units and at least two hydroxyl groups.
  • crosslinked polyoxyalkylene polyol includes not only compounds made by reacting one or more polyoxyalkylene polyols with a crosslinking agent but also, for example, compounds in which a difunctional compound, for example, one of those mentioned below as being suitable for use as a crosslinked agent, is treated with one or more alkylene oxides to give a product containing at least two oxyalkylene chains.
  • Preferred demulsifiers for use in accordance with the invention are produced by reacting with a crosslinking agent a polyoxyalkylene polyol produced by reacting a polyol with one or more alkylene oxides or oxyalkylene mono- or copolymers.
  • Suitable polyols include, for example, alkylene glycols, alkylene triols and alkylene tetrols, for example, ethylene glycol, propylene glycol, dipropylene glycol, glycerol, and pentaerythritol.
  • Aromatic hydroxyl compounds for example, alkylated mono-and polyhydric phenols and naphthols can also be used.
  • the total number of carbon atoms in alkylene oxides from which oxyalkylene groups are derived advantageously does not exceed 10, and is preferably 2 to 4.
  • alkylene oxides are ethylene oxide, propylene oxide, 1,2-epoxy butane, 2,3-epoxy butane, 1,2-epoxy pentane, 2,3-epoxy pentane, 1,2-epoxy hexane, 2,3-epoxy hexane, 3,4-epoxy hexane, and 1,2-epoxy-3-methylbutane.
  • Particularly preferred alkylene oxides are ethylene oxide and propylene oxide.
  • the alkylene oxides may, if desired, contain non-hydrocarbon substituents provided that these do not interfere with the use of the alkylene oxides or demulsifiers derived therefrom.
  • a polyoxyalkylene polyol contains units derived from more than one alkylene oxide, these units may be randomly distributed (if a mixture of two or more different alkylene oxides is used) or in blocks (if different alkylene oxides are added sequentially to the reaction vessel).
  • block polymers are prepared, the nature of the alkylene oxides used in forming the blocks, and the number of repeating units, may be chosen by the person skilled in the art having regard to the properties desired for the block polymers.
  • oxypropylene blocks are normally relatively hydrophobic and oxyethylene blocks relatively hydrophilic.
  • Preferred polyoxyalkylene polyols from which crosslinked compounds for use in accordance with the invention may be derived are obtained by reacting dipropylene glycol or a triol with propylene oxide.
  • Crosslinking of polyoxyalkylene polyols may be effected using a crosslinking compound which possesses two or more functional groups which are capable of reacting with hydroxyl groups (normally terminal hydroxyl groups) in the polyoxyalkylene polyols.
  • Preferred crosslinking agents for use in preparing crosslinked polyoxyalkylene polyols for use in accordance with the invention are dicarboxylic acids and diglycidyl ethers of aliphatic and aromatic polyhydroxy compounds.
  • suitable dicarboxylic acids are glutaric acid and, preferably, adipic acid
  • suitable diglycidyl ethers are the diglycidyl ethers of the hydroxy compounds diphenylolmethane, pentaerythritol, trimethylolpropane, ethane-1,2-diol, propane-1,2-diol, butane-1,2-diol, butane-2,3-diol, glycerol and, especially, bisphenol A.
  • the demulsifier used in accordance with the invention may comprise one or more other constituents which, together with the crosslinked polyoxyalkylene polyol, impart demulsifying properties to the mixture.
  • suitable additional constituents are crosslinked polyoxyalkylene polyols which have been reacted with one or more alkylene oxides, for example ethylene oxide and/or propylene oxide, and esters of oxyalkylated phenol formaldehyde resins.
  • Examples of oxyalkylated phenol formaldehyde resins which may be esterified to give a demulsifier constituent for use in accordance with the invention are resins of the formula: wherein A represents an alkylene group containing from 2 to about 10 carbon atoms, m has an average value of from about 4 to about 200, R represents an alkyl group having 1 to about 20 carbon atoms, and x is an integer greater than 1.
  • A represents an alkylene group containing from 2 to about 10 carbon atoms
  • m has an average value of from about 4 to about 200
  • R represents an alkyl group having 1 to about 20 carbon atoms
  • x is an integer greater than 1.
  • the use of such resins as a demulsifier component is described in, for example, U.S. Specification No. 4 398 921 referred to above.
  • the group represented by R preferably has at least four carbon atoms and may be, for example, an isobutyl, tert.butyl or nonyl
  • a demulsifier constituent for use in accordance with the invention may be prepared by esterifying an oxyalkylated phenol formaldehyde resin with, for example, a monocarboxylic acid, advantageously a saturated or unsaturated, straight or branched chain, monocarboxylic acid, which acid preferably contains about 12 to 20 carbon atoms. Because of their ready availability, mixtures of acids containing C16 to C18 fatty acids are particularly preferred.
  • the demulsifier/dispersant mass ratio in a TPEO may be, for example, in the range of from about 0.001:1 to 0.1 : 1, more especially 0.002 : 1 to 0.07 : 1, calculated on an active ingredient basis.
  • the ashless dispersant additive for use in accordance with the invention may comprise an ashless dispersant and/or a viscosity index improver dispersant.
  • Suitable ashless dispersants for use in accordance with the invention include, for example, the reaction products of amines, including amino-alcohols, with a hydrocarbyl-substituted mono-or dicarboxylic acid or a derivative thereof, long chain aliphatic hydrocarbons having one or more polyamine molecules attached directly thereto as shown in, for example, U.S. Specifications Nos. 3 275 554 and 3 565 804 (in which the halogen group in a halogenated hydrocarbon is displaced using an alkylene polyamine), and Mannich condensation products containing a long chain hydrocarbyl group, for example as a substituent of a phenol.
  • Preferred ashless dispersant additives used in accordance with the invention comprise, for example, at least one member selected from the group consisting of:
  • the hydrocarbyl-substituted carboxylic acid or acid derivative comprises a hydrocarbon chain, generally a polyolefin chain, to which is grafted a substance containing at least one ethylenic bond and at least one carboxylic acid or anhydride group, or a polar group which is convertible into a carboxylic group by oxidation or hydrolysis.
  • a hydrocarbon chain generally a polyolefin chain
  • the hydrocarbyl-substituted carboxylic acid or acid derivative comprises a hydrocarbon chain, generally a polyolefin chain, to which is grafted a substance containing at least one ethylenic bond and at least one carboxylic acid or anhydride group, or a polar group which is convertible into a carboxylic group by oxidation or hydrolysis.
  • a hydrocarbon chain generally a polyolefin chain, to which is grafted a substance containing at least one ethylenic bond and at least one carboxylic acid or an
  • the dispersant product contains from 0.5 to 2, preferably 0.8 to 1.7, more preferably 1.0 to 1.5, for example, 1.05 to 1.2 acid groups, for example succinic groups, per mole of polyolefin starting material employed.
  • Preferred olefin polymers for reaction with the unsaturated carboxylic acids or derivatives thereof are those polymers derived from a major molar amount of C2 to C10, e.g., C2 to C5, monoolefin.
  • Such olefins include, for example, ethylene, propylene, butylene, isobutylene, pentene, octene-1, and styrene.
  • the polymers may be homopolymers, for example, polyisobutylene or copolymers of two or more of such olefins. These include copolymers of: ethylene and propylene; butylene and isobutylene: and propylene and isobutylene.
  • copolymers include those in which a minor molar amount of the copolymer monomers, for example, 1 to 10 mole percent, is a C4 to C18 diolefin, for example, a copolymer of isobutylene and butadiene or a copolymer of ethylene, propylene and 1,4-hexadiene.
  • the olefin polymer may be completely saturated, for example an ethylene-propylene copolymer made by a Ziegler-Natta synthesis using hydrogen as a moderator to control molecular weight.
  • An especially suitable starting material for a dispersant additive is polyisobutylene.
  • the olefin polymers will usually have number average molecular weights above about 700, preferably above about 900, including number average molecular weights within the range of from 1,500 to 5,000 with approximately one double bond per polymer chain.
  • the number average molecular weight for such polymers can be determined by any suitable technique. A convenient method for such determination is by gel permeation chromatography (GPC) which additionally provides molecular weight distribution information (see W. W. Yua, J. J. Kirkland and D. D. Bly, "Modern Size Exclusion Liquid Chromatography,” John Wiley and Sons, New York, 1979).
  • any suitable process may be used for reacting the olefin polymer with the unsaturated carboxylic acid or derivative thereof; a number of such processes are known in the art.
  • the olefin polymer and the carboxylic acid or acid derivative may simply be heated together as disclosed in U.S. Specifications Nos. 3 361 673 and 3 401 118 to cause a thermal "ene" reaction to take place.
  • the olefin polymer can first be halogenated, for example, chlorinated or brominated, for example to about 1 to 8, preferably 3 to 7, weight percent chlorine or bromine, based on the weight of polymer, by passing the chlorine or bromine through the polyolefin at a temperature of 100° to 250°C, for example 120° to 160°C, for about 0.5 to 10, preferably 1 to 7, hours.
  • the halogenated polymer may then be reacted with sufficient unsaturated acid or acid derivative at 100° to 250°, for example 180° to 220°C, for from 0.5 to 10, for example, 3 to 8 hours. Processes of this general type are taught, for example, in U.S. Specifications Nos.
  • Useful amine compounds for reaction with the hydrocarbyl substituted carboxylic acid or derivative thereof include mono- and polyamines having from 2 to 60, for example, 3 to 20, carbon atoms and from 1 to 12, for example 2 to 8, nitrogen atoms in a molecule.
  • These amines may be hydrocarbyl amines, which may include other groups such, for example, as hydroxy groups, alkoxy groups, amide groups, nitrile groups and imidazoline groups. Hydroxy amines with 1 to 6 hydroxy groups, preferably 1 to 3 hydroxy groups, are particularly useful.
  • Preferred amines are aliphatic saturated amines, including those of the general formulae: wherein R, R' and R'' are independently selected from the group consisting of hydrogen, C1 to C25 alkyl radicals, C1 to C12 alkoxy radicals, C2 to C6 alkylene radicals, C2 to C12 alkylamino radicals, and C2 to C6 alkylene radicals; s and s' can be the same or different and each is a number of from 2 to 6, preferably 2 to 4; and t is a number of from 0 to 10, preferably 2 to 7. At least one of R, R' or R'' must be a hydrogen atom.
  • Non-limiting examples of suitable amine compounds include: 1,2-diaminoethane; 1,3-diaminopropane: 1,4-diaminobutane; 1,6-diaminohexane; poly(ethyleneamines) such, for example, as diethylene triamine, triethylene tetramine and tetraethylene pentamine; poly(propylene amines) such, for example, as 1,2-propylene diamine, di-(1,2-propylene) triamine, and di-(1,3-propylene)triamine; N,N-dimethyl-1,3-diaminopropane; N,N-di-(2-aminoethyl) ethylene diamine; N,N-di-(2-hydroxyethyl)-1,3-propylene diamine; 3-dodecyloxypropylamine; N-dodecyl-1,3-propane diamine; tris hydroxymethylaminomethane (THAM);
  • amine compounds include: alicyclic diamines such, for example, as 1,4-di-(aminomethyl) cyclohexane, and heterocyclic nitrogen compounds such, for example, as imidazolines, and N-aminoalkyl piperazines of the general formula: wherein p1 and p2 are the same or different and each is an integer of from 1 to 4, and n1, n2 and n3 are the same or different and each is an integer of from 1 to 3.
  • Non-limiting examples of such amines include 2-pentadecyl imidazoline and N-(2-aminoethyl) piperazine.
  • alkylene amines Commercial mixtures of amine compounds may advantageously be used.
  • one process for preparing alkylene amines involves the reaction of an alkylene dihalide (such, for example, as ethylene dichloride or propylene dichloride) with ammonia, which results in a complex mixture of alkylene amines wherein pairs of nitrogen atoms are joined by alkylene groups, forming such compounds as diethylene triamine, triethylene tetramine, tetraethylene pentamine and corresponding piperazines.
  • Low cost poly(ethyleneamine) compounds averaging about 5 to 7 nitrogen atoms per molecule are available commercially under trade names such, for example, as "Polyamine H,” "Polyamine 400” and "Dow Polyamine E-100".
  • Mixtures of alkylene amines are described in, for example, the Encyclopedia of Chemical Technology (Kirk Othmer), Interscience Publishers, New York, (1950), Volume 5, pages 898 to 905, under the headline "Ethylene Amines”.
  • Useful amines also include polyoxyalkylene polyamines such, for example, as those of the formulae: where m has a value of from 3 to 70 and preferably 10 to 35; and where n has a value of about 1 to 40 with the proviso that the sum of all the n's is from 3 to 70 and preferably from 6 to 35, and R is a saturated hydrocarbon radical of up to ten carbon atoms, wherein the number of substituents on the R group is from 3 to 6.
  • the alkylene groups in formula (i) and formula (ii) may be straight or branched chains containing about 2 to 7, and preferably about 2 to 4, carbon atoms.
  • the polyoxyalkylene polyamines above which are preferably polyoxyalkylene diamines and polyoxyalkylene triamines, may have average molecular weights ranging from 200 to 4,000 and preferably from 400 to 2,000.
  • the preferred polyoxyalkylene polyamines include the polyoxyethylene and polyoxypropylene diamines and the polyoxypropylene triamines having average molecular weights ranging from 200 to 2,000.
  • the polyoxyalkylene polyamines are commercially available and may be obtained, for example, from the Jefferson Chemical Company, Inc. under the trade names "Jeffamines D-230, D-400, D-1000, D-2000, T-403," etc.
  • the amine may be reacted with the carboxylic acid or derivative thereof, for example, alkenyl succinic anhydride, by any suitable method.
  • an oil solution containing 5 to 95 weight percent of the carboxylic acid material may be heated to from 100 to 250°C, preferably 125 to 175°C, generally for 1 to 10, e.g., 2 to 6 hours, until the desired amount of water is removed.
  • the heating is preferably carried out to favour formation of imides or mixtures of imides and amides, rather than amides and salts. Reaction ratios can vary considerably, depending upon, for example, the reactants, amounts of excess amine, and type of bonds formed.
  • the nitrogen-containing dispersant can if desired be further treated by boration as generally taught in U.S. Specifications Nos. 3 087 936 and 3 254 025.
  • Tris (hydroxymethyl) amino methane can be reacted with the aforesaid acid material to form amides, imides or ester type additives as taught by British Specification No. 984 409, or to form oxazoline compounds and borated oxazoline compounds as described, for example, in U.S. Specifications Nos. 4 102 798, 4 116 876 and 4 113 639.
  • the dispersant may also be derived from an amino-alcohol including, for example, the amino-alkylene-, and amino-arylene-substituted alcohols having one or more amino-alkylene or amino-arylene or amino-arylene oxy-arylene radicals. They may be exemplified by N,N,N',N'-tetrahydroxy-tri-methylene diamine.
  • Mannich base type dispersants such, for example, as those described in U.S. Specifications Nos. 3 649 229 and 3 798 165 may also be used.
  • Such Mannich base dispersants can, for example, be formed by reacting a high molecular weight hydrocarbyl-substituted mono- or polyhydroxy benzene (for example, having a number average molecular weight of 1,000 or greater) with an amine (for example, a polyalkyl polyamine, a polyalkenyl polyamine, an aromatic amine, or a carboxylic acid-substituted polyamine or the succinimide formed from any one of these with an olefinic succinic acid or anhydride) and a carbonyl compound (e.g., formaldehyde or para formaldehyde).
  • a high molecular weight hydrocarbyl-substituted mono- or polyhydroxy benzene for example, having a number average molecular weight of 1,000 or greater
  • an amine
  • a very suitable dispersant for use in lubricating oil compositions is one derived from polyisobutylene substituted with succinic anhydride groups and reacted with a polyethylene amine, for example, tetraethylene pentamine, pentaethylene hexamine, polyoxyethylene or polyoxypropylene amine, for example, polyoxypropylene diamine, trismethylolaminomethane or pentaerythritol, and combinations thereof.
  • a polyethylene amine for example, tetraethylene pentamine, pentaethylene hexamine, polyoxyethylene or polyoxypropylene amine, for example, polyoxypropylene diamine, trismethylolaminomethane or pentaerythritol, and combinations thereof.
  • One preferred dispersant combination involves a combination of (A) polyisobutene substituted with succinic anhydride groups and reacted with (B) a hydroxy compound, e.g., pentaerythritol, (C) a polyoxyalkylene polyamine, e.g., polyoxypropylene diamine, and (D) a polyalkylene polyamine, e.g., polyethylene diamine and tetraethylene pentamine using from 0.3 to 2 moles each of (B) and (D) and from 0.3 to 2 moles of (C) per mole of (A) as described in U.S. Specification No. 3 804 763.
  • A polyisobutene substituted with succinic anhydride groups and reacted with (B) a hydroxy compound, e.g., pentaerythritol
  • C a polyoxyalkylene polyamine
  • polyoxypropylene diamine e.g., polyoxypropylene diamine
  • Another preferred dispersant combination involves the combination of (A) polyisobutenyl succinic anhydride with (B) a polyalkylene polyamine, for example, tetraethylene pentamine, and (C) a polyhydric alcohol or polyhydroxy-substituted aliphatic primary amine, for example, pentaerythritol or trismethylolaminomethane, as described in U.S. Specification No. 3 632 511.
  • Viscosity index improvers impart high and low temperature operability to a lubricating oil and permit it to remain shear stable at elevated temperatures and also exhibit acceptable viscosity or fluidity at low temperatures.
  • Viscosity index improver dispersants function as dispersants as well as viscosity index improvers.
  • examples of such viscosity index improver dispersants are compounds essentially similar to the dispersants described in detail above (that is, the reaction products of amines with a hydrocarbyl-substituted mono-or dicarboxylic acid or a derivative thereof) in which the hydrocarbyl substituent comprises a chain of sufficient length to impart viscosity index-improving properties to the compounds.
  • Such compounds can be prepared in a manner generally similar to that described above in connection with the corresponding dispersants.
  • the optimum amount of dispersant will depend on the use for which the oil is intended, which will influence the precise nature and proportions of the other constituents in the oil.
  • the proportion of dispersant will typically be in the range of from 0.1 to 10 mass %, especially 0.2 to 5 mass %, calculated on an active ingredient basis.
  • the person skilled in the art will readily be able to determine, by routine experiment, the proportion of dispersant most appropriate to a particular use. In one particular oil suitable for use as a TPEO, the most appropriate amount of dispersant was found to be in the range of from 0.25 to 2 mass %, calculated on an active ingredient basis.
  • lubricating oils for marine use advantageously include at least one metal-containing detergent additive and at least one ZDDP.
  • Overbased metal-containing detergent additives for use in accordance with the invention include, for example, overbased phenates, sulphurized phenates, sulphonates, salicylates and naphthenates of the alkali metals, alkaline earth metals and magnesium.
  • Highly basic metal sulphonates may be produced, for example, by heating a mixture comprising an oil-soluble alkaryl sulphonic acid or sulphonate, with an excess of alkali metal or alkaline earth metal compound or magnesium above that required for complete neutralization of any sulphonic acid present and forming a dispersed carbonate complex by reacting the excess metal with carbon dioxide to provide the desired overbasing.
  • the sulphonic acids are typically obtained by the sulphonation of alkyl-substituted aromatic hydrocarbons such, for example, as those obtained from the fractionation of petroleum by distillation and/or extraction or by the alkylation of aromatic hydrocarbons as for example those obtained by alkylating benzene, toluene, xylene, naphthalene, diphenyl and halogen derivatives thereof, for example, chlorobenzene, chlorotoluene and chloronaphthalene.
  • the alkylation may be carried out, in the presence of a catalyst, with an alkylating agent having from about 3 to more than 30 carbon atoms.
  • haloparaffins for example, haloparaffins, olefins obtained by dehydrogenation of paraffins, and polyolefin polymers produced from ethylene and/or propylene are all suitable.
  • the alkaryl sulphonates usually contain from 9 to 70 or more carbon atoms, preferably from 16 to 50 carbon atoms, per alkyl-substituted aromatic moiety.
  • Compounds which may be used in neutralizing these alkaryl sulphonic acids to provide the sulphonates include the oxides and hydroxides, alkoxides, carbonates, carboxylates, sulphides, hydrosulphides, nitrates, borates and ethers of sodium, magnesium, calcium, strontium and barium.
  • suitable compounds are calcium oxide, calcium hydroxide, magnesium oxide, magnesium acetate and magnesium borate.
  • the metal compound is used in excess of that required for complete neutralization of the alkaryl sulphonic acids. Generally, the amount ranges from 100 to 220 percent, although it is preferred to use at least 125 percent, of the stoichiometric amount of metal required for complete neutralization.
  • the individual R groups may each contain from 5 to 40, but as indicated above preferably contain from 9 to 12, carbon atoms.
  • the sulphurized alkyl phenols which are useful generally contain from 2 to 14% by weight, preferably 4 to 12 wt. % sulphur based on the weight of sulphurized alkyl phenol.
  • the sulphurized alkyl phenol may be converted to a salt by reaction with a metal-containing material, for example, a metal oxide, hydroxide or complex, in an amount sufficient to neutralize the phenol and, if desired, to overbase the product to a desired basicity.
  • a metal-containing material for example, a metal oxide, hydroxide or complex
  • a preferred process involves neutralization using a solution of metal in a glycol ether.
  • the neutral or normal sulphurized metal phenates are those in which the ratio of metal to phenol nucleus is substantially stoichiometric.
  • the "overbased" or “basic” sulphurized metal phenates are sulphurized metal phenates wherein the ratio of metal to phenol is greater than that required by stoichiometry, e.g. basic sulphurized metal dodecyl phenate has a metal content up to and greater than 100% in excess of the metal present in the corresponding normal sulphurized metal phenates, the excess metal being present in oil-soluble or dispersible form (for example, by reaction with CO2).
  • overbased materials may be used as the sole metal detergent additive or in combination with the same additives in the neutral form.
  • the ZDDPs used as anti-wear agents, and also to provide antioxidant activity may be prepared, for example, in accordance with known techniques by first forming a dithiophosphoric acid, usually by reaction of an alcohol or a phenol with P2S5, and then neutralizing the dithiophosphoric acid with a suitable zinc compound.
  • Alcohols may be used, including mixtures of primary and secondary alcohols, secondary alcohols generally imparting improved anti-wear properties, and primary alcohols giving improved thermal stability properties. Mixtures of the two are particularly useful.
  • any basic or neutral zinc compound could be used but the oxides, hydroxides and carbonates are most generally employed.
  • Commercial additives frequently contain an excess of zinc because of the use of an excess of the basic zinc compound in the neutralization reaction.
  • the preferred zinc dihydrocarbyl dithiophosphates for use in the present invention are oil soluble salts of dialkyl esters of dithiophosphoric acids represented by the formula: [RO(R'O)PS2]2Zn wherein R and R' may be the same or different alkyl radicals preferably containing 3 to 10, more preferably 3 to 8 carbon atoms and including n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, amyl, n-hexyl, i-hexyl, n-octyl, 2-ethylhexyl, cyclohexyl and methylcyclopentyl groups.
  • R and R' may be the same or different alkyl radicals preferably containing 3 to 10, more preferably 3 to 8 carbon atoms and including n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl,
  • additives which may be used in formulating TPEOs are, for example, antioxidants, for example, alkylated diphenylamines, and rust inhibitors, for example, alkyl thiadiazoles.
  • lubricating oil base stocks may be used in accordance with the invention, for example for preparing a lubricating composition or a concentrate in accordance with the invention.
  • suitable base stocks include natural base oils and synthetic base oils such, for example, as alkyl esters of dicarboxylic acids, polyglycols and alcohols; polyalpha-olefins, polybutenes, alkyl benzenes, organic esters of phosphoric acids, and polysilicone oils.
  • Natural base oils include mineral lubricating oils which may vary widely as to their crude source, for example, as to whether they are paraffinic, naphthenic, mixed, or paraffinic-naphthenic, as well as to the details of their production, for example, distillation range, straight run or cracked, hydrofined, solvent extracted and the like.
  • natural lubricating oil base stocks which can be used in accordance with the invention may be straight mineral lubricating oil or distillates derived from paraffinic, naphthenic, asphaltic, or mixed base crude oils.
  • various blended oils may be employed as well as residual oils, particularly those from which asphaltic constituents have been removed.
  • the oils may be refined by any suitable method, for example, using acid, alkali, and/or clay or other agents such, for example, as aluminium chloride, or they may be extracted oils produced, for example, by solvent extraction with solvents, for example, phenol, sulphur dioxide, furfural, dichlorodiethyl ether, nitrobenzene, or crotonaldehyde.
  • Lubricating oil base stocks suitable for use in preparing TPEOs conveniently have a viscosity of typically about 3 to about 15 cSt (about 3 x 10 ⁇ 6 to about 15 x 10 ⁇ 6 m2/s) at 100°C, although base stocks with other viscosities may also be used.
  • base stocks with other viscosities may also be used.
  • bright stocks which typically has a viscosity of about 30 cSt. (about 30 x 10 ⁇ 6 m2/s) at 100°C may be used in some applications.
  • the additives used in accordance with the invention are oil-soluble, dissolvable in oil with the aid of a suitable solvent, or are stably dispersible materials.
  • Oil-soluble, dissolvable, or stably dispersible does not necessarily indicate that the materials are soluble, dissolvable, miscible, or capable of being suspended in oil in all proportions. It does mean, however, that the additives are, for instance, soluble or stably dispersible in oil to an extent sufficient to exert their intended effect in the environment in which the oil is employed.
  • the additional incorporation of other additives may also permit incorporation of higher levels of a particular additive, if desired.
  • Additives used in accordance with the present invention can be incorporated into the lubricating oil in any convenient way. Thus, they can be added directly to the oil by dispersing, or by dissolving them in the oil at the desired level of concentration. Such blending may be effected at room temperature or an elevated temperature.
  • Additives used in accordance with the present invention may be employed in a lubricating oil composition which comprises lubricating oil, typically in a major amount, and the additives, typically in a minor amount. Additional additives, for example, the additional additives indicated above, may be incorporated in the composition to enable it to meet particular requirements.
  • Typical proportions for additional additives for a TPEO in accordance with the invention are as follows: Additive Mass % active ingredient Detergent(s) 1 to 10 ZDDP(s) 0.1 to 1.5 Antioxidant(s) 0.2 to 2 Rust Inhibitor(s) 0.005 to 0.05
  • additive concentrates comprising the additives (the concentrate sometimes being referred to herein as an additive package) whereby several additives can be added simultaneously to the base oil to form the lubricating oil composition. Dissolution of the additive concentrate into the lubricating oil may be facilitated by solvents and by mixing accompanied with mild heating, but this is not essential.
  • the concentrate or additive package will typically be formulated to contain the additive(s) in proper amounts to provide the desired concentration in the final formulation when the additive package is combined with a predetermined amount of base lubricant.
  • one or more additives can be added to small amounts of base oil or other compatible solvents along with other desirable additives to form additive packages containing active ingredients in an amount of, for example, from about 20 to about 70 mass %, and preferably from about 40 to about 65 mass %, additives in the appropriate proportions with the remainder being base oil.
  • the final formulations may employ typically about 4 to 20 mass % of the additive package with the remainder being base oil.
  • An ashless dispersant comprising a borated reaction product of a polyisobutenyl succinic anhydride with a polyamine was introduced into a reaction vessel, followed in turn by tetrapropenyl succinic anhydride (TPSA) (if used) and an overbased calcium sulphonate detergent.
  • TPSA tetrapropenyl succinic anhydride
  • the contents of the vessel were mixed at 80°C for 1 hour, then cooled to 60°C, following which there were added a demulsifier (where indicated in Table 1), an antioxidant, a rust inhibitor, and base oil.
  • the mixture was stirred for 1 hour at 60°C, and a zinc dihydrocarbyl dithiophosphate was then added.
  • Table 1 The proportions of the components indicated above are shown in Table 1.
  • the proportions of each of the dispersant, detergent, antioxidant, rust inhibitor and demulsifier were the same in each of the examples.
  • the demulsifier used in these examples was a blend (92 mass % active ingredient in diluent oil) of a propoxylated dipropylene glycol crosslinked with the diglycidylether of bisphenol A, and two different constituents prepared by reacting with propylene oxide, or ethylene oxide and propylene oxide, a propoxylated dipropylene glycol crosslinked with the diglycidyl ether of bisphenol A.
  • compositions suitable for use in Test Method ASTM D1401 which measures the ability of petroleum oils or synthetic fluids to separate from water (commonly referred to as the ability of the oils or other fluids to "shed" water), were prepared by mixing about 18 parts by mass of the concentrate with about 82 parts by mass of base oil.
  • the final compositions had a TBN of 40.
  • a lubricating oil suitable for use as a TPEO was prepared by mixing an overbased calcium phenate detergent, the detergent used in Example 1, an ashless dispersant obtained by reacting a polyisobutenyl succinic anhydride with a polyamine, a ZDDP, a demulsifier and base oil.
  • the demulsifier used in Comparative Example 4 contained 15.7 % active ingredients and comprised a propoxylated triol crosslinked with adipic acid, an ethoxylated phenol formaldehyde resin esterified with a mixture of C16 to C18 fatty acids, and base solvents, while in the demulsifier used in Example 2, a proportion of the solvent mixture was replaced by TPSA to give a demulsifier/TPSA mixture containing about 75 mass % TPSA calculated on the demulsifier active ingredients.
  • the total proportion of demulsifier, or demulsifier and TPSA, in the final oil was 0.02 mass %, and the TBN of the final oil was 40 in each case.

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

Claims (18)

  1. Verwendung einer freien Dicarbonsäure oder eines freien Dicarbonsäureanhydrids zur Erhöhung der Wirksamkeit eines Demulgators für eine Wasser-in-Öl-Emulsion, die ein aschefreies Dispergiermitteladditiv enthält, wobei der Demulgator ein vernetztes Polyoxyalkylenpolyol umfaßt.
  2. Schmierstoffzusammensetzung, die ein Öl mit Schmierviskosität, ein aschefreies Dispergiermitteladditiv, einen Demulgator, der ein vernetztes Polyoxyalkylenpolyol umfaßt, und eine freie Dicarbonsäure oder ein freies Dicarbonsäureanhydrid umfaßt.
  3. Schmierstoffzusammensetzung nach Anspruch 2, bei der die Dicarbonsäure oder die Dicarbonsäure, aus der das Anhydrid abgeleitet ist, die allgemeine Formel



            HO₂C-(R)-CO₂H



    hat, in der R eine zweiwertlge Kohlenwasserstoffgruppe bedeutet.
  4. Schmierstoffzusammensetzung nach Anspruch 3, bei der in der in Anspruch 3 angegebenen Formel R einen geradkettigen oder verzweigten, gesättigten oder ungesättigten, zweiwertigen aliphatischen Rest bedeutet.
  5. Schmierstoffzusammensetzung nach einem der Ansprüche 2 bis 4, bei der die Dicarbonsäure oder das Dicarbonsäureanhydrid eine Alk(en)ylbernsteinsäure oder ein Alk(en)ylbernsteinsäureanhydrid ist.
  6. Schmierstoffzusammensetzung nach einem der Ansprüche 2 bis 4, bei der das Dicarbonsäureanhydrid Tetrapropenylbernsteinsäureanhydrid ist.
  7. Schmierstoffzusammensetzung nach einem der Ansprüche 2 bis 6, bei der das vernetzte Polyoxyalkylenpolyol durch Vernetzen des Reaktionsprodukts aus einem Polyol und einem Alkylenoxid oder einer Verbindung, die von einem Alkylenoxid abgeleitete Gruppen enthält, hergestellt ist.
  8. Schmierstoffzusanmensetzung nach Anspruch 7, bei der das vernetzte Polyoxyalkylenpolyol durch Vernetzen des Reaktionsprodukts aus einem Alkylenglykol oder einem Alkylentriol und einem Alkylenoxid oder einer Verbindung, die von einem Alkylenoxid abgeleitete Gruppen enthält, hergestellt ist.
  9. Schmierstoffzusammensetzung nach Anspruch 7 oder Anspruch 8, bei der das Alkylenoxid Ethylenoxid und/oder Propylenoxid ist.
  10. Schmierstoffzusammensetzung nach einem der Ansprüche 7 bis 9, bei der das Vernetzen unter Verwendung einer Dicarbonsäure oder eines Diglycidylethers einer aliphatischen oder aromatischen Hydroxyverbindung bewirkt wird.
  11. Schmierstoffzusammensetzung nach einem der Ansprüche 2 bis 10, bei der der Demulgator außerdem einen oder mehrere zusätzliche Bestandteile umfaßt, welche Oxyalkylengruppen enthalten.
  12. Schmierstoffzusammensetzung nach einem der Ansprüche 2 bis 11, bei der das aschefreie Dispergiermitteladditiv ein aschefreies Dispergiermitteladditiv ausgewählt aus
    (i) den Reaktionsprodukten aus einem Amin und einer mit langkettigem Kohlenwasserstoff substituierten Mono- oder Dicarbonsäure oder einem Derivat davon,
    (ii) langkettigen Kohlenwasserstoffen mit einem oder mehreren direkt daran gebundenen Polyaminmolekülen, und
    (iii) Mannichkondensationsprodukten, die eine langkettige Kohlenwasserstoffgruppe enthalten,
    wobei die langkettige Kohlenwasserstoffgruppe in (i), (ii) und (iii) ein Polymer aus einem C₂- bis C₁₀-Monoolefin ist und ein durchschnittliches Molekulargewicht (Zahlenmittel) von mindestens etwa 900 aufweist.
  13. Schmierstoffzusammensetzung nach einem der Ansprüche 2 bis 12, bei der das aschefreie Dispergiermitteladditiv das Reaktionsprodukt aus einem Polyamin und einer kohlenwasserstoffsubstituierten Bernsteinsäure oder einem kohlenwasserstoffsubstituierten Bernsteinsäureanhydrid umfaßt.
  14. Schmierstoffzusammensetzung nach Anspruch 13, bei der das Reaktionsprodukt boriert ist.
  15. Schmierstoffzusammensetzung nach einem der Ansprüche 2 bis 4, bei der die Zusammensetzung außerdem mindestens ein metallhaltiges Detergensadditiv und/oder mindestens ein Zinkdikohlenwasserstoffdithiophosphat enthält.
  16. Schmierstoffzusammensetzung nach einem der Ansprüche 2 bis 15, die eine TBN (Gesamtbasenzahl) im Bereich von 9 bis 40 aufweist.
  17. Verfahren zur Herstellung einer Schmierstoffzusammensetzung, bei dem in beliebiger Reihenfolge ein Öl mit Schmierviskosität, ein aschefreies Dispergiermitteladditiv, ein Demulgator und eine freie Dicarbonsäure oder ein freies Dicarbonsäureanhydrid gemischt werden.
  18. Als Additiv für Schmieröl brauchbares Konzentrat, das ein aschefreies Dispergiermitteladditiv, einen Demulgator, der ein vernetztes Polyoxyalkylenpolyol umfaßt, eine freie Dicarbonsäure oder ein freies Dicarbonsäureanhydrid, ein überbasisches Metalldetergens, ein ZDDP und Basisöl umfaßt.
EP92903475A 1991-01-31 1992-01-31 Emulsionsspaltung von ölen Expired - Lifetime EP0523213B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9102097 1991-01-31
GB919102097A GB9102097D0 (en) 1991-01-31 1991-01-31 Demulsification of oils
PCT/EP1992/000242 WO1992013933A1 (en) 1991-01-31 1992-01-31 Demulsification of oils

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EP0523213A1 EP0523213A1 (de) 1993-01-20
EP0523213B1 true EP0523213B1 (de) 1995-02-22

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FI (1) FI924378A0 (de)
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GB9413005D0 (en) * 1994-06-28 1994-08-17 Exxon Research Engineering Co Luybricating oil compositions or concentrates therefor providing enhanced water-shedding properties
GB9503994D0 (en) * 1995-02-28 1995-04-19 Bp Chem Int Ltd Lubricating oil compositons
JP2010500453A (ja) * 2006-08-07 2010-01-07 ザ ルブリゾル コーポレイション 内燃機関を潤滑する方法
US7951758B2 (en) 2007-06-22 2011-05-31 Baker Hughes Incorporated Method of increasing hydrolytic stability of magnesium overbased products
US20090203559A1 (en) * 2008-02-08 2009-08-13 Bera Tushar Kanti Engine Lubrication
US20090253597A1 (en) * 2008-03-31 2009-10-08 Exxonmobil Research And Engineering Company Lubricant composition with improved varnish deposit resistance
US9228147B2 (en) 2010-12-14 2016-01-05 Exxonmobil Research And Engineering Company Glycol ether-based cyclohexanoate esters, their synthesis and methods of use
US9771466B2 (en) 2010-12-14 2017-09-26 Exxonmobil Chemical Patents Inc. Glycol ether-based cyclohexanoate ester plasticizers and blends therefrom
RU2727600C1 (ru) * 2019-08-06 2020-07-22 Общество с ограниченной ответственностью "Газпромнефть Научно-Технический Центр" (ООО "Газпромнефть НТЦ") Способ разделения водонефтяной эмульсии с помощью электрогидравлического воздействия, устройство и система для его осуществления
CN116925303B (zh) * 2023-09-18 2023-12-01 山东久元新材料有限公司 一种炼油液体助剂及其生产工艺

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US9963642B2 (en) 2002-08-30 2018-05-08 Baker Petrolite LLC Additives to enhance metal and amine removal in refinery desalting processes

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JPH05505420A (ja) 1993-08-12
BR9204108A (pt) 1993-06-08
WO1992013933A1 (en) 1992-08-20
ES2068704T3 (es) 1995-04-16
GB9102097D0 (en) 1991-03-13
FI924378A0 (fi) 1992-09-29
EP0523213A1 (de) 1993-01-20

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