WO2004085580A1 - Melange d'additifs pour ameliorer les proprietes du pouvoir lubrifiant de produits mineraux - Google Patents

Melange d'additifs pour ameliorer les proprietes du pouvoir lubrifiant de produits mineraux Download PDF

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WO2004085580A1
WO2004085580A1 PCT/EP2004/003253 EP2004003253W WO2004085580A1 WO 2004085580 A1 WO2004085580 A1 WO 2004085580A1 EP 2004003253 W EP2004003253 W EP 2004003253W WO 2004085580 A1 WO2004085580 A1 WO 2004085580A1
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additive mixture
additive
mixture according
acid
fuel oil
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PCT/EP2004/003253
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German (de)
English (en)
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Siegbert Brand
Wolfgang Ahlers
Ansgar Eisenbeis
Peter Schwab
Irene Trötsch-Schaller
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Basf Aktiengesellschaft
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M161/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1885—Carboxylic acids; metal salts thereof resin acid
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1888—Carboxylic acids; metal salts thereof tall oil
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1966—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof poly-carboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
    • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C10M2207/126—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/18—Tall oil acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/20—Rosin acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/086—Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure

Definitions

  • the present invention relates to an additive mixture which contains at least one aliphatic monocarboxylic acid, at least one polycyclic carboxylic acid and at least one copolymer of lower olefins and unsaturated esters. Furthermore, the invention relates to the use of this additive mixture for the additivation of mineral oil products, also fuel oil and lubricant compositions and concentrates which contain this additive mixture.
  • lubrication improvers such as fatty acid mixtures, their esters, amides or salts
  • WO 98/04656 describes diesel fuels with a sulfur content of at most 500 pp, which contains an additive mixture of monocarboxylic acids and polycyclic acids to improve the lubricity.
  • this additive mixture is still not satisfactory.
  • EP 1 028 155 describes the use of copolymers of ethylene and unsaturated esters to improve the lubricity of conventional lubricity additives. However, the amounts of additive required to improve the lubricity sufficiently are unsatisfactorily high.
  • the object of the present invention was therefore to provide additive mixtures which effectively improve the lubricity of fuel oil and lubricant compositions, even at lower metering rates.
  • the present invention therefore relates to an additive mixture comprising
  • component B at least one polycyclic carboxylic acid
  • component C at least one copolymer of lower olefins and unsaturated esters.
  • alkyl denotes both branched and linear alkyl groups.
  • C 1 -C 4 alkyl denotes methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl.
  • Ci-Cs-alkyl also designates pentyl or neopentyl and other positional isomers.
  • Ci-Cs-alkyl also designates, for example, hexyl, heptyl, octyl and 2-ethylhexyl and other positional isomers.
  • C 1 -C 0 alkyl also denotes wonyl, decyl and their positional isomers.
  • C ⁇ -C ⁇ -alkyl also denotes ündecyl, dodecyl, tridecyl, Tetradecyl, pentadecyl, hexadecyl, heptadecyl and positional isomers of these residues.
  • alkenyl denotes linear or branched, mono- or polyunsaturated alkenyl residues.
  • C 2 -Cs-alkenyl represents vinyl, 1-propenyl, allyl, butenyl, isobutenyl, butadienyl, pentenyl or pentadienyl.
  • aryl denotes in particular optionally substituted phenyl, benzyl, tolyl or naphthyl.
  • Suitable substituents are, for example, -C 4 alkyl, OH and 0 -C -C 4 alkyl.
  • aliphatic monocarboxylic acid denotes both the monocarboxylic acid itself and its derivatives, which are selected from carboxylic acid esters, the reaction products of carboxylic acids with primary, secondary and tertiary amines and polyamines, the carboxylic acid ammonium salts, amides, Include imides and amidines, and nitriles. However, it is preferably the carboxylic acid itself.
  • polycyclic carboxylic acid denotes both the carboxylic acid itself and its derivatives, which are also selected for these acids from carboxylic acid esters, the reaction products of carboxylic acids with primary, secondary and tertiary amines and polyamines, the carboxylic acid ammonium salts, Amides, imides and amidines include, and nitriles. However, it is preferably the carboxylic acid itself.
  • the aliphatic monocarboxylic acid is preferably a saturated or unsaturated linear or branched monocarboxylic acid with 12 to 24 carbon atoms, particularly preferably with 16 to 20 carbon atoms and especially with 18 carbon atoms in the carboxylic acid part of the molecule.
  • the monocarboxylic acid is particularly preferably linear.
  • a mixture of saturated and unsaturated aliphatic monocarboxylic acids is preferably used as component A.
  • a mixture of at least one saturated, at least one monounsaturated and / or at least one polyunsaturated aliphatic monocarboxylic acid is particularly preferably used.
  • the saturated and unsaturated carboxylic acids each have the same chain length.
  • component A is a mixture of at least one saturated aliphatic monocarboxylic acid, at least one monounsaturated aliphatic monocarboxylic acid and at least one polyunsaturated aliphatic monocarboxylic acid.
  • at least 95%, especially at least 99%, of the carboxylic acids have the same chain length.
  • the molar mixing ratio of saturated carboxylic acids to monounsaturated carboxylic acids to polyunsaturated carboxylic acids is 1: 5-7: 4-6.
  • mixtures are also suitable in which the molar mixing ratio of saturated carboxylic acids to monounsaturated carboxylic acids to polyunsaturated carboxylic acids is 1: 5-55: 6-65 and preferably 1: 8-45: 15-35.
  • saturated aliphatic monocarboxylic acids examples include lauric acid, tridecanoic acid, myisic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, tuberculostearic acid, nonadecanoic acid, arachic acid, behenic acid and lignoceric acid.
  • Suitable unsaturated aliphatic monocarboxylic acids are palmitoleic acid, oleic acid and erucic acid (mono-unsaturated), linoleic acid (mono-unsaturated), linolenic acid and elaeostearic acid (tri-unsaturated), arachidonic acid (four-times unsaturated), clupanodonic acid (five-times unsaturated) and do- (six-times unsaturated) unsaturated). Palmitic acid or stearic acid is preferably used as the saturated aliphatic monocarboxylic acid.
  • the unsaturated monocarboxylic acids oleic acid, linoleic acid, linolenic acid and elaeostearic acid are preferred.
  • the polycyclic carboxylic acid is preferably a ring system which comprises at least two 5- or 6-membered, saturated or unsaturated cycles and is condensed via two adjacent carbon atoms, at least one cycle being selected by at least one carboxyl group or by at least one carboxyl derivative is substituted among carboxylic acid ester groups, the reaction products of carboxyl groups with primary, secondary and tertiary amines and polyamines, which include ammonium carboxylates, carboxamides, imides and amidines, and nitriles, and where each cycle optionally contains a heteroatom selected from 0 and N.
  • the polycyclic carboxylic acid has the general formula V.
  • X stands for a carbon atom or for a heteroatom which is selected from 0 and N, where in each cycle only one X may stand for a heteroatom and the bond between two ring atoms X can be either a single bond or a double bond ;
  • R 15 , R 16 , R 17 and R 18 independently of one another represent H, Ci-Cs-alkyl, C 2 -C 5 alkenyl or aryl, where R 15 and R 16 or R 17 and R 18 together with the ring atoms X to which they are attached can form a cycle which is saturated or unsaturated, contain a heteroatom which is selected from 0 and N, and by a saturated or unsaturated aliphatic hydrocarbon radical having one to four carbon atoms or by egg - A hydroxy residue can be substituted; and
  • Z stands for COOH, COOR 19 , CN or a carboxyl derivative which is formed in the reaction of carboxylic acid with amines.
  • R 19 stands for Ci-Cg-alkyl which is interrupted by one or more groups which are selected from 0 and NR 20 and / or by one or more groups which are selected from OR 21 and NR 22 R 23 can be, where R 20 , R 21 , R 22 and R 23 are defined as R 19 or are H, or R 19 is C 2 -C 5 -alkenyl.
  • Carboxyl derivatives which are formed in the reaction of carboxyl groups with amines are those mentioned above, ie ammonium carboxylates, carboxamides, imides and amidines. These are preferably ammonium carboxylates or carboxamides. These ammonium salts or amides are particularly preferably derived from amines which are selected from 2-ethylhexylamine, N, N-dibutylamine, ethylenediamine, diethylenetriamine, triethylene tetramine and tetraethylene pentamine.
  • R 15 and R 16 or R 17 and R 18 form a ring together with the ring atoms X to which they are attached, it is preferably a 5- or 6-ring, particularly preferably a carbocyclic 5 - Or 6-ring and especially see a carbocyclic 6-ring.
  • the ring can be saturated or single, double or triple unsaturated.
  • the ring is preferably by at least one Cx-C ⁇ alkyl group, in particular by methyl or isopropyl, by a C 2 -C 5 alkenyl group, in particular by vinyl, by an optionally substituted exocyclic double bond, in particular by a dimethyl substituted exocyclic double bond and / or substituted by a hydroxy group.
  • R 15 and R 16 are preferably H or methyl. Both R 15 and R 16 are particularly preferably methyl. R 15 is more preferably bound to a bridging carbon atom. In particular, R 16 and Z are bonded to the same atom X, where X represents a carbon atom.
  • R 17 and R 18 preferably form a 5 or 6 ring with the atoms X to which they are attached, particularly preferably a carbocyclic 5 or 6 ring and in particular a carbocyclic 6 ring, ie the atoms X to which they are attached are carbon atoms.
  • the ring can be saturated or single, double or triple unsaturated.
  • the ring is preferably through at least one C 1 -C 4 -alkyl group, in particular through methyl or isopropyl, through a C 2 -C 5 -alkenyl group, in particular through vinyl, through an optionally substituted exocyclic double bond, in particular through a dimethyl-substituted exocyclic double bond and / or substituted by a hydroxy group.
  • the radical R 19 is Ci-Cg-alkyl which is interrupted by one or more groups selected from 0 and NR 20 and optionally substituted by one or more groups selected from OR 21 and NR 22 R 23 , preferably for a radical of the formula
  • a for a C 2 -C 4 alkylene radical in particular for ethylene, 1,2- or 1,3-propylene, 1,2-, 2,3-, 3,4-, 1,3- or 1,4- Butylene stands,
  • X represents 0 or NR 20 , wherein R 20 is H or C 1 -C 4 alkyl,
  • Y represents H, OR 21 or NR 2 R 23 ,
  • R 21 is defined as R 20 and R 22 and R 23 for H
  • n stands for a number from 1 to 3.
  • Ci-Cg-alkyl which is substituted by one or more groups selected from OR 21 and NR 22 R 23 , is preferably C 2 -Cg-alkyl, which is substituted by one to three hydroxyl groups and / or is substituted by one to three radicals NR 22 R 23 .
  • the ester group COOR 19 is preferably derived from an alcohol R 19 OH, which is selected from primary alcohols having 1 to 8 carbon atoms, such as methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, isobutanol, tert-butanol, pentanol , Allyl alcohol, further polyols with 2 to 8 carbon atoms and 2 to 5 OH groups, such as ethylene glycol, propylene glycol, glycerol, trimethylolpropane and pentaerythritol, and primary, secondary and tertiary amino alcohols with 2 to 9 carbon atoms and 1 to 3 OH- Groups such as diethanolamine and triethanolamine.
  • R 19 OH is selected from primary alcohols having 1 to 8 carbon atoms, such as methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol
  • Z is preferably COOH.
  • X preferably represents a carbon atom.
  • polycyclic carboxylic acid has the general formula VI
  • the polycyclic carboxylic acid or the corresponding derivative is preferably an acid of the formula V.
  • the polycyclic carboxylic acid or the corresponding derivative of the formula V is particularly preferably a resin acid or a resin acid derivative.
  • Preferred resin acid or its derivatives are abietic acid, dihydroabietic acid, tetrahydroabietic acid, dehydroabietic acid, neoabietic acid, pimaric acid, laevopimaric acid, palustric acid, paraastric acid or derivatives of these acids.
  • Resin acids are usually obtained by distillation of natural resins obtained from trees containing resin, in particular from conifers.
  • the copolymer preferably contains structural units of the formulas I and II
  • R 1 'R 2 and R 3 independently of one another are H, methyl or ethyl, R 4 represents H, -CC 4 alkyl or COOR 7 ,
  • R 5 represents H or methyl
  • R 6 stands for COOR 7 or OOCR 8 ,
  • R 7 represents a linear or branched C 1 -C 4 -alkyl radical
  • R 8 represents H or R 7 ,
  • R 9 , R 10 and R 11 are independently defined as R 1 , R 2 and R 3 ,
  • R 12 is defined as R 4 ,
  • R 13 is defined as R 5 and R 14 is defined as R 6 ,
  • the structural units I and III and the structural units II and IV are each different from one another.
  • R 1 , R 2 and R 3 are preferably H; that is, the structural units I preferably correspond to copolymerized ethylene.
  • R 7 preferably represents a linear C 1 -C 4 -alkyl radical, particularly preferably a linear C 1 -C 4 -alkyl radical, such as methyl, ethyl, n-propyl or n-butyl, and especially methyl.
  • R 7 is preferably a branched C 3 -C ⁇ alkyl, more preferably a branched C 3 -C ⁇ o _A lkylrest. In particular, there is at least one branch on a carbon atom that is ⁇ or ⁇ to the carboxyl group.
  • radicals are isopropyl, isobutyl, tert-butyl, neopentyl, neohexyl, neoheptyl, neooctyl, neononyl and neodecyl.
  • R 6 preferably represents OOCR 8 .
  • R 8 preferably represents a linear C 1 -C 4 -alkyl radical, particularly preferably a C 1 -C 1 -alkyl radical.
  • R 8 is preferably a branched C 3 -C ⁇ alkyl radical, particularly preferably a branched C 3 -C ⁇ 0 alkyl radical.
  • Preferred branched C 3 -C ⁇ o alkyl are isopropyl, isobutyl, tert-butyl, neopentyl, neohexyl, Neoheptyl, Neooctyl, Neononyl and neodecyl and particularly Neooctyl, Neononyl and neodecyl.
  • R 8 in the structural units of the formula II is particularly preferably a linear C 1 -C 10 -alkyl radical, in particular methyl, ethyl, pentyl or heptyl and especially methyl.
  • R 4 preferably represents H or methyl, particularly preferably H.
  • R 5 preferably represents H.
  • the repeating unit of the formula II particularly preferably stands for polymerized vinyl acetate, vinyl propionate, vinyl hexanoate or vinyl octanoate and in particular for vinyl acetate.
  • R 9 and R 10 both represent H and R 11 represents methyl or ethyl, ie the repeating units III correspond to polymerized propylene or n-butylene;
  • R 9 and R 10 are both methyl and R 11 is H; ie the repeating units III correspond to polymerized 2-butylene;
  • R 9 is H and R 10 and R 11 are both methyl; ie repeating units III correspond to polymerized isobutylene.
  • R 14 preferably represents OOCR 8 .
  • R 8 preferably represents a branched C 3 -C 7 -alkyl radical, particularly preferably a branched C 3 -C-alkyl radical. In particular, there is at least one branch on a carbon atom which is ⁇ or ⁇ to the carboxyl group.
  • Preferred branched C 1 -C 10 -alkyl radicals are isopropyl, isobutyl, tert-butyl, neopentyl, neohexyl, neoheptyl, neooctyl, neo- nonyl and neodecyl and especially neooctyl, neononyl and neodecyl.
  • R 12 preferably represents H or methyl, particularly preferably H.
  • R 13 preferably represents H.
  • the repeating unit IV particularly preferably stands for polymerized vinyl neononanoate or vinyl neodecanoate.
  • the copolymer of component C contains the structural units of the formula I in an amount of preferably 65 to 99 mol%.
  • the structural units of the formula II are preferably present in an amount of 1 to 35 mol%, particularly preferably 1 to 30 mol% and in particular 1 to 25 mol%, based on the total copolymer.
  • the structural units of the formula III are preferably present in the copolymer in an amount of 0 to 20 mol%, particularly preferably 0 to 10 mol% and in particular 0 to 5 mol%, based on the total copolymer.
  • the structural units of the formula IV are preferably present in the copolymer in an amount of 0 to 20 mol%, particularly preferably 0 to 10 mol% and in particular 0 to 5 mol%, based on the total copolymer.
  • the copolymer of component C preferably has a number average molecular weight M n of 1000 to 10000, particularly preferably from 1000 to 5000.
  • Component C can also contain several of the copolymers described above, in which case these must be different. The difference can exist both in the type of polymerized monomers and in the amount in which the same monomers are polymerized in, or in the molecular weight of the copolymers.
  • the copolymer of component C contains essentially no, ie at most 1% by weight, particularly preferably at most 0.5% by weight, based on the total weight of the copolymer, of copolymerized repeating units of the formulas III and IV.
  • a copolymer of ethylene and vinyl acetate is particularly preferably used as component C.
  • Ethylene is present in the copolymer in an amount of preferably 65 to 96 mol%, particularly preferably 75 to 94 mol%, based on the total copolymer.
  • the residual content of the copolymer consists of vinyl acetate repeating units.
  • the copolymers of component C can be obtained, for example, by direct copolymerization of the monomers, it being possible for the ester group of the copolymerized ethylenically unsaturated ester in the copolymer to be changed by transesterification or by hydrolysis and subsequent reesterification.
  • Such copolymers are described, for example, in WO 01/38461, EP-A 1 028 155, EP-A 0 743 974 and WO 96/18708, to which reference is hereby made in full.
  • the weight ratio of component B to component A in the additive mixture is preferably 1: 2 to 1:99, particularly preferably 1: 4 to 1:99 and in particular 1:30 to 1:99.
  • the weight ratio of a mixture of component A and component B to component C is preferably 1: 250 to 10: 1, particularly preferably 1:20 to 5: 1 and in particular 1:10 to 4: 1.
  • Another object of the present invention is the use of the additive mixture described above for the additivation of mineral oil products.
  • the additive mixture is particularly preferably used to improve the lubricity properties before mineral oil products.
  • the mineral oil products are preferably fuel oils and lubricants.
  • Suitable fuel oils are fuels, e.g. B. petrol and middle distillates, such as diesel fuels, heating oil, especially heating oil EL, or kerosene, with diesel fuel and heating oil being preferred.
  • Diesel fuels are, for example, petroleum raffinates, which usually have a boiling range of 100 to 400 ° C. These are mostly distillates with a 95% point up to 360 ° C or beyond. However, these can also be so-called “ultra low sulfur diesel” or "city diesel", characterized by a 95% point of, for example, a maximum of 345 ° C. and a sulfur content of a maximum of 0.005% by weight or by a 95% point of, for example, 285 ° C. and a sulfur content of maximum 0.001% by weight.
  • diesel fuels obtainable by refining, those that are produced by Fischer-Tropsch processes or analog processes from synthesis gas, e.g. B.
  • the additive mixture according to the invention is particularly preferred for additizing diesel fuels with a low sulfur content, ie. H. with a sulfur content of less than 0.05% by weight, preferably less than 0.02% by weight, in particular less than 0.005% by weight and especially less than 0.001% by weight of sulfur, and for the addition of Low sulfur fuel oils, d. H. with a sulfur content of less than 0.20% by weight, preferably less than 0.10% by weight, in particular less than 0.05% by weight and especially less than 0.005% by weight of sulfur.
  • a low sulfur content ie. H. with a sulfur content of less than 0.05% by weight, preferably less than 0.02% by weight, in particular less than 0.005% by weight and especially less than 0.001% by weight of sulfur
  • Low sulfur fuel oils d. H. with a sulfur content of less than 0.20% by weight, preferably less than 0.10% by weight, in particular less than 0.05% by weight and especially less than 0.005% by weight of sulfur.
  • Another object of the present invention is a
  • Fuel composition comprising a main amount of a hydrocarbon fuel oil and an effective amount of the additive mixture according to the invention and optionally at least one further additive.
  • the additive mixture according to the invention is preferably present in the fuel oil in an amount of 1 to 1000 ppm by weight, particularly preferably 10 to 500 ppm by weight and in particular 50 to 200 ppm by weight, based on the total amount of the additive-containing fuel oil, in front.
  • Another object of the present invention is a lubricant composition containing an effective amount of an additive mixture according to the invention, a lubricant and optionally at least one further additive.
  • the invention also relates to an additive concentrate containing the additive mixture according to the invention, at least one solvent or diluent and, if appropriate, at least one further additive.
  • Suitable diluents are, for example, fractions obtained in petroleum processing, such as kerosene, naphtha or brightstock. Also suitable are aromatic and aliphatic hydrocarbons, alkoxyalkanols and C ⁇ -C Alko-alkanols, such as methanol, ethanol, propanol, isopropanol, butanol, pentanol, He- xanol, heptanol, octanol, 2-ethylhexanol, nonanol, decanol and their positional isomers.
  • aromatic and aliphatic hydrocarbons such as methanol, ethanol, propanol, isopropanol, butanol, pentanol, He- xanol, heptanol, octanol, 2-ethylhexanol, nonanol, decanol and their positional isomers.
  • diluent used are naphtha, kerosene, diesel fuels, aromatic hydrocarbons, such as Solvent Naphtha heavy, Solvesso or Shellsol ®, Al alkanols such as 2-ethyl hexanol, and mixtures of these solvents and diluents.
  • the additive mixture according to the invention is preferably present in the concentrates in an amount of 0.1 to 80% by weight, particularly preferably 1 to 70% by weight and in particular 20 to 60% by weight, based on the total weight of the concentrate, in front.
  • Suitable additives which can be contained in the fuel or concentrate according to the invention in addition to the additive mixtures according to the invention, in particular for diesel fuels include detergents, corrosion inhibitors, dehazers, demulsifiers, antifoam ("antifoam”), antioxidants, metal deactivators, multifunctional stabilizers, cetane number improvers , Combustion improvers, dyes, markers, solubilizers, antistatic agents, other customary lubricity improvers, additives which improve the cold properties, such as flow improvers (“MDFI”), paraffin dispersants (“WASA”) and the combination of the latter two additives (“WAFI”) ); and are described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition on CD-ROM, 1997, Wiley-VCH, Weinheim, Additives for Diesel Fuel.
  • MDFI flow improvers
  • WASA paraffin dispersants
  • WAFI combination of the latter two additives
  • the usual lubricity improvers include, for example, carboxylic acids, especially fatty acids, their esters, especially with polyols, mixtures of these acids and esters, ash-free N-acyl compounds, such as polyalkenylsuccinic acid amides, mixtures of the abovementioned acids and / or esters with these N-acyl compounds, such as they are described, for example, in WO 96/23855, bis (hydroxyalkyl) fatty amines or hydroxyacetamides.
  • carboxylic acids especially fatty acids, their esters, especially with polyols, mixtures of these acids and esters
  • ash-free N-acyl compounds such as polyalkenylsuccinic acid amides, mixtures of the abovementioned acids and / or esters with these N-acyl compounds, such as they are described, for example, in WO 96/23855, bis (hydroxyalkyl) fatty amines or hydroxyacetamides.
  • Suitable flow improvers include, for example, oil-soluble, polar nitrogen compounds, such as ammonium salts and / or amides of mono- or polycarboxylic acids or sulfonic acids, copolymers of ethylene and unsaturated carboxylic acid esters, comb polymers, saturated hydrocarbons, poly (meth) acrylic acid and mixtures of the aforementioned flow improvers.
  • oil-soluble, polar nitrogen compounds such as ammonium salts and / or amides of mono- or polycarboxylic acids or sulfonic acids, copolymers of ethylene and unsaturated carboxylic acid esters, comb polymers, saturated hydrocarbons, poly (meth) acrylic acid and mixtures of the aforementioned flow improvers.
  • Preferred flow improvers are comb polymers whose side chains contain at least 6, preferably at least 10, atoms.
  • Preferred comb polymers are described, for example, in EP 1 028 155, to which reference is hereby made in full.
  • paraffin dispersants are described, for example, in WO 00/23541, to which reference is hereby made in full.
  • Another object of the present invention is the use of component C to increase the lubricity-improving effect of a mixture of components A and B.
  • the present invention relates to a method for producing a fuel oil or lubricant composition, in which a fuel oil or a lubricant with components A, B and C, which are defined as described above, is mixed or separately, simultaneously or in succession.
  • the fuel oil or the lubricant can be mixed with the additive mixture according to the invention, in which all three components A, B and C are contained. Alternatively, they can be mixed with a mixture of two components and with the third separate component or with the three components A, B and C in separate form. In the last two alternatives, the addition of the separate components can be carried out simultaneously or sequentially otherwise, the order in the sequential addition is arbitrary.
  • synergistically effective combination of components A, B and C in the additive mixture according to the invention leads to a significant improvement in the lubricity of mineral oil products additized therewith in comparison to additives of the prior art.
  • component AB a commercially available mixture of saturated and unsaturated monocarboxylic acids and resin acids called Sylfat; Arizona Chemicals
  • -C2 a mixture of additive Cl with an ethylene-vinyl acetate copolymer with an average vinyl acetate content of 30% by weight.
  • -C3 a mixture of additive Cl with a co-additive (ethylenediaminetetraacetic acid amidated with a ditallow fatty amine) in a weight ratio of 4: 3.
  • the lubricity of non-additive, of additive with only one component AB or C and of additive according to the invention was tested with the HFRR test according to ISO 12156-1 and the observed lubricity was compared.
  • the following table shows the WS 1.4 ⁇ m value, which represents the size of the wear scar.
  • a WS (wear scar) value of less than 460 ⁇ m indicates sufficient lubricity.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

L'invention concerne un mélange d'additifs contenant au moins un acide monocarboxylique aliphatique, au moins un acide carboxylique polycyclique et au moins un copolymère à base d'oléfines inférieures et d'esters insaturés. L'invention concerne en outre l'utilisation de ce mélange d'additifs pour ajouter des additifs à des produits minéraux, ainsi que des compositions d'huiles combustibles et de lubrifiants, de même que des concentrés contenant ledit mélange d'additifs.
PCT/EP2004/003253 2003-03-27 2004-03-26 Melange d'additifs pour ameliorer les proprietes du pouvoir lubrifiant de produits mineraux WO2004085580A1 (fr)

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DE10313883A DE10313883A1 (de) 2003-03-27 2003-03-27 Additivgemisch zur Verbesserung der Schmierfähigkeitseigenschaften von Mineralölprodukten
DE10313883.8 2003-03-27

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8226951B2 (en) 2004-04-07 2012-07-24 Pfizer Inc. Methods for treating bone cancer by administering a nerve growth factor antagonist antibody
CN101370916B (zh) * 2006-01-18 2012-11-07 巴斯夫欧洲公司 单羧酸和多环烃化合物的混合物在改善燃料添加剂浓缩物的储存稳定性中的用途

Citations (8)

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Publication number Priority date Publication date Assignee Title
WO1996018708A1 (fr) * 1994-12-13 1996-06-20 Exxon Chemical Patents Inc. Compositions de fuel-oil
GB2308129A (en) * 1995-11-29 1997-06-18 Lubrizol Corp Pour point depressant composition
EP0807676A2 (fr) * 1996-05-17 1997-11-19 Ethyl Petroleum Additives Limited Additifs et compositions de combustible
WO1998004656A1 (fr) * 1996-07-31 1998-02-05 Elf Antar France Carburant pour moteurs diesel a faible teneur en soufre
US5772705A (en) * 1994-06-09 1998-06-30 Exxon Chemical Patents Inc. Fuel oil compositions
WO2001038461A1 (fr) * 1999-11-23 2001-05-31 The Associated Octel Company Limited Composition
EP1116780A1 (fr) * 2000-01-11 2001-07-18 Clariant GmbH Additif polyfonctionnel pour huiles combustibles
EP1209215A2 (fr) * 2000-11-24 2002-05-29 Clariant GmbH Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5772705A (en) * 1994-06-09 1998-06-30 Exxon Chemical Patents Inc. Fuel oil compositions
WO1996018708A1 (fr) * 1994-12-13 1996-06-20 Exxon Chemical Patents Inc. Compositions de fuel-oil
GB2308129A (en) * 1995-11-29 1997-06-18 Lubrizol Corp Pour point depressant composition
EP0807676A2 (fr) * 1996-05-17 1997-11-19 Ethyl Petroleum Additives Limited Additifs et compositions de combustible
WO1998004656A1 (fr) * 1996-07-31 1998-02-05 Elf Antar France Carburant pour moteurs diesel a faible teneur en soufre
WO2001038461A1 (fr) * 1999-11-23 2001-05-31 The Associated Octel Company Limited Composition
EP1116780A1 (fr) * 2000-01-11 2001-07-18 Clariant GmbH Additif polyfonctionnel pour huiles combustibles
EP1209215A2 (fr) * 2000-11-24 2002-05-29 Clariant GmbH Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8226951B2 (en) 2004-04-07 2012-07-24 Pfizer Inc. Methods for treating bone cancer by administering a nerve growth factor antagonist antibody
CN101370916B (zh) * 2006-01-18 2012-11-07 巴斯夫欧洲公司 单羧酸和多环烃化合物的混合物在改善燃料添加剂浓缩物的储存稳定性中的用途

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