EP1789520A1 - Additifs de polyamines destines aux carburants et lubrifiants - Google Patents

Additifs de polyamines destines aux carburants et lubrifiants

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Publication number
EP1789520A1
EP1789520A1 EP05771862A EP05771862A EP1789520A1 EP 1789520 A1 EP1789520 A1 EP 1789520A1 EP 05771862 A EP05771862 A EP 05771862A EP 05771862 A EP05771862 A EP 05771862A EP 1789520 A1 EP1789520 A1 EP 1789520A1
Authority
EP
European Patent Office
Prior art keywords
use according
formula
additive
fuel
additives
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05771862A
Other languages
German (de)
English (en)
Inventor
Jörn KARL
Marco Bergemann
Mirjam Herrlich-Loos
Georg Schäper
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP05771862A priority Critical patent/EP1789520A1/fr
Publication of EP1789520A1 publication Critical patent/EP1789520A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/56—Amides; Imides
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • 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
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
    • 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
    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
    • C10M149/22—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • 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
    • 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
    • C10M2215/28—Amides; Imides
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • 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 the use of polyamines having at least one terminal secondary or tertiary amine function as a detergent additive for fuels and lubricants; Additive concentrates containing such polyamines; Fuels and lubricants additized with these polyamines and processes for their production.
  • detergent additives include, in particular, polyalkenyl succinimides. These usually find various uses in combination with other additives in fuels and lubricants, cf. e.g. EP-A-0264247, EP-A-0271937 and WO-A-98/42808.
  • WO-A-98/42808 describes the use of special reaction products of a polyalkenyl derivative of a monoethylenically unsaturated C 4 -C 10 -dicarboxylic acid with a polyamine having terminal primary amine groups as a detergent additive for low-sulfur diesel fuels.
  • WO 2004/024851 describes synergistic additive mixtures for fuels and lubricants from an additive with detergent action and a partial or completely neutralized fatty acid.
  • detergent additives include compounds having a hydrophobic hydrocarbon radical with a Mn of from 85 to 20,000, whose polar head group is selected from carboxylic acid-derived groups having hydroxyl and / or amino and / or amido and / or imido groups.
  • Dicarboxylic acid imides of polyalkylenepolyamines with terminal secondary or tertiary amine end groups in the end product were not investigated therein.
  • a disadvantage of the additives or Additivgemi- described in the prior art is that to achieve a cleansing or reinhaltenden effect relatively high dosing rates are required.
  • the object of the present invention was therefore to provide improved detergent additives for fuel and lubricant compositions, in particular diesel fuels, which are effective even at lower metering rates and in particular effectively reduce nozzle coking.
  • linear polyamines having at least one terminal secondary or tertiary amine function as a detergent additive for fuels and lubricants.
  • a first subject of the invention relates to the use of a compound of general formula I.
  • R 1 , R 2 , R 3 and R 4 are independently H or C 1 -C 10 alkyl, wherein
  • R 1 and R 2 and R 3 and R 4 are not simultaneously H; or R 1 and R 2 together with the nitrogen atom to which they are attached form a C 4 -C 6 -dicarboximide ring which is substituted by at least one polyalkenyl radical R having a number-average molecular weight M n of from 100 to 2,500 and wherein preferably at the same time R 3 and R 4 are C 1 -C 10 -alkyl; y is an integer value of 1 to 100, such as 1 to 50, 1 to 20 or 1 to 10, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 and x and z are independently an integer from 2 to 12, such as 2 to 10, 2 to 8, 2 to 6 or 2, 3 or 4, as a detergent additive for fuels and lubricants.
  • Diesel engines for diesel fuels and especially for the purpose of reducing jet coking
  • additives according to the invention are suitable for reducing jet coking in diesel engines with direct fuel injection, in particular according to the "common rail”, “pump nozzle” or “pump-line-nozzle” principle.
  • a “reduction in jet coking” is understood as meaning a partial or complete reduction in the rate of jet coking observed in comparison to the unadditized state (ie in the absence of a compound of the formula I in the fuel), in a standard engine test, in particular in one described below Motor test for determining the percentage airflow reduction.
  • a first preferred group of compounds comprises compounds of the following general formula II
  • R is a polyisobutenyl radical.
  • the polyisobutenyl radical has in particular a Mn of about 500 to 1000.
  • a second preferred group of compounds comprises compounds of the formula I in which R 1 , R 2 , R 3 and R 4 independently of one another are H or C 1 -C 10 -alkyl, where R 1 and R 2 and R 3 and R 4 are not are simultaneously H, and x, y and z have the abovementioned meanings. Such compounds are therefore terminated by two secondary and / or tertiary amine functions.
  • R 3 and R 4 independently of one another are H or C 1 -C 8 -, C 1 -C 6 -, C 1 -C 5 - or C 1 -C 4 -alkyl, but R 3 and R 4 can not be H at the same time; or wherein R 3 and R 4 are simultaneously C 1 -C 8 -, C 1 -C 6 -, C 1 -C 5 - or C 1 -C 4 -alkyl.
  • R 3 and R 4 preferably have the same meanings.
  • reaction products or mixtures obtained in the preparation of compounds of the formula I, optionally partially purified are used.
  • a reaction product comprising an imide compound of formula I, such as a compound of formula II, wherein the reaction product is obtainable by reacting a cyclic C 4 -C 6 - dicarboxylic anhydride substituted with at least one polyalkenyl radical R substituted is, which has a number average molecular weight Mn of 100 to 2500, with a polyamine of the formula III
  • detergent additives described above is usually in combination with at least one other conventional fuel or lubricant additive, which will be described in more detail later.
  • the additive of the formula I is added in an amount of about 1 to 200 mg / kg of fuel, more preferably in a dosage of 1 to 100, 1 to 50, 1 to 30, 2 to 20 or 2 to 16 mg / kg of fuel ,
  • the addition of the additive of the formula I is preferably carried out in an amount which has a degree of coking of not more than 80%, preferably not more than 70%, such as e.g. 0 to 65%, 2 to 50% or 5 to 40%, determined according to CEC F23 A 01 (in a XUD9 test motor at 0.1 mm needle stroke) over the percentage airflow obstruction.
  • Another object of the invention relates to fuel compositions umfas ⁇ transmitted in a major amount of in the range of 100 to 500 0 C, such as 150 to 400 0 C or 160 to 360 0 C, boiling hydrocarbon fuel, in particular a co- distillate fuel, such as diesel fuel, an effective amount of at least one detergent additive of formula I, as defined above.
  • the invention also relates to lubricant compositions comprising, in a conventional lubricant, at least an effective amount of at least one detergency additive of the formula I, as defined above.
  • the invention also relates to additive concentrates comprising at least one detergent additive of the formula I as defined above, in combination with at least one further customary fuel or lubricant additive additive.
  • the additive according to the invention is preferably present in the concentrates in an amount of from 0.1 to 80% by weight, more preferably from 1 to 70% by weight and in particular from 20 to 60% by weight, based on the total weight of the concentrate, in front.
  • the invention also provides a process for the preparation of a fuel composition having an improved fuel inlet system cleaning action, wherein an effective amount of at least one compound according to the above definition or of an additive concentrate as defined above is added to a commercial fuel composition.
  • the invention provides a process for the preparation of a lubricant composition having an improved detergent action, wherein an effective amount of at least one compound according to the above definition of an additive concentrate according to the above definition is added to a commercially customary lubricant composition.
  • radicals R 1, R 2, R 3 and R 4 is C 1 -C 10 -alkyl insbeson particular for C r C 4 -alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl, sec Butyl, isobutyl, tert-butyl, and the long-chain radicals pentyl, hexyl, heptyl, octyl, nonyl and decyl, and the one or more times, such as mono-, di- or tri-branched analogs thereof.
  • dicarboxylic acids are the monounsaturated forms of succinic, glutaric and adipic acids.
  • These compounds can be obtained, for example, by reacting a dicarboxylic acid substituted by a hydrophobic hydrocarbon radical or a dicarboxylic acid derivative substituted by a hydrophobic hydrocarbon radical with an amine which has at least one NH 2 group.
  • a Carbon Tar is reacted anhydride.
  • the molar ratio of dicarboxylic acid (derivative) groups to hydrocarbon radical is in the range of 0.8 to 2, or 0.9 to 1, 5 or 0.9 to 1.05, e.g. also described in EP-A-0 355 895 and 0 587 381.
  • product mixtures which comprise dicarboxylic acid monoamides, dicarboxylic acid diamides, ammonium salts of dicarboxylic acid monoamides, dicarboxylic acid monoamide monoesters, amidines and dicarboxylic acid mono- and diimides.
  • Suitable additives according to the invention are both the individual acylation products mentioned as well as their mixtures.
  • dicarboxylic acid imides in particular dicarboxylic acid monoimides, and mixtures containing them.
  • the imide content is in particular in a range of from 1 to 100 mol%, as described, for example, in US Pat. 10 to 95 mol% or 30 to 90 mol%.
  • the coupling ratio (PIBSA / AMIN) is in the range of 0.5 to 2 based on the ratio of succinic groups to amine, e.g. 0.8 to 1.2, more preferably 0.9 to 1.05.
  • Suitable amines for the reaction with the dicarboxylic acid or the dicarboxylic acid derivative are polyamines of the above formula III.
  • Suitable polyamines are, for example, the mono-N, N-dialkyl derivatives of diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, dipropylenetriamine, tripropylenetetramine, tetrapropylenepentamine, pentapropylenhexamine, dibutylenetriamine, tributylenetetramine, tetrabutylenepentamine, pentabutylenhexamine.
  • N N-Dimethyldimethylentriamin, N 1 N- Diethyldimethylentriamin, N, N-Dipropyldimethylentriamin, N, N-Dimethyldiethylen-1, 2-triamine, N, N-Diethyldiethylen-1, 2-triamine, N, N-Dipropyldiethylen-1, 2-triamine, N 1 N- Dimethyldipropylen-1, 3-triamine (ie DMAPAPA), N, N-Diethyldipropylen-1, 3-triamine, N, N-Dipropyldipropylen-1, 3-triamine, N, N-dimethyldibutylene-1,4-triamine, N 1 N- Diethyldibutylen-1, 4-triamine, N, N-Dipropyldibutylen-1, 4-triamine, N 1 N- Dimethyldipentylen-1, 5-triamine, N,
  • Linear polyamines terminated with identical N, N-dialkylamino groups such as bis [2- (N, N-dimethylamino) ethyl] amine, bis [2- (N, N-diethylamino) ethyl] amine, bis [2- (N, N-dipropylamino) ethyl] amine, bis [3- (N, N-dimethylamino) propyl] amine, bis [3- (N, N-diethylamino) propyl] amine, bis [3- (N, N-dipropylamino) propyl ] amine, bis [4- (N, N-dimethylamino) butyl] amine, bis [4- (N, N-diethylamino) butyl] amine, bis [4- (N, N-)
  • Dipropylamino) butyl] amine bis [5- (N, N-dimethylamino) pentyl] amine, bis [5- (N, N-diethylamino) pentyl] amine, bis [5- (N, N-dipropylamino) pentyl] amine , Bis [6- (N, N-dimethylamino) hexyl] amine, bis [6- (N, N-diethylamino) hexyl] amine, bis [6- (N, N-dipropylamino) hexyl] amine and the like with identical Monoalkylamino-terminated analogues. Also suitable are corresponding polyamines which are terminated with different mono- or dialkylamino groups, and mixtures of such compounds.
  • Preferred alcohols are those having 6 to 16 carbon atoms. Particularly preferred is 2-ethylhexanol.
  • Suitable phenols include phenol, naphthol, (o, p) -alkylphenols and salicylic acid.
  • German Patent Application DE-A-10123553.4 describes the preparation of a polyolefin-substituted carboxylic acid or a derivative thereof by the reaction of a polyalkene with a monounsaturated acid or its derivative, the polyalkylene being bonded to the double bond in an ene reaction the acid component attaches.
  • Other methods are e.g. also described in WO-A-98/42808, to which reference is hereby made.
  • the polyamine products of the invention can be used as additives (usually in the form of additive packages or concentrates) for fuels, in particular diesel fuel, heating oil, kerosene, or in general middle distillates, and gasoline, or lubricants.
  • the polyamines of the invention When used as diesel fuel additives, they contain an effective amount of polyamine.
  • the diesel fuels contain from about 1 to 5000 ppm, or from about 5 to 1000 ppm, such as about 5 to 200 or 10 to 100 ppm, based on the total weight of the diesel fuel.
  • the diesel fuel additive mixtures used contain at least one further additive selected from among other conventional detergents, corrosion inhibitors, dehazers, demulsifiers, antifoams, antioxidants, metal deactivators, multifunctional stabilizers, cetane number improvers, combustion improvers, colorants, markers, solubilizers, antistatic agents, lubricity improvers.
  • the polyamines according to the invention can also be used as additives for heating oil. It is used in an effective amount, suitably in an amount of from 10 to 1000 ppm, preferably from 50 to 500 ppm, based on the total weight of the heating oil.
  • This may contain at least one further additive which may be selected from corrosion inhibitors, demulsifiers, antifoaming agents, antioxidants, metal deactivators, ferrocenes and deodorants.
  • polyamines according to the invention can also be used as additives for gasoline fuels. These contain an effective amount of polyamines of the invention, suitably from 1 to 5000 ppm, or from about 5 to 1000 ppm, e.g. about 5 to 200 or 10 to 100 ppm, based on the total weight of the gasoline.
  • the gasoline fuel additive mixtures may also contain at least one further additive selected from among other conventional detergent additives, carrier oils, lubricity improvers, solvents and corrosion inhibitors.
  • polyamines according to the invention are also suitable for lubricant compositions containing an effective amount of products according to the invention, suitably from 0.1 to 10% by weight, preferably from 0.5 to 5% by weight, based on the total weight of the lubricant composition.
  • the lubricant compositions may also contain other additives especially selected from lubricity improvers, anti-wear additives, corrosion inhibitors, VI improvers.
  • Detergent-active additives have at least one hydrophobic hydrocarbon radical having a number-average molecular weight (Mn) of from 85 to 20,000 and at least one polar group selected from: (a) mono- or polyamino groups having up to 6 nitrogen atoms, at least one nitrogen atom having basic properties,
  • polyoxy-C 2 -C 4 -alkylene groups terminated by hydroxyl groups, mono- or polyamino groups, wherein at least one nitrogen atom has basic properties, or terminated by carbamate groups,
  • the preparation route is by chlorination and subsequent amination or by oxidation of the double bond with air or ozone to carbonyl - or carboxyl compound and subsequent amination under reductive (hydrogenating) conditions.
  • amination here can be used the same amines as above for the reductive amination of the hydroformylated reactive polyisobutene.
  • Corresponding additives based on polypropene are described in particular in WO-A 94/24231 which is hereby incorporated by reference.
  • monoamino groups (a) containing additives are the polyisobutene epoxides by reaction with amines and subsequent dehydration and reduction of the amino alcohols available compounds, as described in particular in DE-A 196 20 262, to which hereby fully reference is taken.
  • These reaction products generally comprise mixtures of pure nitropolyisobutenes (eg, alpha, beta-dinitropolyisobutene) and mixed hydroxynitropolyisobutenes (eg, alpha-nitro-beta-hydroxypolyisobutene).
  • Polyoxy-C 2 - to C 4 -alkylene (d) containing additives are preferably polyether or polyether amines, which by reaction of C 2 - to C 6 o-alkanols, C 6 - to C 30 alkanediols, mono- or di- C 2 -C 30 alkylamines, C 30 - alkylcyclohexanols or C r C 30 alkyl phenols having 1 to 30 mol ethylene oxide and / or propylene oxide and / or butylene oxide per hydroxyl group or amino group and, in the case of the polyetheramines, by subsequent reductive amination with ammonia, monoamines or polyamines are available.
  • Such products are described in particular in EP-A 310 875, EP-A 356 725, EP-A 700 985 and US-A 4 877 416, to which reference is hereby fully made.
  • polyethers such products also fulfill carrier oil properties. Typical examples thereof are tridecanol or isotridecanol butoxylates, isononylphenol butoxylates and also polyisobutenol butylates and propoxylates, and the corresponding reaction products with ammonia. niak.
  • Carboxylic ester group (s) containing additives are preferably esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, in particular those having a minimum viscosity of 2 mm 2 at 100 0 C, as in particular
  • Carboxylic anhydride-derived groupings containing hydroxyl and / or amino and / or amido and / or imido groups (g) additives are preferably corresponding derivatives of dicarboxylic anhydrides, more preferably of succinic anhydride.
  • groups derived from carboxylic acid anhydrides does not necessarily require that the carboxylic acid anhydrides actually have to be used. Of course, such groups can also by the implementation of other Carbonklarederiva ⁇ te, which have the required activity, for.
  • carboxylic acid halides or by the reaction of the carboxylic acid itself, if appropriate Aktivierungsdorfnah ⁇ men are taken, are obtained.
  • Carboxylic acid anhydrides are particularly suitable derivatives for the conversion into the groupings mentioned.
  • the polar grouping of component A is particularly preferably a grouping with hydroxyl and / or amino and / or amido and / or imido groups (g) derived from carboxylic anhydrides, in particular with amido and / or imido groups, ie. H. to N-acyl groups.
  • hydrophobic hydrocarbon radical of the above-described detergent additive (a) bids (g) and the hydrophobic radical R of polyamine detergents of the formulas I and II according to the invention are preferably a homo- or Copolymer residue whose repeating units are derived from monomers selected from propene, n-butene and isobutene and mixtures thereof.
  • the homo- or copolymer radical is a polyisobutene radical.
  • the homo- or copolymer radical is a radical derived from so-called "reactive" polyisobutenes, which differ from the "low-reactivity" polyisobutenes by their content distinguish terminally arranged double bonds.
  • Reactive polyisobutenes differ from low-reactive ones in that they have at least 50 mole%, preferably at least 60 mole%, and more preferably at least 80 mole%, based on the total number of polyisobutene macromolecules, of terminal double bonds.
  • such reactive polyisobutenes have a number average molecular weight in the range of 100 to 20,000.
  • Suitable for the preparation of fuel additives are, in particular, reactive polyisobutenes which have a number-average molecular weight in the range from 100 to 3,000, such as 200 to 2,500 or 500 to 1,500, eg. B. a number average molecular weight of about 550, about 800 or about 1,000.
  • Suitable for the preparation of lubricant additives are in particular reactive polyisobutenes having a number average molecular weight in the range of 1000 to 15,000, more preferably 1300 to 12500 and most preferably 2000 to 10,000, z. B. a number average molecular weight of about 1500, about 2000 or about 2300.
  • the reactive polyisobutenes preferably have a polydispersity of less than 3.0, in particular less than 1, 9 and particularly preferably less than 1, 7 or less than 1.5.
  • Polydispersity is understood to mean the quotient of weight average molecular weight M w divided by the number average molecular weight M N.
  • Particularly suitable reactive polyisobutenes are, for.
  • Other number-average molecular weights can be adjusted in a manner known in principle by mixing polyisobutenes of different number-average molecular weights or by extractive enrichment of polyisobutenes of specific molecular weight ranges.
  • C2 Cold flow improver
  • the cold properties improving additives include Weg ⁇ distillate flow improvers (“MDFI”), paraffin dispersants (“WASA”) and the combination of the two additives (“WAFI”).
  • Suitable cold-flow improvers include, in particular, the following active compound groups, as described, for example, in US Pat. in WO 95/33805 are described:
  • the monomer is preferably selected from alkenylcarboxylic acid esters, (meth) acrylic esters and olefins.
  • Suitable olefins are, for example, those having 3 to 10 carbon atoms and having 1 to 3, preferably 1 or 2, in particular having one, carbon-carbon double bond.
  • the carbon-carbon double bond can be arranged both terminally ( ⁇ -olefins) and internally.
  • ⁇ -olefins particularly preferably ⁇ -olefins having 3 to 6 carbon atoms, such as propene, 1-butene, 1-pentene and 1-hexene.
  • Suitable (meth) acrylic esters are, for example, esters of (meth) acrylic acid with C r C 10 -alkanols, in particular with methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, isobutanol, tert-butanol, pentanol, hexanol, heptanol , Octanol, 2-ethylhexanol, nonanol and decanol.
  • Suitable alkenylcarboxylic esters are, for example, the vinyl and propenyl esters of carboxylic acids having 2 to 20 carbon atoms, the hydrocarbon radical of which may be linear or branched. Preferred among these are the vinyl esters.
  • carboxylic acids with a branched hydrocarbon radical preference is given to those whose branching is in the ⁇ -position to the carboxyl group, the ⁇ -carbon atom being particularly preferably tertiary, ie the carboxylic acid being a so-called neocarboxylic acid.
  • the hydrocarbon radical of the carboxylic acid is linear.
  • alkenylcarboxylic esters examples include vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, vinyl neopentanoate, vinyl hexanoate, vinyl neononanoate, vinyl neodecanoate and the corresponding propenyl esters, the vinyl esters being preferred.
  • a particularly preferred alkenyl carboxylic acid ester is vinyl acetate.
  • the ethylenically unsaturated monomer is selected from among alkenylcarboxylic acid esters.
  • copolymers which contain two or more mutually different alkenylcarboxylic acid esters in copolymerized form, these differing in the alkenyl function and / or in the carboxylic acid group. Also suitable are copolymers which, in addition to the alkenylcarboxylic ester (s), contain at least one olefin and / or at least one (meth) acrylic acid ester in copolymerized form.
  • the ethylenically unsaturated monomer is copolymerized in the copolymer in an amount of preferably 1 to 50 mol%, particularly preferably 10 to 50 mol% and in particular of 5 to 20 mol%, based on the total copolymer.
  • the copolymer (aa) preferably has a number average molecular weight M n of from 1000 to 20 000, more preferably from 1000 to 10000 and in particular from 1000 to 6000.
  • Comb polymers (ab) are, for example, those described in "Comb-Like Polymers, Structure and Properties", N.A. Plate and V.P. Shibaev, J. Poly. Be. Macromolecular Revs. 8, pages 117 to 253 (1974) are described. Of the described there are spielvati comb polymers of the formula II suitable
  • D is R 17 , COOR 17 , OCOR 17 , R 18 , OCOR 17 or OR 17 ,
  • E is H, CH 3 , D or R 18 ,
  • G is H or D
  • J is H, R 18 , R 18 is COOR 17 'aryl or heterocyclyl,
  • K is H, COOR 18 , OCOR 18 , OR 18 or COOH
  • L is H, R 18 COOR 18 , OCOR 18 , COOH or aryl, in which
  • R 17 is a hydrocarbon radical having at least 10 carbon atoms, preferably having 10 to 30 carbon atoms,
  • R 18 is a hydrocarbon radical having at least one carbon atom, preferably having 1 to 30 carbon atoms, m is a molar fraction in the range of 1, 0 to 0.4 and n stands for a mole fraction in the range of 0 to 0.6 ,
  • Preferred comb polymers are, for example, by the copolymerization of maleic anhydride or fumaric acid with another ethylenically unsaturated monomer, for example with an ⁇ -olefin or an unsaturated ester, such as vinyl acetate, and subsequent esterification of the anhydride or acid function with an alcohol available with at least 10 carbon atoms.
  • Further preferred comb polymers are copolymers of ⁇ -olefins and esterified comonomers, for example esterified copolymers of styrene and maleic anhydride or esterified copolymers of styrene and fumaric acid. Mixtures of comb polymers are also suitable.
  • Comb polymers may also be polyfumarates or polymaleinates.
  • homopolymers and copolymers of vinyl ethers are suitable comb polymers.
  • Suitable polyoxyalkylenes are, for example, polyoxyalkylene esters, ethers, - ester / ethers and mixtures thereof.
  • the polyoxyalkylene compounds preferably contain at least one, particularly preferably at least two, linear alkyl groups having from 10 to 30 carbon atoms and a polyoxyalkylene group having a molecular weight of up to 5,000.
  • the alkyl group of the polyoxyalkylene radical preferably contains from 1 to 4 carbon atoms.
  • Such polyoxyalkylene compounds are described, for example, in EP-A-0 061 895 and in US Pat. No. 4,491,455, to which reference is hereby fully made.
  • Preferred polyoxyalkylene esters, ethers and esters have the general formula III
  • R 19 and R 20 are each independently R 21 , R 21 OO, R 21 is -O-CO (CH 2 ) Z - or R 21 is -O-CO (CH 2 ) Z -CO-, wherein R 21 is is linear C 1-4 -alkyl, y is a number from 1 to 4, x is a number from 2 to 200, and z is a number from 1 to 4.
  • Preferred polyoxyalkylene compounds of the formula III in which both R 19 and R 20 are R 21 are polyethylene glycols and polypropylene glycols having a number average molecular weight of from 100 to 5,000.
  • Preferred polyoxyalkylenes of the formula III, in which one of the radicals R 19 is R 21 and the other is R 21 -CO-, are polyoxyalkylene esters of fatty acids having 10 to 30 carbon atoms, such as stearic acid or behenic acid.
  • Preferred polyoxyalkylene compounds in which both R 19 and R 20 are a radical R 21 -CO- are diesters of fatty acids having 10 to 30 carbon atoms, preferably stearic or behenic acid.
  • the polar nitrogen compounds (ad), which are suitably oil-soluble, may be both ionic and nonionic, and preferably have at least one, more preferably at least 2 substituents of the formula> NR 22 in which R 22 is a C 8 -C 40 - Hydrocarbon radical stands.
  • the nitrogen substituents may also be quaternized, that is in cationic form.
  • An example of such nitrogen compounds are ammonium salts and / or amides obtainable by reacting at least one amine substituted with at least one hydrocarbyl radical with a carboxylic acid having 1 to 4 carboxyl groups or with a suitable derivative thereof.
  • the amines preferably contain at least one linear C 8 -C 40 -alkyl radical.
  • Suitable primary amines are octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tetradecylamine and the higher linear homologs.
  • Suitable secondary amines are, for example, dioctadecylamine and methylbehenylamine.
  • amine mixtures in particular industrially available amine mixtures, such as
  • Suitable acids for the reaction are, for example, cyclohexane-1, 2-dicarboxylic acid, cyclohexene-1, 2-dicarboxylic acid, cyclopentane-1, 2-dicarboxylic acid, naphthalenedicarboxylic acid, phthalic acid, isophthalic acid,
  • Terephthalic acid and succinic acids substituted with long-chain hydrocarbon radicals.
  • polar nitrogen compounds are ring systems which carry at least two substituents of the formula -A-NR 23 R 24 , where A is a linear or branched aliphatic hydrocarbon group, optionally substituted by one or more groups selected from O , S, NR 35 and CO, is interrupted, and R 23 and R 24 are a C 9 -C 40 hydrocarbon radical optionally substituted by one or more groups selected from O, S, NR 35 and CO, un ⁇ interrupted and / or 1 SH and NR 35 R 36 is substituted by one or more substituents selected from OH, wherein R 35 is -C 4 -alkyl, which if appropriate by one or more groups that are selected from CO, NR 35 , O and S 1 interrupted, and / or by one or more radicals which are selected from NR 37 R 38 , OR 37 , SR 37 , COR 37 , COOR 37 , CONR 37 R 38 , aryl or heterocyclyl substituted ⁇ tuiert, where R 37 and R 37 and
  • A is a methylene or polymethylene group having 2 to 20 methylene units.
  • suitable radicals R 23 and R 24 are 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl, 2-ketopropyl, ethoxyethyl and propoxypropyl.
  • the cyclic system may be homocyclic, heterocyclic, condensed polycyclic or non-condensed polycyclic systems.
  • the ring system is carbo- or heteroaromatic, in particular carboaromatic.
  • polycyclic ring systems examples include condensed benzoid structures, such as naphthalene, anthracene, phenanthrene and pyrene, condensed nonbenzoic structures, such as azulene, indene, hydrindene and fluorene, uncondensed polycycles, such as diphenyl, heterocycles, such as quinoline, indole, dihydroindole, Benzofuran, coumarin, isocumarin, benzothiophene, carbazole, diphenylene oxide and diphenyl sulfide, non-aromatic or partially saturated ring systems, such as decalin, and dreidimen ⁇ sionale structures, such as ⁇ -pinene, camphene, bornylene, norbornane, norbornene, bicyclooctane and bicyclooctene.
  • condensed benzoid structures such as naphthalene, anthracene,
  • Suitable polar nitrogen compounds are condensates of long-chain primary or secondary amines with carboxyl-containing polymers.
  • Suitable polar nitrogen compounds are e.g. Also described in DE-A-198 48 621 of DE-A-196 22 052 or EP-B-398 101, to which reference is hereby genom ⁇ men.
  • Suitable sulfocarboxylic acids / sulfonic acids or their derivatives (ae) are, for example, those of the general formula IV
  • R 26 and R 27 are alkyl, alkoxyalkyl or polyalkoxyalkyl having at least 10 carbon atoms in the main chain, R 28 is C 2 -C 5 -alkylene, Z "is an anion equivalent and
  • a and B are alkyl, alkenyl or two substituted hydrocarbon radicals or together with the carbon atoms to which they are attached form an aromatic or cycloaliphatic ring system.
  • Suitable poly (meth) acrylic acid esters (af) are both homopolymers and copolymers of acrylic and methacrylic acid esters.
  • Preferred are acrylic ester homopolymers derived from CrC 40 alcohols.
  • the copolymer contains another, einpolyme- rinstrument different olefinically unsaturated monomer.
  • the weight average molecular weight of the polymer is preferably from 50000 to 500000.
  • a particularly preferred polymer is a copolymer of rylklare Methac- and methacrylic esters of saturated C 14 - and C 5 alcohols, wherein the acid groups are neutralized with hydrogenated tallow amine.
  • Suitable poly (meth) acrylates are described, for example, in WO 00/44857, to which reference is hereby fully made.
  • the usual lubricity improvers include, for example, carboxylic acids, especially fatty acids, their esters, especially with polyols, mixtures of these acids and esters, ashlessly burning N-acyl compounds, such as
  • Polyalkenylbemsteinklareamide mixtures of the aforementioned acids and / or esters with these N-acyl compounds, as described for example in WO 96/23855, bis (hydroxyalkyl) fatty amines or hydroxyacetamides.
  • Inventive additives are often formulated together with solvents or diluents.
  • Suitable diluents are, for example, fractions obtained in petroleum processing, such as kerosene, naphtha or bright stock.
  • aromatic and aliphatic hydrocarbons and alkoxyalkanols are especially for diesel fuels preferably used Diluents are naphtha, kerosene, diesel fuels, aromatic hydrocarbons, such as Solvent Naphtha suits, Solvesso R or Shellsol R, and mixtures of these solvents and diluents
  • additized fuels are petrol and middle distillates, such as diesel fuel, heating oil or kerosene, with diesel fuel being particularly preferred.
  • the diesel fuels are, for example, crude oil raffinates which Usually, for chhold have a boiling range of 100 to 400 0 C. These are mostly distillates with a 95% point up to 360 0 C or even beyond. However, these may 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 maximum sulfur content of 0.005% by weight or by a 95% point of for example 285 ° C and a sulfur content of at most 0.001 wt .-%.
  • diesel fuels obtainable by refining those obtainable by coal gasification or gas liquefaction (“gas to liquid (GTL) fuels) are also suitable.” Also suitable are mixtures of the abovementioned diesel fuels with regenerative fuels, such as biodiesel or bioethanol.
  • GTL gas to liquid
  • the additive according to the invention is particularly preferred for the addition of low-sulfur diesel fuels, 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.
  • PIBSA polyisobutenylsuccinic anhydride
  • the detergency of polyamines according to the invention compared to a commercial detergent additive was determined in a standardized test engine XUD9 (Peugeot engine) using the test method CEC F23 A 01.
  • the degree of coagulation of the nozzles was determined by the obstruction of an air flow at 0.1 mm needle stroke in the injection nozzle. 100% obstruction (flow restriction) means complete coking, 0% means no coking.
  • Diesel fuel according to EN 590 (S-content ⁇ 50 ppm)
  • Diesel fuel according to EN 590 (S-content ⁇ 10 ppm)
  • Relative to the comparative substance used additives of the invention show significantly better detergent activity at the same time lower dosage.

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  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
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  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

La présente invention concerne l'utilisation de polyamines ayant au moins une fonction amine terminale secondaire ou tertiaire comme additif détergent destiné aux carburants et lubrifiants. L'invention concerne des concentrés d'additifs contenant de telles polyamines ainsi que les carburants et lubrifiants contenant ces additifs de polyamines et leur procédé de production.
EP05771862A 2004-08-06 2005-08-05 Additifs de polyamines destines aux carburants et lubrifiants Withdrawn EP1789520A1 (fr)

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PCT/EP2005/008533 WO2006015818A1 (fr) 2004-08-06 2005-08-05 Additifs de polyamines destines aux carburants et lubrifiants
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See references of WO2006015818A1 *

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102690690A (zh) * 2012-06-13 2012-09-26 洛阳华燃石化科技有限公司 一种复合燃料油

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US20070214713A1 (en) 2007-09-20
NO20070929L (no) 2007-05-04
KR20070049178A (ko) 2007-05-10
US20100205852A1 (en) 2010-08-19
WO2006015818A1 (fr) 2006-02-16
BRPI0514160A (pt) 2008-06-03
JP2008509236A (ja) 2008-03-27
CN1993449A (zh) 2007-07-04
MX2007000844A (es) 2007-04-17
AU2005270367A1 (en) 2006-02-16
CA2576014A1 (fr) 2006-02-16

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