EP0938535A1 - Korrosionsschutz - und reinigungszusatz für treibstoffe, und treibstoffezusammensetzung - Google Patents

Korrosionsschutz - und reinigungszusatz für treibstoffe, und treibstoffezusammensetzung

Info

Publication number
EP0938535A1
EP0938535A1 EP97919109A EP97919109A EP0938535A1 EP 0938535 A1 EP0938535 A1 EP 0938535A1 EP 97919109 A EP97919109 A EP 97919109A EP 97919109 A EP97919109 A EP 97919109A EP 0938535 A1 EP0938535 A1 EP 0938535A1
Authority
EP
European Patent Office
Prior art keywords
compound
anhydride
additive
additive according
detergent
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.)
Granted
Application number
EP97919109A
Other languages
English (en)
French (fr)
Other versions
EP0938535B1 (de
Inventor
Laurent Germanaud
Guy Raoult
Danièle Eber
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.)
Elf Antar France SA
Elf Antar France
Original Assignee
Elf Antar France SA
Elf Antar France
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Elf Antar France SA, Elf Antar France filed Critical Elf Antar France SA
Publication of EP0938535A1 publication Critical patent/EP0938535A1/de
Application granted granted Critical
Publication of EP0938535B1 publication Critical patent/EP0938535B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • 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
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • 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

Definitions

  • the present invention relates to a bifunctional additive with detergent and anti-corrosion functions which, added to engine fuels, considerably reduces the problems associated with the corrosion of certain parts of the engine and the formation of deposits.
  • detergent additives consist of succinic diamides substituted by polyalkylenes, preferably polyisobutenes comprising from 35 to 300 carbon atoms, the diamide resulting from the condensation of a secondary amine of the type N-alkylp perazine on either a substituted succinic acid, an anhydride, an ester or a derivative monoamide; these additives are preferably used in petrol type fuels.
  • the present invention relates to a bifunctional additive with detergent and anti-corrosion properties, compatible with the other additives usually introduced into fuels, in particular diesel, making it possible to reduce and even prevent the formation of deposits at the level of injectors while limiting corrosion phenomena and maintaining good dispersion.
  • the present invention therefore relates to a bifunctional additive for motor fuels, in particular diesel fuels, with detergent and dispersing properties comprising amide or imide functions resulting from the condensation of a compound C consisting of a primary polyamine with a compound A consisting of at least one polyalkenyl carboxylic compound, diacid or anhydride and a compound B consisting of at least one carboxylic compound, monoacid or anhydride, linear or branched, the said additive being characterized in that it is obtained by mixing from 60 to 90% by weight of a compound A comprising from 2 to 20 carbon atoms per linear or branched alkenyl group having an average molecular weight varying from 200 to 3000, from 0.1 to 10% by weight of a compound B, comprising from 1 to 6 atoms of carbon per chain and from 10 to 30% of a compound C of general formula (I) below:
  • R and R 2 which may be identical or different, represent hydrogen or a hydrocarbon group comprising from 1 to 4 carbon atoms, n is an integer varying from 1 to 3, m is an integer varying from 1 to 10, and p is an integer equal to 0 or 1.
  • the compounds A, B and C are used in molar ratios A / B / C preferably corresponding to 1 / (0.1 to 1) / (l to 3) and are necessarily different from l / l / l. Indeed, there is always an excess of polyamine in the chosen composition which leads to leaving free a certain number of NH 2 terminations of polyamine C.
  • the C / A molar ratio varies from 1.3 to 2.0 and the ratio molar B / A varies from 0.1 to 0.8.
  • the combination of mono and dicarboxylic compounds in addition to a polyamine promotes the detergency and the anti-corrosion effect of the additives according to the invention. It corresponds to a synergistic effect of the combination of these three components between eu.
  • the average molar mass of the polyalkenyl carboxylic compounds according to the present invention preferably ranges from 200 to 2000 and most often from 200 to 1500. These compounds are well known in the prior art; they are in particular obtained by reaction of at least one ⁇ -olefin or at least one chlorinated hydrocarbon, both linear and branched, with maleic acid or anhydride.
  • This olefin or this chlorinated hydrocarbon comprises from 10 to 150 carbon atoms in general, preferably 15 to 80 carbon atoms and most often from 20 to 75 carbon atoms in their molecule.
  • 1 olefin can also be an oligomer, such as a dimer, a trimer or a tetramer or also a polymer of a lower olefin comprising from 2 to 10 carbon atoms such as ethylene, propylene, n-butene, isobutene, n-hexene, n-octene-1, methyl-2-heptene-1 and propyl -2 -propyl 5-hexene-l
  • the polyalkenyl carboxylic compounds are chosen from acid and succinct polyalkenyl anhydride derivatives, the anhydride index varying from 0.5 to 1
  • the compound B is preferably chosen from the group consisting of methacrylic acid, acrylic acid, maleic anhydride, succimic anhydride, malomic acid, fumaric acid and adipic acid
  • polyamines from the group consisting of diethylene triamine, dipropylene tnamine, triethylene tetramine, tetraethylene pentam and their substituted derivatives are preferred.
  • product C is added, that is to say the primary polyamine of formula (I) on the mixture of products A and B, that is to say the mixture of carboxylic hydrocarbons
  • product C is added, that is to say the primary polyamine of formula (I) on the mixture of products A and B, that is to say the mixture of carboxylic hydrocarbons
  • One usually operates by gradually introducing polyamine C to a solution in an organic solvent of this mixture of carboxylic hydrocarbons at ordinary temperature , then the temperature is usually raised between 65 and 250 ° C and preferably between 80 and 200 ° C
  • the organic solvent necessary for solubilization is chosen for its boiling point between 65 and 250 ° C and its capacity to removing the water formed by condensation of the polyamine on the mixture A + B, by azeotropic distillation of the water / solvent mixture.
  • the solvent is preferably chosen from the group consisting of benzene, toluene, xylenes, ethylbenzene and commercial hydrocarbon fractions, for example those distilling from 190 to 209 ° C. and containing 99% by weight of aromatic compounds .
  • a mixture of solvents was used, in particular a mixture of xylenes, or else a mixture of xylene / alcohol, in particular ethyl-2-hexanol on the one hand , facilitate the homogeneity of the medium and, on the other hand, favor the kinetics of the reaction.
  • the heating is maintained under reflux until the complete removal of the water contained, usually for 0.5 to 7 hours, preferably 1 to 5 hours.
  • a second object of the invention is a fuel mainly consisting of a middle distillate from a direct distillation cut of crude oil between 150 and 400 ° C or any other fuel with a cetane index greater than or equal to 30, and for a minor part by the additive (s) bifunctional (s) detergent (s) and anti-corrosion according to the first object of the invention.
  • the concentration of detergent and anti-corrosion additive (s) is greater than 50 ppm, preferably varying from 60 to 600 ppm.
  • the present invention it is possible to add to said fuel at least one additive from the group of oiliness additives, additives improving the cetane number, demulsifying additives and odor-modifying additives.
  • the present example describes the preparation of several samples of detergent and anti-corrosion bifunctional additives according to the invention.
  • a 2 polyisobutenyl succinic anhydride with an average molecular mass of 950 and an anhydride index equal to 0.8 milli-equivalent of potassium hydroxide per gram, sold under the reference ADX 104 by the company ADIBIS.
  • AMA methacrylic acid
  • TEPA tetraethylene pentamine
  • a mole of polyisobutenylsuccinic anhydride A, b moles of compound B, 25 ml of ethyl -2-hexanol and 25 ml of xylene are introduced successively into a 250 ml tetracol flask.
  • the mixture is stirred and heated to 100 ° C. until a homogeneous medium is obtained, then about 5 moles of tetraethylenepentamine or TEPA, C.
  • the whole is kept at the same temperature under reflux for three to four hours until a constant volume of extracted water is obtained (1.05 ml).
  • the products obtained have two mfra-red absorption bands characteristic of the imide functions at 1700 cm and the amide functions at 1670 cm.
  • the present example aims to emphasize the improvement of the detergent properties of the samples according to the invention according to the relative concentrations of A, B and C, after addition in a diesel fuel. It also aims to emphasize the synergistic effect of the combination according to the invention.
  • the engines are fitted with new injectors, the flow rates of which were measured prior to their installation, at different needle liftings from the injectors.
  • the injectors are disassembled, and their flow rates are measured for the same needle lifts.
  • the effectiveness of the detergent additives tested is compared on the basis of their percentage of residual flow rate (% dr) calculated by the formula below.
  • the additives according to the invention give residual flow rates much higher than those of diesel alone and of diesel additive by comparative detergent additives.
  • the present example aims to demonstrate the effectiveness of the additives according to the invention for cleaning already fouled injectors (curative effect) compared to the additives C according to the procedure described in Example II. Prior to each test, the injectors are pre-fouled with diesel fuel without additives for 6 hours according to the procedure described in Example II.
  • the present example aims to show the superiority of the additives according to the present invention compared to the comparative additives C.
  • Corrosion tests consist in determining the anti-corrosion effect of the additives in diesel fuel on samples of ordinary steel polished in the presence of synthetic seawater according to standard ASTM D665, for a period of 24 hours at the temperature of 60 ° C. They are expressed in% of corroded area.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Lubricants (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
EP97919109A 1996-09-18 1997-09-17 Korrosionsschutz - und reinigungszusatz für treibstoffe, und treibstoffezusammensetzung Expired - Lifetime EP0938535B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9611388 1996-09-18
FR9611388A FR2753455B1 (fr) 1996-09-18 1996-09-18 Additif detergent et anti-corrosion pour carburants et composition de carburants
PCT/FR1997/001634 WO1998012283A1 (fr) 1996-09-18 1997-09-17 Additif detergent et anti-corrosion pour carburants et composition de carburants

Publications (2)

Publication Number Publication Date
EP0938535A1 true EP0938535A1 (de) 1999-09-01
EP0938535B1 EP0938535B1 (de) 2002-03-06

Family

ID=9495858

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97919109A Expired - Lifetime EP0938535B1 (de) 1996-09-18 1997-09-17 Korrosionsschutz - und reinigungszusatz für treibstoffe, und treibstoffezusammensetzung

Country Status (16)

Country Link
US (1) US6083287A (de)
EP (1) EP0938535B1 (de)
JP (1) JP3763584B2 (de)
KR (1) KR100467280B1 (de)
AT (1) ATE214085T1 (de)
BR (1) BR9713201A (de)
CA (1) CA2266522C (de)
DE (1) DE69710913T2 (de)
DK (1) DK0938535T3 (de)
ES (1) ES2170386T3 (de)
FR (1) FR2753455B1 (de)
HU (1) HU223377B1 (de)
MY (1) MY116976A (de)
PT (1) PT938535E (de)
RU (1) RU2165448C2 (de)
WO (1) WO1998012283A1 (de)

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WO2010073233A2 (fr) 2008-12-23 2010-07-01 Total Raffinage Marketing Carburant de type gazole pour moteur diesel a fortes teneurs en carbone d'origine renouvelable et en oxygene
WO2011001352A1 (fr) 2009-07-03 2011-01-06 Total Raffinage Marketing Terpolymere ethylene/acetate de vinyle/esters insatures comme additif ameliorant la tenue a froid des hydrocarbures liquides comme les distillats moyens et les carburants ou combustibles
WO2012085865A1 (fr) 2010-12-23 2012-06-28 Total Raffinage Marketing Résines alkylphénol-aldéhyde modifiées, leur utilisation comme additifs améliorant les propriétés a froid de carburants et combustibles hydrocarbonés liquides
WO2012107454A1 (fr) 2011-02-08 2012-08-16 Total Raffinage Marketing Compositions liquides pour marquer les carburants et combustibles hydrocarbones liquides, carburants et combustibles les contenant et procede de detection des marqueurs
WO2013120985A1 (fr) 2012-02-17 2013-08-22 Total Raffinage Marketing Additifs ameliorant la resistance a l'usure et au lacquering de carburants de type gazole ou biogazole
WO2013189868A1 (fr) 2012-06-19 2013-12-27 Total Marketing Services Compositions d'additifs et leur utilisation pour ameliorer les proprietes a froid de carburants et combustibles
WO2014029770A1 (fr) 2012-08-22 2014-02-27 Total Marketing Services Additifs ameliorant la resistance a l'usure et au lacquering de carburants de type gazole ou biogazole
WO2014096323A1 (fr) 2012-12-21 2014-06-26 Total Marketing Services Composition gélifiée de carburant ou combustible hydrocarboné et procédé de préparation d'une telle composition
WO2014096326A1 (fr) 2012-12-21 2014-06-26 Total Marketing Services Utilisation d'un compose viscosifiant pour ameliorer la stabilite au stockage d'un carburant ou combustible hydrocarbone liquide
WO2014173844A1 (fr) 2013-04-25 2014-10-30 Total Marketing Services Additif pour ameliorer la stabilite a l'oxydation et/ou au stockage de carburants ou combustibles hydrocarbones liquides
WO2015181013A1 (fr) 2014-05-28 2015-12-03 Total Marketing Services Composition gelifiee de carburant ou combustible hydrocarbone liquide et procede de preparation d'une telle composition
EP3056527A1 (de) 2015-02-11 2016-08-17 Total Marketing Services Block-Copolymere und ihre Anwendung zur Verbesserung der Eigenschaften von Brenn- oder Kraftstoffen in kaltem Zustand
EP3056526A1 (de) 2015-02-11 2016-08-17 Total Marketing Services Block-Copolymere und ihre Anwendung zur Verbesserung der Eigenschaften von Brenn- oder Kraftstoffen in kaltem Zustand
EP3144059A1 (de) 2015-09-16 2017-03-22 Total Marketing Services Verfahren zur herstellung von mikrokapseln durch doppelemulsion
WO2018015667A1 (fr) 2016-07-21 2018-01-25 Total Marketing Services Utilisation de copolymeres pour ameliorer les proprietes a froid de carburants ou combustibles
WO2018033684A1 (fr) 2016-08-18 2018-02-22 Total Marketing Services Procede de fabrication d'un additif de lubrifiance pour carburant a faible teneur en soufre
WO2019121485A1 (fr) 2017-12-21 2019-06-27 Total Marketing Services Utilisation de polymères réticulés pour abaisser la température limite de filtrabilité de carburants ou combustibles
WO2019229331A1 (fr) 2018-05-29 2019-12-05 Total Marketing Services Composition de carburant et procede de fonctionnement d'un moteur a combustion interne
WO2020043619A1 (fr) 2018-08-28 2020-03-05 Total Marketing Services Composition d'additifs comprenant au moins un copolymère, un additif fluidifiant à froid et un additif anti-sédimentation
WO2020043618A1 (fr) 2018-08-28 2020-03-05 Total Marketing Services Utilisation de copolymères spécifiques pour améliorer les propriétés à froid de carburants ou combustibles
WO2020141126A1 (fr) 2019-01-04 2020-07-09 Total Marketing Services Utilisation de copolymères spécifiques pour abaisser la température limite de filtrabilité de carburants ou combustibles
FR3101882A1 (fr) 2019-10-14 2021-04-16 Total Marketing Services Utilisation de polymères cationiques particuliers comme additifs pour carburants et combustibles
WO2021105321A1 (fr) 2019-11-29 2021-06-03 Total Marketing Services Utilisation de diols comme additifs de détergence
WO2021105268A1 (fr) 2019-11-29 2021-06-03 Total Marketing Services Utilisation de composés alkyl phénol comme additifs de détergence pour essences
WO2022023636A1 (fr) 2020-07-31 2022-02-03 Totalenergies Marketing Services Utilisation de copolymères à distribution de masse molaire spécifique pour abaisser la température limite de filtrabilité de carburants ou de combustibles
FR3125298A1 (fr) 2021-07-19 2023-01-20 Totalenergies Marketing Services Utilisation d’une composition d’additifs pour réduire les émissions des véhicules Diesel

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FR2925916B1 (fr) * 2007-12-28 2010-11-12 Total France Terpolymere ethylene/acetate de vinyle/esters insatures comme additif ameliorant la tenue a froid des hydrocarbures liquides comme les distillats moyens et les carburants ou combustibles
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Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010073233A2 (fr) 2008-12-23 2010-07-01 Total Raffinage Marketing Carburant de type gazole pour moteur diesel a fortes teneurs en carbone d'origine renouvelable et en oxygene
WO2011001352A1 (fr) 2009-07-03 2011-01-06 Total Raffinage Marketing Terpolymere ethylene/acetate de vinyle/esters insatures comme additif ameliorant la tenue a froid des hydrocarbures liquides comme les distillats moyens et les carburants ou combustibles
WO2012085865A1 (fr) 2010-12-23 2012-06-28 Total Raffinage Marketing Résines alkylphénol-aldéhyde modifiées, leur utilisation comme additifs améliorant les propriétés a froid de carburants et combustibles hydrocarbonés liquides
WO2012107454A1 (fr) 2011-02-08 2012-08-16 Total Raffinage Marketing Compositions liquides pour marquer les carburants et combustibles hydrocarbones liquides, carburants et combustibles les contenant et procede de detection des marqueurs
WO2013120985A1 (fr) 2012-02-17 2013-08-22 Total Raffinage Marketing Additifs ameliorant la resistance a l'usure et au lacquering de carburants de type gazole ou biogazole
WO2013189868A1 (fr) 2012-06-19 2013-12-27 Total Marketing Services Compositions d'additifs et leur utilisation pour ameliorer les proprietes a froid de carburants et combustibles
WO2014029770A1 (fr) 2012-08-22 2014-02-27 Total Marketing Services Additifs ameliorant la resistance a l'usure et au lacquering de carburants de type gazole ou biogazole
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HUP9903777A3 (en) 2001-10-29
FR2753455B1 (fr) 1998-12-24
ES2170386T3 (es) 2002-08-01
JP3763584B2 (ja) 2006-04-05
KR100467280B1 (ko) 2005-01-24
BR9713201A (pt) 2000-04-04
MY116976A (en) 2004-04-30
DE69710913D1 (de) 2002-04-11
CA2266522A1 (fr) 1998-03-26
DK0938535T3 (da) 2002-06-24
CA2266522C (fr) 2005-07-26
HU223377B1 (hu) 2004-06-28
FR2753455A1 (fr) 1998-03-20
HUP9903777A2 (hu) 2000-04-28
EP0938535B1 (de) 2002-03-06
DE69710913T2 (de) 2002-10-31
JP2001503081A (ja) 2001-03-06
WO1998012283A1 (fr) 1998-03-26
ATE214085T1 (de) 2002-03-15
KR20000036209A (ko) 2000-06-26
US6083287A (en) 2000-07-04
RU2165448C2 (ru) 2001-04-20
PT938535E (pt) 2002-08-30

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