US20060196110A1 - Fuel composition - Google Patents

Fuel composition Download PDF

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Publication number
US20060196110A1
US20060196110A1 US10/551,239 US55123905A US2006196110A1 US 20060196110 A1 US20060196110 A1 US 20060196110A1 US 55123905 A US55123905 A US 55123905A US 2006196110 A1 US2006196110 A1 US 2006196110A1
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US
United States
Prior art keywords
fuel
additive
gasoline
gasoline fuel
composition according
Prior art date
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Abandoned
Application number
US10/551,239
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English (en)
Inventor
Harald Schwahn
Dietmar Posselt
Erich Fehr
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BASF SE
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BASF SE
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Publication date
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Application filed by BASF SE filed Critical BASF SE
Assigned to BASF AKTIENGESELLSCHAFT reassignment BASF AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FEHR, ERICH K., POSSELT, DIETMAR, SCHWAHN, HARALD
Publication of US20060196110A1 publication Critical patent/US20060196110A1/en
Assigned to BASF SE reassignment BASF SE CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: BASF AKTIENGESELLSCHAFT
Abandoned 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
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • 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
    • 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
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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)

Definitions

  • the present invention relates to a fuel composition
  • a fuel composition comprising a major amount of a specific lower alkanol-containing gasoline fuel and a minor amount of selected gasoline fuel additives.
  • Carburetors and intake systems of gasoline engines, and also injection systems for fuel metering, are contaminated to an increasing degree by impurities which are caused by dust particles from the air, uncombusted hydrocarbon residues from the combustion chamber and the crankcase vent gases conducted into the carburetor.
  • valve seat wear-inhibiting additives have been developed which are based on alkali metal or alkaline earth metal compounds.
  • gasoline fuels For trouble-free use, modern gasoline engines require fuels having a complex profile of properties which.can only be ensured in combination with appropriate gasoline fuel additives.
  • Such gasoline fuels generally consist of a complex mixture of chemical compounds and are character;zed by physical quantities.
  • the interplay between gasoline fuels and appropriate additives is still in need of improvement in the known fuel compositions with regard to the action of cleaning and keeping clean, and the valve seat wear-inhibiting action.
  • the intention is to find more effective additive formulations.
  • a fuel composition which comprises a major amount of a gasoline fuel having a maximum sulfur content of 150 ppm by weight and a minor amount of at least one gasoline fuel additive having detergent action or having a valve seat wear-inhibiting action, wherein this gasoline fuel additive has at least one hydrophobic hydrocarbon radical having a number-average molecular weight (MN) of from 85 to 20,000 and at least one polar moiety, and wherein the fuel composition also has a content of at least one lower alkanol of from about 5 to 75% by volume.
  • MN number-average molecular weight
  • the polar moiety is selected from:
  • the alkanol used in accordance with the invention is preferably a straight-chain or branched, saturated C 1 -C 6 -mono- or -diol, in particular a C 1 -C 3 -mono alkanol, such as methanol, ethanol, n- or i-propanol, or a mixture of a plurality of these alkanols.
  • the alkanol content is a maximum of 75% by volume, for example from 5 to 75% by volume, preferably from 10 to 65% by volume, in particular from 20 to 55% by volume, for example 30 - 40% by volume or 40-50% by volume.
  • the content of further alcohols and ethers in the gasoline fuel is normally relatively low.
  • Typical maximum contents are 7% by volume for tert-butanol, 10% by volume for isobutanol and 15% by volume for ethers having 5 or more carbon atoms in the molecule.
  • the maximum aromatics content of the gasoline fuel is preferably 40% by volume, in particular 38% by volume.
  • Preferred ranges for the aromatics content are from 20 to 42% by volume, in particular from 25 to 40% by volume.
  • the maximum sulfur content of the gasoline fuel is preferably 100 ppm by weight, in particular 50 ppm by weight.
  • Preferred ranges for the sulfur content are from 0.5 to 150 ppm by weight, in particular from 1 to 100 ppm by weight.
  • the gasoline fuel has a maximum olefin content of 21 % by volume, preferably 18% by volume, in particular 10% by volume.
  • Preferred ranges for the olefin content are from 6 to 21 % by volume, in particular from 7 to 18% by volume.
  • the gasoline fuel has a maximum benzene content of 1.0% by volume, in particular 0.9% by volume
  • Preferred ranges for the benzene 25 content are from 0.5 to 1.0% by volume, in particular from 0.6 to 0.9% by volume.
  • the oxygen content of the gasoline fuel is a maximum of 2.7% by weight, and is preferably from 0.1 to 2.7% by weight, in particular from 1.0 to 2.7% by weight, especially from 1.2 to 2.0% by weight.
  • a gasoline fuel which at the same time has a maximum aromatics content of 38% by volume, a maximum olefin content of 21% by volume, a maximum sulfur content of 50 ppm by weight, a maximum benzene content of 1.0% by volume and an oxygen content of from 1.0 to 2.7% by weight.
  • the summer vapor pressure of the gasoline fuel is typically a maximum of 70 kPa, in particular 60 kPa (each at 370 C).
  • the research octane number (“RON”) of the gasoline fuel is generally from 90 to 100.
  • a typical range for the corresponding motor octane number (“MON”) is from 80 to 90.
  • the hydrophobic hydrocarbon radical in the gasoline fuel additives which ensures sufficient solubility in the fuel, has a number-average molecular weight (Mn) of from 85 to 20,000, especially from 113 to 10,000, in particular from 300 to 5,000.
  • Such additives based on highly reactive polyisobutene which can be prepared from the polyisobutene which may comprise up to 20% by weight of n-butene units by hydroformylation and reductive amination with ammonia, monoamines or polyamines, such as dimethylaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine, are disclosed in particular in EP-A 244 616.
  • additives comprising monoamino groups (a) are the compounds obtainable from polyisobutene epoxides by reaction with amines and subsequent dehydration and reduction of the amino alcohols, as described in particular in DE-A 196 20 262.
  • These reaction products are generally mixtures of pure nitropoly-isobutanes (e.g. alpha, beta-dinitropolyisobutane) and mixed hydroxynitropoly-isobutanes (e.g. alpha-nitro-beta-hydroxypolyisobutane).
  • Additives comprising hydroxyl groups in combination with mono- or polyamino groups are in particular reaction products of polyisobutene epoxides obtainable from polyisobutene having preferably predominantly terminal double bonds and Mn from 300 to 5 000, with ammonia or mono- or polyamines, as described in particular in EP-A 476 485.
  • Additives comprising carboxyl groups or their alkali metal or alkaline earth metal salts (d) are preferably copolymers of C 2 -C 40 -olefins with maleic anhydride which have a total molar mass of from 500 to 20 000 and of whose carboxyl groups some or all have been converted to the alkali metal or alkaline earth metal salts and any remainder of the carboxyl groups has been reacted with alcohols or amines.
  • Such additives are disclosed in particular by EP-A 307 815.
  • Such additives serve mainly to prevent valve seat wear and can, as described in WO-A 87/01126, advantageously be used in combination with customary fuel detergents such as poly(iso)butenamines or polyetheramines.
  • Additives comprising sulfonic acid groups or their alkali metal or alkaline earth metal salts are preferably alkali metal or alkaline earth metal salts of an alkyl sulfosuccinate, as described in particular in EP-A 639 632.
  • Such additives serve mainly to prevent valve seat wear and can be used advantageously in combination with customary fuel detergents such as poly(iso)butenamines or polyetheramines.
  • Additives comprising polyoxy-C 2 - to C 4 -alkylene moieties are preferably polyethers or polyetheramines which are obtainable by reaction of C 2 - to C 60 -alkanols, C 6 - to C 30 -alkanediols, mono- or di-C 2 -C 30 -alkylamines, C 1 -C 30 -alkylcyclohexanols or C 1 -C 30 -alkylphenols with from 1 to 30 mol of 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.
  • 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.
  • polyethers such products also have carrier oil properties. Typical examples of these are tridecanol butoxylates, isotridecanol butoxylates, isononylphenol butoxylates and polyisobutenol butoxylates and propoxylates and also the corresponding reaction products with ammonia.
  • Additives comprising carboxylic ester groups (g) 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 /s at 100° C., as described in particular in DE-A 38 38 918.
  • the mono-, di- or tricarboxylic acids used may be aliphatic or aromatic acids, and particularly suitable ester alcohols or ester polyols are long-chain representatives having, for example, from 6 to 24 carbon atoms.
  • esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, of isononanol, of isodecanol and of isotridecanol.
  • Such products also have carrier oil properties.
  • Particular interest attaches to derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine.
  • Such gasoline fuel additives are described in particular in US-A 4 849 572.
  • Additives comprising moieties obtained by Mannich reaction of substituted phenols with aldehydes and mono- or polyamines are preferably reaction products of polyisobutene-substituted phenols with formaldehyde and mono- or polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine or dimethylaminopropylamine,
  • Such “polyisobutene-Mannich bases” are described in particular in EP-A 831 141.
  • the fuel composition according to the invention may additionally comprise further customary components and additives.
  • Useful solvents or diluents are aliphatic and aromatic hydrocarbons such as Solvent Naphtha.
  • corrosion inhibitors for example based on ammonium salts of organic carboxylic acids, said salts tending to form films, or of heterocyclic aromatics for nonferrous metal corrosion protection, antioxidants or stabilizers, for example based on amines such as p-phenylenediamine, dicyclohexylamine or derivatives thereof or of phenols such as 2,4-di-tert-butylphenol or 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid, demulsifiers, antistats, metallocenes such as ferrocene or methylcyclopentadienylmanganese tricarbonyl, lubricity additives such as certain fatty acids, alkenylsuccinic esters, bis(hydroxyalkyl) fatty amines, hydroxyacetamides or castor oil and also markers. Amines are also optionally added to lower the pH of the fuel.
  • gasoline fuel additives having the polar moiety (f) and corrosion inhibitors and/or lubricity additives based on carboxylic acids or fatty acids which may be present as monomeric and/or dimeric species.
  • Typical mixtures of this type comprise polyisobutanamines in combination with alkanol-started polyethers such as tridecanol or isotridecanol butoxylates or propoxylates, polyisobutenamines in combination with alkanol-started polyetheramines such as tridecanol or isotridecanol butoxylate-ammonia reaction products and alkanol-started polyetheramines such as tridecanol or isotridecanol butoxylate reaction products in combination with alkanol-started polyethers such as tridecanol or isotridecanol butoxylates or propoxylates, used together with the corrosion inhibitors and/or lubricity additives mentioned.
  • alkanol-started polyethers such as tridecanol or isotridecanol butoxylates or propoxylates
  • alkanol-started polyethers such as tridecanol or isotridecanol butoxylates or
  • the gasoline fuel additives having the polar moieties (a) to (i) mentioned, and also the other components mentioned, are metered into the gasoline fuel and exhibit their action there.
  • the components and/or additives may be added to the fuel individually or as a concentrate prepared beforehand (“additive package”).
  • the gasoline fuel additives having the polar moieties (a) to (i) mentioned are added to the gasoline fuel typically in an amount of from 1 to 5000 ppm by weight, especially from 5 to 3000 ppm by weight, in particular from 10 to 1000 ppm by weight.
  • the other components and additives mentioned are, if desired, added in amounts customary for this purpose.
  • the fuel composition according to the invention additionally exhibits advantages to the effect that fewer deposits are formed in the combustion chamber of the gasoline engine and that less additive is entrained into the engine oil via the fuel dilution.
  • the invention further relates to
  • valve seat wear-inhibitor for gasoline fuels.
  • Example 1 was repeated except that GF 2 was used instead of GF 1.
  • Example 1 was repeated except that GF 3 was used instead of GF 1
  • TCD total combustion deposits

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  • 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)
  • Detergent Compositions (AREA)
US10/551,239 2003-04-11 2004-04-08 Fuel composition Abandoned US20060196110A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10316871A DE10316871A1 (de) 2003-04-11 2003-04-11 Kraftstoffzusammensetzung
DE10316871.0 2003-04-11
PCT/EP2004/003811 WO2004090079A1 (de) 2003-04-11 2004-04-08 Kraftstoffzusammensetzung

Publications (1)

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US20060196110A1 true US20060196110A1 (en) 2006-09-07

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US10/551,239 Abandoned US20060196110A1 (en) 2003-04-11 2004-04-08 Fuel composition

Country Status (22)

Country Link
US (1) US20060196110A1 (ko)
EP (3) EP1615985B1 (ko)
JP (3) JP4452712B2 (ko)
KR (2) KR101320732B1 (ko)
CN (1) CN100545244C (ko)
AR (1) AR044001A1 (ko)
AU (1) AU2004227095B2 (ko)
BR (1) BRPI0409171A (ko)
CA (2) CA2520578C (ko)
CL (1) CL2004000766A1 (ko)
DE (1) DE10316871A1 (ko)
DK (1) DK1615985T3 (ko)
ES (1) ES2443993T3 (ko)
MX (1) MXPA05010183A (ko)
MY (1) MY162483A (ko)
NO (1) NO20054374L (ko)
PL (2) PL2270119T3 (ko)
PT (1) PT1615985E (ko)
RU (1) RU2005134823A (ko)
SI (1) SI1615985T1 (ko)
WO (1) WO2004090079A1 (ko)
ZA (1) ZA200509086B (ko)

Cited By (16)

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US20080086934A1 (en) * 2006-10-16 2008-04-17 Cunningham Lawrence J Protecting fuel delivery systems in engines combusting ethanol-containing fuels
US20080086933A1 (en) * 2006-10-16 2008-04-17 Cunningham Lawrence J Volatility agents as fuel additives for ethanol-containing fuels
US20080086935A1 (en) * 2006-10-16 2008-04-17 Lawrence J Cunningham Method and compositions for reducing corrosion in engines combusting ethanol-containing fuels
US20080086936A1 (en) * 2006-10-16 2008-04-17 Cunningham Lawrence J Method and compositions for reducing wear in engines combusting ethanol-containing fuels
US20080168708A1 (en) * 2007-01-11 2008-07-17 Cunningham Lawrence J Method and compositions for reducing deposits in engines combusting ethanol-containing fuels and a corrosion inhibitor
US9249769B1 (en) 2015-03-24 2016-02-02 Afton Chemical Corporation Fuel additives for treating internal deposits of fuel injectors
US10273425B2 (en) 2017-03-13 2019-04-30 Afton Chemical Corporation Polyol carrier fluids and fuel compositions including polyol carrier fluids
US10377958B2 (en) 2014-01-29 2019-08-13 Basf Se Corrosion inhibitors for fuels and lubricants
US10457884B2 (en) 2013-11-18 2019-10-29 Afton Chemical Corporation Mixed detergent composition for intake valve deposit control
US11078418B2 (en) 2016-07-05 2021-08-03 Basf Se Corrosion inhibitors for fuels and lubricants
US11130923B2 (en) * 2017-04-11 2021-09-28 Basf Se Alkoxylated amines as fuel additives
GB2609091A (en) * 2021-07-16 2023-01-25 Innospec Ltd Compositions, and methods and uses relating thereto
US11795412B1 (en) 2023-03-03 2023-10-24 Afton Chemical Corporation Lubricating composition for industrial gear fluids
US11873461B1 (en) 2022-09-22 2024-01-16 Afton Chemical Corporation Extreme pressure additives with improved copper corrosion
US11884890B1 (en) 2023-02-07 2024-01-30 Afton Chemical Corporation Gasoline additive composition for improved engine performance
US12024686B2 (en) 2022-09-30 2024-07-02 Afton Chemical Corporation Gasoline additive composition for improved engine performance

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DE10316871A1 (de) 2003-04-11 2004-10-21 Basf Ag Kraftstoffzusammensetzung
JP2011511859A (ja) 2008-02-01 2011-04-14 ビーエーエスエフ ソシエタス・ヨーロピア 特殊なポリイソブテンアミンおよび燃料中の洗剤としての該化合物の使用
GB0903165D0 (en) * 2009-02-25 2009-04-08 Innospec Ltd Methods and uses relating to fuel compositions
KR20130095660A (ko) * 2010-06-01 2013-08-28 바스프 에스이 분산제 부스터로서 저분자량의 폴리이소부틸-치환된 아민
JP2014501813A (ja) 2010-12-02 2014-01-23 ビーエーエスエフ ソシエタス・ヨーロピア ヒドロカルビルで置換されたジカルボン酸と窒素化合物とからの反応生成物の、燃料消費量の低減のための使用
EP2554636A1 (en) * 2011-08-03 2013-02-06 Innospec Limited Fuel compositions
US20150113867A1 (en) 2013-10-24 2015-04-30 Basf Se Use of an alkoxylated polytetrahydrofuran to reduce fuel consumption
US20150113864A1 (en) 2013-10-24 2015-04-30 Basf Se Use of a complex ester to reduce fuel consumption
US20150113859A1 (en) 2013-10-24 2015-04-30 Basf Se Use of polyalkylene glycol to reduce fuel consumption
MY180330A (en) * 2014-01-29 2020-11-28 Basf Se Use of polycarboxylic-acid-based additives for fuels
RU2019122807A (ru) 2016-12-20 2021-01-22 Басф Се Применение смеси комплексного сложного эфира с монокарбоновой кислотой для уменьшения трения
KR20210127323A (ko) 2020-04-14 2021-10-22 정재훈 애완견 배변기

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RU2005134823A (ru) 2006-06-10
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KR20060006781A (ko) 2006-01-19
PL2270119T3 (pl) 2021-01-25
ZA200509086B (en) 2007-02-28
KR101186408B1 (ko) 2012-09-27
AU2004227095B2 (en) 2010-07-15
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KR20120081230A (ko) 2012-07-18
AR044001A1 (es) 2005-08-24
AU2004227095A1 (en) 2004-10-21
CN100545244C (zh) 2009-09-30
PL1615985T3 (pl) 2014-05-30
CA2810284A1 (en) 2004-10-21
EP2270119B1 (de) 2020-07-15
WO2004090079A1 (de) 2004-10-21
EP2270119A1 (de) 2011-01-05
SI1615985T1 (sl) 2014-02-28
MY162483A (en) 2017-06-15
CN1802425A (zh) 2006-07-12
JP2013209664A (ja) 2013-10-10
CA2520578C (en) 2013-06-18
CA2520578A1 (en) 2004-10-21
MXPA05010183A (es) 2005-11-08
EP1615985B1 (de) 2013-12-11
JP4452712B2 (ja) 2010-04-21
CL2004000766A1 (es) 2005-02-04
PT1615985E (pt) 2014-01-29
DK1615985T3 (en) 2014-03-03
NO20054374L (no) 2005-09-29
EP1615985A1 (de) 2006-01-18
JP2010013665A (ja) 2010-01-21
EP3736317A1 (de) 2020-11-11
ES2443993T3 (es) 2014-02-21
CA2810284C (en) 2015-06-16
KR101320732B1 (ko) 2013-10-21

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