EP0722481A1 - Zusätzezusammensetzung zur kalten verwendung der mitteldestillate - Google Patents

Zusätzezusammensetzung zur kalten verwendung der mitteldestillate

Info

Publication number
EP0722481A1
EP0722481A1 EP94928929A EP94928929A EP0722481A1 EP 0722481 A1 EP0722481 A1 EP 0722481A1 EP 94928929 A EP94928929 A EP 94928929A EP 94928929 A EP94928929 A EP 94928929A EP 0722481 A1 EP0722481 A1 EP 0722481A1
Authority
EP
European Patent Office
Prior art keywords
additive
weight
carbon atoms
composition according
integer
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
EP94928929A
Other languages
English (en)
French (fr)
Other versions
EP0722481B1 (de
Inventor
Despina Vassilakis
Robert Leger
Nathalie Cerqueda
Wolfgang Ritter
Thomas Reichert
Stephan Von Tapavicza
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 Personal Care and Nutrition GmbH
Elf Antar France
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA, Elf Antar France filed Critical Henkel AG and Co KGaA
Publication of EP0722481A1 publication Critical patent/EP0722481A1/de
Application granted granted Critical
Publication of EP0722481B1 publication Critical patent/EP0722481B1/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
    • 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
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1966—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof poly-carboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—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

Definitions

  • the present invention relates to a new additive composition which improves the cold operability of middle distillates up to temperatures above -20 ° C., and more particularly for diesel fuels and household fuels.
  • This cold operability corresponds to a limit temperature at which middle distillates can be used without clogging problem. It is intermediate between the cloud point temperature (AFNOR NFT 60105 or ASTM D 2500-66) characteristic of the start of paraffin crystallization in the distillate and the pour point of the latter (AFNOR NFT60105) or ASTM D 97-66 ).
  • paraffins are crystallized at the bottom of the tank, they can be entrained at start-up in the engine and in particular clog the filters and prefilters placed before the combustion chamber. Similarly for the storage of domestic fuels, paraffins precipitate at the bottom of the tank and can be entrained and obstruct the pipes leading to the boiler. It is obvious that the the presence of solids, such as paraffin crystals, prevents normal circulation of the middle distillate.
  • TLF additives Filterability Limit Temperature
  • the present invention relates to a new composition of additives for lowering and maintaining the cold operability temperature of middle distillates, even after storage, up to temperatures above -20 ° C. comprising in particular an additive of the third type having the action of maintaining good dispersion of the paraffin crystals in the middle distillate.
  • the subject of the present invention is therefore a composition of additives for lowering the cold operability temperature of the distillates beyond -20 ° C. characterized in that it comprises at least 40% by weight of a combination consisting of : (i) 60% -94% by weight of an anti-sedimentation additive of average molecular weight of about 300 to 10,000 resulting from the reaction
  • R is a saturated aliphatic radical comprising from 1 to 32 carbon atoms
  • R ' is chosen from the group consisting of the hydrogen atom and saturated aliphatic radicals comprising from 1 to 32 carbon atoms
  • n is an integer between 2 and 4
  • m is an integer between 1 and 4
  • said reaction occurring after dilution of said dicarboxylic compound and said polyamine in a hydrocarbon solvent with a boiling point between 70 ° C and 250 ° C for a ratio of the molar concentrations of said polyamine to said dicarboxylic compound of between 0.3 and 0.8 and at a temperature between 120 and 200 ° C, for 1 to 8 hours.
  • the polymer thus obtained comprises more than 20% by weight of alkyl chains comprising 12 and 14 carbon atoms, and finally more than 10% by weight and preferably more than 20% by weight of alkyl chains comprising 16 carbon atoms and more.
  • the composition of the present invention improves
  • the new composition makes it possible to limit the sedimentation of paraffinic crystals and contributes to maintaining the dispersion of paraffin crystals in middle distillates down to -20 ° C.
  • dar-s la - R island is a saturated aliphatic radical comprising from 12 to 32 carbon atoms, n is an integer between 2 and 4 ⁇ t m is an integer between 1 and 4.
  • the polyamine chosen to prepare the anti-sedimentation additive corresponds to the general formula followed by ⁇ e (II)
  • the dicarboxylic compound used to manufacture the anti-food additive is preferably chosen from the group consisting of maleic, alkylmaleic anhydrides, in particular methylmaleic anhydride, and alkenylsuccinic anhydrides obtained by the reaction of at least one olefin comprising from 10 to 32 carbon atoms with maleic anhydride.
  • the dispersant-stabilizing additive is obtained from at least two reactions, an esterification reaction followed by a polymerization reaction.
  • the saturated linear alcohol participating in the esterification reaction for the formation of this additive consists of an alkyl chain comprising from 8 to 22 carbon atoms.
  • the dispersing-stabilizing additive has an ⁇ ⁇ r of general formula (III): R 1 - (- (CT 2 ) p- ⁇ -) q- R 3 d ")
  • R-- and R are identical or different and correspond to the hydrogen atom or a saturated aliphatic radical comprising from 1 to 30 carbon atoms
  • R 3 corresponds to a hydrogen atom or a dicarboxylic compound chosen from the group consisting of maleic, alkylmaleic or alkenylsuccinic anhydrides, acrylic acid and fumaric acid
  • p is an integer between 1 and 100
  • q is an integer between 1 and 10.
  • the dispersing-stabilizing additive is a polyacrylate of general formula (IV)
  • the dispersant-stabilizing additive is a copolymer .
  • Said copolymer consists for 90 to 99% by weight of at least one alkylated acrylate comprising from 8 to 22 carbon atoms and preferably 8 to 18 carbon atoms per alkylated chain, and from 10 to 1% by weight of at least one copolymerizing compound.
  • said copolymer consists for 95 to 99% by weight of at least one alkylated acrylate and for 1 to 5% by weight of at least one copolymerizing compound.
  • Said copolymerizing compound is a dicarboxylic compound chosen from the group consisting of maleic, alkylmaleic and alkenylsuccinic anhydrides, and fumaric acid. The preferred copolymerizing compounds are random anhydride and fumaric acid.
  • the new composition according to the present invention advantageously comprises a filterability additive.
  • a filterability additive consists for 40 to 70% by weight of the combination of at least one anti-sedimentation additive and at least one dispersant-stabilizing additive according to the invention and for 30 to 60% by weight of at least one filterability additive.
  • it comprises from 65 to 50% by weight of said combination and from 35 to 50% by weight of the filterability additive.
  • the preferred filterability additive is chosen from the group consisting of ethylene-vinyl acetate (EVA) copolymers and ethylene-vinyl propionate (EVP) copolymers.
  • Another subject of the invention is a composition of medium crude oil distillate comprising a major proportion of medium crude oil distillate and a minor proportion of said composition of additives first object of
  • said middle distillate is a hydrocarbon fraction distilled between 150 and 450 ° C, and preferably a diesel fraction distilled between 190 and 350 ° C.
  • the minor proportion of said composition of additives which is the first object of the invention is between 0.01 and 0.20% by weight of said middle distillate composition.
  • EXAMPLE 1 The present example aims to emphasize the unexpected synergistic effect of the dispersant-stabilizing additive and the anti-sedimentation additive in the presence of a filterability additive type TLF. To this end, samples of diesel were prepared from a diesel as defined below and in Table I.
  • test tubes are sealed hermetically, then left to stand in a cold room at (-20 ° C) for 24 hours. After 24 hours, the homogeneity of the diesel fuel additive is evaluated by the number of phases observed in each test tube and their quality, then the cloud point temperature of the upper and lower phases is measured.
  • the quality of the upper phase is decisive with regard to the anti-sedimentation efficiency of the additive composition.
  • the upper phase is cloudy, a large proportion of paraffins have remained in suspension.
  • this phase is clear, almost all paraffins sedimented, that is to say has agglomerated in the bottom of • 1 specimen.
  • the combination of the anti-sedimentation additive and the dispersing-stabilizing additive with the TLF additive greatly improves the homogeneity of the diesel fuel and limits the difference in cloud points between the upper and lower phases (samples 1, 2 and 4).
  • the present example aims to show the universality of the combination of additives according to the invention with a view to lowering the cold operability of middle distillates beyond -20 ° C., whatever their origin.
  • Example I For the purposes of this example, three gas oils A, B and C additivated by combinations according to the invention are tested as described in Example I. These are characterized by their paraffinic distribution, that is to say by their concentration in paraffins comprising less than 13 carbon atoms ( ⁇ C 13 ), in paraffins comprising from 13 to 18 carbon atoms (C ⁇ 3 -C ⁇ 8 ) and in paraffins comprising from 19 to 23 carbon atoms (C-
  • compositions according to the invention promote cold operability at -20 ° C., characterized by obtaining two phases, a sedimented phase and a cloudy phase, and a difference temperature between the trouble points of the cloudy upper phase and the sedimented lower phase between 0 and 10 in absolute value.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Lubricants (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Fats And Perfumes (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Cosmetics (AREA)
  • Polyamides (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP94928929A 1993-09-30 1994-09-29 Additivzusammensetzung zur verbesserung der kältefliess- eigenschaften von mitteldestillate Expired - Lifetime EP0722481B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9311664A FR2710652B1 (fr) 1993-09-30 1993-09-30 Composition d'additifs d'opérabilité à froid des distillats moyens.
FR9311664 1993-09-30
PCT/FR1994/001138 WO1995009220A1 (fr) 1993-09-30 1994-09-29 Composition d'additifs d'operabilite a froid des distillats moyens

Publications (2)

Publication Number Publication Date
EP0722481A1 true EP0722481A1 (de) 1996-07-24
EP0722481B1 EP0722481B1 (de) 1998-06-10

Family

ID=9451420

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94928929A Expired - Lifetime EP0722481B1 (de) 1993-09-30 1994-09-29 Additivzusammensetzung zur verbesserung der kältefliess- eigenschaften von mitteldestillate

Country Status (18)

Country Link
US (1) US5725610A (de)
EP (1) EP0722481B1 (de)
JP (1) JPH09503015A (de)
KR (1) KR100298237B1 (de)
CN (1) CN1044915C (de)
AT (1) ATE167228T1 (de)
CA (1) CA2172985A1 (de)
CZ (1) CZ293805B6 (de)
DE (1) DE69411027T2 (de)
DK (1) DK0722481T3 (de)
FI (1) FI119550B (de)
FR (1) FR2710652B1 (de)
HU (1) HU220708B1 (de)
NO (1) NO314089B1 (de)
PL (1) PL179141B1 (de)
RU (1) RU2128210C1 (de)
UA (1) UA48117C2 (de)
WO (1) WO1995009220A1 (de)

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DE59610063D1 (de) * 1995-05-12 2003-02-27 Elpatronic Ag Bergdietikon Verfahren und Vorrichtung zur Innenbeschichtung von Behälterzargen
GB2334258B (en) * 1996-11-14 2001-05-16 Bp Exploration Operating Inhibitors and their uses in oils
AU4877897A (en) * 1996-11-14 1998-06-03 Bp Exploration Operating Company Limited Inhibitors and their uses in oils
US6017370A (en) * 1998-09-25 2000-01-25 The Lubrizol Corporation Fumarate copolymers and acylated alkanolamines as low temperature flow improvers
FR2792646B1 (fr) * 1999-04-26 2001-07-27 Elf Antar France Composition d'additifs multifonctionnels d'operabilite a froid des distillats moyens
FR2888248B1 (fr) * 2005-07-05 2010-02-12 Total France Composition lubrifiante pour melange hydrocarbone et produits obtenus
US20150232774A1 (en) * 2014-02-19 2015-08-20 Afton Chemical Corporation Fuel additive for diesel engines
RU2734848C2 (ru) * 2016-01-06 2020-10-23 ЭКОЛАБ ЮЭсЭй ИНК. Термостабильные композиции ингибиторов осаждения парафина
RU2736835C2 (ru) 2016-01-06 2020-11-20 ЭКОЛАБ ЮЭсЭй ИНК. Термостабильные композиции ингибиторов парафинообразования
RU2647858C1 (ru) * 2017-03-03 2018-03-21 Публичное акционерное общество "Нефтяная компания "Роснефть" (ПАО "НК "Роснефть") Способ получения диспергирующей присадки к дизельному топливу и диспергирующая присадка к дизельному топливу
US10858575B2 (en) 2017-06-02 2020-12-08 Championx Usa Inc. Temperature-stable corrosion inhibitor compositions and methods of use

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US4153423A (en) * 1975-03-28 1979-05-08 Exxon Research & Engineering Co. Polymer combinations useful in distillate hydrocarbon oils to improve cold flow properties
US4565550A (en) * 1982-08-09 1986-01-21 Dorer Jr Casper J Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4613342A (en) * 1982-08-09 1986-09-23 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4575526A (en) * 1982-08-09 1986-03-11 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same
US4559155A (en) * 1982-08-09 1985-12-17 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4623684A (en) * 1982-08-09 1986-11-18 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4564460A (en) * 1982-08-09 1986-01-14 The Lubrizol Corporation Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
DE3584729D1 (de) * 1984-02-21 1992-01-09 Exxon Research Engineering Co Mitteldestillat-zusammensetzungen mit fliesseigenschaften bei kaelte.
DE3807394A1 (de) * 1988-03-07 1989-09-21 Henkel Kgaa Verwendung ausgewaehlter copolymertypen der acryl- und/oder methacrylsaeureester als fliessverbesserer in paraffinreichen erdoelen und erdoelfraktionen (i)
FR2633638B1 (fr) * 1988-06-29 1991-04-19 Inst Francais Du Petrole Formulations d'additifs azotes pour carburants moteurs et les carburants moteurs les contenant
DE4036227A1 (de) * 1990-11-14 1992-05-21 Basf Ag Erdoelmitteldestillate mit verbesserten fliesseigenschaften in der kaelte

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Also Published As

Publication number Publication date
HU9600829D0 (en) 1996-05-28
CZ293805B6 (cs) 2004-08-18
JPH09503015A (ja) 1997-03-25
KR100298237B1 (ko) 2001-10-24
FR2710652A1 (fr) 1995-04-07
CN1044915C (zh) 1999-09-01
KR960705004A (ko) 1996-10-09
DK0722481T3 (da) 1999-03-22
WO1995009220A1 (fr) 1995-04-06
US5725610A (en) 1998-03-10
FR2710652B1 (fr) 1995-12-01
NO961295L (no) 1996-03-29
DE69411027T2 (de) 1999-02-11
FI961425A0 (fi) 1996-03-29
UA48117C2 (uk) 2002-08-15
CZ91896A3 (en) 1996-10-16
NO961295D0 (no) 1996-03-29
EP0722481B1 (de) 1998-06-10
PL313714A1 (en) 1996-07-22
DE69411027D1 (de) 1998-07-16
FI961425A (fi) 1996-03-29
PL179141B1 (pl) 2000-07-31
FI119550B (fi) 2008-12-31
NO314089B1 (no) 2003-01-27
CN1132523A (zh) 1996-10-02
HU220708B1 (hu) 2002-04-29
RU2128210C1 (ru) 1999-03-27
HUT75503A (en) 1997-05-28
CA2172985A1 (fr) 1995-04-06
ATE167228T1 (de) 1998-06-15

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