EP0722481B1 - Composition d'additifs d'operabilite a froid des distillats moyens - Google Patents

Composition d'additifs d'operabilite a froid des distillats moyens Download PDF

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Publication number
EP0722481B1
EP0722481B1 EP94928929A EP94928929A EP0722481B1 EP 0722481 B1 EP0722481 B1 EP 0722481B1 EP 94928929 A EP94928929 A EP 94928929A EP 94928929 A EP94928929 A EP 94928929A EP 0722481 B1 EP0722481 B1 EP 0722481B1
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.)
Expired - Lifetime
Application number
EP94928929A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0722481A1 (fr
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/fr
Application granted granted Critical
Publication of EP0722481B1 publication Critical patent/EP0722481B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • 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 composition of additives which improves the cold operability of middle distillates up to temperatures above -20 ° C, and more particularly for diesel fuels and domestic fuel.
  • This cold operability corresponds to a temperature limit 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 beginning of crystallization of paraffins in the distillate and the pour point of this last (AFNOR NFT60105) or ASTM D 97-66).
  • paraffins are crystallized at bottom of the tank, they can be driven at startup in the engine and clogging in particular filters and prefilters arranged before the combustion chamber. Likewise for the storage of domestic fuels, paraffins precipitate in bottom of tank and can be entrained and obstruct pipes leading to the boiler. It is obvious that 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 additives to lower and maintain the cold operability temperature of middle distillates, even after storage, up to temperatures above -20 ° C comprising in particular a third type additive having for action of maintaining a good dispersion of the crystals of paraffins in the middle distillate.
  • the polymer thus obtained comprises more than 20% by weight of alkyl chains comprising 12 and 14 atoms of carbon, and finally more than 10% by weight and preferably more of 20% by weight of alkyl chains comprising 16 atoms of carbon and more.
  • composition of the present invention improves cold operability of middle distillates since it allows achieve and maintain operating temperatures down to -20 ° C without circulation of the middle distillate influenced by solidification of paraffin crystals by agglomeration favoring blockages.
  • the new composition allows limit the sedimentation of paraffinic crystals and contributes to maintaining the dispersion of the crystals paraffin in middle distillates down to -20 ° C.
  • the polyamine chosen to prepare the anti-sedimentation additive corresponds to the following general formula (I) R-NH - [- (CH 2 ) n -NH-] m -H in which R is a saturated aliphatic radical comprising from 12 to 32 carbon atoms, n is an integer between 2 and 4 and m is an integer between 1 and 4.
  • the polyamine chosen to prepare the anti-sedimentation additive corresponds to the following general formula (II) in which R and R 'are identical or different linear alkyl radicals comprising from 1 to 24 carbon atoms, n is an integer between 2 and 4, and m is an integer between 1 and 4.
  • the dicarboxylic compound used to make the anti-sedimentation additive is preferably chosen from the group consisting of maleic, alkylmaleic anhydrides, in particular methylmaleic anhydride, and anhydrides alkenyl succinics obtained by the reaction of at least one olefin comprising from 10 to 32 carbon atoms with maleic anhydride.
  • Preferred as dicarboxylic compound are n-octadecenylsuccinic and dodecenylsuccinic anhydrides.
  • the dispersing-stabilizing additive is obtained from at least two reactions, one reaction esterification followed by a polymerization reaction.
  • Saturated linear alcohol participating in the reaction esterification for the formation of this additive is consisting of an alkyl chain comprising from 8 to 22 atoms of carbon.
  • the preferred organic acid involved in the reaction (A) esterification is acrylic acid.
  • the dispersing-stabilizing additive is therefore a polymer of general formula (III): in which R 1 and R 2 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, and q is an integer between 1 and 10.
  • R 1 and R 2 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) in which R 2 is a saturated aliphatic radical, comprising from 8 to 22 carbon atoms, and in which q is an integer between 1 and 50.
  • the additive dispersant-stabilizer is a copolymer.
  • Said copolymer is constituted for 90 to 99% by weight at least one alkylated acrylate comprising from 8 to 22 atoms of carbon and preferably 8 to 18 carbon atoms per chain alkylated, and from 10 to 1% by weight of at least one compound copolymerizer.
  • this said copolymer is constituted for 95 to 99% weight of at least one alkylated acrylate and for 1 to 5% weight of minus one copolymerizing compound.
  • Said copolymerizing compound is a compound dicarboxylic chosen from the group consisting of maleic, alkylmaleic and alkenylsuccinic anhydrides, and fumaric acid.
  • Preferred copolymerizing compounds are maleic anhydride and fumaric acid.
  • the new composition according to the present invention is advantageously made up, for 65 to 50% by weight of the combination of at least one anti-sedimentation additive and less a dispersant-stabilizing additive according to the invention and for 35 to 50% by weight of filterability additive.
  • the preferred filterability additive is chosen from the group made up of ethylene vinyl acetate (EVA) copolymers and ethylene vinyl propionate copolymers (EVP).
  • Another object of the invention is a composition of middle crude oil distillate comprising a proportion major of middle crude oil distillate and a proportion minor of said composition of additives first object of the invention.
  • said middle distillate is a hydrocarbon fraction distilled between 150 and 450 ° C, and preferably a distilled diesel cut between 190 and 350 ° C.
  • the minor proportion of said composition of prime additives object of the invention is between 0.01 and 0.20% by weight of said middle distillate composition.
  • This example aims to highlight the effect of unexpected synergy of the dispersing-stabilizing additive and the anti-sedimentation additive in the presence of a TLF type filterability.
  • test tubes are hermetically sealed, then left to stand in a cold room at (-20 ° C) for 24 hours. At after 24 hours, the homogeneity of the additive diesel is evaluated by the number of phases observed in each test tube and their quality, then we measure the point temperature of upper and lower phase disorder.
  • the quality of the upper phase is decisive at look at the anti-sedimentation efficiency of the composition additive.
  • the upper phase is cloudy, a large proportion of paraffins remained in suspension.
  • this phase is clear, almost all of the paraffins have sedimented, that is to say agglomerated in the bottom of the test tube.
  • the combination of the additive anti-sedimentation and dispersant-stabilizing additive with TLF additive greatly improves diesel homogeneity and limits the difference in trouble points between the phase upper and lower (samples 1, 2 and 4).
  • This example aims to show the universality of the combination of additives according to the invention with a view to lowering cold operability of middle distillates above -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 13 -C 18 ) and in paraffins comprising from 19 to 23 carbon atoms (C 19 -C 23 ) . This distribution is characteristic of the behavior of diesel fuel when cold, whatever its source.
  • compositions according to the invention promote cold operability at -20 ° C. characterized by obtaining two phases, one phase sedimented and a cloudy phase, and a temperature difference between the trouble points of the cloudy upper phase and of the sedimented lower phase between 0 and 10 in absolute value.

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  • 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)
  • Medicines Containing Plant Substances (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polyamides (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP94928929A 1993-09-30 1994-09-29 Composition d'additifs d'operabilite a froid des distillats moyens Expired - Lifetime EP0722481B1 (fr)

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 EP0722481A1 (fr) 1996-07-24
EP0722481B1 true EP0722481B1 (fr) 1998-06-10

Family

ID=9451420

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94928929A Expired - Lifetime EP0722481B1 (fr) 1993-09-30 1994-09-29 Composition d'additifs d'operabilite a froid des distillats moyens

Country Status (18)

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

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0744218B1 (de) * 1995-05-12 2003-01-22 Elpatronic Ag Verfahren und Vorrichtung zur Innenbeschichtung von Behälterzargen
WO1998021446A1 (en) * 1996-11-14 1998-05-22 Bp Exploration Operating Company Limited Inhibitors and their uses in oils
GB2334258B (en) * 1996-11-14 2001-05-16 Bp Exploration Operating 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
WO2017120287A1 (en) 2016-01-06 2017-07-13 Ecolab Usa Inc. Temperature-stable paraffin inhibitor compositions
US10759989B2 (en) 2016-01-06 2020-09-01 Ecolab Usa Inc. Temperature-stable paraffin inhibitor compositions
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

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4153423A (en) * 1975-03-28 1979-05-08 Exxon Research & Engineering Co. Polymer combinations useful in distillate hydrocarbon oils to improve cold flow properties
US4559155A (en) * 1982-08-09 1985-12-17 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4565550A (en) * 1982-08-09 1986-01-21 Dorer Jr Casper J 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
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
US4623684A (en) * 1982-08-09 1986-11-18 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
EP0153176B1 (en) * 1984-02-21 1991-11-27 Exxon Research And Engineering Company Middle distillate compositions with improved cold flow properties
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

Also Published As

Publication number Publication date
CZ293805B6 (cs) 2004-08-18
RU2128210C1 (ru) 1999-03-27
CZ91896A3 (en) 1996-10-16
DE69411027T2 (de) 1999-02-11
NO314089B1 (no) 2003-01-27
CN1044915C (zh) 1999-09-01
FI961425A0 (fi) 1996-03-29
UA48117C2 (uk) 2002-08-15
FI961425A (fi) 1996-03-29
HUT75503A (en) 1997-05-28
WO1995009220A1 (fr) 1995-04-06
KR100298237B1 (ko) 2001-10-24
NO961295L (no) 1996-03-29
CA2172985A1 (fr) 1995-04-06
FI119550B (fi) 2008-12-31
JPH09503015A (ja) 1997-03-25
DE69411027D1 (de) 1998-07-16
PL179141B1 (pl) 2000-07-31
CN1132523A (zh) 1996-10-02
HU9600829D0 (en) 1996-05-28
EP0722481A1 (fr) 1996-07-24
FR2710652B1 (fr) 1995-12-01
DK0722481T3 (da) 1999-03-22
KR960705004A (ko) 1996-10-09
US5725610A (en) 1998-03-10
FR2710652A1 (fr) 1995-04-07
NO961295D0 (no) 1996-03-29
HU220708B1 (hu) 2002-04-29
ATE167228T1 (de) 1998-06-15
PL313714A1 (en) 1996-07-22

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