DE69000288T2 - Verfahren zur herstellung von dielektrischen fluessigkeiten. - Google Patents
Verfahren zur herstellung von dielektrischen fluessigkeiten.Info
- Publication number
- DE69000288T2 DE69000288T2 DE9090402722T DE69000288T DE69000288T2 DE 69000288 T2 DE69000288 T2 DE 69000288T2 DE 9090402722 T DE9090402722 T DE 9090402722T DE 69000288 T DE69000288 T DE 69000288T DE 69000288 T2 DE69000288 T2 DE 69000288T2
- Authority
- DE
- Germany
- Prior art keywords
- aromatic
- chloride
- products
- condensation
- toluene
- 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 - Fee Related
Links
- 239000007788 liquid Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- -1 aromatic halides Chemical class 0.000 claims abstract description 14
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 13
- 238000009833 condensation Methods 0.000 claims abstract description 13
- 230000005494 condensation Effects 0.000 claims abstract description 13
- 238000005406 washing Methods 0.000 claims abstract description 13
- 239000012530 fluid Substances 0.000 claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 7
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 61
- 239000000047 product Substances 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 18
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical group ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 13
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 claims description 12
- 229940073608 benzyl chloride Drugs 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 10
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims description 8
- 239000007859 condensation product Substances 0.000 claims description 6
- 230000003750 conditioning effect Effects 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract description 7
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract description 7
- 239000007864 aqueous solution Substances 0.000 abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000001577 simple distillation Methods 0.000 description 4
- PKQYSCBUFZOAPE-UHFFFAOYSA-N 1,2-dibenzyl-3-methylbenzene Chemical compound C=1C=CC=CC=1CC=1C(C)=CC=CC=1CC1=CC=CC=C1 PKQYSCBUFZOAPE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 2
- PQTAUFTUHHRKSS-UHFFFAOYSA-N 1-benzyl-2-methylbenzene Chemical compound CC1=CC=CC=C1CC1=CC=CC=C1 PQTAUFTUHHRKSS-UHFFFAOYSA-N 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000003613 toluenes Chemical class 0.000 description 2
- IOXAUPNPMJKSKQ-UHFFFAOYSA-N 1-benzyl-2,3-dimethylbenzene Chemical group CC1=CC=CC(CC=2C=CC=CC=2)=C1C IOXAUPNPMJKSKQ-UHFFFAOYSA-N 0.000 description 1
- GTLWADFFABIGAE-UHFFFAOYSA-N 1-chloroethylbenzene Chemical compound CC(Cl)C1=CC=CC=C1 GTLWADFFABIGAE-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical group C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/20—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils
- H01B3/22—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/02—Well-defined hydrocarbons
- C10M105/06—Well-defined hydrocarbons aromatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
- C10M105/52—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen and halogen only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/16—Dielectric; Insulating oil or insulators
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/17—Electric or magnetic purposes for electric contacts
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Insulating Materials (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Inorganic Insulating Materials (AREA)
- Lubricants (AREA)
- Compounds Of Iron (AREA)
- Oxygen, Ozone, And Oxides In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8913451A FR2653134B1 (fr) | 1989-10-13 | 1989-10-13 | Procede de synthese de fluides dielectriques. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69000288D1 DE69000288D1 (de) | 1992-10-08 |
| DE69000288T2 true DE69000288T2 (de) | 1993-03-18 |
Family
ID=9386400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE9090402722T Expired - Fee Related DE69000288T2 (de) | 1989-10-13 | 1990-10-02 | Verfahren zur herstellung von dielektrischen fluessigkeiten. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5186864A (enExample) |
| EP (1) | EP0422986B1 (enExample) |
| JP (1) | JP2569214B2 (enExample) |
| KR (1) | KR930005531B1 (enExample) |
| CN (1) | CN1029005C (enExample) |
| AT (1) | ATE80176T1 (enExample) |
| CA (1) | CA2027445C (enExample) |
| DE (1) | DE69000288T2 (enExample) |
| DK (1) | DK0422986T3 (enExample) |
| ES (1) | ES2034844T3 (enExample) |
| FI (1) | FI97478C (enExample) |
| FR (1) | FR2653134B1 (enExample) |
| GR (1) | GR3006387T3 (enExample) |
| IE (1) | IE64608B1 (enExample) |
| NO (1) | NO904393L (enExample) |
| PT (1) | PT95588B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5977422A (en) * | 1997-06-09 | 1999-11-02 | The Dow Chemical Company | Organoaluminum catalysis of alkylation reactions |
| US20060100466A1 (en) * | 2004-11-08 | 2006-05-11 | Holmes Steven A | Cycloalkane base oils, cycloalkane-base dielectric liquids made using cycloalkane base oils, and methods of making same |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2012302A (en) * | 1933-04-04 | 1935-08-27 | Gen Electric | Halogenated material and process of preparing the same |
| US2556880A (en) * | 1945-08-17 | 1951-06-12 | Solar Mfg Corp | Synthetic oils and resins and methods of producing same |
| BE533352A (enExample) * | 1953-11-17 | 1954-12-15 | ||
| US3006972A (en) * | 1959-08-21 | 1961-10-31 | Standard Oil Co | Coupling of aromatic rings |
| US4197417A (en) * | 1977-09-28 | 1980-04-08 | Imperial Chemical Industries Limited | Process for the manufacture of o-benzyl toluenes |
| EP0008251B1 (fr) * | 1978-07-27 | 1982-02-17 | P C U K Produits Chimiques Ugine Kuhlmann | Nouveaux diélectriques liquides, procédé de préparation et applications |
| IT1138101B (it) * | 1981-07-24 | 1986-09-17 | Caffaro Ind Chimica Ed Elettro | Fluido dielettrico per trasformatori e procedimento per la sua preparazione |
| FR2552423B1 (fr) * | 1983-09-23 | 1985-10-25 | Ugine Kuhlmann | Compositions d'oligomeres de polyarylalcanes et leur procede de fabrication |
| DE3836780A1 (de) * | 1988-10-28 | 1990-05-03 | Bayer Ag | Verfahren zur herstellung von gegebenenfalls substituierten benzylbenzolen |
-
1989
- 1989-10-13 FR FR8913451A patent/FR2653134B1/fr not_active Expired - Lifetime
-
1990
- 1990-10-02 DK DK90402722.4T patent/DK0422986T3/da active
- 1990-10-02 EP EP90402722A patent/EP0422986B1/fr not_active Expired - Lifetime
- 1990-10-02 ES ES199090402722T patent/ES2034844T3/es not_active Expired - Lifetime
- 1990-10-02 AT AT90402722T patent/ATE80176T1/de active
- 1990-10-02 DE DE9090402722T patent/DE69000288T2/de not_active Expired - Fee Related
- 1990-10-11 NO NO90904393A patent/NO904393L/no unknown
- 1990-10-12 KR KR1019900016202A patent/KR930005531B1/ko not_active Expired - Fee Related
- 1990-10-12 CA CA002027445A patent/CA2027445C/fr not_active Expired - Fee Related
- 1990-10-12 PT PT95588A patent/PT95588B/pt not_active IP Right Cessation
- 1990-10-12 FI FI905033A patent/FI97478C/fi not_active IP Right Cessation
- 1990-10-12 JP JP2275155A patent/JP2569214B2/ja not_active Expired - Lifetime
- 1990-10-13 CN CN90108455A patent/CN1029005C/zh not_active Expired - Fee Related
- 1990-10-15 IE IE369290A patent/IE64608B1/en not_active IP Right Cessation
- 1990-10-15 US US07/597,030 patent/US5186864A/en not_active Expired - Fee Related
-
1992
- 1992-11-30 GR GR920402760T patent/GR3006387T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT95588A (pt) | 1991-09-13 |
| FI97478B (fi) | 1996-09-13 |
| FR2653134B1 (fr) | 1991-12-13 |
| GR3006387T3 (enExample) | 1993-06-21 |
| IE903692A1 (en) | 1991-04-24 |
| FI97478C (fi) | 1996-12-27 |
| JPH03134095A (ja) | 1991-06-07 |
| FR2653134A1 (fr) | 1991-04-19 |
| CN1050894A (zh) | 1991-04-24 |
| KR910008113A (ko) | 1991-05-30 |
| KR930005531B1 (ko) | 1993-06-22 |
| PT95588B (pt) | 1997-08-29 |
| NO904393L (no) | 1991-04-15 |
| CA2027445C (fr) | 1994-03-22 |
| CA2027445A1 (fr) | 1991-04-14 |
| CN1029005C (zh) | 1995-06-21 |
| DK0422986T3 (da) | 1992-10-05 |
| EP0422986A1 (fr) | 1991-04-17 |
| NO904393D0 (no) | 1990-10-11 |
| US5186864A (en) | 1993-02-16 |
| DE69000288D1 (de) | 1992-10-08 |
| JP2569214B2 (ja) | 1997-01-08 |
| ES2034844T3 (es) | 1993-04-01 |
| IE64608B1 (en) | 1995-08-23 |
| EP0422986B1 (fr) | 1992-09-02 |
| ATE80176T1 (de) | 1992-09-15 |
| FI905033A0 (fi) | 1990-10-12 |
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