AU664388B2 - Process for the production of high molecular weight polyester resins - Google Patents
Process for the production of high molecular weight polyester resins Download PDFInfo
- Publication number
- AU664388B2 AU664388B2 AU27583/92A AU2758392A AU664388B2 AU 664388 B2 AU664388 B2 AU 664388B2 AU 27583/92 A AU27583/92 A AU 27583/92A AU 2758392 A AU2758392 A AU 2758392A AU 664388 B2 AU664388 B2 AU 664388B2
- Authority
- AU
- Australia
- Prior art keywords
- intrinsic viscosity
- process according
- melt
- polyester resin
- document
- 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
Links
- 229920001225 polyester resin Polymers 0.000 title claims abstract description 40
- 239000004645 polyester resin Substances 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 239000000155 melt Substances 0.000 claims abstract description 21
- 239000000654 additive Substances 0.000 claims abstract description 18
- 239000007787 solid Substances 0.000 claims abstract description 15
- 230000000996 additive effect Effects 0.000 claims abstract description 14
- 229920005989 resin Polymers 0.000 claims abstract description 14
- 239000011347 resin Substances 0.000 claims abstract description 14
- 239000002245 particle Substances 0.000 claims abstract description 12
- 238000002844 melting Methods 0.000 claims abstract description 8
- 230000008018 melting Effects 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 3
- 238000002156 mixing Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 238000006068 polycondensation reaction Methods 0.000 claims description 17
- 229920000728 polyester Polymers 0.000 claims description 10
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 7
- 238000007259 addition reaction Methods 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- 125000006159 dianhydride group Chemical group 0.000 claims description 3
- 238000010101 extrusion blow moulding Methods 0.000 claims description 2
- 238000010102 injection blow moulding Methods 0.000 claims description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 2
- 241000283014 Dama Species 0.000 claims 1
- JNSGIVNNHKGGRU-JYRVWZFOSA-N diethoxyphosphinothioyl (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate Chemical compound CCOP(=S)(OCC)OC(=O)C(=N/OC)\C1=CSC(N)=N1 JNSGIVNNHKGGRU-JYRVWZFOSA-N 0.000 claims 1
- 125000006160 pyromellitic dianhydride group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 11
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- -1 antioxydants Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- 241001527902 Aratus Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/80—Solid-state polycondensation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/25—Component parts, details or accessories; Auxiliary operations
- B29C48/36—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die
- B29C48/395—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using screws surrounded by a cooperating barrel, e.g. single screw extruders
- B29C48/40—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using screws surrounded by a cooperating barrel, e.g. single screw extruders using two or more parallel screws or at least two parallel non-intermeshing screws, e.g. twin screw extruders
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/022—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the choice of material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Blow-Moulding Or Thermoforming Of Plastics Or The Like (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI91A2759 | 1991-10-18 | ||
| ITMI912759A IT1251953B (it) | 1991-10-18 | 1991-10-18 | Procedimento per la produzione di resine poliestere ad elevato peso molecolare. |
| PCT/EP1992/002375 WO1993008226A1 (en) | 1991-10-18 | 1992-10-15 | Process for the production of high molecular weight polyester resins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2758392A AU2758392A (en) | 1993-05-21 |
| AU664388B2 true AU664388B2 (en) | 1995-11-16 |
Family
ID=11360893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU27583/92A Expired AU664388B2 (en) | 1991-10-18 | 1992-10-15 | Process for the production of high molecular weight polyester resins |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5376734A (enExample) |
| EP (1) | EP0563354B8 (enExample) |
| JP (1) | JP2790917B2 (enExample) |
| KR (1) | KR930703375A (enExample) |
| AT (1) | ATE254640T1 (enExample) |
| AU (1) | AU664388B2 (enExample) |
| CA (1) | CA2096640C (enExample) |
| DE (1) | DE69233252T2 (enExample) |
| ES (1) | ES2208634T3 (enExample) |
| IT (1) | IT1251953B (enExample) |
| TW (1) | TW209230B (enExample) |
| WO (1) | WO1993008226A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1252223B (it) * | 1991-12-16 | 1995-06-05 | M & G Ricerche Spa | Resine poliestere cellulari e loro procedimento di preparazione |
| IT1258965B (it) * | 1992-06-10 | 1996-03-11 | Procedimento per la produzione di resine poliestere per fibre | |
| IT1264381B1 (it) * | 1993-05-07 | 1996-09-23 | M & G Ricerche Spa | Articoli formati da resine poliestere |
| US6673874B1 (en) | 1994-12-21 | 2004-01-06 | Imperial Chemical Industries Plc | Modified polymers |
| US6121387A (en) * | 1994-12-21 | 2000-09-19 | Imperial Chemical Industries, Plc | Process for preparing a coating composition |
| GB9425792D0 (en) * | 1994-12-21 | 1995-02-22 | Ici Plc | Modified polymers |
| US5830982A (en) * | 1995-01-20 | 1998-11-03 | E. I. Du Pont De Nemours And Company | Production of poly (ethylene terephthalate) |
| IT1275478B (it) * | 1995-07-05 | 1997-08-07 | M & G Ricerche Spa | Resine poliestere aventi migliorate proprieta' |
| IT1283590B1 (it) * | 1996-04-12 | 1998-04-22 | Sinco Eng Spa | Resine poliesteri aventi migliorate proprieta' reologiche (mg-18) |
| IT1283160B1 (it) * | 1996-07-15 | 1998-04-07 | Sinco Eng Spa | Film poliestere soffiato |
| IT1283166B1 (it) * | 1996-07-18 | 1998-04-07 | Sinco Eng Spa | Procedimento perfezionato per la produzione di resine poliestere |
| IT1283644B1 (it) * | 1996-08-01 | 1998-04-23 | Sinco Eng Spa | Procedimento perfezionato per la produzione di resine poliestere |
| IT1285525B1 (it) * | 1996-10-18 | 1998-06-08 | Sinco Eng Spa | Procedimento perfezionato per la stabilizzazione dimensionale di manufatti in polietilentereftalato |
| JP2001525431A (ja) * | 1997-12-01 | 2001-12-11 | ミニステロ・デル・ウニヴェルシタ・エ・デッラ・リチェルカ・シエンティフィカ・エ・テクノロジカ | ポリエステル樹脂の分子量を増加させる方法 |
| IT1298635B1 (it) * | 1998-03-17 | 2000-01-12 | Sinco Ricerche Spa | Resine poliestere aventi migliorate proprieta' |
| IT1307930B1 (it) * | 1999-01-26 | 2001-11-29 | Sinco Ricerche Spa | Articoli trasparenti in resina poliestere (mg32). |
| ES2246821T3 (es) * | 1999-05-21 | 2006-03-01 | Ciba Specialty Chemicals Holding Inc. | Aumento del peso molecular y modificaciones de policondensados. |
| JP4522000B2 (ja) * | 2001-02-01 | 2010-08-11 | 旭化成せんい株式会社 | 発泡体 |
| EP1338616A1 (en) * | 2002-02-22 | 2003-08-27 | Dsm N.V. | Process for preparing a high-molecular polyamide, polyester, copolyesters or polyester-amide block copolymer |
| KR101250302B1 (ko) * | 2004-12-07 | 2013-04-03 | 우데 인벤타-피쉬에르 아게 | 저 아세트알데히드 함량을 갖는 폴리에스테르 과립 및/또는성형제품의 제조방법 및 제조장치 |
| US20060178497A1 (en) * | 2005-02-04 | 2006-08-10 | Clemson University And Thordon Bearings, Inc. | Implantable biomedical devices including biocompatible polyurethanes |
| US8110265B2 (en) * | 2008-12-09 | 2012-02-07 | The Coca-Cola Company | Pet container and compositions having enhanced mechanical properties and gas barrier properties |
| PT3495126T (pt) * | 2017-12-05 | 2021-10-25 | Point Plastic S R L | Processo para extrusão de uma película à base de material termoplástico |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU8364591A (en) * | 1990-09-05 | 1992-03-12 | Harold Verity Smith | Polyethylene terephthalate compositions and methods of using thereof |
| AU1443392A (en) * | 1991-03-29 | 1992-11-02 | Sinco Engineering S.P.A. | Block copolyester resins |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE68922102T2 (de) * | 1989-10-13 | 1995-10-19 | Phobos Nv | Verfahren zur kontinuierlichen Herstellung von hochmolekularen Polyester-Harzen. |
| IT1245598B (it) * | 1991-03-29 | 1994-09-29 | M & G Ricerche Spa | Processo per la produzione di resine poliestere ad elevato peso molecolare |
| IT1245599B (it) * | 1991-03-29 | 1994-09-29 | M & G Ricerche Spa | Resine copoliestere ad elevato peso molecolare e basso punto di fusione |
| IT1245597B (it) * | 1991-03-29 | 1994-09-29 | M & G Ricerche Spa | Processo per la produzione di resine poliestere ad elevato peso molecolare |
-
1991
- 1991-10-18 IT ITMI912759A patent/IT1251953B/it active IP Right Grant
-
1992
- 1992-10-15 WO PCT/EP1992/002375 patent/WO1993008226A1/en not_active Ceased
- 1992-10-15 ES ES92921371T patent/ES2208634T3/es not_active Expired - Lifetime
- 1992-10-15 JP JP5507427A patent/JP2790917B2/ja not_active Expired - Lifetime
- 1992-10-15 US US08/074,865 patent/US5376734A/en not_active Expired - Lifetime
- 1992-10-15 AT AT92921371T patent/ATE254640T1/de not_active IP Right Cessation
- 1992-10-15 CA CA002096640A patent/CA2096640C/en not_active Expired - Lifetime
- 1992-10-15 EP EP92921371A patent/EP0563354B8/en not_active Expired - Lifetime
- 1992-10-15 KR KR1019930701869A patent/KR930703375A/ko not_active Ceased
- 1992-10-15 DE DE69233252T patent/DE69233252T2/de not_active Expired - Lifetime
- 1992-10-15 AU AU27583/92A patent/AU664388B2/en not_active Expired
- 1992-10-16 TW TW81108226A patent/TW209230B/zh not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU8364591A (en) * | 1990-09-05 | 1992-03-12 | Harold Verity Smith | Polyethylene terephthalate compositions and methods of using thereof |
| AU1443392A (en) * | 1991-03-29 | 1992-11-02 | Sinco Engineering S.P.A. | Block copolyester resins |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE254640T1 (de) | 2003-12-15 |
| EP0563354B1 (en) | 2003-11-19 |
| AU2758392A (en) | 1993-05-21 |
| JP2790917B2 (ja) | 1998-08-27 |
| ITMI912759A1 (it) | 1993-04-18 |
| ES2208634T3 (es) | 2004-06-16 |
| ITMI912759A0 (it) | 1991-10-18 |
| TW209230B (enExample) | 1993-07-11 |
| DE69233252T2 (de) | 2004-04-22 |
| JPH06503606A (ja) | 1994-04-21 |
| KR930703375A (ko) | 1993-11-29 |
| EP0563354B8 (en) | 2004-03-24 |
| IT1251953B (it) | 1995-05-27 |
| CA2096640C (en) | 2003-03-18 |
| US5376734A (en) | 1994-12-27 |
| WO1993008226A1 (en) | 1993-04-29 |
| DE69233252D1 (de) | 2003-12-24 |
| CA2096640A1 (en) | 1993-04-19 |
| EP0563354A1 (en) | 1993-10-06 |
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