FR2462454A1 - Copolycarbonate thermoplastique de poly(tere- ou isophtalate de bisphenol a) et son procede de fabrication - Google Patents
Copolycarbonate thermoplastique de poly(tere- ou isophtalate de bisphenol a) et son procede de fabrication Download PDFInfo
- Publication number
- FR2462454A1 FR2462454A1 FR8016365A FR8016365A FR2462454A1 FR 2462454 A1 FR2462454 A1 FR 2462454A1 FR 8016365 A FR8016365 A FR 8016365A FR 8016365 A FR8016365 A FR 8016365A FR 2462454 A1 FR2462454 A1 FR 2462454A1
- Authority
- FR
- France
- Prior art keywords
- bisphenol
- terephthalate
- isophthalate
- copolymer
- molar ratio
- 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
Links
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title claims abstract description 149
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims description 26
- 230000008569 process Effects 0.000 title claims description 6
- 229920001169 thermoplastic Polymers 0.000 title abstract description 6
- 239000004416 thermosoftening plastic Substances 0.000 title abstract description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims abstract description 55
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 23
- 239000012815 thermoplastic material Substances 0.000 claims abstract description 10
- 229920001577 copolymer Polymers 0.000 claims description 48
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 13
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 10
- 125000005587 carbonate group Chemical group 0.000 claims description 7
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 229920000515 polycarbonate Polymers 0.000 claims description 6
- 239000004417 polycarbonate Substances 0.000 claims description 6
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims description 5
- 229920001634 Copolyester Polymers 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims 2
- 229930185605 Bisphenol Natural products 0.000 claims 1
- 230000007775 late Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000463 material Substances 0.000 description 27
- 239000000047 product Substances 0.000 description 25
- 230000008602 contraction Effects 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 13
- 230000009477 glass transition Effects 0.000 description 11
- 230000035882 stress Effects 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 230000006835 compression Effects 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000009864 tensile test Methods 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HFNQLYDPNAZRCH-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O.OC(O)=O HFNQLYDPNAZRCH-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000002103 osmometry Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000000214 vapour pressure osmometry Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- QPFMBZIOSGYJDE-ZDOIIHCHSA-N 1,1,2,2-tetrachloroethane Chemical group Cl[13CH](Cl)[13CH](Cl)Cl QPFMBZIOSGYJDE-ZDOIIHCHSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 235000003197 Byrsonima crassifolia Nutrition 0.000 description 1
- 240000001546 Byrsonima crassifolia Species 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- 241000131009 Copris Species 0.000 description 1
- 102100037709 Desmocollin-3 Human genes 0.000 description 1
- 101000968042 Homo sapiens Desmocollin-2 Proteins 0.000 description 1
- 101000880960 Homo sapiens Desmocollin-3 Proteins 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002706 dry binder Substances 0.000 description 1
- 230000005489 elastic deformation Effects 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- -1 isophthaloyl Chemical group 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000008442 polyphenolic compounds Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical group [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 238000012345 traction test Methods 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- 229920006352 transparent thermoplastic Polymers 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000009278 visceral effect Effects 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
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7925845 | 1979-07-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2462454A1 true FR2462454A1 (fr) | 1981-02-13 |
| FR2462454B1 FR2462454B1 (enExample) | 1983-06-17 |
Family
ID=10506743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8016365A Granted FR2462454A1 (fr) | 1979-07-25 | 1980-07-24 | Copolycarbonate thermoplastique de poly(tere- ou isophtalate de bisphenol a) et son procede de fabrication |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US4355150A (enExample) |
| JP (1) | JPS5620029A (enExample) |
| BE (1) | BE884245A (enExample) |
| DE (1) | DE3028092A1 (enExample) |
| FR (1) | FR2462454A1 (enExample) |
| GB (1) | GB2060664B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0050847A1 (en) * | 1980-10-27 | 1982-05-05 | The Dow Chemical Company | Ordered copolyestercarbonate resins |
| EP0134898A1 (en) * | 1983-06-03 | 1985-03-27 | General Electric Company | Aromatic copolyester carbonate compositions |
| EP0219708A1 (de) * | 1985-10-05 | 1987-04-29 | Bayer Ag | Aromatische Polyestercarbonate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Formkörpern, Folien und Überzügen |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2060664B (en) * | 1979-07-25 | 1983-10-26 | Secr Defence | Polyester carbonates |
| US4429083A (en) | 1981-10-05 | 1984-01-31 | Idemitsu Kosan Company Limited | Process for the production of polyesterpolycarbonate |
| US4506065A (en) * | 1984-01-03 | 1985-03-19 | General Electric Company | Copolyestercarbonates |
| US4804700A (en) * | 1985-07-11 | 1989-02-14 | General Electric Company | Resinous compositions |
| US5614599A (en) * | 1994-10-31 | 1997-03-25 | The Dow Chemical Company | Stilbene-based polyester and polycarbonate compositions |
| US20090189321A1 (en) * | 2008-01-29 | 2009-07-30 | Dow Global Technologies Inc. | Thermoplastic composition and use for large parison blow molding applications |
| US8525191B2 (en) * | 2011-04-01 | 2013-09-03 | Sabic Innovative Plastics Ip B.V. | Optoelectronic devices and coatings therefore |
| US10066102B2 (en) | 2013-11-22 | 2018-09-04 | Trinseo Europe Gmbh | Polycarbonate containing compositions |
| KR101890500B1 (ko) | 2013-11-22 | 2018-08-21 | 트린세오 유럽 게엠베하 | 폴리카보네이트 함유 조성물 |
| WO2016042355A1 (en) | 2014-09-15 | 2016-03-24 | Trinseo Europe Gmbh | Flame retardant polycarbonates having high total luminous transmittance |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2346386A1 (fr) * | 1976-04-02 | 1977-10-28 | Allied Chem | Copolymeres bisphenol a terephtalate carbonate pouvant etre traites a l'etat de masse fondue |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT595468A (enExample) * | 1957-08-22 | |||
| US4156069A (en) * | 1976-04-02 | 1979-05-22 | Allied Chemical Corporation | Bisphenol-A/terephthalate/carbonate melt processable copolymers |
| US4260731A (en) * | 1978-09-11 | 1981-04-07 | Mitsubishi Chemical Industries, Ltd. | Aromatic polyester-polycarbonate |
| GB2060664B (en) * | 1979-07-25 | 1983-10-26 | Secr Defence | Polyester carbonates |
-
1980
- 1980-07-02 GB GB8021608A patent/GB2060664B/en not_active Expired
- 1980-07-09 BE BE0/201348A patent/BE884245A/fr not_active IP Right Cessation
- 1980-07-15 US US06/169,211 patent/US4355150A/en not_active Expired - Lifetime
- 1980-07-18 JP JP9862880A patent/JPS5620029A/ja active Granted
- 1980-07-24 FR FR8016365A patent/FR2462454A1/fr active Granted
- 1980-07-24 DE DE19803028092 patent/DE3028092A1/de not_active Withdrawn
-
1982
- 1982-07-16 US US06/399,128 patent/US4465814A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2346386A1 (fr) * | 1976-04-02 | 1977-10-28 | Allied Chem | Copolymeres bisphenol a terephtalate carbonate pouvant etre traites a l'etat de masse fondue |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0050847A1 (en) * | 1980-10-27 | 1982-05-05 | The Dow Chemical Company | Ordered copolyestercarbonate resins |
| EP0134898A1 (en) * | 1983-06-03 | 1985-03-27 | General Electric Company | Aromatic copolyester carbonate compositions |
| EP0219708A1 (de) * | 1985-10-05 | 1987-04-29 | Bayer Ag | Aromatische Polyestercarbonate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Formkörpern, Folien und Überzügen |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3028092A1 (de) | 1981-02-19 |
| FR2462454B1 (enExample) | 1983-06-17 |
| US4355150A (en) | 1982-10-19 |
| JPS6121487B2 (enExample) | 1986-05-27 |
| US4465814A (en) | 1984-08-14 |
| GB2060664A (en) | 1981-05-07 |
| JPS5620029A (en) | 1981-02-25 |
| GB2060664B (en) | 1983-10-26 |
| BE884245A (fr) | 1980-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |