CA2257487A1 - Synthese de disulfures et polysulfures organiques - Google Patents
Synthese de disulfures et polysulfures organiques Download PDFInfo
- Publication number
- CA2257487A1 CA2257487A1 CA002257487A CA2257487A CA2257487A1 CA 2257487 A1 CA2257487 A1 CA 2257487A1 CA 002257487 A CA002257487 A CA 002257487A CA 2257487 A CA2257487 A CA 2257487A CA 2257487 A1 CA2257487 A1 CA 2257487A1
- Authority
- CA
- Canada
- Prior art keywords
- resin
- sulfur
- polysulfide
- reaction
- mercaptan
- 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.)
- Abandoned
Links
- 239000005077 polysulfide Substances 0.000 title claims abstract description 31
- 150000008116 organic polysulfides Polymers 0.000 title claims abstract description 14
- 150000008427 organic disulfides Chemical class 0.000 title claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- 229920005989 resin Polymers 0.000 claims abstract description 81
- 239000011347 resin Substances 0.000 claims abstract description 81
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims abstract description 17
- -1 polyethylene Polymers 0.000 claims abstract description 14
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004698 Polyethylene Substances 0.000 claims abstract description 10
- 229920000768 polyamine Polymers 0.000 claims abstract description 9
- 229920000573 polyethylene Polymers 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 37
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 239000011593 sulfur Substances 0.000 claims description 35
- 229920001021 polysulfide Polymers 0.000 claims description 28
- 150000008117 polysulfides Polymers 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 17
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 5
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000376 reactant Substances 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 150000002019 disulfides Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- 150000003512 tertiary amines Chemical group 0.000 description 5
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 3
- WKAPDSOUKRNDLE-UHFFFAOYSA-N 2-prop-2-enoxyacetamide Chemical compound NC(=O)COCC=C WKAPDSOUKRNDLE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 125000003916 ethylene diamine group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical group CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- ODHAQPXNQDBHSH-UHFFFAOYSA-N Dicyclohexyl disulfide Chemical class C1CCCCC1SSC1CCCCC1 ODHAQPXNQDBHSH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002891 organic anions Chemical group 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9800660A FR2773799B1 (fr) | 1998-01-22 | 1998-01-22 | Synthese de disulfures et polysulfures organiques |
| FR9800660 | 1998-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2257487A1 true CA2257487A1 (fr) | 1999-07-22 |
Family
ID=9522034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002257487A Abandoned CA2257487A1 (fr) | 1998-01-22 | 1999-01-19 | Synthese de disulfures et polysulfures organiques |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6020529A (https=) |
| EP (1) | EP0931789B1 (https=) |
| JP (1) | JP4426008B2 (https=) |
| KR (1) | KR100594332B1 (https=) |
| CN (1) | CN1163481C (https=) |
| AR (1) | AR014471A1 (https=) |
| AT (1) | ATE200898T1 (https=) |
| AU (1) | AU750805B2 (https=) |
| BR (1) | BR9900108A (https=) |
| CA (1) | CA2257487A1 (https=) |
| CZ (1) | CZ295773B6 (https=) |
| DE (1) | DE69900093T2 (https=) |
| ES (1) | ES2157680T3 (https=) |
| FR (1) | FR2773799B1 (https=) |
| GR (1) | GR3036193T3 (https=) |
| HU (1) | HU223079B1 (https=) |
| ID (1) | ID22956A (https=) |
| MY (1) | MY128349A (https=) |
| PL (1) | PL330969A1 (https=) |
| PT (1) | PT931789E (https=) |
| SA (1) | SA99191080B1 (https=) |
| SG (1) | SG74117A1 (https=) |
| ZA (1) | ZA99320B (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19854427A1 (de) * | 1998-11-25 | 2000-05-31 | Basf Ag | Verfahren zur Herstellung von organischen Disulfiden |
| DE19942395A1 (de) * | 1999-09-06 | 2001-03-08 | Bayer Ag | Verfahren zur Herstellung von Polythiopolycarbonsäuren |
| FR2808272B1 (fr) * | 2000-04-28 | 2002-06-14 | Atofina | Procede de fabrication d'olefines sulfurees |
| JP5060036B2 (ja) * | 2005-09-29 | 2012-10-31 | Ｈｏｙａ株式会社 | ポリチオールオリゴマーの製造方法 |
| US8097229B2 (en) | 2006-01-17 | 2012-01-17 | Headwaters Technology Innovation, Llc | Methods for manufacturing functionalized inorganic oxides and polymers incorporating same |
| CN101475517B (zh) * | 2009-01-15 | 2012-08-15 | 河南大学 | 一种对称的含二硫键化合物的制备方法 |
| CN102010282B (zh) * | 2010-10-18 | 2014-04-16 | 四川大学 | 一种在水相中催化制备二芳基二硫化合物和二芳基二硒化合物的方法 |
| CN102391166A (zh) * | 2011-07-20 | 2012-03-28 | 彩虹集团公司 | 一种用于染料敏化太阳能电池的离子液体的制备方法 |
| EP3106488A1 (en) * | 2015-06-19 | 2016-12-21 | Université de Haute Alsace | Photobase-catalysed oxidative polymerisation of poly (disulphide)s |
| BR112019025345B1 (pt) | 2017-06-02 | 2022-09-27 | Covestro (Netherlands) B.V. | Fibra óptica revestida, composição curável por radiação para revestir uma fibra óptica, método para produzir uma fibra óptica revestida e cabo de fibra óptica |
| CN111315701B (zh) | 2017-11-03 | 2022-10-14 | 科思创(荷兰)有限公司 | 包含用液体可辐射固化超吸收性聚合物组合物涂布的纤维的阻水体系 |
| CN112437761B (zh) | 2018-06-01 | 2023-01-20 | 科思创(荷兰)有限公司 | 用于涂覆光纤的辐射可固化组合物及由其生产的涂层 |
| US20220017773A1 (en) | 2018-12-03 | 2022-01-20 | Ms Holding B.V. | Filled radiation curable compositions for coating optical fiber and the coatings produced therefrom |
| WO2020239563A1 (en) | 2019-05-24 | 2020-12-03 | Dsm Ip Assets B.V. | Radiation curable compositions for coating optical fiber with enhanced high-speed processability |
| US11932571B2 (en) | 2019-05-24 | 2024-03-19 | Covestro (Netherland) B.V. | Radiation curable compositions for coating optical fiber with enhanced high-speed processability |
| CN114207063B (zh) | 2019-07-31 | 2023-07-25 | 科思创(荷兰)有限公司 | 具有多功能长臂低聚物的涂覆光纤用辐射固化组合物 |
| CN111422942A (zh) * | 2020-03-23 | 2020-07-17 | 浙江工业大学 | 一种利用乙二胺基树脂同步还原-吸附水体中六价铬的方法 |
| CN115427853B (zh) | 2020-04-03 | 2026-03-13 | 科思创(荷兰)有限公司 | 自我修复光纤和用于制造其的组合物 |
| JP7793535B2 (ja) | 2020-04-03 | 2026-01-05 | コベストロ （ネザーランズ） ビー．ヴィー． | 多水素結合オリゴマーの合成方法 |
| CN115515784A (zh) | 2020-04-03 | 2022-12-23 | 科思创(荷兰)有限公司 | 多层光学器件 |
| WO2022002909A1 (en) | 2020-06-30 | 2022-01-06 | Covestro (Netherlands) B.V. | Viscosity index improvers in optical fiber coatings |
| US11459345B2 (en) * | 2020-08-14 | 2022-10-04 | The Goodyear Tire & Rubber Company | Method for the synthesis of asymmetric polysulfides |
| EP4294879A1 (en) | 2021-02-22 | 2023-12-27 | Covestro (Netherlands) B.V. | Process for providing low gloss coatings |
| CN113603656B (zh) * | 2021-10-08 | 2022-03-15 | 科迈化工股份有限公司 | 橡胶硫化促进剂mbts的生产工艺 |
| US12612534B2 (en) | 2021-10-29 | 2026-04-28 | Covestro (Netherlands) B.V. | Radical-curable composition |
| JP2025521371A (ja) | 2022-04-21 | 2025-07-09 | コベストロ （ネザーランズ） ビー．ヴィー． | 光ファイバを被覆するための低揮発性放射線硬化性組成物 |
| EP4532576A1 (en) | 2022-05-25 | 2025-04-09 | Covestro (Netherlands) B.V. | Process for providing low gloss coatings |
| EP4577609A1 (en) | 2022-08-24 | 2025-07-02 | Covestro (Netherlands) B.V. | Process for providing low gloss coatings |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1250430B (https=) * | 1963-05-20 | |||
| US4623711A (en) * | 1985-08-21 | 1986-11-18 | Products Research & Chemical Corp. | Modified disulfide polymer composition and method for making same from mercaptan terminated disulfide polymer and diethyl formal mercaptan terminated polysulfide |
| EP0337837B1 (fr) * | 1988-04-14 | 1990-08-29 | Societe Nationale Elf Aquitaine (Production) | Procédé de préparation de disulfures et polysulfures organiques |
| US5028259A (en) * | 1990-03-06 | 1991-07-02 | Henkel Research Corporation | Recovery of precious metal |
| FR2742144B1 (fr) * | 1995-12-11 | 1998-01-16 | Elf Aquitaine | Procede de preparation de disulfures et de polysulfures organiques en presence de resines polystyrene-divinylbenzene possedant des groupes amine primaire |
| FR2742145B1 (fr) * | 1995-12-11 | 1998-01-16 | Elf Aquitaine | Procede de preparation de disulfures et de polysulfures organiques en presence de resines polystyrene-divinylbenzene (ps-dvb) possedant des groupes guanidines ou amidines |
-
1998
- 1998-01-22 FR FR9800660A patent/FR2773799B1/fr not_active Expired - Fee Related
-
1999
- 1999-01-07 JP JP00183899A patent/JP4426008B2/ja not_active Expired - Fee Related
- 1999-01-12 AT AT99400062T patent/ATE200898T1/de not_active IP Right Cessation
- 1999-01-12 EP EP99400062A patent/EP0931789B1/fr not_active Expired - Lifetime
- 1999-01-12 DE DE69900093T patent/DE69900093T2/de not_active Expired - Lifetime
- 1999-01-12 PT PT99400062T patent/PT931789E/pt unknown
- 1999-01-12 ES ES99400062T patent/ES2157680T3/es not_active Expired - Lifetime
- 1999-01-15 KR KR19990000917A patent/KR100594332B1/ko not_active Expired - Fee Related
- 1999-01-15 MY MYPI99000171A patent/MY128349A/en unknown
- 1999-01-18 SG SG1999000107A patent/SG74117A1/en unknown
- 1999-01-18 ZA ZA9900320A patent/ZA99320B/xx unknown
- 1999-01-19 US US09/232,690 patent/US6020529A/en not_active Expired - Lifetime
- 1999-01-19 CA CA002257487A patent/CA2257487A1/fr not_active Abandoned
- 1999-01-19 BR BR9900108-0A patent/BR9900108A/pt not_active Application Discontinuation
- 1999-01-20 CZ CZ1999192A patent/CZ295773B6/cs not_active IP Right Cessation
- 1999-01-21 AU AU13178/99A patent/AU750805B2/en not_active Ceased
- 1999-01-21 PL PL99330969A patent/PL330969A1/xx not_active IP Right Cessation
- 1999-01-21 HU HU9900155A patent/HU223079B1/hu not_active IP Right Cessation
- 1999-01-22 AR ARP990100269A patent/AR014471A1/es active IP Right Grant
- 1999-01-22 ID IDP990044D patent/ID22956A/id unknown
- 1999-01-22 CN CNB991027612A patent/CN1163481C/zh not_active Expired - Lifetime
- 1999-02-17 SA SA99191080A patent/SA99191080B1/ar unknown
-
2001
- 2001-07-09 GR GR20010401041T patent/GR3036193T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CZ19299A3 (cs) | 1999-08-11 |
| ID22956A (id) | 1999-12-23 |
| EP0931789B1 (fr) | 2001-05-02 |
| MY128349A (en) | 2007-01-31 |
| BR9900108A (pt) | 2000-07-25 |
| HUP9900155A3 (en) | 2000-06-28 |
| PL330969A1 (en) | 1999-08-02 |
| EP0931789A1 (fr) | 1999-07-28 |
| PT931789E (pt) | 2001-09-28 |
| KR19990067908A (ko) | 1999-08-25 |
| DE69900093T2 (de) | 2001-09-20 |
| AU1317899A (en) | 2000-06-08 |
| HU9900155D0 (en) | 1999-04-28 |
| SG74117A1 (en) | 2000-07-18 |
| CZ295773B6 (cs) | 2005-11-16 |
| ATE200898T1 (de) | 2001-05-15 |
| CN1232024A (zh) | 1999-10-20 |
| FR2773799B1 (fr) | 2000-02-18 |
| AR014471A1 (es) | 2001-02-28 |
| ES2157680T3 (es) | 2001-08-16 |
| US6020529A (en) | 2000-02-01 |
| DE69900093D1 (de) | 2001-06-07 |
| JP4426008B2 (ja) | 2010-03-03 |
| KR100594332B1 (ko) | 2006-06-28 |
| SA99191080B1 (ar) | 2006-07-30 |
| GR3036193T3 (en) | 2001-10-31 |
| HUP9900155A2 (hu) | 1999-09-28 |
| ZA99320B (en) | 1999-09-20 |
| FR2773799A1 (fr) | 1999-07-23 |
| HU223079B1 (hu) | 2004-03-29 |
| CN1163481C (zh) | 2004-08-25 |
| JPH11255738A (ja) | 1999-09-21 |
| AU750805B2 (en) | 2002-07-25 |
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