AU750805B2 - Synthesis of organic disulphides and polysulphides - Google Patents
Synthesis of organic disulphides and polysulphides Download PDFInfo
- Publication number
- AU750805B2 AU750805B2 AU13178/99A AU1317899A AU750805B2 AU 750805 B2 AU750805 B2 AU 750805B2 AU 13178/99 A AU13178/99 A AU 13178/99A AU 1317899 A AU1317899 A AU 1317899A AU 750805 B2 AU750805 B2 AU 750805B2
- Authority
- AU
- Australia
- Prior art keywords
- resin
- polysulphide
- sulphur
- process according
- 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.)
- Ceased
Links
- 229920001021 polysulfide Polymers 0.000 title claims description 40
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- 229920005989 resin Polymers 0.000 claims description 77
- 239000011347 resin Substances 0.000 claims description 77
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 37
- 239000005864 Sulphur Substances 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 21
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims description 18
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 16
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 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 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 6
- WKAPDSOUKRNDLE-UHFFFAOYSA-N 2-prop-2-enoxyacetamide Chemical compound NC(=O)COCC=C WKAPDSOUKRNDLE-UHFFFAOYSA-N 0.000 description 5
- 150000003512 tertiary amines Chemical group 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
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical group CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 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
- -1 for example Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 150000003141 primary amines Chemical group 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GAYUSSOCODCSNF-UHFFFAOYSA-N 1-(dodecyldisulfanyl)dodecane Chemical class CCCCCCCCCCCCSSCCCCCCCCCCCC GAYUSSOCODCSNF-UHFFFAOYSA-N 0.000 description 1
- ODHAQPXNQDBHSH-UHFFFAOYSA-N Dicyclohexyl disulfide Chemical compound C1CCCCC1SSC1CCCCC1 ODHAQPXNQDBHSH-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 125000000320 amidine group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 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
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000007123 defense Effects 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
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003916 ethylene diamine group Chemical group 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 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
- 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
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 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
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 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
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 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 |
|---|---|---|---|
| FR9800660 | 1998-01-22 | ||
| FR9800660A FR2773799B1 (fr) | 1998-01-22 | 1998-01-22 | Synthese de disulfures et polysulfures organiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1317899A AU1317899A (en) | 2000-06-08 |
| AU750805B2 true AU750805B2 (en) | 2002-07-25 |
Family
ID=9522034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU13178/99A Ceased AU750805B2 (en) | 1998-01-22 | 1999-01-21 | Synthesis of organic disulphides and polysulphides |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6020529A (enExample) |
| EP (1) | EP0931789B1 (enExample) |
| JP (1) | JP4426008B2 (enExample) |
| KR (1) | KR100594332B1 (enExample) |
| CN (1) | CN1163481C (enExample) |
| AR (1) | AR014471A1 (enExample) |
| AT (1) | ATE200898T1 (enExample) |
| AU (1) | AU750805B2 (enExample) |
| BR (1) | BR9900108A (enExample) |
| CA (1) | CA2257487A1 (enExample) |
| CZ (1) | CZ295773B6 (enExample) |
| DE (1) | DE69900093T2 (enExample) |
| ES (1) | ES2157680T3 (enExample) |
| FR (1) | FR2773799B1 (enExample) |
| GR (1) | GR3036193T3 (enExample) |
| HU (1) | HU223079B1 (enExample) |
| ID (1) | ID22956A (enExample) |
| MY (1) | MY128349A (enExample) |
| PL (1) | PL330969A1 (enExample) |
| PT (1) | PT931789E (enExample) |
| SA (1) | SA99191080B1 (enExample) |
| SG (1) | SG74117A1 (enExample) |
| ZA (1) | ZA99320B (enExample) |
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 |
| JP7111432B2 (ja) | 2017-06-02 | 2022-08-02 | コベストロ （ネザーランズ） ビー．ブイ． | 光ファイバー用耐熱放射線硬化性コーティング |
| PL3687949T3 (pl) | 2017-11-03 | 2024-11-04 | Covestro (Netherlands) B.V. | Układy blokujące wodę zawierające włókna powleczone ciekłymi, utwardzanymi promieniowaniem kompozycjami sap |
| BR112020024440A2 (pt) | 2018-06-01 | 2021-03-23 | Dsm Ip Assets B.V. | composições curáveis por radiação para revestir fibra ótica e os revestimentos produzidos a partir das mesmas |
| JP2022509797A (ja) | 2018-12-03 | 2022-01-24 | コベストロ （ネザーランズ） ビー．ヴィー． | 光ファイバーをコーティングするための充填放射線硬化性組成物およびそれから製造されるコーティング |
| US10894858B2 (en) | 2019-05-24 | 2021-01-19 | Dsm Ip Assets B.V. | Radiation curable compositions for coating optical fiber with enhanced high-speed processability |
| 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 |
| JP7712261B2 (ja) | 2019-07-31 | 2025-07-23 | コベストロ （ネザーランズ） ビー．ブイ． | 光ファイバーを被覆するための多官能性長アームオリゴマーを含む放射線硬化性組成物 |
| 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 |
| US20230117457A1 (en) | 2020-04-03 | 2023-04-20 | Covestro (Netherlands) B.V. | Methods of synthesizing multi-hydrogen bonding oligomers |
| WO2021202638A1 (en) | 2020-04-03 | 2021-10-07 | Dsm Ip Assets B.V. | Multi-layered optical devices |
| WO2021202623A1 (en) | 2020-04-03 | 2021-10-07 | Dsm Ip Assets B.V. | Self-healing optical fibers and the compositions used to create the same |
| 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 |
| CN116888221A (zh) | 2021-02-22 | 2023-10-13 | 科思创(荷兰)有限公司 | 提供低光泽涂层的方法 |
| 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 |
| EP4423155B1 (en) | 2021-10-29 | 2025-10-01 | Covestro (Netherlands) B.V. | Radical-curable composition |
| WO2023205224A2 (en) | 2022-04-21 | 2023-10-26 | Covestro (Netherlands) B.V. | Low-volatility radiation curable compositions for coating optical fibers |
| US20250360534A1 (en) | 2022-05-25 | 2025-11-27 | Covestro (Netherlands) B.V. | Process for providing low gloss coatings |
| WO2024042074A1 (en) | 2022-08-24 | 2024-02-29 | Covestro (Netherlands) B.V. | Process for providing low gloss coatings |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1250430B (enExample) * | 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 |
| ES2017015B3 (es) * | 1988-04-14 | 1990-12-16 | Soc Nat Elf Aquitaine (Production) | Procedimiento de preparacion de disulfuros y polisulfuros organicos |
| 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 MY MYPI99000171A patent/MY128349A/en unknown
- 1999-01-15 KR KR19990000917A patent/KR100594332B1/ko not_active Expired - Fee Related
- 1999-01-18 SG SG1999000107A patent/SG74117A1/en unknown
- 1999-01-18 ZA ZA9900320A patent/ZA99320B/xx unknown
- 1999-01-19 CA CA002257487A patent/CA2257487A1/fr not_active Abandoned
- 1999-01-19 BR BR9900108-0A patent/BR9900108A/pt not_active Application Discontinuation
- 1999-01-19 US US09/232,690 patent/US6020529A/en not_active Expired - Lifetime
- 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 CN CNB991027612A patent/CN1163481C/zh not_active Expired - Lifetime
- 1999-01-22 ID IDP990044D patent/ID22956A/id unknown
- 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 |
|---|---|
| AR014471A1 (es) | 2001-02-28 |
| HUP9900155A3 (en) | 2000-06-28 |
| CN1232024A (zh) | 1999-10-20 |
| JP4426008B2 (ja) | 2010-03-03 |
| ID22956A (id) | 1999-12-23 |
| ES2157680T3 (es) | 2001-08-16 |
| SA99191080B1 (ar) | 2006-07-30 |
| KR19990067908A (ko) | 1999-08-25 |
| US6020529A (en) | 2000-02-01 |
| CA2257487A1 (fr) | 1999-07-22 |
| PL330969A1 (en) | 1999-08-02 |
| CZ19299A3 (cs) | 1999-08-11 |
| HUP9900155A2 (hu) | 1999-09-28 |
| CN1163481C (zh) | 2004-08-25 |
| SG74117A1 (en) | 2000-07-18 |
| PT931789E (pt) | 2001-09-28 |
| FR2773799A1 (fr) | 1999-07-23 |
| EP0931789B1 (fr) | 2001-05-02 |
| MY128349A (en) | 2007-01-31 |
| EP0931789A1 (fr) | 1999-07-28 |
| AU1317899A (en) | 2000-06-08 |
| BR9900108A (pt) | 2000-07-25 |
| HU223079B1 (hu) | 2004-03-29 |
| JPH11255738A (ja) | 1999-09-21 |
| FR2773799B1 (fr) | 2000-02-18 |
| DE69900093D1 (de) | 2001-06-07 |
| CZ295773B6 (cs) | 2005-11-16 |
| HU9900155D0 (en) | 1999-04-28 |
| ATE200898T1 (de) | 2001-05-15 |
| DE69900093T2 (de) | 2001-09-20 |
| GR3036193T3 (en) | 2001-10-31 |
| ZA99320B (en) | 1999-09-20 |
| KR100594332B1 (ko) | 2006-06-28 |
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