CN1163481C - 有机二硫化物与多硫化物的合成 - Google Patents
有机二硫化物与多硫化物的合成 Download PDFInfo
- Publication number
- CN1163481C CN1163481C CNB991027612A CN99102761A CN1163481C CN 1163481 C CN1163481 C CN 1163481C CN B991027612 A CNB991027612 A CN B991027612A CN 99102761 A CN99102761 A CN 99102761A CN 1163481 C CN1163481 C CN 1163481C
- Authority
- CN
- China
- Prior art keywords
- resin
- polysulfide
- mercaptan
- sulfur
- preface
- 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 - Lifetime
Links
- 229920001021 polysulfide Polymers 0.000 title claims abstract description 31
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 229920005989 resin Polymers 0.000 claims abstract description 91
- 239000011347 resin Substances 0.000 claims abstract description 91
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000005077 polysulfide Substances 0.000 claims description 32
- 150000008117 polysulfides Polymers 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 239000011593 sulfur Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 239000005864 Sulphur Substances 0.000 claims description 14
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 12
- 150000008116 organic polysulfides Chemical class 0.000 claims description 10
- -1 polyethylene Polymers 0.000 claims description 10
- 239000004698 Polyethylene Substances 0.000 claims description 9
- 229920000768 polyamine Polymers 0.000 claims description 9
- 229920000573 polyethylene Polymers 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000008427 organic disulfides Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 230000008859 change Effects 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000007306 functionalization reaction Methods 0.000 claims description 3
- RBORURQQJIQWBS-QVRNUERCSA-N (4ar,6r,7r,7as)-6-(6-amino-8-bromopurin-9-yl)-2-hydroxy-2-sulfanylidene-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol Chemical compound C([C@H]1O2)OP(O)(=S)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1Br RBORURQQJIQWBS-QVRNUERCSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 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
- 150000001412 amines Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 150000003512 tertiary amines Chemical group 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 4
- 238000007265 chloromethylation reaction Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical class CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 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
- 239000012298 atmosphere Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012429 reaction media 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
- 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
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005303 weighing Methods 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 |
|---|---|---|---|
| FR98/00660 | 1998-01-22 | ||
| FR9800660A FR2773799B1 (fr) | 1998-01-22 | 1998-01-22 | Synthese de disulfures et polysulfures organiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1232024A CN1232024A (zh) | 1999-10-20 |
| CN1163481C true CN1163481C (zh) | 2004-08-25 |
Family
ID=9522034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB991027612A Expired - Lifetime CN1163481C (zh) | 1998-01-22 | 1999-01-22 | 有机二硫化物与多硫化物的合成 |
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 |
| KR102588712B1 (ko) | 2017-06-02 | 2023-10-17 | 코베스트로 (네덜란드) 비.브이. | 광섬유용의 내열성 방사선 경화성 코팅 |
| 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 |
| CN112203995B (zh) | 2018-06-01 | 2023-02-21 | 科思创(荷兰)有限公司 | 用于经由交替低聚物涂覆光纤的辐射可固化组合物及由其生产的涂层 |
| 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 |
| CN114144386B (zh) | 2019-05-24 | 2023-11-17 | 科思创(荷兰)有限公司 | 具有增强的高速可加工性的用于涂覆光纤的辐射可固化组合物 |
| 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 |
| EP4003927B1 (en) | 2019-07-31 | 2026-07-08 | Covestro (Netherlands) B.V. | Radiation curable compositions with multi-functional long-armed oligomers for coating optical fibers |
| 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 |
| CN115515784A (zh) | 2020-04-03 | 2022-12-23 | 科思创(荷兰)有限公司 | 多层光学器件 |
| WO2021202639A1 (en) | 2020-04-03 | 2021-10-07 | Dsm Ip Assets B.V. | Methods of synthesizing multi-hydrogen bonding oligomers |
| ES3058361T3 (es) | 2020-04-03 | 2026-03-10 | Covestro Netherlands Bv | Fibras ópticas de autorreparación y las composiciones utilizadas para crear las mismas |
| CN115777077A (zh) | 2020-06-30 | 2023-03-10 | 科思创(荷兰)有限公司 | 光纤涂料的粘度指数改进剂 |
| 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 |
| WO2023072891A1 (en) | 2021-10-29 | 2023-05-04 | Covestro (Netherlands) B.V. | Radical-curable composition |
| WO2023205221A2 (en) | 2022-04-21 | 2023-10-26 | Covestro (Netherlands) B.V. | Low-volatility radiation curable compositions for coating optical fibers |
| WO2023227680A1 (en) | 2022-05-25 | 2023-11-30 | Covestro (Netherlands) B.V. | Process for providing low gloss coatings |
| WO2024042082A1 (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 |
| DE68900007D1 (de) * | 1988-04-14 | 1990-10-04 | Elf Aquitaine | Verfahren zur herstellung von organischen di- und polysulfiden. |
| US5028259A (en) * | 1990-03-06 | 1991-07-02 | Henkel Research Corporation | Recovery of precious metal |
| 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 |
| 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 |
-
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 PT PT99400062T patent/PT931789E/pt unknown
- 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 AT AT99400062T patent/ATE200898T1/de not_active IP Right Cessation
- 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 CA CA002257487A patent/CA2257487A1/fr not_active Abandoned
- 1999-01-19 US US09/232,690 patent/US6020529A/en not_active Expired - Lifetime
- 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 CN CNB991027612A patent/CN1163481C/zh not_active Expired - Lifetime
- 1999-01-22 ID IDP990044D patent/ID22956A/id unknown
- 1999-01-22 AR ARP990100269A patent/AR014471A1/es active IP Right Grant
- 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 |
|---|---|
| EP0931789B1 (fr) | 2001-05-02 |
| PL330969A1 (en) | 1999-08-02 |
| FR2773799B1 (fr) | 2000-02-18 |
| KR19990067908A (ko) | 1999-08-25 |
| ES2157680T3 (es) | 2001-08-16 |
| AU750805B2 (en) | 2002-07-25 |
| SG74117A1 (en) | 2000-07-18 |
| HU223079B1 (hu) | 2004-03-29 |
| US6020529A (en) | 2000-02-01 |
| KR100594332B1 (ko) | 2006-06-28 |
| CN1232024A (zh) | 1999-10-20 |
| EP0931789A1 (fr) | 1999-07-28 |
| FR2773799A1 (fr) | 1999-07-23 |
| GR3036193T3 (en) | 2001-10-31 |
| DE69900093D1 (de) | 2001-06-07 |
| ZA99320B (en) | 1999-09-20 |
| HUP9900155A3 (en) | 2000-06-28 |
| ATE200898T1 (de) | 2001-05-15 |
| DE69900093T2 (de) | 2001-09-20 |
| CZ19299A3 (cs) | 1999-08-11 |
| SA99191080B1 (ar) | 2006-07-30 |
| CA2257487A1 (fr) | 1999-07-22 |
| MY128349A (en) | 2007-01-31 |
| HU9900155D0 (en) | 1999-04-28 |
| PT931789E (pt) | 2001-09-28 |
| ID22956A (id) | 1999-12-23 |
| CZ295773B6 (cs) | 2005-11-16 |
| AR014471A1 (es) | 2001-02-28 |
| JP4426008B2 (ja) | 2010-03-03 |
| HUP9900155A2 (hu) | 1999-09-28 |
| AU1317899A (en) | 2000-06-08 |
| JPH11255738A (ja) | 1999-09-21 |
| BR9900108A (pt) | 2000-07-25 |
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