CZ295773B6 - Způsob výroby organických disulfidů a polysulfidů - Google Patents
Způsob výroby organických disulfidů a polysulfidů Download PDFInfo
- Publication number
- CZ295773B6 CZ295773B6 CZ1999192A CZ19299A CZ295773B6 CZ 295773 B6 CZ295773 B6 CZ 295773B6 CZ 1999192 A CZ1999192 A CZ 1999192A CZ 19299 A CZ19299 A CZ 19299A CZ 295773 B6 CZ295773 B6 CZ 295773B6
- Authority
- CZ
- Czechia
- Prior art keywords
- resin
- sulfur
- polysulfide
- mercaptan
- order
- Prior art date
Links
- 239000005077 polysulfide Substances 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 150000008116 organic polysulfides Polymers 0.000 title claims abstract description 12
- 150000008427 organic disulfides Chemical class 0.000 title claims abstract description 5
- 229920005989 resin Polymers 0.000 claims abstract description 82
- 239000011347 resin Substances 0.000 claims abstract description 82
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 31
- 239000011593 sulfur Substances 0.000 claims abstract description 31
- 229920001021 polysulfide Polymers 0.000 claims abstract description 30
- 150000008117 polysulfides Polymers 0.000 claims abstract description 22
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims abstract description 15
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 14
- -1 polyethylene Polymers 0.000 claims abstract description 12
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000004698 Polyethylene Substances 0.000 claims abstract description 10
- 229920000768 polyamine Polymers 0.000 claims abstract description 10
- 229920000573 polyethylene Polymers 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000000524 functional group Chemical group 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 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 12
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 7
- 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
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-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
- 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
- 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
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000002019 disulfides Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002891 organic anions Chemical class 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 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 compound C1CCCCC1SSC1CCCCC1 ODHAQPXNQDBHSH-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000320 amidine group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- 238000003556 assay 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
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000000052 comparative effect Effects 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
- 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
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000003916 ethylene diamine group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 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
- 238000002156 mixing Methods 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
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 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
- 238000003756 stirring Methods 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9800660A FR2773799B1 (fr) | 1998-01-22 | 1998-01-22 | Synthese de disulfures et polysulfures organiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ19299A3 CZ19299A3 (cs) | 1999-08-11 |
| CZ295773B6 true CZ295773B6 (cs) | 2005-11-16 |
Family
ID=9522034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ1999192A CZ295773B6 (cs) | 1998-01-22 | 1999-01-20 | Způsob výroby organických disulfidů a polysulfidů |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6020529A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0931789B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4426008B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR100594332B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1163481C (cg-RX-API-DMAC7.html) |
| AR (1) | AR014471A1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE200898T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU750805B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR9900108A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2257487A1 (cg-RX-API-DMAC7.html) |
| CZ (1) | CZ295773B6 (cg-RX-API-DMAC7.html) |
| DE (1) | DE69900093T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2157680T3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2773799B1 (cg-RX-API-DMAC7.html) |
| GR (1) | GR3036193T3 (cg-RX-API-DMAC7.html) |
| HU (1) | HU223079B1 (cg-RX-API-DMAC7.html) |
| ID (1) | ID22956A (cg-RX-API-DMAC7.html) |
| MY (1) | MY128349A (cg-RX-API-DMAC7.html) |
| PL (1) | PL330969A1 (cg-RX-API-DMAC7.html) |
| PT (1) | PT931789E (cg-RX-API-DMAC7.html) |
| SA (1) | SA99191080B1 (cg-RX-API-DMAC7.html) |
| SG (1) | SG74117A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA99320B (cg-RX-API-DMAC7.html) |
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 |
| CN110944957B (zh) | 2017-06-02 | 2022-07-08 | 科思创(荷兰)有限公司 | 光纤用耐热性可辐射固化涂料 |
| EP3687949B1 (en) | 2017-11-03 | 2024-09-04 | Covestro (Netherlands) B.V. | Water-blocking systems including fibers coated with liquid radiation curable sap compositions |
| JP7218385B2 (ja) | 2018-06-01 | 2023-02-06 | コベストロ （ネザーランズ） ビー．ヴィー． | 交互オリゴマーを介して光ファイバーをコーティングするための放射線硬化性組成物とそれから生成されたコーティング |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| US12491704B2 (en) | 2020-04-03 | 2025-12-09 | Covestro (Netherlands) B.V. | Multi-layered optical devices |
| CN115397879A (zh) | 2020-04-03 | 2022-11-25 | 科思创(荷兰)有限公司 | 合成多氢键合低聚物的方法 |
| 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 |
| US20240052196A1 (en) | 2021-02-22 | 2024-02-15 | 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 |
| WO2023205223A1 (en) | 2022-04-21 | 2023-10-26 | Covestro (Netherlands) B.V. | Radiation curable compositions for coating optical fibers |
| EP4532576A1 (en) | 2022-05-25 | 2025-04-09 | Covestro (Netherlands) B.V. | Process for providing low gloss coatings |
| WO2024042073A1 (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 |
|---|---|---|---|---|
| BE648125A (cg-RX-API-DMAC7.html) * | 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 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 PL PL99330969A patent/PL330969A1/xx not_active IP Right Cessation
- 1999-01-21 HU HU9900155A patent/HU223079B1/hu not_active IP Right Cessation
- 1999-01-21 AU AU13178/99A patent/AU750805B2/en not_active Ceased
- 1999-01-22 ID IDP990044D patent/ID22956A/id unknown
- 1999-01-22 AR ARP990100269A patent/AR014471A1/es active IP Right Grant
- 1999-01-22 CN CNB991027612A patent/CN1163481C/zh not_active Expired - Lifetime
- 1999-02-17 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 |
|---|---|
| MY128349A (en) | 2007-01-31 |
| CN1163481C (zh) | 2004-08-25 |
| AU1317899A (en) | 2000-06-08 |
| AR014471A1 (es) | 2001-02-28 |
| PT931789E (pt) | 2001-09-28 |
| CA2257487A1 (fr) | 1999-07-22 |
| HU9900155D0 (en) | 1999-04-28 |
| ES2157680T3 (es) | 2001-08-16 |
| HUP9900155A2 (hu) | 1999-09-28 |
| JP4426008B2 (ja) | 2010-03-03 |
| SA99191080B1 (ar) | 2006-07-30 |
| PL330969A1 (en) | 1999-08-02 |
| SG74117A1 (en) | 2000-07-18 |
| GR3036193T3 (en) | 2001-10-31 |
| DE69900093T2 (de) | 2001-09-20 |
| KR19990067908A (ko) | 1999-08-25 |
| US6020529A (en) | 2000-02-01 |
| AU750805B2 (en) | 2002-07-25 |
| HUP9900155A3 (en) | 2000-06-28 |
| EP0931789B1 (fr) | 2001-05-02 |
| FR2773799B1 (fr) | 2000-02-18 |
| HU223079B1 (hu) | 2004-03-29 |
| ID22956A (id) | 1999-12-23 |
| JPH11255738A (ja) | 1999-09-21 |
| CZ19299A3 (cs) | 1999-08-11 |
| DE69900093D1 (de) | 2001-06-07 |
| EP0931789A1 (fr) | 1999-07-28 |
| ATE200898T1 (de) | 2001-05-15 |
| FR2773799A1 (fr) | 1999-07-23 |
| CN1232024A (zh) | 1999-10-20 |
| ZA99320B (en) | 1999-09-20 |
| KR100594332B1 (ko) | 2006-06-28 |
| BR9900108A (pt) | 2000-07-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20080120 |