DE69828697T2 - Bifunktionelle, auf Kronenether basierende stationäre Kationenaustauschphase für Flüssigchromatographie - Google Patents
Bifunktionelle, auf Kronenether basierende stationäre Kationenaustauschphase für Flüssigchromatographie Download PDFInfo
- Publication number
- DE69828697T2 DE69828697T2 DE69828697T DE69828697T DE69828697T2 DE 69828697 T2 DE69828697 T2 DE 69828697T2 DE 69828697 T DE69828697 T DE 69828697T DE 69828697 T DE69828697 T DE 69828697T DE 69828697 T2 DE69828697 T2 DE 69828697T2
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- DE
- Germany
- Prior art keywords
- cation
- cation exchange
- crown
- functional
- bifunctional
- 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
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- 238000005341 cation exchange Methods 0.000 title claims description 95
- 230000001588 bifunctional effect Effects 0.000 title claims description 78
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- 238000010828 elution Methods 0.000 claims description 30
- 238000005277 cation exchange chromatography Methods 0.000 claims description 27
- 229910052700 potassium Inorganic materials 0.000 claims description 27
- 150000007942 carboxylates Chemical class 0.000 claims description 22
- 125000004429 atom Chemical group 0.000 claims description 20
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 24
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
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- 125000005842 heteroatom Chemical group 0.000 description 7
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000009950 felting Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/26—Cation exchangers for chromatographic processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction, e.g. ion-exchange, ion-pair, ion-suppression or ion-exclusion
- B01D15/361—Ion-exchange
- B01D15/362—Cation-exchange
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/816,878 US5865994A (en) | 1997-03-13 | 1997-03-13 | Bifunctional crown ether-based cation-exchange stationary phase for liquid chromatography |
| US816878 | 1997-03-13 | ||
| PCT/US1998/004744 WO1998040144A1 (en) | 1997-03-13 | 1998-03-11 | Bifunctional crown ether-based cation-exchange stationary phase for liquid chromatography |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69828697D1 DE69828697D1 (de) | 2005-02-24 |
| DE69828697T2 true DE69828697T2 (de) | 2006-03-16 |
Family
ID=25221837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69828697T Expired - Lifetime DE69828697T2 (de) | 1997-03-13 | 1998-03-11 | Bifunktionelle, auf Kronenether basierende stationäre Kationenaustauschphase für Flüssigchromatographie |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5865994A (https=) |
| EP (1) | EP1007178B1 (https=) |
| JP (2) | JP4328389B2 (https=) |
| AU (1) | AU721216B2 (https=) |
| CA (1) | CA2283262C (https=) |
| DE (1) | DE69828697T2 (https=) |
| WO (1) | WO1998040144A1 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9700768D0 (sv) * | 1997-03-04 | 1997-03-04 | Pharmacia Biotech Ab | Förfarande för att introducera funktionalitet |
| US6017453A (en) * | 1997-06-30 | 2000-01-25 | Texas Instruments Incorporated | Apparatus and method for inline removal of impurities from wet chemicals |
| US6200478B1 (en) * | 1998-06-30 | 2001-03-13 | Texas Instruments Incorporated | Apparatus and method for inline removal of impurities from wet chemicals |
| JP3562393B2 (ja) * | 1999-08-11 | 2004-09-08 | 日本電気株式会社 | 移動通信システム及びそれに用いるプログラムダウンロード方法 |
| US20050084908A1 (en) * | 2000-11-06 | 2005-04-21 | Chugai Seiyaku Kabushiki Kaisha | Methods for detecting binding of low-molecular-weight compound and its binding partner molecule |
| US6558459B2 (en) | 2001-02-27 | 2003-05-06 | Hewlett-Packard Development Company | Derivatization of dyes/pigments with crown ethers and inkjet printing fluids containing the same |
| US6867295B2 (en) * | 2001-09-07 | 2005-03-15 | Dionex Corporation | Ion exchange cryptands covalently bound to substrates |
| US20030077656A1 (en) * | 2001-09-07 | 2003-04-24 | Bordunov Andrei V. | Derivatized macrocycle compound for covalent bonding to a substrate and method of forming and use |
| CA2464302A1 (en) * | 2001-11-26 | 2003-06-05 | Amersham Biosciences Ab | Post-modification of a porous support |
| JP2005510609A (ja) * | 2001-11-26 | 2005-04-21 | アメルシャム・バイオサイエンシーズ・アクチボラグ | 多孔性支持体の後修飾 |
| WO2004025685A1 (en) * | 2002-09-10 | 2004-03-25 | Koninklijke Philips Electronics N.V. | Vacuum display device with increased resolution |
| JP4265181B2 (ja) | 2002-09-11 | 2009-05-20 | 昭和電工株式会社 | 弱酸性陽イオン交換体の製造方法および陽イオンクロマトグラフィー用カラム |
| US6758967B1 (en) | 2003-04-28 | 2004-07-06 | Alltech Associates, Inc. | Liquid chromatography apparatus having two stationary phases |
| US7115528B2 (en) * | 2003-04-29 | 2006-10-03 | Micron Technology, Inc. | Systems and method for forming silicon oxide layers |
| US20040249010A1 (en) * | 2003-06-04 | 2004-12-09 | Honeywell International, Inc. | Azeotrope-like compositons of pentafluoropropane, chloropropane and methanol |
| US7147891B2 (en) * | 2004-02-11 | 2006-12-12 | Dionex Corporation | Polymer substrate coated with weak cationic-exchange functional layer |
| US7291395B2 (en) * | 2004-02-18 | 2007-11-06 | Dionex Corporation | Coated ion exchanged substrate and method of forming |
| FR2884253B1 (fr) * | 2005-04-08 | 2007-06-22 | Univ Lille Sciences Tech | Materiaux monolithiques fonctionnalisables |
| WO2009003952A2 (en) * | 2007-06-29 | 2009-01-08 | Pronota N.V. | Column and method for preparing a biological sample for protein profiling |
| EP2205672B1 (en) * | 2007-09-24 | 2014-04-30 | Secretary, Department of Atomic Energy | Non-ionic porous, small solid resin with chemically bonded crown ether |
| US9314712B2 (en) * | 2008-05-09 | 2016-04-19 | Dionex Corporation | Functionalized substrates with ion-exchange properties |
| WO2011146775A1 (en) | 2010-05-19 | 2011-11-24 | Dionex Corporation | Functionalized substrates with aromatic stacking properties |
| CN105289536B (zh) | 2011-02-14 | 2019-07-09 | 迪奥内克斯公司 | 液相色谱柱 |
| US9169331B2 (en) | 2012-12-21 | 2015-10-27 | Dionex Corporation | Separation of glycans by mixed-mode liquid chromatography |
| EP2745904B1 (en) | 2012-12-21 | 2015-12-16 | Dionex Corporation | HILIC/Anion-Exchange/Cation-Exchange Multimodal Media |
| US9310344B2 (en) | 2013-06-14 | 2016-04-12 | Dionex Corporation | HILIC/anion-exchange/cation-exchange multimodal media |
| JP6469516B2 (ja) * | 2015-05-08 | 2019-02-13 | 国立大学法人広島大学 | キャリアドーピング法および導電体 |
| JP6469515B2 (ja) * | 2015-05-08 | 2019-02-13 | 国立大学法人広島大学 | イオンチャネルを利用したイオン交換法およびイオン交換体 |
| US10641751B2 (en) | 2015-06-19 | 2020-05-05 | Dionex Corporation | Ion exchange chromatography column, method, and system thereof |
| US10118171B2 (en) * | 2015-07-30 | 2018-11-06 | Dionex Corporation | Ion-exchange composition comprising a complex of support particles, dispersant, and electrostatically bound layering particles |
| US10379090B2 (en) | 2016-06-17 | 2019-08-13 | Dionex Corporation | Charge reversible ion exchange resins, chromatography column, method, and system thereof |
| US10814319B2 (en) | 2016-09-30 | 2020-10-27 | Board Of Regents, University Of Texas System | Functionalized polyolefin capillaries for open tubular ion chromatography |
| US11266926B2 (en) | 2017-08-30 | 2022-03-08 | Cornell University | Fluorinated crown ethers and methods and systems for extraction of lithium using same |
| US12438190B2 (en) * | 2020-01-22 | 2025-10-07 | Enevate Corporation | Silicon-based energy storage devices with electrolyte containing crown ether based compounds |
| CN110412201A (zh) * | 2019-08-21 | 2019-11-05 | 中蓝长化工程科技有限公司 | 一种测定锂矿石中锂、钠、钾、铷、铯的方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4382124B1 (en) * | 1958-07-18 | 1994-10-04 | Rohm & Haas | Process for preparing macroreticular resins, copolymers and products of said process |
| US3925019A (en) * | 1973-08-06 | 1975-12-09 | Dow Chemical Co | Chromatographic analysis of ionic species |
| US3915642A (en) * | 1973-08-06 | 1975-10-28 | Dow Chemical Co | Quantitative analysis of single ion species |
| US3918906A (en) * | 1973-08-06 | 1975-11-11 | Dow Chemical Co | Determining total ionic content |
| US4256859A (en) * | 1979-03-28 | 1981-03-17 | The Dow Chemical Company | Substituted crown polyethers |
| US4351909A (en) * | 1979-10-01 | 1982-09-28 | The Dow Chemical Co. | High performance ion-exchange composition |
| JPS5763139A (en) * | 1980-10-02 | 1982-04-16 | Tokuyama Soda Co Ltd | Cation exchange body and its production |
| US4383047A (en) * | 1981-02-17 | 1983-05-10 | The Dow Chemical Company | High performance anion-exchange chromatographic packing composition |
| FR2570075B1 (fr) * | 1984-09-11 | 1987-10-23 | Centre Nat Rech Scient | Silice greffee complexante, son procede de preparation et ses applications en chromatographie |
| JPS62210053A (ja) * | 1986-03-07 | 1987-09-16 | Agency Of Ind Science & Technol | 光学異性体分離用充填剤 |
| US5179213A (en) * | 1987-09-04 | 1993-01-12 | Brigham Young University | Macrocyclic ligands bonded to an inorganic support matrix and a process for selectively and quantitatively removing and concentrating ions present at low concentrations from mixtures thereof with other ions |
| CA1331254C (en) * | 1989-02-27 | 1994-08-02 | Victor Berber Barretto | Ion-exchange composition employing resin attachment to dispersant and method for forming the same |
| JPH03140353A (ja) * | 1989-10-26 | 1991-06-14 | Toray Ind Inc | フッ素樹脂成型品 |
| US5110474A (en) * | 1990-04-09 | 1992-05-05 | Arch Development Corporation | Method for liquid chromatographic extraction of strontium from acid solutions |
| US5730874A (en) * | 1991-06-12 | 1998-03-24 | Idaho Research Foundation, Inc. | Extraction of metals using supercritical fluid and chelate forming legand |
| US5356538A (en) * | 1991-06-12 | 1994-10-18 | Idaho Research Foundation, Inc. | Supercritical fluid extraction |
| US5503933A (en) * | 1994-02-25 | 1996-04-02 | Purdue Research Foundation | Covalently bonded coatings |
-
1997
- 1997-03-13 US US08/816,878 patent/US5865994A/en not_active Expired - Lifetime
-
1998
- 1998-03-11 CA CA002283262A patent/CA2283262C/en not_active Expired - Fee Related
- 1998-03-11 WO PCT/US1998/004744 patent/WO1998040144A1/en not_active Ceased
- 1998-03-11 EP EP98909110A patent/EP1007178B1/en not_active Expired - Lifetime
- 1998-03-11 JP JP53974798A patent/JP4328389B2/ja not_active Expired - Fee Related
- 1998-03-11 AU AU66975/98A patent/AU721216B2/en not_active Ceased
- 1998-03-11 DE DE69828697T patent/DE69828697T2/de not_active Expired - Lifetime
- 1998-04-30 US US09/070,450 patent/US5968363A/en not_active Expired - Lifetime
-
2008
- 2008-06-25 JP JP2008166098A patent/JP2008291038A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE69828697D1 (de) | 2005-02-24 |
| AU721216B2 (en) | 2000-06-29 |
| JP4328389B2 (ja) | 2009-09-09 |
| US5865994A (en) | 1999-02-02 |
| CA2283262C (en) | 2007-09-11 |
| EP1007178B1 (en) | 2005-01-19 |
| JP2002511924A (ja) | 2002-04-16 |
| US5968363A (en) | 1999-10-19 |
| EP1007178A1 (en) | 2000-06-14 |
| EP1007178A4 (en) | 2002-03-06 |
| JP2008291038A (ja) | 2008-12-04 |
| AU6697598A (en) | 1998-09-29 |
| CA2283262A1 (en) | 1998-09-17 |
| WO1998040144A1 (en) | 1998-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |