NO319927B1 - Fremgangsmate for avionisering av vandige opplosninger av radiografiske joderte kontrastmidler for magnetisk resonanstomografi som er ustabile ved sur pH og anvendelse av apparat for samme - Google Patents
Fremgangsmate for avionisering av vandige opplosninger av radiografiske joderte kontrastmidler for magnetisk resonanstomografi som er ustabile ved sur pH og anvendelse av apparat for samme Download PDFInfo
- Publication number
- NO319927B1 NO319927B1 NO19996079A NO996079A NO319927B1 NO 319927 B1 NO319927 B1 NO 319927B1 NO 19996079 A NO19996079 A NO 19996079A NO 996079 A NO996079 A NO 996079A NO 319927 B1 NO319927 B1 NO 319927B1
- Authority
- NO
- Norway
- Prior art keywords
- layer
- column
- solution
- aqueous solutions
- contrast agents
- Prior art date
Links
- 230000002378 acidificating effect Effects 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 36
- 239000007864 aqueous solution Substances 0.000 title claims description 12
- 239000002872 contrast media Substances 0.000 title claims description 11
- 238000003325 tomography Methods 0.000 title 1
- 239000000243 solution Substances 0.000 claims description 66
- 150000001768 cations Chemical class 0.000 claims description 34
- 150000001450 anions Chemical class 0.000 claims description 26
- 238000005342 ion exchange Methods 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 10
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 10
- 238000002242 deionisation method Methods 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- NJKDOADNQSYQEV-UHFFFAOYSA-N iomeprol Chemical compound OCC(=O)N(C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NJKDOADNQSYQEV-UHFFFAOYSA-N 0.000 claims description 6
- 229960000780 iomeprol Drugs 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 5
- 238000002595 magnetic resonance imaging Methods 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000009423 ventilation Methods 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 238000005192 partition Methods 0.000 claims 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 19
- 238000010612 desalination reaction Methods 0.000 description 16
- 150000002500 ions Chemical class 0.000 description 16
- 239000012535 impurity Substances 0.000 description 15
- 229960005451 gadoteridol Drugs 0.000 description 11
- DPNNNPAKRZOSMO-UHFFFAOYSA-K gadoteridol Chemical compound [Gd+3].CC(O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 DPNNNPAKRZOSMO-UHFFFAOYSA-K 0.000 description 11
- 238000011033 desalting Methods 0.000 description 8
- 238000001728 nano-filtration Methods 0.000 description 8
- 230000008929 regeneration Effects 0.000 description 8
- 238000011069 regeneration method Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000005341 cation exchange Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZPDFIIGFYAHNSK-CTHHTMFSSA-K 2-[4,10-bis(carboxylatomethyl)-7-[(2r,3s)-1,3,4-trihydroxybutan-2-yl]-1,4,7,10-tetrazacyclododec-1-yl]acetate;gadolinium(3+) Chemical compound [Gd+3].OC[C@@H](O)[C@@H](CO)N1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 ZPDFIIGFYAHNSK-CTHHTMFSSA-K 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000909 electrodialysis Methods 0.000 description 3
- 229960003411 gadobutrol Drugs 0.000 description 3
- 150000003951 lactams Chemical group 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000005325 percolation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 description 2
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 description 2
- 229910003317 GdCl3 Inorganic materials 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- MEANOSLIBWSCIT-UHFFFAOYSA-K gadolinium trichloride Chemical compound Cl[Gd](Cl)Cl MEANOSLIBWSCIT-UHFFFAOYSA-K 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 description 1
- COFWQRPEYJADHT-UHFFFAOYSA-N 1-n,3-n-bis(2,3-dihydroxypropyl)-5-[(3-hydroxy-2-oxopropyl)amino]-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OCC(O)CNC(=O)C1=C(I)C(NCC(=O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I COFWQRPEYJADHT-UHFFFAOYSA-N 0.000 description 1
- JZNZSKXIEDHOBD-UHFFFAOYSA-N 2-[4,10-bis(carboxymethyl)-7-(1,3,4-trihydroxybutan-2-yl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound OCC(O)C(CO)N1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 JZNZSKXIEDHOBD-UHFFFAOYSA-N 0.000 description 1
- PTZQGISORONQSJ-UHFFFAOYSA-N 2-[4,10-bis(carboxymethyl)-7-formyl-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(C=O)CCN(CC(O)=O)CC1 PTZQGISORONQSJ-UHFFFAOYSA-N 0.000 description 1
- HHLZCENAOIROSL-UHFFFAOYSA-N 2-[4,7-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound OC(=O)CN1CCNCCN(CC(O)=O)CCN(CC(O)=O)CC1 HHLZCENAOIROSL-UHFFFAOYSA-N 0.000 description 1
- HBUBKKRHXORPQB-UUOKFMHZSA-N 2-fluoroadenosine Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O HBUBKKRHXORPQB-UUOKFMHZSA-N 0.000 description 1
- JUTMGMCHQBQNLX-UHFFFAOYSA-N 6-n,8-n-bis(2,3-dihydroxypropyl)-5,7-diiodo-4-methyl-3-oxo-1,4-benzoxazine-6,8-dicarboxamide Chemical compound IC1=C(C(=O)NCC(O)CO)C(I)=C(C(=O)NCC(O)CO)C2=C1N(C)C(=O)CO2 JUTMGMCHQBQNLX-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- IQUHNCOJRJBMSU-UHFFFAOYSA-N H3HP-DO3A Chemical compound CC(O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 IQUHNCOJRJBMSU-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- GUVXZFRDPCKWEM-UHFFFAOYSA-N pentalene Chemical compound C1=CC2=CC=CC2=C1 GUVXZFRDPCKWEM-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 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
- B01J39/04—Processes using organic exchangers
- B01J39/07—Processes using organic exchangers in the weakly acidic form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Treatment Of Water By Ion Exchange (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT97MI001370A IT1292127B1 (it) | 1997-06-11 | 1997-06-11 | Processo per la dissalazione di sostanze instabili a ph acidi |
| PCT/EP1998/003467 WO1998056504A1 (en) | 1997-06-11 | 1998-06-09 | METHOD FOR THE DEIONIZATION OF SUBSTANCES THAT ARE NOT STABLE AT ACIDIC pH |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO996079D0 NO996079D0 (no) | 1999-12-09 |
| NO996079L NO996079L (no) | 1999-12-09 |
| NO319927B1 true NO319927B1 (no) | 2005-10-03 |
Family
ID=11377335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19996079A NO319927B1 (no) | 1997-06-11 | 1999-12-09 | Fremgangsmate for avionisering av vandige opplosninger av radiografiske joderte kontrastmidler for magnetisk resonanstomografi som er ustabile ved sur pH og anvendelse av apparat for samme |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6066259A (cs) |
| EP (1) | EP0991471B1 (cs) |
| JP (1) | JP4157605B2 (cs) |
| CN (1) | CN1120753C (cs) |
| AT (1) | ATE248023T1 (cs) |
| AU (1) | AU8437698A (cs) |
| CZ (1) | CZ293928B6 (cs) |
| DE (1) | DE69817569T2 (cs) |
| DK (1) | DK0991471T3 (cs) |
| ES (1) | ES2205524T3 (cs) |
| IN (1) | IN185470B (cs) |
| IT (1) | IT1292127B1 (cs) |
| NO (1) | NO319927B1 (cs) |
| PT (1) | PT991471E (cs) |
| WO (1) | WO1998056504A1 (cs) |
| ZA (1) | ZA985024B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6281255B1 (en) * | 2000-06-06 | 2001-08-28 | Graver Technologies, Inc. | Methods for regeneration of weakly basic anion exchange resins with a combination of an alkali metal carbonate and an alkali metal bicarbonate |
| EP2185272B1 (en) * | 2007-08-27 | 2018-05-02 | Liebel-Flarsheim Company LLC | Removal of silica from water soluble compounds by nanofiltration and reverse phase chromatography |
| LT2896405T (lt) | 2011-04-21 | 2020-03-25 | Bayer Intellectual Property Gmbh | Didelio grynumo gadobutrolio gamyba |
| US12227527B2 (en) * | 2018-07-10 | 2025-02-18 | Biophore India Pharmaceuticals Pvt. Ltd | Process for the preparation of 2,2′,2″-(10-((2R,3S)-1,3,4-trihydroxy butan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl) triacetic acid and its complexes |
| JP7627048B2 (ja) * | 2019-11-08 | 2025-02-05 | 株式会社Local Power | 次亜塩素酸水溶液の調製方法及び弱酸性陽イオン交換体の再生処理方法 |
| WO2022117619A1 (en) * | 2020-12-04 | 2022-06-09 | Bracco Imaging Spa | Manufacturing process for preparing gadoteridol |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3388059A (en) * | 1967-08-28 | 1968-06-11 | Nalco Chemical Co | Acid water treating process |
| DE1920497B2 (de) * | 1969-04-23 | 1975-10-30 | Bayer Ag, 5090 Leverkusen | Aufbereitung von Lösungen mit einem schwach sauren Carboxylkationenaustauscher und einem stark basischen Anionenaustauscher |
| FR2033719A5 (cs) * | 1969-07-02 | 1970-12-04 | Resindion Spa | |
| US3618589A (en) * | 1970-03-16 | 1971-11-09 | Sybron Corp | Desalination process by ion exchange |
| US4131645A (en) * | 1974-11-21 | 1978-12-26 | Ethyl Corporation | Iodine recovery process |
| IT1193211B (it) * | 1979-08-09 | 1988-06-15 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico,metodo per la loro preparazione e mezzi di contrasto che li contengono |
| DE3102693C1 (de) * | 1981-01-28 | 1982-09-30 | Kernforschungszentrum Karlsruhe Gmbh, 7500 Karlsruhe | "Verfahren zur Regeneration von in wäßrigen Suspensionen vorliegenden, schwach sauren Ionenaustauscherharzen mit Kohlendioxid" |
| DE3229019A1 (de) * | 1982-08-04 | 1984-02-09 | Metallgesellschaft Ag, 6000 Frankfurt | Verfahren zum behandeln von abwasser |
| IT1248741B (it) * | 1991-02-26 | 1995-01-26 | Bracco Spa | Processo di concentrazione e di purificazione di composti organici |
| US5447635A (en) * | 1991-02-26 | 1995-09-05 | Bracco International B.V. | Process of concentration and purification of organic compounds |
| US5446125A (en) * | 1991-04-01 | 1995-08-29 | Ocg Microelectronic Materials, Inc. | Method for removing metal impurities from resist components |
| DE4304666A1 (de) * | 1993-02-16 | 1994-08-18 | Brita Wasserfilter | Verfahren zum Entsalzen von Wasser |
| EP0670184B1 (en) * | 1994-03-01 | 2001-09-05 | Mitsubishi Chemical Corporation | Method of demineralizing water or an aqueous solution |
| IT1274027B (it) * | 1994-03-03 | 1997-07-14 | Zambon Spa | Processo per la preparazione e purificazione di mezzi di contrasto iodurati |
| US5811581A (en) * | 1994-08-04 | 1998-09-22 | Dibra S.P.A. | Process for the purification of opacifying contrast agents |
-
1997
- 1997-06-11 IT IT97MI001370A patent/IT1292127B1/it active IP Right Grant
-
1998
- 1998-06-09 CZ CZ19994441A patent/CZ293928B6/cs not_active IP Right Cessation
- 1998-06-09 CN CN98806004A patent/CN1120753C/zh not_active Expired - Lifetime
- 1998-06-09 JP JP50158199A patent/JP4157605B2/ja not_active Expired - Lifetime
- 1998-06-09 ES ES98934942T patent/ES2205524T3/es not_active Expired - Lifetime
- 1998-06-09 EP EP98934942A patent/EP0991471B1/en not_active Expired - Lifetime
- 1998-06-09 WO PCT/EP1998/003467 patent/WO1998056504A1/en active IP Right Grant
- 1998-06-09 DE DE69817569T patent/DE69817569T2/de not_active Expired - Lifetime
- 1998-06-09 AT AT98934942T patent/ATE248023T1/de active
- 1998-06-09 PT PT98934942T patent/PT991471E/pt unknown
- 1998-06-09 AU AU84376/98A patent/AU8437698A/en not_active Abandoned
- 1998-06-09 DK DK98934942T patent/DK0991471T3/da active
- 1998-06-10 US US09/094,510 patent/US6066259A/en not_active Expired - Lifetime
- 1998-06-10 ZA ZA985024A patent/ZA985024B/xx unknown
- 1998-06-10 IN IN1254MA1998 patent/IN185470B/en unknown
-
1999
- 1999-12-09 NO NO19996079A patent/NO319927B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69817569T2 (de) | 2004-04-08 |
| CZ444199A3 (cs) | 2000-06-14 |
| IT1292127B1 (it) | 1999-01-25 |
| AU8437698A (en) | 1998-12-30 |
| DK0991471T3 (da) | 2003-12-22 |
| DE69817569D1 (de) | 2003-10-02 |
| CN1260736A (zh) | 2000-07-19 |
| US6066259A (en) | 2000-05-23 |
| EP0991471A1 (en) | 2000-04-12 |
| NO996079D0 (no) | 1999-12-09 |
| PT991471E (pt) | 2003-12-31 |
| ITMI971370A0 (cs) | 1997-06-11 |
| EP0991471B1 (en) | 2003-08-27 |
| ITMI971370A1 (it) | 1998-12-11 |
| WO1998056504A1 (en) | 1998-12-17 |
| CN1120753C (zh) | 2003-09-10 |
| ES2205524T3 (es) | 2004-05-01 |
| NO996079L (no) | 1999-12-09 |
| CZ293928B6 (cs) | 2004-08-18 |
| JP2002503144A (ja) | 2002-01-29 |
| IN185470B (cs) | 2001-01-27 |
| ZA985024B (en) | 1999-01-25 |
| JP4157605B2 (ja) | 2008-10-01 |
| ATE248023T1 (de) | 2003-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6858145B2 (en) | Method of removing organic impurities from water | |
| JP5189255B2 (ja) | 偏光フィルム製造廃液からのヨウ素回収方法 | |
| EP3688005A1 (en) | Process for the purification of a neutral human milk oligosaccharide (hmo) from microbial fermentation | |
| JP2007528781A (ja) | 連続式電気脱イオン装置および方法 | |
| KR20190072526A (ko) | 과산화수소 수용액의 정제 방법 및 정제 장치 | |
| Singh et al. | Removal of ammonia from coke‐plant wastewater by using synthetic zeolite | |
| CN106178591A (zh) | 一种净化有机胺的方法 | |
| JP2004512315A (ja) | オニウム化合物を含む溶液からオニウム水酸化物を除去するためのプロセス | |
| NO319927B1 (no) | Fremgangsmate for avionisering av vandige opplosninger av radiografiske joderte kontrastmidler for magnetisk resonanstomografi som er ustabile ved sur pH og anvendelse av apparat for samme | |
| US5028736A (en) | Process for the separation and recovery of naphthalene-sulfonic acids from aqueous solutions | |
| JPH11352283A (ja) | 復水処理方法及び復水脱塩装置 | |
| JP2012035163A (ja) | 膜分離用前処理装置及びそれを用いた膜分離方法 | |
| US6432306B1 (en) | Device for the deionization of substances that are not stable at acidic pH | |
| WO2008150298A1 (en) | Separation of citric acid from gluconic acid in fermentation broth using a weakly or strongly basic anionic exchange resin adsorbent | |
| EP1176143A1 (en) | Anhydrous purification of nicotine using an ion exchange resin | |
| JP3851491B2 (ja) | ホウ素溶離液の精製装置及び精製方法 | |
| JP2000202442A (ja) | 硼素含有水中の硼素の分離回収方法 | |
| RU2325469C2 (ru) | Способ извлечения йода и брома | |
| JP4733807B2 (ja) | ホウ素溶離液の精製方法及びホウ素原料の製造方法 | |
| JPH0712474B2 (ja) | 溶液中の硝酸イオンの除去方法 | |
| JP4280119B2 (ja) | イオパミドールの製造方法 | |
| Turek et al. | Electrodialytic utilization of boron IE column post-regeneration lyes | |
| JP2023178802A (ja) | シアヌル酸含有排水の処理方法 | |
| RU2271335C2 (ru) | Способ очистки сточных вод, содержащих поверхностно-активные вещества и неорганические соли | |
| AGADZHANYAN | Isolation of Citric Acid from a Citrate Solution |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |