CA1140698A - Anion exchange resins - Google Patents
Anion exchange resinsInfo
- Publication number
- CA1140698A CA1140698A CA000359654A CA359654A CA1140698A CA 1140698 A CA1140698 A CA 1140698A CA 000359654 A CA000359654 A CA 000359654A CA 359654 A CA359654 A CA 359654A CA 1140698 A CA1140698 A CA 1140698A
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- bromination
- group
- brominating agent
- alkyl groups
- 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
Links
- 239000003957 anion exchange resin Substances 0.000 title claims abstract description 23
- 229920000642 polymer Polymers 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 55
- 239000000178 monomer Substances 0.000 claims abstract description 39
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 26
- 230000031709 bromination Effects 0.000 claims abstract description 23
- 238000005893 bromination reaction Methods 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- FNXLCIKXHOPCKH-UHFFFAOYSA-N bromamine Chemical group BrN FNXLCIKXHOPCKH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000005576 amination reaction Methods 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 24
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 10
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 10
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 238000004132 cross linking Methods 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 6
- MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 claims description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- -1 acyl peroxide Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- ZJEQUGWMBSKCCM-UHFFFAOYSA-N 1-bromopiperidine-2,6-dione Chemical compound BrN1C(=O)CCCC1=O ZJEQUGWMBSKCCM-UHFFFAOYSA-N 0.000 claims description 5
- CTZSJHSBNAIBKP-UHFFFAOYSA-N 3-bromoimidazolidine-2,4-dione Chemical compound BrN1C(=O)CNC1=O CTZSJHSBNAIBKP-UHFFFAOYSA-N 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 5
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- OTVPURYEWXIAKH-UHFFFAOYSA-N n,n-dibromobenzenesulfonamide Chemical class BrN(Br)S(=O)(=O)C1=CC=CC=C1 OTVPURYEWXIAKH-UHFFFAOYSA-N 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 3
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical group [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 3
- CJNIONOGFFDYRR-UHFFFAOYSA-N 1-ethenyl-2,3,4-tripropylbenzene Chemical class CCCC1=CC=C(C=C)C(CCC)=C1CCC CJNIONOGFFDYRR-UHFFFAOYSA-N 0.000 claims description 2
- KBYCBXSZHLPJMQ-UHFFFAOYSA-N 1-ethenyl-2-ethyl-3,4-dimethylbenzene Chemical compound CCC1=C(C)C(C)=CC=C1C=C KBYCBXSZHLPJMQ-UHFFFAOYSA-N 0.000 claims description 2
- IHOBMYMDUFACTO-UHFFFAOYSA-N 1-ethenyl-2-ethyl-3-methylbenzene Chemical compound CCC1=C(C)C=CC=C1C=C IHOBMYMDUFACTO-UHFFFAOYSA-N 0.000 claims description 2
- XIYATWBVQHWJPH-UHFFFAOYSA-N 1-ethenyl-2-propylbenzene Chemical class CCCC1=CC=CC=C1C=C XIYATWBVQHWJPH-UHFFFAOYSA-N 0.000 claims description 2
- NGWNYUAWPDYKPC-UHFFFAOYSA-N 1-ethenyl-3,4-diethyl-2-methylbenzene Chemical compound C(C)C1=C(C(=C(C=C1)C=C)C)CC NGWNYUAWPDYKPC-UHFFFAOYSA-N 0.000 claims description 2
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 claims 4
- 239000003431 cross linking reagent Substances 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 35
- 229910052799 carbon Inorganic materials 0.000 description 28
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 27
- 229910052794 bromium Inorganic materials 0.000 description 27
- 239000000377 silicon dioxide Substances 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 239000011324 bead Substances 0.000 description 9
- 229950005499 carbon tetrachloride Drugs 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 238000005658 halogenation reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 230000026030 halogenation Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 3
- 229920006037 cross link polymer Polymers 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 238000005349 anion exchange Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002102 polyvinyl toluene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- 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
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/12—Macromolecular compounds
- B01J41/14—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7922394A FR2464967A1 (fr) | 1979-09-07 | 1979-09-07 | Preparation de resines echangeuses d'anions par bromation de polymeres vinylaromatiques |
| FR79.22394 | 1979-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1140698A true CA1140698A (en) | 1983-02-01 |
Family
ID=9229448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000359654A Expired CA1140698A (en) | 1979-09-07 | 1980-09-05 | Anion exchange resins |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4327191A (enExample) |
| EP (1) | EP0025385B1 (enExample) |
| JP (1) | JPS5653107A (enExample) |
| AU (1) | AU532157B2 (enExample) |
| CA (1) | CA1140698A (enExample) |
| DE (1) | DE3063145D1 (enExample) |
| DK (1) | DK154300C (enExample) |
| FR (1) | FR2464967A1 (enExample) |
| IE (1) | IE50599B1 (enExample) |
| NZ (1) | NZ194856A (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5984618A (ja) * | 1982-11-05 | 1984-05-16 | Nippon Denso Co Ltd | 車両用冷房装置 |
| US4544682A (en) * | 1984-08-24 | 1985-10-01 | The Dow Chemical Company | Polymeric compositions possessing improved flammability resistance |
| JPH0714489B2 (ja) * | 1988-06-13 | 1995-02-22 | 東京有機化学工業株式会社 | 陰イオン交換樹脂 |
| US6686035B2 (en) * | 1999-02-05 | 2004-02-03 | Waters Investments Limited | Porous inorganic/organic hybrid particles for chromatographic separations and process for their preparation |
| US6528167B2 (en) * | 2001-01-31 | 2003-03-04 | Waters Investments Limited | Porous hybrid particles with organic groups removed from the surface |
| EP1417366A4 (en) | 2001-08-09 | 2010-10-27 | Waters Technologies Corp | INORGANIC / ORGANIC HYBRID MONOLITHIC MATERIALS FOR CHROMATOGRAPHIC SEPARATIONS AND PROCESS FOR THEIR PREPARATION |
| GB2414993B (en) | 2002-10-30 | 2007-07-11 | Waters Investments Ltd | Porous inorganic/organic homogenous copolymeric hybrid materials for chromatographic separations and process for the preparation thereof |
| JP2007523331A (ja) * | 2004-02-17 | 2007-08-16 | ウオーターズ・インベストメンツ・リミテツド | 有機基を表面から除去した多孔質ハイブリッドモノリス材料 |
| US10773186B2 (en) | 2004-07-30 | 2020-09-15 | Waters Technologies Corporation | Porous inorganic/organic hybrid materials with ordered domains for chromatographic separations and processes for their preparation |
| WO2006019988A1 (en) | 2004-07-30 | 2006-02-23 | Waters Investments Limited | Porous inorganic/organic hybrid materials with ordered domains for chromatographic separations and processes for their preparation |
| US8697765B2 (en) | 2007-01-12 | 2014-04-15 | Waters Technologies Corporation | Porous carbon-heteroatom-silicon hybrid inorganic/organic materials for chromatographic separations and process for the preparation thereof |
| US11439977B2 (en) | 2009-06-01 | 2022-09-13 | Waters Technologies Corporation | Hybrid material for chromatographic separations comprising a superficially porous core and a surrounding material |
| JP6151021B2 (ja) | 2009-06-01 | 2017-06-21 | ウオーターズ・テクノロジーズ・コーポレイシヨン | クロマトグラフ分離用ハイブリッド材料 |
| EP3834927A1 (en) | 2010-07-26 | 2021-06-16 | Waters Technologies Corporation | Superficially porous materials comprising a substantially nonporous core having narrow particle size distribution; process for the preparation thereof; and use thereof for chromatographic separations |
| CN109070050A (zh) | 2016-03-06 | 2018-12-21 | 沃特世科技公司 | 用于色谱分离的具有窄颗粒尺寸分布的包含涂布的芯的表面多孔材料、其制备方法、以及其用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1168080B (de) * | 1964-04-16 | Bayer Ag | Verfahren zur Herstellung von feinteiligen, unloeslichen Kunststoffen mit anionenaustauschenden Eigenschaften | |
| US888007A (en) * | 1907-03-23 | 1908-05-19 | Turner Fricke Mfg Company | Starting mechanism for explosive-engines. |
| FR1071608A (fr) * | 1948-12-29 | 1954-09-02 | Dow Chemical Co | Perfectionnements aux résines échangeuses d'anions et à leurs procédés de fabrication de ces résines |
| US3337479A (en) * | 1966-05-31 | 1967-08-22 | Dow Chemical Co | Preparation of cation-exchange resins |
| UST888007I4 (en) | 1970-09-29 | 1971-07-20 | Defensive publication | |
| GB1456974A (en) * | 1973-01-10 | 1976-12-01 | Nat Res Dev | Ion exchange materials |
| FR2427343A1 (fr) * | 1978-05-31 | 1979-12-28 | Dia Prosim | Procede de bromation de resines a base de copolymeres vinylaromatiques reticules |
-
1979
- 1979-09-07 FR FR7922394A patent/FR2464967A1/fr not_active Withdrawn
-
1980
- 1980-08-18 US US06/178,893 patent/US4327191A/en not_active Expired - Lifetime
- 1980-08-29 EP EP80401238A patent/EP0025385B1/fr not_active Expired
- 1980-08-29 DE DE8080401238T patent/DE3063145D1/de not_active Expired
- 1980-09-05 AU AU62065/80A patent/AU532157B2/en not_active Expired
- 1980-09-05 NZ NZ194856A patent/NZ194856A/xx unknown
- 1980-09-05 IE IE1863/80A patent/IE50599B1/en not_active IP Right Cessation
- 1980-09-05 CA CA000359654A patent/CA1140698A/en not_active Expired
- 1980-09-05 DK DK377980A patent/DK154300C/da not_active IP Right Cessation
- 1980-09-05 JP JP12249180A patent/JPS5653107A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AU6206580A (en) | 1981-03-12 |
| JPS5653107A (en) | 1981-05-12 |
| EP0025385B1 (fr) | 1983-05-11 |
| NZ194856A (en) | 1982-09-07 |
| DK154300C (da) | 1989-03-28 |
| JPS61841B2 (enExample) | 1986-01-11 |
| DE3063145D1 (en) | 1983-06-16 |
| FR2464967A1 (fr) | 1981-03-20 |
| DK377980A (da) | 1981-03-08 |
| IE801863L (en) | 1981-03-07 |
| US4327191A (en) | 1982-04-27 |
| IE50599B1 (en) | 1986-05-28 |
| DK154300B (da) | 1988-10-31 |
| AU532157B2 (en) | 1983-09-22 |
| EP0025385A1 (fr) | 1981-03-18 |
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