JP5631363B2 - 改良されたシェル官能化イオン交換樹脂 - Google Patents
改良されたシェル官能化イオン交換樹脂 Download PDFInfo
- Publication number
- JP5631363B2 JP5631363B2 JP2012160281A JP2012160281A JP5631363B2 JP 5631363 B2 JP5631363 B2 JP 5631363B2 JP 2012160281 A JP2012160281 A JP 2012160281A JP 2012160281 A JP2012160281 A JP 2012160281A JP 5631363 B2 JP5631363 B2 JP 5631363B2
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- free radical
- polymer
- shell
- ion exchange
- 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 - Fee Related
Links
- 239000003456 ion exchange resin Substances 0.000 title claims description 15
- 229920003303 ion-exchange polymer Polymers 0.000 title claims description 15
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 title claims description 10
- 239000000178 monomer Substances 0.000 claims description 116
- 239000011324 bead Substances 0.000 claims description 62
- 229920000642 polymer Polymers 0.000 claims description 59
- 150000003254 radicals Chemical class 0.000 claims description 58
- 239000002245 particle Substances 0.000 claims description 50
- 239000011159 matrix material Substances 0.000 claims description 42
- 229920001577 copolymer Polymers 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 29
- 238000006116 polymerization reaction Methods 0.000 claims description 24
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 15
- 239000000725 suspension Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 9
- 238000006277 sulfonation reaction Methods 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 150000003440 styrenes Chemical class 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 238000007306 functionalization reaction Methods 0.000 claims description 4
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229920000131 polyvinylidene Polymers 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000011347 resin Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000003999 initiator Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000005576 amination reaction Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 230000008961 swelling Effects 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000003729 cation exchange resin Substances 0.000 description 5
- 229920006037 cross link polymer Polymers 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229940023913 cation exchange resins Drugs 0.000 description 4
- 239000013522 chelant Substances 0.000 description 4
- 238000007265 chloromethylation reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000005349 anion exchange Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 alkylene methacrylate Chemical compound 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ZJQIXGGEADDPQB-UHFFFAOYSA-N 1,2-bis(ethenyl)-3,4-dimethylbenzene Chemical group CC1=CC=C(C=C)C(C=C)=C1C ZJQIXGGEADDPQB-UHFFFAOYSA-N 0.000 description 1
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 description 1
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- MAEDLSNGVQYGPK-UHFFFAOYSA-N 2,2-diaminoacetic acid Chemical compound NC(N)C(O)=O MAEDLSNGVQYGPK-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- SMBYUOXUISCLCF-UHFFFAOYSA-N n-ethyl-n-methylpropan-1-amine Chemical compound CCCN(C)CC SMBYUOXUISCLCF-UHFFFAOYSA-N 0.000 description 1
- OOTKJPZEEVPWCR-UHFFFAOYSA-N n-methyl-1-pyridin-2-ylmethanamine Chemical compound CNCC1=CC=CC=N1 OOTKJPZEEVPWCR-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012508 resin bead Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000011179 visual inspection Methods 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
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
-
- 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
-
- 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
-
- 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
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/20—Aqueous medium with the aid of macromolecular dispersing agents
-
- 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
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2207/00—Properties characterising the ingredient of the composition
- C08L2207/53—Core-shell polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
- Polymerisation Methods In General (AREA)
Description
(a)二段階型フリーラジカルマトリックスを製造し;
(b)少なくとも1種のモノマーを含むモノマーフィードと、前記二段階型フリーラジカルマトリックスとを、前記二段階型フリーラジカルマトリックスが前記モノマーの重合を触媒してコア/シェル形態を有するコポリマービーズを形成するような条件下で接触させる;
ことを含む、改良されたシェル官能化イオン交換樹脂の製造方法が提供され、並びにこの方法で形成されるコア/シェルコポリマービーズが提供される。
(a)一段階型フリーラジカルマトリックスを製造し;
(b)少なくとも1種のモノマーを含むモノマーフィードと、前記一段階型フリーラジカルマトリックスとを、前記一段階型フリーラジカルマトリックスが前記モノマーの重合を触媒してコア/シェル形態を有するコポリマービーズを形成するような条件下で接触させる;
ことを含む、改良されたシェル官能化イオン交換樹脂の製造方法を提供する。
Claims (5)
- (a)二段階型フリーラジカルマトリックスを製造し;
(b)少なくとも1種のモノマーを含むモノマーフィードと、前記二段階型フリーラジカルマトリックスとを、前記二段階型フリーラジカルマトリックスが前記モノマーの重合を触媒してコア/シェル形態を有するコポリマービーズを形成するような条件下で接触させ;並びに
(c)ハロメチル化またはスルホン化によって前記コポリマービーズを官能化する;
ことを含む、改良されたシェル官能化イオン交換樹脂の製造方法であって、
前記二段階型フリーラジカルマトリックスが、
(i)懸濁媒体中に複数のシード粒子を懸濁し
(ii)フリーラジカル含有当初モノマーチャージを前記シード粒子に吸収させ、及び、
(iii)前記当初モノマーチャージにおけるモノマーを、ポリマーへのその変換が20〜95パーセントになるまで重合すること
を含むプロセスによって製造され、
ただし、前記コポリマービーズの官能化がハロメチル化を含む場合、当初モノマーチャージは少なくとも14重量パーセントの架橋性モノマーを含み、並びに、
前記コポリマービーズの官能化がスルホン化を含む場合、当初モノマーチャージは少なくとも16重量パーセントの架橋性モノマーを含む、
改良されたシェル官能化イオン交換樹脂の製造方法。 - 前記工程(iii)における重合が懸濁重合である請求項1に記載の方法。
- 前記二段階型フリーラジカルマトリックスおよび前記工程(iii)において重合されるモノマーが懸濁安定化剤を含む水溶液に懸濁される、請求項2に記載の方法。
- 前記フィードモノマーがジビニルベンゼン、およびアクリロニトリルを含むか、またはアクリル酸のエステルもしくはメタクリル酸のエステルを含む請求項1に記載の方法。
- 請求項1の方法であって、前記工程(ii)の当初モノマーチャージにおけるモノマーが、モノビニリデン芳香族モノマー、ハロ置換スチレン、ポリビニリデン芳香族モノマー、アルファ,ベータ−エチレン性不飽和カルボン酸のエステル、アルキレンジアクリラート、アルキレンジメタクリラート、およびこれら混合物からなる群から選択される方法によって製造されたシェル官能化イオン交換樹脂。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161529469P | 2011-08-31 | 2011-08-31 | |
US61/529,469 | 2011-08-31 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2013053300A JP2013053300A (ja) | 2013-03-21 |
JP5631363B2 true JP5631363B2 (ja) | 2014-11-26 |
Family
ID=46598398
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012160281A Expired - Fee Related JP5631363B2 (ja) | 2011-08-31 | 2012-07-19 | 改良されたシェル官能化イオン交換樹脂 |
Country Status (4)
Country | Link |
---|---|
US (1) | US8686055B2 (ja) |
EP (1) | EP2564926B1 (ja) |
JP (1) | JP5631363B2 (ja) |
CN (1) | CN102964470A (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8822554B2 (en) | 2011-10-04 | 2014-09-02 | Purolite Corporation | Aminated ion exchange resins and production methods thereof |
CN103435733B (zh) * | 2013-08-23 | 2016-06-15 | 南京大学 | 一种亲水性高比表面积磁性树脂及其制备方法和应用于快速萃取水体中邻苯二甲酸酯的方法 |
CN104177536A (zh) * | 2014-07-25 | 2014-12-03 | 南京大学 | 一种螯合树脂吸附材料及其制备方法 |
CN108126749B (zh) * | 2018-01-23 | 2020-10-02 | 中国科学院过程工程研究所 | 一种多孔碱性负载离子液体催化剂及其制备方法和用途 |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2500149A (en) | 1947-02-21 | 1950-03-14 | Dow Chemical Co | Sulfonation of copolymers of monovinyl-and polyvinyl-aromatic compounds |
US2632001A (en) | 1948-12-29 | 1953-03-17 | Dow Chemical Co | Anion exchange resins from tertiary amines and methyl styrene polymers |
US2632000A (en) | 1948-12-29 | 1953-03-17 | Dow Chemical Co | Anion exchange resins from amines and alkyl styrene polymers |
US2631127A (en) | 1949-09-24 | 1953-03-10 | Koppers Co Inc | Ion-exchange resins |
US2664801A (en) | 1950-04-04 | 1954-01-05 | Walter T E Eisbein | Developing apparatus |
US2616877A (en) | 1950-04-06 | 1952-11-04 | Dow Chemical Co | Process for aminating halomethylated copolymers |
US2642417A (en) | 1952-05-21 | 1953-06-16 | Dow Chemical Co | Process for making anionexchange resins |
US2764564A (en) | 1954-11-02 | 1956-09-25 | Dow Chemical Co | Resinous reaction products of phosphorus thiochloride and insoluble cross-linked vinyl aromatic copolymers |
US2992544A (en) | 1955-05-09 | 1961-07-18 | Dow Chemical Co | Insoluble resinous copolymers of (chloromethyl) styrene and polyvinyl aromatic hydrocarbons and nitrogen-containing derivatives of the copolymers |
US2888441A (en) | 1956-10-12 | 1959-05-26 | Dow Chemical Co | Chelating resins having alpha-aminocarboxylic acid groups on a polymerized vinylbenzylamine resin structure |
US2982749A (en) | 1957-07-15 | 1961-05-02 | Dow Chemical Co | Inverse suspension polymerization of water soluble unsaturated monomers |
US3266007A (en) | 1964-05-18 | 1966-08-09 | Sanders Associates Inc | High voltage terminal block |
CA1127791A (en) | 1978-05-19 | 1982-07-13 | Robert L. Albright | Method of suspension polymerization and apparatus therefor |
CA1166413A (en) | 1980-10-30 | 1984-05-01 | Edward E. Timm | Process and apparatus for preparing uniform size polymer beads |
JPS5780557A (en) * | 1980-11-10 | 1982-05-20 | Showa Denko Kk | Manufacture of filling agent for liquid-phase chromatography |
US4419245A (en) | 1982-06-30 | 1983-12-06 | Rohm And Haas Company | Copolymer process and product therefrom consisting of crosslinked seed bead swollen by styrene monomer |
CA1207950A (en) * | 1982-08-02 | 1986-07-15 | William I. Harris | Ion exchange resins |
GB8817051D0 (en) | 1988-07-18 | 1988-08-24 | Dow Stade Gmbh | Ion exchange resins beads & processes for preparing them |
USRE34112E (en) * | 1989-10-17 | 1992-10-27 | The Dow Chemical Company | Condensate purification process |
JP3087905B2 (ja) * | 1989-10-17 | 2000-09-18 | 株式会社荏原製作所 | 懸濁性不純物除去用吸着剤および除去方法 |
US4975201A (en) * | 1989-10-17 | 1990-12-04 | The Dow Chemical Company | Condensate purification process |
US5244926A (en) | 1992-06-16 | 1993-09-14 | The Dow Chemical Company | Preparation of ion exchange and adsorbent copolymers |
MXPA00012167A (es) * | 1999-12-24 | 2002-08-06 | Bayer Ag | Procedimiento para la obtencion de polimeros en perlas, reticulados, monodispersados. |
US7709174B2 (en) * | 2005-12-15 | 2010-05-04 | Ricoh Company Limited | Toner, method of preparing the toner, and developer, image forming method, image forming apparatus, and process cartridge using the toner |
US8092975B2 (en) * | 2007-06-29 | 2012-01-10 | Zeon Corporation | Method for producing toner for devoloping electrostatic image |
-
2012
- 2012-07-19 JP JP2012160281A patent/JP5631363B2/ja not_active Expired - Fee Related
- 2012-07-25 EP EP12177892.2A patent/EP2564926B1/en active Active
- 2012-08-21 US US13/590,276 patent/US8686055B2/en active Active
- 2012-08-30 CN CN2012103159006A patent/CN102964470A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
EP2564926B1 (en) | 2018-06-13 |
CN102964470A (zh) | 2013-03-13 |
US20130053460A1 (en) | 2013-02-28 |
EP2564926A1 (en) | 2013-03-06 |
JP2013053300A (ja) | 2013-03-21 |
US8686055B2 (en) | 2014-04-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5512604A (en) | Porous copolymers having a cellular polymeric structure suitable for preparing ion-exchange resins and adsorbents | |
JPS6211005B2 (ja) | ||
US4564644A (en) | Ion exchange resins prepared by sequential monomer addition | |
US5231115A (en) | Seeded porous copolymers and ion-exchange resins prepared therefrom | |
JP3261534B2 (ja) | イオン交換及び吸着共重合体の断熱製造方法 | |
JP4022399B2 (ja) | 高生産性ビスフェノール‐a触媒 | |
US5068255A (en) | Ion exchange resins prepared by sequential monomer addition | |
US6323249B1 (en) | Macroporous resins having large pores but with high crush strength | |
JP5631363B2 (ja) | 改良されたシェル官能化イオン交換樹脂 | |
JP5675654B2 (ja) | ビニル芳香族ポリマーの第三級アミンによるアミノ化 | |
US20080096987A1 (en) | Method for the Production of Monodispersed Ion Exchangers Containing Pores | |
JP4744694B2 (ja) | ゲルタイプコポリマービーズ及びそれから製造されたイオン交換樹脂 | |
JP2013053301A (ja) | シェル官能化イオン交換樹脂 | |
JP2000140652A (ja) | 単分散ゼラチン状カチオン交換体の製造方法 | |
JPH11179218A (ja) | イオン交換樹脂 | |
US20020153323A1 (en) | Process for the preparation of cation exchangers in gel form | |
EP0045824A1 (en) | Ion exchange material, its preparation and use | |
EP0168622A2 (en) | Ion exchange resins | |
JP6185663B2 (ja) | 脂肪族アミノ官能基を含む陰イオン交換樹脂及びキレート剤樹脂を作製するための方法 | |
WO2015160562A1 (en) | Sulfonation of aromatic polymers in the presence of a polyfluorinated benzene compound as swelling agent | |
JPS6159179B2 (ja) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20131024 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20131029 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140129 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140401 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140701 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140918 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20141007 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5631363 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
LAPS | Cancellation because of no payment of annual fees |