KR20120044973A - 방향족 폴리에테르 술폰 블록 공중합체 - Google Patents
방향족 폴리에테르 술폰 블록 공중합체 Download PDFInfo
- Publication number
- KR20120044973A KR20120044973A KR1020127000999A KR20127000999A KR20120044973A KR 20120044973 A KR20120044973 A KR 20120044973A KR 1020127000999 A KR1020127000999 A KR 1020127000999A KR 20127000999 A KR20127000999 A KR 20127000999A KR 20120044973 A KR20120044973 A KR 20120044973A
- Authority
- KR
- South Korea
- Prior art keywords
- block copolymer
- polyether sulfone
- sulfone
- aromatic
- aromatic polyether
- 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.)
- Ceased
Links
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 60
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 45
- 229920006393 polyether sulfone Polymers 0.000 title claims abstract description 38
- 239000004695 Polyether sulfone Substances 0.000 title claims abstract description 34
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 19
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 15
- 239000012528 membrane Substances 0.000 claims description 32
- 229920000642 polymer Polymers 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000000446 fuel Substances 0.000 claims description 15
- 239000005518 polymer electrolyte Substances 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 238000006277 sulfonation reaction Methods 0.000 claims description 11
- 229920012287 polyphenylene sulfone Polymers 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 238000005191 phase separation Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920000491 Polyphenylsulfone Polymers 0.000 description 6
- -1 aromatic halides Chemical class 0.000 description 6
- 125000006575 electron-withdrawing group Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- PLVUIVUKKJTSDM-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)sulfonylbenzene Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CC=C(F)C=C1 PLVUIVUKKJTSDM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- IMHDGJOMLMDPJN-UHFFFAOYSA-N dihydroxybiphenyl Natural products OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000867 polyelectrolyte Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 2
- NYKRSGJRIJJRRK-UHFFFAOYSA-N 1-chloro-2-(2-chlorophenyl)sulfonylbenzene Chemical compound ClC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1Cl NYKRSGJRIJJRRK-UHFFFAOYSA-N 0.000 description 2
- DQFSSJGXWZMREB-UHFFFAOYSA-N 1-fluoro-2-(2-fluorophenyl)sulfonylbenzene Chemical compound FC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1F DQFSSJGXWZMREB-UHFFFAOYSA-N 0.000 description 2
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 description 2
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 2
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003295 Radel® Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010612 desalination reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 2
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 2
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 2
- 239000011146 organic particle Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 150000003457 sulfones Chemical group 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- LKFIWRPOVFNPKR-UHFFFAOYSA-N (2-fluorophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC=C1F LKFIWRPOVFNPKR-UHFFFAOYSA-N 0.000 description 1
- OGTSHGYHILFRHD-UHFFFAOYSA-N (4-fluorophenyl)-phenylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC=C1 OGTSHGYHILFRHD-UHFFFAOYSA-N 0.000 description 1
- QBNABJXQGRVIRA-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)sulfonylbenzene Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)C1=CC=C(Br)C=C1 QBNABJXQGRVIRA-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 1
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
- WMASLRCNNKMRFP-UHFFFAOYSA-N 1-fluoro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(F)=C1 WMASLRCNNKMRFP-UHFFFAOYSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- AVGQIRXZUNRSAY-UHFFFAOYSA-N 1-iodo-4-(4-iodophenyl)sulfonylbenzene Chemical compound C1=CC(I)=CC=C1S(=O)(=O)C1=CC=C(I)C=C1 AVGQIRXZUNRSAY-UHFFFAOYSA-N 0.000 description 1
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical compound OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 1
- FUOFWRPHTVUUCN-UHFFFAOYSA-N 2-chloro-5-(4-chloro-3,5-dimethylphenyl)sulfonyl-1,3-dimethylbenzene Chemical compound CC1=C(Cl)C(C)=CC(S(=O)(=O)C=2C=C(C)C(Cl)=C(C)C=2)=C1 FUOFWRPHTVUUCN-UHFFFAOYSA-N 0.000 description 1
- IXUNOARWYRWIAB-UHFFFAOYSA-N 2-fluoro-5-(4-fluoro-3,5-dimethylphenyl)sulfonyl-1,3-dimethylbenzene Chemical compound CC1=C(F)C(C)=CC(S(=O)(=O)C=2C=C(C)C(F)=C(C)C=2)=C1 IXUNOARWYRWIAB-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- QIOCFZAEFQTCSO-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C=2C=C(C)C(O)=C(C)C=2)(C(F)(F)F)C(F)(F)F)=C1 QIOCFZAEFQTCSO-UHFFFAOYSA-N 0.000 description 1
- YMSALPCDWZMQQG-UHFFFAOYSA-N 4-[2-(2,4-dihydroxyphenyl)propan-2-yl]benzene-1,3-diol Chemical compound C=1C=C(O)C=C(O)C=1C(C)(C)C1=CC=C(O)C=C1O YMSALPCDWZMQQG-UHFFFAOYSA-N 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- DZXRPCNJQDADRH-UHFFFAOYSA-N 4-chloro-1-(4-chloro-2-methylphenyl)sulfonyl-2-methylbenzene Chemical compound CC1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1C DZXRPCNJQDADRH-UHFFFAOYSA-N 0.000 description 1
- WQRGKOPKPSFHHP-UHFFFAOYSA-N 4-fluoro-1-(4-fluoro-2-methylphenyl)sulfonyl-2-methylbenzene Chemical compound CC1=CC(F)=CC=C1S(=O)(=O)C1=CC=C(F)C=C1C WQRGKOPKPSFHHP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012510 hollow fiber Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- NJBFOOCLYDNZJN-UHFFFAOYSA-N pipobroman Chemical compound BrCCC(=O)N1CCN(C(=O)CCBr)CC1 NJBFOOCLYDNZJN-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000110 poly(aryl ether sulfone) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920005649 polyetherethersulfone Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
- C08G75/23—Polyethersulfones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/06—Polysulfones; Polyethersulfones
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/02—Details
- H01M8/0202—Collectors; Separators, e.g. bipolar separators; Interconnectors
- H01M8/0204—Non-porous and characterised by the material
- H01M8/0221—Organic resins; Organic polymers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/02—Details
- H01M8/0289—Means for holding the electrolyte
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- H01M8/1032—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having sulfur, e.g. sulfonated-polyethersulfones [S-PES]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Sustainable Energy (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Fuel Cell (AREA)
- Polyethers (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09162858 | 2009-06-16 | ||
| EP09162858.6 | 2009-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20120044973A true KR20120044973A (ko) | 2012-05-08 |
Family
ID=43047745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127000999A Ceased KR20120044973A (ko) | 2009-06-16 | 2010-06-15 | 방향족 폴리에테르 술폰 블록 공중합체 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20120083541A1 (https=) |
| EP (1) | EP2443172B1 (https=) |
| JP (1) | JP2012530166A (https=) |
| KR (1) | KR20120044973A (https=) |
| CN (1) | CN102803341A (https=) |
| BR (1) | BRPI1015994A2 (https=) |
| MY (1) | MY160125A (https=) |
| WO (1) | WO2010146052A1 (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014181931A1 (ko) * | 2013-05-07 | 2014-11-13 | 제일모직 주식회사 | 술폰계 블록 공중합체 및 그 제조방법 |
| WO2015037967A1 (ko) * | 2013-09-16 | 2015-03-19 | 주식회사 엘지화학 | 이온 교환성 고분자 층을 포함하는 수처리 분리막 및 그 제조 방법 |
| KR20150032212A (ko) * | 2013-09-16 | 2015-03-25 | 주식회사 엘지화학 | 이온 교환성 고분자 층을 포함하는 수처리 분리막 및 그 제조 방법 |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2414430B2 (de) | 2009-04-03 | 2023-09-13 | Basf Se | Verfahren zur herstellung von chlorarmen polybiphenylsulfon-polymeren |
| CN102459409B (zh) | 2009-06-08 | 2014-05-28 | 巴斯夫欧洲公司 | 链段状聚亚芳基醚嵌段共聚物 |
| BR112012003468A2 (pt) | 2009-08-20 | 2016-03-01 | Basf Se | processo para a produção de polímeros de polibifenilsulfona, polímero de polibifenilsulfona, composição termoplástica para moldagem, corpo moldado, fibra, filme, membrana ou espuma, e, uso das composições termoplásticas para moldagem ou dos polímeros de polibifenilsulfona. |
| ES2639062T3 (es) | 2009-12-08 | 2017-10-25 | Basf Se | Proceso para la preparación de poliamidas |
| EP2336220A1 (de) | 2009-12-17 | 2011-06-22 | Basf Se | Verbesserte Blends aus Polyarylenethern und Polyarylensulfiden |
| US8703862B2 (en) | 2010-05-26 | 2014-04-22 | Basf Se | Reinforced thermoplastic molding compositions based on polyarylene ethers |
| US9193611B2 (en) | 2011-04-29 | 2015-11-24 | Basf Se | Composite membranes comprising a sulfonated polyarylether and their use in forward osmosis processes |
| EP2701831B1 (en) * | 2011-04-29 | 2015-10-07 | Basf Se | Composite membranes comprising a sulfonated polyarylether and their use in forward osmosis processes |
| US9296872B2 (en) | 2011-05-18 | 2016-03-29 | Basf Se | Thermoplastic molding composition made of polyarylene ethers and polyphenylene sulfide with improved processing stability |
| EP2532700A1 (en) * | 2011-06-06 | 2012-12-12 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Novel block copolymers comprising sulfonated poly(sulfones) with high ion-exchange capacity, high ion-conductivity and high stability |
| KR20150023277A (ko) * | 2012-04-20 | 2015-03-05 | 바스프 에스이 | 술폰화된 폴리페닐렌술폰으로부터 제조된 한외여과막 |
| EP2674211A1 (en) | 2012-06-14 | 2013-12-18 | Basf Se | Composite membranes comprising a sulfonated polyphenylenesulfone and their use in forward osmosis processes |
| US9045598B2 (en) | 2012-09-03 | 2015-06-02 | Basf Se | Process for producing aromatic polyether sulfones |
| CN103936991A (zh) * | 2013-01-22 | 2014-07-23 | 曹曙光 | 至少含一个亲水嵌段组分的共聚物聚电解质及合成方法 |
| CN103936990A (zh) * | 2013-01-22 | 2014-07-23 | 曹曙光 | 至少含一个憎水嵌段组分的共聚物聚电解质及合成方法 |
| CN105263988A (zh) | 2013-04-04 | 2016-01-20 | 巴斯夫欧洲公司 | 包含磺化聚芳砜的可聚合的内酰胺组合物 |
| WO2016066661A1 (en) * | 2014-10-31 | 2016-05-06 | Basf Se | Copolymers for making membranes |
| US9521515B2 (en) | 2015-01-26 | 2016-12-13 | Mobli Technologies 2010 Ltd. | Content request by location |
| WO2017148850A1 (en) * | 2016-02-29 | 2017-09-08 | Basf Se | Method for the preparation of a membrane which comprises an organic polymer of intrinsic microporosity (pim) and a sulfonated polyarylenesulfone polymer |
| CN109692582B (zh) * | 2017-10-20 | 2021-08-03 | 中国石油化工股份有限公司 | 反渗透膜及其制备方法和应用 |
| KR20250126028A (ko) | 2022-12-21 | 2025-08-22 | 솔베이 스페셜티 폴리머즈 유에스에이, 엘.엘.씨. | 물품의 제조에 적합한 폴리(아릴 에테르 설폰) 중합체의 블렌드를 포함하는 중합체 조성물 |
| WO2026070870A1 (ja) * | 2024-09-27 | 2026-04-02 | 東ソー株式会社 | 電解質膜及びその製造方法、触媒層付き電解質膜、膜電極接合体、固体高分子形燃料電池、並びに、固体高分子形水電解装置 |
| WO2026070867A1 (ja) * | 2024-09-27 | 2026-04-02 | 東ソー株式会社 | 電解質膜及びその製造方法、触媒層付き電解質膜、膜電極接合体、固体高分子形燃料電池、並びに、固体高分子形水電解装置 |
| JP7838719B1 (ja) * | 2024-09-27 | 2026-04-01 | 東ソー株式会社 | 電解質膜及びその製造方法、触媒層付き電解質膜、膜電極接合体、固体高分子形燃料電池、並びに、固体高分子形水電解装置 |
| JP7838720B1 (ja) * | 2024-09-27 | 2026-04-01 | 東ソー株式会社 | 電解質膜及びその製造方法、触媒層付き電解質膜、膜電極接合体、固体高分子形燃料電池、並びに、固体高分子形水電解装置 |
| CN119912847B (zh) * | 2025-04-02 | 2025-07-04 | 万华化学集团股份有限公司 | 一种复合涂层及其应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008894B1 (en) * | 1978-09-05 | 1983-02-23 | Imperial Chemical Industries Plc | Sulphonated polyarylethersulphone copolymers and process for the manufacture thereof |
| JP3724064B2 (ja) * | 1996-06-28 | 2005-12-07 | 住友化学株式会社 | 燃料電池用高分子電解質及び燃料電池 |
| JP4802354B2 (ja) * | 1999-12-27 | 2011-10-26 | 住友化学株式会社 | 高分子電解質およびその製造方法 |
| DE10007272B4 (de) * | 2000-02-17 | 2005-04-07 | Membrana Gmbh | Blockcopolymere mit sulfonierten Polyethersulfoneinheiten |
| ATE337618T1 (de) * | 2001-05-08 | 2006-09-15 | Ube Industries | Polymerelektrolyt für eine brennstoffzelle des festpolymertyps und brennstoffzelle |
| WO2003046080A1 (fr) * | 2001-11-29 | 2003-06-05 | Ube Industries, Ltd. | Compositions polyelectrolytiques |
| ATE550368T1 (de) * | 2003-09-30 | 2012-04-15 | Sumitomo Chemical Co | Blockcopolymer und seine verwendung |
| JP4375170B2 (ja) * | 2003-09-30 | 2009-12-02 | 住友化学株式会社 | ブロック共重合体及びその用途 |
| EP1687377A4 (en) * | 2003-11-20 | 2009-05-06 | Virginia Tech Intell Prop | MULTIPLOCK COPOLYMERS WITH HYDROPHIL HYDROPHOBIC SEGMENTS FOR PROTONATE EXCHANGE MEMBRANES |
| JP5071609B2 (ja) * | 2004-06-01 | 2012-11-14 | 宇部興産株式会社 | 固体高分子型燃料電池用高分子電解質膜 |
| JP4807007B2 (ja) * | 2005-08-25 | 2011-11-02 | 宇部興産株式会社 | 高分子電解質組成物およびその用途 |
-
2010
- 2010-06-15 EP EP10725446.8A patent/EP2443172B1/de not_active Not-in-force
- 2010-06-15 BR BRPI1015994A patent/BRPI1015994A2/pt not_active IP Right Cessation
- 2010-06-15 JP JP2012515462A patent/JP2012530166A/ja active Pending
- 2010-06-15 US US13/377,979 patent/US20120083541A1/en not_active Abandoned
- 2010-06-15 WO PCT/EP2010/058390 patent/WO2010146052A1/de not_active Ceased
- 2010-06-15 MY MYPI2011006041A patent/MY160125A/en unknown
- 2010-06-15 KR KR1020127000999A patent/KR20120044973A/ko not_active Ceased
- 2010-06-15 CN CN2010800265661A patent/CN102803341A/zh active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014181931A1 (ko) * | 2013-05-07 | 2014-11-13 | 제일모직 주식회사 | 술폰계 블록 공중합체 및 그 제조방법 |
| WO2015037967A1 (ko) * | 2013-09-16 | 2015-03-19 | 주식회사 엘지화학 | 이온 교환성 고분자 층을 포함하는 수처리 분리막 및 그 제조 방법 |
| KR20150032212A (ko) * | 2013-09-16 | 2015-03-25 | 주식회사 엘지화학 | 이온 교환성 고분자 층을 포함하는 수처리 분리막 및 그 제조 방법 |
| CN105705221A (zh) * | 2013-09-16 | 2016-06-22 | 株式会社Lg化学 | 包含可离子交换聚合物层的水处理分离膜及其形成方法 |
| US10279320B2 (en) | 2013-09-16 | 2019-05-07 | Lg Chem, Ltd. | Water-treatment separation membrane comprising ionic exchangeable polymer layer and method for forming same |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2443172A1 (de) | 2012-04-25 |
| JP2012530166A (ja) | 2012-11-29 |
| WO2010146052A1 (de) | 2010-12-23 |
| CN102803341A (zh) | 2012-11-28 |
| US20120083541A1 (en) | 2012-04-05 |
| EP2443172B1 (de) | 2016-09-21 |
| BRPI1015994A2 (pt) | 2016-04-19 |
| MY160125A (en) | 2017-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20120083541A1 (en) | Aromatic polyether sulfone block copolymers | |
| JP5209165B2 (ja) | 複合イオン交換材料 | |
| JP3969077B2 (ja) | 高分子電解質及びその製造方法 | |
| US8163864B2 (en) | Sulfonated polyarylene compounds, membrane material made therefrom, method for the production thereof and use | |
| JP2003031232A (ja) | 固体高分子型燃料電池用高分子電解質及び燃料電池 | |
| CN102634008A (zh) | 高分子电解质材料、高分子电解质成型体、膜电极复合体和固体高分子型燃料电池 | |
| KR20090053499A (ko) | 측쇄에 산성기를 갖는 양성자 전도성 고분자 단량체, 상기단량체로 제조된 양성자 전도성 고분자, 상기 양성자전도성 고분자의 제조 방법, 상기 양성자 전도성 고분자를포함하는 전해질막 및 상기 전해질막을 채용한 막-전극접합체 | |
| JP4161249B2 (ja) | イオン伝導性芳香族ポリエーテル | |
| KR20150036007A (ko) | 술폰화 폴리페닐렌술폰을 포함하는 복합 멤브레인 및 이의 정삼투 공정에서의 용도 | |
| JP2008521999A5 (https=) | ||
| JP2008521999A (ja) | スルホン化マルチブロック共重合体及びこれを用いた電解質膜 | |
| CN1922241B (zh) | 高分子电解质及其用途 | |
| JP5202783B2 (ja) | イオン交換材料 | |
| WO2007075540A2 (en) | Sulfonated polyaryletherketone-polyethersulfone block copolymers | |
| KR20150011814A (ko) | 양으로 하전된 고성능 복합재료막 및 나노여과 공정에서 이의 용도 | |
| JP2004190003A (ja) | ブロック共重合体およびその用途 | |
| CA2454698C (en) | Ion-conducting polymeric materials | |
| KR101651093B1 (ko) | 다중황산기를 포함하는 다중페닐 단위체를 지닌 양이온 교환 고분자 | |
| JP2007039525A (ja) | イオン交換膜、イオン交換樹脂、その製造方法およびイオン交換樹脂の精製方法 | |
| KR101286265B1 (ko) | 술폰화 폴리술폰케톤 공중합체, 이를 포함하는 고분자전해질, 및 이의 제조방법 | |
| JP2007329120A (ja) | 芳香族炭化水素系イオン伝導性高分子電解質，電解質膜，及びその製造方法 | |
| JP2025510537A (ja) | スルホン化ポリアリーレンスルホンポリマー（ｓＰ）を含有するメンブレン（Ｍ）の製造方法 | |
| Arnett | Synthesis and Characterization of Disulfonated Poly (Arylene Ether Sulfone) Random Copolymers as Multipurpose Membranes for Reverse Osmosis and Fuel Cell Applications | |
| KR20240154069A (ko) | 적어도 이중모드의 분자량 분포를 갖는 설폰화 폴리아릴렌설폰 중합체(sp) | |
| WO2026074001A1 (en) | Method for the preparation of a catalyst coated membrane (ccm) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20120113 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20150615 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20160708 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20161019 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20160708 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |