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)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Sustainable Energy (AREA)
- Electrochemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (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)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (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 (enExample) |
| EP (1) | EP2443172B1 (enExample) |
| JP (1) | JP2012530166A (enExample) |
| KR (1) | KR20120044973A (enExample) |
| CN (1) | CN102803341A (enExample) |
| BR (1) | BRPI1015994A2 (enExample) |
| MY (1) | MY160125A (enExample) |
| WO (1) | WO2010146052A1 (enExample) |
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 (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012522856A (ja) | 2009-04-03 | 2012-09-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 塩素の少ないポリビフェニルスルホン−ポリマーの製造方法 |
| EP2440597B1 (de) | 2009-06-08 | 2013-10-16 | Basf Se | Segmentierte polyarylenether-blockcopolymere |
| WO2011020823A1 (de) | 2009-08-20 | 2011-02-24 | Basf Se | Verfahren zur herstellung von halogenarmen polybiphenylsulfon-polymeren |
| US9315626B2 (en) | 2009-12-08 | 2016-04-19 | Basf Se | Process for preparing polyamides |
| 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 |
| KR20140059755A (ko) * | 2011-04-29 | 2014-05-16 | 바스프 에스이 | 술폰화된 폴리아릴에테르를 포함하는 복합 멤브레인 및 정삼투 공정에서의 이의 용도 |
| 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 |
| EP2838647A1 (en) * | 2012-04-20 | 2015-02-25 | Basf Se | Ultrafiltration membranes fabricated from sulfonated polyphenylenesulfones |
| 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 |
| EP2981566A1 (de) | 2013-04-04 | 2016-02-10 | Basf Se | Polymerisierbare lactamzusammensetzung enthaltend ein sulfoniertes polyarylsulfon |
| CN107075110A (zh) * | 2014-10-31 | 2017-08-18 | 巴斯夫欧洲公司 | 制备膜的共聚物 |
| 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 |
| EP4638602A1 (en) | 2022-12-21 | 2025-10-29 | Syensqo Specialty Polymers USA, LLC | Polymeric composition comprising a blend of poly(aryl ether sulfone) polymers suitable for manufacturing articles |
| 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 |
| DE60214166T2 (de) * | 2001-05-08 | 2007-07-12 | Ube Industries, Ltd., Ube | Polymerelektrolyt für eine brennstoffzelle des festpolymertyps und brennstoffzelle |
| AU2002355055A1 (en) * | 2001-11-29 | 2003-06-10 | Ube Industries, Ltd. | Polyelectrolyte compositions |
| 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 |
| KR20060117916A (ko) * | 2003-09-30 | 2006-11-17 | 스미또모 가가꾸 가부시끼가이샤 | 블록 공중합체 및 그 용도 |
| KR20060115886A (ko) * | 2003-11-20 | 2006-11-10 | 버지니아 테크 인터렉추얼 프라퍼티스, 인크. | 양자 교환 멤브레인용의 친수성-소수성 부분을 함유하는다중블록 공중합체 |
| 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 CN CN2010800265661A patent/CN102803341A/zh active Pending
- 2010-06-15 MY MYPI2011006041A patent/MY160125A/en unknown
- 2010-06-15 JP JP2012515462A patent/JP2012530166A/ja active Pending
- 2010-06-15 EP EP10725446.8A patent/EP2443172B1/de not_active Not-in-force
- 2010-06-15 US US13/377,979 patent/US20120083541A1/en not_active Abandoned
- 2010-06-15 KR KR1020127000999A patent/KR20120044973A/ko not_active Ceased
- 2010-06-15 BR BRPI1015994A patent/BRPI1015994A2/pt not_active IP Right Cessation
- 2010-06-15 WO PCT/EP2010/058390 patent/WO2010146052A1/de not_active Ceased
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 |
|---|---|
| JP2012530166A (ja) | 2012-11-29 |
| CN102803341A (zh) | 2012-11-28 |
| EP2443172A1 (de) | 2012-04-25 |
| EP2443172B1 (de) | 2016-09-21 |
| BRPI1015994A2 (pt) | 2016-04-19 |
| WO2010146052A1 (de) | 2010-12-23 |
| US20120083541A1 (en) | 2012-04-05 |
| 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 | |
| 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 (enExample) | ||
| 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 | |
| KR20240154069A (ko) | 적어도 이중모드의 분자량 분포를 갖는 설폰화 폴리아릴렌설폰 중합체(sp) | |
| Arnett | Synthesis and Characterization of Disulfonated Poly (Arylene Ether Sulfone) Random Copolymers as Multipurpose Membranes for Reverse Osmosis and Fuel Cell Applications | |
| WO2023161355A1 (en) | Process for the preparation of a sulfonated polyarylenesulfone polymer (sp) | |
| WO2023237365A1 (en) | Filtration membrane with improved hydrophilicity |
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 |