ZA200102025B - Modificaton of engineering-polymers with basic N groups and ion-exchange groups in the side chain. - Google Patents
Modificaton of engineering-polymers with basic N groups and ion-exchange groups in the side chain. Download PDFInfo
- Publication number
- ZA200102025B ZA200102025B ZA200102025A ZA200102025A ZA200102025B ZA 200102025 B ZA200102025 B ZA 200102025B ZA 200102025 A ZA200102025 A ZA 200102025A ZA 200102025 A ZA200102025 A ZA 200102025A ZA 200102025 B ZA200102025 B ZA 200102025B
- Authority
- ZA
- South Africa
- Prior art keywords
- polymers
- groups
- acid
- polymer
- basic
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims description 167
- 238000005342 ion exchange Methods 0.000 title description 13
- 239000012528 membrane Substances 0.000 claims description 70
- 238000006243 chemical reaction Methods 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 229920002492 poly(sulfone) Polymers 0.000 claims description 40
- -1 halogen alkanes Chemical class 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 27
- 238000005349 anion exchange Methods 0.000 claims description 25
- 239000005267 main chain polymer Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000011521 glass Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 10
- 230000004048 modification Effects 0.000 claims description 9
- 238000012986 modification Methods 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000000446 fuel Substances 0.000 claims description 8
- 229920005597 polymer membrane Polymers 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 150000008365 aromatic ketones Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 claims description 5
- 238000000502 dialysis Methods 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 235000011149 sulphuric acid Nutrition 0.000 claims description 5
- 239000001117 sulphuric acid Substances 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 230000009257 reactivity Effects 0.000 claims description 4
- 238000009792 diffusion process Methods 0.000 claims description 3
- 238000000909 electrodialysis Methods 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000001728 nano-filtration Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 2
- 238000005373 pervaporation Methods 0.000 claims description 2
- 239000005518 polymer electrolyte Substances 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims 5
- 229920000570 polyether Polymers 0.000 claims 5
- 239000000243 solution Substances 0.000 claims 5
- 125000001174 sulfone group Chemical group 0.000 claims 4
- 239000002759 woven fabric Substances 0.000 claims 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- 238000006011 modification reaction Methods 0.000 claims 2
- 150000003852 triazoles Chemical class 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 229920000491 Polyphenylsulfone Polymers 0.000 claims 1
- 229920003295 Radel® Polymers 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 150000005840 aryl radicals Chemical group 0.000 claims 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims 1
- 150000004651 carbonic acid esters Chemical class 0.000 claims 1
- 150000007942 carboxylates Chemical group 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 19
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- 238000006467 substitution reaction Methods 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 238000005341 cation exchange Methods 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 229920002530 polyetherether ketone Polymers 0.000 description 6
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003011 anion exchange membrane Substances 0.000 description 4
- ORBFAMHUKZLWSD-UHFFFAOYSA-N ethyl 2-(dimethylamino)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1N(C)C ORBFAMHUKZLWSD-UHFFFAOYSA-N 0.000 description 4
- MCRPKBUFXAKDKI-UHFFFAOYSA-N ethyl pyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC=C1 MCRPKBUFXAKDKI-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 208000021596 pentasomy X Diseases 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920013683 Celanese Polymers 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- 241001626506 Philypnodon Species 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229920005601 base polymer Polymers 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- QPOWUYJWCJRLEE-UHFFFAOYSA-N dipyridin-2-ylmethanone Chemical compound C=1C=CC=NC=1C(=O)C1=CC=CC=N1 QPOWUYJWCJRLEE-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920002480 polybenzimidazole Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 description 1
- 101000860173 Myxococcus xanthus C-factor Proteins 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920003060 Poly(vinyl benzyl chloride) Polymers 0.000 description 1
- 239000004693 Polybenzimidazole Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- 102000005936 beta-Galactosidase Human genes 0.000 description 1
- 108010005774 beta-Galactosidase Proteins 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003010 cation ion exchange membrane Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000001566 impedance spectroscopy Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000003014 ion exchange membrane Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920000075 poly(4-vinylpyridine) Polymers 0.000 description 1
- 229920006376 polybenzimidazole fiber Polymers 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0002—Organic membrane manufacture
- B01D67/0009—Organic membrane manufacture by phase separation, sol-gel transition, evaporation or solvent quenching
- B01D67/0011—Casting solutions therefor
- B01D67/00111—Polymer pretreatment in the casting solutions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0081—After-treatment of organic or inorganic membranes
- B01D67/0093—Chemical modification
- B01D67/00933—Chemical modification by addition of a layer chemically bonded to the membrane
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/66—Polymers having sulfur in the main chain, with or without nitrogen, oxygen or carbon only
- B01D71/68—Polysulfones; Polyethersulfones
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
- B01D71/80—Block polymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
- B01D71/82—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74 characterised by the presence of specified groups, e.g. introduced by chemical after-treatment
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- 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
- B01J41/13—Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- 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
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
- C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
- C08J5/2218—Synthetic macromolecular compounds
- C08J5/2256—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions other than those involving carbon-to-carbon bonds, e.g. obtained by polycondensation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/02—Hydrophilization
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/08—Specific temperatures applied
- B01D2323/082—Cooling
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/12—Specific ratios of components used
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/30—Cross-linking
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/36—Hydrophilic membranes
-
- 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
- C08J2381/00—Characterised by the use 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; Polysulfones; Derivatives of such polymers
- C08J2381/06—Polysulfones; Polyethersulfones
-
- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/124—Water desalination
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Polyamides (AREA)
- Polyethers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Conductive Materials (AREA)
- External Artificial Organs (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19836514A DE19836514A1 (de) | 1998-08-12 | 1998-08-12 | Modifikation von Engineeringpolymeren mit N-basischen Gruppe und mit Ionenaustauschergruppen in der Seitenkette |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200102025B true ZA200102025B (en) | 2002-02-13 |
Family
ID=7877291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200102025A ZA200102025B (en) | 1998-08-12 | 2001-03-12 | Modificaton of engineering-polymers with basic N groups and ion-exchange groups in the side chain. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6590067B2 (da) |
| EP (1) | EP1105433B1 (da) |
| JP (1) | JP2002522607A (da) |
| KR (1) | KR100649370B1 (da) |
| CN (1) | CN1293123C (da) |
| AT (1) | ATE280795T1 (da) |
| AU (2) | AU771230B2 (da) |
| BR (1) | BR9912935B1 (da) |
| CA (1) | CA2338606A1 (da) |
| DE (2) | DE19836514A1 (da) |
| DK (1) | DK1105433T3 (da) |
| ES (1) | ES2237145T3 (da) |
| IL (2) | IL141972A0 (da) |
| WO (1) | WO2000009588A1 (da) |
| ZA (1) | ZA200102025B (da) |
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| EE04023B1 (et) | 1996-10-18 | 2003-04-15 | Vertex Pharmaceuticals Incorporated | Seriinproteaaside, eriti C-hepatiidi viiruse NS3-proteaasi inhibiitorid |
| DE19836514A1 (de) | 1998-08-12 | 2000-02-17 | Univ Stuttgart | Modifikation von Engineeringpolymeren mit N-basischen Gruppe und mit Ionenaustauschergruppen in der Seitenkette |
| DE19919708A1 (de) * | 1999-04-30 | 2001-03-01 | Univ Stuttgart | Stufenweise Alkylierung von polymeren Aminen |
| DE10021106A1 (de) * | 2000-05-02 | 2001-11-08 | Univ Stuttgart | Polymere Membranen |
| DE10054233A1 (de) * | 2000-05-19 | 2002-05-08 | Univ Stuttgart Lehrstuhl Und I | Kovalent vernetzte Kompositmembranen |
| DE10024576A1 (de) * | 2000-05-19 | 2001-11-22 | Univ Stuttgart | Kovalent und ionisch vernetzte Polymere und Polymermembranen |
| DE10024575A1 (de) * | 2000-11-02 | 2001-11-22 | Univ Stuttgart | Kovalent vernetzte Polymere und Polymermembranen via Sulfinatalkylierung |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| DE10292065D2 (de) | 2001-05-11 | 2004-08-05 | Thomas Haering | Modifikation von verstreckten Folien |
| ATE339466T1 (de) | 2001-07-30 | 2006-10-15 | Asahi Glass Engineering Co Ltd | Anionenaustauscher und verfahren zur herstellung einer anionenaustauschmembran |
| AU2003223602B8 (en) | 2002-04-11 | 2010-05-27 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hepatitis C virus NS3-NS4 protease |
| DE10394072D2 (de) * | 2002-11-21 | 2005-10-13 | Thomas Haering | Modifikation von Verstreckten Folien |
| US7211203B2 (en) * | 2003-02-04 | 2007-05-01 | Honda Motor Co., Ltd. | Polymer electrolyte, proton conductive membrane and membrane-electrode assembly |
| DE10320320B4 (de) * | 2003-05-06 | 2007-08-16 | Forschungszentrum Jülich GmbH | Katalysatorschicht, geeignete Katalysatorpaste, sowie Herstellungsverfahren derselben |
| AR045596A1 (es) | 2003-09-05 | 2005-11-02 | Vertex Pharma | Inhibidores de proteasas de serina en particular proteasa ns3-ns4a del vhc |
| EP1692157B1 (en) | 2003-10-10 | 2013-04-17 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| WO2005043118A2 (en) | 2003-10-27 | 2005-05-12 | Vertex Pharmaceuticals Incorporated | Drug discovery method |
| EP1944042A1 (en) | 2003-10-27 | 2008-07-16 | Vertex Pharmceuticals Incorporated | Combinations for HCV treatment |
| AU2005212257A1 (en) | 2004-02-04 | 2005-08-25 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
| JPWO2005122277A1 (ja) * | 2004-06-10 | 2008-04-10 | コニカミノルタホールディングス株式会社 | 有機薄膜トランジスタ |
| JP2009505966A (ja) * | 2005-08-02 | 2009-02-12 | バーテックス ファーマシューティカルズ インコーポレイテッド | セリンプロテアーゼのインヒビター |
| JP5203203B2 (ja) * | 2005-08-19 | 2013-06-05 | バーテックス ファーマシューティカルズ インコーポレイテッド | 製造工程および中間体 |
| US8399615B2 (en) | 2005-08-19 | 2013-03-19 | Vertex Pharmaceuticals Incorporated | Processes and intermediates |
| US7964624B1 (en) * | 2005-08-26 | 2011-06-21 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases |
| AR055395A1 (es) | 2005-08-26 | 2007-08-22 | Vertex Pharma | Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c |
| KR20140098867A (ko) | 2005-11-11 | 2014-08-08 | 버텍스 파마슈티칼스 인코포레이티드 | Ｃ형 간염 바이러스 변이체 |
| DE102005054149A1 (de) * | 2005-11-14 | 2007-05-16 | Basf Ag | Aminhaltige Katalysatortinte für Brennstoffzellen |
| EP1984430A2 (de) | 2006-02-03 | 2008-10-29 | Universität Stuttgart - Institut für Chemische Verfahrenstechnik | Phosphonsäure-haltige blends und phosphonsäure-haltige polymere |
| EP1986769B1 (de) | 2006-02-16 | 2011-07-13 | Basf Se | Katalytisches verfahren für die phosphonylierung von hochtemperaturpolymeren |
| CN101489557B (zh) | 2006-02-27 | 2013-12-18 | 弗特克斯药品有限公司 | 包含vx-950的共晶体和包含所述共晶体的药物组合物 |
| WO2007109080A2 (en) | 2006-03-16 | 2007-09-27 | Vertex Pharmaceuticals Incorporated | Deuterated hepatitis c protease inhibitors |
| EP2134717A2 (en) * | 2007-02-27 | 2009-12-23 | Vertex Pharmceuticals Incorporated | Inhibitors of serine proteases |
| EP2463284A1 (en) * | 2007-02-27 | 2012-06-13 | Vertex Pharmceuticals Incorporated | Co-crystals and pharmaceutical compositions comprising the same |
| ES2381410T3 (es) | 2007-05-04 | 2012-05-28 | Vertex Pharmceuticals Incorporated | Terapia de combinación paa el tratamiento de infecciones por VHC |
| JP5443360B2 (ja) * | 2007-08-30 | 2014-03-19 | バーテックス ファーマシューティカルズ インコーポレイテッド | 共結晶体およびそれを含む医薬組成物 |
| JP5481880B2 (ja) * | 2008-03-10 | 2014-04-23 | 東レ株式会社 | 電解質膜の製造方法 |
| DE102009014906A1 (de) | 2008-04-01 | 2009-10-15 | Basf Se | Polymerelektrolyte basierend auf Lewis-Säure modifizierten Imidazoliumsalzen |
| US7816482B1 (en) | 2009-03-26 | 2010-10-19 | Sandia Corporation | Epoxy-crosslinked sulfonated poly (phenylene) copolymer proton exchange membranes |
| US8110636B1 (en) | 2009-04-17 | 2012-02-07 | Sandia Corporation | Multi-block sulfonated poly(phenylene) copolymer proton exchange membranes |
| JP6008870B2 (ja) * | 2010-12-12 | 2016-10-19 | ベン‐グリオン ユニバーシティ オブ ザ ネゲヴ リサーチ アンド デベロップメント オーソリティ | 陰イオン交換膜、その調製方法および用途 |
| CN102728237A (zh) * | 2012-06-20 | 2012-10-17 | 中国科学技术大学 | 均相阴离子交换膜及其制备方法 |
| US10384167B2 (en) | 2013-11-21 | 2019-08-20 | Oasys Water LLC | Systems and methods for improving performance of osmotically driven membrane systems |
| EP2902431A1 (en) * | 2014-02-04 | 2015-08-05 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Polymer blends with high ion-exchange capacity and high ion-conductivity as well as methods for preparing the same |
| US9534097B2 (en) | 2014-04-25 | 2017-01-03 | Sandia Corporation | Poly(phenylene alkylene)-based lonomers |
| US11236196B2 (en) | 2014-11-18 | 2022-02-01 | Rensselaer Polytechnic Institute | Polymers and methods for their manufacture |
| CA2968110C (en) | 2014-11-18 | 2023-10-10 | Rensselaer Polytechnic Institute | Novel polymers and methods for their manufacture |
| WO2018119020A1 (en) | 2016-12-20 | 2018-06-28 | Rensselaer Polytechnic Institute | Proton exchange membrane material and methods of making the same |
| US20200238272A1 (en) | 2017-07-06 | 2020-07-30 | Rensselaer Polytechnic Institute | Ionic functionalization of aromatic polymers for ion exchange membranes |
| CN113366680B (zh) | 2018-11-26 | 2024-06-07 | 伦斯勒理工学院 | 磷酸根阴离子-季铵离子对配位的聚合物膜 |
| CN109810254A (zh) * | 2019-01-18 | 2019-05-28 | 北京赛特超润界面科技有限公司 | 离子交联型聚醚醚酮-聚醚砜聚合物及其合成方法和薄膜及该薄膜在盐差发电中的应用 |
| CN109860701B (zh) * | 2019-02-15 | 2020-09-08 | 云南大学 | 一种用于锂离子电池的全固态电解质及其制备方法 |
| BR112022010144A2 (pt) | 2019-11-25 | 2022-09-06 | Twelve Benefit Corp | Conjunto de eletrodos de membrana para redução de cox |
| US11465139B2 (en) | 2020-03-20 | 2022-10-11 | Rensselaer Polytechnic Institute | Thermally stable hydrocarbon-based anion exchange membrane and ionomers |
| CN112510236B (zh) * | 2020-11-30 | 2022-04-15 | 中国石油大学(北京) | 质子交换膜及其制备方法和应用 |
| CN113083032B (zh) * | 2021-04-26 | 2022-10-28 | 贵州省材料产业技术研究院 | 一种荷正电共混超滤膜及其制备方法 |
| CN113231442B (zh) * | 2021-05-08 | 2022-05-24 | 南宁市城乡规划设计研究院有限公司 | 基于离子交换与交联反应的铝尾矿渣改良方法 |
| WO2024211793A2 (en) * | 2023-04-07 | 2024-10-10 | 1S1 Energy, Inc. | Conjugate acid proton exchange polymers and methods of making and using conjugate acid proton exchange polymers |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS518179A (en) | 1974-07-11 | 1976-01-22 | Daicel Ltd | Sentakutokaseikobunshimakuoyobisono seizoho |
| US4444868A (en) * | 1981-08-06 | 1984-04-24 | Agency Of Industrial Science & Technology | Photosensitive composition |
| US4598137A (en) * | 1984-11-30 | 1986-07-01 | Canadian Patents And Development Limited | Polyarylene polyethersulfone ionomers |
| CA1258736A (en) * | 1985-10-29 | 1989-08-22 | National Research Council Of Canada | Preparation of substituted polysulfones by metalation |
| GB2216134B (en) * | 1988-03-29 | 1992-08-12 | Paterson Candy Int | Membranes and methods of preparation thereof |
| EP0506611A3 (en) * | 1991-03-25 | 1993-04-21 | Ciba-Geigy Ag | Imino functional polyethers and their use |
| EP0574791B1 (de) | 1992-06-13 | 1999-12-22 | Aventis Research & Technologies GmbH & Co. KG | Polymerelektrolyt-Membran und Verfahren zu ihrer Herstellung |
| DE19632285A1 (de) * | 1996-08-09 | 1998-02-19 | Hoechst Ag | Protonenleiter mit einer Temperaturbeständigkeit in einem weiten Bereich und guten Protonenleitfähigkeiten |
| DE19836514A1 (de) | 1998-08-12 | 2000-02-17 | Univ Stuttgart | Modifikation von Engineeringpolymeren mit N-basischen Gruppe und mit Ionenaustauschergruppen in der Seitenkette |
-
1998
- 1998-08-12 DE DE19836514A patent/DE19836514A1/de not_active Withdrawn
-
1999
- 1999-08-12 CA CA002338606A patent/CA2338606A1/en not_active Abandoned
- 1999-08-12 ES ES99942843T patent/ES2237145T3/es not_active Expired - Lifetime
- 1999-08-12 KR KR1020017001830A patent/KR100649370B1/ko not_active IP Right Cessation
- 1999-08-12 IL IL14197299A patent/IL141972A0/xx active IP Right Grant
- 1999-08-12 JP JP2000565030A patent/JP2002522607A/ja active Pending
- 1999-08-12 CN CNB998095400A patent/CN1293123C/zh not_active Expired - Fee Related
- 1999-08-12 BR BRPI9912935-3A patent/BR9912935B1/pt not_active IP Right Cessation
- 1999-08-12 AU AU56212/99A patent/AU771230B2/en not_active Ceased
- 1999-08-12 DE DE59910949T patent/DE59910949D1/de not_active Expired - Lifetime
- 1999-08-12 DK DK99942843T patent/DK1105433T3/da active
- 1999-08-12 WO PCT/EP1999/005862 patent/WO2000009588A1/de active IP Right Grant
- 1999-08-12 AT AT99942843T patent/ATE280795T1/de active
- 1999-08-12 EP EP99942843A patent/EP1105433B1/de not_active Expired - Lifetime
-
2001
- 2001-02-12 US US09/780,560 patent/US6590067B2/en not_active Expired - Lifetime
- 2001-03-12 IL IL141972A patent/IL141972A/en not_active IP Right Cessation
- 2001-03-12 ZA ZA200102025A patent/ZA200102025B/en unknown
-
2004
- 2004-02-03 AU AU2004200396A patent/AU2004200396A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN1293123C (zh) | 2007-01-03 |
| ES2237145T3 (es) | 2005-07-16 |
| ATE280795T1 (de) | 2004-11-15 |
| BR9912935B1 (pt) | 2010-09-08 |
| EP1105433B1 (de) | 2004-10-27 |
| DK1105433T3 (da) | 2005-01-10 |
| BR9912935A (pt) | 2001-09-25 |
| CA2338606A1 (en) | 2000-02-24 |
| EP1105433A1 (de) | 2001-06-13 |
| WO2000009588A1 (de) | 2000-02-24 |
| KR100649370B1 (ko) | 2006-12-21 |
| JP2002522607A (ja) | 2002-07-23 |
| AU771230B2 (en) | 2004-03-18 |
| IL141972A0 (en) | 2002-03-10 |
| IL141972A (en) | 2008-06-05 |
| DE19836514A1 (de) | 2000-02-17 |
| US6590067B2 (en) | 2003-07-08 |
| AU5621299A (en) | 2000-03-06 |
| AU2004200396A1 (en) | 2004-02-26 |
| US20020045729A1 (en) | 2002-04-18 |
| CN1312833A (zh) | 2001-09-12 |
| KR20010072431A (ko) | 2001-07-31 |
| DE59910949D1 (de) | 2004-12-02 |
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