CA2379962C - Polymeres et membranes polymere reticules de facon covalente par alkylation de sulfinate - Google Patents

Polymeres et membranes polymere reticules de facon covalente par alkylation de sulfinate Download PDF

Info

Publication number: CA2379962C
Authority: CA; Canada
Prior art keywords: polymer; groups; polymer blend; membrane; cross
Prior art date: 2000-05-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA2379962A

Other languages

English (en)

Other versions

CA2379962A1 (fr

Inventor

Jochen Kerres

Wei Zhang

Chy-Ming Tang

Thomas Haring

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Institut fuer Chemische Verfahrenstechnik Universitaet Stuttgart

Original Assignee

Institut fuer Chemische Verfahrenstechnik Universitaet Stuttgart

Priority date (The priority date 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 date listed.)

2000-05-19

Filing date

2001-05-21

Publication date

2016-10-18

2000-05-19 Priority claimed from DE10024575A external-priority patent/DE10024575A1/de

2001-05-21 Application filed by Institut fuer Chemische Verfahrenstechnik Universitaet Stuttgart filed Critical Institut fuer Chemische Verfahrenstechnik Universitaet Stuttgart

2002-01-03 Publication of CA2379962A1 publication Critical patent/CA2379962A1/fr

2016-10-18 Application granted granted Critical

2016-10-18 Publication of CA2379962C publication Critical patent/CA2379962C/fr

2021-05-21 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

229920006037 cross link polymer Polymers 0.000 title claims abstract description 32
229920005597 polymer membrane Polymers 0.000 title claims abstract description 16
DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 title description 12
238000005804 alkylation reaction Methods 0.000 title description 4
230000029936 alkylation Effects 0.000 title description 3
229920000642 polymer Polymers 0.000 claims abstract description 93
229920002959 polymer blend Polymers 0.000 claims abstract description 43
238000004132 cross linking Methods 0.000 claims abstract description 27
125000000524 functional group Chemical group 0.000 claims abstract description 18
238000005341 cation exchange Methods 0.000 claims abstract description 15
239000002243 precursor Substances 0.000 claims abstract description 14
-1 ammonium ions Chemical class 0.000 claims abstract description 11
150000001768 cations Chemical class 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 10
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 10
229910052794 bromium Inorganic materials 0.000 claims abstract description 9
229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
229910052740 iodine Inorganic materials 0.000 claims abstract description 8
229910052751 metal Inorganic materials 0.000 claims abstract description 8
239000002184 metal Substances 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
229910052700 potassium Inorganic materials 0.000 claims abstract description 6
229910052708 sodium Inorganic materials 0.000 claims abstract description 6
229910052792 caesium Inorganic materials 0.000 claims abstract description 5
229910052744 lithium Inorganic materials 0.000 claims abstract description 5
101100275854 Arabidopsis thaliana CSI1 gene Proteins 0.000 claims abstract description 4
150000001350 alkyl halides Chemical class 0.000 claims abstract description 4
150000002894 organic compounds Chemical class 0.000 claims abstract description 4
239000012528 membrane Substances 0.000 claims description 77
229910052615 phyllosilicate Inorganic materials 0.000 claims description 41
239000000203 mixture Substances 0.000 claims description 33
229910052645 tectosilicate Inorganic materials 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 15
239000000975 dye Substances 0.000 claims description 15
239000003431 cross linking reagent Substances 0.000 claims description 14
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
239000011521 glass Substances 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
239000000446 fuel Substances 0.000 claims description 8
229920006254 polymer film Polymers 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
238000003756 stirring Methods 0.000 claims description 6
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 5
239000002585 base Substances 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
239000010409 thin film Substances 0.000 claims description 5
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
239000000010 aprotic solvent Substances 0.000 claims description 4
229910052799 carbon Chemical group 0.000 claims description 4
239000007789 gas Substances 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
238000000926 separation method Methods 0.000 claims description 4
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
229910019142 PO4 Inorganic materials 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000010452 phosphate Substances 0.000 claims description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
150000007942 carboxylates Chemical class 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
125000000542 sulfonic acid group Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
229920005601 base polymer Polymers 0.000 claims 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
229920002492 poly(sulfone) Polymers 0.000 claims 2
229920001955 polyphenylene ether Polymers 0.000 claims 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical group ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
239000004696 Poly ether ether ketone Substances 0.000 claims 1
239000004734 Polyphenylene sulfide Substances 0.000 claims 1
229920000491 Polyphenylsulfone Polymers 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
125000002843 carboxylic acid group Chemical group 0.000 claims 1
229920001577 copolymer Polymers 0.000 claims 1
238000000502 dialysis Methods 0.000 claims 1
238000009792 diffusion process Methods 0.000 claims 1
238000000909 electrodialysis Methods 0.000 claims 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
239000004745 nonwoven fabric Substances 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
238000005373 pervaporation Methods 0.000 claims 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
229920001643 poly(ether ketone) Polymers 0.000 claims 1
229920006393 polyether sulfone Polymers 0.000 claims 1
229920002530 polyetherether ketone Polymers 0.000 claims 1
229920005649 polyetherethersulfone Polymers 0.000 claims 1
229920000069 polyphenylene sulfide Polymers 0.000 claims 1
238000001223 reverse osmosis Methods 0.000 claims 1
239000002759 woven fabric Substances 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 description 14
150000002500 ions Chemical class 0.000 description 11
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
239000002131 composite material Substances 0.000 description 6
239000010408 film Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000010410 layer Substances 0.000 description 5
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
238000005342 ion exchange Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
229920001940 conductive polymer Polymers 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
229910021645 metal ion Inorganic materials 0.000 description 3
229910052901 montmorillonite Inorganic materials 0.000 description 3
150000004760 silicates Chemical class 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000002152 alkylating effect Effects 0.000 description 2
235000012216 bentonite Nutrition 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
229920000554 ionomer Polymers 0.000 description 2
230000011987 methylation Effects 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
229940124530 sulfonamide Drugs 0.000 description 2
150000003456 sulfonamides Chemical class 0.000 description 2
230000008961 swelling Effects 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
238000001291 vacuum drying Methods 0.000 description 2
IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 description 2
MBEVSMZJMIQVBG-UHFFFAOYSA-N 2-(hydroxymethyl)guanidine Chemical class NC(N)=NCO MBEVSMZJMIQVBG-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
101100243951 Caenorhabditis elegans pie-1 gene Proteins 0.000 description 1
241000861718 Chloris <Aves> Species 0.000 description 1
206010011416 Croup infectious Diseases 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000004113 Sepiolite Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 1
229910001588 amesite Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000005349 anion exchange Methods 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
201000010549 croup Diseases 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000032798 delamination Effects 0.000 description 1
230000002542 deteriorative effect Effects 0.000 description 1
125000004427 diamine group Chemical group 0.000 description 1
CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
YGANSGVIUGARFR-UHFFFAOYSA-N dipotassium dioxosilane oxo(oxoalumanyloxy)alumane oxygen(2-) Chemical compound [O--].[K+].[K+].O=[Si]=O.O=[Al]O[Al]=O YGANSGVIUGARFR-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000007306 functionalization reaction Methods 0.000 description 1
229910052621 halloysite Inorganic materials 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229910000271 hectorite Inorganic materials 0.000 description 1
KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910052900 illite Inorganic materials 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000011256 inorganic filler Substances 0.000 description 1
229910003475 inorganic filler Inorganic materials 0.000 description 1
229910052909 inorganic silicate Inorganic materials 0.000 description 1
238000009830 intercalation Methods 0.000 description 1
230000002687 intercalation Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
229910052627 muscovite Inorganic materials 0.000 description 1
VGIBGUSAECPPNB-UHFFFAOYSA-L nonaaluminum;magnesium;tripotassium;1,3-dioxido-2,4,5-trioxa-1,3-disilabicyclo[1.1.1]pentane;iron(2+);oxygen(2-);fluoride;hydroxide Chemical compound [OH-].[O-2].[O-2].[O-2].[O-2].[O-2].[F-].[Mg+2].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[K+].[K+].[K+].[Fe+2].O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2 VGIBGUSAECPPNB-UHFFFAOYSA-L 0.000 description 1
229910000273 nontronite Inorganic materials 0.000 description 1
VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000003252 repetitive effect Effects 0.000 description 1
229910000275 saponite Inorganic materials 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
239000002356 single layer Substances 0.000 description 1
229910021647 smectite Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
229910000166 zirconium phosphate Inorganic materials 0.000 description 1
LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1

Classifications

- 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
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
- B01D53/228—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion characterised by specific membranes
- 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
- B01D71/52—Polyethers
- B01D71/522—Aromatic polyethers
- B01D71/5222—Polyetherketone, polyetheretherketone, or polyaryletherketone
- 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
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- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/409—Separators, membranes or diaphragms characterised by the material
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- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
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- 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]
- H—ELECTRICITY
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- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
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- H01M8/1044—Mixtures of polymers, of which at least one is ionically conductive
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- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
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- H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
- H01M8/1072—Polymeric electrolyte materials characterised by the manufacturing processes by chemical reactions, e.g. in situ polymerisation or in situ crosslinking
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
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- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
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- H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
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- H—ELECTRICITY
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- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
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- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
- H01M8/1086—After-treatment of the membrane other than by polymerisation
- 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
- H—ELECTRICITY
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- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0065—Solid electrolytes
- H01M2300/0082—Organic polymers
- 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
- Y02E60/10—Energy storage using batteries
- 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
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

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Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Manufacturing & Machinery (AREA)
General Chemical & Material Sciences (AREA)
Electrochemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Sustainable Development (AREA)
Sustainable Energy (AREA)
Inorganic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Dispersion Chemistry (AREA)
Organic Chemistry (AREA)
General Physics & Mathematics (AREA)
Medicinal Chemistry (AREA)
Health & Medical Sciences (AREA)
Analytical Chemistry (AREA)
Oil, Petroleum & Natural Gas (AREA)
Composite Materials (AREA)
Physics & Mathematics (AREA)
Condensed Matter Physics & Semiconductors (AREA)
Polymers & Plastics (AREA)
Manufacture Of Macromolecular Shaped Articles (AREA)
Separation Using Semi-Permeable Membranes (AREA)
Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Compositions Of Macromolecular Compounds (AREA)
Fuel Cell (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Secondary Cells (AREA)

CA2379962A 2000-05-19 2001-05-21 Polymeres et membranes polymere reticules de facon covalente par alkylation de sulfinate Expired - Lifetime CA2379962C (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
DE10024575A DE10024575A1 (de)	2000-11-02	2000-05-19	Kovalent vernetzte Polymere und Polymermembranen via Sulfinatalkylierung
DE10024575.7		2000-05-19
DE10054233A DE10054233A1 (de)	2000-05-19	2000-11-02	Kovalent vernetzte Kompositmembranen
DE10054233.6		2000-11-02
PCT/EP2001/005826 WO2002000773A2 (fr)	2000-05-19	2001-05-21	Polymeres et membranes polymere reticules de façon covalente par alkylation de sulfinate

Publications (2)

Publication Number	Publication Date
CA2379962A1 CA2379962A1 (fr)	2002-01-03
CA2379962C true CA2379962C (fr)	2016-10-18

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CA2379962A Expired - Lifetime CA2379962C (fr)	2000-05-19	2001-05-21	Polymeres et membranes polymere reticules de facon covalente par alkylation de sulfinate

Country Status (9)

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EP (1)	EP1290069A2 (fr)
JP (1)	JP2004502008A (fr)
CN (1)	CN100354344C (fr)
AU (2)	AU784360B2 (fr)
BR (1)	BR0106652A (fr)
CA (1)	CA2379962C (fr)
DE (1)	DE10054233A1 (fr)
IL (1)	IL147726A0 (fr)
WO (1)	WO2002000773A2 (fr)

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Publication number	Priority date	Publication date	Assignee	Title
DE10024575A1 (de) *	2000-11-02	2001-11-22	Univ Stuttgart	Kovalent vernetzte Polymere und Polymermembranen via Sulfinatalkylierung
DE10295737B4 (de) *	2001-05-21	2018-05-09	Thomas Häring	Kovalent vernetzter Komposit, kovalente vernetzte Kompositmembran, Verfahren zu deren Herstellung und Verwendung der Membranen
KR100403754B1 (ko) *	2001-06-19	2003-10-30	송민규	연료전지용 복합 고분자 전해질 막, 이의 제조방법 및이를 포함하는 연료전지
DE10209784A1 (de) *	2001-09-01	2003-12-04	Univ Stuttgart Inst Fuer Chemi	Sulfinatgruppen enthaltende Oligomere und Polymere und Verfahren zu ihrer Herstellung
DE10391005D2 (de) *	2002-02-28	2005-04-14	Thomas Haering	Schichtstrukturen und Verfahren zu deren Herstellung
CN1649943B (zh) *	2002-02-28	2011-03-02	斯图加特大学	改性聚合物或聚合物共混物或混合膜或成型体、其制备方法和应用
JP4827044B2 (ja) *	2002-02-28	2011-11-30	ウニヴェルズィテートシュトゥットガルト	スルフィナート基を含むオリゴマー及びポリマー、並びにその製造方法
KR100486728B1 (ko)	2002-12-12	2005-05-03	삼성에스디아이 주식회사	나노복합전해질막 및 이를 채용한 연료전지
WO2005090480A1 (fr) *	2004-03-23	2005-09-29	Mitsubishi Gas Chemical Co., Inc.	Polyélectrolyte solide, film de gel polymère solide, film polyélectrolytique, et pile à combustible.
JP6016019B2 (ja) *	2012-10-30	2016-10-26	独立行政法人国立高等専門学校機構	燃料電池用の電解質膜、燃料電池用の電解質膜の製造方法および燃料電池
CN108258170B (zh) *	2017-12-05	2021-07-16	宜宾天原集团股份有限公司	一种聚醚醚酮基锂电池隔膜的制备方法
CN109659601B (zh) *	2018-12-12	2021-09-28	南京师范大学	一种多酸/高分子聚合物杂化纳米线材料作为固态电解质的应用
PL3772129T3 (pl)	2019-07-31	2021-09-27	Innolith Technology AG	Elektrolit na bazie so2 do ogniwa akumulatorowego umożliwiającego wielokrotne ładowanie i zawierające ten elektrolit ogniwo akumulatorowe umożliwiające wielokrotne ładowanie
CN115646223B (zh) *	2022-10-19	2023-06-27	安徽省海徽化工有限公司	一种耐污染聚醚砜超滤膜

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DE59309908D1 (de) *	1992-06-13	2000-01-27	Aventis Res & Tech Gmbh & Co	Polymerelektrolyt-Membran und Verfahren zu ihrer Herstellung
FR2695131B1 (fr) *	1992-09-01	1994-09-30	Alsthom Cge Alcatel	Electrolyte solide polymère conducteur protonique.
DE19622337C1 (de) *	1996-06-04	1998-03-12	Dlr Deutsche Forschungsanstalt	Vernetzung von modifizierten Engineering Thermoplasten
US6620546B1 (en) *	1997-12-01	2003-09-16	Acep Inc.	Materials for use as electrolytic solutes
JP4782903B2 (ja) *	1998-02-03	2011-09-28	エイシーイーピーインコーポレイテッド	電解溶質として有用な新規な物質
DE19836514A1 (de) *	1998-08-12	2000-02-17	Univ Stuttgart	Modifikation von Engineeringpolymeren mit N-basischen Gruppe und mit Ionenaustauschergruppen in der Seitenkette
US6828353B1 (en) *	1998-09-11	2004-12-07	Victrex Manufacturing Limited	Ion-exchange polymers
DE19919708A1 (de) *	1999-04-30	2001-03-01	Univ Stuttgart	Stufenweise Alkylierung von polymeren Aminen
DE10024576A1 (de) *	2000-05-19	2001-11-22	Univ Stuttgart	Kovalent und ionisch vernetzte Polymere und Polymermembranen

2000
- 2000-11-02 DE DE10054233A patent/DE10054233A1/de not_active Withdrawn
2001
- 2001-05-21 IL IL14772601A patent/IL147726A0/xx unknown
- 2001-05-21 AU AU93695/01A patent/AU784360B2/en not_active Ceased
- 2001-05-21 BR BR0106652-8A patent/BR0106652A/pt not_active IP Right Cessation
- 2001-05-21 CN CNB018018637A patent/CN100354344C/zh not_active Expired - Fee Related
- 2001-05-21 EP EP01974075A patent/EP1290069A2/fr not_active Withdrawn
- 2001-05-21 JP JP2002505894A patent/JP2004502008A/ja active Pending
- 2001-05-21 CA CA2379962A patent/CA2379962C/fr not_active Expired - Lifetime
- 2001-05-21 WO PCT/EP2001/005826 patent/WO2002000773A2/fr not_active Ceased
2006
- 2006-06-17 AU AU2006202592A patent/AU2006202592A1/en not_active Abandoned

Also Published As

Publication number	Publication date
WO2002000773A9 (fr)	2003-02-13
DE10054233A1 (de)	2002-05-08
EP1290069A2 (fr)	2003-03-12
CN1440438A (zh)	2003-09-03
IL147726A0 (en)	2002-08-14
AU2006202592A1 (en)	2006-07-13
JP2004502008A (ja)	2004-01-22
CA2379962A1 (fr)	2002-01-03
WO2002000773A2 (fr)	2002-01-03
CN100354344C (zh)	2007-12-12
AU9369501A (en)	2002-01-08
BR0106652A (pt)	2002-04-09
AU784360B2 (en)	2006-03-16
WO2002000773A3 (fr)	2002-07-18

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2006-05-23	EEER	Examination request
2021-07-25	MKEX	Expiry	Effective date: 20210521

Publication	Publication Date	Title
US6982303B2 (en)	2006-01-03	Covalently cross-linked polymers and polymer membranes via sulfinate alkylation
CA2379962C (fr)	2016-10-18	Polymeres et membranes polymere reticules de facon covalente par alkylation de sulfinate
AU780722B2 (en)	2005-04-14	Composites and composite membranes
US9126147B2 (en)	2015-09-08	Modification of drawn film
US7132496B2 (en)	2006-11-07	Step-by-step alkylation of polymeric amines
JP2004530020A5 (fr)	2007-09-13
EP1587859A1 (fr)	2005-10-26	Oligomeres et polymeres contenant des groupes sulfinate et procedes pour les preparer
JP5937856B2 (ja)	2016-06-22	スルフィナートアルキル化を介した共有結合架橋ポリマーおよびポリマー膜
DE10295737B4 (de)	2018-05-09	Kovalent vernetzter Komposit, kovalente vernetzte Kompositmembran, Verfahren zu deren Herstellung und Verwendung der Membranen
AU2005201750A1 (en)	2005-05-19	Step-by-step alkylation of polymeric Amines New Title: Crosslinked Acid-Base Membranes