IL46177A - Process for preparing a complex polyelectrolyte from two types of polymer and product obtained thereby - Google Patents
Process for preparing a complex polyelectrolyte from two types of polymer and product obtained therebyInfo
- Publication number
- IL46177A IL46177A IL46177A IL4617774A IL46177A IL 46177 A IL46177 A IL 46177A IL 46177 A IL46177 A IL 46177A IL 4617774 A IL4617774 A IL 4617774A IL 46177 A IL46177 A IL 46177A
- Authority
- IL
- Israel
- Prior art keywords
- polymer
- groups
- process according
- solution
- polymers
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims description 109
- 229920000867 polyelectrolyte Polymers 0.000 title claims description 37
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 22
- 239000012528 membrane Substances 0.000 claims description 20
- 239000000843 powder Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 15
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 11
- 239000002245 particle Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- -1 amine salts Chemical class 0.000 description 38
- 150000003254 radicals Chemical class 0.000 description 37
- 239000000243 solution Substances 0.000 description 36
- 239000002253 acid Substances 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003792 electrolyte Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000003010 ionic group Chemical group 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 238000000108 ultra-filtration Methods 0.000 description 4
- 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 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229920000447 polyanionic polymer Polymers 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- SMFDSFRYWRBNSQ-UHFFFAOYSA-N 2-prop-1-en-2-ylbenzenesulfonic acid Chemical class CC(=C)C1=CC=CC=C1S(O)(=O)=O SMFDSFRYWRBNSQ-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 102000016943 Muramidase Human genes 0.000 description 2
- 108010014251 Muramidase Proteins 0.000 description 2
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004325 lysozyme Substances 0.000 description 2
- 229960000274 lysozyme Drugs 0.000 description 2
- 235000010335 lysozyme Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- MMBPSOJWYRIRMS-UHFFFAOYSA-N 1-chloro-1-phenylbut-3-ene-1-sulfonic acid Chemical class C=CCC(Cl)(S(=O)(=O)O)C1=CC=CC=C1 MMBPSOJWYRIRMS-UHFFFAOYSA-N 0.000 description 1
- OZFIGURLAJSLIR-UHFFFAOYSA-N 1-ethenyl-2h-pyridine Chemical compound C=CN1CC=CC=C1 OZFIGURLAJSLIR-UHFFFAOYSA-N 0.000 description 1
- ZCHMCDBADMAKNR-UHFFFAOYSA-N 1-methyl-2h-pyrimidine-2,4-dicarboxylic acid Chemical compound CN1C=CC(C(O)=O)=NC1C(O)=O ZCHMCDBADMAKNR-UHFFFAOYSA-N 0.000 description 1
- UBPFKSSDARNMNX-UHFFFAOYSA-N 2,3-dichloro-4-ethenylnaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=C(Cl)C(Cl)=C(C=C)C2=C1 UBPFKSSDARNMNX-UHFFFAOYSA-N 0.000 description 1
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
- ZLSCHGRWXSMZBB-UHFFFAOYSA-N 2-(1,2,2-trihydroxyethenyl)benzenesulfonic acid Chemical class OC(O)=C(O)C1=CC=CC=C1S(O)(=O)=O ZLSCHGRWXSMZBB-UHFFFAOYSA-N 0.000 description 1
- IVERURBVJAABRR-UHFFFAOYSA-N 2-(2-bromoethenyl)benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1C=CBr IVERURBVJAABRR-UHFFFAOYSA-N 0.000 description 1
- XWSGEVNYFYKXCP-UHFFFAOYSA-N 2-[carboxymethyl(methyl)amino]acetic acid Chemical compound OC(=O)CN(C)CC(O)=O XWSGEVNYFYKXCP-UHFFFAOYSA-N 0.000 description 1
- HAZOZRAPGZDOEM-UHFFFAOYSA-N 2-aminoacetohydrazide Chemical compound NCC(=O)NN HAZOZRAPGZDOEM-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- GPOGMJLHWQHEGF-UHFFFAOYSA-N 2-chloroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCl GPOGMJLHWQHEGF-UHFFFAOYSA-N 0.000 description 1
- BBJJJPPTYKZIJP-UHFFFAOYSA-N 2-ethenoxybenzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1OC=C BBJJJPPTYKZIJP-UHFFFAOYSA-N 0.000 description 1
- XHCCPUQVFMEKIZ-UHFFFAOYSA-N 2-ethenyl-4,6-dimethylpyridine Chemical compound CC1=CC(C)=NC(C=C)=C1 XHCCPUQVFMEKIZ-UHFFFAOYSA-N 0.000 description 1
- YQUDMNIUBTXLSX-UHFFFAOYSA-N 2-ethenyl-5-ethylpyridine Chemical compound CCC1=CC=C(C=C)N=C1 YQUDMNIUBTXLSX-UHFFFAOYSA-N 0.000 description 1
- LCFYCLRCIJDYQD-UHFFFAOYSA-N 2-ethenyl-5-methylpyridine Chemical compound CC1=CC=C(C=C)N=C1 LCFYCLRCIJDYQD-UHFFFAOYSA-N 0.000 description 1
- VMWGBWNAHAUQIO-UHFFFAOYSA-N 2-ethenyl-6-methylpyridine Chemical compound CC1=CC=CC(C=C)=N1 VMWGBWNAHAUQIO-UHFFFAOYSA-N 0.000 description 1
- VMSBGXAJJLPWKV-UHFFFAOYSA-N 2-ethenylbenzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1C=C VMSBGXAJJLPWKV-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- HFQRGMYQLGXWRI-UHFFFAOYSA-N 2-prop-1-en-2-ylnaphthalene-1-sulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(C(=C)C)=CC=C21 HFQRGMYQLGXWRI-UHFFFAOYSA-N 0.000 description 1
- BHDBDYGQQIHGSV-UHFFFAOYSA-N 2-propan-2-yl-6-prop-1-en-2-ylbenzenesulfonic acid Chemical class CC(C)C1=CC=CC(C(C)=C)=C1S(O)(=O)=O BHDBDYGQQIHGSV-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- VOPLICFBIPVZTC-UHFFFAOYSA-N 3-(dimethylamino)cyclopentane-1,2-dicarboxylic acid Chemical compound CN(C)C1CCC(C(O)=O)C1C(O)=O VOPLICFBIPVZTC-UHFFFAOYSA-N 0.000 description 1
- ATBDZSAENDYQDW-UHFFFAOYSA-N 3-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C=C)=C1 ATBDZSAENDYQDW-UHFFFAOYSA-N 0.000 description 1
- DPZYLEIWHTWHCU-UHFFFAOYSA-N 3-ethenylpyridine Chemical compound C=CC1=CC=CN=C1 DPZYLEIWHTWHCU-UHFFFAOYSA-N 0.000 description 1
- LNIRBSSUMJWSBZ-UHFFFAOYSA-N 4-prop-1-en-2-ylbenzenesulfonic acid Chemical compound CC(=C)C1=CC=C(S(O)(=O)=O)C=C1 LNIRBSSUMJWSBZ-UHFFFAOYSA-N 0.000 description 1
- CARJPEPCULYFFP-UHFFFAOYSA-N 5-Sulfo-1,3-benzenedicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 CARJPEPCULYFFP-UHFFFAOYSA-N 0.000 description 1
- USQOVYLRWBOSQC-HNNXBMFYSA-N CCCCCCNC(=O)Oc1cccc(c1)-c1ccc(cc1F)[C@H](C)C(O)=O Chemical compound CCCCCCNC(=O)Oc1cccc(c1)-c1ccc(cc1F)[C@H](C)C(O)=O USQOVYLRWBOSQC-HNNXBMFYSA-N 0.000 description 1
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
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- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
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- 229910006069 SO3H Inorganic materials 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
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- 239000001361 adipic acid Substances 0.000 description 1
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- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000002965 anti-thrombogenic effect Effects 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
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- 239000008280 blood Substances 0.000 description 1
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- 150000001649 bromium compounds Chemical class 0.000 description 1
- PHPRBRMJBRAPOV-UHFFFAOYSA-N but-2-ene-1-sulfonic acid Chemical compound CC=CCS(O)(=O)=O PHPRBRMJBRAPOV-UHFFFAOYSA-N 0.000 description 1
- MXYJJDFPHIIPMC-UHFFFAOYSA-N but-3-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CCC=C MXYJJDFPHIIPMC-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical class CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- VFIJKQJHCCRWHE-UHFFFAOYSA-N hex-1-ene-1-sulfonic acid Chemical class CCCCC=CS(O)(=O)=O VFIJKQJHCCRWHE-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SDYRIBONPHEWCT-UHFFFAOYSA-N n,n-dimethyl-2-phenylethenamine Chemical compound CN(C)C=CC1=CC=CC=C1 SDYRIBONPHEWCT-UHFFFAOYSA-N 0.000 description 1
- NINOYJQVULROET-UHFFFAOYSA-N n,n-dimethylethenamine Chemical compound CN(C)C=C NINOYJQVULROET-UHFFFAOYSA-N 0.000 description 1
- BXAQFTLBYMGEIQ-UHFFFAOYSA-N n,n-dimethylhexan-3-amine Chemical compound CCCC(CC)N(C)C BXAQFTLBYMGEIQ-UHFFFAOYSA-N 0.000 description 1
- NXBBFAKHXAMPOM-UHFFFAOYSA-N n,n-dimethylprop-1-en-1-amine Chemical compound CC=CN(C)C NXBBFAKHXAMPOM-UHFFFAOYSA-N 0.000 description 1
- DDCVREGVKUIOSZ-UHFFFAOYSA-N n,n-dimethylprop-1-en-2-amine Chemical compound CN(C)C(C)=C DDCVREGVKUIOSZ-UHFFFAOYSA-N 0.000 description 1
- GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- MSIBHARACSILSI-UHFFFAOYSA-N oct-5-en-1-amine Chemical compound CCC=CCCCCN MSIBHARACSILSI-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- BIYCHPUIIDCAPR-UHFFFAOYSA-N pent-2-ene-2-sulfonic acid Chemical class CCC=C(C)S(O)(=O)=O BIYCHPUIIDCAPR-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical group [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003047 pimelic acids Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000090 poly(aryl ether) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- RAJUSMULYYBNSJ-UHFFFAOYSA-N prop-1-ene-1-sulfonic acid Chemical compound CC=CS(O)(=O)=O RAJUSMULYYBNSJ-UHFFFAOYSA-N 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 150000003442 suberic acids Chemical class 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin 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
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
- B01D71/80—Block polymers
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0809—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups
- C08G18/0814—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups containing ammonium groups or groups forming them
-
- 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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
-
- 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
- C08G2340/00—Filter material
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Secondary Cells (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Paints Or Removers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7343242A FR2252862B1 (nl) | 1973-12-04 | 1973-12-04 | |
| FR7426738A FR2280684A1 (fr) | 1973-12-04 | 1974-08-01 | Procede de preparation de polyelectrolytes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL46177A0 IL46177A0 (en) | 1975-03-13 |
| IL46177A true IL46177A (en) | 1977-05-31 |
Family
ID=26218065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL46177A IL46177A (en) | 1973-12-04 | 1974-12-03 | Process for preparing a complex polyelectrolyte from two types of polymer and product obtained thereby |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS50105735A (nl) |
| BE (2) | BE822902A (nl) |
| BR (1) | BR7410097A (nl) |
| CH (1) | CH589678A5 (nl) |
| DE (2) | DE2457328A1 (nl) |
| DK (1) | DK627974A (nl) |
| ES (1) | ES432558A1 (nl) |
| FR (2) | FR2252862B1 (nl) |
| GB (2) | GB1473857A (nl) |
| IL (1) | IL46177A (nl) |
| IT (1) | IT1026766B (nl) |
| LU (2) | LU71413A1 (nl) |
| NL (2) | NL7415424A (nl) |
| SU (1) | SU575034A3 (nl) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2286851A1 (fr) * | 1974-10-02 | 1976-04-30 | Inst Nat Rech Chimique | Membranes en polyacrylamide reticule ou en polyacrylamide substitue reticule, leur fabrication et leur application |
| US4005012A (en) * | 1975-09-22 | 1977-01-25 | The United States Of America As Represented By The Secretary Of The Interior | Semipermeable membranes and the method for the preparation thereof |
| LU76955A1 (nl) * | 1977-03-15 | 1978-10-18 | ||
| US4125462A (en) * | 1977-08-30 | 1978-11-14 | Rohm And Haas Company | Coated membranes |
| JPS5554004A (en) * | 1978-10-18 | 1980-04-21 | Teijin Ltd | Selective permeable membrane and its manufacturing |
| EP0056175B1 (en) * | 1981-01-13 | 1985-05-02 | Teijin Limited | Ion-permeable composite membrane and its use in selective separation |
| LU83350A1 (fr) * | 1981-05-08 | 1983-03-24 | Oreal | Composition destinee au traitement des fibres keratiniques a base de polymere cationique et de polymere anionique a groupements vinylsulfoniques et procede de traitement la mettant en oeuvre |
| US4415608A (en) * | 1982-01-15 | 1983-11-15 | Uop Inc. | Continuous production of polymethylpentene membranes |
| CH656626A5 (fr) * | 1982-02-05 | 1986-07-15 | Pall Corp | Membrane en polyamide, presentant des proprietes de surface controlees, son utilisation et son procede de preparation. |
| US4707266A (en) * | 1982-02-05 | 1987-11-17 | Pall Corporation | Polyamide membrane with controlled surface properties |
| US4427419A (en) * | 1982-03-12 | 1984-01-24 | The Standard Oil Company | Semipermeable membranes prepared from polymers containing pendent sulfone groups |
| US4539373A (en) * | 1982-07-12 | 1985-09-03 | The Dow Chemical Company | Thermoplastic polyelectrolyte complexes |
| US4806189A (en) * | 1984-08-13 | 1989-02-21 | Monsanto Company | Composite fluid separation membranes |
| US4717395A (en) * | 1986-08-07 | 1988-01-05 | The Dow Chemical Company | Gas separations using membranes comprising sulphonated polyether sulphone |
| JP2694341B2 (ja) * | 1987-02-04 | 1997-12-24 | ハイドロノーティクス | 改良された耐酸化性膜およびその製造方法 |
| US4990252A (en) * | 1987-02-04 | 1991-02-05 | Hydanautics | Stable membranes from sulfonated polyarylethers |
| US4840819A (en) * | 1987-04-08 | 1989-06-20 | Union Carbide Corporation | Method for preparing composite membranes for enhanced gas separation |
| US4826599A (en) * | 1987-07-10 | 1989-05-02 | Union Carbide Corporation | Composite membranes and their manufacture and use |
| JPH01215348A (ja) * | 1988-02-25 | 1989-08-29 | Asahi Glass Co Ltd | 陽イオン交換体 |
| DE4428641A1 (de) * | 1994-08-12 | 1996-02-15 | Basf Ag | Mesomorphe Komplexe aus Polyelektrolyten und Tensiden, Verfahren zu ihrer Herstellung sowie Filme, Folien, Fasern, Formkörper und Beschichtungen hieraus |
| US6026968A (en) * | 1996-05-13 | 2000-02-22 | Nitto Denko Corporation | Reverse osmosis composite membrane |
| EP0948746A1 (en) * | 1996-11-14 | 1999-10-13 | Pall Corporation | Membrane and methods of preparing and using same |
| DE19841404C2 (de) * | 1998-09-10 | 2000-12-21 | Basf Coatings Ag | Feststoffe auf der Basis mesomorpher Polyelektrolytkomplexe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DK2313184T3 (da) * | 2008-08-05 | 2013-01-21 | Polymers Crc Ltd | Funktionaliserede tynde film polyamidmembraner |
| US10384167B2 (en) | 2013-11-21 | 2019-08-20 | Oasys Water LLC | Systems and methods for improving performance of osmotically driven membrane systems |
| KR102657532B1 (ko) | 2015-08-20 | 2024-04-12 | 니폰 제온 가부시키가이샤 | 비수계 2차 전지용 바인더 조성물, 비수계 2차 전지 기능층용 조성물, 비수계 2차 전지용 기능층 및 비수계 2차 전지 |
| US11872532B2 (en) | 2018-09-05 | 2024-01-16 | Campbell Membrane Technologies, Inc. | Ultrafiltration membranes for dairy protein separation |
| WO2024219965A1 (en) | 2023-04-17 | 2024-10-24 | Stichting Wageningen Research | Polyelectrolyte complex |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1493044A (fr) * | 1966-07-13 | 1967-08-25 | Nouveaux copolymères non caoutchouteux | |
| BE785741A (fr) * | 1971-07-02 | 1973-01-02 | Rhone Poulenc Sa | Polyelectrolytes |
-
1973
- 1973-12-04 FR FR7343242A patent/FR2252862B1/fr not_active Expired
-
1974
- 1974-08-01 FR FR7426738A patent/FR2280684A1/fr active Granted
- 1974-11-26 NL NL7415424A patent/NL7415424A/nl not_active Application Discontinuation
- 1974-11-26 NL NL7415419A patent/NL7415419A/nl not_active Application Discontinuation
- 1974-12-03 BE BE151115A patent/BE822902A/xx unknown
- 1974-12-03 IL IL46177A patent/IL46177A/en unknown
- 1974-12-03 DK DK627974A patent/DK627974A/da unknown
- 1974-12-03 BR BR10097/74A patent/BR7410097A/pt unknown
- 1974-12-03 CH CH1604474A patent/CH589678A5/xx not_active IP Right Cessation
- 1974-12-03 LU LU71413A patent/LU71413A1/xx unknown
- 1974-12-03 BE BE151114A patent/BE822901A/xx unknown
- 1974-12-03 GB GB5227074A patent/GB1473857A/en not_active Expired
- 1974-12-03 LU LU71412A patent/LU71412A1/xx unknown
- 1974-12-03 GB GB5226574A patent/GB1463175A/en not_active Expired
- 1974-12-03 SU SU7402082929A patent/SU575034A3/ru active
- 1974-12-03 JP JP49139351A patent/JPS50105735A/ja active Pending
- 1974-12-03 IT IT30150/74A patent/IT1026766B/it active
- 1974-12-04 DE DE19742457328 patent/DE2457328A1/de active Pending
- 1974-12-04 ES ES432558A patent/ES432558A1/es not_active Expired
- 1974-12-04 DE DE2457355A patent/DE2457355C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2457355A1 (de) | 1975-06-05 |
| LU71412A1 (nl) | 1975-08-20 |
| GB1463175A (en) | 1977-02-02 |
| CH589678A5 (nl) | 1977-07-15 |
| ES432558A1 (es) | 1977-03-01 |
| DE2457355B2 (de) | 1979-08-02 |
| FR2252862B1 (nl) | 1978-10-27 |
| FR2280684A1 (fr) | 1976-02-27 |
| BE822901A (fr) | 1975-06-03 |
| FR2252862A1 (nl) | 1975-06-27 |
| JPS50105735A (nl) | 1975-08-20 |
| DE2457328A1 (de) | 1975-06-05 |
| LU71413A1 (nl) | 1975-08-20 |
| BE822902A (fr) | 1975-06-03 |
| BR7410097A (pt) | 1976-06-08 |
| NL7415424A (nl) | 1975-06-06 |
| GB1473857A (en) | 1977-05-18 |
| FR2280684B1 (nl) | 1977-03-18 |
| NL7415419A (nl) | 1975-06-06 |
| SU575034A3 (ru) | 1977-09-30 |
| DE2457355C3 (de) | 1980-04-03 |
| IT1026766B (it) | 1978-10-20 |
| DK627974A (nl) | 1975-07-28 |
| IL46177A0 (en) | 1975-03-13 |
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