CA1298739C - Semi-permeable membranes prepared via reaction of cationic groups with nucleophilic groups - Google Patents
Semi-permeable membranes prepared via reaction of cationic groups with nucleophilic groupsInfo
- Publication number
- CA1298739C CA1298739C CA 521001 CA521001A CA1298739C CA 1298739 C CA1298739 C CA 1298739C CA 521001 CA521001 CA 521001 CA 521001 A CA521001 A CA 521001A CA 1298739 C CA1298739 C CA 1298739C
- Authority
- CA
- Canada
- Prior art keywords
- membrane
- compound
- reactive
- percent
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000012528 membrane Substances 0.000 title claims abstract description 318
- 230000000269 nucleophilic effect Effects 0.000 title claims abstract description 83
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 53
- 125000002091 cationic group Chemical group 0.000 title claims description 110
- 150000001875 compounds Chemical group 0.000 claims abstract description 118
- 238000000034 method Methods 0.000 claims abstract description 57
- 239000000758 substrate Substances 0.000 claims abstract description 52
- 238000000926 separation method Methods 0.000 claims abstract description 19
- 238000001223 reverse osmosis Methods 0.000 claims abstract description 18
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 238000000108 ultra-filtration Methods 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 137
- 229920000642 polymer Polymers 0.000 claims description 113
- 238000000576 coating method Methods 0.000 claims description 74
- 239000000178 monomer Substances 0.000 claims description 54
- -1 thiazolinium Chemical compound 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 47
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 38
- 229920001577 copolymer Polymers 0.000 claims description 35
- 230000008093 supporting effect Effects 0.000 claims description 20
- 229920002492 poly(sulfone) Polymers 0.000 claims description 19
- 239000003085 diluting agent Substances 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 17
- 229920002554 vinyl polymer Polymers 0.000 claims description 15
- 229920002873 Polyethylenimine Polymers 0.000 claims description 14
- 229920002678 cellulose Polymers 0.000 claims description 14
- 125000003010 ionic group Chemical group 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 12
- 150000007942 carboxylates Chemical class 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 150000008040 ionic compounds Chemical class 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000000835 fiber Substances 0.000 claims description 8
- 239000012466 permeate Substances 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 8
- 239000012954 diazonium Substances 0.000 claims description 7
- 238000006073 displacement reaction Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 7
- 125000005537 sulfoxonium group Chemical group 0.000 claims description 7
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- HONIICLYMWZJFZ-UHFFFAOYSA-O azetidin-1-ium Chemical compound C1C[NH2+]C1 HONIICLYMWZJFZ-UHFFFAOYSA-O 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- 125000001165 hydrophobic group Chemical group 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical group [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 5
- 229920002401 polyacrylamide Polymers 0.000 claims description 5
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 230000008033 biological extinction Effects 0.000 claims description 4
- 229920001519 homopolymer Polymers 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims description 3
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 3
- 239000011118 polyvinyl acetate Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 3
- 238000009877 rendering Methods 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- DHSQXMJAGIRIJZ-UHFFFAOYSA-N 2-tert-butylphenol sulfane Chemical compound S.CC(C)(C)C1=CC=CC=C1O DHSQXMJAGIRIJZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000001464 adherent effect Effects 0.000 claims description 2
- 229920006187 aquazol Polymers 0.000 claims description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- NARVIWMVBMUEOG-UHFFFAOYSA-N prop-1-en-2-ol Chemical group CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 abstract description 80
- 125000000129 anionic group Chemical group 0.000 abstract description 38
- 150000001767 cationic compounds Chemical group 0.000 abstract description 27
- 239000002131 composite material Substances 0.000 abstract description 23
- 210000004379 membrane Anatomy 0.000 description 269
- 239000000243 solution Substances 0.000 description 128
- 235000002639 sodium chloride Nutrition 0.000 description 77
- 239000011248 coating agent Substances 0.000 description 68
- 230000004907 flux Effects 0.000 description 52
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 51
- 239000007787 solid Substances 0.000 description 51
- 150000003839 salts Chemical class 0.000 description 50
- 239000004094 surface-active agent Substances 0.000 description 39
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 38
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 34
- 238000005266 casting Methods 0.000 description 33
- 239000012038 nucleophile Substances 0.000 description 30
- 239000002904 solvent Substances 0.000 description 30
- 239000000460 chlorine Substances 0.000 description 28
- 239000007864 aqueous solution Substances 0.000 description 27
- 239000011780 sodium chloride Substances 0.000 description 26
- 229940106691 bisphenol a Drugs 0.000 description 23
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 22
- 238000005755 formation reaction Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000000463 material Substances 0.000 description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 17
- 150000001768 cations Chemical class 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- 235000013350 formula milk Nutrition 0.000 description 16
- 150000001450 anions Chemical class 0.000 description 15
- 229940063559 methacrylic acid Drugs 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 14
- 239000007789 gas Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 230000008569 process Effects 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 12
- 229920001897 terpolymer Polymers 0.000 description 12
- 239000008367 deionised water Substances 0.000 description 11
- 229910021641 deionized water Inorganic materials 0.000 description 11
- OSIVISXRDMXJQR-UHFFFAOYSA-M potassium;2-[ethyl(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctylsulfonyl)amino]acetate Chemical compound [K+].[O-]C(=O)CN(CC)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F OSIVISXRDMXJQR-UHFFFAOYSA-M 0.000 description 11
- 239000002243 precursor Substances 0.000 description 11
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 10
- 230000035699 permeability Effects 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000008199 coating composition Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000002411 adverse Effects 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 239000011148 porous material Substances 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 229920006318 anionic polymer Polymers 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000012510 hollow fiber Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229920000867 polyelectrolyte Polymers 0.000 description 6
- 229960002668 sodium chloride Drugs 0.000 description 6
- 229940117958 vinyl acetate Drugs 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 5
- 229920002284 Cellulose triacetate Polymers 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 230000008030 elimination Effects 0.000 description 5
- 238000003379 elimination reaction Methods 0.000 description 5
- 229960004594 fominoben Drugs 0.000 description 5
- 229920000831 ionic polymer Polymers 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011550 stock solution Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical class C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 239000001768 carboxy methyl cellulose Substances 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 230000002939 deleterious effect Effects 0.000 description 4
- 238000009432 framing Methods 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 150000004010 onium ions Chemical group 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical class NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000013011 aqueous formulation Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 229940105329 carboxymethylcellulose Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229940119545 isobornyl methacrylate Drugs 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 3
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 3
- LUCXVPAZUDVVBT-UHFFFAOYSA-N methyl-[3-(2-methylphenoxy)-3-phenylpropyl]azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1C LUCXVPAZUDVVBT-UHFFFAOYSA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 235000014786 phosphorus Nutrition 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920013730 reactive polymer Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- 230000007480 spreading Effects 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229920001059 synthetic polymer Polymers 0.000 description 3
- UPUCFIMLARFWLZ-UHFFFAOYSA-N thiolane;hydrate Chemical compound O.C1CCSC1 UPUCFIMLARFWLZ-UHFFFAOYSA-N 0.000 description 3
- 150000007944 thiolates Chemical class 0.000 description 3
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical class O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- LPIQIQPLUVLISR-UHFFFAOYSA-N 2-prop-1-en-2-yl-4,5-dihydro-1,3-oxazole Chemical compound CC(=C)C1=NCCO1 LPIQIQPLUVLISR-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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- Y10T428/249962—Void-containing component has a continuous matrix of fibers only [e.g., porous paper, etc.]
- Y10T428/249964—Fibers of defined composition
- Y10T428/249965—Cellulosic
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
- Y10T428/249971—Preformed hollow element-containing
- Y10T428/249972—Resin or rubber element
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
- Y10T428/249978—Voids specified as micro
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/790,287 US4704324A (en) | 1985-04-03 | 1985-10-22 | Semi-permeable membranes prepared via reaction of cationic groups with nucleophilic groups |
| US790,287 | 1985-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1298739C true CA1298739C (en) | 1992-04-14 |
Family
ID=25150231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 521001 Expired - Fee Related CA1298739C (en) | 1985-10-22 | 1986-10-21 | Semi-permeable membranes prepared via reaction of cationic groups with nucleophilic groups |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US4704324A (enFirst) |
| EP (1) | EP0220660B1 (enFirst) |
| JP (1) | JPS62502320A (enFirst) |
| AU (1) | AU573465B2 (enFirst) |
| CA (1) | CA1298739C (enFirst) |
| DE (1) | DE3684227D1 (enFirst) |
| IL (1) | IL80395A0 (enFirst) |
| WO (1) | WO1987002682A1 (enFirst) |
| ZA (1) | ZA868031B (enFirst) |
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-
1985
- 1985-10-22 US US06/790,287 patent/US4704324A/en not_active Expired - Lifetime
-
1986
- 1986-10-17 JP JP61505968A patent/JPS62502320A/ja active Granted
- 1986-10-17 AU AU65957/86A patent/AU573465B2/en not_active Ceased
- 1986-10-17 WO PCT/US1986/002205 patent/WO1987002682A1/en not_active Ceased
- 1986-10-21 DE DE8686114566T patent/DE3684227D1/de not_active Expired - Fee Related
- 1986-10-21 CA CA 521001 patent/CA1298739C/en not_active Expired - Fee Related
- 1986-10-21 EP EP19860114566 patent/EP0220660B1/en not_active Expired - Lifetime
- 1986-10-22 IL IL80395A patent/IL80395A0/xx not_active IP Right Cessation
- 1986-10-22 ZA ZA868031A patent/ZA868031B/xx unknown
-
1987
- 1987-08-17 US US07/086,123 patent/US4797187A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0474043B2 (enFirst) | 1992-11-25 |
| DE3684227D1 (de) | 1992-04-16 |
| JPS62502320A (ja) | 1987-09-10 |
| IL80395A0 (en) | 1987-01-30 |
| WO1987002682A1 (en) | 1987-05-07 |
| EP0220660B1 (en) | 1992-03-11 |
| AU573465B2 (en) | 1988-06-09 |
| EP0220660A3 (en) | 1989-10-04 |
| ZA868031B (en) | 1988-06-29 |
| EP0220660A2 (en) | 1987-05-06 |
| AU6595786A (en) | 1987-05-19 |
| US4797187A (en) | 1989-01-10 |
| US4704324A (en) | 1987-11-03 |
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