TWI302540B - Fluoropolymer resins containing ionic or ionizable groups and products containing the same - Google Patents
Fluoropolymer resins containing ionic or ionizable groups and products containing the same Download PDFInfo
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- TWI302540B TWI302540B TW090103434A TW90103434A TWI302540B TW I302540 B TWI302540 B TW I302540B TW 090103434 A TW090103434 A TW 090103434A TW 90103434 A TW90103434 A TW 90103434A TW I302540 B TWI302540 B TW I302540B
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- polymer
- ionic
- weight
- polymer blend
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- 229920002313 fluoropolymer Polymers 0.000 title claims abstract description 37
- 239000004811 fluoropolymer Substances 0.000 title claims abstract description 36
- 229920005989 resin Polymers 0.000 title claims abstract description 24
- 239000011347 resin Substances 0.000 title claims abstract description 24
- 229920000642 polymer Polymers 0.000 claims abstract description 67
- 239000000203 mixture Substances 0.000 claims abstract description 38
- 239000000446 fuel Substances 0.000 claims abstract description 35
- 229920002959 polymer blend Polymers 0.000 claims abstract description 27
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 21
- 239000012528 membrane Substances 0.000 claims abstract description 19
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 18
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 17
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 17
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 10
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims description 64
- 239000010408 film Substances 0.000 claims description 50
- -1 acryl Chemical group 0.000 claims description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 15
- 125000003010 ionic group Chemical group 0.000 claims description 13
- 239000006185 dispersion Substances 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 10
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000003014 ion exchange membrane Substances 0.000 claims description 8
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- 102100035353 Cyclin-dependent kinase 2-associated protein 1 Human genes 0.000 claims 3
- 229920000554 ionomer Polymers 0.000 claims 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims 1
- 230000026731 phosphorylation Effects 0.000 claims 1
- 238000006366 phosphorylation reaction Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000004816 latex Substances 0.000 description 25
- 229920000126 latex Polymers 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 229910001868 water Inorganic materials 0.000 description 15
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
- 239000002033 PVDF binder Substances 0.000 description 7
- 238000012864 cross contamination Methods 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000005250 alkyl acrylate group Chemical group 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000005518 polymer electrolyte Substances 0.000 description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 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 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- WFLOTYSKFUPZQB-UHFFFAOYSA-N 1,2-difluoroethene Chemical group FC=CF WFLOTYSKFUPZQB-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- KFNGWPXYNSJXOP-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propane-1-sulfonic acid Chemical compound CC(=C)C(=O)OCCCS(O)(=O)=O KFNGWPXYNSJXOP-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 2
- 239000004815 dispersion polymer Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229920000831 ionic polymer Polymers 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- GUJIFUOBRWBJQZ-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.OCCOCCO GUJIFUOBRWBJQZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- QRZMITSTLWZLER-UHFFFAOYSA-N 2-hydrazinylethanethiol Chemical compound NNCCS QRZMITSTLWZLER-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- LSCOLVARJKRPAO-UHFFFAOYSA-N 2-methylprop-2-enoic acid;oxane Chemical compound CC(=C)C(O)=O.C1CCOCC1 LSCOLVARJKRPAO-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- DAWJJMYZJQJLPZ-UHFFFAOYSA-N 2-sulfanylprop-2-enoic acid Chemical compound OC(=O)C(S)=C DAWJJMYZJQJLPZ-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- GETJHIYPEXUGHO-UHFFFAOYSA-N 3-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCNC(=O)C=C GETJHIYPEXUGHO-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- ROKIIXGDTHKIAY-UHFFFAOYSA-N C(C(=C)C)(=O)NC.NN Chemical compound C(C(=C)C)(=O)NC.NN ROKIIXGDTHKIAY-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical group [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 229920002274 Nalgene Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000287107 Passer Species 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- CLFBXKHKECKSQM-UHFFFAOYSA-N Pseudopalmatine Chemical compound COC1=C(OC)C=C2C=C(C3=C(C=C(C(=C3)OC)OC)CC3)[N+]3=CC2=C1 CLFBXKHKECKSQM-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- BXOBFMUWVVHLFK-QXMHVHEDSA-N [(z)-octadec-9-enyl] 2-methylprop-2-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)C(C)=C BXOBFMUWVVHLFK-QXMHVHEDSA-N 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08F259/08—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00 on to polymers containing fluorine
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- Y02E60/50—Fuel cells
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- 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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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18273200P | 2000-02-15 | 2000-02-15 | |
| US09/774,266 US6780935B2 (en) | 2000-02-15 | 2001-01-30 | Fluoropolymer resins containing ionic or ionizable groups and products containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI302540B true TWI302540B (en) | 2008-11-01 |
Family
ID=26878363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090103434A TWI302540B (en) | 2000-02-15 | 2001-03-08 | Fluoropolymer resins containing ionic or ionizable groups and products containing the same |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6780935B2 (enExample) |
| EP (1) | EP1177221A4 (enExample) |
| JP (1) | JP4837216B2 (enExample) |
| KR (1) | KR100743845B1 (enExample) |
| CN (1) | CN1142193C (enExample) |
| CA (1) | CA2369696C (enExample) |
| IL (1) | IL145673A (enExample) |
| MX (1) | MXPA01010408A (enExample) |
| RU (1) | RU2264420C2 (enExample) |
| TW (1) | TWI302540B (enExample) |
| WO (1) | WO2001060872A1 (enExample) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7318972B2 (en) | 2001-09-07 | 2008-01-15 | Itm Power Ltd. | Hydrophilic polymers and their use in electrochemical cells |
| FR2852016B1 (fr) * | 2003-03-03 | 2006-07-07 | Atofina | Procede de fabrication de pvdf thermiquement stable |
| FR2852017B1 (fr) * | 2003-03-03 | 2005-04-22 | Atofina | Procede de fabrication de pvdf thermiquement stable |
| US20040175625A1 (en) * | 2003-03-06 | 2004-09-09 | Lotfi Hedhli | Non-perfluorinated resins containing ionic or ionizable groups and products containing the same |
| US6841616B2 (en) * | 2003-03-28 | 2005-01-11 | Arkema Inc. | Polymerization of halogen-containing monomers using siloxane surfactant |
| CN100336860C (zh) * | 2003-07-24 | 2007-09-12 | 巨化集团公司 | 纳米乳化含氟离子交换树脂制备方法和应用 |
| US7449111B2 (en) * | 2003-07-30 | 2008-11-11 | Arkema Inc. | Resins containing ionic or ionizable groups with small domain sizes and improved conductivity |
| US7071271B2 (en) * | 2003-10-30 | 2006-07-04 | 3M Innovative Properties Company | Aqueous emulsion polymerization of functionalized fluoromonomers |
| US7259208B2 (en) * | 2003-11-13 | 2007-08-21 | 3M Innovative Properties Company | Reinforced polymer electrolyte membrane |
| US7179847B2 (en) * | 2003-11-13 | 2007-02-20 | 3M Innovative Properties Company | Polymer electrolytes crosslinked by e-beam |
| US7265162B2 (en) * | 2003-11-13 | 2007-09-04 | 3M Innovative Properties Company | Bromine, chlorine or iodine functional polymer electrolytes crosslinked by e-beam |
| US7074841B2 (en) | 2003-11-13 | 2006-07-11 | Yandrasits Michael A | Polymer electrolyte membranes crosslinked by nitrile trimerization |
| US7060756B2 (en) * | 2003-11-24 | 2006-06-13 | 3M Innovative Properties Company | Polymer electrolyte with aromatic sulfone crosslinking |
| US7112614B2 (en) * | 2003-12-08 | 2006-09-26 | 3M Innovative Properties Company | Crosslinked polymer |
| US7060738B2 (en) * | 2003-12-11 | 2006-06-13 | 3M Innovative Properties Company | Polymer electrolytes crosslinked by ultraviolet radiation |
| US7173067B2 (en) | 2003-12-17 | 2007-02-06 | 3M Innovative Properties Company | Polymer electrolyte membranes crosslinked by direct fluorination |
| US7267865B2 (en) * | 2004-02-20 | 2007-09-11 | Saint-Gobain Performance Plastics Corporation | Draw resonant resistant multilayer films |
| US7297391B2 (en) * | 2004-02-20 | 2007-11-20 | Saint-Gobain Performance Plastics Corporation | Draw resonance resistant multilayer films |
| JP4613528B2 (ja) | 2004-06-24 | 2011-01-19 | コニカミノルタホールディングス株式会社 | プロトン伝導性電解質膜とその製造方法、及び該プロトン伝導性電解質膜を用いた固体高分子型燃料電池 |
| US8039160B2 (en) * | 2004-07-14 | 2011-10-18 | Arkema Inc. | Multi-layer polyelectrolyte membrane |
| JP4915043B2 (ja) * | 2004-11-15 | 2012-04-11 | コニカミノルタホールディングス株式会社 | プロトン伝導性電解質膜とその製造方法、及び該プロトン伝導性電解質膜を用いた固体高分子型燃料電池 |
| JP4774216B2 (ja) * | 2005-01-28 | 2011-09-14 | 株式会社リコー | 電子伝導イオン伝導物質の製造方法、複合体、燃料電池、電源及び電子機器 |
| EP1691440A1 (en) * | 2005-02-07 | 2006-08-16 | Fuji Photo Film Co., Ltd. | Solid electrolyte, method for producing the solid electrolyte, membrane, membrane electrode assembly and fuel cell comprising the solid electrolyte |
| US7396880B2 (en) * | 2005-05-24 | 2008-07-08 | Arkema Inc. | Blend of ionic (co)polymer resins and matrix (co)polymers |
| EP1897166A2 (en) | 2005-06-27 | 2008-03-12 | ITM Power (Research) Limited | Membrane electrode assemblies |
| FR2890971A1 (fr) * | 2005-09-21 | 2007-03-23 | Specific Polymers Soc Responsa | Compositions de polymeres fluores adherentes sur surface metallique |
| US7901778B2 (en) * | 2006-01-13 | 2011-03-08 | Saint-Gobain Performance Plastics Corporation | Weatherable multilayer film |
| TW200740913A (en) * | 2006-02-02 | 2007-11-01 | Jsr Corp | Polymer composition, paste for secondary battery electrode, and secondary battery electrode |
| EP2038332B1 (en) * | 2006-06-29 | 2013-11-06 | Avery Dennison Corporation | Polyvinylidene fluoride films and laminates thereof |
| CN101970992A (zh) * | 2006-11-21 | 2011-02-09 | 阿科玛股份有限公司 | 耐苛性碱薄膜 |
| KR100986493B1 (ko) * | 2008-05-08 | 2010-10-08 | 주식회사 동진쎄미켐 | 연료전지용 고분자 전해질 막 |
| EP2332639A1 (en) * | 2008-09-19 | 2011-06-15 | Toray Industries, Inc. | Separation membrane, and method for producing same |
| CN102196849B (zh) * | 2008-10-28 | 2014-12-31 | 阿科玛股份有限公司 | 水通性聚合物薄膜 |
| JP5744016B2 (ja) | 2009-06-15 | 2015-07-01 | アーケマ・インコーポレイテッド | ナノ粒子を含む高分子電解質ブレンド物の有機/無機複合ブレンド物膜組成物 |
| WO2012079231A1 (en) | 2010-12-15 | 2012-06-21 | Rhodia (China) Co., Ltd. | Fluoropolymer compositions |
| US8809209B2 (en) | 2010-12-17 | 2014-08-19 | E I Du Pont De Nemours And Company | Fluorinated copolymers |
| EP2664016A1 (en) | 2011-01-11 | 2013-11-20 | ETV Energy Ltd. | Membranes suitable for use as separators and electrochemical cells including such separators |
| WO2012112840A1 (en) * | 2011-02-18 | 2012-08-23 | Arkema Inc. | Fluoropolymer gas separation films |
| KR101282028B1 (ko) * | 2011-04-18 | 2013-07-04 | 한국화학연구원 | 태양전지 모듈 백시트의 내후성 코팅용 불소고분자-퍼플루오로알킬기 함유 아크릴 입자 |
| WO2014055473A2 (en) * | 2012-10-04 | 2014-04-10 | Arkema Inc. | Porous separation article |
| KR102596288B1 (ko) * | 2016-11-29 | 2023-10-30 | 엘지디스플레이 주식회사 | 접촉 감응 소자 및 그를 포함하는 표시 장치 |
| EP3697823B1 (en) * | 2017-10-17 | 2024-01-24 | Solvay Specialty Polymers Italy S.p.A. | Method for the synthesis of fluoropolymers |
| CN108905650B (zh) * | 2018-08-06 | 2020-12-15 | 安徽大学 | 一种聚四氟乙烯基阳离子交换膜的制备方法 |
| CN114402467A (zh) * | 2019-06-25 | 2022-04-26 | 阿科玛股份有限公司 | 用于锂离子电池的混杂官能化含氟聚合物 |
| US20220311091A1 (en) * | 2019-06-25 | 2022-09-29 | Arkema Inc. | Coated separator with fluoropolymers for lithium ion battery |
| CN120271939A (zh) * | 2019-09-05 | 2025-07-08 | 大金工业株式会社 | 组合物及其制造方法 |
| CN111595965A (zh) * | 2020-05-11 | 2020-08-28 | 中国包装科研测试中心 | 包装材料中异戊二烯迁移量的检测方法 |
| KR102594964B1 (ko) * | 2022-05-26 | 2023-10-26 | 주식회사 엘지에너지솔루션 | 유기/무기 복합 다공성 코팅층을 포함하는 전기화학소자용 분리막 및 이를 포함하는 전기화학소자 |
| WO2025082898A1 (en) | 2023-10-16 | 2025-04-24 | Solvay Specialty Polymers Italy S.P.A. | Secondary batteries electrode binders |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1810528A (en) | 1929-06-12 | 1931-06-16 | Hotchkiss Co E H | Stapling machine |
| US1996222A (en) | 1933-09-01 | 1935-04-02 | Vogel Max | Stapling machine |
| DE1078329B (de) | 1955-04-27 | 1960-03-24 | Du Pont | Verfahren zur Herstellung eines elastischen Mischpolymerisats aus Vinylidenfluorid und einem anderen Fluorolefin |
| US2987729A (en) | 1959-02-10 | 1961-06-13 | Melpar Inc | Stapling device |
| GB975031A (en) * | 1960-02-01 | 1964-11-11 | American Mach & Foundry | Ion permeable membranes |
| US3178399A (en) | 1961-08-10 | 1965-04-13 | Minnesota Mining & Mfg | Fluorine-containing polymers and preparation thereof |
| US3475396A (en) | 1966-07-06 | 1969-10-28 | Diamond Shamrock Corp | Process for polymerizing vinylidene fluoride |
| US3504837A (en) | 1968-04-24 | 1970-04-07 | Werner Schafroth | Stapling machine and method of forming staples |
| DE1959147C3 (de) * | 1968-11-26 | 1979-12-06 | E.I. Du Pont De Nemours And Co., Wilmington, Del. (V.St.A.) | Oberflächenaktiver Fluorkohlenstoffpolymerisat-Gegenstand |
| US3642187A (en) | 1970-05-14 | 1972-02-15 | Flynn & Emrich Co | Stitching head |
| US3857827A (en) | 1974-01-25 | 1974-12-31 | Pennwalt Corp | Method of preparing high-quality vinylidene fluoride polymer in aqueous emulsion |
| JPS551351B2 (enExample) * | 1974-03-07 | 1980-01-12 | ||
| FR2268094B1 (enExample) | 1974-04-16 | 1976-10-08 | Rhone Poulenc Textile | |
| US4191811A (en) * | 1977-03-01 | 1980-03-04 | Ionics, Incorported | Ion exchange membranes based upon polyphenylene sulfide and fluorocarbon polymeric binder |
| JPS6053059B2 (ja) * | 1978-07-11 | 1985-11-22 | 旭化成株式会社 | 改良された陽イオン交換膜の製法 |
| IT1166581B (it) | 1979-01-17 | 1987-05-05 | Oronzio De Nora Impianti | Membrane cationiche a base di copolimeri solfonati di stirene divinilbenzene e 2- o 4-vinilpiridina o acido acrilico, procedimento per la loro preparazione ed uso in celle di elettrolisi |
| JPS6024812B2 (ja) | 1979-11-09 | 1985-06-14 | 呉羽化学工業株式会社 | 塩化ビニリデン系樹脂ケ−シング |
| US4318555A (en) | 1980-01-15 | 1982-03-09 | Eastman Kodak Company | Stapler |
| US4421264A (en) | 1981-06-26 | 1983-12-20 | International Business Machines Corporation | Variable thickness set compensation for stapler |
| US4583276A (en) | 1983-06-23 | 1986-04-22 | Swingline, Inc. | Method of forming and driving staples |
| US4569978A (en) | 1984-07-25 | 1986-02-11 | Pennwalt Corporation | Emulsion polymerization of vinylidene fluoride polymers in the presence of trichlorofluoromethane as chain transfer agent |
| DE3533840A1 (de) | 1985-09-23 | 1987-04-02 | Bosch Gmbh Robert | Kraftbetriebenes einschlaggeraet, insbesondere fuer heftklammern |
| FR2600265B1 (fr) * | 1986-06-20 | 1991-09-06 | Rhone Poulenc Rech | Membranes semi-permeables sechables et hydrophiles a base de polyfluorure de vinylidene |
| US5007483A (en) | 1988-02-03 | 1991-04-16 | Mcguire Douglas K | Hoof-buffing tool kit for farriers |
| US5093427A (en) | 1990-05-10 | 1992-03-03 | Atochem North America, Inc. | Copolymers of vinylidene fluoride and hexafluoropropylene and process for preparing the same |
| JP3128938B2 (ja) * | 1992-03-27 | 2001-01-29 | ジェイエスアール株式会社 | 水系フッ素重合体分散液の製造方法 |
| US5272186A (en) | 1992-05-01 | 1993-12-21 | E. I. Du Pont De Nemours And Company | Concentration of fluoropolymer dispersions using acrylic polymers of high acid content |
| SE500140C2 (sv) | 1992-06-30 | 1994-04-25 | Isaberg Ab | Häftapparat med flatläggningsmekanism |
| DE4243995C2 (de) * | 1992-12-23 | 1996-07-25 | Gore W L & Ass Gmbh | Permanente hydrophile Modifizierung für Fluorpolymere und Verfahren zur Erzeugung der Modifizierung |
| DE4326130A1 (de) | 1993-08-04 | 1995-02-09 | Huels Chemische Werke Ag | Thermoplastische Mehrschichtverbunde |
| JP3345788B2 (ja) * | 1993-12-26 | 2002-11-18 | ジャパンゴアテックス株式会社 | 電気化学反応装置用セパレータ |
| JPH07187487A (ja) | 1993-12-28 | 1995-07-25 | Toshiba Corp | ステイプル装置及びステイプル装置を有した画像形成装置 |
| DE4410148A1 (de) * | 1994-03-24 | 1995-09-28 | Huels Chemische Werke Ag | Mehrschichtiges Kunststoffrohr |
| ZA952384B (en) * | 1994-04-13 | 1996-09-23 | Nat Power Plc | Cation exchange membranes and method for the preparation of such membranes |
| US5468574A (en) | 1994-05-23 | 1995-11-21 | Dais Corporation | Fuel cell incorporating novel ion-conducting membrane |
| US5795668A (en) | 1994-11-10 | 1998-08-18 | E. I. Du Pont De Nemours And Company | Fuel cell incorporating a reinforced membrane |
| US5599614A (en) * | 1995-03-15 | 1997-02-04 | W. L. Gore & Associates, Inc. | Integral composite membrane |
| US5880204A (en) | 1995-09-27 | 1999-03-09 | Alliedsignal Inc. | Room temperature coalescable aqueous fluoropolymer dispersions and method for their manufacture |
| CA2252679C (en) | 1996-04-30 | 2003-10-28 | W. L. Gore & Associates, Inc. | Integral multi-layered ion-exchange composite membranes |
| US5962140A (en) | 1996-06-25 | 1999-10-05 | Acushnet Company | Golf ball comprising fluoropolymer |
| JPH108009A (ja) * | 1996-06-26 | 1998-01-13 | Elf Atochem Japan Kk | フッ化ビニリデン系樹脂の金属への接着方法およびフッ化ビニリデン系樹脂からなる金属接着性複合材料 |
| KR20000052944A (ko) | 1996-11-01 | 2000-08-25 | 메리 이. 보울러 | 고도의 전도성 이온 교환 중합체 및 제법 |
| US6444343B1 (en) * | 1996-11-18 | 2002-09-03 | University Of Southern California | Polymer electrolyte membranes for use in fuel cells |
| US6025092A (en) * | 1998-02-13 | 2000-02-15 | E. I. Du Pont De Nemours And Company | Fluorinated ionomers and their uses |
| JP4150867B2 (ja) * | 1998-05-13 | 2008-09-17 | ダイキン工業株式会社 | 燃料電池に使用するのに適した固体高分子電解質用材料 |
| US6076720A (en) | 1998-07-22 | 2000-06-20 | Deng; Jinn-Yi | Stapler with staples of different sizes |
| CN1337072A (zh) * | 1998-12-22 | 2002-02-20 | 戴维系统技术公司 | 膜电极组件及其生产方法 |
| US6423784B1 (en) * | 1999-12-15 | 2002-07-23 | 3M Innovative Properties Company | Acid functional fluoropolymer membranes and method of manufacture |
-
2001
- 2001-01-30 US US09/774,266 patent/US6780935B2/en not_active Expired - Lifetime
- 2001-02-15 RU RU2001130757/04A patent/RU2264420C2/ru active
- 2001-02-15 JP JP2001560254A patent/JP4837216B2/ja not_active Expired - Lifetime
- 2001-02-15 KR KR1020017013043A patent/KR100743845B1/ko not_active Expired - Lifetime
- 2001-02-15 CA CA2369696A patent/CA2369696C/en not_active Expired - Lifetime
- 2001-02-15 CN CNB018002137A patent/CN1142193C/zh not_active Expired - Lifetime
- 2001-02-15 MX MXPA01010408A patent/MXPA01010408A/es active IP Right Grant
- 2001-02-15 WO PCT/US2001/004995 patent/WO2001060872A1/en not_active Ceased
- 2001-02-15 EP EP01916103A patent/EP1177221A4/en not_active Withdrawn
- 2001-03-08 TW TW090103434A patent/TWI302540B/zh not_active IP Right Cessation
- 2001-09-25 IL IL145673A patent/IL145673A/en active IP Right Grant
-
2003
- 2003-09-24 US US10/670,095 patent/US6872781B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20040092661A1 (en) | 2004-05-13 |
| US20030064267A1 (en) | 2003-04-03 |
| CA2369696A1 (en) | 2001-08-23 |
| EP1177221A4 (en) | 2006-11-08 |
| KR100743845B1 (ko) | 2007-08-02 |
| CN1142193C (zh) | 2004-03-17 |
| IL145673A (en) | 2009-09-22 |
| JP2003523419A (ja) | 2003-08-05 |
| CA2369696C (en) | 2011-12-13 |
| EP1177221A1 (en) | 2002-02-06 |
| US6780935B2 (en) | 2004-08-24 |
| US6872781B2 (en) | 2005-03-29 |
| JP4837216B2 (ja) | 2011-12-14 |
| CN1362971A (zh) | 2002-08-07 |
| MXPA01010408A (es) | 2002-05-06 |
| WO2001060872A1 (en) | 2001-08-23 |
| RU2264420C2 (ru) | 2005-11-20 |
| IL145673A0 (en) | 2002-06-30 |
| KR20020000798A (ko) | 2002-01-05 |
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