JPS6134725B2 - - Google Patents
Info
- Publication number
- JPS6134725B2 JPS6134725B2 JP54067889A JP6788979A JPS6134725B2 JP S6134725 B2 JPS6134725 B2 JP S6134725B2 JP 54067889 A JP54067889 A JP 54067889A JP 6788979 A JP6788979 A JP 6788979A JP S6134725 B2 JPS6134725 B2 JP S6134725B2
- Authority
- JP
- Japan
- Prior art keywords
- membrane
- group
- carboxylic acid
- film
- fluorinated
- 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
Links
- 229920001577 copolymer Polymers 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 40
- 238000006116 polymerization reaction Methods 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 20
- 239000011593 sulfur Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 150000001336 alkenes Chemical class 0.000 claims description 14
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001451 organic peroxides Chemical class 0.000 claims description 2
- 230000033116 oxidation-reduction process Effects 0.000 claims description 2
- 239000012528 membrane Substances 0.000 description 163
- 125000002843 carboxylic acid group Chemical group 0.000 description 74
- 239000010408 film Substances 0.000 description 51
- 238000005342 ion exchange Methods 0.000 description 40
- 229920000642 polymer Polymers 0.000 description 38
- 125000000542 sulfonic acid group Chemical group 0.000 description 34
- 238000005341 cation exchange Methods 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000003513 alkali Substances 0.000 description 23
- 239000000463 material Substances 0.000 description 23
- 238000000862 absorption spectrum Methods 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 20
- 239000000178 monomer Substances 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 238000005868 electrolysis reaction Methods 0.000 description 19
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- 239000010410 layer Substances 0.000 description 15
- 238000011282 treatment Methods 0.000 description 15
- -1 hydroxyl ions Chemical class 0.000 description 14
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 13
- 239000003638 chemical reducing agent Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 238000007334 copolymerization reaction Methods 0.000 description 11
- 239000002344 surface layer Substances 0.000 description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- 229910001508 alkali metal halide Inorganic materials 0.000 description 7
- 150000008045 alkali metal halides Chemical class 0.000 description 7
- 229940071870 hydroiodic acid Drugs 0.000 description 7
- 230000003301 hydrolyzing effect Effects 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 238000005336 cracking Methods 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000003014 ion exchange membrane Substances 0.000 description 5
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 5
- 229940107698 malachite green Drugs 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 239000005708 Sodium hypochlorite Substances 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- 125000002128 sulfonyl halide group Chemical group 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000004026 adhesive bonding Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- YOALFLHFSFEMLP-UHFFFAOYSA-N azane;2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoic acid Chemical compound [NH4+].[O-]C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YOALFLHFSFEMLP-UHFFFAOYSA-N 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 229940023913 cation exchange resins Drugs 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229920002313 fluoropolymer Polymers 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000012779 reinforcing material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 125000000626 sulfinic acid group Chemical group 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000006886 vinylation reaction Methods 0.000 description 3
- TXGPGHBYAPBDAG-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-4,4-bis(trifluoromethyl)cyclobutane Chemical compound FC(F)(F)C1(C(F)(F)F)C(F)(F)C(F)(F)C1(F)F TXGPGHBYAPBDAG-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229960002446 octanoic acid Drugs 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 230000002522 swelling effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OYGQVDSRYXATEL-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,7-pentadecafluoroheptane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F OYGQVDSRYXATEL-UHFFFAOYSA-N 0.000 description 1
- QIROQPWSJUXOJC-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(trifluoromethyl)cyclohexane Chemical compound FC(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F QIROQPWSJUXOJC-UHFFFAOYSA-N 0.000 description 1
- VQUGQIYAVYQSAB-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-2-(1,2,2-trifluoroethenoxy)ethanesulfonyl fluoride Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)S(F)(=O)=O VQUGQIYAVYQSAB-UHFFFAOYSA-N 0.000 description 1
- KTCQQCLZUOZFEI-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-2-[1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluoroethenoxy)propan-2-yl]oxyethanesulfonyl fluoride Chemical compound FC(F)=C(F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)S(F)(=O)=O KTCQQCLZUOZFEI-UHFFFAOYSA-N 0.000 description 1
- LGPPATCNSOSOQH-UHFFFAOYSA-N 1,1,2,3,4,4-hexafluorobuta-1,3-diene Chemical compound FC(F)=C(F)C(F)=C(F)F LGPPATCNSOSOQH-UHFFFAOYSA-N 0.000 description 1
- QARLOMBMXGVKNV-UHFFFAOYSA-N 1,2,2-trifluoroethenesulfonyl fluoride Chemical compound FC(F)=C(F)S(F)(=O)=O QARLOMBMXGVKNV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
- NHJFHUKLZMQIHN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl 2,2,3,3,3-pentafluoropropaneperoxoate Chemical compound FC(F)(F)C(F)(F)C(=O)OOC(=O)C(F)(F)C(F)(F)F NHJFHUKLZMQIHN-UHFFFAOYSA-N 0.000 description 1
- CCUWGJDGLACFQT-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluoropentanedioic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(O)=O CCUWGJDGLACFQT-UHFFFAOYSA-N 0.000 description 1
- WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 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 1
- 239000005639 Lauric acid Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- PAAZCQANMCYGAW-UHFFFAOYSA-N acetic acid;2,2,2-trifluoroacetic acid Chemical compound CC(O)=O.OC(=O)C(F)(F)F PAAZCQANMCYGAW-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- GCPXMJHSNVMWNM-UHFFFAOYSA-N arsenous acid Chemical compound O[As](O)O GCPXMJHSNVMWNM-UHFFFAOYSA-N 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- AKRQHOWXVSDJEF-UHFFFAOYSA-N heptane-1-sulfonic acid Chemical compound CCCCCCCS(O)(=O)=O AKRQHOWXVSDJEF-UHFFFAOYSA-N 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- RJQRCOMHVBLQIH-UHFFFAOYSA-M pentane-1-sulfonate Chemical compound CCCCCS([O-])(=O)=O RJQRCOMHVBLQIH-UHFFFAOYSA-M 0.000 description 1
- ZWBAMYVPMDSJGQ-UHFFFAOYSA-N perfluoroheptanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZWBAMYVPMDSJGQ-UHFFFAOYSA-N 0.000 description 1
- PXUULQAPEKKVAH-UHFFFAOYSA-N perfluorohexanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F PXUULQAPEKKVAH-UHFFFAOYSA-N 0.000 description 1
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Priority Applications (55)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6788979A JPS55160007A (en) | 1979-05-31 | 1979-05-31 | Novel fluorinated copolymer and production thereof |
| US06/152,856 US4329435A (en) | 1979-05-31 | 1980-05-23 | Novel fluorinated copolymer with tridihydro fluorosulfonyl fluoride pendant groups and preparation thereof |
| US06/152,847 US4329434A (en) | 1979-05-31 | 1980-05-23 | Novel fluorinated cation exchange membrane and process for producing the same |
| DE19803020057 DE3020057A1 (de) | 1979-05-31 | 1980-05-24 | Fluorierte kationenaustauschermembran und verfahren zu ihrer herstelleung |
| DE3050782A DE3050782C2 (US07413550-20080819-C00001.png) | 1979-05-31 | 1980-05-24 | |
| DE3050439A DE3050439C2 (US07413550-20080819-C00001.png) | 1979-05-31 | 1980-05-24 | |
| DE19803046501 DE3046501A1 (de) | 1979-05-31 | 1980-05-24 | Fluorierte organische verbindungen als zwischen- und ausgangsprodukte fuer die herstellung von kationenaustauschermembranen |
| DE3047438A DE3047438C2 (de) | 1979-05-31 | 1980-05-24 | Fluorierte Copolymerisate, ihre Herstellung und Verwendung |
| DE3050634A DE3050634C2 (de) | 1979-05-31 | 1980-05-24 | Perfluorierte Fluorsulfonylsäurefluoride und Verfahren zu ihrer Herstellung |
| DE3050643A DE3050643C2 (US07413550-20080819-C00001.png) | 1979-05-31 | 1980-05-24 | |
| DE3050931A DE3050931C2 (de) | 1979-05-31 | 1980-05-24 | Fluorierte Carbonsäure-Derivate und Verfahren zu ihrer Herstellung |
| DE3020017A DE3020017C2 (de) | 1979-05-31 | 1980-05-24 | Fluorierte Carbonsäuren oder ihre Derivate und Verfahren zu ihrer Herstellung |
| DE19803047439 DE3047439A1 (de) | 1979-05-31 | 1980-05-24 | Fluorierte vinylaetherverbindungen, ihre herstellung und verwendung |
| CA000352704A CA1148566A (en) | 1979-05-31 | 1980-05-26 | Fluorinated copolymer and preparation thereof |
| CA000352671A CA1185398A (en) | 1979-05-31 | 1980-05-26 | Fluorinated cation exchange membrane and process for producing the same |
| SE8003902A SE450000B (sv) | 1979-05-31 | 1980-05-27 | Sett att framstella ett fluorerat katjonbytarmembran innehallande savel karboxyl- som sulfonsyragrupper |
| SE8003901A SE449999B (sv) | 1979-05-31 | 1980-05-27 | Fluorerat katjonbytarmembran innehallande savel karboxyl- som sulfonsyragrupper samt sett for framstellning derav |
| FI801734A FI68847C (fi) | 1979-05-31 | 1980-05-28 | Foerfarande foer framstaellning av ett nytt fluorerat katjonbytarmembran |
| FI801733A FI72530C (fi) | 1979-05-31 | 1980-05-28 | Fluorerat katjonbytarmembran och laminat samt foerfarande foer dess framstaellning. |
| FR8011912A FR2465718B1 (fr) | 1979-05-31 | 1980-05-29 | Acide carboxylique fluore et son procede de preparation |
| BR8003403A BR8003403A (pt) | 1979-05-31 | 1980-05-30 | Acido carboxilico fluorado ou seu derivado,processo de producao de acido carboxilico fluorado ou seu derivado,fluoreto de acido fluorado e processo de producao do mesmo,composto de eter vinilico fluorado e processo de preparacao do composto fluorado,copolimero fluorado e processo de producao de copolimero fluorado e processo para a producao de uma membrana de permuta cationica fluorada |
| GB8017838A GB2053902B (en) | 1979-05-31 | 1980-05-30 | Fluorinated compounds |
| IT8022469A IT1193943B (it) | 1979-05-31 | 1980-05-30 | Copolimero fluorurato e sua preparazione |
| GB08221499A GB2123812B (en) | 1979-05-31 | 1980-05-30 | Fluorinated carboxylic acids and derivatives their production and their use to produce fluorinated acid fluorides |
| NLAANVRAGE8003174,A NL184740C (nl) | 1979-05-31 | 1980-05-30 | Kationuitwisselmembraan op basis van een fluorkoolstofpolymeer alsmede werkwijze voor het vervaardigen daarvan. |
| NO801637A NO153398C (no) | 1979-05-31 | 1980-05-30 | Fluorerte kationbyttermembraner, herunder ogsaa laminerte membraner, og fremgangsmaate ved fremstilling av disse. |
| IT22468/80A IT1193942B (it) | 1979-05-31 | 1980-05-30 | Membrana fluorata a scambio cationico e processo per produrla |
| NLAANVRAGE8003170,A NL187488C (nl) | 1979-05-31 | 1980-05-30 | Gefluoreerd copolymeer alsmede kationuitwisselend membraan dat onder toepassing daarvan is vervaardigd en vinylether geschikt voor de bereiding van het copolymeer. |
| BR8003432A BR8003432A (pt) | 1979-05-31 | 1980-05-30 | Membrana de permuta cationica fluorada e processo para a producao da mesma, copolimero e derivados fluorados que constituem a membrana |
| GB8017804A GB2051831B (en) | 1979-05-31 | 1980-05-30 | Fluorinated copolymers and cation exchange membrane and process for producing the same |
| NO80801636A NO801636L (no) | 1979-05-31 | 1980-05-30 | Fluorert kopolymer og fremstilling derav |
| FR8012213A FR2457880B1 (US07413550-20080819-C00001.png) | 1979-05-31 | 1980-06-02 | |
| FR8024131A FR2463123A1 (fr) | 1979-05-31 | 1980-11-13 | Ether vinylique fluore et son procede de fabrication |
| FR8024747A FR2473533B1 (fr) | 1979-05-31 | 1980-11-21 | Composes fluores, membrane d'echange de cations fluoree et son procede de preparation |
| PT72131A PT72131B (en) | 1979-05-31 | 1980-11-28 | Novel fluorinated copolymer and preparation thereof |
| PT7213080A PT72130B (en) | 1979-05-31 | 1980-11-28 | Novel fluorinated cation exchange membrane and process forproducing the same |
| IN1334/CAL/80A IN154418B (US07413550-20080819-C00001.png) | 1979-05-31 | 1980-12-01 | |
| NO81810161A NO810161L (no) | 1979-05-31 | 1981-01-19 | Fluorerte syrefluorider. |
| NO81810159A NO159174C (no) | 1979-05-31 | 1981-01-19 | Fluorerte kopolymerer, samt fremgangsmaate ved fremstilling derav. |
| NO81810162A NO810162L (no) | 1979-05-31 | 1981-01-19 | Fluorerte vinyleterforbindelser. |
| NO81810160A NO154921C (no) | 1979-05-31 | 1981-01-19 | Fremgangsmaate ved fremstilling av en kationbyttermembran. |
| SU813287151A SU1233804A3 (ru) | 1979-05-31 | 1981-05-25 | Способ получени фторированного сополимера |
| FR8112845A FR2483431B1 (fr) | 1979-05-31 | 1981-06-30 | Copolymere fluore, son procede de preparation et derives fluores et leurs procedes de preparation utiles a la preparation de ce copolymere |
| US06/299,164 US4510328A (en) | 1979-05-31 | 1981-09-03 | Fluorinated vinyl ether compounds and process for producing the same |
| FR8121580A FR2508039B1 (US07413550-20080819-C00001.png) | 1979-05-31 | 1981-11-18 | |
| US06/330,608 US4536352A (en) | 1979-05-31 | 1981-12-14 | Perfluoro vinyl ethers |
| FR8212640A FR2514010B1 (fr) | 1979-05-31 | 1982-07-20 | Copolymere fluore, son procede de preparation et son utilisation dans la preparation d'une membrane d'echange de cations |
| GB08221735A GB2118541B (en) | 1979-05-31 | 1982-07-27 | Fluorinated vinyl ethers and their preparation |
| SU823480338A SU1296007A3 (ru) | 1979-05-31 | 1982-08-19 | Способ получени фторированной катионообменной мембраны |
| CA000432138A CA1168263A (en) | 1979-05-31 | 1983-07-08 | Fluorinated cation exchange membrane and process for producing the same |
| US06/527,425 US4555369A (en) | 1979-05-31 | 1983-08-29 | Fluorinated ether acyl fluorides having alkylthio or alkylsulfone groups |
| US06/527,426 US4597913A (en) | 1979-05-31 | 1983-08-29 | Intermediates for fluorinated cation exchange membrane |
| US06/527,746 US4613467A (en) | 1979-05-31 | 1983-08-30 | Fluorosulfonylperfluoroalkyl compounds |
| US06/527,818 US4511518A (en) | 1979-05-31 | 1983-08-30 | Perfluorinated fluorosulfonylalkyleneoxy-2-propanoyl fluoride and hexafluoroepoxide addition compounds |
| SU864027511A SU1729295A3 (ru) | 1979-05-31 | 1986-05-26 | Способ получени фторсодержащего сополимера дл синтеза ионообменных мембран |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6788979A JPS55160007A (en) | 1979-05-31 | 1979-05-31 | Novel fluorinated copolymer and production thereof |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17031579A Division JPS55160008A (en) | 1979-05-31 | 1979-12-28 | Fluorinated copolymer and production thereof |
| JP5175580A Division JPS55160030A (en) | 1980-04-21 | 1980-04-21 | Sulfonic group-containing fluorinated cation exchange membrane and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55160007A JPS55160007A (en) | 1980-12-12 |
| JPS6134725B2 true JPS6134725B2 (US07413550-20080819-C00001.png) | 1986-08-09 |
Family
ID=13357905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6788979A Granted JPS55160007A (en) | 1979-05-31 | 1979-05-31 | Novel fluorinated copolymer and production thereof |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS55160007A (US07413550-20080819-C00001.png) |
| SU (3) | SU1233804A3 (US07413550-20080819-C00001.png) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5815947A (ja) * | 1981-07-02 | 1983-01-29 | イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− | β−置換ポリフルオロプロピオネ−ト塩及びその誘導体 |
| US4474700A (en) * | 1981-07-02 | 1984-10-02 | E. I. Du Pont DeNemours and Company | β-Substituted polyfluoropropionate salts and derivatives |
| US6365693B1 (en) * | 1999-05-07 | 2002-04-02 | Dupont Dow Elastomers, L.L.C. | Fluoroalkanesulfonyl azide copolymers |
| RU2348649C1 (ru) * | 2007-12-20 | 2009-03-10 | Институт катализа имени Г.К. Борескова Сибирского отделения Российской академии наук (статус государственного учреждения) | Способ получения перфторированного сополимера, содержащего функциональные группы |
| RU2454431C1 (ru) * | 2011-02-07 | 2012-06-27 | Учреждение Российской академии наук Институт катализа им. Г.К. Борескова Сибирского отделения РАН | Способ получения перфторированного функционализированного сополимера методом эмульсионной сополимеризации |
-
1979
- 1979-05-31 JP JP6788979A patent/JPS55160007A/ja active Granted
-
1981
- 1981-05-25 SU SU813287151A patent/SU1233804A3/ru active
-
1982
- 1982-08-19 SU SU823480338A patent/SU1296007A3/ru active
-
1986
- 1986-05-26 SU SU864027511A patent/SU1729295A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| SU1296007A3 (ru) | 1987-03-07 |
| JPS55160007A (en) | 1980-12-12 |
| SU1233804A3 (ru) | 1986-05-23 |
| SU1729295A3 (ru) | 1992-04-23 |
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