GB1571356A - Polyfluoroallyloxy compounds their preparation and copolymers therefrom - Google Patents
Polyfluoroallyloxy compounds their preparation and copolymers therefrom Download PDFInfo
- Publication number
- GB1571356A GB1571356A GB50394/77A GB5039477A GB1571356A GB 1571356 A GB1571356 A GB 1571356A GB 50394/77 A GB50394/77 A GB 50394/77A GB 5039477 A GB5039477 A GB 5039477A GB 1571356 A GB1571356 A GB 1571356A
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- GB
- United Kingdom
- Prior art keywords
- mol
- fluoride
- compound
- copolymer
- so2f
- 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
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- 229920001577 copolymer Polymers 0.000 title claims description 59
- 150000001875 compounds Chemical class 0.000 title claims description 30
- 238000002360 preparation method Methods 0.000 title description 10
- 239000000203 mixture Substances 0.000 claims description 71
- -1 -CO2R Chemical group 0.000 claims description 46
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 34
- 229910006095 SO2F Inorganic materials 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 21
- 239000000178 monomer Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 8
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 7
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 150000001336 alkenes Chemical group 0.000 claims description 4
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000003014 ion exchange membrane Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000012360 testing method Methods 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000000047 product Substances 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000011698 potassium fluoride Substances 0.000 description 29
- LIZZWVXXYAALGG-UHFFFAOYSA-N 1,1,2,3,3-pentafluoro-3-fluorosulfonyloxyprop-1-ene Chemical compound FC(F)=C(F)C(F)(F)OS(F)(=O)=O LIZZWVXXYAALGG-UHFFFAOYSA-N 0.000 description 26
- 235000003270 potassium fluoride Nutrition 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 21
- 238000004293 19F NMR spectroscopy Methods 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 239000010410 layer Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 13
- 150000001450 anions Chemical class 0.000 description 13
- 238000004821 distillation Methods 0.000 description 13
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 13
- KQAPHIQIAHGITH-UHFFFAOYSA-N 1,2,2,2-tetrafluoroethanesulfonyl fluoride Chemical compound FC(F)(F)C(F)S(F)(=O)=O KQAPHIQIAHGITH-UHFFFAOYSA-N 0.000 description 12
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000000113 differential scanning calorimetry Methods 0.000 description 11
- 239000004810 polytetrafluoroethylene Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 10
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 10
- 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 9
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 229910001512 metal fluoride Inorganic materials 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 150000002222 fluorine compounds Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- OQUQGPIATTWEFF-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6-decafluoro-6-(1,1,2,3,3-pentafluoroprop-2-enoxy)hexanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)=C(F)F OQUQGPIATTWEFF-UHFFFAOYSA-N 0.000 description 6
- DQWRXSPZQZNYRX-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropanoyl fluoride Chemical compound FC(F)C(F)(F)C(F)=O DQWRXSPZQZNYRX-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 238000006073 displacement reaction Methods 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- ZMIDKLPSOSQFSX-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluorobutane-2,3-dione Chemical compound FC(F)(F)C(=O)C(=O)C(F)(F)F ZMIDKLPSOSQFSX-UHFFFAOYSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- TZLOXHKLJUZTLW-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,6-bis(1,1,2,3,3-pentafluoroprop-2-enoxy)hexane Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)=C(F)F TZLOXHKLJUZTLW-UHFFFAOYSA-N 0.000 description 4
- JGEWGXVFZFMKMC-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-1,3-bis(1,1,2,3,3-pentafluoroprop-2-enoxy)propane Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)=C(F)F JGEWGXVFZFMKMC-UHFFFAOYSA-N 0.000 description 4
- RJYJDEJAFADMLE-UHFFFAOYSA-N 1-chloro-1,1,2,3,3,3-hexafluoro-2-(1,1,2,3,3-pentafluoroprop-2-enoxy)propane Chemical compound FC(F)=C(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)Cl RJYJDEJAFADMLE-UHFFFAOYSA-N 0.000 description 4
- KJOOJFLEZNWPIN-UHFFFAOYSA-N 2,2-difluoropropanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(F)=O KJOOJFLEZNWPIN-UHFFFAOYSA-N 0.000 description 4
- SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 description 4
- LLBCDOYDDNKNSQ-UHFFFAOYSA-N 2-ethoxy-1,1,3,3,3-pentafluoroprop-1-ene Chemical compound CCOC(=C(F)F)C(F)(F)F LLBCDOYDDNKNSQ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 229920002313 fluoropolymer Polymers 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- 238000004876 x-ray fluorescence Methods 0.000 description 4
- URXYEXLEZZBAIX-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-(1,1,2,3,3-pentafluoroprop-2-enoxy)butane Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)F URXYEXLEZZBAIX-UHFFFAOYSA-N 0.000 description 3
- GEWFYVHBZSLJEZ-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-2-(1,1,2,3,3-pentafluoroprop-2-enoxy)ethanesulfonyl fluoride Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)S(F)(=O)=O GEWFYVHBZSLJEZ-UHFFFAOYSA-N 0.000 description 3
- LIJKQESROBUSFB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoro-2-oxopropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(=O)C(F)(F)F LIJKQESROBUSFB-UHFFFAOYSA-N 0.000 description 3
- FDGCJTUAVVJFMB-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluorohexanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)=O FDGCJTUAVVJFMB-UHFFFAOYSA-N 0.000 description 3
- YIHXQSQQJBEAKK-UHFFFAOYSA-N 2,2-difluoro-2-fluorosulfonylacetyl fluoride Chemical compound FC(=O)C(F)(F)S(F)(=O)=O YIHXQSQQJBEAKK-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- IWYWYPXNZJXKNS-UHFFFAOYSA-N ethyl 1,1,3,3,3-pentafluoro-2-oxopropane-1-sulfonate Chemical compound CCOS(=O)(=O)C(F)(F)C(=O)C(F)(F)F IWYWYPXNZJXKNS-UHFFFAOYSA-N 0.000 description 3
- IYRWEQXVUNLMAY-UHFFFAOYSA-N fluoroketone group Chemical group FC(=O)F IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- IJEKHZDQURMSCF-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-8-(1,1,2,3,3-pentafluoroprop-2-enoxy)octane Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F IJEKHZDQURMSCF-UHFFFAOYSA-N 0.000 description 2
- CYCMWTZDJDCPLG-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)-3-(1,1,2,3,3-pentafluoroprop-2-enoxy)propane Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F CYCMWTZDJDCPLG-UHFFFAOYSA-N 0.000 description 2
- MHNPWFZIRJMRKC-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical compound F[C]=C(F)F MHNPWFZIRJMRKC-UHFFFAOYSA-N 0.000 description 2
- SBGSGDOEAAWCJN-UHFFFAOYSA-N 1,1-difluoroethyl 1,1,3,3,3-pentafluoro-2-oxopropane-1-sulfonate Chemical compound CC(F)(F)OS(=O)(=O)C(F)(F)C(=O)C(F)(F)F SBGSGDOEAAWCJN-UHFFFAOYSA-N 0.000 description 2
- OJUUDWYPNQALHZ-UHFFFAOYSA-N 1-chloro-1,1,3,3,3-pentafluoropropan-2-one Chemical compound FC(F)(F)C(=O)C(F)(F)Cl OJUUDWYPNQALHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YYXWJNBPHDUWJP-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)F YYXWJNBPHDUWJP-UHFFFAOYSA-N 0.000 description 2
- ZILWJLIFAGWGLE-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZILWJLIFAGWGLE-UHFFFAOYSA-N 0.000 description 2
- CLZVMMVCWAKKHN-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoro-5-(1,1,2,3,3-pentafluoroprop-2-enoxy)pentanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(F)C(F)=C(F)F CLZVMMVCWAKKHN-UHFFFAOYSA-N 0.000 description 2
- XXNILTDSQBSKJO-UHFFFAOYSA-N 2,2-difluoro-2-(1,1,2-trifluoro-2-oxoethoxy)acetyl fluoride Chemical compound FC(=O)C(F)(F)OC(F)(F)C(F)=O XXNILTDSQBSKJO-UHFFFAOYSA-N 0.000 description 2
- FYTXVNDCFYQKEO-UHFFFAOYSA-N 2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(1,1,2,3,3-pentafluoroprop-2-enoxy)ethoxy]acetyl fluoride Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)OC(F)(F)C(F)=O FYTXVNDCFYQKEO-UHFFFAOYSA-N 0.000 description 2
- GNXIPZJHEFTGNR-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-fluorosulfonylpropanoyl fluoride Chemical compound FC(=O)C(F)(C(F)(F)F)S(F)(=O)=O GNXIPZJHEFTGNR-UHFFFAOYSA-N 0.000 description 2
- SVEMUCQZCCOMSZ-UHFFFAOYSA-N 2-(2-chloro-1,1,3,3-tetrafluoroprop-2-enoxy)-1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)=C(Cl)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)F SVEMUCQZCCOMSZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IJTAKAGEJXIJPQ-UHFFFAOYSA-N 3-chloro-1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=C(F)C(F)(F)Cl IJTAKAGEJXIJPQ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/78—Halides of sulfonic acids
- C07C309/79—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms
- C07C309/82—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms of a carbon skeleton substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/36—Acyl halides
- C07C55/40—Acyl halides containing halogen outside the carboxyl halide group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
- C07C59/315—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/60—Unsaturated compounds containing ether groups, groups, groups, or groups the non-carboxylic part of the ether being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US74702976A | 1976-12-02 | 1976-12-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1571356A true GB1571356A (en) | 1980-07-16 |
Family
ID=25003378
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB50394/77A Expired GB1571356A (en) | 1976-12-02 | 1977-12-02 | Polyfluoroallyloxy compounds their preparation and copolymers therefrom |
Country Status (15)
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4474700A (en) * | 1981-07-02 | 1984-10-02 | E. I. Du Pont DeNemours and Company | β-Substituted polyfluoropropionate salts and derivatives |
WO2004018553A3 (en) * | 2002-06-20 | 2004-09-16 | Pcbu Services Inc | Methods for preparing ethers, halogenated ethers, fluoroethers as well as uses of the latter in fire extinguishing systems. |
WO2009094348A1 (en) * | 2008-01-23 | 2009-07-30 | 3M Innovative Properties Company | Processing aid compositions comprising fluoropolymers having long-chain branches |
CN109563206A (zh) * | 2016-08-17 | 2019-04-02 | 3M创新有限公司 | 四氟乙烯和全氟化烯丙基醚共聚物 |
CN109641991A (zh) * | 2016-08-17 | 2019-04-16 | 3M创新有限公司 | 包含四氟乙烯和一种或多种全氟化烷基烯丙基醚共聚单体的含氟聚合物 |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2027709B (en) * | 1978-08-08 | 1983-01-06 | Du Pont | Perfluoroallyl fluorosulphate and its sultone and processes for their preparation |
IT1125484B (it) * | 1979-03-14 | 1986-05-14 | Du Pont | Composti polifluorallilossilici,loro preparazione e copolimeri da essi ottenuti |
JPS5629685A (en) * | 1979-08-14 | 1981-03-25 | Asahi Glass Co Ltd | Fluorine containing cation exchange membrane for electrolysis |
DE3034550A1 (de) * | 1980-09-12 | 1982-04-29 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von perfluorcarbonylsulfonsaeurefluoriden sowei die dabei als zwischenprodukte auftretenden fluorsulfatoperfluoralkansulfonsaeurehalogenide und einige spezielle perfluorcarbonylsulfonsaeurefluoride |
US4334082A (en) | 1980-09-26 | 1982-06-08 | E. I. Du Pont De Nemours And Company | Dialkyl perfluoro-ω-fluoroformyl diesters and monomers and polymers therefrom |
US4414159A (en) | 1980-09-26 | 1983-11-08 | E. I. Du Pont De Nemours & Co. | Vinyl ether monomers and polymers therefrom |
JPS6189813U (enrdf_load_stackoverflow) * | 1984-11-19 | 1986-06-11 | ||
JPS6259610A (ja) * | 1985-09-10 | 1987-03-16 | Tokuyama Soda Co Ltd | 架橋構造を有する含フツ素系樹脂の製造方法 |
JPH0660125B2 (ja) * | 1989-08-03 | 1994-08-10 | 信越化学工業株式会社 | 含フッ素カルボン酸誘導体及びその製造方法 |
US5264508A (en) * | 1992-06-25 | 1993-11-23 | The Dow Chemical Company | Polymers of haloperfluoro and perfluoro ethers |
IT1318594B1 (it) * | 2000-06-23 | 2003-08-27 | Ausimont Spa | Processo di polimerizzazione di monomeri solfonici. |
AU2001292268A1 (en) * | 2000-09-27 | 2002-04-08 | Asahi Glass Company, Limited | Process for producing fluorinated ester compound |
ATE520642T1 (de) * | 2000-09-27 | 2011-09-15 | Asahi Glass Co Ltd | Verfahren zur herstellung einer fluorinierten polyvalenten carbonylverbindung |
JP4848587B2 (ja) * | 2001-01-26 | 2011-12-28 | 旭硝子株式会社 | 固体高分子型燃料電池用電解質材料とその製造方法、及び固体高分子型燃料電池 |
WO2004056887A1 (ja) | 2002-12-19 | 2004-07-08 | Asahi Glass Company, Limited | テトラフルオロエチレン共重合体 |
RU2320642C1 (ru) * | 2006-11-16 | 2008-03-27 | Федеральное государственное унитарное предприятие "Научно-исследовательский институт синтетического каучука им. акад. С.В. Лебедева" | Способ получения перфтораллилфторсульфата |
JP5217708B2 (ja) * | 2008-07-09 | 2013-06-19 | 旭硝子株式会社 | ポリマー、その製造方法、固体高分子形燃料電池用電解質膜および膜電極接合体 |
CN104885272B (zh) | 2012-11-14 | 2017-10-13 | 旭硝子株式会社 | 离子性聚合物膜的制造方法 |
KR20150016133A (ko) * | 2013-08-02 | 2015-02-11 | 주식회사 엘지화학 | 광반응성 화합물의 정제 방법 및 광반응성 화합물 |
US11292763B2 (en) | 2017-05-19 | 2022-04-05 | 3M Innovative Properties Company | Methods of making a polyfluorinated allyl ether and compounds relating to the methods |
CN111133015B (zh) | 2017-09-14 | 2022-09-06 | 3M创新有限公司 | 含氟聚合物分散体、用于制备含氟聚合物分散体的方法、催化剂油墨和聚合物电解质膜 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2852554A (en) * | 1956-07-12 | 1958-09-16 | Du Pont | Alpha-sulfopolyfluoromonocarboxylic acids and derivatives hydrolyzable thereto |
US2975163A (en) * | 1956-10-29 | 1961-03-14 | Minnesota Mining & Mfg | Fluorine containing organic compounds and preparation thereof |
US3541159A (en) * | 1965-02-18 | 1970-11-17 | Us Agriculture | Fluorinated allyl ethers and use thereof |
US3465045A (en) * | 1965-02-18 | 1969-09-02 | Us Agriculture | Fluorinated vinyl ethers and use thereof |
US3925135A (en) * | 1971-11-08 | 1975-12-09 | Du Pont | Method of making laminates of support material and fluorinated polymer containing pendant side chains containing sulfonyl groups |
JPS551351B2 (enrdf_load_stackoverflow) * | 1974-03-07 | 1980-01-12 |
-
1977
- 1977-11-14 SE SE7712836A patent/SE7712836L/xx not_active Application Discontinuation
- 1977-11-30 FR FR7736067A patent/FR2390430A1/fr active Pending
- 1977-12-01 BR BR7708025A patent/BR7708025A/pt unknown
- 1977-12-01 IT IT30289/77A patent/IT1089314B/it active
- 1977-12-01 ZA ZA00777158A patent/ZA777158B/xx unknown
- 1977-12-01 NL NL7713275A patent/NL7713275A/xx not_active Application Discontinuation
- 1977-12-01 IL IL53504A patent/IL53504A/xx unknown
- 1977-12-01 NZ NZ185830A patent/NZ185830A/xx unknown
- 1977-12-01 MX MX171540A patent/MX147703A/es unknown
- 1977-12-02 DE DE2760046A patent/DE2760046C2/de not_active Expired
- 1977-12-02 AU AU31169/77A patent/AU509777B2/en not_active Expired
- 1977-12-02 JP JP52144066A patent/JPS5943936B2/ja not_active Expired
- 1977-12-02 DE DE19772753886 patent/DE2753886A1/de not_active Ceased
- 1977-12-02 SU SU772550560A patent/SU795452A3/ru active
- 1977-12-02 GB GB50394/77A patent/GB1571356A/en not_active Expired
- 1977-12-02 BE BE183109A patent/BE861430A/xx not_active IP Right Cessation
-
1978
- 1978-07-25 FR FR7821942A patent/FR2388061A1/fr active Granted
-
1981
- 1981-05-06 IL IL62812A patent/IL62812A0/xx unknown
- 1981-05-08 FR FR8109180A patent/FR2478625B1/fr not_active Expired
- 1981-06-22 JP JP56095424A patent/JPS5762249A/ja active Granted
-
1982
- 1982-11-24 JP JP57204723A patent/JPS5891708A/ja active Pending
- 1982-11-24 JP JP57204724A patent/JPS5896630A/ja active Granted
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4474700A (en) * | 1981-07-02 | 1984-10-02 | E. I. Du Pont DeNemours and Company | β-Substituted polyfluoropropionate salts and derivatives |
US6849194B2 (en) | 2000-11-17 | 2005-02-01 | Pcbu Services, Inc. | Methods for preparing ethers, ether compositions, fluoroether fire extinguishing systems, mixtures and methods |
WO2004018553A3 (en) * | 2002-06-20 | 2004-09-16 | Pcbu Services Inc | Methods for preparing ethers, halogenated ethers, fluoroethers as well as uses of the latter in fire extinguishing systems. |
WO2009094348A1 (en) * | 2008-01-23 | 2009-07-30 | 3M Innovative Properties Company | Processing aid compositions comprising fluoropolymers having long-chain branches |
CN101959964B (zh) * | 2008-01-23 | 2012-10-10 | 3M创新有限公司 | 包含具有长支链的含氟聚合物的加工助剂组合物 |
CN109563206A (zh) * | 2016-08-17 | 2019-04-02 | 3M创新有限公司 | 四氟乙烯和全氟化烯丙基醚共聚物 |
CN109641991A (zh) * | 2016-08-17 | 2019-04-16 | 3M创新有限公司 | 包含四氟乙烯和一种或多种全氟化烷基烯丙基醚共聚单体的含氟聚合物 |
US20190185599A1 (en) * | 2016-08-17 | 2019-06-20 | 3M Innovative Properties Company | Fluoropolymers comprising tetrafluoroethylene and one or more perfluorinated alkyl allyl ether comonomers |
US20190202951A1 (en) * | 2016-08-17 | 2019-07-04 | 3M Innovative Properties Company | Tetrafluoroethylene and perfluorinated allyl ether copolymers |
US11028198B2 (en) * | 2016-08-17 | 2021-06-08 | 3M Innovative Properties Company | Tetrafluoroethylene and perfluorinated allyl ether copolymers |
Also Published As
Publication number | Publication date |
---|---|
FR2388061B1 (enrdf_load_stackoverflow) | 1984-01-13 |
JPS6345737B2 (enrdf_load_stackoverflow) | 1988-09-12 |
JPS5896630A (ja) | 1983-06-08 |
IT1089314B (it) | 1985-06-18 |
MX147703A (es) | 1983-01-06 |
JPS6314707B2 (enrdf_load_stackoverflow) | 1988-04-01 |
SE7712836L (sv) | 1978-06-03 |
AU3116977A (en) | 1979-06-07 |
NL7713275A (nl) | 1978-06-06 |
BR7708025A (pt) | 1978-08-08 |
IL53504A (en) | 1982-07-30 |
ZA777158B (en) | 1978-09-27 |
SU795452A3 (ru) | 1981-01-07 |
AU509777B2 (en) | 1980-05-22 |
FR2478625B1 (enrdf_load_stackoverflow) | 1983-12-23 |
FR2388061A1 (fr) | 1978-11-17 |
JPS5943936B2 (ja) | 1984-10-25 |
DE2760046C2 (enrdf_load_stackoverflow) | 1988-07-21 |
NZ185830A (en) | 1980-05-08 |
JPS5382713A (en) | 1978-07-21 |
IL53504A0 (en) | 1978-03-10 |
DE2753886A1 (de) | 1978-06-08 |
IL62812A0 (en) | 1981-07-31 |
FR2390430A1 (fr) | 1978-12-08 |
JPS5891708A (ja) | 1983-05-31 |
BE861430A (fr) | 1978-06-02 |
JPS5762249A (en) | 1982-04-15 |
FR2478625A1 (enrdf_load_stackoverflow) | 1981-09-25 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19931202 |