JP5866375B2 - スルフィネート含有分子を含むフッ素含有ポリマー - Google Patents
スルフィネート含有分子を含むフッ素含有ポリマー Download PDFInfo
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- JP5866375B2 JP5866375B2 JP2013544803A JP2013544803A JP5866375B2 JP 5866375 B2 JP5866375 B2 JP 5866375B2 JP 2013544803 A JP2013544803 A JP 2013544803A JP 2013544803 A JP2013544803 A JP 2013544803A JP 5866375 B2 JP5866375 B2 JP 5866375B2
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- Prior art keywords
- sulfinate
- polymerization
- polymer
- monomer
- reaction vessel
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- 229920000642 polymer Polymers 0.000 title claims description 78
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 title claims description 55
- 229910052731 fluorine Inorganic materials 0.000 title claims description 45
- 239000011737 fluorine Substances 0.000 title claims description 22
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 21
- 239000000178 monomer Substances 0.000 claims description 74
- 238000006116 polymerization reaction Methods 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 34
- 150000001768 cations Chemical class 0.000 claims description 18
- 125000005647 linker group Chemical group 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 11
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 77
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 46
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 43
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- -1 but not limited to Chemical class 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 239000003999 initiator Substances 0.000 description 22
- 239000007787 solid Substances 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 15
- HPTMZNZYFRTOKS-UHFFFAOYSA-N ethenesulfinic acid Chemical compound OS(=O)C=C HPTMZNZYFRTOKS-UHFFFAOYSA-N 0.000 description 14
- 229910052740 iodine Inorganic materials 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 150000001336 alkenes Chemical class 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- 229910052757 nitrogen Chemical group 0.000 description 12
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229920001973 fluoroelastomer Polymers 0.000 description 11
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 11
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 10
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000001301 oxygen Chemical group 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 230000008023 solidification Effects 0.000 description 10
- 238000007711 solidification Methods 0.000 description 10
- 229920002313 fluoropolymer Polymers 0.000 description 9
- 239000004811 fluoropolymer Substances 0.000 description 9
- 239000004816 latex Substances 0.000 description 8
- 229920000126 latex Polymers 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 7
- 101150065749 Churc1 gene Proteins 0.000 description 7
- 102100038239 Protein Churchill Human genes 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 150000001993 dienes Chemical group 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 238000007720 emulsion polymerization reaction Methods 0.000 description 5
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- JDGPSBBNVTVFIF-UHFFFAOYSA-N 1,1,3,4,4,5,6,6,6-nonafluoro-5-(trifluoromethyl)hex-1-ene Chemical compound FC(C(C(F)(F)F)(C(C(C=C(F)F)F)(F)F)F)(F)F JDGPSBBNVTVFIF-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 125000002015 acyclic group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 3
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 3
- 235000019797 dipotassium phosphate Nutrition 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 125000005385 peroxodisulfate group Chemical group 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000012488 sample solution Substances 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical group [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical group CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- QTBSBXVTEAMEQO-GUEYOVJQSA-N acetic acid-d4 Chemical compound [2H]OC(=O)C([2H])([2H])[2H] QTBSBXVTEAMEQO-GUEYOVJQSA-N 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000004202 carbamide Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005100 correlation spectroscopy Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000004815 dispersion polymer Substances 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- CVMIVKAWUQZOBP-UHFFFAOYSA-L manganic acid Chemical class O[Mn](O)(=O)=O CVMIVKAWUQZOBP-UHFFFAOYSA-L 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 238000000518 rheometry Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000012056 semi-solid material Substances 0.000 description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-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
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- XYFRHHAYSXIKGH-UHFFFAOYSA-N 3-(5-methoxy-2-methoxycarbonyl-1h-indol-3-yl)prop-2-enoic acid Chemical compound C1=C(OC)C=C2C(C=CC(O)=O)=C(C(=O)OC)NC2=C1 XYFRHHAYSXIKGH-UHFFFAOYSA-N 0.000 description 1
- KJEONMGHBKGXCE-UHFFFAOYSA-N 3-bromo-2-chloro-1,1,3,4,4,5,6,6,7,8,8,9,10,10,10-pentadecafluoro-9-(trifluoromethyl)dec-1-ene Chemical compound FC(C(C(F)(F)F)(C(C(C(C(C(C(C(=C(F)F)Cl)(F)Br)(F)F)F)(F)F)F)(F)F)F)(F)F KJEONMGHBKGXCE-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical class [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241001441571 Hiodontidae Species 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 229910006095 SO2F Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical class [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- YGSFNCRAZOCNDJ-TXHXQZCNSA-N [2H]C(C(=O)C([2H])([2H])[2H])([2H])[2H].CC(=O)C Chemical class [2H]C(C(=O)C([2H])([2H])[2H])([2H])[2H].CC(=O)C YGSFNCRAZOCNDJ-TXHXQZCNSA-N 0.000 description 1
- PDAVOLCVHOKLEO-UHFFFAOYSA-N acetyl benzenecarboperoxoate Chemical compound CC(=O)OOC(=O)C1=CC=CC=C1 PDAVOLCVHOKLEO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical class ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000006085 branching agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- IWTBWSGPDGPTIB-UHFFFAOYSA-N butanoyl butaneperoxoate Chemical compound CCCC(=O)OOC(=O)CCC IWTBWSGPDGPTIB-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
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- 238000012937 correction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Chemical class CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003534 oscillatory effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-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)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000005342 perphosphate group Chemical group 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical compound CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229910052709 silver Chemical class 0.000 description 1
- 239000004332 silver Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F228/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
- C08F228/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur by a bond to sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
- C07C313/04—Sulfinic acids; Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/182—Monomers containing fluorine not covered by the groups C08F214/20 - C08F214/28
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201061424109P | 2010-12-17 | 2010-12-17 | |
| US61/424,109 | 2010-12-17 | ||
| PCT/US2011/065339 WO2012083107A2 (en) | 2010-12-17 | 2011-12-16 | Fluorine-containing polymer comprising a sulfinate-containing molecule |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013545880A JP2013545880A (ja) | 2013-12-26 |
| JP2013545880A5 JP2013545880A5 (OSRAM) | 2015-01-15 |
| JP5866375B2 true JP5866375B2 (ja) | 2016-02-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013544803A Active JP5866375B2 (ja) | 2010-12-17 | 2011-12-16 | スルフィネート含有分子を含むフッ素含有ポリマー |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US10093761B2 (OSRAM) |
| EP (1) | EP2651990B1 (OSRAM) |
| JP (1) | JP5866375B2 (OSRAM) |
| CN (1) | CN103261242B (OSRAM) |
| WO (1) | WO2012083107A2 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014504293A (ja) * | 2010-12-17 | 2014-02-20 | スリーエム イノベイティブ プロパティズ カンパニー | 高度フッ素化スルフィン酸のオリゴマー及びコオリゴマー並びにその塩類 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103582627B (zh) * | 2011-06-03 | 2016-08-31 | 3M创新有限公司 | 烯丙基醚封端的氟代烷基亚磺酸及其盐 |
| EP2791240B1 (en) * | 2011-12-16 | 2018-01-24 | 3M Innovative Properties Company | Processing aid composition derived from a sulfinate-containing molecule |
| EP2684942A1 (en) * | 2012-07-10 | 2014-01-15 | The Swatch Group Research and Development Ltd. | Agent for the surface epilamization of an article |
| WO2014062469A1 (en) * | 2012-10-18 | 2014-04-24 | 3M Innovative Properties Company | Fluoroiodo compounds for fluoropolymers |
| ES2951768T3 (es) | 2017-06-30 | 2023-10-24 | Solvay Specialty Polymers It | Método para fabricar polímeros parcialmente fluorados |
| FR3110168B1 (fr) | 2020-05-15 | 2022-08-26 | Arkema France | Procédé pour produire des polymères à base de fluorure de vinylidène thermiquement stables et hautement cristallins |
| JPWO2023210820A1 (OSRAM) * | 2022-04-28 | 2023-11-02 |
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| FR2388013B1 (fr) * | 1977-04-20 | 1985-08-02 | Du Pont | Polymeres fluores echangeurs d'ions contenant des groupes carboxyliques, leur preparation et leur utilisation dans des cellules d'electrolyse chlore-alcali |
| US4544458A (en) * | 1978-11-13 | 1985-10-01 | E. I. Du Pont De Nemours And Company | Fluorinated ion exchange polymer containing carboxylic groups, process for making same, and film and membrane thereof |
| JPS55160028A (en) * | 1979-05-31 | 1980-12-12 | Asahi Chem Ind Co Ltd | Improved fluorinated cation exchange membrane and production thereof |
| JPS5792028A (en) * | 1980-11-29 | 1982-06-08 | Asahi Chem Ind Co Ltd | Fluorocarbon cation exchange membrane |
| JPS57128703A (en) * | 1981-02-02 | 1982-08-10 | Tokuyama Soda Co Ltd | Treating method of fluorine-containing compound |
| US4940525A (en) * | 1987-05-08 | 1990-07-10 | The Dow Chemical Company | Low equivalent weight sulfonic fluoropolymers |
| JPH02213488A (ja) * | 1989-02-14 | 1990-08-24 | Asahi Glass Co Ltd | 塩化アルカリの電解方法 |
| JPH0632918A (ja) * | 1992-07-17 | 1994-02-08 | Asahi Glass Co Ltd | バイポーラ膜の製造方法 |
| US5285002A (en) | 1993-03-23 | 1994-02-08 | Minnesota Mining And Manufacturing Company | Fluorine-containing polymers and preparation and use thereof |
| IT1265461B1 (it) | 1993-12-29 | 1996-11-22 | Ausimont Spa | Fluoroelastomeri comprendenti unita' monomeriche derivanti da una bis-olefina |
| JP3806941B2 (ja) * | 1995-06-30 | 2006-08-09 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 含フッ素重合体の製造方法 |
| US6002055A (en) | 1996-02-23 | 1999-12-14 | E. I. Du Pont De Nemours And Company | Process for making dihalodifluoromethanes and their homologues |
| US6462228B1 (en) * | 1997-12-22 | 2002-10-08 | 3M Innovative Properties Company | Process for preparation of fluorinated sulfinates |
| CN1119870C (zh) * | 2000-08-09 | 2003-08-27 | 华为技术有限公司 | 自适应数字抖动信号控制方法和利用该方法的中频发射机 |
| US20040039142A1 (en) * | 2001-12-06 | 2004-02-26 | Yang Zhen Yu | Fluorinated ionic polymers |
| US6624328B1 (en) | 2002-12-17 | 2003-09-23 | 3M Innovative Properties Company | Preparation of perfluorinated vinyl ethers having a sulfonyl fluoride end-group |
| AU2003289359A1 (en) * | 2002-12-19 | 2004-07-14 | Asahi Glass Company, Limited | Tetrafluoroethylene copolymer |
| EP1462465B1 (en) * | 2003-03-25 | 2012-02-22 | 3M Innovative Properties Company | Melt-processible thermoplastic fluoropolymers having improved processing characteristics and method of producing the same |
| JP4827372B2 (ja) * | 2003-04-24 | 2011-11-30 | ダイキン工業株式会社 | ポリテトラフルオロエチレン系樹脂製チューブ及びその製造方法 |
| US7375157B2 (en) | 2003-06-09 | 2008-05-20 | 3M Innovative Properties Company | Melt-processible polymer composition comprising fluoropolymer having long chain branches |
| DE602004017604D1 (de) * | 2004-09-09 | 2008-12-18 | 3M Innovative Properties Co | Fluoropolymer zur Herstellung von einem Fluoroelastomer |
| JP2006131588A (ja) * | 2004-11-09 | 2006-05-25 | Asahi Kasei Corp | 含フッ素スルフィン酸塩の製造方法 |
| US20070015937A1 (en) | 2005-07-15 | 2007-01-18 | 3M Innovative Properties Company | Process for recovery of fluorinated carboxylic acid surfactants from exhaust gas |
| US7754795B2 (en) | 2006-05-25 | 2010-07-13 | 3M Innovative Properties Company | Coating composition |
| CN101573315B (zh) * | 2006-12-29 | 2013-05-29 | 3M创新有限公司 | 长链聚亚甲基卤调聚物 |
| US9040646B2 (en) * | 2007-10-04 | 2015-05-26 | W. L. Gore & Associates, Inc. | Expandable TFE copolymers, methods of making, and porous, expanded articles thereof |
| US20090124755A1 (en) * | 2007-11-09 | 2009-05-14 | Dupont Performance Elastomers L.L.C. | Process for producing fluoropolymers |
| CN101721922B (zh) * | 2008-07-22 | 2011-12-28 | 山东华夏神舟新材料有限公司 | 一种微孔膜增强的多层含氟交联掺杂离子膜及其制备方法 |
| CN102008905B (zh) * | 2010-06-18 | 2013-09-25 | 山东华夏神舟新材料有限公司 | 一种质子交换膜及其制备方法和应用 |
| WO2011156936A1 (zh) * | 2010-06-18 | 2011-12-22 | 山东东岳神舟新材料有限公司 | 一种质子交换膜及其制备方法和应用 |
| WO2012082703A2 (en) | 2010-12-17 | 2012-06-21 | 3M Innovative Properties Company | Preparation of oligomers and co-oligomers of highly fluorinated sulfinic acids and salts thereof |
| CN103370345B (zh) | 2010-12-17 | 2016-06-29 | 3M创新有限公司 | 高度氟化的亚磺酸的低聚物和共低聚物及其盐 |
| JP5837610B2 (ja) | 2010-12-17 | 2015-12-24 | スリーエム イノベイティブ プロパティズ カンパニー | 部分的にフッ素化されたポリスルフィン酸及びその塩 |
| EP2651880B1 (en) | 2010-12-17 | 2017-10-04 | 3M Innovative Properties Company | Preparation of perfluorovinyl ether sulfinic acids and their salts |
| EP3611195A1 (en) | 2010-12-17 | 2020-02-19 | 3M Innovative Properties Co. | Partially fluorinated sulfinic acid monomers and their salts |
| CN103582627B (zh) | 2011-06-03 | 2016-08-31 | 3M创新有限公司 | 烯丙基醚封端的氟代烷基亚磺酸及其盐 |
| CN102633688A (zh) | 2012-04-13 | 2012-08-15 | 华东理工大学 | 全氟乙烯基醚磺酸盐及其制备方法和用途 |
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- 2011-12-16 WO PCT/US2011/065339 patent/WO2012083107A2/en not_active Ceased
- 2011-12-16 JP JP2013544803A patent/JP5866375B2/ja active Active
- 2011-12-16 EP EP11848655.4A patent/EP2651990B1/en active Active
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014504293A (ja) * | 2010-12-17 | 2014-02-20 | スリーエム イノベイティブ プロパティズ カンパニー | 高度フッ素化スルフィン酸のオリゴマー及びコオリゴマー並びにその塩類 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013545880A (ja) | 2013-12-26 |
| WO2012083107A3 (en) | 2012-08-02 |
| EP2651990A4 (en) | 2015-08-12 |
| WO2012083107A2 (en) | 2012-06-21 |
| CN103261242B (zh) | 2016-05-04 |
| EP2651990B1 (en) | 2018-08-15 |
| US10093761B2 (en) | 2018-10-09 |
| EP2651990A2 (en) | 2013-10-23 |
| CN103261242A (zh) | 2013-08-21 |
| US20130251930A1 (en) | 2013-09-26 |
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