TWI672321B - 高氟化彈性體 - Google Patents
高氟化彈性體 Download PDFInfo
- Publication number
- TWI672321B TWI672321B TW104107068A TW104107068A TWI672321B TW I672321 B TWI672321 B TW I672321B TW 104107068 A TW104107068 A TW 104107068A TW 104107068 A TW104107068 A TW 104107068A TW I672321 B TWI672321 B TW I672321B
- Authority
- TW
- Taiwan
- Prior art keywords
- fluorinated
- ether
- carbons
- perfluoro
- composition
- Prior art date
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- 229920001971 elastomer Polymers 0.000 title claims abstract description 48
- 239000000806 elastomer Substances 0.000 title claims abstract description 45
- 239000000178 monomer Substances 0.000 claims abstract description 88
- -1 fluorinated diiodoether compound Chemical class 0.000 claims abstract description 68
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 53
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims description 73
- 229920002313 fluoropolymer Polymers 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 44
- 238000006116 polymerization reaction Methods 0.000 claims description 42
- 150000002978 peroxides Chemical class 0.000 claims description 31
- 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 25
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 21
- 229920001973 fluoroelastomer Polymers 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000002825 nitriles Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000005215 alkyl ethers Chemical class 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000005394 methallyl group Chemical group 0.000 claims description 3
- FOKCKXCUQFKNLD-UHFFFAOYSA-N pent-1-enyl hypofluorite Chemical compound C(CC)C=COF FOKCKXCUQFKNLD-UHFFFAOYSA-N 0.000 claims description 3
- WFJINAXLTGKWLB-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2,3,3-hexafluoro-3-(trifluoromethoxy)propane Chemical compound FC(F)(F)OC(F)(F)C(F)(F)C(F)(F)OC=C WFJINAXLTGKWLB-UHFFFAOYSA-N 0.000 claims description 2
- ZLFSOCVJMGQPTE-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethane Chemical compound FC(F)(F)OC(F)(F)C(F)(F)OC=C ZLFSOCVJMGQPTE-UHFFFAOYSA-N 0.000 claims description 2
- YKWORVRLPTZONH-UHFFFAOYSA-N 1-ethenoxy-1,1,2,3,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propane Chemical compound FC(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC=C YKWORVRLPTZONH-UHFFFAOYSA-N 0.000 claims description 2
- FGEGZNORXGGFML-UHFFFAOYSA-N C(C)C=COF Chemical compound C(C)C=COF FGEGZNORXGGFML-UHFFFAOYSA-N 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical class C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims 2
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000003682 fluorination reaction Methods 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 description 68
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 49
- 239000011630 iodine Substances 0.000 description 42
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 36
- 239000004811 fluoropolymer Substances 0.000 description 34
- 239000002253 acid Substances 0.000 description 25
- 239000003995 emulsifying agent Substances 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
- 239000003292 glue Substances 0.000 description 14
- 238000002835 absorbance Methods 0.000 description 13
- 239000000370 acceptor Substances 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 12
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 11
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 11
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 11
- 229910021641 deionized water Inorganic materials 0.000 description 11
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 238000012546 transfer Methods 0.000 description 10
- XSWGGBJIPSPTBZ-UHFFFAOYSA-N FC(=C(C(C(C(OC(C(I)(F)F)(F)F)(F)F)(F)F)(F)F)F)OC(=C(F)C(C(C(OC(C(F)(F)I)(F)F)(F)F)(F)F)(F)F)F Chemical compound FC(=C(C(C(C(OC(C(I)(F)F)(F)F)(F)F)(F)F)(F)F)F)OC(=C(F)C(C(C(OC(C(F)(F)I)(F)F)(F)F)(F)F)(F)F)F XSWGGBJIPSPTBZ-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 238000004132 cross linking Methods 0.000 description 9
- 239000012986 chain transfer agent Substances 0.000 description 8
- 230000009477 glass transition Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 230000006835 compression Effects 0.000 description 6
- 238000007906 compression Methods 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 239000004816 latex Substances 0.000 description 5
- 229920000126 latex Polymers 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000011787 zinc oxide Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- 238000004945 emulsification Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 3
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- 229920006169 Perfluoroelastomer Polymers 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
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- 239000005060 rubber Substances 0.000 description 3
- WUMVZXWBOFOYAW-UHFFFAOYSA-N 1,2,3,3,4,4,4-heptafluoro-1-(1,2,3,3,4,4,4-heptafluorobut-1-enoxy)but-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)F WUMVZXWBOFOYAW-UHFFFAOYSA-N 0.000 description 2
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 2
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical group CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical class CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
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- 239000004641 Diallyl-phthalate Substances 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 2
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- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 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
- 150000002496 iodine Chemical class 0.000 description 2
- VSHDHKDWBUMJIJ-UHFFFAOYSA-N iodo hypoiodite Chemical class IOI VSHDHKDWBUMJIJ-UHFFFAOYSA-N 0.000 description 2
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- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
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- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
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- JPQBRSQJGWOTGC-UHFFFAOYSA-N methyl(silyloxysilyloxy)silane Chemical compound C[SiH2]O[SiH2]O[SiH3] JPQBRSQJGWOTGC-UHFFFAOYSA-N 0.000 description 1
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- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical class 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
- 229920005548 perfluoropolymer Polymers 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
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- 229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
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- 229920000570 polyether Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- SGRFJCYSONFVST-UHFFFAOYSA-N prop-2-enyl cyanate Chemical compound C=CCOC#N SGRFJCYSONFVST-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- 238000007655 standard test method Methods 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
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- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
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Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
- C08L15/02—Rubber derivatives containing halogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens 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
-
- 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
- C08F214/26—Tetrafluoroethene
- C08F214/262—Tetrafluoroethene with fluorinated vinyl ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
- C08L23/28—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with halogens or halogen-containing compounds
-
- 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
- C08F214/16—Monomers containing bromine or iodine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
Landscapes
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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| US9982091B2 (en) | 2014-03-06 | 2018-05-29 | 3M Innovative Properties Company | Highly fluorinated elastomers |
| WO2016089617A1 (en) | 2014-12-01 | 2016-06-09 | 3M Innovative Properties Company | Methods of making halogenated fluorinated ether-containing compounds |
| JP6908604B2 (ja) * | 2015-10-23 | 2021-07-28 | スリーエム イノベイティブ プロパティズ カンパニー | 非晶質フルオロポリマーとフルオロプラスチック粒子とを含む組成物及びその製造方法 |
| KR20190077405A (ko) * | 2016-11-09 | 2019-07-03 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 퍼옥사이드 경화성 부분 플루오르화 중합체 |
| EP3333229A1 (en) * | 2016-12-08 | 2018-06-13 | 3M Innovative Properties Company | Fluoropolymer compositions and coatings |
| WO2018136332A1 (en) | 2017-01-18 | 2018-07-26 | 3M Innovative Properties Company | Fluorinated block copolymers derived from cure-site monomers |
| EP3571235A4 (en) | 2017-01-18 | 2020-11-11 | 3M Innovative Properties Company | FLUORINATED BLOCK COPOLYMERS MADE FROM NITRILE CURE SITE MONOMERS |
| US11261280B2 (en) | 2017-01-18 | 2022-03-01 | 3M Innovative Properties Company | Fluorinated block copolymers |
| 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 |
| RU2020121824A (ru) * | 2017-12-06 | 2022-01-10 | ЭйДжиСи Инк. | Фторированный эластичный сополимер и способ получения фторированного эластичного сополимера |
| CN112262172B (zh) | 2018-06-12 | 2023-08-01 | 3M创新有限公司 | 包含胺固化剂的含氟聚合物涂料组合物、经涂覆的基底以及相关方法 |
| WO2019239320A1 (en) | 2018-06-12 | 2019-12-19 | 3M Innovative Properties Company | Fluoropolymer compositions comprising fluorinated additives, coated substrates and methods |
| US20210324137A1 (en) | 2018-08-27 | 2021-10-21 | 3M Innovative Properties Company | Peroxide curable highly fluorinated polymers comprising an internal fluorinated plasticizer and articles therefrom |
| CN113166472B (zh) * | 2018-12-14 | 2023-03-28 | 3M创新有限公司 | 包含含双邻苯二甲腈的化合物的可固化含氟聚合物组合物及其固化制品 |
| EP3950323A4 (en) * | 2019-04-04 | 2022-12-28 | Agc Inc. | LAMINATE MANUFACTURING PROCESS AND LAMINATE |
| US12509569B2 (en) * | 2019-08-27 | 2025-12-30 | 3M Innovative Properties Company | Curable fluoropolymer compositions comprising metal fluoride particles and articles therefrom |
| US12291588B2 (en) | 2019-11-04 | 2025-05-06 | 3M Innovative Properties Company | Fluoropolymer compositions comprising a curing agent with ethylenically unsaturated and electron donor groups, and substrates coated therewith |
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| WO2021094884A1 (en) | 2019-11-13 | 2021-05-20 | 3M Innovative Properties Company | A method of functionalizing fluorinated polymers, a functionalized fluorinated polymer and coating compositions thereof |
| US20230026338A1 (en) * | 2019-12-30 | 2023-01-26 | 3M Innovative Properties Company | Composition Including Fluoropolymer, Benzoyl Peroxide, and Crosslinker and Related Articles and Methods |
| US20240186031A1 (en) | 2021-05-05 | 2024-06-06 | 3M Innovative Properties Company | Fluoropolymer compositions comprising amorphous fluoropolymer and crystalline fluoropolymer suitable for copper and electronic telecommunications articles |
| WO2022234363A1 (en) | 2021-05-05 | 2022-11-10 | 3M Innovative Properties Company | Fluoropolmyer compositions comprising uncrosslinked fluoropolymer suitable for copper and electronic telecommunications articles |
| US20240194371A1 (en) | 2021-05-05 | 2024-06-13 | 3M Innovative Properties Company | Fluoropolymer compositions comprising fluoropolymer with polymerized unsaturated fluorinated alkyl ether suitable for copper and electronic telecommunications articles |
| WO2023042005A1 (en) | 2021-09-16 | 2023-03-23 | 3M Innovative Properties Company | Core shell fluoropolmyers with functional groups suitable for copper and electronic telecommunications articles |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3900380A (en) * | 1972-03-02 | 1975-08-19 | Dow Chemical Co | Preparation of fluorinated cyclobutenyl alkyl ether copolymers |
| US6160051A (en) * | 1998-06-11 | 2000-12-12 | Nippon Mektron, Limited | Process for producing fluorine-containing block copolymer |
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- 2015-03-03 US US15/122,538 patent/US9982091B2/en active Active
- 2015-03-03 EP EP15757905.3A patent/EP3114167B1/en active Active
- 2015-03-03 JP JP2016555780A patent/JP6773560B2/ja active Active
- 2015-03-03 KR KR1020167024479A patent/KR102279977B1/ko active Active
- 2015-03-03 EP EP20166339.0A patent/EP3696224A1/en active Pending
- 2015-03-03 CN CN201580012313.1A patent/CN106103572B/zh not_active Expired - Fee Related
- 2015-03-03 WO PCT/US2015/018402 patent/WO2015134435A1/en not_active Ceased
- 2015-03-05 TW TW104107068A patent/TWI672321B/zh active
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Also Published As
| Publication number | Publication date |
|---|---|
| EP3114167A4 (en) | 2018-02-14 |
| TW201540731A (zh) | 2015-11-01 |
| KR102279977B1 (ko) | 2021-07-22 |
| KR20160130238A (ko) | 2016-11-10 |
| CN106103572B (zh) | 2019-09-27 |
| CN106103572A (zh) | 2016-11-09 |
| JP6773560B2 (ja) | 2020-10-21 |
| EP3114167A1 (en) | 2017-01-11 |
| EP3114167B1 (en) | 2020-05-27 |
| US9982091B2 (en) | 2018-05-29 |
| EP3696224A1 (en) | 2020-08-19 |
| US20170066877A1 (en) | 2017-03-09 |
| JP2017507223A (ja) | 2017-03-16 |
| WO2015134435A1 (en) | 2015-09-11 |
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