JP2002514181A - リンを含有するフルオロモノマーおよびそれらのポリマー - Google Patents
リンを含有するフルオロモノマーおよびそれらのポリマーInfo
- Publication number
- JP2002514181A JP2002514181A JP51384998A JP51384998A JP2002514181A JP 2002514181 A JP2002514181 A JP 2002514181A JP 51384998 A JP51384998 A JP 51384998A JP 51384998 A JP51384998 A JP 51384998A JP 2002514181 A JP2002514181 A JP 2002514181A
- Authority
- JP
- Japan
- Prior art keywords
- fluoropolymer
- compound
- polymer
- tfe
- weight
- 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.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims description 75
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract description 35
- 229910052698 phosphorus Inorganic materials 0.000 title abstract description 34
- 239000011574 phosphorus Substances 0.000 title abstract description 34
- 229920002313 fluoropolymer Polymers 0.000 claims abstract description 74
- 239000004811 fluoropolymer Substances 0.000 claims abstract description 73
- 239000000178 monomer Substances 0.000 claims abstract description 43
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000576 coating method Methods 0.000 claims description 64
- 239000011248 coating agent Substances 0.000 claims description 56
- 239000000203 mixture Substances 0.000 claims description 50
- 239000006185 dispersion Substances 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- -1 NH 4 Inorganic materials 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 229920002379 silicone rubber Polymers 0.000 claims description 13
- 239000004945 silicone rubber Substances 0.000 claims description 13
- 229920001971 elastomer Polymers 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 239000000806 elastomer Substances 0.000 claims description 5
- 229920001774 Perfluoroether Polymers 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 37
- 229920001577 copolymer Polymers 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000000843 powder Substances 0.000 description 23
- 239000007787 solid Substances 0.000 description 16
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 238000000113 differential scanning calorimetry Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- 239000005060 rubber Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000004293 19F NMR spectroscopy Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229920006125 amorphous polymer Polymers 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000000608 laser ablation Methods 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- BNMZREDQMDQOQV-UHFFFAOYSA-N 1-ethenoxy-2-propoxypropane Chemical compound CCCOC(C)COC=C BNMZREDQMDQOQV-UHFFFAOYSA-N 0.000 description 2
- YSYRISKCBOPJRG-UHFFFAOYSA-N 4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=C(F)OC(C(F)(F)F)(C(F)(F)F)O1 YSYRISKCBOPJRG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- YOALFLHFSFEMLP-UHFFFAOYSA-N azane;2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoic acid Chemical compound [NH4+].[O-]C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YOALFLHFSFEMLP-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000004446 fluoropolymer coating Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 229920005548 perfluoropolymer Polymers 0.000 description 2
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 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 description 1
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical class C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GVEUEBXMTMZVSD-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,6-nonafluorohex-1-ene Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C GVEUEBXMTMZVSD-UHFFFAOYSA-N 0.000 description 1
- SBUOHGKIOVRDKY-UHFFFAOYSA-N 4-methyl-1,3-dioxolane Chemical compound CC1COCO1 SBUOHGKIOVRDKY-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000467686 Eschscholzia lobbii Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920002449 FKM Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 240000000220 Panda oleosa Species 0.000 description 1
- 235000016496 Panda oleosa Nutrition 0.000 description 1
- 229920006169 Perfluoroelastomer Polymers 0.000 description 1
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical group CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- ORBBVPFDROYXQS-UHFFFAOYSA-N ammonium perfluorononanoate Chemical compound N.OC(=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 ORBBVPFDROYXQS-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000004815 dispersion polymer Substances 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 238000004299 exfoliation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009415 formwork Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000006115 industrial coating Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- XIKYYQJBTPYKSG-UHFFFAOYSA-N nickel Chemical compound [Ni].[Ni] XIKYYQJBTPYKSG-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- QLFFCLRSMTUBEZ-UHFFFAOYSA-N phosphoric acid;sodium Chemical compound [Na].[Na].OP(O)(O)=O QLFFCLRSMTUBEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011819 refractory material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000000196 viscometry Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. 式CF2=CF-Rf-(CH2)n-OP(O)p-Φ2を有する化合物であって、nが1〜3で あり、pが0または1であり、Rfが1〜20炭素原子を有するパーフルオロアル キルまたはパーフルオロアルコキシであり、Φが臭素、塩素またはOMであり、お よびMがH、NH4、またはアルカリ金属であることを特徴とする化合物。 2. nが1であることを特徴とする請求項1に記載の化合物。 3. RfがO-(CF2)mであり、およびmが2〜4であることを特徴とする請求項2 に記載の化合物。 4. Rfが-[O-CF2CF(CF3)]k-O-CF2CF2-であり、およびkが1〜5であることを 特徴とする請求項2に記載の化合物。 5. kが1であることを特徴とする請求項4に記載の化合物。 6. 請求項1に記載の化合物から誘導されたユニットを含むことを特徴とする フルオロポリマー。 7. 少なくとも一つの別のフッ素化されたモノマーから誘導されたユニットを さらに含むことを特徴とする請求項6に記載のフルオロポリマー。 8. 前記別のフッ素化されたモノマーがフルオロオレフィンまたはフッ素化さ れたビニルエーテルであることを特徴とする請求項7に記載のフルオロポリマー 。 9. フッ素を含有しないモノマーから誘導されたユニットをさらに含むことを 特徴とする請求項7に記載のフルオロポリマー。 10. 前記請求項1に記載の化合物から誘導されたユニットが、全モノマーユ ニットを基準として0.02から10モル%で、前記フルオロポリマーに含まれ ることを特徴とする請求項7に記載のフルオロポリマー。 11. 水性分散液として存在することを特徴とする請求項6に記載のフルオロ ポリマー。 12. 被膜で被覆された支持体を含み、ここで前記被膜が請求項1に記載の化 合物から誘導されたユニットを有するフルオロポリマーを含むことを特徴とする 被覆された製品。 13. 前記支持体が金属であることを特徴とする請求項12に記載の被覆され た製品。 14. 前記支持体がポリマーであることを特徴とする請求項12に記載の被覆 された製品。 15. 前記ポリマーがエラストマーであることを特徴とする請求項14に記載 の被覆された製品。 16. 前記被膜が請求項1に記載の化合物から誘導されたユニットを持たない 別のフルオロポリマーを含有することを特徴とする請求項12に記載の被覆され た製品。 17. 前記別のフルオロポリマーの量が、前記請求項1に記載の化合物から誘 導されたユニットを含むフルオロポリマーの重量部に対して、20重量部までで あることを特徴とする請求項12に記載の被覆された製品。 18. 前記支持体が、シリコーンゴムの表面を有するコピア・ロールであるこ とを特徴とする請求項12に記載の被覆された製品。 19. 請求項1に記載の化合物から誘導されたユニットを含有するフルオロポ リマーと、請求項1に記載の化合物から誘導されたユニットを持たない別のフル オロポリマーとを含むことを特徴とするフルオロポリマーブレンド組成物。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US2602396P | 1996-09-13 | 1996-09-13 | |
US60/026,023 | 1997-09-09 | ||
US08/929,216 | 1997-09-09 | ||
US08/929,216 US5969067A (en) | 1996-09-13 | 1997-09-09 | Phosphorus-containing fluoromonomers and polymers thereof |
PCT/US1997/016070 WO1998011114A1 (en) | 1996-09-13 | 1997-09-11 | Phosphorus-containing fluoromonomers and polymers thereof |
Publications (3)
Publication Number | Publication Date |
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JP2002514181A true JP2002514181A (ja) | 2002-05-14 |
JP2002514181A5 JP2002514181A5 (ja) | 2005-01-13 |
JP3980650B2 JP3980650B2 (ja) | 2007-09-26 |
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Application Number | Title | Priority Date | Filing Date |
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JP51384998A Expired - Fee Related JP3980650B2 (ja) | 1996-09-13 | 1997-09-11 | リンを含有するフルオロモノマーおよびそれらのポリマー |
Country Status (6)
Country | Link |
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US (2) | US5969067A (ja) |
EP (1) | EP0927185B1 (ja) |
JP (1) | JP3980650B2 (ja) |
CN (2) | CN1101399C (ja) |
DE (1) | DE69738299T2 (ja) |
WO (1) | WO1998011114A1 (ja) |
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US4131740A (en) * | 1977-04-20 | 1978-12-26 | E. I. Du Pont De Nemours And Company | Alkyl perfluoro-ω-fluoroformyl esters and their preparation |
US4176215A (en) * | 1978-03-13 | 1979-11-27 | E. I. Du Pont De Nemours And Company | Ion-exchange structures of copolymer blends useful in electrolytic cells |
US4281092A (en) * | 1978-11-30 | 1981-07-28 | E. I. Du Pont De Nemours And Company | Vulcanizable fluorinated copolymers |
US4281091A (en) * | 1979-12-19 | 1981-07-28 | Monsanto Company | Unsaturated melamine condensates |
JPS6064940A (ja) * | 1983-09-21 | 1985-04-13 | Daikin Ind Ltd | 含フッ素オレフィン |
US5080287A (en) * | 1986-10-24 | 1992-01-14 | Nippondenso Co., Ltd. | Electromagnetic fuel injection valve for internal combustion engine |
US5081287A (en) * | 1989-06-30 | 1992-01-14 | Fmc Corporation | Pesticidal polyhalo alkenoic acid esters |
US5059720A (en) * | 1990-01-31 | 1991-10-22 | E. I. Du Pont De Nemours And Company | Hydroxy containing fluorovinyl compounds and polymers thereof |
US5328946A (en) * | 1991-08-29 | 1994-07-12 | E. I. Du Pont De Nemours And Company | Solvents for tetrafluoroethylene polymers |
DE69306402T2 (de) * | 1992-08-28 | 1997-04-30 | Du Pont | Niedrigschmelzendes tetrafluorethylene-copolymer und seine verwendung |
US5266639A (en) * | 1992-08-28 | 1993-11-30 | E. I. Du Pont De Nemours And Company | Low-melting tetrafluorethylene copolymer and its uses |
-
1997
- 1997-09-09 US US08/929,216 patent/US5969067A/en not_active Expired - Lifetime
- 1997-09-11 EP EP19970941030 patent/EP0927185B1/en not_active Expired - Lifetime
- 1997-09-11 JP JP51384998A patent/JP3980650B2/ja not_active Expired - Fee Related
- 1997-09-11 CN CN97197869A patent/CN1101399C/zh not_active Expired - Lifetime
- 1997-09-11 WO PCT/US1997/016070 patent/WO1998011114A1/en active IP Right Grant
- 1997-09-11 DE DE1997638299 patent/DE69738299T2/de not_active Expired - Lifetime
-
1999
- 1999-02-23 US US09/255,901 patent/US6177196B1/en not_active Expired - Lifetime
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- 2002-07-01 CN CNB021403430A patent/CN1255445C/zh not_active Expired - Lifetime
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JP2009502568A (ja) * | 2005-07-28 | 2009-01-29 | 三井・デュポンフロロケミカル株式会社 | フルオロポリマーフィルムによる積層物およびフィルム形成用フルオロポリマー |
KR101301321B1 (ko) * | 2005-07-28 | 2013-08-29 | 듀폰-미쯔이 플루오로케미칼 가부시끼가이샤 | 플루오로중합체 필름을 갖는 적층체 및 필름-형성플루오로중합체 |
JP2014208845A (ja) * | 2009-02-13 | 2014-11-06 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | パーフルオロエラストマー |
JP2009185301A (ja) * | 2009-05-19 | 2009-08-20 | Du Pont Mitsui Fluorochem Co Ltd | 被膜形成性フッ素樹脂組成物 |
US9785102B2 (en) | 2009-10-05 | 2017-10-10 | Canon Kabushiki Kaisha | Rotatable fixing member, manufacturing method thereof and fixing device |
JP2014534187A (ja) * | 2011-10-06 | 2014-12-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | フッ化アルコールの触媒的ホスホ−ハロゲン化方法 |
WO2022260137A1 (ja) * | 2021-06-11 | 2022-12-15 | ダイキン工業株式会社 | 含フッ素エラストマー水性分散液の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
US5969067A (en) | 1999-10-19 |
EP0927185A1 (en) | 1999-07-07 |
CN1230189A (zh) | 1999-09-29 |
CN1427014A (zh) | 2003-07-02 |
CN1101399C (zh) | 2003-02-12 |
DE69738299D1 (de) | 2007-12-27 |
JP3980650B2 (ja) | 2007-09-26 |
WO1998011114A1 (en) | 1998-03-19 |
EP0927185B1 (en) | 2007-11-14 |
US6177196B1 (en) | 2001-01-23 |
DE69738299T2 (de) | 2008-09-04 |
CN1255445C (zh) | 2006-05-10 |
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