JP2538267C - - Google Patents
Info
- Publication number
- JP2538267C JP2538267C JP2538267C JP 2538267 C JP2538267 C JP 2538267C JP 2538267 C JP2538267 C JP 2538267C
- Authority
- JP
- Japan
- Prior art keywords
- mol
- copolymer
- fluorine
- elastic copolymer
- fluorinated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920001577 copolymer Polymers 0.000 claims description 47
- -1 perfluoro Chemical group 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 6
- 229920001774 Perfluoroether Polymers 0.000 claims description 5
- BFKJFAAPBSQJPD-UHFFFAOYSA-N Tetrafluoroethylene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000010556 emulsion polymerization method Methods 0.000 claims description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 239000007870 radical polymerization initiator Substances 0.000 claims 4
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims 2
- 238000006116 polymerization reaction Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000007334 copolymerization reaction Methods 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 238000004073 vulcanization Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 238000010060 peroxide vulcanization Methods 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N Ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- SNGREZUHAYWORS-UHFFFAOYSA-N Perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 229940001607 sodium bisulfite Drugs 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-Trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- KARUMYWDGQTPFL-UHFFFAOYSA-N 1,3-dibromo-5-iodobenzene Chemical compound BrC1=CC(Br)=CC(I)=C1 KARUMYWDGQTPFL-UHFFFAOYSA-N 0.000 description 1
- FPYMBRJPVPWOOF-UHFFFAOYSA-N 1-bromo-1,1,2,2,3,3,4,4-octafluoro-4-iodobutane Chemical compound FC(F)(Br)C(F)(F)C(F)(F)C(F)(F)I FPYMBRJPVPWOOF-UHFFFAOYSA-N 0.000 description 1
- WHFBTQVXURKRCS-UHFFFAOYSA-N 1-bromo-1,1,2,2,3,3-hexafluoro-3-iodopropane Chemical compound FC(F)(Br)C(F)(F)C(F)(F)I WHFBTQVXURKRCS-UHFFFAOYSA-N 0.000 description 1
- ZYNPYKGTNSXKPI-UHFFFAOYSA-N 1-bromo-1,1,2,2-tetrafluoro-2-iodoethane Chemical compound FC(F)(Br)C(F)(F)I ZYNPYKGTNSXKPI-UHFFFAOYSA-N 0.000 description 1
- WIKWRDOTWLACTF-UHFFFAOYSA-N 1-bromo-3,5-diiodobenzene Chemical compound BrC1=CC(I)=CC(I)=C1 WIKWRDOTWLACTF-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N 2,2,2-trifluoroethyl alcohol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-tris(prop-2-enoxy)-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N Chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N Cyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- QQOJBGSLTQMSRF-UHFFFAOYSA-N FC(F)(F)C(F)(Cl)C(F)(F)C(F)(Cl)C(F)(C(Cl)=O)OOC(F)(C(Cl)=O)C(F)(Cl)C(F)(F)C(F)(Cl)C(F)(F)F Chemical compound FC(F)(F)C(F)(Cl)C(F)(F)C(F)(Cl)C(F)(C(Cl)=O)OOC(F)(C(Cl)=O)C(F)(Cl)C(F)(F)C(F)(Cl)C(F)(F)F QQOJBGSLTQMSRF-UHFFFAOYSA-N 0.000 description 1
- WMIYKQLTONQJES-UHFFFAOYSA-N Hexafluoroethane Chemical compound FC(F)(F)C(F)(F)F WMIYKQLTONQJES-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 231100000078 corrosive Toxicity 0.000 description 1
- 231100001010 corrosive Toxicity 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 230000003247 decreasing Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000002828 fuel tank Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Family
ID=
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2538267B2 (ja) | 含フッ素弾性状共重合体の製造法 | |
EP0425259B1 (en) | Peroxide-curable fluoroelastomers and chlorofluoroelastomers having bromine and iodine curesites and the preparation thereof | |
KR100408340B1 (ko) | 불소함유탄성상공중합체,이것을함유하는경화용조성물및이로부터제조한밀봉재 | |
EP0398241B1 (en) | Peroxide curable fluoroelastomers having bromine and iodine curesites and the preparation thereof | |
CA2209324C (en) | Vdf polymerization process | |
JP3320066B2 (ja) | 架橋された弗素系エラストマー組成物 | |
EP1833860B1 (en) | Fluoroelastomers having low glass transition temperature | |
CA2150343A1 (en) | Curable fluoroelastomeric compositions | |
EP0979832B1 (en) | Fluoroelastomers | |
EP0472653A1 (en) | PREPARATION OF CYANO PERFLUOROPOLYMERS CONTAINING IODIC HARDENING SITES. | |
JPH05500070A (ja) | ヨウ素硬化部位を有するシアノ含有パーフルオロポリマー類 | |
BR9907309B1 (pt) | composição curável de fluorelastÈmeros, seu uso, e, processo para a obtenção de uma composição curável de fluorelastÈmeros. | |
IE921535A1 (en) | Fluoroelastomers based on vinylidene fluoride exhibiting¹superior resistant to organic bases | |
BR0204232B1 (pt) | perfluoroelastâmeros, misturas, e, artigos manufaturados. | |
JP3022614B2 (ja) | 塩基に対する安定性が改善された熱可塑性弗素弾性体 | |
EP0838482B1 (en) | O-rings from ionically curable fluoroelastomers | |
US5077359A (en) | Peroxide-curable fluoroelastomers and chlorofluoroelastomers having bromine and iodine curesites and the preparation | |
US6743874B2 (en) | Rapidly crosslinking fluoropolymer | |
JP2711906B2 (ja) | 含フッ素弾性状共重合体 | |
CA2096673C (en) | Fluoroelastomeric and fluoroplastomeric copolymers having a high resistance to bases | |
JP2538267C (it) | ||
JP3864133B2 (ja) | 含フッ素共重合体の製造方法並びに該方法で得られた成形用含フッ素共重合体 | |
EP0865452B1 (en) | Base resistant fluorinated polymers | |
WO2021038384A1 (en) | Curable fluoropolymer compositions comprising a compound containing a phthalonitrile and an olefinic bond and cured articles therefrom |