JP2015500377A - 耐低温フッ素含有エラストマー及びその製造方法 - Google Patents
耐低温フッ素含有エラストマー及びその製造方法 Download PDFInfo
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- JP2015500377A JP2015500377A JP2014546289A JP2014546289A JP2015500377A JP 2015500377 A JP2015500377 A JP 2015500377A JP 2014546289 A JP2014546289 A JP 2014546289A JP 2014546289 A JP2014546289 A JP 2014546289A JP 2015500377 A JP2015500377 A JP 2015500377A
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- containing elastomer
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- 229920001971 elastomer Polymers 0.000 title claims abstract description 54
- 239000000806 elastomer Substances 0.000 title claims abstract description 50
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 44
- 239000011737 fluorine Substances 0.000 title claims abstract description 44
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 239000000178 monomer Substances 0.000 claims abstract description 72
- -1 perfluoro Chemical group 0.000 claims abstract description 53
- 239000000203 mixture Substances 0.000 claims abstract description 40
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims abstract description 28
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006116 polymerization reaction Methods 0.000 claims description 45
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 29
- 239000000839 emulsion Substances 0.000 claims description 17
- 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 15
- 239000003999 initiator Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000003995 emulsifying agent Substances 0.000 claims description 11
- 239000012736 aqueous medium Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 239000012986 chain transfer agent Substances 0.000 claims description 7
- JILAKKYYZPDQBE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoro-1,4-diiodobutane Chemical compound FC(F)(I)C(F)(F)C(F)(F)C(F)(F)I JILAKKYYZPDQBE-UHFFFAOYSA-N 0.000 claims description 6
- OVJCTKGXZMKBCX-UHFFFAOYSA-N 1-bromo-3,3,4,4-tetrafluorobut-1-ene Chemical compound FC(F)C(F)(F)C=CBr OVJCTKGXZMKBCX-UHFFFAOYSA-N 0.000 claims description 6
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical group ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 claims description 3
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 3
- PGRFXXCKHGIFSV-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-iodobutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)I PGRFXXCKHGIFSV-UHFFFAOYSA-N 0.000 claims description 2
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims description 2
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 claims description 2
- GQCQMFYIFUDARF-UHFFFAOYSA-N 4-bromo-1,1,2-trifluorobut-1-ene Chemical compound FC(F)=C(F)CCBr GQCQMFYIFUDARF-UHFFFAOYSA-N 0.000 claims description 2
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 claims description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 2
- ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical compound OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 claims description 2
- LWHQXUODFPPQTL-UHFFFAOYSA-M sodium;2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate Chemical compound [Na+].[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 LWHQXUODFPPQTL-UHFFFAOYSA-M 0.000 claims description 2
- 238000004073 vulcanization Methods 0.000 claims description 2
- MLRCQIICAYVJHD-UHFFFAOYSA-N 1-but-1-enoxybut-1-ene Chemical compound CCC=COC=CCC MLRCQIICAYVJHD-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 7
- 230000008859 change Effects 0.000 abstract description 4
- 238000002474 experimental method Methods 0.000 abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 2
- 230000000379 polymerizing effect Effects 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- 229920001774 Perfluoroether Polymers 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 208000028659 discharge Diseases 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005987 sulfurization reaction Methods 0.000 description 3
- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 229920001973 fluoroelastomer Polymers 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZPYGRBTUNITHKJ-UHFFFAOYSA-N 1-bromo-1,1,2,2-tetrafluoro-2-(1,2,2-trifluoroethenoxy)ethane Chemical group FC(F)=C(F)OC(F)(F)C(F)(F)Br ZPYGRBTUNITHKJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BQTLXRPGQQLNBW-UHFFFAOYSA-N C(C(C(C(Br)Br)(F)F)(F)F)(F)Br Chemical compound C(C(C(C(Br)Br)(F)F)(F)F)(F)Br BQTLXRPGQQLNBW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 150000002978 peroxides Chemical group 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000005486 sulfidation 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
- 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
- C08F214/22—Vinylidene fluoride
- C08F214/222—Vinylidene fluoride with fluorinated vinyl ethers
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F214/184—Monomers containing fluorine with fluorinated vinyl ethers
-
- 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
- C08F214/22—Vinylidene fluoride
-
- 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
-
- 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
- C08F216/00—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/14—Monomers containing only one unsaturated aliphatic radical
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- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/14—Treatment of polymer emulsions
- C08F6/22—Coagulation
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- 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
- C08F216/00—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/14—Monomers containing only one unsaturated aliphatic radical
- C08F216/1408—Monomers containing halogen
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- 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
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/21—Rubbery or elastomeric properties
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- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
1,1−ジフルオロエチレンが50〜75mol%であり、テトラフルオロエチレンが2〜5mol%であり、パーフルオロ(アルキルビニルエーテル)が15〜30mol%であり、加硫モノマーが2〜6mol%である。
水媒体と乳化剤を混合し、水媒体における乳化剤の濃度として、水媒体100重量部に対し、乳化剤を0.01〜5重量部配合し、pH値を7〜12に調整するステップ1と、
1,1−ジフルオロエチレン、テトラフルオロエチレン、パーフルオロ(アルキルビニルエーテル)と加硫モノマーの単量体混合物を添加し、配合比に従い乳液を形成し、水媒体100重量部に対し、単量体混合物を30〜150重量部配合するステップ2と、
開始剤を入れ、0〜110℃、1〜5MPaで重合反応を行い、重合反応が行われる間に、連鎖移動剤を入れ、且つ反応を恒圧に維持するステップ3と、
最後に、重合後の乳液を凝集させ、洗浄、乾燥してなるステップ4と、
を含む。
単量体混合物のタンクに、1,1−ジフルオロエチレン(VDF)65mol%、テトラフルオロエチレン(TFE)3mol%、パーフルオロ(メチルビニルエーテル)(PMVE)29.5mol%とCF2=CFOCF2CF2CF2OCF2Br 2.5mol%からなる単量体混合物を準備・配置した。
実施例1のように、単量体混合物タンクに、1,1−ジフルオロエチレン(VDF)65mol%、テトラフルオロエチレン(TFE)5mol%、パーフルオロ(メチルビニルエーテル)(PMVE)27.5mol%とCF2=CFOCF2CF2CF2OCF2Br 2.5mol%からなる単量体混合物を準備・配置した。
実施例1のように、単量体混合物タンクに、1,1−ジフルオロエチレン(VDF)70mol%、テトラフルオロエチレン(TFE)5mol%、パーフルオロ(メチルビニルエーテル)(PMVE)22.5mol%とCF2=CFOCF2CF2CF2OCF2Br 2.5mol%からなる単量体混合物を準備・配置した。実施例1と同様に、重合及び凝集、洗浄を行い、重合体1.9Kgを得て、その性能指標を表2に示した。
単量体混合物タンクに、1,1−ジフルオロエチレン(VDF)70mol%、テトラフルオロエチレン(TFE)5mol%、パーフルオロ(メチルビニルエーテル)(PMVE)21mol%とCF2=CFOCF2CF2CF2OCF2Br 4mol%からなる単量体混合物を準備・配置した。
実施例4を基礎として、マロン酸ジエチルを1,4−ジヨードパーフルオロ−ブタンに変え、その使用量を6gとし、単量体の配合比及びプロセスは実施例2と同じであった。その性能特性指標を表3に示した。
実施例5を基礎として、凝集剤を硫酸アルミニウムカリウムに変え、単量体の配合比及びプロセスは実施例5と同じであった。その性能特性指標を表3に示した。
単量体混合物タンクに、1,1−ジフルオロエチレン(VDF)50mol%、テトラフルオロエチレン(TFE)10mol%、パーフルオロ(n−プロピルビニルエーテル)30mol%と3−ブロモパーフルオロ(プロピルビニル)エーテル10mol%からなる単量体混合物を準備・配置した。
実施例7と同様にして、重合圧力を3.0MPaまでに上げ、重合時間を2.5hとした。
Claims (10)
- 下記のコモノマー、即ち40〜80mol%の1,1−ジフルオロエチレン、2〜10mol%のテトラフルオロエチレン、10〜30mol%のパーフルオロ(アルキルビニルエーテル)、および1〜10mol%の加硫モノマーを重合してなり、前記加硫モノマーは、ハロゲン化トリフルオロエチレン、臭化アルキルビニルエーテル、塩素化イソブチレン、CF2=CFOCF2CF2CF2OCF2Br、1−ブロモ−2,2−ジフルオロエチレン、臭化トリフルオロエチレン、4−ブロモ−1,1,2−トリフルオロブテン−1、2−ブロモパーフルオロ(エチルビニル)エーテル、3−ブロモパーフルオロ(プロピルビニル)エーテルまたは1−ブロモ−3,3,4,4−テトラフルオロブテンを含む、ことを特徴とする耐低温フッ素含有エラストマー。
- 前記コモノマーの含有量は、1,1−ジフルオロエチレンが50〜75mol%であり、テトラフルオロエチレンが2〜5mol%であり、パーフルオロ(アルキルビニルエーテル)が15〜30mol%であり、加硫モノマーが2〜6mol%である、ことを特徴とする請求項1に記載の耐低温フッ素含有エラストマー。
- 前記加硫モノマーは、CF2=CFOCF2CF2CF2OCF2Br、1−ブロモ−2,2−ジフルオロエチレン、臭化トリフルオロエチレン、4−ブロモ−1,1,2−トリフルオロブテン−1、2−ブロモパーフルオロ(エチルビニル)エーテル、3−ブロモパーフルオロ(プロピルビニル)エーテルまたは1−ブロモ−3,3,4,4−テトラフルオロブテンであり、最も好ましくは、CF2=CFOCF2CF2CF2OCF2Br、3−ブロモパーフルオロ(プロピルビニル)エーテルまたは1−ブロモ−3,3,4,4−テトラフルオロブテンである、ことを特徴とする請求項1または2に記載の耐低温フッ素含有エラストマー。
- 前記パーフルオロ(アルキルビニルエーテル)がパーフルオロ(メチルビニルエーテル)またはパーフルオロ(n−プロピルビニルエーテル)である、ことを特徴とする請求項1乃至3の何れか一項に記載の耐低温フッ素含有エラストマー。
- 水媒体と乳化剤を混合し、水媒体における乳化剤の濃度として、水媒体100重量部に対し、乳化剤0.01〜5重量部を添加し、pH値を7〜12に調整するステップ1と、
1,1−ジフルオロエチレン、テトラフルオロエチレン、パーフルオロ(アルキルビニルエーテル)と加硫モノマーの単量体混合物を添加し、配合比に従って乳液を形成し、水媒体100重量部に対し、単量体混合物30〜150重量部を添加するステップ2と、
開始剤を入れ、0〜110℃、1〜5MPaで重合反応を行い、重合反応が行われる間に、連鎖移動剤を入れ、反応の恒圧を維持するステップ3と、
最後に、重合後の乳液を凝集させ、洗浄、乾燥してなるステップ4と、
を含むこと、を特徴とする請求項1乃至4の何れか一項に記載の耐低温フッ素含有エラストマーの製造方法。 - ステップ1における前記乳化剤は長鎖パーフルオロカルボン酸塩であり、好ましくはパーフルオロオクタン酸アンモニウム、パーフルオロオクタン酸ナトリウムまたはパーフルオロノナン酸アンモニウムである、ことを特徴とする請求項5に記載の方法。
- 前記開始剤は過硫酸アンモニウム、過硫酸カリウムまたは過硫酸ナトリウムであり、開始剤の量は単量体混合物の重量の0.001〜5%である、ことを特徴とする請求項5または6に記載の方法。
- 前記重合反応の温度は40〜100℃である、ことを特徴とする請求項5乃至7の何れか一項に記載の方法。
- 前記連鎖移動剤は、四塩化炭素、ヘキサン、アセトン、マロン酸ジエチル、コハク酸ジエチルまたは酢酸エチル、ヨウ化メチレン、ヨウ化パーフルオロブチル、1,4−ジヨードパーフルオロ−ブタンであり、前記連鎖移動剤の量は単量体混合物の重量の0.01〜5%である、ことを特徴とする請求項5乃至8の何れか一項に記載の方法。
- 恒圧を維持し、単量体混合物を追加することにより、反応圧力を1.2〜4MPaに制御する、ことを特徴とする請求項5乃至9の何れか一項に記載の方法。
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