JP2020504225A - ニトリル硬化部位モノマーから誘導されるフッ素化ブロックコポリマー - Google Patents
ニトリル硬化部位モノマーから誘導されるフッ素化ブロックコポリマー Download PDFInfo
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- JP2020504225A JP2020504225A JP2019558992A JP2019558992A JP2020504225A JP 2020504225 A JP2020504225 A JP 2020504225A JP 2019558992 A JP2019558992 A JP 2019558992A JP 2019558992 A JP2019558992 A JP 2019558992A JP 2020504225 A JP2020504225 A JP 2020504225A
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- 238000002844 melting Methods 0.000 claims description 12
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- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 2
- GEGZKCLDAZQIQZ-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12-tetracosafluoro-1,12-diiodododecane Chemical compound FC(F)(I)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I GEGZKCLDAZQIQZ-UHFFFAOYSA-N 0.000 description 2
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- ROHTVIURAJBDES-UHFFFAOYSA-N 2-n,2-n-bis(prop-2-enyl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N(CC=C)CC=C)=N1 ROHTVIURAJBDES-UHFFFAOYSA-N 0.000 description 1
- QMIWYOZFFSLIAK-UHFFFAOYSA-N 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene Chemical compound FC(F)(F)C(=C)C(F)(F)F QMIWYOZFFSLIAK-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical class C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- NFWPZNNZUCPLAX-UHFFFAOYSA-N 4-methoxy-3-methylaniline Chemical compound COC1=CC=C(N)C=C1C NFWPZNNZUCPLAX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 101001094880 Arabidopsis thaliana Pectinesterase 4 Proteins 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229910004762 CaSiO Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- SXWUSKUNDTYYNV-UHFFFAOYSA-N FC(=C(C(C(C(F)(F)F)(OC(C(C(F)(F)F)(F)F)(F)F)F)(F)F)F)OC(=C(F)C(C(C(F)(F)F)(F)OC(C(C(F)(F)F)(F)F)(F)F)(F)F)F Chemical compound FC(=C(C(C(C(F)(F)F)(OC(C(C(F)(F)F)(F)F)(F)F)F)(F)F)F)OC(=C(F)C(C(C(F)(F)F)(F)OC(C(C(F)(F)F)(F)F)(F)F)(F)F)F SXWUSKUNDTYYNV-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 101710113246 Pectinesterase 3 Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- 244000125380 Terminalia tomentosa Species 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 125000005192 alkyl ethylene group Chemical group 0.000 description 1
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012874 anionic emulsifier Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- FPODCVUTIPDRTE-UHFFFAOYSA-N bis(prop-2-enyl) hexanedioate Chemical compound C=CCOC(=O)CCCCC(=O)OCC=C FPODCVUTIPDRTE-UHFFFAOYSA-N 0.000 description 1
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical class C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 1
- 229920005605 branched copolymer Polymers 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000011231 conductive filler Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000007975 iminium salts Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- GHXZPUGJZVBLGC-UHFFFAOYSA-N iodoethene Chemical compound IC=C GHXZPUGJZVBLGC-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- UMKARVFXJJITLN-UHFFFAOYSA-N lead;phosphorous acid Chemical compound [Pb].OP(O)O UMKARVFXJJITLN-UHFFFAOYSA-N 0.000 description 1
- UHNWOJJPXCYKCG-UHFFFAOYSA-L magnesium oxalate Chemical compound [Mg+2].[O-]C(=O)C([O-])=O UHNWOJJPXCYKCG-UHFFFAOYSA-L 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ATPFMBHTMKBVLS-UHFFFAOYSA-N n-[6-(cinnamylideneamino)hexyl]-3-phenylprop-2-en-1-imine Chemical compound C=1C=CC=CC=1C=CC=NCCCCCCN=CC=CC1=CC=CC=C1 ATPFMBHTMKBVLS-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- MMCOUVMKNAHQOY-UHFFFAOYSA-L oxido carbonate Chemical compound [O-]OC([O-])=O MMCOUVMKNAHQOY-UHFFFAOYSA-L 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 229960004692 perflenapent Drugs 0.000 description 1
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 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
- 235000021317 phosphate Nutrition 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 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
- 238000010998 test method Methods 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- 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
- 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
- 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
- C08F214/28—Hexyfluoropropene
- C08F214/282—Hexyfluoropropene 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
- 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
- C08F216/1458—Monomers containing nitrogen
-
- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
Abstract
Description
(a) 少なくとも1つのAブロックであって、Aブロックは、少なくとも1つのフッ素化モノマーから誘導される繰り返しの二価モノマー単位を含む半結晶性セグメントである、Aブロックと、
(b) 少なくとも1つのBブロックであって、Bブロックは、少なくとも1つのフッ素化モノマー及びニトリル含有硬化部位モノマーから誘導される繰り返しの二価モノマー単位を含むセグメントである、Bブロックと、
を有するフッ素化ブロックコポリマーを含む硬化性組成物が提供される。
「a」、「an」、及び「the」という用語は、互換的に使用され、1以上を意味し、
「及び/又は」は、述べられた事例の一方又は両方が起こり得ることを示すために使用され、例えば、A及び/又はBは、(A及びB)と(A又はB)とを含み、
「主鎖」とは、ポリマーの主な連続鎖を指す。
「コポリマー」は、少なくとも2種の異なる共重合したモノマー(すなわち、同一の化学構造を有さないモノマー)を含むポリマー材料を指し、ターポリマー(3種の異なるモノマー)、テトラポリマー(4種の異なるモノマー)などを包含する。
「架橋」とは、予め形成した2つのポリマー鎖を、化学結合又は化学的な基を使用して連結することを指す。
「硬化部位」は、架橋に関与する場合がある、官能基を指す。
「ガラス転移温度」又は「Tg」は、ポリマー材料がガラス状態からゴム状態に転移する温度を指す。ガラス状態は、典型的には、例えば、脆く、剛直な、剛性の、又はこれらの組み合わせである材料に付随する。対照的に、ゴム状態は、典型的には、例えば、可撓性の材料及びエラストマー材料に付随する。
「共重合」とは、モノマーが一緒に重合してポリマー主鎖を形成することを指す。
「粉砕可能な」とは、ゴム用ミル及び内部ミキサ上で材料を加工できることである。
「モノマー」は、重合を経てその後ポリマーの基本的構造の部分を形成することができる分子である。
「ペルフルオロ化」とは、全ての水素原子がフッ素原子に置換されている、炭化水素から誘導される基又は化合物を意味する。ただし、ペルフルオロ化化合物は、塩素原子、臭素原子、及びヨウ素原子のような、フッ素原子及び炭素原子以外の原子を更に含有してもよい。
「ポリマー」とは、共重合したモノマーの単位を含む、マクロ構造を指す。
のものである。一実施形態では、R1、R2、R3、及びR4は互いに独立して、F、CF3、C2F5、C3F7、C4F9、H、CH3、C2H5、C3H7、又はC4H9である。一実施形態では、Zは、少なくとも1、2、3、4、又は更に5個の炭素原子を、そして最大で8、10、12、16、又は更に18個の炭素原子を含む。一実施形態では、Zは−O−Rf1−O−;−CF2−O−Rf1−O−CF2−;又はCF2−O−Rf1−O−[式中、Rf1は、直鎖又は分枝鎖ペルフルオロアルカンジイル、ペルフルオロオキサアルカンジイル、若しくはペルフルオロポリオキサアルカンジイル残基、又はRf2に従った残基から選択される残基を表す。]である。一実施形態では、Rf1は、少なくとも1、2、3、4、又は更に5個の炭素原子、及び最大で8、10、12、炭素原子14個の炭素原子を含有する。Rf2は非フッ素化、フッ素化、又はペルフルオロ化アリーレンである。アリーレンは非置換であってよい、又は、F以外の1つ以上のハロゲン原子、ペルフルオロ化アルキル残基、ペルフルオロ化アルコキシ残基、ペルフルオロ化オキサアルキル残基、ペルフルオロ化ポリオキサアルキル残基、フッ素化、ペルフルオロ化、若しくは非フッ素化フェニル若しくはフェノキシ部分、又はこれらの組み合わせで置換されていてよく、フェニル又はフェノキシ残基は非置換であってよい、又は、1つ以上のペルフルオロ化アルキル、アルコキシ、オキサアルキル、若しくはポリオキサアルキル残基、若しくはF以外の1つ以上のハロゲン原子、又はこれらの組み合わせで置換されていてよい。一実施形態では、Rf2は、少なくとも1、2、3、4、又は更に5個の炭素原子、及び最大で10、12、又は更に14個の炭素原子を含有する。
Rf−CF(I)−(CX2)n−(CX2CXR)m−O−R”f−Ok−(CXR’CX2)p−(CX2)q−CF(I)−R’f
[式中、
XはF、H、及びClから独立して選択され;
Rは、F、又は炭素を1〜3個含む部分的にフッ素化された若しくは全フッ素化されたアルカンであり、
Rf及びR’fは、独立して、F、及び1〜3個の炭素を有する一価のペルフルオロアルカンから選択され、
R”fは、1〜5個の炭素を有する二価のフルオロアルキレン、又は1〜8個の炭素及び少なくとも1個のエーテル連結を有する二価フッ素化アルキレンエーテルであり、
kは0又は1であり、n、m、q、及びpは0〜5の整数から独立して選択される(ただし、kが0である場合、n+mは少なくとも1であり、p+qは少なくとも1である)]。
例示的なフッ素化ジヨードエーテル化合物としては、I−CF2−CF2−O−CF2−CF2−I;I−CF2−CF2−O−(CF2)b−I[式中、bは3〜10の整数である。];
I−(CF2)c−O−(CF2)b−I[式中、cは3〜10の整数であり、bは3〜10の整数である。];ICF2−CF2−O−CF2−O−CF2−CF2−I;
ICF2−CF2−O−CF2−(CF2)b−O−CF2−CF2I[式中、bは1〜5の整数である。];
ICF2−CF2−[O−CF2−(CF2)b]z−O−CF2−CF2I[式中、bは1〜5の整数であり、zは1〜4の整数である。];
I−CF2−CH2−O−CF2−CF2−CF2I;I−CF2−CH2−CF2−O−CF2−CF2−CF2I;
I−CF2−CHF−CF2−O−CF2−CF2−CF2I;ICF2−CF2−O−CF2−CFI−CF3;
ICF2−CF2−(CF2)a−[O−CF−CF2]b−(O−[CF2]c)z−O[−CF2]d−CF2−CF2I[式中、aは0〜6の整数であり、bは0〜5の整数であり、cは1〜6の整数であり、dは0〜6の整数であり、zは0〜6の整数である。];
ICF2−(CF2)a−(O−CF2CF(CF3))b−O−(CF2)c−O−(CF2−CF−O)d−(CF2)z−O−CF2CF2−I[式中、aは0〜6の整数であり、bは0〜5の整数であり、cは1〜6の整数であり、dは0〜5の整数であり、zは0〜5の整数である。];及び、I−CF2−(CF2)a−O−(CF2)b−O−CF2−CF(CF3)−I[式中、aは1〜5の整数であり、bは1〜5の整数である。]
が挙げられる。このようなフッ素化ジヨードエーテル化合物は、国際公開第2015/134435(Hintzerら)に開示されており、参照により本明細書に組み込まれている。
Y−Rf−Z−M
[式中、Yは水素、Cl、又はFを表し、Rfは、4〜10個の炭素原子を有し、任意選択的にカテナリー酸素原子を含む、直鎖又は分枝鎖の部分フッ素化アルキレンを表し、ZはCOO−又はSO3 −を表し、Mは水素イオン、アルカリ金属イオン、又はアンモニウムイオンを表す。]。例示的なフッ素化乳化剤は、以下の一般式を有してよい:
[Rf−O−L−COO−]iXi+
[式中、Lは直鎖又は分枝鎖の部分フッ素化又は完全フッ素化アルキレン基又は脂肪族炭化水素基を表し、Rfは、直鎖又は分枝鎖の部分フッ素化又は完全フッ素化脂肪族基、又は1つ以上の酸素原子で中断されている、直鎖又は分枝鎖の部分フッ素化又は完全フッ素化基を表し、Xi+は、価数iを有するカチオンを表し、iは1、2、又は3である。]。一実施形態では、乳化剤は、CF3−O−(CF2)3−O−CHF−CF2−COOH、及びこの塩から選択される。具体例は、参照により本明細書に組み込まれる米国特許第7671112号(Hintzerら)に記載されている。例示的な乳化剤としては、CF3CF2OCF2CF2OCF2COOH、CHF2(CF2)5COOH、CF3(CF2)6COOH、CF3O(CF2)3OCF(CF3)COOH、CF3CF2CH2OCF2CH2OCF2COOH、CF3O(CF2)3OCHFCF2COOH、CF3O(CF2)3OCF2COOH、CF3(CF2)3(CH2CF2)2CF2CF2CF2COOH、CF3(CF2)2CH2(CF2)2COOH、CF3(CF2)2COOH、CF3(CF2)2OCF(CF3)CF2OCF(CF3)COOH、CF3(CF2)2(OCF2CF2)4OCF(CF3)COOH、CF3OCF2CF(CF3)OCF(CF3)COOH、C3F7OCF(CF3)COOH、CF3CF2O(CF2CF2O)3CF2COOH、及びこれらの塩が挙げられる。
(b) 少なくとも1つのBブロックであって、Bブロックは少なくとも1つのフッ素化モノマー及びニトリル含有硬化部位モノマーから誘導される繰り返しの二価モノマー単位を含むセグメントである、Bブロックと、
を有するフッ素化ブロックコポリマー
を含む硬化性組成物。
から誘導される、実施形態1〜16のいずれか1つに記載の硬化性組成物。
Claims (15)
- (c)少なくとも1つのAブロックであって、前記Aブロックは少なくとも1つのフッ素化モノマーから誘導される繰り返しの二価モノマー単位を含む半結晶性セグメントである、Aブロックと、
(d)少なくとも1つのBブロックであって、前記Bブロックは少なくとも1つのフッ素化モノマー及びニトリル含有硬化部位モノマーから誘導される繰り返しの二価モノマー単位を含むセグメントである、Bブロックと、
を有するフッ素化ブロックコポリマー
を含む、硬化性組成物。 - 前記ニトリル含有硬化部位モノマーが、CF2=CFO(CF2)5CN、CF2=CFOCF2CF(CF3)OCF2CF2CN、CF2=CFOCF2CF(CF3)OCF2CF(CF3)CN、CF2=CFOCF2CF2CF2OCF(CF3)CN、CF2=CFOCF2CF(CF3)OCF2CF2CN、及びこれらの組み合わせのうち少なくとも1つを含む、請求項1に記載の硬化性組成物。
- 前記AブロックがTFE、及び5wt%未満のコモノマーから誘導される、請求項1又は2に記載の硬化性組成物。
- 前記Aブロックが、TFE、HFP、及びVDFから誘導される、請求項1又は2に記載の硬化性組成物。
- 前記フッ素化ブロックコポリマーが、少なくとも100、及び最大で275℃の融点を有する、請求項1〜4のいずれか一項に記載の硬化性組成物。
- 前記Bブロックが、少なくともVDF、及び前記ニトリル含有硬化部位モノマーから誘導される、請求項1〜5のいずれか一項に記載の硬化性組成物。
- 前記Bブロックが半結晶性である、請求項1〜6のいずれか一項に記載の硬化性組成物。
- 前記Bブロックが非晶質である、請求項1〜6のいずれか一項に記載の硬化性組成物。
- 前記AブロックのTgが0℃より高く、80℃未満である、請求項1〜8のいずれか一項に記載の硬化性組成物。
- 前記BブロックのTgが0℃未満である、請求項1〜9のいずれか一項に記載の硬化性組成物。
- 前記フッ素化ブロックコポリマーが、前記フッ素化ブロックコポリマーの重量に基づいて、約0.05wt%〜約1wt%のヨウ素を含む、請求項1〜11のいずれか一項に記載の硬化性組成物。
- 過酸化物硬化系を更に含む、請求項1〜12のいずれか一項に記載の硬化性組成物。
- 前記フッ素化ブロックコポリマーのガラス転移温度が−20℃未満である、請求項1〜13のいずれか一項に記載の硬化性組成物。
- 請求項1〜14のいずれか一項に記載の硬化性組成物から誘導された硬化物品。
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2018
- 2018-01-12 JP JP2019558992A patent/JP2020504225A/ja active Pending
- 2018-01-12 CN CN201880007484.9A patent/CN110214155B/zh not_active Expired - Fee Related
- 2018-01-12 WO PCT/US2018/013496 patent/WO2018136324A1/en unknown
- 2018-01-12 US US16/477,006 patent/US11267922B2/en active Active
- 2018-01-12 EP EP18741235.8A patent/EP3571235A4/en not_active Withdrawn
Patent Citations (4)
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JPH10324788A (ja) * | 1997-05-26 | 1998-12-08 | Daikin Ind Ltd | 含フッ素エラストマー組成物 |
JPH11240997A (ja) * | 1997-12-15 | 1999-09-07 | Ausimont Spa | フッ素化熱可塑性エラストマー |
WO2007049469A1 (ja) * | 2005-10-27 | 2007-05-03 | Daikin Industries, Ltd. | 架橋性組成物およびそれからなる成形品 |
JP2013514438A (ja) * | 2009-12-17 | 2013-04-25 | スリーエム イノベイティブ プロパティズ カンパニー | ペルオキシド硬化された部分的にフッ素化されたエラストマー |
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EP3571235A1 (en) | 2019-11-27 |
CN110214155B (zh) | 2022-05-13 |
US11267922B2 (en) | 2022-03-08 |
EP3571235A4 (en) | 2020-11-11 |
WO2018136324A1 (en) | 2018-07-26 |
US20190352444A1 (en) | 2019-11-21 |
CN110214155A (zh) | 2019-09-06 |
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