JP2022507359A - ペルフルオロ脂環式メチルビニルエーテルのコポリマー - Google Patents
ペルフルオロ脂環式メチルビニルエーテルのコポリマー Download PDFInfo
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- JP2022507359A JP2022507359A JP2021526225A JP2021526225A JP2022507359A JP 2022507359 A JP2022507359 A JP 2022507359A JP 2021526225 A JP2021526225 A JP 2021526225A JP 2021526225 A JP2021526225 A JP 2021526225A JP 2022507359 A JP2022507359 A JP 2022507359A
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- JP
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- Prior art keywords
- perfluoropolymer
- vinyl ether
- fluoropolymer
- perfluoro
- ether
- 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.)
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- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 229920001577 copolymer Polymers 0.000 title description 8
- 229920005548 perfluoropolymer Polymers 0.000 claims abstract description 76
- -1 perfluoro Chemical group 0.000 claims abstract description 59
- 239000000178 monomer Substances 0.000 claims abstract description 57
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 12
- 238000002844 melting Methods 0.000 claims abstract description 11
- 230000008018 melting Effects 0.000 claims abstract description 11
- 230000000295 complement effect Effects 0.000 claims abstract description 5
- 229920002313 fluoropolymer Polymers 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- 239000004811 fluoropolymer Substances 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 21
- 238000002834 transmittance Methods 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 10
- 238000007334 copolymerization reaction Methods 0.000 claims description 10
- 230000009477 glass transition Effects 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- BIUZXWXXSCLGNK-UHFFFAOYSA-N ethenoxymethylcyclohexane Chemical compound C=COCC1CCCCC1 BIUZXWXXSCLGNK-UHFFFAOYSA-N 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- ODFPJHVZYSBZQO-UHFFFAOYSA-N ethenoxyethene;phosphoric acid Chemical class C=COC=C.OP(O)(O)=O ODFPJHVZYSBZQO-UHFFFAOYSA-N 0.000 claims 1
- KAYYMSTXKCZITA-UHFFFAOYSA-N ethenoxyethene;sulfuryl difluoride Chemical class C=COC=C.FS(F)(=O)=O KAYYMSTXKCZITA-UHFFFAOYSA-N 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 24
- 239000006185 dispersion Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 15
- 150000002696 manganese Chemical class 0.000 description 15
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000003999 initiator Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 238000000113 differential scanning calorimetry Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000007720 emulsion polymerization reaction Methods 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
- BZPCMSSQHRAJCC-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,5-nonafluoro-1-(1,2,3,3,4,4,5,5,5-nonafluoropent-1-enoxy)pent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F BZPCMSSQHRAJCC-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000000411 transmission spectrum Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000009792 diffusion process Methods 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 239000000758 substrate Substances 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 241001441571 Hiodontidae Species 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 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
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000005459 perfluorocyclohexyl group Chemical group 0.000 description 3
- 125000005385 peroxodisulfate group Chemical group 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical class C=CCOCC=C ATVJXMYDOSMEPO-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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000001351 cycling effect Effects 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 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
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000007348 radical reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000001429 visible spectrum Methods 0.000 description 2
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RKIMETXDACNTIE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorocyclohexane Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F RKIMETXDACNTIE-UHFFFAOYSA-N 0.000 description 1
- ZXFIBQNQPBGUGI-UHFFFAOYSA-N 1-(ethenoxymethyl)-1-methylcyclopentane Chemical class C=COCC1(C)CCCC1 ZXFIBQNQPBGUGI-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical class CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- XYFRHHAYSXIKGH-UHFFFAOYSA-N 3-(5-methoxy-2-methoxycarbonyl-1h-indol-3-yl)prop-2-enoic acid Chemical compound C1=C(OC)C=C2C(C=CC(O)=O)=C(C(=O)OC)NC2=C1 XYFRHHAYSXIKGH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZHYZWNVEGDAFNF-UHFFFAOYSA-N C(=C)OC(OC(F)(F)F)(F)F Chemical compound C(=C)OC(OC(F)(F)F)(F)F ZHYZWNVEGDAFNF-UHFFFAOYSA-N 0.000 description 1
- ZGUGJZRLDUWUMX-UHFFFAOYSA-N C(=C)OCC1CC(CC1)C Chemical compound C(=C)OCC1CC(CC1)C ZGUGJZRLDUWUMX-UHFFFAOYSA-N 0.000 description 1
- FGEGZNORXGGFML-UHFFFAOYSA-N C(C)C=COF Chemical compound C(C)C=COF FGEGZNORXGGFML-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- DMKDDYVOKBQCQC-UHFFFAOYSA-N FC(F)(OC=C)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F Chemical compound FC(F)(OC=C)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F DMKDDYVOKBQCQC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PDAVOLCVHOKLEO-UHFFFAOYSA-N acetyl benzenecarboperoxoate Chemical compound CC(=O)OOC(=O)C1=CC=CC=C1 PDAVOLCVHOKLEO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IWTBWSGPDGPTIB-UHFFFAOYSA-N butanoyl butaneperoxoate Chemical compound CCCC(=O)OOC(=O)CCC IWTBWSGPDGPTIB-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical compound FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- FOKCKXCUQFKNLD-UHFFFAOYSA-N pent-1-enyl hypofluorite Chemical compound C(CC)C=COF FOKCKXCUQFKNLD-UHFFFAOYSA-N 0.000 description 1
- 125000006551 perfluoro alkylene group Chemical group 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
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical compound CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- C—CHEMISTRY; METALLURGY
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Abstract
Description
Rf-CF2-[OCF(CF3)CF2]nO-CF=CF2 (I)
[式中、Rfは、6個の炭素原子、11個のフッ素原子、及び脂環式基を含む全フッ素化基であり、nは0,1,又は2である]によるモノマーから誘導された、実質的に融点を有しない、ペルフルオロポリマーが記載される。
用語「a」、「an」及び「the」は、互換的に用いられ、1つ以上を意味し、
用語「及び/又は」は、述べられた事柄の一方又は両方が起こり得ることを示すために用いられ、例えば、A及び/又はBは、(A及びB)並びに(A又はB)を含み、
「主鎖」は、ポリマーの開始及び終端の部位を除いた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つの異なるモノマーの重合を指し、トリポリマー(3つの異なるモノマー)、テトラポリマー(4つの異なるモノマー)などを含むことができる。
「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。
「相補的」は、ペルフルオロ(脂環式メチルビニルエーテル)モノマーのモル百分率と、コポリマー中に存在するTFE及び任意の他のモノマーのモル百分率とが、一緒になって100%になることを意味する。
「硬化部位」は、架橋に関与する場合がある、官能基を指す。
「共重合」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。
「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。
「全フッ素化」は、全ての水素原子がフッ素原子に置き換えられている、炭化水素から誘導された基、化合物、又は分子を意味する。しかし、全フッ素化化合物は、酸素原子、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」は、少なくとも50,000ダルトン、少なくとも100,000ダルトン、少なくとも300,000ダルトン、少なくとも500,000ダルトン、少なくとも750,000ダルトン、少なくとも1,000,000ダルトン、又は更には少なくとも1,500,000ダルトンであり、かつポリマーの早期ゲル化を引き起こすほどには高くない数平均分子量(Mn)を有するマクロ構造を指す。
[Rf-O-L-COO-]iXi +
[式中、Lは直鎖状の、部分若しく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は直鎖状の、部分若しくは完全フッ素化脂肪族基、又は1個以上の酸素原子が介在する直鎖状の、部分若しく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]に対応する。具体例については、例えば、米国特許第7,671,112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)2(OCF(CF3)CF2)OCF(CF3)COOH、CF3(CF2)2(OCF2CF2)4OCF(CF3)COOH、CF3CF2O(CF2CF2O)3CF2COOH、及びこれらの塩が挙げられる。一実施形態では、界面活性剤の分子量は、1500、1000、又は更には500グラム/モル未満である。
Claims (20)
- ペルフルオロポリマーであって、
少なくとも
(a)88mol%以下のテトラフルオロエチレンモノマー、及び
(b)相補量の式I
Rf-CF2-[OCF(CF3)CF2]n-O-CF=CF2
[式中、Rfは、6個の炭素原子、11個のフッ素原子、及び脂環式基を含む全フッ素化基であり、nは0,1,又は2である]によるモノマーから誘導された、
実質的に融点を有しない、ペルフルオロポリマー。 - 前記式Iのモノマーが、ペルフルオロ(シクロヘキシルメチルビニルエーテル)を含む、請求項1に記載のペルフルオロポリマー。
- 前記式Iのモノマーが、ペルフルオロ(シクロヘキシルメチルビニルエーテル)、ペルフルオロ(2-メチルシクロペンチルメチルビニルエーテル)、ペルフルオロ(3-メチルシクロペンチルメチルビニルエーテル)、ペルフルオロ(2-ジメチルシクロブチルメチルビニルエーテル)、及びペルフルオロ(3-ジメチルシクロブチルメチルビニルエーテル)のうちの少なくとも1つを含む、請求項1に記載のペルフルオロポリマー。
- 前記ペルフルオロポリマーが、ヘキサフルオロプロピレン、クロロトリフルオロエチレン、ペルフルオロアルキルビニルエーテル、ペルフルオロアルキルアリルエーテル、及びこれらの組み合わせのうちの少なくとも1つから更に誘導される、請求項1~3のいずれか一項に記載のペルフルオロポリマー。
- 前記ペルフルオロポリマーが、少なくとも10mol%のペルフルオロアルキルビニルエーテル、ペルフルオロアルキルアリルエーテル、又はこれらの組み合わせから更に誘導される、請求項4に記載のペルフルオロポリマー。
- 前記ペルフルオロポリマーが、少なくとも15mol%のペルフルオロ(脂環式メチルビニルエーテル)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ペルフルオロポリマー。
- 前記ペルフルオロポリマーが、全フッ素化ビニルエーテル酸、全フッ素化ビニルエーテルエステル、全フッ素化ビニルエーテルスルホネート、全フッ素化ビニルエーテルスルホニルフルオリド、全フッ素化ビニルエーテルホスフェート、又はこれらの組み合わせから更に誘導される、請求項1~6のいずれか一項に記載のペルフルオロポリマー。
- 前記ペルフルオロポリマーのガラス転移温度が室温より高い、請求項1~7のいずれか一項に記載のペルフルオロポリマー。
- 前記ペルフルオロポリマーが光学的に透明である、請求項1~8のいずれか一項に記載のペルフルオロポリマー。
- 前記ペルフルオロポリマーが、可視範囲全体にわたって少なくとも75%の平均正透過率を有する、請求項1~9のいずれか一項に記載のペルフルオロポリマー。
- 前記ペルフルオロポリマーが、可視範囲全体にわたって15%未満の平均ヘイズを有する、請求項1~10のいずれか一項に記載のペルフルオロポリマー。
- 前記ポリマーが、実質的に融点を有しない、請求項12に記載のフルオロポリマー。
- 前記ポリマーが室温より高いガラス転移温度を有する、請求項12又は13に記載のフルオロポリマー。
- 前記フルオロポリマーが光学的に透明である、請求項12~14のいずれか一項に記載のフルオロポリマー。
- 前記フルオロポリマーが、テトラフルオロエチレンから誘導された共重合単位を更に含む、請求項12~15のういずれか一項に記載のフルオロポリマー。
- 前記フルオロポリマーが、88モル%以下の、テトラフルオロエチレンから誘導された共重合単位を含む、請求項16に記載のフルオロポリマー。
- 前記フルオロポリマーが、全フッ素化ビニルエーテル酸、全フッ素化ビニルエーテルエステル、又はこれらの組み合わせから誘導された共重合単位を更に含む、請求項12~15のいずれか一項に記載のフルオロポリマー。
- 請求項12~18のいずれか一項に記載のフルオロポリマーを含む、組成物。
- 前記組成物がコーティングである、請求項19に記載の組成物。
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