JP2019515971A - 改善された親水性組成物 - Google Patents
改善された親水性組成物 Download PDFInfo
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- JP2019515971A JP2019515971A JP2018547347A JP2018547347A JP2019515971A JP 2019515971 A JP2019515971 A JP 2019515971A JP 2018547347 A JP2018547347 A JP 2018547347A JP 2018547347 A JP2018547347 A JP 2018547347A JP 2019515971 A JP2019515971 A JP 2019515971A
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- Prior art keywords
- copolymer
- comonomer mixture
- mixture
- water
- monomer
- 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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- 239000000203 mixture Substances 0.000 title claims abstract description 85
- 239000000178 monomer Substances 0.000 claims abstract description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 75
- 238000000034 method Methods 0.000 claims abstract description 61
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 43
- 239000004971 Cross linker Substances 0.000 claims abstract description 29
- 239000011149 active material Substances 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 229920001480 hydrophilic copolymer Polymers 0.000 claims abstract description 13
- 150000001450 anions Chemical class 0.000 claims abstract description 12
- 229920001577 copolymer Polymers 0.000 claims description 152
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 72
- 238000006703 hydration reaction Methods 0.000 claims description 53
- 230000036571 hydration Effects 0.000 claims description 52
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 32
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 18
- 239000003792 electrolyte Substances 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 10
- 239000000853 adhesive Substances 0.000 claims description 10
- 230000001070 adhesive effect Effects 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000003505 polymerization initiator Substances 0.000 claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 4
- 230000005693 optoelectronics Effects 0.000 claims description 4
- 238000010146 3D printing Methods 0.000 claims description 3
- 229910016467 AlCl 4 Inorganic materials 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229960002796 polystyrene sulfonate Drugs 0.000 claims description 3
- 239000011970 polystyrene sulfonate Substances 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 claims description 2
- FIQBJLHOPOSODG-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxycarbonyl]benzoic acid Chemical compound CC(=C)C(=O)OCCOC(=O)C1=CC=CC=C1C(O)=O FIQBJLHOPOSODG-UHFFFAOYSA-N 0.000 claims description 2
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 125000005399 allylmethacrylate group Chemical group 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 239000003431 cross linking reagent Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- 229920001197 polyacetylene Polymers 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 230000000887 hydrating effect Effects 0.000 claims 1
- 238000007641 inkjet printing Methods 0.000 claims 1
- 229920000767 polyaniline Polymers 0.000 claims 1
- 229920000128 polypyrrole Polymers 0.000 claims 1
- 238000007650 screen-printing Methods 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 53
- 239000011780 sodium chloride Substances 0.000 description 45
- 238000002484 cyclic voltammetry Methods 0.000 description 18
- 239000000463 material Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 9
- 229920001940 conductive polymer Polymers 0.000 description 7
- -1 1-hydroxy-2,2-dimethoxyethyl Chemical group 0.000 description 6
- 229920000144 PEDOT:PSS Polymers 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000002322 conducting polymer Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000011244 liquid electrolyte Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- BMQZYMYBQZGEEY-UHFFFAOYSA-M 1-ethyl-3-methylimidazolium chloride Chemical compound [Cl-].CCN1C=C[N+](C)=C1 BMQZYMYBQZGEEY-UHFFFAOYSA-M 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 230000002427 irreversible effect Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000006479 redox reaction Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000002355 dual-layer Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 230000001052 transient effect Effects 0.000 description 3
- 238000001075 voltammogram Methods 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000013626 chemical specie Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000007970 homogeneous dispersion Substances 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 229920001477 hydrophilic polymer Polymers 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000008093 supporting effect Effects 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- IXLWEDFOKSJYBD-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;methanesulfonate Chemical compound CS([O-])(=O)=O.CC[N+]=1C=CN(C)C=1 IXLWEDFOKSJYBD-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000000109 continuous material Substances 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- QFKWSRIUZIYLCK-UHFFFAOYSA-J copper;disodium;hydrogen carbonate;2-hydroxypropane-1,2,3-tricarboxylic acid;hydroxide;sulfate Chemical compound [OH-].[Na+].[Na+].[Cu+2].OC([O-])=O.[O-]S([O-])(=O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O QFKWSRIUZIYLCK-UHFFFAOYSA-J 0.000 description 1
- MKHFCTXNDRMIDR-UHFFFAOYSA-N cyanoiminomethylideneazanide;1-ethyl-3-methylimidazol-3-ium Chemical compound [N-]=C=NC#N.CCN1C=C[N+](C)=C1 MKHFCTXNDRMIDR-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000011263 electroactive material Substances 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 238000000157 electrochemical-induced impedance spectroscopy Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910021397 glassy carbon Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000004693 imidazolium salts Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XNUUJKJWYXTUTP-UHFFFAOYSA-N lanthanum ruthenium Chemical compound [Ru].[Ru].[La] XNUUJKJWYXTUTP-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229940068984 polyvinyl alcohol Drugs 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000009897 systematic effect Effects 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition 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
- C08F226/00—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C67/00—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y70/00—Materials specially adapted for additive manufacturing
-
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Abstract
Description
本発明は、改善された電子的に活性な親水性ポリマーおよびその製造に関する。
本来電子伝導性ポリマーは公知であり、伝導過程が主に電子移動に依存する材料を意味すると理解される。これは、伝導過程が主にイオン移動に依存するイオン電導性ポリマーとは対照的である。
特定の順序で混合された場合、少なくともひとつの疎水性モノマー、少なくともひとつの親水性モノマー、水、少なくともひとつの架橋剤、少なくともひとつの式(I)の化合物、および本質的に電子的活性な材料を含むコポリマー混合物は、(一度重合されると)新しい電子的に活性な親水性コポリマーを提供することを見出した。この材料は、導電性および水特性において均質で等方性である。それは、その構造全体にわたって、親水性であり、架橋され、電子伝導性である。
X−は陰イオン。
a.本質的に電子的活性な材料および少なくともひとつの式(I)の化合物を水と一緒に混合し中間混合物を形成する;
b.少なくともひとつの親水性モノマー、少なくともひとつの疎水性モノマーおよび少なくともひとつの架橋剤を中間混合物に添加してコモノマー混合物を形成する;
c.コモノマー混合物を重合させる;
式(I)は以下のように定義される:
X−は陰イオン。
X−は陰イオン。
本明細書で使用するとき、用語「モノマー」は、当技術分野での通常の定義をとり、別のモノマーと化学的に結合してポリマーを形成し得る分子化合物を指す。
本明細書で使用するとき、用語「コモノマー混合物」は、当該技術分野での通常の定義をとり、重合したときにコポリマーを形成する混和性モノマーの溶液または分散液を指す。
a.本質的に電子的活性な材料および少なくともひとつの式(I)の化合物を水と一緒に混合して中間混合物を形成する;
b.少なくともひとつの親水性モノマー、少なくともひとつの疎水性モノマーおよび少なくともひとつの架橋剤を中間混合物に添加してコモノマー混合物を形成する;
c.コモノマー混合物を重合させる;
式(I)は以下のように定義される:
X−は陰イオン。
好ましくは、電子的に活性な材料はポリマーである。
a.本質的に電子的活性な材料および少なくともひとつの式(I)の化合物を水と一緒に混合して中間混合物を形成する;
b.少なくともひとつの親水性モノマー、少なくともひとつの疎水性モノマーおよび少なくともひとつの架橋剤を中間混合物に添加してコモノマー混合物を形成する;
隣接する電気伝導性成分の間にコモノマー混合物を導入する;
c.該電気伝導性成分の間にin situでコモノマー混合物を重合させる;
式(I)は以下のように定義される:
X−が陰イオン。
1−エチル−3−メチルイミダゾリウムクロライドは、以後「CL−14」と呼ぶ。
親水性架橋コポリマーを実施例1と同じ方法で製造した。これらをa)生理食塩水(0.009g/cc DD水中のNaCl)およびb)食塩水(0.3g/cc 水中のNaCl)中で水和させた。
実施例1のコポリマーを、最大レベルの水和に達するまで水和させた(約80重量%の含水率に相当する)。水和直後に伝導率を測定し、水和後の様々な日数に続いて再度測定した。結果を表2(下記)および図2に示す。
実施例1のコポリマーを、最大レベルの水和に達するまで(約75重量%の含水率に対応する)食塩水中で水和させた。水和直後に伝導率を測定し、水和後の様々な日数に続いて再度測定した。結果を表3(下記)および図3に示す。
表2と同様の方法で表3の膨張率を算出した。
1−エチル(ethy)−3−メチルイミダゾリウムメタンスルホネートを以後ST−35という。
CL−14の代わりにST−35を用いた以外は実施例1と同様の方法を用いて親水性架橋コポリマーを得た。
架橋コポリマーを実施例2と同じ方法で製造した。次いでこれらをa)DD水およびb)硫酸溶液(濃度5mol/dm3)中で水和させた。
実施例2のコポリマーを、25℃で最大レベルの水和に達するまで水和した(約78重量%の含水率に相当する)。水和直後に伝導率を測定し、水和後7日に再び測定した。結果を表5(下記)および図5に示す。
表5の膨張率は、表2と同様に算出した。
実施例2のコポリマーを、最大レベルの水和に達するまで水和した(約84重量%の含水率に相当)。水和直後に伝導率を測定し、水和後7日に再び測定した。結果を表6(下記)および図6に示す。
表6の膨張率は、表2と同様に算出した。
3つの異なる比のビニルピロリドンとPEDOT−PSSを用いて3つのコポリマーを調製し、それらの電気伝導性を比較した。
得られたコモノマー混合物をUV下で硬化させて架橋コポリマーを製造した。
以下の表の用語は、実施例4〜9にわたり適用される:
VP:PEDOTPSS:Cl4コポリマーを実施例1〜3と同様の方法を用いてを調製した。コポリマーの電気的特性を試験した。結果を図10と図11に示す。図10と図11は、負電位(図10)または正電位(図11)限界のいずれかの関数としての100mVs−1でのサイクリックボルタモグラムである。破線は、コポリマー層における不可逆的構造変化(例えば、分解)に関連する非対称電流応答を示す。
VP:PEDOTPSS:Cl4コポリマーを実施例1〜3と同様の方法を用いて調製した。コポリマーの電気的特性を試験した。結果は、走査速度50、100、150および200mVs−1でのサイクリックボルタモグラムである図12に示す。
VP:PEDOTPSS:Cl4コポリマーを実施例1〜3と同様の方法を用いて調製した。ふたつの異なるフラット電極装置を用いて、コポリマーの電気的特性を試験した。これらのフラット電極装置は、電極の表面積において互いに異なる。結果を図17(電極表面積0.5cm2)および図18(電極表面積0.6cm2)に示す。図17および図18は、走査速度25、50、100、150および200mVs−1でのサイクリックボルタモグラムである。
4つのVP:PEDOTPSS:Cl4コポリマーを実施例1〜3と同様の方法を用いて調製した。次いで、第1のコポリマーをH2O中で水和させ、第2のコポリマーを生理食塩水中で水和させ、第3のコポリマーを食塩水で水和させ、第4のコポリマーをH2SO4で水和させた。これらの4種のコポリマーのそれぞれの電気特性を試験し、その結果を図19に示す。
ふたつのVP:PEDOTPSS:Cl4コポリマーを実施例1〜3と同様の方法を用いて調製した。次いで、第1のコポリマーをH2O中で水和させ、第2のコポリマーを生理食塩水中で水和させた。これらの2種のコポリマーのそれぞれの電気特性を試験した。結果を図22(H2O中で水和)および図23(生理食塩水中で水和)に示す。
図22および図23は、走査速度50、100、150および200mVs−1でのサイクリックボルタモグラムである。
VP:PEDOTPSS:ST35コポリマーを実施例1〜3と同様の方法を用いて調製した。次いで、コポリマーを生理食塩水中で水和させた。電気的特性を試験した。結果を図24と25に示す。図24は、1Vからさまざまな負電位までのクロノアンペロメトリックトランジェントである。図25は、電位ステップの振幅の関数としてトランジェントを積分することによって得られた電荷をプロットしている。これらの図の結果は、電解キャパシタンスを示す。特に、生理食塩水で水和されたVP:PEDOTPSS:ST35コポリマーは、0.010Fcm−2のオーダのキャパシタンスを示す。このキャパシタンス値は、水性電解質中の炭素電極の幾何学的キャパシタンスより3桁超えで大きい。
VP:PEDOTPSS:ST35コポリマーを実施例1〜3と同様の方法を用いて調製した。次いで、コポリマーを生理食塩水中で水和させた。電気的特性を試験した。結果を図26に示す。
Claims (44)
- 架橋された電子的に活性な親水性コポリマーを形成する方法であって、以下の工程を含む方法:
a.本質的に電子的活性な材料および少なくともひとつの式(I)の化合物を水と一緒に混合して中間混合物を形成する;
b.少なくともひとつの親水性モノマー、少なくともひとつの疎水性モノマーおよび少なくともひとつの架橋剤を中間混合物に添加してコモノマー混合物を形成する;
c.コモノマー混合物を重合させる;
式(I)は以下のように定義される:
式中:
R1およびR2は独立して、置換されてもよいC1−C6アルキル;
X−は陰イオン。 - X−が、Cl−、C2N3 −、CH3O3S−、BF4 −、PF6 −、CF3SO3 −、Al2Cl7 −、AlCl4 − NO3 −、OH−、F−、Br−、I−、S2 −、N3 −、O2 −、CO3 2−、ClO3 2−、CrO4 2−、CN−、Cr2O7 2−、SCN−、SO3 2−、MnO4 −、CH3COO−、HCO3 −、ClO4 −およびC2O4 2−から選択される、請求項1に記載の方法。
- X−が、Cl−、C2N3 −およびCH3O3S−から選択される、請求項2に記載の方法。
- 任意の置換基が、ヒドロキシル、ハロ、NH2、NO2、CH3O、CO2H、COOOH、NR、NRR’、NHCORおよびRSH(式中、RおよびR’はC1−C6アルキル)から選択される1つ以上である、先行するいずれかの請求項に記載の方法。
- R1およびR2のひとつが置換されてもよいメチルであり、他方が置換されてもよいエチルである、先行するいずれかの請求項に記載の方法。
- 工程bにおいて、架橋剤の添加の前に、少なくともひとつの親水性モノマーおよび少なくともひとつの疎水性モノマーを中間混合物に添加する、先行するいずれかの請求項に記載の方法。
- 工程bにおいて、少なくともひとつの疎水性モノマーの添加の前に、少なくともひとつの親水性モノマーを中間混合物に添加する、先行するいずれかの請求項に記載の方法。
- 本質的に電子的活性な材料が、ポリエチレンジオキシチオフェン:ポリスチレンスルホネート、ポリピロール、ポリアニリン、ポリアセチレンまたはその組み合わせから選択される、先行するいずれかの請求項に記載の方法。
- 本質的に電子的活性な材料が、ポリエチレンジオキシチオフェン:ポリスチレンスルホネートである、請求項8に記載の方法。
- 少なくともひとつの親水性モノマーが、メタアクリル酸、2−ヒドロキシエチルメタクリレート、エチルアクリレート、ビニルピロリドン、プロペン酸メチルエステル、モノメタクリロイルオキシエチルフタレート、アンモニウムスルファトエチル(sulphatoethyl)メタクリレート、ポリビニルアルコールまたはその組み合わせから選択される、先行するいずれかの請求項に記載の方法。
- 少なくともひとつの親水性モノマーが、ビニルピロリドンおよびヒドロキシエチルメタクリレートまたはその組み合わせから選択される、請求項10に記載の方法。
- 少なくともひとつの疎水性モノマーが、メチルメタクリレート、アリルメタクリレート、アクリロニトリル、メタクリルオキシプロピルトリス(トリメチルシロキシ)シラン、2,2,2−トリフルオロエチルメタクリレートまたはその組み合わせから選択される、先行するいずれかの請求項に記載の方法。
- 少なくともひとつの疎水性モノマーが、アクリロニトリルおよびメチルメタクリレート、またはその組み合わせから選択される、請求項12に記載の方法。
- 架橋剤が、アリルメタクリレートまたはエチレングリコールジメタクリレートである、先行するいずれかの請求項に記載の方法。
- 架橋剤および疎水性モノマーの両方が、アリルメタクリレートである、先行するいずれかの請求項に記載の方法。
- 重合工程が、サーマル、UVまたはガンマ線照射により行われる、先行するいずれかの請求項に記載の方法。
- 重合工程が、UVまたはガンマ線照射により行われる、請求項16に記載の方法。
- コモノマー混合物がさらに重合開始剤を含む、先行するいずれかの請求項に記載の方法。
- 重合開始剤が、アゾビスイソブチロニトリルまたは2−ヒドロキシ−2−メチルプリオフェノン(methylpriophenone)である請求項18に記載の方法。
- コモノマー混合物中の少なくともひとつの疎水性モノマーに対する少なくともひとつの親水性モノマーの比が、20:1〜1:1である、先行するいずれかの請求項に記載の方法。
- コモノマー混合物中の少なくともひとつの疎水性モノマーに対する少なくともひとつの親水性モノマーの比が、20:1〜5:1、好ましくは、10:1である、先行するいずれかの請求項に記載の方法。
- コモノマー混合物中の比;少なくともひとつの親水性モノマーおよび少なくともひとつの疎水性モノマー:本質的に電子的活性な材料が、30:1〜2:1である、先行するいずれかの請求項に記載の方法。
- コモノマー混合物中の比;少なくともひとつの親水性モノマーおよび少なくともひとつの疎水性モノマー:本質的に電子的活性な材料が、6:1〜3:1である、先行するいずれかの請求項に記載の方法。
- コモノマー混合物中の本質的に電子的活性な材料に対する水の比が、1:1〜10:1である、先行するいずれかの請求項に記載の方法。
- コモノマー混合物中の本質的に電子的活性な材料に対する水の比が、1:1〜3:1、好ましくは2:1である、先行するいずれかの請求項に記載の方法。
- さらに重合後コポリマーを水和させる工程を含む、先行するいずれかの請求項に記載の方法。
- コポリマーの水和に続いて少なくとも7日間保存する、先行するいずれかの請求項に記載の方法。
- コポリマーを水和し、水和されたコポリマーの合計重量に対して少なくとも10重量%の水を含むように水和する、請求項26または17に記載の方法。
- 先行するいずれかの請求項に記載の方法によって得られうる、均質で等方性の電子的に活性な親水性コポリマー。
- 少なくともひとつの疎水性モノマー、少なくともひとつの親水性モノマー、水、少なくともひとつの架橋剤、本質的に電子的活性な材料および少なくともひとつの式(I)の化合物を含むコモノマー混合物であって、式(I)は以下のように定義されるコモノマー混合物:
(式中、
R1およびR2は独立して置換されてもよいC1−C6アルキル;
X−は陰イオン)。 - 請求項2〜15または18〜25の追加の特徴のいずれかひとつを有する、請求項30に記載のコモノマー混合物。
- 3Dプリンティングにおける、請求項30または請求項31に記載のコモノマー混合物の使用であって、コモノマー混合物が重合されて3D画像を形成する、使用。
- 3Dプリンティングが、スクリーン印刷システムまたはインクジェット印刷システムを使用する、請求項32に記載の使用。
- 水性電解質および請求項29に記載のコポリマーを含む、電池。
- 電池が鉛蓄電池である、請求項34の電池。
- 水または水性電解質、および請求項29に記載のコポリマーを含む、電気化学セル。
- 請求項29に記載のコポリマーを含む、光電子ディスプレイデバイスであって、好ましくはフレキシブルである光電子ディスプレイデバイス。
- 請求項29に記載のコポリマーを含む、携帯電話のスクリーンまたはコンピュータのスクリーン。
- 請求項29に記載のコポリマーを含む、電気伝導性接着ジャンクションであって、隣接する電気伝導性成分の間に位置する接着ジャンクション。
- 電気伝導性接着ジャンクションを形成する方法であって、以下の工程を含む:
a.本質的に電子的活性な材料および少なくともひとつの式(I)の化合物を水と一緒に混合して中間混合物を形成する;
b.少なくともひとつの親水性モノマー、少なくともひとつの疎水性モノマーおよび少なくともひとつの架橋剤を中間混合物に添加してコモノマー混合物を形成する;
コモノマー混合物を隣接する電気伝導性成分の間に導入する;
c.コモノマー混合物をin situで前記電気伝導性成分の間に重合させる;
式(I)は以下のように定義される:
(式中:
R1およびR2は独立して、置換されてもよいC1−C6アルキル;
X−は陰イオン)。 - 請求項2〜28に規定の追加の特徴のいずれかを含む請求項40の方法。
- 請求項40または41の方法により形成される、電気伝導性接着ジャンクション。
- 2本の電極およびそれらの間に存在する請求項29に記載のコポリマーを含む、スーパーキャパシタ。
- その構造全体にわたって分散された化学成分と一緒に請求項29に記載のコポリマーを含むセンシングシステムであって、該化学成分が特定の化合物を検知しうるセンシングシステム。
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CN104952634B (zh) | 2015-06-05 | 2019-07-19 | 北京大学 | 一种离子液体-锂盐凝胶聚合物电解质及其制备和应用 |
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JP2024009802A (ja) | 2024-01-23 |
NZ745563A (en) | 2022-04-29 |
AU2016397051A1 (en) | 2018-09-13 |
CA3015289A1 (en) | 2017-09-14 |
JP2021185227A (ja) | 2021-12-09 |
CN109153755A (zh) | 2019-01-04 |
US11168167B2 (en) | 2021-11-09 |
US20190062481A1 (en) | 2019-02-28 |
CN109153755B (zh) | 2020-12-22 |
KR20180123033A (ko) | 2018-11-14 |
JP7471773B2 (ja) | 2024-04-22 |
RU2739035C2 (ru) | 2020-12-21 |
US20220002462A1 (en) | 2022-01-06 |
RU2018134080A (ru) | 2020-04-13 |
RU2018134080A3 (ja) | 2020-04-13 |
US11702496B2 (en) | 2023-07-18 |
EP3426703A1 (en) | 2019-01-16 |
MX2018010647A (es) | 2019-01-30 |
GB201604249D0 (en) | 2016-04-27 |
AU2016397051B2 (en) | 2021-09-09 |
WO2017153706A1 (en) | 2017-09-14 |
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