JP6147860B2 - 銀ナノ構造を作製するための方法及び同方法に有用なコポリマー - Google Patents
銀ナノ構造を作製するための方法及び同方法に有用なコポリマー Download PDFInfo
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- JP6147860B2 JP6147860B2 JP2015534769A JP2015534769A JP6147860B2 JP 6147860 B2 JP6147860 B2 JP 6147860B2 JP 2015534769 A JP2015534769 A JP 2015534769A JP 2015534769 A JP2015534769 A JP 2015534769A JP 6147860 B2 JP6147860 B2 JP 6147860B2
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- silver
- copolymer
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- nitrate
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- 229920001577 copolymer Polymers 0.000 title claims description 104
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 title claims description 102
- 239000002086 nanomaterial Substances 0.000 title claims description 54
- 238000000034 method Methods 0.000 title claims description 52
- 239000004332 silver Substances 0.000 title claims description 50
- 229910052709 silver Inorganic materials 0.000 title claims description 50
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 108
- 239000000178 monomer Substances 0.000 claims description 105
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 63
- 239000011541 reaction mixture Substances 0.000 claims description 46
- -1 pyrrolidinedionyl moiety Chemical group 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 41
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 37
- 229940100890 silver compound Drugs 0.000 claims description 37
- 150000003379 silver compounds Chemical class 0.000 claims description 37
- 229920005862 polyol Polymers 0.000 claims description 34
- 150000003077 polyols Chemical class 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 125000002091 cationic group Chemical group 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000004442 acylamino group Chemical group 0.000 claims description 13
- 229910002651 NO3 Inorganic materials 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- YIOJGTBNHQAVBO-UHFFFAOYSA-N dimethyl-bis(prop-2-enyl)azanium Chemical compound C=CC[N+](C)(C)CC=C YIOJGTBNHQAVBO-UHFFFAOYSA-N 0.000 claims description 10
- 238000010526 radical polymerization reaction Methods 0.000 claims description 9
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 8
- 229940006460 bromide ion Drugs 0.000 claims description 8
- 229920005604 random copolymer Polymers 0.000 claims description 8
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims description 6
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 claims description 5
- ZFDWHYHVOHHJJE-UHFFFAOYSA-N 2-ethenyl-1h-imidazole;nitric acid Chemical compound O[N+]([O-])=O.C=CC1=NC=CN1 ZFDWHYHVOHHJJE-UHFFFAOYSA-N 0.000 claims description 2
- PTUBECUMTLTQAX-UHFFFAOYSA-N nitric acid;prop-2-enoic acid Chemical compound O[N+]([O-])=O.OC(=O)C=C PTUBECUMTLTQAX-UHFFFAOYSA-N 0.000 claims description 2
- 150000004767 nitrides Chemical class 0.000 claims 1
- 239000002070 nanowire Substances 0.000 description 59
- 239000002042 Silver nanowire Substances 0.000 description 44
- 229920000642 polymer Polymers 0.000 description 32
- 101710134784 Agnoprotein Proteins 0.000 description 30
- 239000000470 constituent Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 22
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 19
- 229920001940 conductive polymer Polymers 0.000 description 19
- 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 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 229910021607 Silver chloride Inorganic materials 0.000 description 14
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 125000000129 anionic group Chemical group 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 229920001519 homopolymer Polymers 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 230000000379 polymerizing effect Effects 0.000 description 9
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 8
- 238000005755 formation reaction Methods 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 7
- 230000005484 gravity Effects 0.000 description 7
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 7
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000002105 nanoparticle Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical group C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- 125000002015 acyclic group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000012527 feed solution Substances 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229940117986 sulfobetaine Drugs 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- 238000000954 titration curve Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000002632 imidazolidinyl group Chemical group 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000004193 piperazinyl group Chemical group 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- 229920002959 polymer blend Polymers 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 3
- 125000002755 pyrazolinyl group Chemical group 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 3
- 125000001422 pyrrolinyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- KANZWHBYRHQMKZ-UHFFFAOYSA-N 2-ethenylpyrazine Chemical compound C=CC1=CN=CC=N1 KANZWHBYRHQMKZ-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000003917 TEM image Methods 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- RYZCLUQMCYZBJQ-UHFFFAOYSA-H lead(2+);dicarbonate;dihydroxide Chemical compound [OH-].[OH-].[Pb+2].[Pb+2].[Pb+2].[O-]C([O-])=O.[O-]C([O-])=O RYZCLUQMCYZBJQ-UHFFFAOYSA-H 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 150000003378 silver Chemical class 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 238000003260 vortexing Methods 0.000 description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
- NLNUDODFFAWTHQ-UHFFFAOYSA-N 1-ethenyl-2,3-dihydropyrrole Chemical compound C=CN1CCC=C1 NLNUDODFFAWTHQ-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- DCRYNQTXGUTACA-UHFFFAOYSA-N 1-ethenylpiperazine Chemical compound C=CN1CCNCC1 DCRYNQTXGUTACA-UHFFFAOYSA-N 0.000 description 1
- LEWNYOKWUAYXPI-UHFFFAOYSA-N 1-ethenylpiperidine Chemical compound C=CN1CCCCC1 LEWNYOKWUAYXPI-UHFFFAOYSA-N 0.000 description 1
- IPOCWQUFTIXMIQ-UHFFFAOYSA-N 1-ethenylpyrazolidine Chemical compound C=CN1CCCN1 IPOCWQUFTIXMIQ-UHFFFAOYSA-N 0.000 description 1
- UDJZTGMLYITLIQ-UHFFFAOYSA-N 1-ethenylpyrrolidine Chemical compound C=CN1CCCC1 UDJZTGMLYITLIQ-UHFFFAOYSA-N 0.000 description 1
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- IJSCYIZQNHIKIU-UHFFFAOYSA-N 2-ethenyl-1,3-dihydropyrazole Chemical compound C=CN1CC=CN1 IJSCYIZQNHIKIU-UHFFFAOYSA-N 0.000 description 1
- MLMGJTAJUDSUKA-UHFFFAOYSA-N 2-ethenyl-1h-imidazole Chemical class C=CC1=NC=CN1 MLMGJTAJUDSUKA-UHFFFAOYSA-N 0.000 description 1
- VMSBGXAJJLPWKV-UHFFFAOYSA-N 2-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=C VMSBGXAJJLPWKV-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- BCAIDFOKQCVACE-UHFFFAOYSA-N 3-[dimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azaniumyl]propane-1-sulfonate Chemical compound CC(=C)C(=O)OCC[N+](C)(C)CCCS([O-])(=O)=O BCAIDFOKQCVACE-UHFFFAOYSA-N 0.000 description 1
- DTYXUWCJYMNDQD-UHFFFAOYSA-N 3-ethenylpyridazine Chemical compound C=CC1=CC=CN=N1 DTYXUWCJYMNDQD-UHFFFAOYSA-N 0.000 description 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 101710141544 Allatotropin-related peptide Proteins 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- QWRQLAHXFWHKAQ-UHFFFAOYSA-N B([O-])([O-])[O-].CC1=CC(=NN1)C.CC1=CC(=NN1)C.CC1=CC(=NN1)C.[Ag+3] Chemical compound B([O-])([O-])[O-].CC1=CC(=NN1)C.CC1=CC(=NN1)C.CC1=CC(=NN1)C.[Ag+3] QWRQLAHXFWHKAQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005227 alkyl sulfonate group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- YVEJDOBFMBXLPV-UHFFFAOYSA-N benzyl-dimethyl-prop-2-enylazanium Chemical class C=CC[N+](C)(C)CC1=CC=CC=C1 YVEJDOBFMBXLPV-UHFFFAOYSA-N 0.000 description 1
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- 229920001400 block copolymer Polymers 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 229910001622 calcium bromide Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- ITALYRUPPRAMMN-UHFFFAOYSA-N carboxymethyl-dimethyl-[3-(prop-2-enoylamino)propyl]azanium;bromide Chemical compound [Br-].OC(=O)C[N+](C)(C)CCCNC(=O)C=C ITALYRUPPRAMMN-UHFFFAOYSA-N 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([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
- 238000005259 measurement Methods 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000399 optical microscopy Methods 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920002580 poly(selenophene-2,5-diyl) polymer Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229940071575 silver citrate Drugs 0.000 description 1
- KKKDGYXNGYJJRX-UHFFFAOYSA-M silver nitrite Chemical compound [Ag+].[O-]N=O KKKDGYXNGYJJRX-UHFFFAOYSA-M 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- FJOLTQXXWSRAIX-UHFFFAOYSA-K silver phosphate Chemical compound [Ag+].[Ag+].[Ag+].[O-]P([O-])([O-])=O FJOLTQXXWSRAIX-UHFFFAOYSA-K 0.000 description 1
- 229910000161 silver phosphate Inorganic materials 0.000 description 1
- 229940019931 silver phosphate Drugs 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
- RUJQWQMCBPWFDO-UHFFFAOYSA-M silver;2-hydroxyacetate Chemical compound [Ag+].OCC([O-])=O RUJQWQMCBPWFDO-UHFFFAOYSA-M 0.000 description 1
- LMEWRZSPCQHBOB-UHFFFAOYSA-M silver;2-hydroxypropanoate Chemical compound [Ag+].CC(O)C([O-])=O LMEWRZSPCQHBOB-UHFFFAOYSA-M 0.000 description 1
- JKOCEVIXVMBKJA-UHFFFAOYSA-M silver;butanoate Chemical compound [Ag+].CCCC([O-])=O JKOCEVIXVMBKJA-UHFFFAOYSA-M 0.000 description 1
- FTNNQMMAOFBTNJ-UHFFFAOYSA-M silver;formate Chemical compound [Ag+].[O-]C=O FTNNQMMAOFBTNJ-UHFFFAOYSA-M 0.000 description 1
- UKHWJBVVWVYFEY-UHFFFAOYSA-M silver;hydroxide Chemical compound [OH-].[Ag+] UKHWJBVVWVYFEY-UHFFFAOYSA-M 0.000 description 1
- CYLMOXYXYHNGHZ-UHFFFAOYSA-M silver;propanoate Chemical compound [Ag+].CCC([O-])=O CYLMOXYXYHNGHZ-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 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
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- QUTYHQJYVDNJJA-UHFFFAOYSA-K trisilver;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Ag+].[Ag+].[Ag+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QUTYHQJYVDNJJA-UHFFFAOYSA-K 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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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
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F1/00—Metallic powder; Treatment of metallic powder, e.g. to facilitate working or to improve properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F1/00—Metallic powder; Treatment of metallic powder, e.g. to facilitate working or to improve properties
- B22F1/07—Metallic powder characterised by particles having a nanoscale microstructure
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F9/00—Making metallic powder or suspensions thereof
- B22F9/16—Making metallic powder or suspensions thereof using chemical processes
- B22F9/18—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F9/00—Making metallic powder or suspensions thereof
- B22F9/16—Making metallic powder or suspensions thereof using chemical processes
- B22F9/18—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds
- B22F9/24—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds starting from liquid metal compounds, e.g. solutions
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/02—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of metals or alloys
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
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Description
本出願は、2012年9月27日出願の米国仮出願第61/706280号の優先権を主張するPCT国際出願であり、前記米国仮出願の内容全体は本明細書に包含される。
(a)塩化物又は臭化物イオン源、及び
(b)
(i)一又は複数の第1の構成繰り返し単位であって、各々が独立に、一の構成繰り返し単位につき少なくとも一の、ペンダント飽和又は不飽和の、5員、6員、又は7員、アシルアミノ又はジアシルアミノ含有複素環式環部分を含む第1の構成繰り返し単位と、
(ii)一又は複数の第2の構成繰り返し単位であって、各々が独立に、一又は複数の第1の非イオン性構成繰り返し単位とは異なる第2の構成繰り返し単位と
を含み、且つ1モルにつき約500グラム以上の分子量を有する少なくとも一のコポリマー
の存在下において反応させることを含む方法を目的とする。
800〜999の第1の構成繰り返し単位であって、各々が独立に、一の構成繰り返し単位につき少なくとも一の、ペンダント飽和又は不飽和の、5員、6員、又は7員、アシルアミノ又はジアシルアミノ含有複素環式環部分を含む第1の構成繰り返し単位と、
1〜200の第2の構成繰り返し単位であって、各々が独立に、(i)イオン性有機質部分及び非イオン性有機質部分から選択され、且つ(ii)飽和又は不飽和の、5員、6員、又は7員、アシルアミノ又はジアシルアミノ含有複素環式環部分ではない
少なくとも一のペンダント有機質部分を含み、1モルにつき約500グラム以上の分子量を有する第2の構成繰り返し単位と
を含むコポリマーを目的とする。
(a)塩化物又は臭化物イオン源、
(b)
(i)一又は複数の第1の構成繰り返し単位であって、各々が独立に、一の構成繰り返し単位につき少なくとも一の、ペンダント飽和又は不飽和の、5員、6員、又は7員、アシルアミノ又はジアシルアミノ含有複素環式環部分を含む第1の構成繰り返し単位と、
(ii)一又は複数の第2の構成繰り返し単位であって、各々が独立に、一又は複数の第1の非イオン性構成繰り返し単位とは異なる第2の構成繰り返し単位と
を含み、且つ1モルにつき約500グラム以上の分子量を有する少なくとも一のコポリマー、並びに
(c)少なくとも一の塩基
の存在下において反応させることを含む方法を目的とする。
本明細書において電気伝導性ポリマーに言及して使用される「ドープされた」とは、電気伝導性ポリマーが電気伝導性ポリマーに対するポリマー対イオンと組み合わされていることを意味し、このポリマー対イオンは、本明細書において「ドーパント」と呼ばれ、典型的にはポリマー酸である。このポリマー酸は、本明細書では「ポリマー酸ドーパント」と呼ばれ、
「ドープされた電気伝導性ポリマー」は、電気伝導性ポリマーと、電気伝導性ポリマーのポリマー対イオンとを含むポリマーブレンドを意味し、
「電気伝導性ポリマー」は、カーボンブラック又は導電性金属粒子といった電気伝導性充填剤を添加しなくとも、本質的に又は天然に、電気伝導能を有する任意のポリマー又はポリマーブレンドを意味し、典型的には、1cm当たり10−7ジーメンス(「S/cm」)以上のかさ特異的コンダクタンスを呈する任意のポリマー又はオリゴマーを意味し、別途指示されない限り、本明細書において、「電気的伝導性ポリマー」と言った場合、任意の随意的ポリマー酸ドーパントが含まれ、
「電気伝導性」は伝導性及び半伝導性を含み、
「電子機器」は、一又は複数の半導体材料を含む一又は複数の層を含み、この一又は複数の層を通して制御された電子の動きを利用する機器を意味し、
本明細書において電子機器に言及して使用される「層」は、機器の所望のエリアを覆うコーティングを意味し、ここでこのエリアは大きさによって限定されず、すなわち、層によって覆われるエリアは、例えば、装置全体と同じ大きさでも、実際の視覚的ディスプレイといった装置の特定の機能エリアと同じ大きさでも、又は単一のサブピクセルと同じ大きさでもよい。
「アルキル」は、一価の、直鎖状、分枝状、又は環状の飽和炭化水素基を意味し、典型的には、例えば、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、tert−ブチル、ヘキシル、オクチル、ヘキサデシル、オクタデシル、エイコシル、ベヘニル、トリコンチル(tricontyl)、及びトラコンチルといった、一価の、直鎖状又は分枝状の飽和(C1−C40)炭化水素基を意味し、
「シクロアルキル」は、飽和炭化水素基を意味し、典型的には、一又は複数の環式アルキル環を含む飽和(C5−C22)炭化水素基を意味し、環の一又は複数の炭素原子は、一の炭素原子につき一又は二の(C1−C6)アルキル基、例えば、シクロペンチル、シクロへプチル、シクロオクチルなどで置換されていてもよく、
「ヘテロアルキル」は、アルキル基内の一又は複数の炭素原子が、窒素、酸素、又は硫黄といったヘテロ原子によって置換されているアルキル基を意味し、
「ヘテロ環式」は、環炭素原子のうちの一又は複数が、窒素、酸素、又は硫黄といったヘテロ原子によって置換されている環状炭化水素基を意味し、
「アルキレン」は、例えば、メチレン、及びポリ(メチレン)を含む二価のアルキル基を指し、
「アルケニル」は、不飽和の直鎖状又は分枝状炭化水素基を意味し、典型的には、例えば、エテニル、n−プロペニル、及びイソ−プロペニルを含む一又は複数の炭素−炭素二重結合を含有する不飽和の直鎖状、分枝状の(C2−C22)炭化水素基を意味し、
「アリール」は、不飽和が3つのコンジュゲートした炭素−炭素二重結合によって表される、一又は複数の6員炭素環を含有する不飽和炭化水素基を意味し、ここで、環の炭素のうちの一又は複数が、一又は複数のヒドロキシ、アルキル、アルケニル、アルコキシ、ハロ、又はアルキルハロ置換基、例えば、フェニル、メチルフェニル、トリメチルフェニル、ノニルフェニル、クロロフェニル、トリクロロメチルフェニル、ナフチル、及びアントリルで置換されていてもよく、
「アラルキル」は、一又は複数のアリール基で置換されたアルキル基を意味し、典型的には、一又は複数の(C6−C14)アリール置換基、例えば、フェニルメチル、フェニルエチル、及びトリフェニルメチルで置換された(C1−C18)アルキルを意味し、
有機基に関して「(Cx−Cy)」(x及びyはそれぞれ整数)と言う場合、基が、1つの基についてx個からy個の炭素原子を含有しうることを意味する。
「カチオン」とは、部分が正味の正の電荷を有していることを意味し、
「アニオン」とは、部分が正味の負の電荷を有していることを意味し、
「両性」及び「両性イオン」とは、部分が正味の電荷を有していないが、又は特定のpH条件下においては、局所的な負の電荷及び局所的な正の電荷を有しうることを意味し、
「非イオン性」とは、部分が、正味の電荷も、局所的な負の電荷も、局所的な正の電荷も有さないことを意味する。
「構成繰り返し単位」は、最小の構成単位を意味し、その繰り返しはポリマー又はコポリマー分子の鎖又はブロックを構成し、
「構成単位」は、ペンダント原子又は基を含む一の原子又は原子の基を意味し、存在する場合、ポリマー若しくはコポリマー分子の基本構造、又はポリマー若しくはコポリマー分子のブロック又は鎖を含み、
「鎖」は、二の境界構成単位間に一又は複数の構成単位の直鎖状又は分枝状配列を含むポリマー又はコポリマー分子の全部又は一部を意味し、それらの各々はポリマー又はコポリマー分子の末端基、枝分かれ部位、又はそれ以外に指定される特徴的機能のいずれかであり、
コポリマーに関して「ブロック」と言う場合、同じコポリマーの隣接する部分には存在しない少なくとも一の特徴を有する二以上の構成単位を含むコポリマーの一部を意味する。
R1−R2− (I)
によるペンダント基を含み、
ここで:
R1は、飽和又は不飽和の、5員、6員、又は7員アシルアミノ又はジアシルアミノ含有複素環式環部分、典型的にはピロリドニル、2,5 ピロリジンジオニル、アザシクロヘキサノイル、アザシクロヘキサジオニル、アザシクロヘプタノイル(azacycloheptanonyl)、アザシクロヘプタジオニル、さらに典型的にはピロリドニル又は2,5 ピロリジンジオニルであり、
R2は、二価の結合基、典型的にはポリ(アルキレンオキシ)、−O-C(O)−、−NH−C(O)−及び−(CH2)n−(nは1〜10の整数、典型的には1〜3の整数)から選択される二価の結合基であるか、又は不在である。
R1−R2−R3 (II)
による一又は複数の化合物を含み、
ここで:
R1及びR2は上述の通りであり、
R3は反応性官能基、典型的には−CH2=CH2、及び−H(CH3)C=CH2から選択される反応基である。
一の基につき少なくとも一の一級、二級、又は三級アミノ窒素原子、又は四級窒素原子を含む非環基、並びに
環員として四級窒素原子でありうる少なくとも一の窒素原子を含む、5員又は6員複素環式環含有基から選択されるものを含む。
R20−R21− (III)
による部分を含む非環部分を含み、
ここで:
R20は、飽和又は不飽和の、5員、6員、又は7員、アシルアミノ又はジアシルアミノ含有複素環式環部分ではないイオン性有機質部分又は非イオン性有機質部分であり、
R21は、二価の結合基、典型的には、ポリ(アルキレンオキシ)、−O-C(O)−、−NH−C(O)−及び−(CH2)m−(mは1〜10の整数であり、典型的には1〜3の整数である)から選択される二価の結合基であるか、又は不在である。
一の基につき少なくとも一の一級、二級、又は三級アミノ窒素原子、又は四級窒素原子を含む非環基、並びに
例えば、環員として、ピロリジニル、ピロリニル、イミダゾリジニル、ピロリル、イミダゾリル、ピラゾリジニル、ピラゾリニル、ピペリジニル、ピペラジニル、ピリジニル、ピラジニル、ピリマジニル(pyrimadinyl)、又はピリダジニル部分などの、四級窒素原子でありうる少なくとも一の窒素原子を含む5員又は6員複素環式環含有基
から選択される。
R20−R21−R22 (IV)
による一又は複数の化合物を含み、
ここで:
R20及びR21は各々が上述の通りであり、
R22は反応性官能基、典型的には−CH2=CH2、及び−H(CH3)C=CH2から選択される反応基である。
500〜999の、典型的には800〜999の、さらに典型的には900〜990の、第1の構成繰り返し単位と、
1〜500の、典型的には1〜200の、さらに典型的には10〜100の、第2の構成繰り返し単位と
を含む。
(a)各々が独立に、一分子について少なくとも一の 反応性官能基と、少なくとも一のペンダント飽和又は不飽和、5員、6員、又は7員アシルアミノ又はジアシルアミノ含有複素環式環部分を含む、800〜999モルの一又は複数の第1のモノマー、並びに
(b)各々が独立に、一分子について少なくとも一の反応性官能基と、一分子について少なくとも一の一級、二級、又は三級アミノ窒素原子、又は四級窒素原子とを含む少なくとも一のペンダント有機質部分とを含む1〜200モルの一又は複数の第2のモノマー
を含むモノマー混合物を重合することにより作製される。
実施例1A−1Eのポリ(ビニルピロリドン−co−ジアリルジメチルアンモニウム ナイトレート)ランダムコポリマー(「ポリ(VP−co−DADMAN」)は、それぞれビニルピロリドンモノマーをジアリルジメチルアンモニウム ナイトレートモノマー(「DADMAN」)と共重合することにより作製された。
各交換は素早く生じ、遠心分離(2000rpmで5分)によりDAMANモノマー生産物溶液から容易に分離される白色の塩化銀の沈殿物を生み出した。沈殿物は水5mlで一度洗浄し、すべてのモノマーを回収するために再び遠心分離した。次いで、交換されたすべてのモノマー溶液は、後述するように、共重合反応に使用される前に0.2μmのフィルターで濾過された。
・ t=0において、前記溶液に2mlのAIBN/VP溶液が添加された。
・ t=20分において、発熱重合反応により温度は約75℃に上昇しており、0.5mlのAIBN/VP溶液が添加された。
・ t=55分において、反応器内の温度は約78℃であり、予め68℃に加熱された150mlの水が、残りのAIBN/VP溶液と共に反応混合物に添加された。
実施例2A−2Gの銀ナノワイヤーは、コポリマーの構成成分及び反応混合物に添加される硝酸銀の量が変更された、後述の一般的合成方法に従って作製された。いずれの場合も、実施例1A−1Eのポリ(VP−co−DADMAN)コポリマーのそれぞれは保護材として使用された。
実施例3A−3Cの銀ナノ構造は、概ね上述の実施例2A−2Gのナノワイヤーの作製に使用された方法に従って、実施例1Eのポリ(VP−co−DADMAN)コポリマー0.5g(DADMAN含有量16wt%)を使用し、但し反応混合物に添加される硝酸銀の量を変更して作製された。生成されたナノ構造の長さの分布は、光学顕微鏡で取得された写真に画像解析ソフトウェア「ImageJ」を用いて決定された。
実施例4A及び4Bの銀ナノワイヤーは、実施例2A−2Gにおいて上述された方法に従い、1wt%のDAMAN含有量を有するポリ(VP−co−DADMAN)を用いて、二つの異なるAgNO3量で作製された。
1wt%のDADMAN含有量を有するポリ(VP−co−DADMAN)の還元水合成
ポリ(VP−co−DADMAN)の合成は二つの工程からなる:
1wt%のDADMAN含有量を有するポリ(VP−co−DADMAN)の代替的還元水の合成
ポリ(VP−co−DADMAN)の合成は二つの工程からなる:
塩基の添加を必要とするエチレングリコールにポリ(VP−co−DADMAN)を使用して、高いアスペクト比の銀ナノワイヤーが獲得された。
実施例8の銀ナノワイヤーは、実施例7の銀ナノワイヤーの作製に使用された方法と類似であるが、但しLiOHを5.8mgの水酸化カリウム(KOH)で置き換えた方法により作製された。
実施例9の銀ナノワイヤーは、実施例7の銀ナノワイヤーの作製に使用された方法と類似であるが、但しLiOHを4.1mgの水酸化ナトリウム(NaOH)で置き換えた方法により作製された。
Claims (6)
- 銀ナノ構造を作製するための方法であって、少なくとも一のポリオールと、還元されると銀金属を生み出すことのできる少なくとも一の銀化合物とを、
(a)塩化物又は臭化物イオン源、及び
(b)
(i)一又は複数の第1の構成繰り返し単位であって、各々が独立に、一の第1の構成繰り返し単位につき少なくとも一の、ペンダント飽和又は不飽和の、5員、6員、又は7員、アシルアミノ又はジアシルアミノ含有複素環式環部分を含む第1の構成繰り返し単位と、
(ii)一又は複数の第2の構成繰り返し単位であって、各々が独立に、一又は複数の第1の構成繰り返し単位とは異なり、四級アンモニア性窒素原子を含む少なくとも一のペンダントカチオン性部分と窒化物対アニオンとを含む、第2の構成繰り返し単位と
を含み、且つ1モルにつき約500グラム以上の分子量を有する少なくとも一のコポリマー
の存在下で反応させることを含む方法。 - コポリマーの第1の構成繰り返し単位が、各々独立にピロリドニル部分又はピロリジンジオニル部分を含む、請求項1に記載の方法。
- コポリマーが、
ビニルピロリドン、ビニルカプロラクタム、又はビニルピロリドン及びビニルカプロラクタムと、
第2構成繰り返し単位の一又は複数のエチレン性不飽和カチオン性モノマーとの遊離ラジカル重合により作製されるランダムコポリマーである、請求項2に記載の方法。 - 第2構成繰り返し単位の一又は複数のエチレン性不飽和カチオン性モノマーが、ジアリルジメチルアンモニウムナイトレート、四級化ジメチルアミノエチル(メタ)アクリレートナイトレート、四級化ビニルイミダゾールナイトレートからなる群から選択される、請求項3に記載の方法。
- コポリマーが、1000質量部のコポリマーに基づき、80以上で100未満の質量部のビニルピロリドン、及び0より大きく20以下の質量部のジアリルジメチルアンモニウムナイトレートを含むモノマー混合物の遊離ラジカル重合により作製されるランダムコポリマーである、請求項4に記載の方法。
- 少なくとも一の銀化合物が硝酸銀を含み、少なくとも一のポリオールがエチレングリコールを含み、反応混合物に添加される硝酸銀の総量が、反応混合物1リットル当たり1.5×10−2モル〜1モルであり、且つ反応が、反応混合物の質量に基づいて、0.1質量%〜20質量%のコポリマーの存在下で実施される、請求項1に記載の方法。
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BR112015006873A2 (pt) | 2017-07-04 |
US20170066058A1 (en) | 2017-03-09 |
JP2017063036A (ja) | 2017-03-30 |
WO2014052887A2 (en) | 2014-04-03 |
CN104797363B (zh) | 2018-09-07 |
EP2900409B1 (en) | 2019-05-22 |
CN104797363A (zh) | 2015-07-22 |
AU2013323179A1 (en) | 2015-04-09 |
JP6352358B2 (ja) | 2018-07-04 |
KR20150082220A (ko) | 2015-07-15 |
US20140178246A1 (en) | 2014-06-26 |
KR102172116B1 (ko) | 2020-10-30 |
CA2886404A1 (en) | 2014-04-03 |
US20140178247A1 (en) | 2014-06-26 |
US20160303658A1 (en) | 2016-10-20 |
EP2900409A4 (en) | 2016-05-25 |
WO2014052887A3 (en) | 2014-06-26 |
JP2016500897A (ja) | 2016-01-14 |
US9410007B2 (en) | 2016-08-09 |
EP2900409A2 (en) | 2015-08-05 |
AU2013323179B2 (en) | 2018-02-15 |
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