JP6546851B2 - Pcp複合体 - Google Patents
Pcp複合体 Download PDFInfo
- Publication number
- JP6546851B2 JP6546851B2 JP2015528345A JP2015528345A JP6546851B2 JP 6546851 B2 JP6546851 B2 JP 6546851B2 JP 2015528345 A JP2015528345 A JP 2015528345A JP 2015528345 A JP2015528345 A JP 2015528345A JP 6546851 B2 JP6546851 B2 JP 6546851B2
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- JP
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- Prior art keywords
- polymer
- acid
- group
- pcp
- metal ion
- Prior art date
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- 229920000642 polymer Polymers 0.000 claims description 112
- 239000013259 porous coordination polymer Substances 0.000 claims description 71
- 125000000524 functional group Chemical group 0.000 claims description 41
- 229910021645 metal ion Inorganic materials 0.000 claims description 32
- 239000002131 composite material Substances 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 15
- 238000000926 separation method Methods 0.000 claims description 13
- 230000009477 glass transition Effects 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000013110 organic ligand Substances 0.000 claims description 10
- 238000000465 moulding Methods 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000000314 lubricant Substances 0.000 claims description 5
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims description 4
- 239000006258 conductive agent Substances 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
- 101710178035 Chorismate synthase 2 Proteins 0.000 claims description 2
- 101710152694 Cysteine synthase 2 Proteins 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 239000011232 storage material Substances 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- -1 polycyclic compound Chemical class 0.000 description 99
- 238000001179 sorption measurement Methods 0.000 description 34
- 239000002253 acid Substances 0.000 description 22
- 239000007789 gas Substances 0.000 description 22
- 239000010949 copper Substances 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 16
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 238000003795 desorption Methods 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 239000003431 cross linking reagent Substances 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 239000011701 zinc Substances 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000001294 propane Substances 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003463 adsorbent Substances 0.000 description 6
- 150000007824 aliphatic compounds Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 150000001334 alicyclic compounds Chemical class 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 5
- 150000002390 heteroarenes Chemical class 0.000 description 5
- 150000002391 heterocyclic compounds Chemical class 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OYFRNYNHAZOYNF-UHFFFAOYSA-N H2dhybdc Natural products OC(=O)C1=CC(O)=C(C(O)=O)C=C1O OYFRNYNHAZOYNF-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical compound C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012973 diazabicyclooctane Substances 0.000 description 3
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FUPIVZHYVSCYLX-UHFFFAOYSA-N 1,4-dihydronaphthalene Chemical compound C1=CC=C2CC=CCC2=C1 FUPIVZHYVSCYLX-UHFFFAOYSA-N 0.000 description 2
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- ZEVWQFWTGHFIDH-UHFFFAOYSA-N 1h-imidazole-4,5-dicarboxylic acid Chemical compound OC(=O)C=1N=CNC=1C(O)=O ZEVWQFWTGHFIDH-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 2
- QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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Images
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Description
より優れた吸着性能を与える吸着材として、外部刺激により動的構造変化を生じるPCPが開発されている。この新規な動的構造変化高分子金属錯体をガス状の物質の吸着材として使用した場合、ある一定の圧力までは物質を吸着しないが、ある一定圧を越えると物質の吸着が始まるという現象が観測されている。また、物質の種類によって吸着開始圧が異なる現象が観測されている。
項1. 金属イオンと有機配位子から構成される多孔性配位高分子(PCP)とガラス転移点(Tg)が70℃以下のポリマーを含み、ポリマーは前記金属イオンと配位可能な複数の官能基を有し、PCPとポリマーが前記官能基を介して架橋されてなる、複合体。
項2. 架橋間分子量が300〜1300である項1に記載の複合体。
項3. 前記官能基がグリシジル基、COOH、無水カルボン酸基(−CO-O-CO-R)、CS2H、OH、SH、SO、SO2、SO3H、NO2、-S-、-SS-、Si(OH)3、Ge(OH)3、Sn(OH)3、Si(SH)4、Ge(SH)4、Sn(SH)4、PO3H、AsO3H、AsO4H、P(SH)3、As(SH)3、CH(SH)2、C(SH)3、CH(NH2)2、C(NH2)3、CH(OH)2、C(OH)3、CH(CN)2、C(CN)3、CH(RSH)2、C(RSH)3、CH(RNH2)2、C(RNH2)3、CH(ROH)2、C(ROH)3、CH(RCN)2、C(RCN)3、1級,2級又は3級アミノ基、芳香環を構成する窒素原子(式中、RはC1〜C5アルキル基又はアリール基を示す)からなる群から選ばれる少なくとも1種である、項1〜2のいずれかに記載の複合体。
項4. 前記官能基は、ポリマーの繰り返し単位100個あたり1〜30個である、項1〜3のいずれかに記載の複合体。
項5. 金属イオンがMg2+、Ca2+、Sr2+、Ba2+、Sc3+、Y3+、Ti4+、Zr4+、Hf4+、V4+、V3+、V2+、Nb3+、Ta3+、Cr3+、Mo3+、W3+、Mn3+、Mn2+、Re3+、Re2+、Fe3+、Fe2+、Ru3+、Ru2+、Os3+、Os2+、Co3+、Co2+、Rh2+、Rh+、Ir2+、Ir+、Ni2+、Ni+、Pd2+、Pd+、Pt2+、Pt+、Cu2+、Cu+、Ag+、Au+、Zn2+、Cd2+、Hg2+、Al3+、Ga3+、In3+、Tl3+、Si4+、Si2+、Ge4+、Ge2+、Sn4+、Sn2+、Pb4+、Pb2+、As5+、As3+、As+、Sb5+、Sb3+、Sb+、Bi5+、Bi3+及びBi+からなる群から選ばれる、項1〜4のいずれかに記載の複合体。
項6. PCP70〜99重量%、ポリマー1〜30重量%を含む、項1〜5のいずれかに記載の複合体。
項7. 項1〜8のいずれかに記載の複合体を成形してなる成形体。
項8. 前記複合体と滑剤及び導電剤からなる群から選ばれる少なくとも1種を含む、項7に記載の成形体。
項9. 前記成形体が、薄膜状、粒状、ペレット状の形状を有する、項7又は8に記載の成形体。
項10. 項7〜9のいずれかに記載の成形体を含む物質の貯蔵材料。
項11. 項7〜9のいずれかに記載の成形体を含む物質の分離材料。
項12. 金属イオンと有機配位子から構成される多孔性配位高分子(PCP)とガラス転移点が70℃以下のポリマーを溶媒中で混合してPCPとポリマーを前記官能基を介して架橋させることを特徴とする、項1〜6のいずれかに記載の複合体の製造方法。
有機配位子の金属イオンに配位可能な前記官能基は、1つの芳香族化合物、脂肪族化合物、脂環式化合物、ヘテロ芳香族化合物、ヘテロ環式化合物に対し1〜5個、好ましくは2〜4個、より好ましくは2〜3個含まれる。このような金属イオンに配位可能な官能基としては、グリシジル基、COOH、無水カルボン酸基、CS2H、OH、SH、SO、SO2、SO3H、NO2、-S-、-SS-、Si(OH)3、Ge(OH)3、Sn(OH)3、Si(SH)4、Ge(SH)4、Sn(SH)4、PO3H、AsO3H、AsO4H、P(SH)3、As(SH)3、CH(SH)2、C(SH)3、CH(NH2)2、C(NH2)3、CH(OH)2、C(OH)3、CH(CN)2、C(CN)3、CH(RSH)2、C(RSH)3、CH(RNH2)2、C(RNH2)3、CH(ROH)2、C(ROH)3、CH(RCN)2、C(RCN)3、NH2、NHR、NR2、芳香環を構成する窒素原子、(式中、RはC1〜C5アルキル基又はアリール基を示す)が挙げられる。芳香環を構成する窒素原子とは、ピリジン、ピリミジン、ピリダジン、ピラジン、トリアジン、イミダゾール、チアゾール、オキサゾール、フェナントロリン、キノリン、イソキノリン、ナフチリジン、プリン、ビピリジン、テルピリジンなどの環内窒素原子を意味する。
ポリマーが有する「複数の官能基」は、架橋点が複数になるように複数の官能基を有することを意味し、1種類の官能基が複数存在してもよく、複数種類の官能基が各々少なくとも1個ポリマーに存在してもよい。通常は、金属イオンと配位可能な官能基はポリマーに多数存在し、ポリマーの多数の点でPCPにより架橋される。
脂肪族化合物としては、メタン、エタン、プロパン、ブタン、ペンタン、ヘキサン、ヘプタン、オクタン、ノナン、デカン、ウンデカン、ドデカン等の炭素数1〜12の脂肪族化合物が挙げられる。
ヘテロ芳香族化合物は、N、O及びSから選択される1〜3個のヘテロ原子を含む、5又は6員の芳香環からなる単環又は多環系の化合物を意味し、多環系の場合には少なくとも1つの環がヘテロ芳香環であればよい。具体例としては、フラン、チオフェン、ピロール、イミダゾール、ピラゾール、オキサゾール、チアゾール、イソオキサゾール、イソチアゾール、ピリジン、ピラジン、ピリダジン、ピリミジン、ピリダジン、インドール、キノリン、イソキノリン、ベンゾ[b]チオフェン及びベンズイミダゾールが挙げられる。
ヘテロ環式化合物としては、モルホリン、ピロリジン、ピペリジン、メチルピペラジン、テトラヒドトフラン、ジオキサンが挙げられる。
Xで表されるPCPの金属イオンと配位可能な官能基としては、具体的にはCOOH、SO3H、PO3H又はこれらのアルカリ金属塩、ピリジル、ピリミジル、ピリダジル、ピラジル、イミダゾリル、オキサゾリル、イソオキサゾリル、チアゾリル、イソチアゾリル、トリアゾリル、テトラゾリルなどの含窒素アリール基、アミノフェニル、カルボキシフェニルなどが挙げられる。
IRMOF-1, [Zn4O(1,4-BDC)3]n (H2-1,4-BDC= 1,4-benzenedicarboxylic acid)
MOF-69C, [Zn3(OH2)(1,4-BDC)2]n
MOF-74, [M2(DOBDC)]n (H2DOBDC=2,5-dihydroxyterephthalic acid, M=Zn, Co, Ni, Mg)
HKUST-1, [Cu3(1,3,5-BTC)2]n (H3-1,3,5-BTC=1,3,5-benzenetricarboxylic acid)
MOF-508, [Zn(1,4-BDC)(bpy)0.5]n (bpy = 4,4′-bipyridine)
Zn-BDC-DABCO, [Zn2(1,4-BDC)2(DABCO)]n, (DABCO=1,4-diazabicyclo[2.2.2]-octane)
Cr-MIL-101, [Cr3F(H2O)2O(1,4-BDC)3]n
Al-MIL-110, [Al8(OH)12{(OH)3(H2O)3}(1,3-5-BTC)3]n
Al-MIL-53, [Al(OH)(1,4-BDC)]n
ZIF-8, [Zn(MeIM)2]n, (H-MeIM=2-methylimidazole)
MIL-88B, [Cr3OF(1,4-BDC)3]n
MIL-88C, [Fe3OX(O2C-C10H6-CO2)3]n (X = OH, Cl)
MIL-88D, [Cr3OF(O2C-C12H8-CO2)3]n
CID-1 [Zn2(ip)2(bpy)2]n (H2ip=isophthalic acid)
側鎖にカルボン酸残基を有するシリコーン(Shin−Etsu X−22−3701−E、官能基数が繰り返し単位あたり2個、Tg-123℃、一般式(II)でWがCOOH)55mgを脱水した2−ブタノン2.0mLに溶解後、PCP、[Cu(BF4)2(bpp)2]n220mgを分散させた。10分間撹拌したのち298K、5Paで3時間乾燥させ、得られた粉末のうち200mgをペレット成形器に詰めた。25Kgf/cm3で一度加圧した後、10分間放置してから取り出し、373K、5Paで4時間乾燥させ、ペレット状の成形体を得た。
大気下、メタクリル酸グリシジル2.84g及びメタクリル酸ブチル11.3gを脱水酢酸エチル70mLに溶解させ、2,2'-アゾビス(イソ酪酸メチル)461mgの脱水酢酸エチル溶液80mLを加えた。続いて、この溶液を室温で撹拌しながら脱気と窒素ガス置換を繰り返し行った後、窒素ガスの雰囲気下、室温で1時間撹拌した。その後溶液を343Kで4時間加熱し、さらに363Kで16時間加熱した。次にこの反応液を室温まで冷却し、ヘキサン800mLの入った容器に滴下した。続いて溶媒をデカンテーションによって除去した後、生成物を脱水アセトン60mLに溶解させた。この溶液をさらにヘキサン900mLの入った容器に滴下し、デカンテーションによって溶媒を除去した後、脱水アセトン60mLに溶解させた。得られた溶液について313Kで減圧留去を行い、さらに298K、5Paで4時間乾燥し、10.3g(収率72%)を得た。ポリマーAのTgは28℃で、メタクリル酸グリシジルの含量は、繰り返し単位100個あたり約23個であった。
大気下、メタクリル酸1.72g及びメタクリル酸ブチル11.3gを脱水酢酸エチル70mLに溶解させ、2,2'-アゾビス(イソ酪酸メチル)461mgの脱水酢酸エチル溶液80mLを加えた。続いて、この溶液を室温で撹拌しながら脱気と窒素ガス置換を繰り返し行った後、窒素ガスの雰囲気下、室温で1時間撹拌した。その後溶液を353Kで4時間加熱し、さらに363Kで16時間加熱した。次にこの反応液を室温まで冷却し、ヘキサン1800mLの入った容器に滴下した。析出した固体を吸引濾過により回収し、酢酸エチル85mLに溶解させ、さらにヘキサン900mLの入った容器に滴下した。析出した固体を吸引濾過により回収した後ヘキサンで洗浄し、298K、5Paで4時間乾燥し、6.83g(収率52%)を得た。ポリマーBのTgは37℃で、メタクリル酸の含量は、繰り返し単位100個あたり約21個であった。
大気下、ポリマー55mgを脱水2−ブタノン0.5mLに溶解させ、これを溶液Aとした。続いてPCP220mgを脱水2−ブタノン1.5mL中に分散させ、溶液Aを滴下した後10分間撹拌した。続いて298K、5Paで3時間乾燥させ、得られた粉末を乳鉢ですりつぶし、このうち200mgをペレット成形器に詰めた。25Kgf/cm3で一度加圧した後、10分間放置してから取り出し、ペレット状の成形体を得た。
1.ポリマーAとPCP[Cu(BF4)2(bpp)2]nとの複合体(架橋間分子量は450)
2.ポリマーBとPCP[Al(OH)(1,4-bdc)]n (MIL-53) との複合体(架橋間分子量は500)
実施例4の方法で、ポリマーの含有量を変えてペレット状の成形体を作製した。ポリマーの含有量が10重量%でも20重量%でも、気体を300回吸脱着しても成形体の形状が保たれていた。
2.ポリマーの含有量が10重量%のPCP[Cu(BF4)2(bpp)2]nとポリマーAとの複合体
実施例4の方法で、ポリマーの含有量を20重量%とし、ポリマーのTgが異なるポリマーとPCPとの複合体でペレット状の成形体を作製した。気体を300回吸脱着した後の成形体の形状は、Tgが28℃のポリマーでは維持されたが、Tgが75℃のポリマーでは維持されず崩壊した。
1.PCP[Cu(BF4)2(bpp)2]nとTgが28℃のポリマーAとの複合体
2.PCP[Cu(BF4)2(bpp)2]nとTgが75℃の tert-butyl acrylate-co-ethyl acrylate-co-methacrylic acidとの複合体
サンプル管に吸着材をつめて真空加熱前処理を行い、前処理後の吸着材の質量を測定する。サンプル管を吸着測定装置にセットする。基準容積バッファVsに吸着ガスを一定圧導入した後、バルブを開閉し吸着材の入ったサンプル管に吸着ガスを298Kで導入する。導入した吸着ガスの圧力は吸着により減少するため、吸着前後の圧力差より吸着量を求める。
298Kにおける二酸化炭素吸脱着測定を行った。100 kPaにおける吸着量は88 cm3(STP) g-1であった。
298Kにおけるプロピレン吸脱着測定を行った。100 kPaにおける吸着量は82 cm3(STP) g-1であった。
298Kにおけるプロパン吸脱着測定を行った。104 kPaにおける吸着量は43 cm3(STP) g-1であった。
分離度は以下の方法で算出した。はじめにガスAとガスBの吸脱着等温線を測定する。得られたデータから、次式によって定義される分離度Sを求める。
S = (XA/XB)/(YA/YB)
ポリマーの含有量が20重量%の[Cu(BF4)2(bpp)2]nとポリマーAとの複合体によるプロパン、プロピレンの分離の結果を図9に示す。
ポリマーの含有量が20重量%の[Cu(BF4)2(bpp)2]nとTgが163℃、架橋間分子量が0、ポリマーの繰り返し単位100個あたりの官能基が100個であるポリビニルイミダゾールをポリマーとの複合体を、実施例4の方法でペレット状の成形体を作製した。実施例6の方法でプロピレンの吸着試験を行ったが、プロピレンを全く吸着しなかった。
Claims (11)
- 金属イオンと有機配位子から構成される多孔性配位高分子(PCP)とガラス転移点(Tg)が70℃以下のポリマーを含み、ポリマーは前記金属イオンと配位可能な複数の官能基を有し、前記官能基が前記金属イオンの少なくとも一部に配位することによりPCPとポリマーが架橋を形成しており、
前記金属イオンがMg 2+ 、Ca 2+ 、Sr 2+ 、Ba 2+ 、Sc 3+ 、Y 3+ 、Ti 4+ 、Zr 4+ 、Hf 4+ 、V 4+ 、V 3+ 、V 2+ 、Nb 3+ 、Ta 3+ 、Cr 3+ 、Mo 3+ 、W 3+ 、Mn 3+ 、Mn 2+ 、Re 3+ 、Re 2+ 、Fe 3+ 、Fe 2+ 、Ru 3+ 、Ru 2+ 、Os 3+ 、Os 2+ 、Co 3+ 、Co 2+ 、Rh 2+ 、Ir 2+ 、Ni 2+ 、Pd 2+ 、Pt 2+ 、Cu 2+ 、Zn 2+ 、Cd 2+ 、Hg 2+ 、Al 3+ 、Ga 3+ 、In 3+ 、Tl 3+ 、Si 4+ 、Si 2+ 、Ge 4+ 、Ge 2+ 、Sn 4+ 、Sn 2+ 、Pb 4+ 、Pb 2+ 、As 5+ 、As 3+ 、Sb 5+ 、Sb 3+ 、Bi 5+ 及びBi 3+ からなる群から選ばれ、
前記官能基は、ポリマーの繰り返し単位100個あたり1〜30個である、複合体。 - 架橋間分子量が300〜1300である請求項1に記載の複合体。
- 前記官能基がグリシジル基、COOH、無水カルボン酸基(−CO-O-CO-R)、CS2H、OH、SH、SO、SO2、SO3H、NO2、-S-、-SS-、Si(OH)3、Ge(OH)3、Sn(OH)3、Si(SH)4、Ge(SH)4、Sn(SH)4、PO3H、AsO3H、AsO4H、P(SH)3、As(SH)3、CH(SH)2、C(SH)3、CH(NH2)2、C(NH2)3、CH(OH)2、C(OH)3、CH(CN)2、C(CN)3、CH(RSH)2、C(RSH)3、CH(RNH2)2、C(RNH2)3、CH(ROH)2、C(ROH)3、CH(RCN)2、C(RCN)3、1級,2級又は3級アミノ基、芳香環を構成する窒素原子(式中、RはC1〜C5アルキル基又はアリール基を示す)からなる群から選ばれる少なくとも1種である、請求項1〜2のいずれかに記載の複合体。
- 前記多孔性配位高分子(PCP)において、細孔に少なくとも1つの物質を吸着するのに適しているポリマーを含有するものを除く、請求項1〜3のいずれか1項に記載の複合体。
- PCP70〜99重量%、ポリマー1〜30重量%を含む、請求項1〜4のいずれかに記載の複合体。
- 請求項1〜5のいずれかに記載の複合体を成形してなる成形体。
- 前記複合体と滑剤及び導電剤からなる群から選ばれる少なくとも1種を含む、請求項6に記載の成形体。
- 前記成形体が、薄膜状、粒状、ペレット状の形状を有する、請求項6又は7に記載の成形体。
- 請求項6〜8のいずれかに記載の成形体を含む物質の貯蔵材料。
- 請求項6〜8のいずれかに記載の成形体を含む物質の分離材料。
- 金属イオンと有機配位子から構成される多孔性配位高分子(PCP)と前記金属イオンと配位可能な複数の官能基を有するガラス転移点が70℃以下のポリマーを溶媒中で混合して、前記官能基が前記金属イオンの少なくとも一部に配位させることによりPCPとポリマーとを架橋させる工程を含み、
前記金属イオンがMg 2+ 、Ca 2+ 、Sr 2+ 、Ba 2+ 、Sc 3+ 、Y 3+ 、Ti 4+ 、Zr 4+ 、Hf 4+ 、V 4+ 、V 3+ 、V 2+ 、Nb 3+ 、Ta 3+ 、Cr 3+ 、Mo 3+ 、W 3+ 、Mn 3+ 、Mn 2+ 、Re 3+ 、Re 2+ 、Fe 3+ 、Fe 2+ 、Ru 3+ 、Ru 2+ 、Os 3+ 、Os 2+ 、Co 3+ 、Co 2+ 、Rh 2+ 、Ir 2+ 、Ni 2+ 、Pd 2+ 、Pt 2+ 、Cu 2+ 、Zn 2+ 、Cd 2+ 、Hg 2+ 、Al 3+ 、Ga 3+ 、In 3+ 、Tl 3+ 、Si 4+ 、Si 2+ 、Ge 4+ 、Ge 2+ 、Sn 4+ 、Sn 2+ 、Pb 4+ 、Pb 2+ 、As 5+ 、As 3+ 、Sb 5+ 、Sb 3+ 、Bi 5+ 及びBi 3+ からなる群から選ばれ、
前記官能基は、ポリマーの繰り返し単位100個あたり1〜30個である、請求項1〜5のいずれかに記載の複合体の製造方法。
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