KR20170085550A - 포름알데하이드를 포획하기 위한 중합체 재료 - Google Patents
포름알데하이드를 포획하기 위한 중합체 재료 Download PDFInfo
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- KR20170085550A KR20170085550A KR1020177016104A KR20177016104A KR20170085550A KR 20170085550 A KR20170085550 A KR 20170085550A KR 1020177016104 A KR1020177016104 A KR 1020177016104A KR 20177016104 A KR20177016104 A KR 20177016104A KR 20170085550 A KR20170085550 A KR 20170085550A
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- South Korea
- Prior art keywords
- group
- formula
- alkyl
- sorbent
- hydrogen
- Prior art date
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 285
- 239000000463 material Substances 0.000 title claims abstract description 109
- 239000000178 monomer Substances 0.000 claims abstract description 139
- 239000002861 polymer material Substances 0.000 claims abstract description 124
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 123
- 239000001257 hydrogen Substances 0.000 claims abstract description 123
- 239000002594 sorbent Substances 0.000 claims abstract description 115
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 109
- 239000000203 mixture Substances 0.000 claims abstract description 80
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 75
- 125000003118 aryl group Chemical group 0.000 claims abstract description 75
- 238000000034 method Methods 0.000 claims abstract description 57
- 239000002243 precursor Substances 0.000 claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 40
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 160
- 229910052799 carbon Inorganic materials 0.000 claims description 50
- 150000002431 hydrogen Chemical class 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 229920006216 polyvinyl aromatic Polymers 0.000 claims description 40
- 150000001721 carbon Chemical group 0.000 claims description 37
- 238000001179 sorption measurement Methods 0.000 claims description 35
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 32
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 25
- 229920002554 vinyl polymer Polymers 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 15
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 abstract description 4
- 125000003003 spiro group Chemical group 0.000 abstract description 2
- 239000007787 solid Substances 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- 239000011148 porous material Substances 0.000 description 17
- 238000003828 vacuum filtration Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 239000007789 gas Substances 0.000 description 14
- 239000003999 initiator Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- -1 for example Substances 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 150000003254 radicals Chemical group 0.000 description 12
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 238000003775 Density Functional Theory Methods 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000002837 carbocyclic group Chemical group 0.000 description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 150000003460 sulfonic acids Chemical class 0.000 description 6
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000004342 Benzoyl peroxide Substances 0.000 description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229920002866 paraformaldehyde Polymers 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000004576 sand Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000004566 building material Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 210000000707 wrist Anatomy 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000003570 air Substances 0.000 description 3
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002429 nitrogen sorption measurement Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 2
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000006619 Stille reaction Methods 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002156 adsorbate Substances 0.000 description 2
- 239000000809 air pollutant Substances 0.000 description 2
- 231100001243 air pollutant Toxicity 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229920000831 ionic polymer Polymers 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- 125000005409 triarylsulfonium group Chemical group 0.000 description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- UOKJATVTNIIQPV-UHFFFAOYSA-M 4-ethoxycarbonylbenzenesulfinate;tetrabutylazanium Chemical compound CCOC(=O)C1=CC=C(S([O-])=O)C=C1.CCCC[N+](CCCC)(CCCC)CCCC UOKJATVTNIIQPV-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QYPPJABKJHAVHS-UHFFFAOYSA-N Agmatine Natural products NCCCCNC(N)=N QYPPJABKJHAVHS-UHFFFAOYSA-N 0.000 description 1
- 229910017008 AsF 6 Inorganic materials 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- ICVXZUKBGODFJF-UHFFFAOYSA-N CC=1C(=C(C=CC1)S(=O)O)CC Chemical compound CC=1C(=C(C=CC1)S(=O)O)CC ICVXZUKBGODFJF-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- AVTLBBWTUPQRAY-BUHFOSPRSA-N V-59 Substances CCC(C)(C#N)\N=N\C(C)(CC)C#N AVTLBBWTUPQRAY-BUHFOSPRSA-N 0.000 description 1
- 239000007877 V-601 Substances 0.000 description 1
- WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- QYPPJABKJHAVHS-UHFFFAOYSA-P agmatinium(2+) Chemical compound NC(=[NH2+])NCCCC[NH3+] QYPPJABKJHAVHS-UHFFFAOYSA-P 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001601 aromatic carbocyclic compounds Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002551 biofuel Substances 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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Landscapes
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- Engineering & Computer Science (AREA)
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- Environmental & Geological Engineering (AREA)
- Biomedical Technology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
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| US201462080817P | 2014-11-17 | 2014-11-17 | |
| US62/080,817 | 2014-11-17 | ||
| PCT/US2015/059909 WO2016081226A1 (en) | 2014-11-17 | 2015-11-10 | Polymeric materials for capturing formaldehyde |
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| KR20170085550A true KR20170085550A (ko) | 2017-07-24 |
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| EP3310475B1 (en) | 2015-06-19 | 2019-03-27 | 3M Innovative Properties Company | Divinylbenzene/maleic anhydride polymeric sorbents for carbon dioxide |
| CN107708856B (zh) | 2015-06-19 | 2020-07-03 | 3M创新有限公司 | 用于二氧化碳的水解二乙烯基苯/马来酸酐聚合物吸附剂 |
| CN108367270B (zh) | 2015-12-18 | 2021-07-09 | 3M创新有限公司 | 用于二氧化碳的聚合物吸附剂 |
| KR20180095857A (ko) | 2015-12-18 | 2018-08-28 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 알데하이드용 폴리머 수착제 |
| WO2017106438A1 (en) | 2015-12-18 | 2017-06-22 | 3M Innovative Properties Company | Polymeric sorbents for reactive gases |
| CN108778488B (zh) | 2016-03-14 | 2022-02-18 | 3M创新有限公司 | 包括用于反应性气体的聚合物吸附剂的复合颗粒 |
| EP3429725B1 (en) | 2016-03-14 | 2021-07-07 | 3M Innovative Properties Company | Air filters comprising polymeric sorbents for reactive gases |
| US10960341B2 (en) | 2016-03-14 | 2021-03-30 | 3M Innovative Properties Company | Air filters comprising polymeric sorbents for aldehydes |
| TWI795411B (zh) | 2017-06-16 | 2023-03-11 | 美商3M新設資產公司 | 用於醛之聚合性吸著劑 |
| WO2018229604A2 (en) | 2017-06-16 | 2018-12-20 | 3M Innovative Properties Company | Air filters comprising polymeric sorbents for aldehydes |
| DE102018114351A1 (de) * | 2017-06-30 | 2019-01-03 | Mann+Hummel Gmbh | Filtermedium |
| WO2019110557A1 (en) * | 2017-12-04 | 2019-06-13 | Stichting Voor De Technische Wetenschappen | Macromolecular compositions comprising indene-derivatives, preparation thereof, and use thereof |
| CN110156930A (zh) * | 2019-04-30 | 2019-08-23 | 昆明理工大学 | 一种化学吸附降解甲醛的水性丙烯酸树脂及其制备方法 |
| WO2021038347A1 (en) * | 2019-08-30 | 2021-03-04 | 3M Innovative Properties Company | Polymeric sorbents for aldehydes and methods of making |
| CN114307986B (zh) * | 2021-12-28 | 2023-05-12 | 南昌航空大学 | 一种钯离子吸附剂的制备方法 |
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| GB800639A (en) | 1955-07-08 | 1958-08-27 | Wolfgang Muhlberg | Manufacture of cation exchangers of the polystyrene-type |
| CN1062541A (zh) | 1992-01-24 | 1992-07-08 | 中国林业科学院林产化学工业研究所 | Au甲醛捕捉剂生产工艺 |
| JP3953638B2 (ja) * | 1997-09-11 | 2007-08-08 | 日本合成化学工業株式会社 | アルデヒド吸着剤 |
| CN1548164A (zh) | 2003-05-22 | 2004-11-24 | 王永利 | 甲醛吸收剂及其制备方法 |
| CN1301780C (zh) | 2004-04-30 | 2007-02-28 | 罗文圣 | 一种有害气体捕捉材料及其制备方法 |
| CN103173004B (zh) | 2011-12-23 | 2014-12-03 | 万华化学(广东)有限公司 | 具有甲醛反应性的水性聚氨酯分散体组合物及其制备和应用 |
| US9139674B2 (en) | 2012-09-25 | 2015-09-22 | 3M Innovative Properties Company | Rigid and contorted divinyl crosslinkers |
| EP2900625B1 (en) | 2012-09-25 | 2016-10-26 | 3M Innovative Properties Company | Polymerizable spirobisindane monomers and polymers prepared therefrom |
| TWI490232B (zh) | 2012-12-28 | 2015-07-01 | Ind Tech Res Inst | 甲醛捕捉劑及其製備方法 |
| WO2014186095A1 (en) | 2013-05-14 | 2014-11-20 | 3M Innovative Properties Company | Amino-containing polymeric material with rigid and contorted divinyl crosslinker |
| CN105229055B (zh) | 2013-05-14 | 2017-04-26 | 3M创新有限公司 | 基于可自由基聚合的螺双茚单体的含磺酰基聚合物 |
| CN106660039B (zh) | 2014-06-13 | 2020-10-27 | 3M创新有限公司 | 含磺酸聚合物材料作为胺吸附剂 |
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| JP2018501086A (ja) | 2018-01-18 |
| TW201627066A (zh) | 2016-08-01 |
| CN107108783B (zh) | 2019-08-30 |
| TWI647009B (zh) | 2019-01-11 |
| US10391471B2 (en) | 2019-08-27 |
| CN107108783A (zh) | 2017-08-29 |
| JP6567052B2 (ja) | 2019-08-28 |
| WO2016081226A1 (en) | 2016-05-26 |
| EP3221367A1 (en) | 2017-09-27 |
| US20170333870A1 (en) | 2017-11-23 |
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