JP6925339B2 - アルデヒド用ポリマー吸着剤 - Google Patents
アルデヒド用ポリマー吸着剤 Download PDFInfo
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- JP6925339B2 JP6925339B2 JP2018531451A JP2018531451A JP6925339B2 JP 6925339 B2 JP6925339 B2 JP 6925339B2 JP 2018531451 A JP2018531451 A JP 2018531451A JP 2018531451 A JP2018531451 A JP 2018531451A JP 6925339 B2 JP6925339 B2 JP 6925339B2
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- nitrogen
- polymer adsorbent
- alkyl
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- 239000003463 adsorbent Substances 0.000 title claims description 230
- 229920000642 polymer Polymers 0.000 title claims description 177
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims 10
- 239000000178 monomer Substances 0.000 claims description 182
- 239000000203 mixture Substances 0.000 claims description 151
- 239000002861 polymer material Substances 0.000 claims description 135
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 131
- 239000002243 precursor Substances 0.000 claims description 119
- -1 nitrogen-containing compound Chemical class 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 81
- 239000001257 hydrogen Substances 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 75
- 238000000034 method Methods 0.000 claims description 70
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 54
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 40
- 238000001179 sorption measurement Methods 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 36
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 33
- 125000002947 alkylene group Chemical group 0.000 claims description 33
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 19
- 125000000732 arylene group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 10
- 150000003440 styrenes Chemical class 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 162
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 128
- 239000007787 solid Substances 0.000 description 100
- 125000004432 carbon atom Chemical group C* 0.000 description 97
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- 150000001299 aldehydes Chemical class 0.000 description 80
- 238000012360 testing method Methods 0.000 description 48
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 46
- 235000019439 ethyl acetate Nutrition 0.000 description 44
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- 238000003828 vacuum filtration Methods 0.000 description 35
- 229920001002 functional polymer Polymers 0.000 description 32
- 239000007789 gas Substances 0.000 description 32
- 239000011148 porous material Substances 0.000 description 31
- 239000000463 material Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- 229910052786 argon Inorganic materials 0.000 description 23
- 239000000523 sample Substances 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 239000003960 organic solvent Substances 0.000 description 22
- 239000000975 dye Substances 0.000 description 17
- 239000003999 initiator Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 239000004576 sand Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 10
- 150000008064 anhydrides Chemical class 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 239000004342 Benzoyl peroxide Substances 0.000 description 9
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 9
- 235000019400 benzoyl peroxide Nutrition 0.000 description 9
- 101150009274 nhr-1 gene Proteins 0.000 description 9
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 238000003775 Density Functional Theory Methods 0.000 description 5
- 125000005263 alkylenediamine group Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- MRDOFVRMTNWMDA-UHFFFAOYSA-N 2-bromo-4-[3-(3-bromo-4-hydroxy-2,5-dimethylphenyl)-1,1-dioxo-2,1$l^{6}-benzoxathiol-3-yl]-3,6-dimethylphenol Chemical compound BrC1=C(O)C(C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C(=C(Br)C(O)=C(C)C=2)C)=C1C MRDOFVRMTNWMDA-UHFFFAOYSA-N 0.000 description 4
- QYPPJABKJHAVHS-UHFFFAOYSA-N Agmatine Natural products NCCCCNC(N)=N QYPPJABKJHAVHS-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- QYPPJABKJHAVHS-UHFFFAOYSA-P agmatinium(2+) Chemical compound NC(=[NH2+])NCCCC[NH3+] QYPPJABKJHAVHS-UHFFFAOYSA-P 0.000 description 4
- 239000004566 building material Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 description 4
- 229920002866 paraformaldehyde Polymers 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
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 3
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 3
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 3
- MCTQNEBFZMBRSQ-UHFFFAOYSA-N (3-amino-4-phenyldiazenylphenyl)azanium;chloride Chemical compound Cl.NC1=CC(N)=CC=C1N=NC1=CC=CC=C1 MCTQNEBFZMBRSQ-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
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003344 environmental pollutant Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 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
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000010943 off-gassing Methods 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 231100000719 pollutant Toxicity 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000005409 triarylsulfonium group Chemical group 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- UGDSCHVVUPHIFM-UHFFFAOYSA-N 1,1,1-tris(aminomethyl)ethane Chemical compound NCC(C)(CN)CN UGDSCHVVUPHIFM-UHFFFAOYSA-N 0.000 description 1
- UIFVCPMLQXKEEU-UHFFFAOYSA-N 2,3-dimethylbenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1C UIFVCPMLQXKEEU-UHFFFAOYSA-N 0.000 description 1
- GISVICWQYMUPJF-UHFFFAOYSA-N 2,4-Dimethylbenzaldehyde Chemical compound CC1=CC=C(C=O)C(C)=C1 GISVICWQYMUPJF-UHFFFAOYSA-N 0.000 description 1
- SMUVABOERCFKRW-UHFFFAOYSA-N 2,5-Dimethylbenzaldehyde Chemical compound CC1=CC=C(C)C(C=O)=C1 SMUVABOERCFKRW-UHFFFAOYSA-N 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
- 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 1
- JCYPECIVGRXBMO-UHFFFAOYSA-N 4-(dimethylamino)azobenzene Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=CC=CC=C1 JCYPECIVGRXBMO-UHFFFAOYSA-N 0.000 description 1
- ZPLCXHWYPWVJDL-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)methyl]-1,3-oxazolidin-2-one Chemical compound C1=CC(O)=CC=C1CC1NC(=O)OC1 ZPLCXHWYPWVJDL-UHFFFAOYSA-N 0.000 description 1
- OLQIKGSZDTXODA-UHFFFAOYSA-N 4-[3-(4-hydroxy-2-methylphenyl)-1,1-dioxo-2,1$l^{6}-benzoxathiol-3-yl]-3-methylphenol Chemical compound CC1=CC(O)=CC=C1C1(C=2C(=CC(O)=CC=2)C)C2=CC=CC=C2S(=O)(=O)O1 OLQIKGSZDTXODA-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
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 229910017008 AsF 6 Inorganic materials 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- FRPHFZCDPYBUAU-UHFFFAOYSA-N Bromocresolgreen Chemical compound CC1=C(Br)C(O)=C(Br)C=C1C1(C=2C(=C(Br)C(O)=C(Br)C=2)C)C2=CC=CC=C2S(=O)(=O)O1 FRPHFZCDPYBUAU-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- MCTQNEBFZMBRSQ-GEEYTBSJSA-N Chrysoidine Chemical compound Cl.NC1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 MCTQNEBFZMBRSQ-GEEYTBSJSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
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- B01D2258/02—Other waste gases
- B01D2258/0283—Flue gases
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2258/00—Sources of waste gases
- B01D2258/02—Other waste gases
- B01D2258/0283—Flue gases
- B01D2258/0291—Flue gases from waste incineration plants
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2258/00—Sources of waste gases
- B01D2258/06—Polluted air
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/49—Materials comprising an indicator, e.g. colour indicator, pH-indicator
-
- 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
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
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| US201562269613P | 2015-12-18 | 2015-12-18 | |
| US62/269,613 | 2015-12-18 | ||
| PCT/US2016/066818 WO2017106434A1 (en) | 2015-12-18 | 2016-12-15 | Polymeric sorbents for aldehydes |
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| US10400050B2 (en) * | 2015-05-20 | 2019-09-03 | 3M Innovative Properties Company | Metal-containing polymeric materials |
| WO2016205444A1 (en) | 2015-06-19 | 2016-12-22 | 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 |
| US11179698B2 (en) | 2015-12-18 | 2021-11-23 | 3M Innovative Properties Company | Polymeric sorbents for carbon dioxide |
| KR20180095856A (ko) * | 2015-12-18 | 2018-08-28 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 반응성 기체용 폴리머 수착제 |
| US10960341B2 (en) | 2016-03-14 | 2021-03-30 | 3M Innovative Properties Company | Air filters comprising polymeric sorbents for aldehydes |
| KR102444323B1 (ko) | 2016-03-14 | 2022-09-16 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 알데하이드용 중합체 수착제를 포함하는 복합 과립제 |
| CN108778455B (zh) | 2016-03-14 | 2021-12-14 | 3M创新有限公司 | 包含用于反应性气体的聚合吸附剂的空气过滤器 |
| WO2017161530A1 (en) | 2016-03-24 | 2017-09-28 | 3M Innovative Properties Company | Room air purifier with rfid reader |
| CN109952148B (zh) | 2016-11-14 | 2023-01-20 | 3M创新有限公司 | 包括含金属的聚合物材料的复合颗粒 |
| KR20190077528A (ko) | 2016-11-14 | 2019-07-03 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 금속-함유 중합체 수착제를 포함하는 공기 필터 |
| WO2018090279A1 (en) | 2016-11-17 | 2018-05-24 | 3M Innovative Properties Company | Air filter with visual filter life indicator zone and sorbent-loaded visual reference zone |
| WO2018229604A2 (en) | 2017-06-16 | 2018-12-20 | 3M Innovative Properties Company | Air filters comprising polymeric sorbents for aldehydes |
| KR20200019878A (ko) * | 2017-06-16 | 2020-02-25 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 알데하이드용 중합체 수착제 |
| US11298681B2 (en) | 2018-03-01 | 2022-04-12 | 3M Innovative Properties Company | Urea-impregnated zeolite sorbents and method for making the same |
| CN109337004B (zh) * | 2018-09-28 | 2021-07-02 | 健帆生物科技集团股份有限公司 | 双功能化多级孔吸附树脂及其制备方法 |
| CN113710845A (zh) | 2019-04-25 | 2021-11-26 | 3M创新有限公司 | 声学制品及其方法 |
| CN111729492B (zh) * | 2019-07-19 | 2022-07-15 | 华瑞创新节能环保科技(北京)有限公司 | 一种可变色甲醛清除纸及其制备方法 |
| WO2021038347A1 (en) * | 2019-08-30 | 2021-03-04 | 3M Innovative Properties Company | Polymeric sorbents for aldehydes and methods of making |
| US11951226B2 (en) | 2019-11-25 | 2024-04-09 | 3M Innovative Properties Company | Ethylene oxide sterilization sensor including acid-functional sorbent and method of use |
| JP7672670B2 (ja) * | 2020-05-20 | 2025-05-08 | 矢部川電気工業株式会社 | 気体流路加湿装置、水素ガス分析システム、気体流路加湿方法及び水素ガス分析方法 |
| WO2025125969A1 (en) | 2023-12-15 | 2025-06-19 | 3M Innovative Properties Company | Respiratory protection devices and methods of manufacturing the same |
| WO2025125970A1 (en) | 2023-12-15 | 2025-06-19 | 3M Innovative Properties Company | Respiratory protection devices and methods of manufacturing the same |
| WO2025133782A1 (en) | 2023-12-18 | 2025-06-26 | 3M Innovative Properties Company | Respiratory protection devices and methods of manufacturing the same |
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| JPS5241230B2 (enExample) * | 1971-12-27 | 1977-10-17 | ||
| US3799870A (en) | 1973-03-09 | 1974-03-26 | Mobil Oil Corp | Lead trap |
| US4273751A (en) | 1978-11-09 | 1981-06-16 | Calgon Corporation | Removal of acidica contaminants from gas streams by caustic impregnated activated carbon |
| US4443354A (en) | 1982-03-26 | 1984-04-17 | Minnesota Minning And Manufacturing Company | Sorbent material for reducing formaldehyde emission |
| DE3341712C2 (de) | 1983-11-18 | 1987-03-05 | Drägerwerk AG, 2400 Lübeck | Luftreinigungsmittel zur Verwendung in Luftfiltern |
| US6930219B2 (en) | 1999-09-07 | 2005-08-16 | Abb Lummus Global Inc. | Mesoporous material with active metals |
| ATE321078T1 (de) * | 2002-01-25 | 2006-04-15 | Phenomenex Inc | Oberflächenpfropfmodifizierte harze und deren herstellung |
| DE602005026819D1 (de) | 2004-08-27 | 2011-04-21 | Novo Nordisk As | Funktionelles harz mit hoher beladung |
| US20090060809A1 (en) | 2005-03-30 | 2009-03-05 | Sued-Chemie Catalysts Japan, Inc. | Ammonia Decomposition Catalyst and Process for Decomposition of Ammonia Using the Catalyst |
| US7559981B2 (en) | 2006-07-06 | 2009-07-14 | J.M. Huber Corporation | Air filtration media comprising oxidizing agent-treated metal-doped silicon-based gel and zeolite materials |
| WO2011035195A1 (en) | 2009-09-18 | 2011-03-24 | Nano Terra Inc. | Functional nanofibers and methods of making and using the same |
| US8470074B2 (en) | 2009-12-22 | 2013-06-25 | Exxonmobil Research And Engineering Company | Carbon dioxide sorbents |
| PL2563495T3 (pl) | 2010-04-30 | 2020-05-18 | Peter Eisenberger | Metoda wychwytywania ditlenku węgla |
| US20140186250A1 (en) | 2012-07-19 | 2014-07-03 | The United States Of America | Carbonyl functionalized porous inorganic oxide adsorbents and methods of making and using the same |
| US20160311996A1 (en) * | 2013-12-19 | 2016-10-27 | 3M Innovative Properties Company | Divinylbenzene/maleic anhydride polymeric material |
| KR102307434B1 (ko) | 2013-12-19 | 2021-09-30 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 가수분해된 다이비닐벤젠/말레산 무수물 중합체 재료 |
| JP6567052B2 (ja) | 2014-11-17 | 2019-08-28 | スリーエム イノベイティブ プロパティズ カンパニー | ホルムアルデヒドを捕捉するためのポリマー材料 |
| US10400050B2 (en) | 2015-05-20 | 2019-09-03 | 3M Innovative Properties Company | Metal-containing polymeric materials |
| 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 |
| WO2016205444A1 (en) | 2015-06-19 | 2016-12-22 | 3M Innovative Properties Company | Divinylbenzene/maleic anhydride polymeric sorbents for carbon dioxide |
| US11179698B2 (en) | 2015-12-18 | 2021-11-23 | 3M Innovative Properties Company | Polymeric sorbents for carbon dioxide |
| KR20180095856A (ko) | 2015-12-18 | 2018-08-28 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 반응성 기체용 폴리머 수착제 |
| JP6956103B2 (ja) | 2016-03-14 | 2021-10-27 | スリーエム イノベイティブ プロパティズ カンパニー | アルデヒド用のポリマー収着剤を含むエアフィルタ |
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| TWI743071B (zh) | 2021-10-21 |
| US10780416B2 (en) | 2020-09-22 |
| JP2018537284A (ja) | 2018-12-20 |
| CN108430619B (zh) | 2021-05-04 |
| KR20180095857A (ko) | 2018-08-28 |
| CN108430619A (zh) | 2018-08-21 |
| EP3389851B1 (en) | 2021-12-08 |
| EP3389851A1 (en) | 2018-10-24 |
| WO2017106434A1 (en) | 2017-06-22 |
| TW201735996A (zh) | 2017-10-16 |
| US20180345246A1 (en) | 2018-12-06 |
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