EP2649081A1 - Process for coating support surface with porous metal-organic framework - Google Patents
Process for coating support surface with porous metal-organic frameworkInfo
- Publication number
- EP2649081A1 EP2649081A1 EP11847649.8A EP11847649A EP2649081A1 EP 2649081 A1 EP2649081 A1 EP 2649081A1 EP 11847649 A EP11847649 A EP 11847649A EP 2649081 A1 EP2649081 A1 EP 2649081A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- mmol
- acid
- mof
- dmf
- dicarboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000012621 metal-organic framework Substances 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000000576 coating method Methods 0.000 title claims abstract description 15
- 239000011248 coating agent Substances 0.000 title claims abstract description 14
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 34
- 238000005507 spraying Methods 0.000 claims abstract description 17
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 11
- 239000000243 solution Substances 0.000 claims description 31
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 10
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 9
- 239000006260 foam Substances 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 123
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 41
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000010949 copper Substances 0.000 description 24
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 22
- 229910001868 water Inorganic materials 0.000 description 21
- -1 polyethylene Polymers 0.000 description 19
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 17
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 235000019253 formic acid Nutrition 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- JZKNMIIVCWHHGX-UHFFFAOYSA-N adamantane-1,2,2,3-tetracarboxylic acid Chemical compound C1C(C2)CC3CC1(C(=O)O)C(C(O)=O)(C(O)=O)C2(C(O)=O)C3 JZKNMIIVCWHHGX-UHFFFAOYSA-N 0.000 description 12
- 150000001491 aromatic compounds Chemical class 0.000 description 11
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 150000007824 aliphatic compounds Chemical class 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- XIEPJMXMMWZAAV-UHFFFAOYSA-N cadmium nitrate Inorganic materials [Cd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XIEPJMXMMWZAAV-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 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
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- MTEWCUZXTGXLQX-SPSNFJOYSA-H dialuminum;(e)-but-2-enedioate Chemical compound [Al+3].[Al+3].[O-]C(=O)\C=C\C([O-])=O.[O-]C(=O)\C=C\C([O-])=O.[O-]C(=O)\C=C\C([O-])=O MTEWCUZXTGXLQX-SPSNFJOYSA-H 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 239000001530 fumaric acid Substances 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920002266 Pluriol® Polymers 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-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
- 229930192474 thiophene Natural products 0.000 description 4
- IIQLVLWFQUUZII-UHFFFAOYSA-N 2-amino-5-(4-amino-3-carboxyphenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1C1=CC=C(N)C(C(O)=O)=C1 IIQLVLWFQUUZII-UHFFFAOYSA-N 0.000 description 3
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229910021575 Iron(II) bromide Inorganic materials 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 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
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- ZUCRGHABDDWQPY-UHFFFAOYSA-N pyrazine-2,3-dicarboxylic acid Chemical compound OC(=O)C1=NC=CN=C1C(O)=O ZUCRGHABDDWQPY-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 229910052727 yttrium Inorganic materials 0.000 description 3
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
- 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
- OYFRNYNHAZOYNF-UHFFFAOYSA-N 2,5-dihydroxyterephthalic acid Chemical compound OC(=O)C1=CC(O)=C(C(O)=O)C=C1O OYFRNYNHAZOYNF-UHFFFAOYSA-N 0.000 description 2
- CAWMOPYMZTVESL-UHFFFAOYSA-N 2-[1-(2-carboxyphenyl)-2-adamantyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1C(C=2C(=CC=CC=2)C(O)=O)(C2)CC3CC2CC1C3 CAWMOPYMZTVESL-UHFFFAOYSA-N 0.000 description 2
- LQWVYIRHSBXGBX-UHFFFAOYSA-N 2-[2,2,3-tris(2-carboxyphenyl)-1-adamantyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1(C(C(C2)(C=3C(=CC=CC=3)C(O)=O)C3)(C=4C(=CC=CC=4)C(O)=O)C=4C(=CC=CC=4)C(O)=O)CC3CC2C1 LQWVYIRHSBXGBX-UHFFFAOYSA-N 0.000 description 2
- PAMBMUOTYPLTQG-UHFFFAOYSA-N 2-[2,3-bis(2-carboxyphenyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC(C=2C(=CC=CC=2)C(O)=O)=C1C1=CC=CC=C1C(O)=O PAMBMUOTYPLTQG-UHFFFAOYSA-N 0.000 description 2
- CIEZZGWIJBXOTE-UHFFFAOYSA-N 2-[bis(carboxymethyl)amino]propanoic acid Chemical compound OC(=O)C(C)N(CC(O)=O)CC(O)=O CIEZZGWIJBXOTE-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
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- 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
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- 239000013148 Cu-BTC MOF Substances 0.000 description 2
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- 229910052796 boron Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
- 229910052706 scandium Inorganic materials 0.000 description 2
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- 229910052719 titanium Inorganic materials 0.000 description 2
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 2
- NOSIKKRVQUQXEJ-UHFFFAOYSA-H tricopper;benzene-1,3,5-tricarboxylate Chemical compound [Cu+2].[Cu+2].[Cu+2].[O-]C(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1.[O-]C(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1 NOSIKKRVQUQXEJ-UHFFFAOYSA-H 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
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- LOGBRYZYTBQBTB-UHFFFAOYSA-N butane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CCC(C(O)=O)CC(O)=O LOGBRYZYTBQBTB-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- DJKGDNKYTKCJKD-UHFFFAOYSA-N chlorendic acid Chemical compound ClC1=C(Cl)C2(Cl)C(C(=O)O)C(C(O)=O)C1(Cl)C2(Cl)Cl DJKGDNKYTKCJKD-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- MUYSADWCWFFZKR-UHFFFAOYSA-N cinchomeronic acid Chemical compound OC(=O)C1=CC=NC=C1C(O)=O MUYSADWCWFFZKR-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- PUDGCYJEHVWLAE-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid;hexadecanedioic acid Chemical compound OC(=O)C1(C(O)=O)CCC1.OC(=O)CCCCCCCCCCCCCCC(O)=O PUDGCYJEHVWLAE-UHFFFAOYSA-N 0.000 description 1
- QDKOFCUUXIAICD-UHFFFAOYSA-N cyclohex-2-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCC=C1C(O)=O QDKOFCUUXIAICD-UHFFFAOYSA-N 0.000 description 1
- ILUAAIDVFMVTAU-UHFFFAOYSA-N cyclohex-4-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CC=CCC1C(O)=O ILUAAIDVFMVTAU-UHFFFAOYSA-N 0.000 description 1
- STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical class OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 description 1
- WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 description 1
- LUEPYSLOLQVVCZ-UHFFFAOYSA-N decane-1,2,9,10-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)CCCCCCC(C(O)=O)CC(O)=O LUEPYSLOLQVVCZ-UHFFFAOYSA-N 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- HDFFVHSMHLDSLO-UHFFFAOYSA-M dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)([O-])OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-M 0.000 description 1
- HQZAZPULUDJUDP-UHFFFAOYSA-N dodecane-1,2,11,12-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)CCCCCCCCC(C(O)=O)CC(O)=O HQZAZPULUDJUDP-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- FYHFEMFNYGEMRB-UHFFFAOYSA-N hexane-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)CCC(C(O)=O)CC(O)=O FYHFEMFNYGEMRB-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 description 1
- ODBLHEXUDAPZAU-UHFFFAOYSA-N isocitric acid Chemical compound OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000013335 mesoporous material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012229 microporous material Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QUMITRDILMWWBC-UHFFFAOYSA-N nitroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C([N+]([O-])=O)=C1 QUMITRDILMWWBC-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- WDAISVDZHKFVQP-UHFFFAOYSA-N octane-1,2,7,8-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)CCCCC(C(O)=O)CC(O)=O WDAISVDZHKFVQP-UHFFFAOYSA-N 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- LAHAPBJSVSVFGR-UHFFFAOYSA-N oxane-4,4-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCOCC1 LAHAPBJSVSVFGR-UHFFFAOYSA-N 0.000 description 1
- UFOIOXZLTXNHQH-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1OC(C(O)=O)C(C(O)=O)C1C(O)=O UFOIOXZLTXNHQH-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- KIZSMODMWVZSNT-UHFFFAOYSA-N perylene-1,2-dicarboxylic acid Chemical compound C1=CC(C2=C(C(C(=O)O)=CC=3C2=C2C=CC=3)C(O)=O)=C3C2=CC=CC3=C1 KIZSMODMWVZSNT-UHFFFAOYSA-N 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- SDPOODQJUWAHOW-UHFFFAOYSA-N perylene-3,9-dicarboxylic acid Chemical compound C=12C3=CC=CC2=C(C(O)=O)C=CC=1C1=CC=CC2=C1C3=CC=C2C(=O)O SDPOODQJUWAHOW-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- GMIOYJQLNFNGPR-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CN=C(C(O)=O)C=N1 GMIOYJQLNFNGPR-UHFFFAOYSA-N 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- JPGZDTDZZDLVHW-UHFFFAOYSA-N quinoline-2,4-dicarboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC(C(O)=O)=C21 JPGZDTDZZDLVHW-UHFFFAOYSA-N 0.000 description 1
- SXXBQGWQCRMKHR-UHFFFAOYSA-N quinoline-3,4-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CN=C21 SXXBQGWQCRMKHR-UHFFFAOYSA-N 0.000 description 1
- WCHKKUMRGPRZOG-UHFFFAOYSA-N quinoline-7,8-dicarboxylic acid Chemical compound C1=CC=NC2=C(C(O)=O)C(C(=O)O)=CC=C21 WCHKKUMRGPRZOG-UHFFFAOYSA-N 0.000 description 1
- CQZDWYYGOZOTHY-UHFFFAOYSA-N quinoxaline-2,3-dicarboxylic acid Chemical compound C1=CC=C2N=C(C(O)=O)C(C(=O)O)=NC2=C1 CQZDWYYGOZOTHY-UHFFFAOYSA-N 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ZWWLLYJRPKYTDF-UHFFFAOYSA-N thiophene-3,4-dicarboxylic acid Chemical compound OC(=O)C1=CSC=C1C(O)=O ZWWLLYJRPKYTDF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- TXXHDPDFNKHHGW-ZPUQHVIOSA-N trans,trans-muconic acid Chemical compound OC(=O)\C=C\C=C\C(O)=O TXXHDPDFNKHHGW-ZPUQHVIOSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
- B01D53/228—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion characterised by specific membranes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0079—Manufacture of membranes comprising organic and inorganic components
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/14—Dynamic membranes
- B01D69/141—Heterogeneous membranes, e.g. containing dispersed material; Mixed matrix membranes
- B01D69/147—Heterogeneous membranes, e.g. containing dispersed material; Mixed matrix membranes containing embedded adsorbents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/14—Dynamic membranes
- B01D69/141—Heterogeneous membranes, e.g. containing dispersed material; Mixed matrix membranes
- B01D69/148—Organic/inorganic mixed matrix membranes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/02—Inorganic material
- B01D71/022—Metals
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
- B01J20/226—Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
- B01J20/28023—Fibres or filaments
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3244—Non-macromolecular compounds
- B01J20/3265—Non-macromolecular compounds with an organic functional group containing a metal, e.g. a metal affinity ligand
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/04—Calcium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/02—Metal coatings
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/10—Coatings without pigments
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H25/00—After-treatment of paper not provided for in groups D21H17/00 - D21H23/00
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2253/00—Adsorbents used in seperation treatment of gases and vapours
- B01D2253/20—Organic adsorbents
- B01D2253/204—Metal organic frameworks (MOF's)
Definitions
- the present invention relates to a process for coating at least part of a surface of a support with a porous metal-organic framework ("MOF").
- MOF metal-organic framework
- WO2009/056184 A1 describes, for example, spraying a suspension comprising a metal-organic framework onto materials such as nonwovens.
- A1 proposes applying adsorptive materials such as metal-organic frameworks to support materials by adhesive bonding or another method of fixing.
- MOF layers on silicone supports are described by G. Lu, J. Am. Chem. Soc. 132 (2010), 7832-7833.
- MOF layers on polyacrylonitrile supports are described by A. Centrone et al., J. Am. Chem. Soc. 132 (2010), 15687-15691 .
- Copper-benzenetricarboxylate MOF on copper membranes is described by H. Guo et al., J. Am. Chem. Soc. 131 (2009), 1646-1647.
- MOF layers have likewise been used for coating capillaries (N. Chang et al., J. Am. Chem. Soc. 132 (2010), 13645-13647).
- the object is achieved by a process for coating at least part of a surface of a support with a porous metal-organic framework comprising at least one at least bidentate organic compound coordinated to at least one metal ion, which comprises the steps
- step (b) spraying of the at least one part of the support surface with a second solution comprising the at least one at least bidentate organic compound, where step (b) is carried out before, after or simultaneously with step (a), to form a layer of the porous metal-organic framework.
- spraying-on of the first and second solution results in spontaneous formation of the metal-organic framework in the form of a layer on the support surface.
- spraying enables a faster production process than dipping processes to be carried out.
- the adhesion can be increased, so that bonding agents may be able to be dispensed with.
- Step (a) can be carried out before step (b). Step (a) can also be carried out after step (b). It is likewise possible for step (a) and step (b) to be carried out simultaneously.
- the resulting layer of the porous metal-organic framework can preferably be dried. If step (a) and (b) are not carried out simultaneously, a drying step can additionally be carried out between the two steps.
- the drying of the resulting layer of the porous metal-organic framework can, in particular, be effected by heating and/or by means of reduced pressure. Heating is carried out, for example, at a temperature in the range from 120°C to 300°C.
- the layer is preferably dried at at least 150°C.
- Spraying can be carried out by means of known spraying techniques. Spraying with the first, second or both with the first and the second solution is preferably carried out in a spraying drum.
- the solutions can be at different temperatures or the same temperature. This can be above or below room temperature. The same applies to the support surface.
- the first solution or the second solution or both the first and the second solution is/are preferably at room temperature (22°C).
- the first and second solutions can comprise identical or different solvents. Preference is given to using the same solvent. Possible solvents are solvents known in the prior art.
- the first solution or the second solution or both the first and second solutions is/are preferably an aqueous solution.
- the support surface can be a metallic or nonmetallic, optionally modified surface. Preference is given to a fibrous or foam surface.
- a sheet-like textile structure comprising or consisting of natural fibers and/or synthetic fibers (chemical fibers), in particular with the natural fibers being selected from the group consisting of wool fibers, cotton fibers (CO) and in particular cellulose and/or, in particular, with the synthetic fibers being selected from the group consisting of polyesters (PES); polyolefins, in particular polyethylene (PE) and/or polypropylene (PP); polyvinyl chlorides (CLF); polyvinylidene chlorides (CLF); acetates (CA); triacetates (CTA); polyacrylic (PAN); polyamides (PA), in particular aromatic, preferably flame-resistant polyamides; polyvinyl alcohols (PVAL); polyurethanes; polyvinyl esters; (meth)acrylates; polylactic acids (PLA); activated carbon; and mixtures thereof.
- natural fibers being selected from the group consisting of wool fibers, cotton fibers (CO) and in particular cellulose and/or, in particular, with the synthetic
- foams for sealing and insulation acoustic foams, rigid foams for packaging and flame-resistant foams composed of polyurethane, polystyrene, polyethylene, polypropylene, PVC, viscose, cellular rubber and mixtures thereof.
- foam composed of melamine resin Basotect
- a particularly suitable support material is filter material (including dressing material, cotton cloths, cigarette filters, filter papers as can, for example, be procured commercially for laboratory use).
- the first solution comprises the at least one metal ion. This can be used as metal salt.
- the second solution comprises the at least one at least bidentate organic compound. This can preferably be in the form of a solution of its salt.
- the at least one metal ion and the at least one at least bidentate organic compound form the porous metal-organic framework by contacting of the two solutions directly on the support surface to form a layer.
- Metal-organic frameworks which can be produced in this way are known in the prior art.
- Such metal-organic frameworks are, for example, described in US 5,648,508, EP-A-0 790 253, M. O'Keeffe et al., J . Sol. State Chem., 152 (2000), pages 3 to 20, H. Li et al., Nature 402, (1999), page 276, M. Eddaoudi et al., Topics in Catalysis 9, (1999), pages 105 to 1 1 1 , B. Chen et al., Science 29J., (2001 ), pages 1021 to 1023, DE-A-101 1 1 230, DE-A 10 2005 053430, WO-A 2007/054581 , WO-A 2005/049892 and WO-A 2007/023134.
- a further specific group of porous metal-organic frameworks comprises those in which the organic compound as ligand is a monocyclic, bicyclic or polycyclic ring system which is derived at least from one of the heterocycles selected from the group consisting of pyrrole, alpha-pyridone and gamma-pyridone and has at least two ring nitrogens.
- the electrochemical preparation of such frameworks is described in WO-A 2007/131955.
- the metal-organic frameworks according to the present invention comprise pores, in particular micropores and/or mesopores.
- Micropores are defined as pores having a diameter of 2 nm or less and mesopores are defined by a diameter in the range from 2 to 50 nm, in each case corresponding to the definition given in Pure & Applied Chem. 57 (1983), 603 - 619, in particular on page 606.
- the presence of micropores and/or mesopores can be checked by means of sorption measurements which determine the absorption capacity of the MOF for nitrogen at 77 kelvin in accordance with DI N 66131 and/or DI N 66134.
- the specific surface area, calculated according to the Langmuir model (DIN 66131 , 66134), of an MOF is preferably greater than 10 m 2 /g, more preferably greater than 20 m 2 /g, more preferably greater than 50 m 2 /g.
- the metal component in the framework according to the present invention is preferably selected from groups la, lla, Il ia, IVa to Vil la and lb to VIb. Particular preference is given to Mg, Ca, Sr, Ba, Sc, Y, Ln, Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W, Mn, Re, Fe, Ro, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag, Au, Zn, Cd, Hg, Al, Ga, In, TI, Si, Ge, Sn, Pb, As, Sb and Bi, where Ln represents lanthanides.
- Lanthanides are La, Ce, Pr, Nd, Pm, Sm, En, Gd, Tb, Dy, Ho, Er, Tm, Yb.
- Mg, Ca, Al, Y, Sc, Zr Ti, V, Cr, Mo, Fe, Co, Cu, Ni, Zn, Ln.
- Mg, Ca, Al, Mo, Y, Sc, Mg, Fe, Cu and Zn are preferred.
- Mg, Ca, Sc, Al, Cu and Zn are preferred.
- Mg, Ca, Al and Zn are preferred.
- At least bidentate organic compound refers to an organic compound which comprises at least one functional group which is able to form at least two coordinate bonds to a given metal ion and/or to form one coordinate bond to each of two or more, preferably two, metal atoms.
- the functional groups can also be heteroatoms of a heterocycle. Particular mention may here be made of nitrogen atoms.
- the at least two functional groups can in principle be bound to any suitable organic compound as long as it is ensured that the organic compound bearing these functional groups is capable of forming the coordinate bond and of producing the framework.
- the organic compounds comprising the at least two functional groups are preferably derived from a saturated or unsaturated aliphatic compound or an aromatic compound or a both aliphatic and aromatic compound.
- the aliphatic compound or the aliphatic part of the both aliphatic and aromatic compound can be linear and/or branched and/or cyclic, with a plurality of rings per compound also being possible.
- the aliphatic compound or the aliphatic part of the both aliphatic and aromatic compound more preferably comprises from 1 to 15, more preferably from 1 to 14, more preferably from 1 to 13, more preferably from 1 to 12, more preferably from 1 to 1 1 1 and particularly preferably from 1 to 10, carbon atoms, for example 1 , 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms. Particular preference is given here to, inter alia, methane, adamantane, acetylene, ethylene or butadiene.
- the aromatic compound or the aromatic part of the both aromatic and aliphatic compound can have one or more rings, for example two, three, four or five rings, with the rings being able to be present separately from one another and/or at least two rings being able to be present in fused form.
- the aromatic compound or the aromatic part of the both aliphatic and aromatic compound particularly preferably has one, two or three rings, with one or two rings being particularly preferred.
- each ring of said compound can independently comprise at least one heteroatom, for example N, O, S, B, P, Si, Al , preferably N, O and/or S.
- the aromatic compound or the aromatic part of the both aromatic and aliphatic compound more preferably comprises one or two C 6 rings, with the two being present either separately from one another or in fused form.
- the at least bidentate organic compound is more preferably an aliphatic or aromatic, acyclic or cyclic hydrocarbon which has from 1 to 18, preferably from 1 to 10 and in particular 6, carbon atoms and additionally has exclusively 2, 3 or 4 carboxyl groups as functional groups.
- the at least one at least bidentate organic compound is preferably derived from a dicarboxylic, tricarboxylic or tetracarboxylic acid.
- the at least bidentate organic compound is derived from a dicarboxylic acid such as oxalic acid, succinic acid, tartaric acid, 1 ,4-butanedicarboxylic acid, 1 ,4- butenedicarboxylic acid, 4-oxopyran-2,6-dicarboxylic acid, 1 ,6-hexanedicarboxylic acid, decanedicarboxylic acid, 1 ,8-heptadecanedicarboxylic acid, 1 ,9- heptadecanedicarboxlic acid, heptadecanedicarboxylic acid, acetylenedicarboxylic acid, 1 ,2-benzenedicarboxylic acid, 1 ,3-benzenedicarboxylic acid, 2,3- pyridinedicarboxylic acid, pyridine-2,3-dicarboxylic acid, 1 ,3-butadiene-1 ,4-dicarboxylic acid, 1 ,4
- the at least bidentate organic compound is more preferably one of the dicarboxylic acids mentioned by way of example above as such.
- the at least bidentate organic compound can, for example, be derived from a tricarboxylic acid such as
- the at least bidentate organic compound is more preferably one of the tricarboxylic acids mentioned by way of example above as such.
- Examples of an at least bidentate organic compound derived from a tetracarboxylic acid are 1 , 1 -dioxidoperylo[1 , 12-BCD]thiophene-3,4,9, 10-tetracarboxylic acid, perylenetetra- carboxylic acids such as perylene-3,4,9, 10-tetracarboxylic acid or (perylene-1 ,12- sulfone)-3,4,9,10-tetracarboxylic acid, butanetetracarboxylic acids such as 1 ,2,3,4- butanetetracarboxylic acid or meso-1 ,2,3,4-butanetetracarboxylic acid, decane-2, 4,6,8- tetracarboxylic acid , 1 ,4,7, 10, 13, 16-hexaoxacyclooctadecane-2,3, 1 1 , 12-tetracarboxylic acid, 1 ,2,4,5-benzenetetracarboxy
- the at least bidentate organic compound is more preferably one of the tetracarboxylic acids mentioned by way of example above as such.
- Preferred heterocycles as at least bidentate organic compound in which a coordinate bond is formed via the ring heteroatoms are the following substituted or unsubstituted ring systems:
- aromatic dicarboxylic, tricarboxylic or tetracarboxylic acids which can have one, two, three, four or more rings, with each of the rings being able to comprises at least one heteroatom and two or more rings being able to comprise identical or different heteroatoms.
- Suitable heteroatoms are, for example, N, O, S, B, P, and preferred heteroatoms are N, S and/or O.
- Suitable substituents here are, inter alia, -OH, a nitro group, an amino group or an alkyl or alkoxy group.
- Particularly preferred at least bidentate organic compounds are imidazolates such as 2-methylimidazolate, acetylenedicarboxylic acid (ADC), camphordicarboxylic acid, fumaric acid, succinic acid, benzenedicarboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid (BDC), aminoterephthalic acid, triethylenediamine (TEDA), methylglycinediacetic acid (MGDA), naphthalenedicarboxylic acids (NDC), biphenyldicarboxylic acids such as 4,4'-biphenyldicarboxylic acid (BPDC), pyrazinedicarboxylic acids such as 2,5-pyrazinedicarboxylic acid, bipyridinedicarboxylic acids such as 2,2'-bipyridinedicarboxylic acids such as 2,2'-bipyridine-5,5'-dicarboxylic acid, benzenetricarboxylic acids such as 1
- the metal-organic framework can also comprise one or more monodentate ligands and/or one or more at least bidentate ligands which are not derived from a dicarboxylic, tricarboxlic or tetracarboxylic acid.
- the metal-organic framework can also comprise one or more monodentate iigands.
- Preferred at least bidentate organic compounds are formic acid, acetic acid or an aliphatic dicarboxylic or polycarboxylic acid, for example malonic acid, fumaric acid or the like, in particular fumaric acid, or are derived from these.
- the term “derived” means that the at least one at least bidentate organic compound is present in partially or fully deprotonated form. Furthermore, the term “derived” means that the at least one at least bidentate organic compound can have further substituents. Thus, a dicarboxylic or polycarboxylic acid can have not only the carboxylic acid function but also one or more independent substituents such as amino, hydroxyl, methoxy, halogen or methyl groups. Preference is given to no further substituent being present.
- Suitable solvents for preparing the metal-organic framework are, inter alia, ethanol, dimethylformamide, toluene, methanol, chlorobenzene, diethylformamide, dimethyl sulfoxide, water, hydrogen peroxide, methylamine, sodium hydroxide solution, N-methylpyrrolidone ether, acetonitrile, benzyl chloride, triethylamine, ethylene glycol and mixtures thereof.
- Further metal ions, at least bidentate organic compounds and solvents for the preparation of MOFs are described, inter alia, in US-A 5,648,508 or DE-A 101 1 1 230.
- the pore size of the metal-organic framework can be controlled by selection of the appropriate ligand and/or the at least bidentate organic compound. In general, the larger the organic compound, the larger the pore size.
- the pore size is preferably from 0.2 nm to 30 nm, particularly preferably in the range from 0.3 nm to 3 nm, based on the crystalline material.
- metal-organic frameworks examples are given below.
- the metal and the at least bidentate ligand, the solvent and the cell parameters are also indicated. The latter were determined by X-ray diffraction.
- MOF-11 1 Cu(N0 3 ) 2 -2.5H 2 0 DMF 90 102.16 90 10.6767 18.781 21.052 C2/c
- MOF-110 Cu(N0 3 ) 2 -2.5H 2 0 DMF 90 90 120 20.0652 20.065 20.747 R-3/m
- MOF-2 to 4 MOF-9, MOF-31 to 36, MOF-39, MOF-69 to 80, MOF103 to 106, MOF-122, MOF-125, MOF-150, MOF-177, MOF-178, MOF-235, MOF-236, MOF-500, MOF-501 , MOF-502, MOF-505, I RMOF-1 , I RMOF-61 , IRMOP-13, I RMOP-51 , MIL-17, MIL-45, MIL-47, MI L-53, MIL-59, MIL-60, MI L-61 , MIL- 63, MI L-68, MI L-79, MI L-80, MIL-83, MIL-85, CPL-1 to 2, SZL-1 , which are described in the literature.
- metal-organic frameworks are MIL-53, Zn-tBu-isophthalic acid, AI-BDC, MOF-5, MOF-177, MOF-505, I RMOF-8, I RMOF-1 1 , Cu-BTC, AI-NDC, AI-aminoBDC, Cu-BDC-TEDA, Zn-BDC-TEDA, AI-BTC, Cu-BTC, AI-NDC, Mg-NDC, Al- fumarate, Zn-2-methylimidazolate, Zn-2-aminoimidazolate, Cu-biphenyldicarboxylate- TEDA, MOF-74, Cu-BPP, Sc-terephthalate.
- the layer of the porous metal-organic framework preferably has a mass in the range from 0.1 g/m 2 to 100 g/m 2 , more preferably from 1 g/m 2 to 80 g/m 2 , even more preferably from 3 g/m 2 to 50 g/m 2 .
- Solution 1 Deionized water (72.7 g) was placed in a vessel and AI 2 (S04) 3 x18H 2 0 (16.9 g, 25.5 mmol) was dissolved therein with stirring.
- Solution 2 Deionized water (87.3 g) was placed in a vessel and NaOH (6.1 g, 152.7 mmol) was dissolved therein with stirring. Fumaric acid (5.9 g, 50.9 mmol) was subsequently added while stirring and the mixture was stirred until a clear solution was formed.
- the surface area of the untreated filter papers is -1 -2 m 2 /g (specific surface area determined by the Langmuir method (LSA)). The surface areas of the coated papers were determined using a small sample of the filters ( ⁇ 100 mg).
- Example 1 Coating of filter papers by spraying-on the solutions in a rotating spraying drum at room temperature
- the filter paper was fixed in the spraying drum by means of adhesive tape and sprayed with solution 1 by means of a pump having a spray head at room temperature and rotation of the drum. After brief drying or in the moist state, solution 2 was sprayed on at room temperature by means of the pump. The filter paper was subsequently dried at room temperature in a jet of compressed air in the rotating drum. Uniform coating with a few flakes at the edge was obtained. The increase in mass of the filters was 1 .2-2.3 g.
- the dried papers were washed 4 times with 10 ml each time of H 2 0 on a suction filter under a slight water pump vacuum and dried again at room temperature.
- the filters obtained were activated at 150°C in a vacuum drying oven for 16 hours. XRD analysis of a selected sample displayed, in addition to Ibeta cellulose, a weak peak at 10 2-theta which can be assigned to the aluminum-fumarate MOF. The corresponding surface area was 51 m 2 /g LSA.
- Example 2 Coating of filter paper by simultaneous spraying-on of the solutions 1 and 2
- the filter paper was suspended and simultaneously sprayed with up to 1 ml of the two solutions (Eco-Spray sprayer and Desaga SG-1 sprayer).
- the treated filter paper was dried in air at room temperature while suspended. Homogeneous layers having a few small flakes were obtained.
- the increasing mass of the filters was 80-290 mg.
- the paper was subsequently washed 4 times with 10 ml each time of H 2 0 and dried at 100°C in a convection drying oven for 16 hours. 31 -279 mg were then detected on the filter papers. This corresponds to from 4.9 to 42 g/m 2 .
- XRD analysis of a selected sample displayed, in addition to Ibeta cellulose, a strong peak at 10 2-theta (crystallinity -3000) which can be assigned to the aluminum-fumarate MOF.
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US9527751B2 (en) | 2011-11-11 | 2016-12-27 | Basf Se | Organotemplate-free synthetic process for the production of a zeolitic material of the CHA-type structure |
WO2014066415A2 (en) * | 2012-10-22 | 2014-05-01 | The Texas A&M University System | Methods to rapidly deposit thin films (or coatings) of microporous materials on supports using thermally induced self-assembly |
DE102013202524A1 (en) | 2013-02-15 | 2014-08-21 | Universität Zu Köln | Preparing monopotassium-2,4,6-trifluorobenzene-1,3,5-tricarboxylate useful for preparing metal-organic frameworks, comprises oxidizing 3,5-dimethyl-2,4,6-trifluorobenzoic acid or its salt with potassium permanganate |
DE102013202517A1 (en) | 2013-02-15 | 2014-08-21 | Universität Zu Köln | Preparing mono-potassium 2-fluorobenzene-1,3,5-tricarboxylate, which is useful for producing metal-organic frameworks, comprises performing an oxidation of 1-fluoromesitylene with potassium permanganate |
JP6510027B2 (en) * | 2014-03-27 | 2019-05-08 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Porous membrane containing organometallic framework material |
US10406512B2 (en) | 2014-04-25 | 2019-09-10 | Colorado State University Research Foundation | Metal-organic framework functionalized polymeric compositions |
CN105524117B (en) * | 2014-09-28 | 2018-02-23 | 中国科学院大连化学物理研究所 | A kind of method that ultrasonic atomizatio prepares nanometer organic metal framework thing |
US9190114B1 (en) | 2015-02-09 | 2015-11-17 | Western Digital Technologies, Inc. | Disk drive filter including fluorinated and non-fluorinated nanopourous organic framework materials |
WO2017121893A1 (en) * | 2016-01-15 | 2017-07-20 | Basf Se | Water-tight breathable membrane |
CN109642094B (en) * | 2016-08-23 | 2021-09-14 | 巴斯夫欧洲公司 | Composite material |
CN106478406B (en) * | 2016-08-26 | 2018-09-14 | 东北大学 | A kind of preparation method of nano-grade metal-organic framework materials |
CN106955530A (en) * | 2017-04-21 | 2017-07-18 | 华中科技大学 | Cleaning filtration screen of air and preparation method based on Cu BTC sorbing materials |
JP7227648B2 (en) * | 2017-11-15 | 2023-02-22 | 大原パラヂウム化学株式会社 | Deodorant for daily life odor |
US11074899B2 (en) | 2018-03-15 | 2021-07-27 | International Business Machines Corporation | VOC sequestering acoustic foam |
KR102033780B1 (en) * | 2018-05-11 | 2019-10-17 | 한국과학기술연구원 | Catalyst-fiber complex containing UiO-66 type MOF-dispersed polymer and preparation method thereof |
CN109881483B (en) * | 2019-01-24 | 2021-12-17 | 浙江理工大学 | Method for functionally modifying polypropylene/cellulose spunlace non-woven fabric by using metal-organic framework material and application thereof |
CN110270312B (en) * | 2019-06-21 | 2022-07-15 | 四川农业大学 | Metal organic framework material-activated carbon composite fiber membrane and preparation method thereof |
CN110217864A (en) * | 2019-07-01 | 2019-09-10 | 陕西科技大学 | A kind of supported porous carbon carbonaceous cathodes material of graphite felt and its preparation method and application |
RU2745020C1 (en) * | 2019-11-27 | 2021-03-18 | Владимир Николаевич Говердовский | Method of manufacture of a noise absorbing material |
CN111569840B (en) * | 2020-05-12 | 2023-07-14 | 山东师范大学 | Adsorption material for organic pollutants, paper spray mass spectrum detection device and detection method |
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