JP2017515666A - 亜硝酸で後処理される複合ポリアミド膜 - Google Patents
亜硝酸で後処理される複合ポリアミド膜 Download PDFInfo
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- JP2017515666A JP2017515666A JP2016566274A JP2016566274A JP2017515666A JP 2017515666 A JP2017515666 A JP 2017515666A JP 2016566274 A JP2016566274 A JP 2016566274A JP 2016566274 A JP2016566274 A JP 2016566274A JP 2017515666 A JP2017515666 A JP 2017515666A
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- Prior art keywords
- acid
- thin film
- hydrogen
- polyamide layer
- monomer
- Prior art date
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- 239000004952 Polyamide Substances 0.000 title claims abstract description 73
- 229920002647 polyamide Polymers 0.000 title claims abstract description 73
- 239000012528 membrane Substances 0.000 title claims abstract description 68
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 239000002131 composite material Substances 0.000 title claims abstract description 19
- 239000000178 monomer Substances 0.000 claims abstract description 61
- -1 halogenated benzene compound Chemical class 0.000 claims abstract description 46
- 150000001266 acyl halides Chemical class 0.000 claims abstract description 36
- 239000010409 thin film Substances 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 150000001412 amines Chemical class 0.000 claims abstract description 25
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims abstract description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical group 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- FZRKAZHKEDOPNN-UHFFFAOYSA-N Nitric oxide anion Chemical compound O=[N-] FZRKAZHKEDOPNN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 2
- 229930194542 Keto Natural products 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 2
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000012634 fragment Substances 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000004332 silver Substances 0.000 description 11
- 229910052709 silver Inorganic materials 0.000 description 11
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 11
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 9
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 229920002492 poly(sulfone) Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 229940018564 m-phenylenediamine Drugs 0.000 description 7
- 238000001728 nano-filtration Methods 0.000 description 7
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 238000000197 pyrolysis Methods 0.000 description 7
- 238000001223 reverse osmosis Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 239000000539 dimer Substances 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000000777 acyl halide group Chemical group 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 239000012454 non-polar solvent Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 150000003141 primary amines Chemical group 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- RJHRQMQWMHKSOY-UHFFFAOYSA-N 3,5-dicarbonochloridoylbenzoic acid Chemical compound OC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 RJHRQMQWMHKSOY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000012695 Interfacial polymerization Methods 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- RFBZPOTVVHLWBP-UHFFFAOYSA-N 11-chloro-11-oxoundecanoic acid Chemical compound OC(=O)CCCCCCCCCC(Cl)=O RFBZPOTVVHLWBP-UHFFFAOYSA-N 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- SSIZLKDLDKIHEV-UHFFFAOYSA-N 2,6-dibromophenol Chemical compound OC1=C(Br)C=CC=C1Br SSIZLKDLDKIHEV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 101710134784 Agnoprotein Proteins 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000012696 Interfacial polycondensation Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000010504 bond cleavage reaction Methods 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000002338 electrophoretic light scattering Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000009501 film coating Methods 0.000 description 2
- 239000007888 film coating Substances 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- 238000001471 micro-filtration Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 238000011020 pilot scale process Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- UKISWDCMNXICCV-UHFFFAOYSA-N 1-phenyl-2-propylbenzene;phosphoric acid Chemical compound OP(O)(O)=O.CCCC1=CC=CC=C1C1=CC=CC=C1 UKISWDCMNXICCV-UHFFFAOYSA-N 0.000 description 1
- GPSHWNLDDARPCO-UHFFFAOYSA-N 10-chloro-10-oxodecanoic acid Chemical compound OC(=O)CCCCCCCCC(Cl)=O GPSHWNLDDARPCO-UHFFFAOYSA-N 0.000 description 1
- QLDZETGUBDKZAV-UHFFFAOYSA-N 12-chloro-12-oxododecanoic acid Chemical compound OC(=O)CCCCCCCCCCC(Cl)=O QLDZETGUBDKZAV-UHFFFAOYSA-N 0.000 description 1
- JZLBSZQDKQGACE-UHFFFAOYSA-N 2,3,5,6-tetrabromophenol Chemical compound OC1=C(Br)C(Br)=CC(Br)=C1Br JZLBSZQDKQGACE-UHFFFAOYSA-N 0.000 description 1
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- PBYIIRLNRCVTMQ-UHFFFAOYSA-N 2,3,5,6-tetrafluorophenol Chemical compound OC1=C(F)C(F)=CC(F)=C1F PBYIIRLNRCVTMQ-UHFFFAOYSA-N 0.000 description 1
- YXOVONWVXRDBDW-UHFFFAOYSA-N 2,3,5,6-tetraiodophenol Chemical compound OC1=C(I)C(I)=CC(I)=C1I YXOVONWVXRDBDW-UHFFFAOYSA-N 0.000 description 1
- UEVXAXSPNCMQIC-UHFFFAOYSA-N 2,3,6-tribromoaniline Chemical compound NC1=C(Br)C=CC(Br)=C1Br UEVXAXSPNCMQIC-UHFFFAOYSA-N 0.000 description 1
- VCNCNAPAHSSWCI-UHFFFAOYSA-N 2,3,6-tribromophenol Chemical compound OC1=C(Br)C=CC(Br)=C1Br VCNCNAPAHSSWCI-UHFFFAOYSA-N 0.000 description 1
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- ARVIPUPLHRCDBY-UHFFFAOYSA-N 2,3,6-triiodophenol Chemical compound OC1=C(I)C=CC(I)=C1I ARVIPUPLHRCDBY-UHFFFAOYSA-N 0.000 description 1
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- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- QHXWVACOZJQROG-UHFFFAOYSA-N 2-(3,5-dicarbonochloridoylanilino)acetic acid Chemical compound OC(=O)CNC1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 QHXWVACOZJQROG-UHFFFAOYSA-N 0.000 description 1
- NVUJTTGXXGPDJC-UHFFFAOYSA-N 2-(3,5-dicarbonochloridoylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 NVUJTTGXXGPDJC-UHFFFAOYSA-N 0.000 description 1
- CUYHJSGIPAHGPC-UHFFFAOYSA-N 2-(3,5-dicarbonochloridoylphenyl)acetic acid Chemical compound OC(=O)CC1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 CUYHJSGIPAHGPC-UHFFFAOYSA-N 0.000 description 1
- IEOJLOOURBMYCG-UHFFFAOYSA-N 2-(3-carbonochloridoylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC(C(Cl)=O)=C1 IEOJLOOURBMYCG-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 1
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- VVOSATWFENUSTP-UHFFFAOYSA-N ethylbenzene;1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound CCC1=CC=CC=C1.COCCOCCOC VVOSATWFENUSTP-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000009292 forward osmosis Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000012510 hollow fiber Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004797 ketoamides Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- WUQGUKHJXFDUQF-UHFFFAOYSA-N naphthalene-1,2-dicarbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(C(=O)Cl)=CC=C21 WUQGUKHJXFDUQF-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 125000005499 phosphonyl group Chemical group 0.000 description 1
- 125000001863 phosphorothioyl group Chemical group *P(*)(*)=S 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- SFENPMLASUEABX-UHFFFAOYSA-N trihexyl phosphate Chemical compound CCCCCCOP(=O)(OCCCCCC)OCCCCCC SFENPMLASUEABX-UHFFFAOYSA-N 0.000 description 1
- QMKYBPDZANOJGF-UHFFFAOYSA-N trimesic acid Natural products OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 1
- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
- QJAVUVZBMMXBRO-UHFFFAOYSA-N tripentyl phosphate Chemical compound CCCCCOP(=O)(OCCCCC)OCCCCC QJAVUVZBMMXBRO-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
- B01D69/1251—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction by interfacial polymerisation
-
- 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
- B01D67/0002—Organic membrane manufacture
- B01D67/0006—Organic membrane manufacture by chemical reactions
-
- 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
- B01D67/0081—After-treatment of organic or inorganic membranes
- B01D67/0093—Chemical modification
-
- 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
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
-
- 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
- B01D71/06—Organic material
- B01D71/56—Polyamides, e.g. polyester-amides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/40—Details relating to membrane preparation in-situ membrane formation
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Polyamides (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
Description
Xはハロゲン(−F、−Cl、−Br、−I、好ましくは−Brまたは−I)から選択され、
Yは水素(−H)、カルボン酸(−COOH)、スルホン酸(−SO3H)、またはそれらの塩から選択され、
A、A’、A’’、及びA’’’は独立して、ハロゲン、水素、ヒドロキシル(−OH)、アルコキシ(好ましくは1〜5個の炭素原子を有するアルキル、例えばメトキシ−OCH3)、エステル(例えば−O−CO−CH3)、アミノ(例えば−NRR’、式中、R及びR’は、水素、または好ましくは1〜5個の炭素原子を有するアルキル基である)、ケト−アミド(例えば−NH−CO−CH2−CO−CH3)、及び1〜5個の炭素原子を有するアルキル基から選択されるが、但し、A、A’、A’’及びA’’’のうちの少なくとも1つがヒドロキシル、アミノ、及びケト−アミドから選択され、A、A’、A’’及びA’’’のうちの少なくとも1つに対してオルソまたはパラにある置換基が水素であるものとする。好ましい実施形態の下位群において、Yは水素またはカルボン酸から選択され、A、A’、A’’、及びA’’’は独立して、水素、ヒドロキシル、アルコキシ、及びアミノから選択される。以下のハロゲン化ベンゼン化合物が代表的な種類である:2−ヨードアニリン、2−ブロンモアニリン、2−クロロアニリン、2−フルオロアニリン、3−ヨードアニリン、3−ブロンモアニリン、3−クロロアニリン、3−フルオロアニリン、4−ヨードアニリン、4−ブロンモアニリン、4−クロロアニリン、4−フルオロアニリン、2−ヨードフェノール、2−ブロモフェノール、2−クロロフェノール、2−フルオロフェノール、3−ヨードフェノール、3−ブロモフェノール、3−クロロフェノール、3−フルオロフェノール、4−ヨードフェノール、4−ブロモフェノール、4−クロロフェノール、4−フルオロフェノール、5−ヨードベンゼン−1,3−ジアミン、5−ブロモベンゼン−1,3−ジアミン、5−クロロベンゼン−1,3−ジアミン、5−フルオロベンゼン−1,3−ジアミン、5−ヨードベンゼン−1,3−ジオール、5−ブロモベンゼン−1,3−ジオール、5−クロロベンゼン−1,3−ジオール、5−フルオロベンゼン−1,3−ジオール、3−アミノ−5−ヨードフェノール、3−アミノ−5−ブロモフェノール、3−アミノ−5−クロロフェノール、3−アミノ−5−フルオロフェノール、3−ヒドロキシ−5−ヨード安息香酸、3−ヒドロキシ−5−ブロモ安息香酸、3−ヒドロキシ−5−クロロ安息香酸、3−ヒドロキシ−5−フルオロ安息香酸、3−ヒドロキシ−5−ヨードベンゼンスルホン酸、3−ヒドロキシ−5−ブロモベンゼンスルホン酸、3−ヒドロキシ−5−クロロベンゼンスルホン酸、3−ヒドロキシ−5−フルオロベンゼンスルホン酸、3−アミノ−5−ヨード安息香酸、3−アミノ−5−ブロモ安息香酸、3−アミノ−5−クロロ安息香酸、3−アミノ−5−フルオロ安息香酸、3−アミノ−5−ヨードベンゼンスルホン酸、3−アミノ−5−ブロモベンゼンスルホン酸、3−アミノ−5−クロロベンゼンスルホン酸、3−アミノ−5−フルオロベンゼンスルホン酸、2,6−ジヨードフェノール、2,6−ジブロモフェノール、2,6−ジクロロフェノール、2,6−ジフルオロフェノール、2,6−ジヨードアニリン、2,6−ジブロモアニリン、2,6−ジクロロアニリン、2,6−フルオロアニリン、2,3,6−トリヨードフェノール、2,3,6−トリブロモフェノール、2,3,6−トリクロロフェノール、2,3,6−トリフルオロフェノール、2,3,6−トリヨードアニリン、2,3,6−トリブロモアニリン、2,3,6−トリクロロアニリン、2,3,6−トリフルオロアニリン、2,3,5,6−テトラヨードフェノール、2,3,5,6−テトラブロモフェノール、2,3,5,6−テトラクロロフェノール、2,3,5,6−テトラフルオロフェノール、2,3,5,6−テトラヨードアニリン、2,3,5,6−テトラブロモアニリン、2,3,5,6−テトラクロロアニリン、2,3,5,6−テトラフルオラニリン(tetrafluoraniline)。
Claims (8)
- 多孔質支持体及び薄フィルムポリアミド層を含む複合ポリアミド膜を作製する方法であって、
i)多官能性アミンモノマーを含む極性溶液及び多官能性ハロゲン化アシルモノマーを含む非極性溶液を多孔質支持体の表面に適用し、前記モノマーを界面重合して、薄フィルムポリアミド層を形成することと、
ii)前記薄フィルムポリアミド層を亜硝酸に曝露することと、を含み、
前記方法は、前記薄フィルムポリアミド層を以下の式によって表されるハロゲン化ベンゼン化合物で処理することを特徴とし、
Xはハロゲン(−F、−Cl、−Br、−I)から選択され、
Yは水素(−H)、カルボン酸(−COOH)、スルホン酸(−SO3H)、またはそれらの塩から選択され、
A、A’、A’’、及びA’’’は独立して、ハロゲン、水素、ヒドロキシル(−OH)、アルコキシ(好ましくはメトキシ−OCH3)、エステル(例えば−O−CO−CH3)、アミノ(第一級、第二級、または第三級アミノを含む)、ケト−アミド、及び1〜5個の炭素原子を有するアルキル基から選択されるが、
但し、A、A’、A’’、及びA’’’のうちの少なくとも1つが、ヒドロキシル、アミノ(例えば−NRR’、式中、R及びR’は水素、または好ましくは1〜5個の炭素原子を有するアルキル基である)、ケト−アミド(例えば−NH−CO−CH2−CO−CH3)から選択され、A、A’、A’’、及びA’’’のうちの少なくとも1つに対してオルソまたはパラにある置換基が水素であるものとする、方法。 - 前記非極性溶液が、少なくとも1つのカルボン酸官能基またはその塩で置換されるC2−C20炭化水素部分と、ハロゲン化アシル、ハロゲン化スルホニル、及び無水物から選択される少なくとも1つのアミン反応性官能基とを含む酸含有モノマーを更に含み、前記酸含有モノマーが前記多官能性ハロゲン化アシルモノマーとは異なる、請求項2に記載の方法。
- 前記非極性溶液が、少なくとも1つのカルボン酸官能基またはその塩で置換されるC2−C20炭化水素部分と、ハロゲン化アシル、ハロゲン化スルホニル、及び無水物から選択される少なくとも1つのアミン反応性官能基とを含む酸含有モノマーを更に含み、前記酸含有モノマーが前記多官能性ハロゲン化アシルモノマーとは異なる、請求項1に記載の方法。
- 前記酸含有モノマーが、少なくとも2つのアミン反応性官能基を含む、請求項4に記載の方法。
- 前記薄フィルムポリアミド層が、前記薄フィルムポリアミド層を亜硝酸に曝露する前記ステップの前に、RBSによって計測される、pH9.5で少なくとも0.18モル/kgの解離したカルボン酸含有量を有する、請求項1に記載の方法。
- 前記薄フィルムポリアミド層をハロゲン化ベンゼン化合物で処理する前記ステップが、前記薄フィルムポリアミド層を亜硝酸に曝露するステップの前に実行される、請求項1に記載の方法。
- Yが水素またはカルボン酸から選択され、A、A’、A’’、及びA’’’が独立して、水素、ヒドロキシル、アルコキシ、及びアミノから選択される、請求項1に記載の方法。
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EP3092061B1 (en) | 2014-01-09 | 2020-02-05 | Dow Global Technologies LLC | Composite polyamide membrane having high acid content and low azo content |
WO2015167759A1 (en) | 2014-04-28 | 2015-11-05 | Dow Global Technologies Llc | Composite polyamide membrane post-treated with nitrous acid |
JP6640739B2 (ja) | 2014-05-14 | 2020-02-05 | ダウ グローバル テクノロジーズ エルエルシー | 亜硝酸で後処理される複合ポリアミド膜 |
AU2019358704A1 (en) * | 2018-10-11 | 2021-03-25 | National University Of Singapore | Antifouling polymer for reverse osmosis and membrane comprising same |
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JP2009536874A (ja) * | 2006-05-12 | 2009-10-22 | ダウ グローバル テクノロジーズ インコーポレイティド | 改質膜 |
WO2011078047A1 (ja) * | 2009-12-24 | 2011-06-30 | 東レ株式会社 | 複合半透膜およびその製造方法 |
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JP2014504551A (ja) * | 2011-01-24 | 2014-02-24 | ダウ グローバル テクノロジーズ エルエルシー | 複合ポリアミド膜 |
WO2013048765A1 (en) * | 2011-09-29 | 2013-04-04 | Dow Global Technologies Llc | Composite polyamide membrane derived from carboxylic acid containing acyl halide monomer |
WO2014014666A1 (en) * | 2012-07-19 | 2014-01-23 | Dow Global Technologies Llc | Membrane derived from polyfunctional amine and combination of different polyfunctional amine-reactive monomers |
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JP6654576B2 (ja) | 2020-02-26 |
WO2015175254A1 (en) | 2015-11-19 |
KR20170002489A (ko) | 2017-01-06 |
CN106457160A (zh) | 2017-02-22 |
US20170065938A1 (en) | 2017-03-09 |
KR102357884B1 (ko) | 2022-02-03 |
CN106457160B (zh) | 2019-10-08 |
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