KR101946792B1 - 카복실산 함유 아실 할라이드 단량체로부터 유도된 복합 폴리아미드 멤브레인 - Google Patents
카복실산 함유 아실 할라이드 단량체로부터 유도된 복합 폴리아미드 멤브레인 Download PDFInfo
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- KR101946792B1 KR101946792B1 KR1020147011507A KR20147011507A KR101946792B1 KR 101946792 B1 KR101946792 B1 KR 101946792B1 KR 1020147011507 A KR1020147011507 A KR 1020147011507A KR 20147011507 A KR20147011507 A KR 20147011507A KR 101946792 B1 KR101946792 B1 KR 101946792B1
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- Prior art keywords
- monomer
- carboxylic acid
- acyl halide
- coating solution
- concentration
- Prior art date
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- 239000000178 monomer Substances 0.000 title claims abstract description 103
- 239000012528 membrane Substances 0.000 title claims abstract description 69
- 150000001266 acyl halides Chemical class 0.000 title claims abstract description 53
- 239000004952 Polyamide Substances 0.000 title claims abstract description 37
- 229920002647 polyamide Polymers 0.000 title claims abstract description 37
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims abstract description 35
- 239000002131 composite material Substances 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 20
- 150000001412 amines Chemical class 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 9
- 239000010409 thin film Substances 0.000 claims abstract description 9
- 238000012695 Interfacial polymerization Methods 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 35
- 239000011248 coating agent Substances 0.000 claims description 30
- 238000000576 coating method Methods 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 229910019142 PO4 Inorganic materials 0.000 claims description 22
- 150000002430 hydrocarbons Chemical class 0.000 claims description 22
- 239000004215 Carbon black (E152) Substances 0.000 claims description 21
- 229930195733 hydrocarbon Natural products 0.000 claims description 21
- 239000010452 phosphate Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 84
- 150000001263 acyl chlorides Chemical class 0.000 description 36
- 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 29
- 239000010410 layer Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 18
- 235000021317 phosphate Nutrition 0.000 description 14
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 229940018564 m-phenylenediamine Drugs 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 238000001223 reverse osmosis Methods 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- OHFLNNVKHIOKKU-UHFFFAOYSA-N 3-carbonochloridoylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C(Cl)=O)=C1 OHFLNNVKHIOKKU-UHFFFAOYSA-N 0.000 description 6
- -1 aromatic carboxylic acids Chemical class 0.000 description 6
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- AKRGLPCOXCYKNF-UHFFFAOYSA-N 5-chloro-5-oxopentanoic acid Chemical compound OC(=O)CCCC(Cl)=O AKRGLPCOXCYKNF-UHFFFAOYSA-N 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 230000035699 permeability Effects 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 5
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
- 229920002125 Sokalan® Polymers 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000004907 flux Effects 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229920002492 poly(sulfone) Polymers 0.000 description 4
- 239000011148 porous material Substances 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
- YJKJKJNKFIDCMN-UHFFFAOYSA-N 6-chloro-6-oxohexanoic acid Chemical compound OC(=O)CCCCC(Cl)=O YJKJKJNKFIDCMN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 3
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- GPSHWNLDDARPCO-UHFFFAOYSA-N 10-chloro-10-oxodecanoic acid Chemical compound OC(=O)CCCCCCCCC(Cl)=O GPSHWNLDDARPCO-UHFFFAOYSA-N 0.000 description 2
- XFRCTKZKWPSIOT-UHFFFAOYSA-N 3-carbonochloridoyl-5-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(C(Cl)=O)=C1 XFRCTKZKWPSIOT-UHFFFAOYSA-N 0.000 description 2
- KZCJYXBMTDCKRZ-UHFFFAOYSA-N 3-carbonochloridoyl-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 KZCJYXBMTDCKRZ-UHFFFAOYSA-N 0.000 description 2
- PVOFLWDXEXGWNT-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarbonyl chloride Chemical compound OC1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 PVOFLWDXEXGWNT-UHFFFAOYSA-N 0.000 description 2
- 238000012696 Interfacial polycondensation Methods 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 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 2
- 238000001471 micro-filtration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-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
- YLMXJINLTYLWAR-UHFFFAOYSA-N 1-carbonochloridoylcyclopentane-1-carboxylic acid Chemical compound ClC(=O)C1(CCCC1)C(=O)O YLMXJINLTYLWAR-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
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 1
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- QXSKFLYCTIMTEU-UHFFFAOYSA-N 2,4-dicarbonochloridoylcyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CC(C(Cl)=O)CC1C(Cl)=O QXSKFLYCTIMTEU-UHFFFAOYSA-N 0.000 description 1
- FNHMKBLWJZMQPH-UHFFFAOYSA-N 2,4-dioxo-3-oxabicyclo[3.3.1]nonane-7-carboxylic acid Chemical compound C1C2CC(C(=O)O)CC1C(=O)OC2=O FNHMKBLWJZMQPH-UHFFFAOYSA-N 0.000 description 1
- MFFNQPWYQIHSSN-UHFFFAOYSA-N 2-chloro-10-oxodecanoic acid Chemical compound ClC(C(=O)O)CCCCCCCC=O MFFNQPWYQIHSSN-UHFFFAOYSA-N 0.000 description 1
- KFYIOCCUPRWVCY-UHFFFAOYSA-N 2-nitrobenzene-1,3-dicarbonyl chloride Chemical compound [O-][N+](=O)C1=C(C(Cl)=O)C=CC=C1C(Cl)=O KFYIOCCUPRWVCY-UHFFFAOYSA-N 0.000 description 1
- 125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 description 1
- NFVVXABAENGSMQ-UHFFFAOYSA-N 3,5-dicarbonochloridoylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CC(C(Cl)=O)CC(C(Cl)=O)C1 NFVVXABAENGSMQ-UHFFFAOYSA-N 0.000 description 1
- UUOFSRVHZJTWDE-UHFFFAOYSA-N 3-chloro-3-oxopropanoic acid Chemical compound OC(=O)CC(Cl)=O UUOFSRVHZJTWDE-UHFFFAOYSA-N 0.000 description 1
- GNIZQCLFRCBEGE-UHFFFAOYSA-N 3-phenylbenzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(Cl)=O GNIZQCLFRCBEGE-UHFFFAOYSA-N 0.000 description 1
- OYEQKMASMPBQMP-UHFFFAOYSA-N 4-carbonochloridoylbenzoic acid Chemical compound OC(=O)C1=CC=C(C(Cl)=O)C=C1 OYEQKMASMPBQMP-UHFFFAOYSA-N 0.000 description 1
- AAYIVNQHGGVCOZ-UHFFFAOYSA-N 4-carbonochloridoylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(C(Cl)=O)CC1 AAYIVNQHGGVCOZ-UHFFFAOYSA-N 0.000 description 1
- MMZMROHDQCJAJT-UHFFFAOYSA-N 4-chloro-4-oxobutanoic acid Chemical compound OC(=O)CCC(Cl)=O MMZMROHDQCJAJT-UHFFFAOYSA-N 0.000 description 1
- OHIVUAREQFICPK-UHFFFAOYSA-N 5-nitrobenzene-1,3-dicarbonyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 OHIVUAREQFICPK-UHFFFAOYSA-N 0.000 description 1
- 239000004135 Bone phosphate Substances 0.000 description 1
- QDWCGEYGCQARBY-UHFFFAOYSA-N ClC(=O)C1=CC=C2C=C(C(=C(C2=C1)C(=O)Cl)C(=O)O)C(=O)Cl Chemical compound ClC(=O)C1=CC=C2C=C(C(=C(C2=C1)C(=O)Cl)C(=O)O)C(=O)Cl QDWCGEYGCQARBY-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- 125000000777 acyl halide group Chemical group 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RPHKINMPYFJSCF-UHFFFAOYSA-N benzene-1,3,5-triamine Chemical compound NC1=CC(N)=CC(N)=C1 RPHKINMPYFJSCF-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- DWSYMNWJOYKKCK-UHFFFAOYSA-N butyl diethyl phosphate Chemical compound CCCCOP(=O)(OCC)OCC DWSYMNWJOYKKCK-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MYTYKMBAJLQHLQ-UHFFFAOYSA-N butyl heptyl hexyl phosphate Chemical compound CCCCCCCOP(=O)(OCCCC)OCCCCCC MYTYKMBAJLQHLQ-UHFFFAOYSA-N 0.000 description 1
- DJQFQXHRKYELGT-UHFFFAOYSA-N butyl heptyl hydrogen phosphate Chemical compound CCCCCCCOP(O)(=O)OCCCC DJQFQXHRKYELGT-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- XWALRFDLDRDCJG-UHFFFAOYSA-N cyclobutane-1,1,2,2-tetracarbonyl chloride Chemical compound ClC(=O)C1(C(Cl)=O)CCC1(C(Cl)=O)C(Cl)=O XWALRFDLDRDCJG-UHFFFAOYSA-N 0.000 description 1
- LXLCHRQXLFIZNP-UHFFFAOYSA-N cyclobutane-1,1-dicarbonyl chloride Chemical compound ClC(=O)C1(C(Cl)=O)CCC1 LXLCHRQXLFIZNP-UHFFFAOYSA-N 0.000 description 1
- PBWUKDMYLKXAIP-UHFFFAOYSA-N cyclohexane-1,1,2-tricarbonyl chloride Chemical compound ClC(=O)C1CCCCC1(C(Cl)=O)C(Cl)=O PBWUKDMYLKXAIP-UHFFFAOYSA-N 0.000 description 1
- MLCGVCXKDYTMRG-UHFFFAOYSA-N cyclohexane-1,1-dicarbonyl chloride Chemical compound ClC(=O)C1(C(Cl)=O)CCCCC1 MLCGVCXKDYTMRG-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- DCXMNNZFVFSGJX-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarbonyl chloride Chemical compound ClC(=O)C1(C(Cl)=O)CCCC1(C(Cl)=O)C(Cl)=O DCXMNNZFVFSGJX-UHFFFAOYSA-N 0.000 description 1
- JREFGECMMPJUHM-UHFFFAOYSA-N cyclopentane-1,1,2-tricarbonyl chloride Chemical compound ClC(=O)C1CCCC1(C(Cl)=O)C(Cl)=O JREFGECMMPJUHM-UHFFFAOYSA-N 0.000 description 1
- YYLFLXVROAGUFH-UHFFFAOYSA-N cyclopentane-1,1-dicarbonyl chloride Chemical compound ClC(=O)C1(C(Cl)=O)CCCC1 YYLFLXVROAGUFH-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- CRMQURWQJQPUMY-UHFFFAOYSA-N cyclopropane-1,1,2-tricarbonyl chloride Chemical compound ClC(=O)C1CC1(C(Cl)=O)C(Cl)=O CRMQURWQJQPUMY-UHFFFAOYSA-N 0.000 description 1
- YICSVBJRVMLQNS-UHFFFAOYSA-N dibutyl phenyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OC1=CC=CC=C1 YICSVBJRVMLQNS-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000012510 hollow fiber Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001728 nano-filtration Methods 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
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MEQCXWDKLOGGRO-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarbonyl chloride Chemical compound ClC(=O)C1OC(C(Cl)=O)C(C(Cl)=O)C1C(Cl)=O MEQCXWDKLOGGRO-UHFFFAOYSA-N 0.000 description 1
- LSHSZIMRIAJWRM-UHFFFAOYSA-N oxolane-2,3-dicarbonyl chloride Chemical compound ClC(=O)C1CCOC1C(Cl)=O LSHSZIMRIAJWRM-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 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
- 239000012466 permeate Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000765 poly(2-oxazolines) Chemical class 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 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
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- SFENPMLASUEABX-UHFFFAOYSA-N trihexyl phosphate Chemical compound CCCCCCOP(=O)(OCCCCCC)OCCCCCC SFENPMLASUEABX-UHFFFAOYSA-N 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
- 238000005406 washing Methods 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Polyamides (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161540555P | 2011-09-29 | 2011-09-29 | |
| US61/540,555 | 2011-09-29 | ||
| US201261675613P | 2012-07-25 | 2012-07-25 | |
| US61/675,613 | 2012-07-25 | ||
| PCT/US2012/055271 WO2013048765A1 (en) | 2011-09-29 | 2012-09-14 | Composite polyamide membrane derived from carboxylic acid containing acyl halide monomer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20140079442A KR20140079442A (ko) | 2014-06-26 |
| KR101946792B1 true KR101946792B1 (ko) | 2019-02-13 |
Family
ID=46982937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147011507A Active KR101946792B1 (ko) | 2011-09-29 | 2012-09-14 | 카복실산 함유 아실 할라이드 단량체로부터 유도된 복합 폴리아미드 멤브레인 |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP2760570B1 (enExample) |
| JP (1) | JP6027124B2 (enExample) |
| KR (1) | KR101946792B1 (enExample) |
| CN (1) | CN103889563B (enExample) |
| ES (1) | ES2556832T3 (enExample) |
| IL (1) | IL231573B (enExample) |
| IN (1) | IN2014CN02212A (enExample) |
| WO (1) | WO2013048765A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101920194B1 (ko) | 2011-01-24 | 2019-02-08 | 다우 글로벌 테크놀로지스 엘엘씨 | 복합 폴리아미드 막 |
| CN103764264B (zh) | 2011-08-31 | 2016-11-16 | 陶氏环球技术有限责任公司 | 源自包含胺反应性官能团和含磷官能团的单体的复合聚酰胺膜 |
| WO2013048764A1 (en) | 2011-09-29 | 2013-04-04 | Dow Global Technologies Llc | Method for preparing high purity mono-hydrolyzed acyl halide compound |
| EP2776146B1 (en) | 2012-01-06 | 2020-05-13 | DDP Specialty Electronic Materials US, Inc. | Method of preparation of a composite polyamide membrane |
| US9610542B2 (en) * | 2012-07-19 | 2017-04-04 | Dow Global Technologies Llc | Composite polyamide membrane with increased carboxylic acid functionality |
| US9289729B2 (en) | 2013-03-16 | 2016-03-22 | Dow Global Technologies Llc | Composite polyamide membrane derived from carboxylic acid containing acyl halide monomer |
| US9051417B2 (en) | 2013-03-16 | 2015-06-09 | Dow Global Technologies Llc | Method for solubilizing carboxylic acid-containing compound in hydrocarbon solvent |
| US9051227B2 (en) | 2013-03-16 | 2015-06-09 | Dow Global Technologies Llc | In-situ method for preparing hydrolyzed acyl halide compound |
| US9387442B2 (en) | 2013-05-03 | 2016-07-12 | Dow Global Technologies Llc | Composite polyamide membrane derived from an aliphatic acyclic tertiary amine compound |
| CN105873665B (zh) * | 2013-12-02 | 2019-01-01 | 陶氏环球技术有限责任公司 | 用亚硝酸后处理的复合聚酰胺膜 |
| EP3077089B1 (en) * | 2013-12-02 | 2018-02-28 | Dow Global Technologies LLC | Method of forming a composite polyamide membrane treated with dihyroxyaryl compounds and nitrous acid |
| CN105848758B (zh) * | 2014-01-07 | 2020-01-17 | 陶氏环球技术有限责任公司 | 使用防积垢反渗透膜从水性混合物分离烃 |
| KR102289354B1 (ko) * | 2014-01-09 | 2021-08-12 | 다우 글로벌 테크놀로지스 엘엘씨 | 높은 산 함량 및 낮은 아조 함량을 갖는 복합 폴리아미드 막 |
| ES2677994T3 (es) | 2014-01-09 | 2018-08-08 | Dow Global Technologies Llc | Membrana de poliamida de material compuesto con contenido azoico preferido |
| KR102273550B1 (ko) * | 2014-01-09 | 2021-07-07 | 다우 글로벌 테크놀로지스 엘엘씨 | 아조 함량 및 높은 산 함량을 갖는 복합 폴리아미드 막 |
| CN105899284A (zh) * | 2014-01-13 | 2016-08-24 | 陶氏环球技术有限责任公司 | 高溶胀性复合聚酰胺膜 |
| KR102343738B1 (ko) | 2014-04-28 | 2021-12-27 | 다우 글로벌 테크놀로지스 엘엘씨 | 아질산으로 후처리된 복합체 폴리아미드막 |
| KR102357884B1 (ko) | 2014-05-14 | 2022-02-03 | 다우 글로벌 테크놀로지스 엘엘씨 | 아질산으로 후-처리된 복합 폴리아미드 멤브레인 |
| US9943810B2 (en) | 2014-05-14 | 2018-04-17 | Dow Global Technologies Llc | Composite polyamide membrane post-treated with nitrous acid |
| ES2704238T3 (es) | 2014-05-14 | 2019-03-15 | Dow Global Technologies Llc | Membrana de poliamida de material compuesto sometida a tratamiento posterior con ácido nitroso |
| CN113351028A (zh) * | 2020-03-05 | 2021-09-07 | 中国石油化工股份有限公司 | 一种复合反渗透膜及其制备方法和应用 |
| CN111821861B (zh) * | 2020-08-21 | 2022-01-07 | 烟台大学 | 一种星型分子化合物制备高通量有机溶剂纳滤膜的方法 |
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| US20030116498A1 (en) | 2000-04-17 | 2003-06-26 | Mickols William E. | Composite membrane and method for making the same |
| US20100062156A1 (en) | 2008-04-15 | 2010-03-11 | NanoH+hu 2+l O, Inc. NanoH+hu 2+l O Inc. | Reverse Osmosis Membranes |
| US20110005997A1 (en) | 2008-04-15 | 2011-01-13 | NanoH2O Inc. | Hybrid tfc ro membranes with nitrogen additives |
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| US4259183A (en) | 1978-11-07 | 1981-03-31 | Midwest Research Institute | Reverse osmosis membrane |
| US4277344A (en) | 1979-02-22 | 1981-07-07 | Filmtec Corporation | Interfacially synthesized reverse osmosis membrane |
| JP2000117076A (ja) * | 1998-10-16 | 2000-04-25 | Toray Ind Inc | 複合半透膜およびその製造方法 |
| WO2000041800A1 (fr) * | 1999-01-14 | 2000-07-20 | Toray Industries, Inc. | Membrane semi-permeable composite, procede de fabrication et procede de purification d'eau a l'aide de cette membrane |
| US6280853B1 (en) | 1999-06-10 | 2001-08-28 | The Dow Chemical Company | Composite membrane with polyalkylene oxide modified polyamide surface |
| DE69940981D1 (de) | 1999-09-28 | 2009-07-23 | Toray Industries | Verfahren zur herstellung einer semipermeablen verbundmembran |
| US20070251883A1 (en) | 2006-04-28 | 2007-11-01 | Niu Q Jason | Reverse Osmosis Membrane with Branched Poly(Alkylene Oxide) Modified Antifouling Surface |
| CN101605592B (zh) | 2007-02-05 | 2011-10-12 | 陶氏环球技术公司 | 改性的聚酰胺膜 |
| CN105457508B (zh) * | 2008-04-15 | 2018-10-26 | 纳米水公司 | 混杂的纳米粒子tfc膜 |
| US7815987B2 (en) | 2008-12-04 | 2010-10-19 | Dow Global Technologies Inc. | Polyamide membrane with coating of polyalkylene oxide and polyacrylamide compounds |
| WO2011112351A1 (en) | 2010-03-10 | 2011-09-15 | Dow Global Technologies Llc | Polyamide membrane with a coating comprising polyalkylene oxide and acetophenone compounds |
-
2012
- 2012-09-14 IN IN2212CHN2014 patent/IN2014CN02212A/en unknown
- 2012-09-14 ES ES12769543.5T patent/ES2556832T3/es active Active
- 2012-09-14 CN CN201280045586.2A patent/CN103889563B/zh active Active
- 2012-09-14 EP EP12769543.5A patent/EP2760570B1/en active Active
- 2012-09-14 WO PCT/US2012/055271 patent/WO2013048765A1/en not_active Ceased
- 2012-09-14 KR KR1020147011507A patent/KR101946792B1/ko active Active
- 2012-09-14 JP JP2014533584A patent/JP6027124B2/ja active Active
-
2014
- 2014-03-18 IL IL231573A patent/IL231573B/en active IP Right Grant
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030116498A1 (en) | 2000-04-17 | 2003-06-26 | Mickols William E. | Composite membrane and method for making the same |
| US20100062156A1 (en) | 2008-04-15 | 2010-03-11 | NanoH+hu 2+l O, Inc. NanoH+hu 2+l O Inc. | Reverse Osmosis Membranes |
| US20110005997A1 (en) | 2008-04-15 | 2011-01-13 | NanoH2O Inc. | Hybrid tfc ro membranes with nitrogen additives |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20140079442A (ko) | 2014-06-26 |
| WO2013048765A1 (en) | 2013-04-04 |
| JP2014531979A (ja) | 2014-12-04 |
| IL231573B (en) | 2018-07-31 |
| IL231573A0 (en) | 2014-04-30 |
| JP6027124B2 (ja) | 2016-11-16 |
| CN103889563A (zh) | 2014-06-25 |
| EP2760570B1 (en) | 2015-10-21 |
| IN2014CN02212A (enExample) | 2015-06-12 |
| CN103889563B (zh) | 2017-03-29 |
| ES2556832T3 (es) | 2016-01-20 |
| EP2760570A1 (en) | 2014-08-06 |
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