KR20090081238A - 폴리아미드 역삼투 복합막 제조용 아민수용액 및 이를이용한 폴리아미드 역삼투 복합막의 제조방법 - Google Patents
폴리아미드 역삼투 복합막 제조용 아민수용액 및 이를이용한 폴리아미드 역삼투 복합막의 제조방법 Download PDFInfo
- Publication number
- KR20090081238A KR20090081238A KR1020080007211A KR20080007211A KR20090081238A KR 20090081238 A KR20090081238 A KR 20090081238A KR 1020080007211 A KR1020080007211 A KR 1020080007211A KR 20080007211 A KR20080007211 A KR 20080007211A KR 20090081238 A KR20090081238 A KR 20090081238A
- Authority
- KR
- South Korea
- Prior art keywords
- amine
- reverse osmosis
- composite membrane
- osmosis composite
- polyamide reverse
- Prior art date
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- 239000012528 membrane Substances 0.000 title claims abstract description 83
- 150000001412 amines Chemical class 0.000 title claims abstract description 70
- 238000001223 reverse osmosis Methods 0.000 title claims abstract description 62
- 239000002131 composite material Substances 0.000 title claims abstract description 54
- 229920002647 polyamide Polymers 0.000 title claims abstract description 54
- 239000004952 Polyamide Substances 0.000 title claims abstract description 53
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 41
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- -1 amine salt Chemical class 0.000 claims abstract description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000000243 solution Substances 0.000 claims abstract description 26
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 23
- 239000000654 additive Substances 0.000 claims abstract description 21
- 230000000996 additive effect Effects 0.000 claims abstract description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 17
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 150000001266 acyl halides Chemical class 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 17
- 238000012695 Interfacial polymerization Methods 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- JCQBSAXJJNQRNE-UHFFFAOYSA-M 6-(dimethylamino)hexyl-trimethylazanium chloride Chemical compound [Cl-].CN(CCCCCC[N+](C)(C)C)C JCQBSAXJJNQRNE-UHFFFAOYSA-M 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 150000004985 diamines Chemical class 0.000 claims description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 229920002492 poly(sulfone) Polymers 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 150000003335 secondary amines Chemical class 0.000 claims description 5
- KRHWKVIPQKPRMA-UHFFFAOYSA-M 6-(dimethylamino)hexyl-dimethyl-octylazanium chloride Chemical compound [Cl-].CN(CCCCCC[N+](C)(C)CCCCCCCC)C KRHWKVIPQKPRMA-UHFFFAOYSA-M 0.000 claims description 4
- RMYROXWNRKUCDK-UHFFFAOYSA-M 6-(dimethylamino)hexyl-ethyl-dimethylazanium chloride Chemical compound CC[N+](C)(C)CCCCCCN(C)C.[Cl-] RMYROXWNRKUCDK-UHFFFAOYSA-M 0.000 claims description 4
- JUENAHQOJPMJBW-UHFFFAOYSA-M 6-(dimethylamino)octyl-hexyl-dimethylazanium chloride Chemical compound [Cl-].CN(C(CCCCC[N+](C)(C)CCCCCC)CC)C JUENAHQOJPMJBW-UHFFFAOYSA-M 0.000 claims description 4
- LFKABHFCQULHFH-UHFFFAOYSA-M CCCCCCC(CCCCC[N+](C)(C)CCCCCC)N(C)C.[Cl-] Chemical compound CCCCCCC(CCCCC[N+](C)(C)CCCCCC)N(C)C.[Cl-] LFKABHFCQULHFH-UHFFFAOYSA-M 0.000 claims description 4
- XUPGUMTWAHFOGV-UHFFFAOYSA-M CCCCCC[N+](C)(C)CCCCCCN(C)C.[Cl-] Chemical compound CCCCCC[N+](C)(C)CCCCCCN(C)C.[Cl-] XUPGUMTWAHFOGV-UHFFFAOYSA-M 0.000 claims description 4
- IMNWDUWXGYZIHI-UHFFFAOYSA-M CCCC[N+](C)(C)CCCCCCN(C)C.[Cl-] Chemical compound CCCC[N+](C)(C)CCCCCCN(C)C.[Cl-] IMNWDUWXGYZIHI-UHFFFAOYSA-M 0.000 claims description 4
- USTGXOFFNTWXBC-UHFFFAOYSA-M CCC[N+](C)(C)CCCCCCN(C)C.[Cl-] Chemical compound CCC[N+](C)(C)CCCCCCN(C)C.[Cl-] USTGXOFFNTWXBC-UHFFFAOYSA-M 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000002033 PVDF binder Substances 0.000 claims description 3
- 239000004695 Polyether sulfone Substances 0.000 claims description 3
- 239000004642 Polyimide Substances 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- 229920006393 polyether sulfone Polymers 0.000 claims description 3
- 229920001721 polyimide Polymers 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 abstract description 29
- 239000012948 isocyanate Substances 0.000 abstract description 5
- 150000002513 isocyanates Chemical class 0.000 abstract description 5
- 230000000704 physical effect Effects 0.000 abstract description 4
- 150000003461 sulfonyl halides Chemical class 0.000 abstract description 4
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 19
- 125000003277 amino group Chemical group 0.000 description 11
- 239000010410 layer Substances 0.000 description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000010612 desalination reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 230000035699 permeability Effects 0.000 description 5
- 239000012466 permeate Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000013535 sea water Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000001345 alkine derivatives Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 230000003204 osmotic effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000005631 S-sulfonamido group Chemical group 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000008235 industrial water Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-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
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 description 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- JBGQIGKEDXHQND-UHFFFAOYSA-M [OH-].[NH4+].C(CC)[N+](CCC)(CCC)CCC.[OH-] Chemical compound [OH-].[NH4+].C(CC)[N+](CCC)(CCC)CCC.[OH-] JBGQIGKEDXHQND-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 description 1
- QEABVDWVSDSQRO-UHFFFAOYSA-M benzyl(tripropyl)azanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CC1=CC=CC=C1 QEABVDWVSDSQRO-UHFFFAOYSA-M 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- CCRKYXVCFWPPRY-UHFFFAOYSA-N cyclohex-2-ene-1,1-diamine Chemical class NC1(N)CCCC=C1 CCRKYXVCFWPPRY-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000005152 trihalomethanesulfonyl group Chemical group 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
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- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/025—Reverse osmosis; Hyperfiltration
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D67/0095—Drying
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D69/107—Organic support material
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
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- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/1213—Laminated layers
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- 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
- B01D71/26—Polyalkenes
- B01D71/262—Polypropylene
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- 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
- B01D71/30—Polyalkenyl halides
- B01D71/32—Polyalkenyl halides containing fluorine atoms
- B01D71/34—Polyvinylidene fluoride
-
- 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
- B01D71/58—Other polymers having nitrogen in the main chain, with or without oxygen or carbon only
- B01D71/62—Polycondensates having nitrogen-containing heterocyclic rings in the main chain
- B01D71/64—Polyimides; Polyamide-imides; Polyester-imides; Polyamide acids or similar polyimide precursors
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- B01D2323/21827—Salts
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Abstract
Description
아민염 첨가제 | 투과유속(gfd) | 염제거율(%) | |
실시예 1 | 0.2wt% 6-(디메틸아미노)헥실 트리메틸 암모늄 클로라이드 | 45.3 | 98.3 |
실시예 2 | 0.2wt% 6-(디메틸아미노)헥실 디메틸 에틸 암모늄 클로라이드 | 41.2 | 97.9 |
실시예 3 | 0.2wt% 6-(디메틸아미노)헥실 디메틸 부틸 암모늄 클로라이드 | 42.6 | 98.2 |
실시예 4 | 0.2wt% 6-(디메틸아미노)헥실 디메틸 헥실 암모늄 클로라이드 | 47.2 | 98.4 |
실시예 5 | 0.2wt% 6-(디메틸아미노)헥실 디메틸 옥틸 암모늄 클로라이드 | 46.2 | 98.2 |
실시예 6 | 0.2wt% 6-(디메틸아미노)메틸 디메틸 헥실 암모늄 클로라이드 | 48.4 | 98.7 |
실시예 7 | 0.2wt% 6-(디메틸아미노)프로필 디메틸 헥실 암모늄 클로라이드 | 43.2 | 98.1 |
실시예 8 | 0.2wt% 6-(디메틸아미노)옥틸 디메틸 헥실 암모늄 클로라이드 | 49.5 | 97.9 |
실시예 9 | 0.2wt% 6-(디메틸아미노)도데실 디메틸 헥실 암모늄 클로라이드 | 52.3 | 98.2 |
비교예 1 | 0.2wt% TMHD(,N,N',N'-테트라메틸-1,6-헥사디아민) | 39.8 | 96.9 |
비교예 2 | 0.2wt% TMHD + 0.22%wt% TSA (N,N,N',N'-테트라메틸헥산디아민 톨루엔술폰산) | 32.2 | 97.3 |
비교예 3 | 0.2wt%, 1,6-헥사 비스 트리메틸 암모늄 클로라이드 | 37.6 | 97.7 |
Claims (14)
- 다관능성 아민 0.1 ~ 20중량%, 임의적으로 치환된 탄화수소의 주쇄에 3급아민 및 4급아민을 모두 포함하는 아민염 첨가제 0.01 내지 10 중량% 및 물 70 내지 99.89 중량%를 포함하는 것을 특징으로 하는 폴리아미드 역삼투 복합막 제조용 아민수용액.
- 제1항에 있어서, 상기 다관능성 아민은 1급아민 또는 2급아민인 것을 특징으로 하는 상기 폴리아미드 역삼투 복합막 제조용 아민수용액.
- 제2항에 있어서, 상기 다관능성 아민은 방향족 1급 디아민, 사이클로지방족 1급 디아민, 사이클로지방족 2급아민 및 방향족 2급아민으로 구성되는 군으로부터 선택되는 어느 하나 이상의 아민인 것을 특징으로 하는 폴리아미드 역삼투 복합막 제조용 아민수용액.
- 제1항에 있어서, 상기 탄화수소는 C1 ~ 20 인 것을 특징으로 하는 폴리아미드 역삼투 복합막 제조용 아민수용액.
- 제1항에 있어서, 상기 아민염 첨가제는 주쇄에 1 ~ 6개의 3급아민 및 1 ~ 6 개의 4급아민을 포함하는 것을 특징으로 하는 폴리아미드 역삼투 복합막 제조용 아민수용액.
- 제1항에 있어서,상기 탄화수소는 지방족 탄화수소 또는 방향족 탄화수소인 것을 특징으로 하는 폴리아미드 역삼투 복합막 제조용 아민수용액.
- 제1항에 있어서,상기 아민염 첨가제는 6-(디메틸아미노)헥실 트리메틸 암모늄 클로라이드, 6-(디메틸아미노)헥실 디메틸 에틸 암모늄 클로라이드, 6-(디메틸아미노)헥실 디메틸 부틸 암모늄 클로라이드, 6-(디메틸아미노)헥실 디메틸 헥실 암모늄 클로라이드, 6-(디메틸아미노)헥실 디메틸 옥틸 암모늄 클로라이드, 6-(디메틸아미노)메틸 디메틸 헥실 암모늄 클로라이드, 6-(디메틸아미노)프로필 디메틸 헥실 암모늄 클로라이드, 6-(디메틸아미노)옥틸 디메틸 헥실 암모늄 클로라이드 및 6-(디메틸아미노)도데실 디메틸 헥실 암모늄 클로라이드로 구성되는 군으로부터 선택되는 어느 하나 이상인 것을 특징으로 하는 폴리아미드 역삼투 복합막 제조용 아민수용액.
- 아민수용액과 아민반응성 화합물을 계면중합하여 폴리아미드 역삼투 복합막을 제조하는 방법에 있어서,(a) 제1항 내지 제7항 중 어느 한 항의 아민수용액; 및(b) 다관능성 아실할라이드, 다관능성 술포닐할라이드 및 다관능성 이소시아네이트로 선택되는 군으로부터 선택되는 어느 하나 이상의 아민반응성 화합물 0.01 내지 5중량%를 함유하는 유기용액을 다공성 지지체 표면에 접촉시켜 계면중합으로 활성층을 형성하는 것을 특징으로 하는 폴리아미드 역삼투 복합막의 제조방법.
- 제8항에 있어서, 상기 아민 반응성 화합물은 트리메조일클로라이드(trimesoyl chloride), 테레프탈로일 클로라이드(terephthaloyl chloride) 및 이소프탈로일 클로라이드(isophthalolylchloride)로 이루어진 군으로부터 선택되는 어느 하나 이상인 것을 특징으로 하는 상기 폴리아미드 역삼투 복합막의 제조방법.
- 제8항에 있어서, 상기 아민수용액에 극성용매, 아민염 및 다관능성 3급아민 중 어느 하나 이상을 더 첨가하는 것을 특징으로 하는 상기 폴리아미드 역삼투 복합막의 제조방법.
- 제8항에 있어서, 상기 유기용액의 용매는 할로게네이티드 하이드로카본, 헥산, 사이클로헥산, 헵탄, C8 ~12 알칸으로 구성되는 군으로부터 선택되는 어느 하나 이상인 것을 특징으로 하는 상기 폴리아미드 역삼투 복합막의 제조방법.
- 제8항에 있어서, 상기 (b)단계 이후 얻어진 분리막을 18 ~ 50℃에서 30초 ~ 3분간 건조시킨 후 18 ~ 95℃의 염기수용액에서 1 ~ 30분간 침지하는 단계를 더 포함하는 것을 특징으로 하는 상기 폴리아미드 역삼투 복합막의 제조방법.
- 제8항에 있어서, 상기 다공성 지지체는 공경이 1~500nm이고 폴리설폰(Polysulfone), 폴리이써설폰(Polyethersulfone), 폴리이미드(Polyimide), 폴리프로필렌(Polupropylene)및 폴리비닐리덴플로라이드(Polyvinylidenefluoride) 중 어느 하나인 것을 특징으로 하는 상기 폴리아미드 역삼투 복합막의 제조방법.
- 제8항 내지 제13항 중 어느 한 항의 제조방법으로 제조된 폴리아미드 역삼투 복합막.
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