CN104470627B - 复合聚酰胺膜 - Google Patents
复合聚酰胺膜 Download PDFInfo
- Publication number
- CN104470627B CN104470627B CN201380038526.2A CN201380038526A CN104470627B CN 104470627 B CN104470627 B CN 104470627B CN 201380038526 A CN201380038526 A CN 201380038526A CN 104470627 B CN104470627 B CN 104470627B
- Authority
- CN
- China
- Prior art keywords
- carboxylic acid
- acid halides
- monomer
- multifunctional carboxylic
- chloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 239000012528 membrane Substances 0.000 title claims abstract description 20
- 239000004952 Polyamide Substances 0.000 title claims abstract description 16
- 239000002131 composite material Substances 0.000 title claims abstract description 16
- 229920002647 polyamide Polymers 0.000 title claims abstract description 16
- -1 carboxylic acid halides Chemical class 0.000 claims abstract description 70
- 239000000178 monomer Substances 0.000 claims abstract description 45
- 239000011248 coating agent Substances 0.000 claims abstract description 22
- 238000000576 coating method Methods 0.000 claims abstract description 22
- 150000001412 amines Chemical class 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000012695 Interfacial polymerization Methods 0.000 claims abstract description 12
- 239000010409 thin film Substances 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 150000001263 acyl chlorides Chemical class 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000010422 painting Methods 0.000 claims description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 claims description 3
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000010408 film Substances 0.000 abstract description 34
- 239000012454 non-polar solvent Substances 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 23
- 230000004907 flux Effects 0.000 description 14
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 12
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 11
- 229940018564 m-phenylenediamine Drugs 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000001223 reverse osmosis Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical class ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 description 2
- 238000010406 interfacial reaction Methods 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- NNIJZQYSYZQFDZ-UHFFFAOYSA-N (2,3-dibutylphenyl) dihydrogen phosphate Chemical compound CCCCC1=CC=CC(OP(O)(O)=O)=C1CCCC NNIJZQYSYZQFDZ-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
- 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
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical class NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-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
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 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
- 229920002125 Sokalan® Polymers 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000777 acyl halide group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JSYBAZQQYCNZJE-UHFFFAOYSA-N benzene-1,2,4-triamine Chemical class NC1=CC=C(N)C(N)=C1 JSYBAZQQYCNZJE-UHFFFAOYSA-N 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- RPHKINMPYFJSCF-UHFFFAOYSA-N benzene-1,3,5-triamine Chemical class NC1=CC(N)=CC(N)=C1 RPHKINMPYFJSCF-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 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
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 235000012489 doughnuts Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 150000002500 ions Chemical class 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
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 238000005259 measurement 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 239000002245 particle 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 239000002798 polar solvent Substances 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
- 238000006068 polycondensation reaction Methods 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
- 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
- 150000003141 primary amines Chemical class 0.000 description 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007592 spray painting technique Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 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
- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 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
-
- 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
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/025—Reverse osmosis; Hyperfiltration
-
- 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
-
- 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
- B01D69/10—Supported membranes; Membrane supports
- B01D69/107—Organic support material
-
- 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
- B01D69/1214—Chemically bonded layers, e.g. cross-linking
-
- 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
- B01D2323/219—Specific solvent system
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/38—Graft polymerization
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/20—Specific permeability or cut-off range
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Manufacturing & Machinery (AREA)
- Nanotechnology (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Polyamides (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Laminated Bodies (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
用于制造包含多孔载体和薄膜聚酰胺层的复合聚酰胺膜的方法，其中所述方法包括向多孔载体表面施加多官能胺单体和多官能酰卤单体并界面聚合所述单体以形成薄膜聚酰胺层的步骤，其中向所述多孔载体施加多官能酰卤单体的步骤包括将所述多官能酰卤单体与非极性溶剂以至少0.18重量％的浓度合并以形成涂层溶液的步骤，所述涂层溶液然后施加于所述多孔载体的表面，并且其中所述界面聚合在磷酸三烃基酯化合物存在下进行，所述磷酸三烃基酯化合物以与所述多官能酰卤单体为至少0.5:1的摩尔比提供。描述了许多其他的实施方式，包括由所述方法制成的膜和这种膜的应用。
Description
发明领域
本发明涉及复合膜及其制造和使用方法。
发明背景
复合聚酰胺膜用于各种流体分离。一种类别包括具有“薄膜”聚酰胺层的多孔载体。这些膜统称为“薄膜复合”(TFC)膜。所述薄膜层可以通过将多官能胺(例如间苯二胺)和多官能酰卤(例如均苯三甲酰氯)单体从不混溶溶液顺序涂布在载体上后二者之间界面缩聚反应而形成，参见例如Cadotte的US 4277344。为了改善膜性能，可以向涂层溶液之一或二者中添加各种成分。例如，Mickols的US 6878278描述了向所述酰卤涂层溶液添加磷酸三烃基酯化合物。
虽然改变胺和酰卤单体的相对量可影响膜性能，但增加与所述胺单体反应所需的多官能酰卤单体的量通常不会引起聚合期间消耗的酰卤单体的明显的相应增加。本发明人发现了这种现象的例外，其中聚合期间消耗的酰卤单体的量可增加，产生具有独特性质的膜。
发明内容
本发明包括薄膜复合膜及其制造和使用方法。在一种实施方式中，所述方法包括向多孔载体表面施加多官能胺单体和多官能酰卤单体并界面聚合所述单体以形成薄膜聚酰胺层的步骤。施加多官能酰卤的步骤包括将所述多官能酰卤单体与非极性溶剂以至少0.18重量％的浓度合并以形成涂层溶液，所述涂层溶液然后施加于所述多孔载体的表面的步骤。所述界面聚合在磷酸三烃基酯化合物存在下进行，所述磷酸三烃基酯化合物提供为与所述多官能酰卤单体的摩尔比率为至少0.5:1。根据本发明的优选实施方式，薄膜复合聚酰胺膜可以制备成具有较高的通量、更大的厚度(例如在一些实施方式中大于100nm)、或更大的厚度和较高的通量二者的膜。
附图说明
图1A的图对应于根据实施例1制备的膜，以均苯三甲酰氯反应物浓度随通量(gfd)的变化绘制。
图1B是对应于根据实施例1制备的样品膜的图，以均苯三甲酰氯反应物浓度随界面聚合期间TMC消耗量(mg/m2)的变化绘制。
图2A是对应于根据实施例2制备的样品膜的图，以磷酸三丁酯浓度随通量(gfd)变化绘制。
图2B是对应于根据实施例2制备的样品膜的图，以磷酸三丁酯浓度随界面聚合期间均苯三甲酰氯消耗量(mg/m2)的变化绘制。
发明具体描述
本发明包括复合膜及其制造和使用方法。本发明不具体限于特定类型、构造或形状的复合膜或应用。例如，本发明适用于可用于各种应用包括正渗透(FO)、反渗透(RO)和纳滤(NF)的平板状、管状和中空纤维聚酰胺膜。RO复合膜对于几乎所有的溶解盐相对不可渗透，并通常截留超过大约95％的单价离子盐，例如氯化钠。RO复合膜还通常截留超过大约95％的无机分子以及分子量大于约100道尔顿的有机分子。NF复合膜比RO复合膜更可渗透，并通常截留小于约95％的单价离子盐，同时根据二价离子的种类，截留超过约50％(并经常超过90％)的二价离子盐。NF复合膜还通常截留纳米范围的粒子以及分子量大于约200至500道尔顿的有机分子。
本方法包括在多孔载体上形成薄膜聚酰胺层。所述多孔载体没有特别的限制并优选包括聚合材料，所述聚合材料具有的孔隙尺寸足以允许渗透物基本上不受限制地通过，然而并非大得足以妨碍在其上形成的薄膜聚酰胺膜层的桥接。例如，所述载体的孔隙尺寸优选从大约0.001至0.5μm。多孔载体的非限制性例子包括由下列材料制成的那些：聚砜，聚醚砜，聚酰亚胺，聚酰胺，聚醚酰亚胺，聚丙烯腈，聚(甲基丙烯酸甲酯)，聚乙烯，聚丙烯，和各种卤化聚合物例如聚偏氟乙烯。
所述薄膜聚酰胺层优选通过在多孔载体表面上，多官能胺单体和多官能酰卤单体之间的界面缩聚反应而制备，如US 4277344和US6878278所述。更具体地说，可以通过多官能胺单体与多官能酰卤单体(其中每个术语意图是指利用单种物质或多种物质两者)在多孔载体的至少一个表面上进行界面聚合来制备所述聚酰胺膜。术语“聚酰胺”是指沿着分子链存在酰胺键(—C(O)NH—)的聚合物。所述多官能胺和多官能酰卤单体最通常通过从溶液进行涂布的步骤施加于多孔载体，其中所述多官能胺单体优选从水基或极性涂层溶液涂布，而多官能胺酰卤从有机基或非极性涂层溶液涂布。虽然涂布步骤不需要按照特定的次序，但优选在所述多孔载体上首先涂布多官能胺单体，然后是多官能酰卤。涂布可通过喷涂、膜涂、辊涂或通过使用浸渍槽以及其他涂布技术完成。多余的溶液可以通过气刀、干燥器、烘箱等等从所述载体上除去。一旦彼此发生接触，所述多官能酰卤单体和多官能胺单体在它们的表面处界面反应，形成聚酰胺层或膜。这种层，经常被称为聚酰胺“辨别层”或“薄膜层”，提供了具有从溶剂(例如水性进料)中分离溶质(例如盐)的主要手段的复合膜。所述多官能酰卤单体与多官能胺单体的反应时间可以小于一秒，但是接触时间通常在约1至60秒，之后可以任选通过气刀、水浴、干燥器等除去多余的液体。除去多余的溶液可以通过在升高的温度下、例如约40℃至约120℃下干燥来完成，但是也可以利用在环境温度下空气干燥。
所述多官能胺单体包含至少两个伯或仲氨基，并且可以是芳族的(例如间苯二胺、对苯二胺、1,3,5-三氨基苯、1,3,4-三氨基苯、3,5-二氨基苯甲酸、2,4-二氨基甲苯、2,4-二氨基茴香醚、和二甲苯二胺)或脂族的(例如乙二胺、丙二胺和三(2-二氨基乙基)胺)。优选的多官能胺单体的例子包括具有两个或三个氨基的伯胺，例如间苯二胺，和具有两个氨基的脂族仲胺，例如哌嗪。一种优选的多官能胺是间苯二胺(mPD)。多官能胺单体可以作为包含极性溶液的涂层溶液的一部分施加于多孔载体。所述极性涂层溶液可以含有约0.1至约20重量％并更优选约0.5至约6重量％的多官能胺单体。一旦涂布在多孔载体上，可以任选除去多余的涂层溶液。
所述多官能酰卤单体包含至少两个酰卤基团。所述多官能酰卤没有特别限制，可以使用芳族或脂环族的多官能酰卤及其组合。芳族多官能酰卤的非限制性例子包括：均苯三甲酰氯，对苯二甲酰氯，间苯二甲酰氯，联苯基二羧酰氯，苯四羧酰氯，5,5’-亚甲基二间苯二甲酰氯，联苯基四羧酰氯和萘二羧酰氯。脂环族多官能酰卤的非限制性例子包括：环丙烷三羧酰氯，环丁烷四羧酰氯，环戊烷三羧酰氯，环戊烷四羧酰氯，环己烷三羧酰氯，四氢呋喃四羧酰氯，环戊烷二羧酰氯，环丁烷二羧酰氯，环己烷二羧酰氯，和四氢呋喃二羧酰氯。一种优选的多官能酰卤是均苯三甲酰氯(TMC)。所述多官能酰卤优选从包含浓度为至少0.18、0.20、0.22、0.24、0.26、0.28或甚至0.30重量％的溶解在非极性溶剂中的多官能酰卤的涂层溶液施加于所述多孔载体。优选的浓度范围包括：0.18至4重量％，0.20至3重量％，0.22至2重量％，和0.24至1重量％。所述涂层溶液可以作为连续或分批涂布操作的一部分施加于多孔载体。合适的非极性溶剂是能够溶解所述多官能酰卤并且与水不混溶的那些，例如己烷、环己烷、庚烷和卤代烃例如FREON系列。优选的溶剂包括对臭氧层造成很小威胁并在经历常规加工时闪点和可燃性方面足够安全而不需要采取特殊防范的溶剂。优选的溶剂是ISOPARTM，可得自Exxon Chemical Company。所述涂层溶液可以任选包含其它物质，包括共溶剂、相转移剂、增溶剂和络合剂，其中单个添加剂可以起到多种功能。代表性的共溶剂包括：苯，甲苯，二甲苯，均三甲苯，乙苯，二乙二醇二甲醚，环己酮，乙酸乙酯，丁基卡必醇TM乙酸酯，月桂酸甲酯和丙酮。
本方法包括在磷酸三烃基酯化合物存在下进行前述界面聚合的步骤。向多孔载体施加所述磷酸三烃基酯化合物的手段没有特别的限制，例如所述磷酸三烃基酯化合物可以包含在前述的涂层溶液之一或二者中，或者可以在界面聚合之前或期间从单独的涂层溶液涂布。在优选实施方式中，所述磷酸三烃基酯化合物添加到用于向多孔载体施加所述多官能酰卤的涂层溶液中。
在优选实施方式中，所述磷酸三烃基酯化合物在界面聚合期间与所述多官能酰卤以至少0.25:1、0.5:1、1:1、1.5:1或2:1的摩尔比存在。
可适用的磷酸三烃基酯化合物的代表性例子在US 6878278中描述。这种化合物的优选类别包括式(I)表示的那些。
式(I)：
其中“P”是磷，“O”是氧，R1、R2和R3独立地选自氢和包含1至10个碳原子的烃基，条件是R1、R2和R3中不超过一个是氢。R1、R2和R3优选独立地选自脂族和芳族基团。可适用的脂族基团包括支链和非支链的物质二者，例如甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、2-戊基、3-戊基。可适用的环状基团包括环戊基和环己基。可适用的芳族基团包括苯基和萘基。环状和芳族基团可以通过脂族连接基团例如甲基、乙基等与磷原子相连。前述的脂族和芳族基团可以是未取代的或取代的(例如用甲基、乙基、丙基、羟基、酰胺、醚、砜、羰基、酯、氰化物、腈、异氰酸酯、氨基甲酸酯、β-羟基酯等取代)；然而，优选具有3至10个碳原子的未取代烷基。磷酸三烃基酯化合物的具体例子包括：磷酸三丙酯，磷酸三丁酯，磷酸三戊酯，磷酸三己酯，磷酸三苯酯，磷酸丙基二苯基酯，磷酸二丁基苯基酯，磷酸丁基二乙基酯，磷酸氢二丁基酯，磷酸氢丁基庚基酯和磷酸丁基庚基己基酯。
本发明的发明人已经发现，在磷酸三烃基酯化合物存在下进行前述的界面聚合允许增加在界面聚合期间消耗的多官能酰卤单体的量，产生水通量提高的不同的聚合物结构。这种技术效果的所有益处仅仅当使用至少0.18wt％的多官能酰卤单体浓度并且磷酸三烃基酯化合物与所述酰卤单体的摩尔比为至少0.5:1和到至少0.25:1的较小程度时才被观察到。本发明允许制备具有通量增加、厚度更大(例如超过100nm)的薄膜复合聚酰胺膜，并且在优选实施方式中，兼具较厚并且通量较高的膜。较厚的膜提供了改善的机械强度、耐化学性和防垢性质。较厚和通量较高相结合的膜是特别令人惊讶的。
所述薄膜聚酰胺层可以任选在它的表面的至少一部分上包含吸湿性聚合物。这样的聚合物包括聚合表面活性剂、聚丙烯酸、聚乙酸乙烯酯、聚环氧烷化合物、聚(噁唑啉)化合物、聚丙烯酰胺和相关的反应产物，如US 6280853、US 7815987、US 7882963、US 7918349和US 8002120和US 2011/0284458中的一般性描述。在一些实施方式中，这样的聚合物可以掺合和/或反应，并可以涂布或以其它方式从共同的溶液施加于所述聚酰胺膜，或相继施加。
已经描述了本发明的许多实施方式，并且在一些情况下，某些实施方式、选择、范围、成分或其他特征已经被表征为“优选的”。“优选”特征的表征决不能被解释为认为这样的特征是本发明要求的、必需的或关键的。
实施例
样品膜利用中试规模膜生产线制造。聚砜载体从在二甲基甲酰胺(DMF)中的16.5wt％溶液浇铸，随后浸泡在间苯二胺(mPD)水溶液中。然后将所生成的载体恒速牵拉通过反应台，同时施加非极性溶液的均匀薄层。所述非极性溶液包含异链烷油(ISOPAR L)、均苯三甲酰氯(TMC)、和在选定的实施例中，磷酸三丁酯(TBP)。除去多余的非极性溶液，所生成的复合膜通过水清洗槽和干燥炉。MPD、TMC和TBP的浓度根据如下文指示变化。在所述聚酰胺界面反应期间消耗的TMC的量通过比较样品进料的TMC浓度(通过297nm处紫外-可见光吸光度测量)与聚合完成之后Isopar L反应池的最终浓度来测量。TMC的这种转化通过测量施加于膜表面的Isopar L的量折算成TMC消耗。消耗值以每平方米膜的TMC的mg单位数报告。样品膜的试件利用盐水溶液(2000ppm NaCl)在150psi、PH 8和25℃下进行标准测试。
实施例1
为了强调本发明，制备了四个系列的样品膜，每个系列包括利用不同的TMC量(即0.09至0.52wt％)制成的样品。每个系列的其余反应物组成列举在下面表1中以及在图1A-B中使用的相应图标。测定每个样品的获得的通量(GFD)和“TMC消耗量”(mg/m2)，结果分别在图1A和B中随TMC浓度(wt％)的变化绘图。在较低的TMC浓度下，四条曲线全部显示类似的TMC消耗和通量值。然而，随着TMC浓度增加，所述系列之间出现差异。更具体地说，包含TBP与TMC摩尔比为1.1:1的样品(系列4)随着TMC反应物浓度增加显示出通量和TMC消耗量二者显著增加；而不用TBP制成的样品膜经历通量降低并且
TMC消耗量只显示中度改变。
实施例2
制备两个系列(即系列5和6)的样品膜，每个系列包括利用不同量的TBP(即大约0至4g/kg)制成的样品。每个系列的其余反应物组成列举在下面表1中以及也用于图2A-B中的相应图标。测定每个样品的获得的通量(gfd)和“TMC消耗量”(mg/m2)，结果分别在图2A和2B中随着TBP浓度(g/kg)的变化绘图。在较低的TMC浓度下(系列5)，虽然TBP浓度改变，但通量和TMC消耗量保持相对不变。然而，在较高的浓度下(系列)，通量和TMC消耗量二者随着TBP浓度增加而增加。
表1:
Claims (6)
1.用于制造包含多孔载体和薄膜聚酰胺层的复合聚酰胺膜的方法，其中所述方法包括向多孔载体的表面施加包含0.1至20重量％的多官能胺单体的水基溶液和包含0.18至0.39重量％的多官能酰卤单体的有机基溶液并界面聚合所述单体以形成薄膜聚酰胺层的步骤，
其中所述界面聚合在磷酸三烃基酯化合物存在下进行，所述磷酸三烃基酯化合物以与所述多官能酰卤单体为至少0.5:1的摩尔比提供，并且
其中所述磷酸三烃基酯化合物由式(I)表示：
式(I):
其中R1、R2和R3独立地选自氢和包含1至10个碳原子的烃基，条件是R1、R2和R3中不超过一个是氢；
其中所述多官能酰卤单体选自均苯三甲酰氯、对苯二甲酰氯、间苯二甲酰氯、联苯基二羧酰氯、苯四羧酰氯、5,5’-亚甲基二间苯二甲酰氯、联苯基四羧酰氯、萘二羧酰氯、环丙烷三羧酰氯、环丁烷四羧酰氯、环戊烷三羧酰氯、环戊烷四羧酰氯、环己烷三羧酰氯、四氢呋喃四羧酰氯、环戊烷二羧酰氯、环丁烷二羧酰氯、环己烷二羧酰氯、四氢呋喃二羧酰氯和其组合。
2.权利要求1的方法，其中所述多官能酰卤单体和磷酸三烃基酯化合物合并在单一涂层溶液内，所述涂层溶液施加于所述多孔载体的表面。
3.权利要求2的方法，其中所述磷酸三烃基酯化合物与多官能酰卤单体以至少1:1的摩尔比提供在所述涂层溶液中。
4.权利要求1的方法，其中所述多官能酰卤单体以0.24至0.39重量％的浓度存在于所述有机基溶液中。
5.权利要求1的方法，其中所述R1、R2和R3独立地选自包含3至10个碳原子的烷基。
6.权利要求1的方法，其中所述多官能酰卤单体以0.20至0.30重量％的浓度存在于所述有机基溶液中。
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| PCT/US2013/049177 WO2014014663A1 (en) | 2012-07-19 | 2013-07-03 | Composite polyamide membrane |
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