JP4656503B2 - 複合半透膜及びその製造方法 - Google Patents
複合半透膜及びその製造方法 Download PDFInfo
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- JP4656503B2 JP4656503B2 JP2005094604A JP2005094604A JP4656503B2 JP 4656503 B2 JP4656503 B2 JP 4656503B2 JP 2005094604 A JP2005094604 A JP 2005094604A JP 2005094604 A JP2005094604 A JP 2005094604A JP 4656503 B2 JP4656503 B2 JP 4656503B2
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- Prior art keywords
- semipermeable membrane
- composite semipermeable
- membrane
- porous support
- treatment
- Prior art date
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- BZFATHSFIGBGOT-UHFFFAOYSA-N butane-1,1,1-tricarbonyl chloride Chemical compound CCCC(C(Cl)=O)(C(Cl)=O)C(Cl)=O BZFATHSFIGBGOT-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229960005069 calcium Drugs 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000013921 calcium diglutamate Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 description 1
- 239000001527 calcium lactate Substances 0.000 description 1
- 235000011086 calcium lactate Nutrition 0.000 description 1
- 229960002401 calcium lactate Drugs 0.000 description 1
- UMVAYAXXQSFULN-QHTZZOMLSA-L calcium;(2s)-2-aminopentanedioate;hydron Chemical compound [Ca+2].[O-]C(=O)[C@@H](N)CCC(O)=O.[O-]C(=O)[C@@H](N)CCC(O)=O UMVAYAXXQSFULN-QHTZZOMLSA-L 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst 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
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 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
- 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
- 238000010612 desalination reaction Methods 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- MHJAJDCZWVHCPF-UHFFFAOYSA-L dimagnesium phosphate Chemical compound [Mg+2].OP([O-])([O-])=O MHJAJDCZWVHCPF-UHFFFAOYSA-L 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 0.000 description 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000013918 magnesium diglutamate Nutrition 0.000 description 1
- 229940063886 magnesium glutamate Drugs 0.000 description 1
- OVGXLJDWSLQDRT-UHFFFAOYSA-L magnesium lactate Chemical compound [Mg+2].CC(O)C([O-])=O.CC(O)C([O-])=O OVGXLJDWSLQDRT-UHFFFAOYSA-L 0.000 description 1
- 239000000626 magnesium lactate Substances 0.000 description 1
- 235000015229 magnesium lactate Nutrition 0.000 description 1
- 229960004658 magnesium lactate Drugs 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 229910000400 magnesium phosphate tribasic Inorganic materials 0.000 description 1
- MYUGVHJLXONYNC-QHTZZOMLSA-J magnesium;(2s)-2-aminopentanedioate Chemical compound [Mg+2].[O-]C(=O)[C@@H](N)CCC([O-])=O.[O-]C(=O)[C@@H](N)CCC([O-])=O MYUGVHJLXONYNC-QHTZZOMLSA-J 0.000 description 1
- QQFLQYOOQVLGTQ-UHFFFAOYSA-L magnesium;dihydrogen phosphate Chemical compound [Mg+2].OP(O)([O-])=O.OP(O)([O-])=O QQFLQYOOQVLGTQ-UHFFFAOYSA-L 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000013919 monopotassium glutamate Nutrition 0.000 description 1
- 235000013923 monosodium glutamate Nutrition 0.000 description 1
- OCIDXARMXNJACB-UHFFFAOYSA-N n'-phenylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=C1 OCIDXARMXNJACB-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
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 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
- 239000003973 paint Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- MTAAPVANJNSBGV-UHFFFAOYSA-N pentane-1,1,1-tricarbonyl chloride Chemical compound CCCCC(C(Cl)=O)(C(Cl)=O)C(Cl)=O MTAAPVANJNSBGV-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- GHAIYFTVRRTBNG-UHFFFAOYSA-N piperazin-1-ylmethanamine Chemical compound NCN1CCNCC1 GHAIYFTVRRTBNG-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229960004109 potassium acetate Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 description 1
- 239000001521 potassium lactate Substances 0.000 description 1
- 235000011085 potassium lactate Nutrition 0.000 description 1
- 229960001304 potassium lactate Drugs 0.000 description 1
- ONQDVAFWWYYXHM-UHFFFAOYSA-M potassium lauryl sulfate Chemical compound [K+].CCCCCCCCCCCCOS([O-])(=O)=O ONQDVAFWWYYXHM-UHFFFAOYSA-M 0.000 description 1
- 229940116985 potassium lauryl sulfate Drugs 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- VLRIRAGKJXODNO-UHFFFAOYSA-N propane-1,1,1-tricarbonyl chloride Chemical compound CCC(C(Cl)=O)(C(Cl)=O)C(Cl)=O VLRIRAGKJXODNO-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 229940083542 sodium Drugs 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940083575 sodium dodecyl sulfate Drugs 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 229940073490 sodium glutamate Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000002344 surface layer 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000002759 woven fabric 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
- B01D69/10—Supported membranes; Membrane supports
- B01D69/105—Support pretreatment
-
- 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
-
- 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
- B01D67/0088—Physical treatment with compounds, e.g. swelling, coating or impregnation
-
- 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
- B01D67/0095—Drying
-
- 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
- B01D67/0097—Storing or preservation
-
- 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
- B01D69/02—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor characterised by their properties
-
- 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
- B01D69/1213—Laminated layers
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/06—Specific viscosities of materials involved
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/50—Control of the membrane preparation process
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)
Description
また、多官能酸ハライド成分の少なくとも一部に3価以上の多官能酸ハライドを用いて、架橋構造を形成するのが好ましい。
また、前記水溶性有機物質の表面張力は膜内への浸透性の観点から0.04N/m以下であることが好ましく、さらに好ましくは0.02〜0.035N/mである。表面張力が0.04N/mを超える場合には、膜内への浸透性が低くなるため未反応多官能アミン成分の除去効果が十分に得られない傾向にある。ただし、表面張力が0.04N/mを超える水溶性有機物質であっても、表面張力0.04N/m以下の水溶性有機物質に対して少量使用する場合には、膜の膨潤化を促進して洗浄効果を高める場合がある。例えば、エタノール(表面張力:0.022N/m)を50重量%含有する水溶液と、エタノールを40重量%及びジエチレングリコール(表面張力:0.045N/m)を10重量%含有する水溶液では、後者を用いた方が未反応多官能アミン成分を効率よく除去することができる。上記において、ジエチレングリコールの代わりにグリセリン(表面張力:0.063N/m)を用いた場合も同様である。表面張力0.04N/mを超える水溶性有機物質の添加量は、用いる水溶性有機物質の表面張力によって変わるが、通常表面張力0.04N/m以下の水溶性有機物質100重量部に対して50重量部以下であることが好ましく、さらに好ましくは30重量部以下である。
(透過流束及び塩阻止率の測定)
作製した平膜状の複合半透膜を所定の形状、サイズに切断し、平膜評価用のセルにセットする。約1500mg/LのNaClを含みかつNaOHを用いてpH6.5〜7.5に調整した水溶液を25℃で膜の供給側と透過側に1.5MPaの差圧を与えて膜に接触させる。この操作によって得られた透過水の透過速度および電導度を測定し、透過流束(m3/m2・d)および塩阻止率(%)を算出した。塩阻止率は、NaCl濃度と水溶液電導度の相関(検量線)を事前に作成し、それらを用いて下式により算出した。
(多官能アミン成分の多孔性支持体中での移動速度測定)
使用する多孔性支持体の片面にアミン水溶液を常圧で接触させ、他面に純水を常圧で接触させた。この操作により純水側は接触してから一定時間経過後にアミンが検出されはじめ、その後時間の経過とともにその濃度が増加する。時間に対する濃度の傾きが安定したところでその傾きをアミン成分の移動速度(mg/m2・sec)と定義した。純水側のアミン成分の濃度測定は、紫外可視分光光度計“UV−2450”(島津製作所製)を用いておこなった。
アミン水溶液の粘度は、BL型粘度計(東京計器製)を用いて測定した。
多孔性支持体の含水量は、所定面積の支持体サンプルを所定温度で乾燥させ、その前後の重量変化から算出した。
エタノール50重量%を含有する水溶液(25℃)中に、実施例及び比較例で作製した膜洗浄処理前の複合半透膜(φ25mm)を浸漬し、約8時間静置して複合半透膜中の未反応多官能アミン成分を抽出した。得られた抽出液の210nmでのUV吸光度を測定した。一方、50重量%エタノール水溶液中の多官能アミン成分の濃度と、その水溶液の210nm吸光度との相関(検量線)を事前に作成し、それらを用いて膜洗浄処理前の複合半透膜中に含まれる未反応多官能アミン成分の量を測定した。また、膜洗浄処理後の複合半透膜(φ25mm)を用い、上記と同様の方法で未反応多官能アミン成分の含有量を測定した。その結果を表1〜3に示す。
(多孔性支持体の作製)
ポリスルホン(Solvay社製、P−3500)18重量%をN,N−ジメチルホルムアミド(DMF)に溶解した製膜ドープを不織布基材上にウエット厚み200μmで均一に塗布した。その後、すぐに40〜50℃の水中に浸漬させることにより凝固させ、かつ溶媒であるDMFを完全に抽出洗浄することによって、不織布基材上にポリスルホン微多孔層を有する多孔性支持体を作製した。
作製した多孔性支持体を40℃で加熱乾燥させた。加熱乾燥後の多孔性支持体中の含水量は1g/m2であった。
表1に記載のように、多孔性支持体の乾燥温度、アミン水溶液の組成を変えた以外は実施例1と同様の方法で複合半透膜を作製し、透過試験を行った。透過試験の結果を表1に示す。
多孔性支持体に乾燥処理を行わず、アミン水溶液の組成を変えた以外は実施例1と同様の方法で複合半透膜を作製し、透過試験を行った。透過試験の結果を表1に示す。未反応多官能アミン成分の含有量が多いため実用性を満足しない。
多孔性支持体に乾燥処理を行わず、アミン水溶液の組成を変えた以外は実施例1と同様の方法で複合半透膜を作製し、透過試験を行った。透過試験の結果を表1に示す。未反応多官能アミン成分の含有量が非常に多いため実用性を満足しない。
作製した多孔性支持体を室温で風乾させた。乾燥後の多孔性支持体中の含水量は1g/m2であった。
m−フェニレンジアミン1.5重量%、トリエチルアミン4重量%、及びカンファースルホン酸8重量%を含有するアミン水溶液(アミン成分の移動速度:0.03mg/m2・sec)を用いた以外は実施例16と同様の方法で複合半透膜を作製し、透過試験を行った。透過試験の結果を表1に示す。
多孔性支持体の含水量を30g/m2、m−フェニレンジアミン3重量%、トリエチルアミン3重量%、カンファースルホン酸6重量%、及びラウリル硫酸ナトリウム0.15重量%を含有するアミン水溶液(アミン成分の移動速度:2.7mg/m2・sec)を用いた以外は実施例16と同様の方法で複合半透膜を作製し、透過試験を行った。透過試験の結果を表1に示す。未反応多官能アミン成分の含有量が非常に多いため実用性を満足しない。
作製した多孔性支持体を60℃で加熱乾燥させた。加熱乾燥後の多孔性支持体中の含水量は1g/m2であった。
表2に記載のように、多孔性支持体の含水量、アミン水溶液の組成を変えた以外は実施例18と同様の方法で複合半透膜を作製し、透過試験を行った。透過試験の結果を表2に示す。
作製した多孔性支持体を室温で風乾させた。乾燥後の多孔性支持体中の含水量は1g/m2であった。
表3に記載のように、エチレングリコールの添加量を変えた以外は実施例23と同様の方法で複合半透膜を作製し、透過試験を行った。透過試験の結果を表3に示す。
実施例1で作製した洗浄済の複合半透膜を25℃の酢酸ナトリウム水溶液(濃度:1重量%)中に10分間浸漬させることにより保湿複合半透膜を作製した。その後、保湿複合半透膜を120℃で10分間乾燥させることにより乾燥複合半透膜を作製した。透過試験の結果を表4に示す。
表4に記載の条件で、実施例26と同様の方法で乾燥複合半透膜を作製した。透過試験の結果を表4に示す。
実施例1と同様の方法で作製した未洗浄複合半透膜を、50℃の純水に酢酸ナトリウムを添加した酢酸ナトリウム水溶液(濃度:1重量%)中に10分間浸漬させることにより、洗浄及び保湿処理を同時に施して保湿複合半透膜を作製した。その後、保湿複合半透膜を120℃で10分間乾燥させることにより乾燥複合半透膜を作製した。透過試験の結果を表4に示す。
表4に記載の条件で、実施例45と同様の方法で乾燥複合半透膜を作製した。透過試験の結果を表4に示す。
実施例1と同様の方法で洗浄済複合半透膜を作製した。その後、保湿処理を施すことなく洗浄済複合半透膜を120℃で2分間乾燥させることにより乾燥複合半透膜を作製した。透過試験の結果を表4に示す。
Claims (12)
- 多官能アミン成分と多官能酸ハライド成分とを界面重合してなるポリアミド系樹脂を含むスキン層を多孔性支持体の表面に形成してなる複合半透膜の製造方法において、多官能アミン成分を含むアミン水溶液からなる水溶液被覆層を多孔性支持体上に形成する前に多孔性支持体にアミン不浸透処理を施す工程、及びスキン層の形成後に未反応多官能アミン成分の含有量を20mg/m2以下にする膜洗浄処理工程を含み、
前記アミン不浸透処理は、多孔性支持体中の含水量を20g/m 2 以下に減らす処理であることを特徴とする複合半透膜の製造方法。 - スキン層の形成後、膜洗浄処理前における未反応多官能アミン成分の含有量が200mg/m2以下である請求項1記載の複合半透膜の製造方法。
- アミン水溶液の粘度が7mPa・s以上である請求項1又は2記載の複合半透膜の製造方法。
- アミン水溶液は、多孔性支持体に常圧で接触させた際の多官能アミン成分の多孔性支持体中での移動速度が0.3mg/m2・sec以下のものである請求項1〜3のいずれかに記載の複合半透膜の製造方法。
- 多孔性支持体上に供給される多官能アミン成分の量が200〜600mg/m2になるようにアミン水溶液を塗布する工程を含む請求項1〜4のいずれかに記載の複合半透膜の製造方法。
- 膜洗浄処理工程後に、洗浄処理した膜に保湿処理を施す保湿工程、及び保湿処理を施した膜を乾燥する乾燥工程を含む請求項1〜5のいずれかに記載の複合半透膜の製造方法。
- 膜洗浄処理工程は、洗浄処理と同時に保湿処理を施す工程であり、さらに洗浄保湿処理を施した膜を乾燥する乾燥工程を含む請求項1〜5のいずれかに記載の複合半透膜の製造方法。
- 保湿処理において使用する保湿剤が、有機酸金属塩及び/又は無機酸金属塩である請求項6又は7記載の複合半透膜の製造方法。
- 有機酸金属塩が、酢酸アルカリ金属塩、乳酸アルカリ金属塩、及びグルタミン酸アルカリ金属塩からなる群より選択される少なくとも1種の有機酸アルカリ金属塩である請求項8記載の複合半透膜の製造方法。
- 無機酸金属塩が、炭酸水素アルカリ金属塩、リン酸一水素二アルカリ金属塩、リン酸二水素一アルカリ金属塩からなる群より選択される少なくとも1種の無機酸アルカリ金属塩である請求項8記載の複合半透膜の製造方法。
- アルカリ金属が、ナトリウム又はカリウムである請求項9又は10記載の複合半透膜の製造方法。
- 請求項1〜11のいずれかに記載の製造方法によって得られる複合半透膜。
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US11/664,428 US20080053893A1 (en) | 2004-10-01 | 2005-09-09 | Semipermeable Composite Membrane and Process for Producing the Same |
EP05781966A EP1825905A4 (en) | 2004-10-01 | 2005-09-09 | SEMI-PERMEABLE COMPOSITE MEMBRANE AND PROCESS FOR PRODUCTION OF SAID MEMBRANE |
PCT/JP2005/016617 WO2006038425A1 (ja) | 2004-10-01 | 2005-09-09 | 複合半透膜及びその製造方法 |
KR1020077009884A KR100969049B1 (ko) | 2004-10-01 | 2005-09-09 | 복합 반투막 및 그의 제조 방법 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4656502B2 (ja) * | 2004-10-01 | 2011-03-23 | 日東電工株式会社 | 複合半透膜及びその製造方法 |
JP4656503B2 (ja) * | 2004-10-01 | 2011-03-23 | 日東電工株式会社 | 複合半透膜及びその製造方法 |
JP4656511B2 (ja) * | 2004-10-04 | 2011-03-23 | 日東電工株式会社 | 複合逆浸透膜の製造方法 |
JP4936438B2 (ja) * | 2006-10-10 | 2012-05-23 | 日東電工株式会社 | 乾燥複合半透膜の製造方法 |
JP2008093544A (ja) * | 2006-10-10 | 2008-04-24 | Nitto Denko Corp | 複合半透膜及びその製造方法 |
JP2008246419A (ja) * | 2007-03-30 | 2008-10-16 | Nitto Denko Corp | 複合半透膜の製造方法 |
DE102009022513A1 (de) * | 2009-05-25 | 2010-12-02 | Qiagen Gmbh | Verfahren zum Schutz von Membranen |
US9056284B2 (en) * | 2012-08-10 | 2015-06-16 | The United States Of America, As Represented By The Secretary Of The Interior | Chlorine resistant amides, polyamides, and membranes made from the same |
US20140263024A1 (en) * | 2013-03-14 | 2014-09-18 | Andrew Patrick MURPHY | Halogen resistant amides, polyamides, and membranes made from the same |
CN107376667B (zh) * | 2017-08-25 | 2020-11-27 | 上海城市水资源开发利用国家工程中心有限公司 | 一种制备纳滤/正渗透两栖性能cta膜的方法及装置 |
KR102280869B1 (ko) * | 2018-10-12 | 2021-07-22 | 주식회사 엘지화학 | 수처리 분리막의 제조 방법 및 이에 의하여 제조된 수처리 분리막 |
CN111841346B (zh) * | 2020-07-21 | 2023-04-14 | 浙江奥氏环境科技有限公司 | 一种反渗透膜的制备方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5316373A (en) * | 1976-07-30 | 1978-02-15 | Toyo Soda Mfg Co Ltd | Preparation of combined membrane |
JPS6146207A (ja) * | 1984-08-09 | 1986-03-06 | Nitto Electric Ind Co Ltd | 複合半透膜の製造方法 |
JP2000024470A (ja) * | 1998-07-10 | 2000-01-25 | Nitto Denko Corp | 液体分離膜の洗浄方法 |
JP2000325759A (ja) * | 1999-05-17 | 2000-11-28 | Toray Ind Inc | 膜の製造方法 |
JP2002177750A (ja) * | 2000-12-14 | 2002-06-25 | Toray Ind Inc | 複合半透膜及びその製造方法 |
JP3525759B2 (ja) * | 1998-09-24 | 2004-05-10 | 東レ株式会社 | 流体分離膜およびその製造方法 |
Family Cites Families (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2727087A (en) * | 1952-04-18 | 1955-12-13 | Gen Electric | Armored oil well cable |
US3023300A (en) * | 1959-08-10 | 1962-02-27 | Hackethal Draht & Kabelwerk Ag | Method and apparatus for forming cable sheath |
US3133137A (en) * | 1960-11-29 | 1964-05-12 | Univ California | High flow porous membranes for separating water from saline solutions |
NL271831A (ja) * | 1960-11-29 | |||
US3567632A (en) * | 1968-09-04 | 1971-03-02 | Du Pont | Permselective,aromatic,nitrogen-containing polymeric membranes |
US3744642A (en) * | 1970-12-30 | 1973-07-10 | Westinghouse Electric Corp | Interface condensation desalination membranes |
US4005012A (en) * | 1975-09-22 | 1977-01-25 | The United States Of America As Represented By The Secretary Of The Interior | Semipermeable membranes and the method for the preparation thereof |
US4277344A (en) * | 1979-02-22 | 1981-07-07 | Filmtec Corporation | Interfacially synthesized reverse osmosis membrane |
US4529646A (en) * | 1984-07-30 | 1985-07-16 | E. I. Du Pont De Nemours And Company | Production of composite membranes |
US4520044A (en) * | 1984-07-30 | 1985-05-28 | E. I. Du Pont De Nemours And Company | Production of composite membranes |
US4761234A (en) * | 1985-08-05 | 1988-08-02 | Toray Industries, Inc. | Interfacially synthesized reverse osmosis membrane |
US4830885A (en) * | 1987-06-08 | 1989-05-16 | Allied-Signal Inc. | Chlorine-resistant semipermeable membranes |
US4872984A (en) * | 1988-09-28 | 1989-10-10 | Hydranautics Corporation | Interfacially synthesized reverse osmosis membrane containing an amine salt and processes for preparing the same |
US4948507A (en) * | 1988-09-28 | 1990-08-14 | Hydranautics Corporation | Interfacially synthesized reverse osmosis membrane containing an amine salt and processes for preparing the same |
US5015380A (en) * | 1989-04-20 | 1991-05-14 | E. I. Du Pont De Nemours And Company | Microporous support layer with interfacially polymerized copolyamide membrane thereon |
US4938872A (en) * | 1989-06-07 | 1990-07-03 | E. I. Du Pont De Nemours And Company | Treatment for reverse osmosis membranes |
US4950404A (en) * | 1989-08-30 | 1990-08-21 | Allied-Signal Inc. | High flux semipermeable membranes |
US4983291A (en) * | 1989-12-14 | 1991-01-08 | Allied-Signal Inc. | Dry high flux semipermeable membranes |
US5173335A (en) * | 1990-07-31 | 1992-12-22 | E. I. Du Pont De Nemours And Company | Method of producing multilayer reverse osmosis membrane of polyamide-urea |
US5152901A (en) * | 1990-09-14 | 1992-10-06 | Ionics, Incorporated | Polyamine-polyamide composite nanofiltration membrane for water softening |
US5254261A (en) * | 1991-08-12 | 1993-10-19 | Hydranautics | Interfacially synthesized reverse osmosis membranes and processes for preparing the same |
JP3501470B2 (ja) * | 1992-05-08 | 2004-03-02 | キヤノン株式会社 | 画像処理装置およびその方法 |
US5234598A (en) * | 1992-05-13 | 1993-08-10 | Allied-Signal Inc. | Thin-film composite membrane |
JPH06146207A (ja) * | 1992-11-10 | 1994-05-27 | Kyushu Sekiyu Kk | 道路の融雪及び凍結防止舗装 |
TW336899B (en) * | 1994-01-26 | 1998-07-21 | Mitsubishi Rayon Co | Microporous membrane made of non-crystalline polymers and method of producing the same |
US5783079A (en) * | 1994-08-29 | 1998-07-21 | Toyo Boseki Kabushiki Kaisha | Composite hollow fiber membrane and process for its production |
US5693227A (en) * | 1994-11-17 | 1997-12-02 | Ionics, Incorporated | Catalyst mediated method of interfacial polymerization on a microporous support, and polymers, fibers, films and membranes made by such method |
US6177011B1 (en) * | 1996-03-18 | 2001-01-23 | Nitto Denko Corporation | Composite reverse osmosis membrane having a separation layer with polyvinyl alcohol coating and method of reverse osmotic treatment of water using the same |
US6536605B2 (en) * | 1997-06-06 | 2003-03-25 | Koch Membrane Systems, Inc. | High performance composite membrane |
US6132804A (en) * | 1997-06-06 | 2000-10-17 | Koch Membrane Systems, Inc. | High performance composite membrane |
US6015495A (en) * | 1998-02-18 | 2000-01-18 | Saehan Industries Incorporation | Composite polyamide reverse osmosis membrane and method of producing the same |
EP1283068A1 (en) * | 2001-07-30 | 2003-02-12 | Saehan Industries, Inc. | Reverse osmosis membrane having excellent anti-fouling property and method for manufacturing the same |
JP4500002B2 (ja) * | 2003-05-06 | 2010-07-14 | 日東電工株式会社 | 複合半透膜及びその製造方法 |
JP4656503B2 (ja) * | 2004-10-01 | 2011-03-23 | 日東電工株式会社 | 複合半透膜及びその製造方法 |
JP4656502B2 (ja) * | 2004-10-01 | 2011-03-23 | 日東電工株式会社 | 複合半透膜及びその製造方法 |
JP2006102594A (ja) * | 2004-10-01 | 2006-04-20 | Nitto Denko Corp | 複合半透膜の製造方法 |
JP4656511B2 (ja) * | 2004-10-04 | 2011-03-23 | 日東電工株式会社 | 複合逆浸透膜の製造方法 |
JP4936438B2 (ja) * | 2006-10-10 | 2012-05-23 | 日東電工株式会社 | 乾燥複合半透膜の製造方法 |
JP2008093544A (ja) * | 2006-10-10 | 2008-04-24 | Nitto Denko Corp | 複合半透膜及びその製造方法 |
-
2005
- 2005-03-29 JP JP2005094604A patent/JP4656503B2/ja not_active Expired - Fee Related
- 2005-09-09 EP EP05781966A patent/EP1825905A4/en not_active Withdrawn
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- 2005-09-09 WO PCT/JP2005/016617 patent/WO2006038425A1/ja active Application Filing
- 2005-09-09 US US11/664,428 patent/US20080053893A1/en not_active Abandoned
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2010
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Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5316373A (en) * | 1976-07-30 | 1978-02-15 | Toyo Soda Mfg Co Ltd | Preparation of combined membrane |
JPS6146207A (ja) * | 1984-08-09 | 1986-03-06 | Nitto Electric Ind Co Ltd | 複合半透膜の製造方法 |
JP2000024470A (ja) * | 1998-07-10 | 2000-01-25 | Nitto Denko Corp | 液体分離膜の洗浄方法 |
JP3525759B2 (ja) * | 1998-09-24 | 2004-05-10 | 東レ株式会社 | 流体分離膜およびその製造方法 |
JP2000325759A (ja) * | 1999-05-17 | 2000-11-28 | Toray Ind Inc | 膜の製造方法 |
JP2002177750A (ja) * | 2000-12-14 | 2002-06-25 | Toray Ind Inc | 複合半透膜及びその製造方法 |
Also Published As
Publication number | Publication date |
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KR20070057268A (ko) | 2007-06-04 |
US20080053893A1 (en) | 2008-03-06 |
EP1825905A4 (en) | 2009-04-15 |
KR100969049B1 (ko) | 2010-07-09 |
WO2006038425A1 (ja) | 2006-04-13 |
US20100173083A1 (en) | 2010-07-08 |
EP1825905A1 (en) | 2007-08-29 |
JP2006122887A (ja) | 2006-05-18 |
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