JP6446572B1 - 芳香族ポリスルホン樹脂およびその膜 - Google Patents
芳香族ポリスルホン樹脂およびその膜 Download PDFInfo
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- JP6446572B1 JP6446572B1 JP2018006604A JP2018006604A JP6446572B1 JP 6446572 B1 JP6446572 B1 JP 6446572B1 JP 2018006604 A JP2018006604 A JP 2018006604A JP 2018006604 A JP2018006604 A JP 2018006604A JP 6446572 B1 JP6446572 B1 JP 6446572B1
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- Prior art keywords
- aromatic polysulfone
- polysulfone resin
- membrane
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- formula
- 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.)
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- 125000003118 aryl group Chemical group 0.000 title claims abstract description 104
- 229920005989 resin Polymers 0.000 title claims abstract description 103
- 239000011347 resin Substances 0.000 title claims abstract description 103
- 229920002492 poly(sulfone) Polymers 0.000 title claims abstract description 90
- 239000012528 membrane Substances 0.000 title claims description 88
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 description 37
- 239000002904 solvent Substances 0.000 description 25
- 239000012510 hollow fiber Substances 0.000 description 24
- 238000004519 manufacturing process Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 17
- 230000008602 contraction Effects 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 12
- 229920001477 hydrophilic polymer Polymers 0.000 description 12
- 238000006068 polycondensation reaction Methods 0.000 description 10
- HGWMELCMYSUIOM-UHFFFAOYSA-N 1-chloro-3-(4-chlorophenyl)sulfonylbenzene Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=CC(Cl)=C1 HGWMELCMYSUIOM-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 230000001954 sterilising effect Effects 0.000 description 8
- 238000004659 sterilization and disinfection Methods 0.000 description 8
- IBRQUKZZBXZOBA-UHFFFAOYSA-N 1-chloro-3-(3-chlorophenyl)sulfonylbenzene Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 IBRQUKZZBXZOBA-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 230000005855 radiation Effects 0.000 description 7
- -1 2-ethylhexyl group Chemical group 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 230000001112 coagulating effect Effects 0.000 description 4
- 238000000502 dialysis Methods 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000001471 micro-filtration Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- NYCCIHSMVNRABA-UHFFFAOYSA-N 1,3-diethylimidazolidin-2-one Chemical compound CCN1CCN(CC)C1=O NYCCIHSMVNRABA-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- ZDULHUHNYHJYKA-UHFFFAOYSA-N 2-propan-2-ylsulfonylpropane Chemical compound CC(C)S(=O)(=O)C(C)C ZDULHUHNYHJYKA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 150000008043 acidic salts Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 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
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
- C08G65/4056—(I) or (II) containing sulfur
-
- 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
- B01D71/66—Polymers having sulfur in the main chain, with or without nitrogen, oxygen or carbon only
- B01D71/68—Polysulfones; Polyethersulfones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
- C08G75/23—Polyethersulfones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/06—Polysulfones; Polyethersulfones
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/02—Details relating to pores or porosity of the membranes
- B01D2325/0282—Dynamic pores-stimuli responsive membranes, e.g. thermoresponsive or pH-responsive
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2201/00—Foams characterised by the foaming process
- C08J2201/04—Foams characterised by the foaming process characterised by the elimination of a liquid or solid component, e.g. precipitation, leaching out, evaporation
- C08J2201/052—Inducing phase separation by thermal treatment, e.g. cooling a solution
- C08J2201/0522—Inducing phase separation by thermal treatment, e.g. cooling a solution the liquid phase being organic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2201/00—Foams characterised by the foaming process
- C08J2201/04—Foams characterised by the foaming process characterised by the elimination of a liquid or solid component, e.g. precipitation, leaching out, evaporation
- C08J2201/054—Precipitating the polymer by adding a non-solvent or a different solvent
- C08J2201/0542—Precipitating the polymer by adding a non-solvent or a different solvent from an organic solvent-based polymer composition
- C08J2201/0544—Precipitating the polymer by adding a non-solvent or a different solvent from an organic solvent-based polymer composition the non-solvent being aqueous
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2381/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen, or carbon only; Polysulfones; Derivatives of such polymers
- C08J2381/06—Polysulfones; Polyethersulfones
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Polyethers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
芳香族ポリスルホン樹脂は、典型的には、2価の芳香族基(芳香族化合物から、その芳香環に結合した水素原子を2個除いて得られる残基)とスルホニル基(−SO2−)と酸素原子とを含む繰返し単位を有する樹脂である。芳香族ポリスルホン樹脂は、耐熱性や耐薬品性の点から、下記式(1)で表される繰返し単位(以下、「繰返し単位(1)」ということがある。)を有することが好ましく、さらに、下記式(2)で表される繰返し単位(以下、「繰返し単位(2)」ということがある。)や、下記式(3)で表される繰返し単位(以下、「繰返し単位(3)」ということがある。)などの他の繰返し単位を1種以上有していてもよい。
本実施形態の芳香族ポリスルホン樹脂を含む膜は、例えば、平膜であってもよいし、管状膜であってもよいし、中空糸膜であってもよい。また、本実施形態の芳香族ポリスルホン樹脂を含む膜は、単層膜であってもよいし、多層膜であってもよい。なお、多層膜である場合、本実施形態の芳香族ポリスルホン樹脂を含む層のみを2層以上有する多層膜であってもよいし、本実施形態の芳香族ポリスルホン樹脂を含む層を1層以上有し、かつ他の層を1層以上有する多層膜であってもよい。
膜の製造は、公知の方法を適宜採用することができる。多孔質膜の製造は、例えば、芳香族ポリスルホン樹脂を溶媒に溶解させ、得られた溶液を所定の形状に押し出し、エアギャップを介して乾湿式で、またはエアギャップを介さずに湿式で、凝固液に導入して、相分離および脱溶媒することにより行ってもよい。また、この方法とは別に、多孔質膜の製造は、芳香族ポリスルホン樹脂を溶媒に溶解させ、得られた溶液を所定の形状の基材に流延し、凝固液に浸漬して、相分離および脱溶媒することにより行ってもよい。
芳香族ポリスルホン樹脂1gをN,N−ジメチルホルムアミドに溶解させて、その容量を1dLとし、この溶液の粘度(η)を、オストワルド型粘度管を用いて、25℃で測定した。また、溶媒であるN,N−ジメチルホルムアミドの粘度(η0)を、オストワルド型粘度管を用いて、25℃で測定した。前記溶液の濃度は1g/dLであるので、比粘性率((η−η0)/η0)の値が、単位dL/gの還元粘度の値となる。
製造例1〜5で得られた樹脂40gとN−メチル−2−ピロリドン160gを60℃下2時間撹拌し、芳香族ポリスルホン樹脂溶液を得た。次いで、この溶液をガラス板(厚さ3mm)の上にフィルムアプリケーターを用いて熱処理後の膜厚が30μmとなるようにキャストした。得られた樹脂層を、高温熱風乾燥器で80℃で加熱して、樹脂層中の残存溶媒量が10質量%以下になるように溶媒を除去した後、窒素雰囲気下250℃で熱処理することで、芳香族ポリスルホン樹脂フィルムを得た。
以下の製造例では、ジハロゲノスルホン化合物として、4,4’−ジクロロジフェニルスルホンと、3,4’−ジクロロジフェニルスルホンとが混合したジクロロジフェニルスルホン混合物を用いた。
試料:アセトン5mlに試料を0.1gを溶かした溶液を1μL注入
装置:Agilent製ガスクロマトグラフ6850型
カラム:Agilent製GCカラムDB−5(内径:0.25mm、長さ:30m、膜厚:1μm)
カラム温度:290℃
検出器:水素炎イオン化型
得られたスペクトルにおいて、保持時間15分以降に検出されたピーク面積の総和を100とし、面積百分率法で保持時間15.4分から15.7分に検出されたピーク面積を求め、ジクロロジフェニルスルホン混合物の総質量に対する3,4’−ジクロロジフェニルスルホンの含有量を算出した。
得られたスペクトルにおいて、保持時間14分以降に検出されたピーク面積の総和を100とし、面積百分率法で保持時間14.5分から14.8分に検出されたピーク面積を求め、ジヒドロキシジフェニルスルホン混合物の総質量に対する3,4’−ジヒドロキシジフェニルスルホンの含有量を算出した。
撹拌機、窒素導入管、温度計、および先端に受器を付したコンデンサーを備えた、容量が500mLの重合槽に、4,4’−ジヒドロキシジフェニルスルホン(3,4’−ジヒドロキシジフェニルスルホンの含有量:0質量%)100.1g、4,4’−ジクロロジフェニルスルホン(3,4’−ジクロロジフェニルスルホンの含有量:0.1質量%)117.7g、および重合溶媒としてジフェニルスルホン193.6gを仕込み、系内に窒素ガスを流通させながら180℃まで昇温させた。得られた溶液に、炭酸カリウム56.5gを添加した後、290℃まで徐々に昇温させ、290℃でさらに4時間反応させた。次いで、得られた反応液を室温まで冷却して反応生成物を固化させた。固形物を取り出して細かく粉砕した後、粉砕した固形物を温水による洗浄およびアセトンとメタノールの混合溶媒による洗浄を数回行った。さらに、洗浄後の固形物を150℃で加熱乾燥を行い、芳香族ポリスルホン樹脂の白色粉末を得た。
ジクロロジフェニルスルホン混合物の総量に対する3,4’−ジクロロジフェニルスルホンの含有量を0.3質量%に変更した以外は、製造例1と同様にして芳香族ポリスルホン樹脂を得た。
ジクロロジフェニルスルホン混合物の総量に対する3,4’−ジクロロジフェニルスルホンの含有量を0質量%に変更した以外は、製造例1と同様にして芳香族ポリスルホン樹脂を得た。
ジクロロジフェニルスルホン混合物の総量に対する3,4’−ジクロロジフェニルスルホンの含有量を0.7質量%に変更した以外は、製造例1と同様にして芳香族ポリスルホン樹脂を得た。
ジクロロジフェニルスルホン混合物の総量に対する3,4’−ジクロロジフェニルスルホンの含有量を1.0質量%に変更した以外は、製造例1と同様にして芳香族ポリスルホン樹脂を得た。
[実施例1]
500mLセパラブルフラスコに、製造例1で得られた芳香族ポリスルホン樹脂40g、ポリエチレングリコール400 120gおよびN−メチル−2−ピロリドン140gを入れ、60℃で2時間撹拌して、淡黄色の芳香族ポリスルホン樹脂溶液を得た。この溶液を、厚さ3mmのガラス板上にフィルムアプリケーターを用いて乾燥前の樹脂層の厚さ300μmとなるように塗布し、塗布した直後にガラス板を水中に浸漬させた後、ガラス板から剥離した塗膜を30分間水中で静置した。次いで、高温熱風乾燥器を用いて50℃でこの塗膜を終夜乾燥し、芳香族ポリスルホン樹脂を含む多孔質膜を得た。
製造例2で得られた芳香族ポリスルホン樹脂を用いた以外は、実施例1と同様にして芳香族ポリスルホン樹脂を含む多孔質膜を得た。
製造例3で得られた芳香族ポリスルホン樹脂を用いた以外は、実施例1と同様にして芳香族ポリスルホン樹脂を含む多孔質膜を得た。
製造例4で得られた芳香族ポリスルホン樹脂を用いた以外は、実施例1と同様にして芳香族ポリスルホン樹脂を含む多孔質膜を得た。
製造例5で得られた芳香族ポリスルホン樹脂を用いた以外は、実施例1と同様にして芳香族ポリスルホン樹脂を含む多孔質膜を得た。
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JP2018006604A JP6446572B1 (ja) | 2018-01-18 | 2018-01-18 | 芳香族ポリスルホン樹脂およびその膜 |
EP18900642.2A EP3741789B1 (en) | 2018-01-18 | 2018-11-29 | Aromatic polysulfone resin and membrane thereof |
CN201880086443.3A CN111601838B (zh) | 2018-01-18 | 2018-11-29 | 芳香族聚砜树脂及其膜 |
KR1020207019964A KR102642654B1 (ko) | 2018-01-18 | 2018-11-29 | 방향족 폴리술폰 수지 및 그 막 |
PCT/JP2018/044011 WO2019142507A1 (ja) | 2018-01-18 | 2018-11-29 | 芳香族ポリスルホン樹脂およびその膜 |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5598229A (en) * | 1978-12-06 | 1980-07-26 | Gen Electric | Thermoplastic organic polymer |
JP2006077043A (ja) * | 2004-09-07 | 2006-03-23 | Sumitomo Chemical Co Ltd | ポリエーテルスルホンの精製方法並びにそれにより得られる高純度ポリエーテルスルホン溶液及び高純度ポリエーテルスルホン |
JP2008094921A (ja) * | 2006-10-10 | 2008-04-24 | Unitika Ltd | 被膜形成用樹脂 |
WO2017114163A1 (zh) * | 2015-12-30 | 2017-07-06 | 金发科技股份有限公司 | 一种砜聚合物的组合物及其制备方法与应用 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5298793A (en) * | 1976-02-16 | 1977-08-18 | Sumitomo Chem Co Ltd | Preparation of adducts of maleic anhydride with liquid polymers |
JP3580314B1 (ja) | 2003-12-09 | 2004-10-20 | 東洋紡績株式会社 | ポリスルホン系選択透過性中空糸膜束およびその製造方法 |
JP4839631B2 (ja) | 2005-02-22 | 2011-12-21 | 東洋紡績株式会社 | ポリスルホン系選択透過性中空糸膜束および血液浄化器 |
DE102006036496A1 (de) | 2006-07-28 | 2008-02-07 | Leibniz-Institut Für Polymerforschung Dresden E.V. | Sulfonierte Polyarylverbindungen, Membranmaterial daraus, Verfahren zu ihrer Herstellung und Verwendung |
JP2009245774A (ja) * | 2008-03-31 | 2009-10-22 | Honda Motor Co Ltd | 固体高分子型燃料電池用膜−電極構造体 |
JP5703645B2 (ja) | 2009-09-29 | 2015-04-22 | 住友化学株式会社 | 芳香族ポリスルホン樹脂及びその膜 |
US10265663B2 (en) * | 2013-09-09 | 2019-04-23 | Basf Se | Polyarylene ether sulfone-polymers for membrane applications |
JP6589758B2 (ja) | 2016-07-04 | 2019-10-16 | 株式会社ニューフレアテクノロジー | マルチ荷電粒子ビーム描画装置及びマルチ荷電粒子ビーム描画方法 |
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5598229A (en) * | 1978-12-06 | 1980-07-26 | Gen Electric | Thermoplastic organic polymer |
JP2006077043A (ja) * | 2004-09-07 | 2006-03-23 | Sumitomo Chemical Co Ltd | ポリエーテルスルホンの精製方法並びにそれにより得られる高純度ポリエーテルスルホン溶液及び高純度ポリエーテルスルホン |
JP2008094921A (ja) * | 2006-10-10 | 2008-04-24 | Unitika Ltd | 被膜形成用樹脂 |
WO2017114163A1 (zh) * | 2015-12-30 | 2017-07-06 | 金发科技股份有限公司 | 一种砜聚合物的组合物及其制备方法与应用 |
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