JPS6153087B2 - - Google Patents
Info
- Publication number
- JPS6153087B2 JPS6153087B2 JP9538981A JP9538981A JPS6153087B2 JP S6153087 B2 JPS6153087 B2 JP S6153087B2 JP 9538981 A JP9538981 A JP 9538981A JP 9538981 A JP9538981 A JP 9538981A JP S6153087 B2 JPS6153087 B2 JP S6153087B2
- Authority
- JP
- Japan
- Prior art keywords
- polyimide
- aromatic
- polyamic acid
- membrane
- porous membrane
- 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.)
- Expired
Links
- 239000012528 membrane Substances 0.000 claims description 93
- 239000004642 Polyimide Substances 0.000 claims description 80
- 229920001721 polyimide Polymers 0.000 claims description 80
- 229920005575 poly(amic acid) Polymers 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 238000000926 separation method Methods 0.000 claims description 41
- 239000002904 solvent Substances 0.000 claims description 22
- 239000002131 composite material Substances 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 18
- 239000002798 polar solvent Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 33
- 239000007789 gas Substances 0.000 description 25
- -1 aromatic tetracarboxylic acid Chemical class 0.000 description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 17
- 239000010408 film Substances 0.000 description 17
- 239000010410 layer Substances 0.000 description 15
- 239000011247 coating layer Substances 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000035699 permeability Effects 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 9
- 150000004984 aromatic diamines Chemical class 0.000 description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 150000003949 imides Chemical class 0.000 description 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000007363 ring formation reaction Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000005345 coagulation Methods 0.000 description 5
- 230000015271 coagulation Effects 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000001112 coagulating effect Effects 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 2
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 229940090668 parachlorophenol Drugs 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- UWHSPZZUAYSGTB-UHFFFAOYSA-N 1,1,3,3-tetraethylurea Chemical compound CCN(CC)C(=O)N(CC)CC UWHSPZZUAYSGTB-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- NBAUUNCGSMAPFM-UHFFFAOYSA-N 3-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC(C(O)=O)=C1C(O)=O NBAUUNCGSMAPFM-UHFFFAOYSA-N 0.000 description 1
- LXJLFVRAWOOQDR-UHFFFAOYSA-N 3-(3-aminophenoxy)aniline Chemical compound NC1=CC=CC(OC=2C=C(N)C=CC=2)=C1 LXJLFVRAWOOQDR-UHFFFAOYSA-N 0.000 description 1
- NDXGRHCEHPFUSU-UHFFFAOYSA-N 3-(3-aminophenyl)aniline Chemical group NC1=CC=CC(C=2C=C(N)C=CC=2)=C1 NDXGRHCEHPFUSU-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 description 1
- DVXYMCJCMDTSQA-UHFFFAOYSA-N 3-[2-(3-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=CC(N)=CC=1C(C)(C)C1=CC=CC(N)=C1 DVXYMCJCMDTSQA-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- AIVVXPSKEVWKMY-UHFFFAOYSA-N 4-(3,4-dicarboxyphenoxy)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 AIVVXPSKEVWKMY-UHFFFAOYSA-N 0.000 description 1
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 1
- VILWHDNLOJCHNJ-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfanylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1SC1=CC=C(C(O)=O)C(C(O)=O)=C1 VILWHDNLOJCHNJ-UHFFFAOYSA-N 0.000 description 1
- AVCOFPOLGHKJQB-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfonylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 AVCOFPOLGHKJQB-UHFFFAOYSA-N 0.000 description 1
- IWXCYYWDGDDPAC-UHFFFAOYSA-N 4-[(3,4-dicarboxyphenyl)methyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C(C(O)=O)=C1 IWXCYYWDGDDPAC-UHFFFAOYSA-N 0.000 description 1
- GEYAGBVEAJGCFB-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)propan-2-yl]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(C)(C)C1=CC=C(C(O)=O)C(C(O)=O)=C1 GEYAGBVEAJGCFB-UHFFFAOYSA-N 0.000 description 1
- ZYEDGEXYGKWJPB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)(C)C1=CC=C(N)C=C1 ZYEDGEXYGKWJPB-UHFFFAOYSA-N 0.000 description 1
- CQMIJLIXKMKFQW-UHFFFAOYSA-N 4-phenylbenzene-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C1C1=CC=CC=C1 CQMIJLIXKMKFQW-UHFFFAOYSA-N 0.000 description 1
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical group OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005360 alkyl sulfoxide group Chemical group 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- TUQQUUXMCKXGDI-UHFFFAOYSA-N bis(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C=CC=2)=C1 TUQQUUXMCKXGDI-UHFFFAOYSA-N 0.000 description 1
- MYMCSQDRHUQQDW-UHFFFAOYSA-N bis(4-amino-3-methylphenyl)methanone Chemical compound C1=C(N)C(C)=CC(C(=O)C=2C=C(C)C(N)=CC=2)=C1 MYMCSQDRHUQQDW-UHFFFAOYSA-N 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003779 heat-resistant material Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000012510 hollow fiber Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31721—Of polyimide
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Laminated Bodies (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9538981A JPS57209608A (en) | 1981-06-22 | 1981-06-22 | Preparation of composite polyimide separation film |
| US06/387,493 US4440643A (en) | 1981-06-22 | 1982-06-11 | Process for producing aromatic polyimide composite separating membrane |
| GB8217147A GB2102334B (en) | 1981-06-22 | 1982-06-14 | Producing aromatic polyimide membrane |
| DE3223074A DE3223074C2 (de) | 1981-06-22 | 1982-06-21 | Verfahren zur Herstellung einer Polyimid-Trennmembran |
| CA000405608A CA1190100A (en) | 1981-06-22 | 1982-06-21 | Process for producing aromatic polyimide composite separating membrane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9538981A JPS57209608A (en) | 1981-06-22 | 1981-06-22 | Preparation of composite polyimide separation film |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57209608A JPS57209608A (en) | 1982-12-23 |
| JPS6153087B2 true JPS6153087B2 (US20110009641A1-20110113-C00116.png) | 1986-11-15 |
Family
ID=14136288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9538981A Granted JPS57209608A (en) | 1981-06-22 | 1981-06-22 | Preparation of composite polyimide separation film |
Country Status (5)
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4532041A (en) * | 1983-05-13 | 1985-07-30 | Exxon Research And Engineering Co. | Asymmetric polyimide reverse osmosis membrane, method for preparation of same and use thereof for organic liquid separations |
| US4575385A (en) * | 1983-06-30 | 1986-03-11 | Monsanto Company | Permeation modified gas separation membranes |
| JPS6094106A (ja) * | 1983-10-27 | 1985-05-27 | Nitto Electric Ind Co Ltd | 複合膜の製造方法 |
| JPS60206639A (ja) * | 1984-03-31 | 1985-10-18 | 日東電工株式会社 | ポリイミド−金属箔複合フイルムの製造方法 |
| JPS6119813A (ja) * | 1984-06-20 | 1986-01-28 | Agency Of Ind Science & Technol | ポリイミド中空糸の製造法 |
| US4806189A (en) * | 1984-08-13 | 1989-02-21 | Monsanto Company | Composite fluid separation membranes |
| US4562100A (en) * | 1984-09-14 | 1985-12-31 | E. I. Du Pont De Nemours And Company | Polyimide coating compositions from diesterified anhydride and aromatic diamine |
| US4602922A (en) * | 1984-11-09 | 1986-07-29 | Research Foundation Of State University Of New York | Method of making membranes for gas separation and the composite membranes |
| JPH0691930B2 (ja) * | 1986-03-18 | 1994-11-16 | 宇部興産株式会社 | 気体分離膜 |
| US4705540A (en) * | 1986-04-17 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Polyimide gas separation membranes |
| US4880584A (en) * | 1986-04-25 | 1989-11-14 | Trw, Inc. | Fiber reinforced thermoplastic resin matrix composites |
| EP0263212B1 (en) * | 1986-10-08 | 1990-12-27 | Ube Industries, Ltd. | Method for removing water vapor from water vapor-containing gas |
| US4717393A (en) * | 1986-10-27 | 1988-01-05 | E. I. Du Pont De Nemours And Company | Polyimide gas separation membranes |
| US4717394A (en) * | 1986-10-27 | 1988-01-05 | E. I. Du Pont De Nemours And Company | Polyimide gas separation membranes |
| US4978430A (en) * | 1986-12-06 | 1990-12-18 | Ube Industries, Ltd. | Method for dehydration and concentration of aqueous solution containing organic compound |
| US4963165A (en) * | 1987-04-27 | 1990-10-16 | Membrane Technology & Research, Inc. | Composite membrane, method of preparation and use |
| JPH0673616B2 (ja) * | 1987-10-09 | 1994-09-21 | 宇部興産株式会社 | ポリイミド二層中空糸膜の製造法 |
| US4880442A (en) * | 1987-12-22 | 1989-11-14 | E. I. Du Pont De Nemours And Company | Polyimide gas separation membranes |
| US4919856A (en) * | 1988-02-23 | 1990-04-24 | Dainippon Ink And Chemicals, Inc. | Process for producing membranes for use in gas separation |
| US4892896A (en) * | 1988-04-04 | 1990-01-09 | Ethyl Corporation | Processing polyimide precursor compositions |
| US4838900A (en) * | 1988-04-13 | 1989-06-13 | E. I. Du Pont De Nemours And Company | Polyimide gas separation membranes |
| US4931310A (en) * | 1988-11-25 | 1990-06-05 | International Business Machines Corporation | Process for treating the surface of polyimides to improve properties to receive metal layer |
| US4897092A (en) * | 1989-02-27 | 1990-01-30 | Air Products And Chemicals, Inc. | Polyimide membrane having improved flux |
| US4932982A (en) * | 1989-06-01 | 1990-06-12 | E. I. Du Pont De Nemours And Company | Copolyimide gas separation membranes derived from substituted phenylene diamines and substituted methylene dianilines |
| US4981497A (en) * | 1989-06-01 | 1991-01-01 | E. I. Du Pont De Nemours And Company | Amine-modified polyimide membranes |
| US5074891A (en) * | 1989-07-27 | 1991-12-24 | Hoechst Celanese Corp. | Method of gas separation and membranes therefor |
| US4988371A (en) * | 1989-09-12 | 1991-01-29 | The Dow Chemical Company | Novel alicyclic polyimide gas separation membranes |
| US5032279A (en) * | 1989-09-21 | 1991-07-16 | Occidental Chemical Corporation | Separation of fluids using polyimidesiloxane membrane |
| US4983191A (en) * | 1989-10-10 | 1991-01-08 | E. I. Du Pont De Nemours And Company | Production of aromatic polyimide membranes |
| US5178649A (en) * | 1989-12-21 | 1993-01-12 | The Dow Chemical Company | Poly(arylene ether ketimine) gas separation membranes |
| US5338827A (en) * | 1990-01-30 | 1994-08-16 | Trw Inc. | Polyimide resins useful at high temperatures |
| US5432001A (en) * | 1990-01-30 | 1995-07-11 | Trw Inc. | Concentrated prepolymer composition useful for forming polyimide articles |
| US5202411A (en) * | 1990-04-06 | 1993-04-13 | W. R. Grace & Co.-Conn. | Tri-component polyimide composition and preparation thereof |
| US5162492A (en) * | 1990-10-11 | 1992-11-10 | E. I. Du Pont De Nemours And Company | Hydrolytically and oxidatively stable polyimides |
| US5085676A (en) * | 1990-12-04 | 1992-02-04 | E. I. Du Pont De Nemours And Company | Novel multicomponent fluid separation membranes |
| US5266100A (en) * | 1992-09-02 | 1993-11-30 | E. I. Du Pont De Nemours And Company | Alkyl substituted polyimide, polyamide and polyamide-imide gas separation membranes |
| US5248319A (en) * | 1992-09-02 | 1993-09-28 | E. I. Du Pont De Nemours And Company | Gas separation membranes made from blends of aromatic polyamide, polymide or polyamide-imide polymers |
| US5409524A (en) * | 1992-12-01 | 1995-04-25 | The Dow Chemical Company | Membranes having improved selectivity and recovery, and process for making same |
| US5443728A (en) * | 1994-04-28 | 1995-08-22 | Praxair Technology, Inc. | Method of preparing membranes from blends of polyetherimide and polyimide polymers |
| EP0682977A3 (en) * | 1994-05-20 | 2000-01-12 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Improved polymeric membrane |
| US5647894A (en) * | 1994-06-08 | 1997-07-15 | Nitto Denko Corporation | Gas separating composite membrane and process for producing the same |
| JP3361655B2 (ja) * | 1995-05-10 | 2003-01-07 | エヌオーケー株式会社 | 多孔質セラミックス複合中空糸膜およびその製造法 |
| US5725633A (en) * | 1995-06-30 | 1998-03-10 | Praxair Technology, Inc. | Sulfonated polyimide gas separation membranes |
| US5618334A (en) * | 1995-06-30 | 1997-04-08 | Praxair Technology, Inc. | Sulfonated polyimide gas separation membranes |
| US5753008A (en) * | 1995-07-12 | 1998-05-19 | Bend Research, Inc. | Solvent resistant hollow fiber vapor permeation membranes and modules |
| US6180008B1 (en) | 1998-07-30 | 2001-01-30 | W. R. Grace & Co.-Conn. | Polyimide membranes for hyperfiltration recovery of aromatic solvents |
| US6497747B1 (en) | 1999-09-24 | 2002-12-24 | Praxair Technology, Inc. | Production and use of improved polyimide separation membranes |
| CN1756654B (zh) * | 2002-12-27 | 2011-05-11 | 日本电气株式会社 | 薄片材料及布线板 |
| CA2435538A1 (en) * | 2003-07-18 | 2005-01-18 | Universite Laval | Solvent resistant asymmetric integrally skinned membranes |
| CA2540085C (en) | 2003-09-29 | 2010-11-16 | Bruce Michael Koivisto | High alcohol content gel-like and foaming compositions |
| US7803214B2 (en) * | 2006-07-21 | 2010-09-28 | Ube Industries, Ltd. | Asymmetric hollow-fiber gas separation membrane, gas separation method and gas separation membrane module |
| WO2012077810A1 (ja) * | 2010-12-09 | 2012-06-14 | 宇部興産株式会社 | 非対称ガス分離膜およびこれを用いてメタノールを分離する方法 |
| US8388744B1 (en) * | 2011-08-30 | 2013-03-05 | General Electric Company | Systems and methods for using a boehmite bond-coat with polyimide membranes for gas separation |
| BR112016021096A2 (pt) * | 2014-03-13 | 2017-08-15 | 3M Innovative Properties Company | Membranas assimétricas e métodos relacionados |
| GB201510648D0 (en) * | 2015-06-17 | 2015-07-29 | Fujifilm Mfg Europe Bv | Composite membranes |
| CN105413499B (zh) * | 2015-11-27 | 2017-07-07 | 浙江大学 | 一种交联改性聚酰胺复合膜及其制备方法 |
| KR102189214B1 (ko) * | 2016-07-25 | 2020-12-09 | 우베 고산 가부시키가이샤 | 다공질 폴리이미드막의 제조 방법 및 이 방법으로 제조되는 다공질 폴리이미드막 |
| CN112705050B (zh) * | 2019-10-24 | 2022-12-09 | 中国石油化工股份有限公司 | 聚酰亚胺渗透汽化分离膜及其制备方法和分离方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4945152A (US20110009641A1-20110113-C00116.png) * | 1972-07-20 | 1974-04-30 | ||
| US4071590A (en) * | 1974-11-02 | 1978-01-31 | Forschungsinstitute Bergof Gmbh | Composite asymmetrical membranes |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5471785A (en) * | 1977-11-18 | 1979-06-08 | Nitto Electric Ind Co Ltd | Selectively permeable membrane and production thereof |
| US4271288A (en) * | 1979-07-02 | 1981-06-02 | The Dow Chemical Company | Novel polyamic acid polymers and polyimide derivatives thereof |
| JPS56118857A (en) * | 1980-02-25 | 1981-09-18 | Nitto Electric Ind Co | Thermofusing polyimide composite film and its manufacture |
| US4358581A (en) * | 1980-12-05 | 1982-11-09 | E. I. Du Pont De Nemours And Company | Polyimide manufacture |
-
1981
- 1981-06-22 JP JP9538981A patent/JPS57209608A/ja active Granted
-
1982
- 1982-06-11 US US06/387,493 patent/US4440643A/en not_active Expired - Lifetime
- 1982-06-14 GB GB8217147A patent/GB2102334B/en not_active Expired
- 1982-06-21 DE DE3223074A patent/DE3223074C2/de not_active Expired
- 1982-06-21 CA CA000405608A patent/CA1190100A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4945152A (US20110009641A1-20110113-C00116.png) * | 1972-07-20 | 1974-04-30 | ||
| US4071590A (en) * | 1974-11-02 | 1978-01-31 | Forschungsinstitute Bergof Gmbh | Composite asymmetrical membranes |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2102334A (en) | 1983-02-02 |
| US4440643A (en) | 1984-04-03 |
| DE3223074A1 (de) | 1983-01-05 |
| CA1190100A (en) | 1985-07-09 |
| GB2102334B (en) | 1984-10-31 |
| DE3223074C2 (de) | 1986-02-20 |
| JPS57209608A (en) | 1982-12-23 |
