JPS6251297B2 - - Google Patents

Info

Publication number: JPS6251297B2
Authority: JP; Japan
Prior art keywords: group; ion; composite membrane; permeable; formula
Prior art date: 1981-01-19
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

Application number

JP56004949A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57119928A (en

Inventor

Takeyuki Kawaguchi

Hiromasa Minematsu

Yuzuru Hayashi

Shigeyoshi Hara

Fumio Ueda

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Teijin Ltd

Original Assignee

Teijin Ltd

Priority date (The priority date 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 date listed.)

1981-01-19

Filing date

1981-01-19

Publication date

1987-10-29

1981-01-19 Application filed by Teijin Ltd filed Critical Teijin Ltd

1981-01-19 Priority to JP56004949A priority Critical patent/JPS57119928A/ja

1982-07-26 Publication of JPS57119928A publication Critical patent/JPS57119928A/ja

1987-10-29 Publication of JPS6251297B2 publication Critical patent/JPS6251297B2/ja

Status Granted legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 claims description 180
239000012528 membrane Substances 0.000 claims description 153
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 82
239000002131 composite material Substances 0.000 claims description 77
125000003277 amino group Chemical group 0.000 claims description 67
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 53
125000004432 carbon atom Chemical group C* 0.000 claims description 51
239000003431 cross linking reagent Substances 0.000 claims description 44
238000004132 cross linking Methods 0.000 claims description 38
150000001875 compounds Chemical class 0.000 claims description 37
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 34
125000000524 functional group Chemical group 0.000 claims description 33
239000005720 sucrose Substances 0.000 claims description 33
229930006000 Sucrose Natural products 0.000 claims description 32
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 31
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 26
125000001302 tertiary amino group Chemical group 0.000 claims description 25
238000005341 cation exchange Methods 0.000 claims description 21
238000005349 anion exchange Methods 0.000 claims description 20
150000001491 aromatic compounds Chemical class 0.000 claims description 19
239000011780 sodium chloride Substances 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 16
238000010438 heat treatment Methods 0.000 claims description 16
229920006037 cross link polymer Polymers 0.000 claims description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
229920002492 poly(sulfone) Polymers 0.000 claims description 13
125000001931 aliphatic group Chemical group 0.000 claims description 12
150000002500 ions Chemical class 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
238000009835 boiling Methods 0.000 claims description 5
150000004820 halides Chemical group 0.000 claims description 5
125000002128 sulfonyl halide group Chemical group 0.000 claims description 5
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 4
UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
230000008030 elimination Effects 0.000 claims description 3
238000003379 elimination reaction Methods 0.000 claims description 3
230000009257 reactivity Effects 0.000 claims description 3
150000003458 sulfonic acid derivatives Chemical group 0.000 claims description 3
FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims description 2
150000001244 carboxylic acid anhydrides Chemical group 0.000 claims description 2
230000010220 ion permeability Effects 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
JPPYSPAXPNNOBC-UHFFFAOYSA-N 5-chlorosulfonylbenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(S(Cl)(=O)=O)=C1 JPPYSPAXPNNOBC-UHFFFAOYSA-N 0.000 claims 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
230000001588 bifunctional effect Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 56
239000002585 base Substances 0.000 description 49
238000006243 chemical reaction Methods 0.000 description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
239000007864 aqueous solution Substances 0.000 description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 description 22
125000005843 halogen group Chemical group 0.000 description 21
150000003839 salts Chemical class 0.000 description 19
238000005342 ion exchange Methods 0.000 description 18
238000000034 method Methods 0.000 description 18
239000002904 solvent Substances 0.000 description 17
125000000217 alkyl group Chemical group 0.000 description 16
150000002430 hydrocarbons Chemical group 0.000 description 15
230000035699 permeability Effects 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 14
-1 polyethylene Polymers 0.000 description 13
239000000758 substrate Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 12
125000004433 nitrogen atom Chemical group N* 0.000 description 12
125000004430 oxygen atom Chemical group O* 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
239000012153 distilled water Substances 0.000 description 9
230000007717 exclusion Effects 0.000 description 9
239000010408 film Substances 0.000 description 9
238000001223 reverse osmosis Methods 0.000 description 9
239000010409 thin film Substances 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229920001577 copolymer Polymers 0.000 description 8
239000000463 material Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000004745 nonwoven fabric Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
125000002723 alicyclic group Chemical group 0.000 description 6
150000003863 ammonium salts Chemical class 0.000 description 6
125000003710 aryl alkyl group Chemical group 0.000 description 6
238000001879 gelation Methods 0.000 description 6
125000005842 heteroatom Chemical group 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
125000000896 monocarboxylic acid group Chemical group 0.000 description 6
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
239000000499 gel Substances 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000003014 ion exchange membrane Substances 0.000 description 5
239000011148 porous material Substances 0.000 description 5
239000011550 stock solution Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
125000004434 sulfur atom Chemical group 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
229920002873 Polyethylenimine Polymers 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
238000000576 coating method Methods 0.000 description 4
238000005056 compaction Methods 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
238000000502 dialysis Methods 0.000 description 4
229920001519 homopolymer Polymers 0.000 description 4
239000012433 hydrogen halide Substances 0.000 description 4
229910000039 hydrogen halide Inorganic materials 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 3
REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000007824 aliphatic compounds Chemical class 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
150000008040 ionic compounds Chemical class 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910001961 silver nitrate Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
125000000542 sulfonic acid group Chemical group 0.000 description 3
238000004448 titration Methods 0.000 description 3
CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 2
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
XCENPWBBAXQVCG-UHFFFAOYSA-N 4-phenylpiperidine-4-carbaldehyde Chemical compound C=1C=CC=CC=1C1(C=O)CCNCC1 XCENPWBBAXQVCG-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
229920002845 Poly(methacrylic acid) Polymers 0.000 description 2
229910006080 SO2X Inorganic materials 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
125000002015 acyclic group Chemical group 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910001413 alkali metal ion Inorganic materials 0.000 description 2
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 2
150000001449 anionic compounds Chemical class 0.000 description 2
150000007514 bases Chemical class 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000002843 carboxylic acid group Chemical group 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
YSAVZVORKRDODB-WDSKDSINSA-N diethyl tartrate Chemical compound CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC YSAVZVORKRDODB-WDSKDSINSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
125000004970 halomethyl group Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
229910001412 inorganic anion Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
238000005259 measurement Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
150000002891 organic anions Chemical class 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
239000005416 organic matter Substances 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000012466 permeate Substances 0.000 description 2
229920002755 poly(epichlorohydrin) Polymers 0.000 description 2
229920000768 polyamine Polymers 0.000 description 2
239000005020 polyethylene terephthalate Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000002759 woven fabric Substances 0.000 description 2
OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
CBECDWUDYQOTSW-UHFFFAOYSA-N 2-ethylbut-3-enal Chemical compound CCC(C=C)C=O CBECDWUDYQOTSW-UHFFFAOYSA-N 0.000 description 1
VFZIDRLOGFKNAM-UHFFFAOYSA-N 3,5-dicarbonochloridoylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 VFZIDRLOGFKNAM-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
229920004934 Dacron® Polymers 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
QGLBZNZGBLRJGS-UHFFFAOYSA-N Dihydro-3-methyl-2(3H)-furanone Chemical compound CC1CCOC1=O QGLBZNZGBLRJGS-UHFFFAOYSA-N 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical group NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
ZDGWGNDTQZGISB-UHFFFAOYSA-N acetic acid;perchloric acid Chemical compound CC(O)=O.OCl(=O)(=O)=O ZDGWGNDTQZGISB-UHFFFAOYSA-N 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
125000004018 acid anhydride group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
150000001334 alicyclic compounds Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910001508 alkali metal halide Inorganic materials 0.000 description 1
150000008045 alkali metal halides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001615 alkaline earth metal halide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000002009 alkene group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical class [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical group 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
125000000732 arylene group Chemical group 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000003180 beta-lactone group Chemical group 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000005266 casting Methods 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000010612 desalination reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
PVRATXCXJDHJJN-UHFFFAOYSA-N dimethyl 2,3-dihydroxybutanedioate Chemical compound COC(=O)C(O)C(O)C(=O)OC PVRATXCXJDHJJN-UHFFFAOYSA-N 0.000 description 1
YIOJGTBNHQAVBO-UHFFFAOYSA-N dimethyl-bis(prop-2-enyl)azanium Chemical compound C=CC[N+](C)(C)CC=C YIOJGTBNHQAVBO-UHFFFAOYSA-N 0.000 description 1
GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 1
238000010889 donnan-equilibrium Methods 0.000 description 1
238000000909 electrodialysis Methods 0.000 description 1
238000000635 electron micrograph Methods 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
239000004744 fabric Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
125000005067 haloformyl group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000007654 immersion Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000010406 interfacial reaction Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
150000002605 large molecules Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229920000083 poly(allylamine) Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000007921 spray Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
238000000108 ultra-filtration Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

Manufacture Of Macromolecular Shaped Articles (AREA)

JP56004949A 1981-01-19 1981-01-19 Ion-permeable amphoteric composite membrane Granted JPS57119928A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP56004949A JPS57119928A (en)	1981-01-19	1981-01-19	Ion-permeable amphoteric composite membrane

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP56004949A JPS57119928A (en)	1981-01-19	1981-01-19	Ion-permeable amphoteric composite membrane

Publications (2)

Publication Number	Publication Date
JPS57119928A JPS57119928A (en)	1982-07-26
JPS6251297B2 true JPS6251297B2 (fr)	1987-10-29

Family

ID=11597817

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP56004949A Granted JPS57119928A (en)	1981-01-19	1981-01-19	Ion-permeable amphoteric composite membrane

Country Status (1)

Country	Link
JP (1)	JPS57119928A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2016024465A1 (fr) *	2014-08-14	2016-02-18	富士フイルム株式会社	Film polymère fonctionnel, empilage ou dispositif pourvu du film polymère fonctionnel et procédé de production du film polymère fonctionnel
WO2016024464A1 (fr) *	2014-08-14	2016-02-18	富士フイルム株式会社	Film fonctionnel polymère, procédé de production associé, et empilement ou dispositif pourvu d'un film fonctionnel polymère

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57125223A (en) *	1981-01-27	1982-08-04	Teijin Ltd	Amphoteric composite membrane with ion permeability

1981
- 1981-01-19 JP JP56004949A patent/JPS57119928A/ja active Granted

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2016024465A1 (fr) *	2014-08-14	2016-02-18	富士フイルム株式会社	Film polymère fonctionnel, empilage ou dispositif pourvu du film polymère fonctionnel et procédé de production du film polymère fonctionnel
WO2016024464A1 (fr) *	2014-08-14	2016-02-18	富士フイルム株式会社	Film fonctionnel polymère, procédé de production associé, et empilement ou dispositif pourvu d'un film fonctionnel polymère
JPWO2016024464A1 (ja) *	2014-08-14	2017-07-20	富士フイルム株式会社	高分子機能性膜、その製造方法および高分子機能性膜を備えたスタックもしくは装置

Also Published As

Publication number	Publication date
JPS57119928A (en)	1982-07-26

Publication	Publication Date	Title
US4360434A (en)	1982-11-23	Amphoteric ion-permeable composite membrane
EP0056175B1 (fr)	1985-05-02	Membrane perméable composée d'ions et son utilisation dans les procédés de séparation
US4388189A (en)	1983-06-14	Process for preparation of improved semipermeable composite membranes
US4265745A (en)	1981-05-05	Permselective membrane
EP0165077B2 (fr)	1998-02-04	Membranes composites semi-perméables de polysulfone sulfoné
EP2801401B1 (fr)	2018-12-12	Membrane d'osmose inverse remarquablement résistante à la contamination et son procédé de fabrication
US4990252A (en)	1991-02-05	Stable membranes from sulfonated polyarylethers
JP2694341B2 (ja)	1997-12-24	改良された耐酸化性膜およびその製造方法
JPH0138522B2 (fr)	1989-08-15
EP0316525A2 (fr)	1989-05-24	Membranes de polyamide pour l'osmose inverse
JPH0474043B2 (fr)	1992-11-25
WO2021128886A1 (fr)	2021-07-01	Procédé de préparation de membrane de nanofiltration, et membrane de nanofiltration préparée à l'aide dudit procédé
JP6312148B2 (ja)	2018-04-18	高性能の正荷電複合膜及びそれらをナノろ過プロセスに用いる使用
JPS6251297B2 (fr)	1987-10-29
CN115814618A (zh)	2023-03-21	改性基膜的制备方法、复合纳滤膜的制备方法及复合纳滤膜
JP3646362B2 (ja)	2005-05-11	半透膜およびその製造方法
CN116850791B (zh)	2023-12-01	一种反渗透膜及其制备方法
JPS6295104A (ja)	1987-05-01	複合半透膜及びその製造方法
JPS6240041B2 (fr)	1987-08-26
JPH0563209B2 (fr)	1993-09-10
JPS621411B2 (fr)	1987-01-13
JPS6249912A (ja)	1987-03-04	微孔性膜の製造方法
JPH05293345A (ja)	1993-11-09	半透性複合膜
JPH0510967B2 (fr)	1993-02-12
JPH0119922B2 (fr)	1989-04-13