JP2016539787A - 亜硝酸で後処理される複合ポリアミド膜 - Google Patents
亜硝酸で後処理される複合ポリアミド膜 Download PDFInfo
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- JP2016539787A JP2016539787A JP2016533194A JP2016533194A JP2016539787A JP 2016539787 A JP2016539787 A JP 2016539787A JP 2016533194 A JP2016533194 A JP 2016533194A JP 2016533194 A JP2016533194 A JP 2016533194A JP 2016539787 A JP2016539787 A JP 2016539787A
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- Prior art keywords
- acid
- monomer
- polyfunctional
- thin film
- polyamide layer
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- 239000012528 membrane Substances 0.000 title claims abstract description 81
- 239000004952 Polyamide Substances 0.000 title claims abstract description 73
- 229920002647 polyamide Polymers 0.000 title claims abstract description 73
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 239000002131 composite material Substances 0.000 title claims abstract description 20
- 239000000178 monomer Substances 0.000 claims abstract description 78
- -1 arene compound Chemical class 0.000 claims abstract description 47
- 239000002253 acid Substances 0.000 claims abstract description 39
- 150000001266 acyl halides Chemical class 0.000 claims abstract description 38
- 150000001412 amines Chemical class 0.000 claims abstract description 29
- 239000010409 thin film Substances 0.000 claims abstract description 27
- 125000000524 functional group Chemical group 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims abstract description 13
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 9
- 239000010452 phosphate Substances 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 17
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 abstract description 3
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 48
- 238000011282 treatment Methods 0.000 description 19
- 239000012634 fragment Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 14
- 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 description 13
- 229940018564 m-phenylenediamine Drugs 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000004332 silver Substances 0.000 description 11
- 229910052709 silver Inorganic materials 0.000 description 11
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001728 nano-filtration Methods 0.000 description 7
- 229920002492 poly(sulfone) Polymers 0.000 description 7
- 238000001223 reverse osmosis Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 238000000197 pyrolysis Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 5
- 125000000777 acyl halide group Chemical group 0.000 description 5
- 150000007942 carboxylates Chemical class 0.000 description 5
- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 230000004907 flux Effects 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000012454 non-polar solvent Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 150000003141 primary amines Chemical group 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000012695 Interfacial polymerization Methods 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- RFBZPOTVVHLWBP-UHFFFAOYSA-N 11-chloro-11-oxoundecanoic acid Chemical compound OC(=O)CCCCCCCCCC(Cl)=O RFBZPOTVVHLWBP-UHFFFAOYSA-N 0.000 description 2
- LDQMZKBIBRAZEA-UHFFFAOYSA-N 2,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(N)=C1 LDQMZKBIBRAZEA-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- RJHRQMQWMHKSOY-UHFFFAOYSA-N 3,5-dicarbonochloridoylbenzoic acid Chemical compound OC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 RJHRQMQWMHKSOY-UHFFFAOYSA-N 0.000 description 2
- ZCLXQTGLKVQKFD-UHFFFAOYSA-N 3-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1 ZCLXQTGLKVQKFD-UHFFFAOYSA-N 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- YJKJKJNKFIDCMN-UHFFFAOYSA-N 6-chloro-6-oxohexanoic acid Chemical compound OC(=O)CCCCC(Cl)=O YJKJKJNKFIDCMN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 101710134784 Agnoprotein Proteins 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229960004909 aminosalicylic acid Drugs 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- JSYBAZQQYCNZJE-UHFFFAOYSA-N benzene-1,2,4-triamine Chemical compound NC1=CC=C(N)C(N)=C1 JSYBAZQQYCNZJE-UHFFFAOYSA-N 0.000 description 2
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002338 electrophoretic light scattering Methods 0.000 description 2
- 238000009501 film coating Methods 0.000 description 2
- 239000007888 film coating Substances 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- 238000001471 micro-filtration Methods 0.000 description 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
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- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- UKISWDCMNXICCV-UHFFFAOYSA-N 1-phenyl-2-propylbenzene;phosphoric acid Chemical compound OP(O)(O)=O.CCCC1=CC=CC=C1C1=CC=CC=C1 UKISWDCMNXICCV-UHFFFAOYSA-N 0.000 description 1
- QLDZETGUBDKZAV-UHFFFAOYSA-N 12-chloro-12-oxododecanoic acid Chemical compound OC(=O)CCCCCCCCCCC(Cl)=O QLDZETGUBDKZAV-UHFFFAOYSA-N 0.000 description 1
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 1
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 1
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- QXSKFLYCTIMTEU-UHFFFAOYSA-N 2,4-dicarbonochloridoylcyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CC(C(Cl)=O)CC1C(Cl)=O QXSKFLYCTIMTEU-UHFFFAOYSA-N 0.000 description 1
- LQACMMHGSYXMHY-UHFFFAOYSA-N 2-(2,4-dicarbonochloridoylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C(Cl)=O)C=C1C(Cl)=O LQACMMHGSYXMHY-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- JDGZONSWIMFPDO-UHFFFAOYSA-N 2-(2-carboxy-4-hydroxyphenyl)-5-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1C1=CC=C(O)C=C1C(O)=O JDGZONSWIMFPDO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QHXWVACOZJQROG-UHFFFAOYSA-N 2-(3,5-dicarbonochloridoylanilino)acetic acid Chemical compound OC(=O)CNC1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 QHXWVACOZJQROG-UHFFFAOYSA-N 0.000 description 1
- NVUJTTGXXGPDJC-UHFFFAOYSA-N 2-(3,5-dicarbonochloridoylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 NVUJTTGXXGPDJC-UHFFFAOYSA-N 0.000 description 1
- IEOJLOOURBMYCG-UHFFFAOYSA-N 2-(3-carbonochloridoylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC(C(Cl)=O)=C1 IEOJLOOURBMYCG-UHFFFAOYSA-N 0.000 description 1
- KLSMJBWQMULWRH-UHFFFAOYSA-N 2-[(1,3-dioxo-2-benzofuran-5-carbonyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 KLSMJBWQMULWRH-UHFFFAOYSA-N 0.000 description 1
- MWAGGKKAIHLNMM-UHFFFAOYSA-N 2-[(1,3-dioxo-2-benzofuran-5-yl)oxy]acetic acid Chemical compound OC(=O)COC1=CC=C2C(=O)OC(=O)C2=C1 MWAGGKKAIHLNMM-UHFFFAOYSA-N 0.000 description 1
- HIVUAOXLSJITPA-UHFFFAOYSA-N 2-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C(N)=CC=C21 HIVUAOXLSJITPA-UHFFFAOYSA-N 0.000 description 1
- RSWBDNVBJPQFAN-UHFFFAOYSA-N 2-amino-6-hydroxybenzenesulfonic acid Chemical compound NC1=CC=CC(O)=C1S(O)(=O)=O RSWBDNVBJPQFAN-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 1
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 description 1
- 125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 description 1
- BTPBBMFUXJXDGU-UHFFFAOYSA-N 3,5-bis(butoxycarbonyloxycarbonyl)benzoic acid Chemical compound CCCCOC(=O)OC(=O)C1=CC(C(O)=O)=CC(C(=O)OC(=O)OCCCC)=C1 BTPBBMFUXJXDGU-UHFFFAOYSA-N 0.000 description 1
- HQURVGSRQBOZEX-UHFFFAOYSA-N 3,5-diamino-2-hydroxybenzoic acid Chemical compound NC1=CC(N)=C(O)C(C(O)=O)=C1 HQURVGSRQBOZEX-UHFFFAOYSA-N 0.000 description 1
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01D67/0002—Organic membrane manufacture
- B01D67/0006—Organic membrane manufacture by chemical reactions
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
- B01D69/1251—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction by interfacial polymerisation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/56—Polyamides, e.g. polyester-amides
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/10—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by other chemical means
- B05D3/107—Post-treatment of applied coatings
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- General Chemical & Material Sciences (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
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Abstract
多孔質支持体及び薄フィルムポリアミド層を含む複合ポリアミド膜を作製するための方法であって、本方法は、i)多官能性アミンモノマーを含む極性溶液及び多官能性ハロゲン化アシルモノマーを含む非極性溶液を多孔質支持体の表面に適用し、モノマーを界面重合して、薄フィルムポリアミド層を形成することと、ii)薄フィルムポリアミド層を多官能性アレーン化合物で処理することと、iii)薄フィルムポリアミド層を亜硝酸に曝露することと、を含み、該極性及び非極性溶液は、下記、すなわち、(A)該溶液のうちの少なくとも一方が、式Iによって表されるトリ−ヒドロカルビルホスフェート化合物をさらに含む、ならびに(B)該非極性溶液が、少なくとも1つのカルボン酸官能基またはその塩及び少なくとも1つのアミン反応性官能基で置換される、C2−C20炭化水素部分を含む酸含有モノマーをさらに含む、のうちの少なくとも一方をさらに含む。
Description
複合ポリアミド膜は、様々な流体分離において使用される。1つの一般的な部類の膜は、「薄フィルム」ポリアミド層でコーティングされた多孔質支持体を含む。薄フィルム層は、非混和性溶液から経時的に支持体上にコーティングされる多官能性アミン(例えば、m−フェニレンジアミン)モノマーと多官能性ハロゲン化アシル(例えば、トリメソイルクロライド)モノマーとの間の界面重縮合反応によって形成され得、例えば、Cadotteに対する米国特許第4277344号を参照されたい。様々な構成物質が、コーティング溶液のうちの一方または両方に添加されて、膜性能を改善し得る。例えば、Cadotteに対する米国特許第4259183号は、二官能性及び三官能性ハロゲン化アシルモノマー、例えば、トリメソイルクロライドを伴うイソフタロイルクロライドまたはテレフタロイルクロライド、の組み合わせの使用を記載する。国際公開第2012/102942号、国際公開第2012/102943号、国際公開第2012/102944号、国際公開第2013/048765号、及び国際公開第2013/103666号は、Mickolsに対する米国特許第6878278号に記載されるトリ−ヒドロカルビルホスフェート化合物の添加と組み合わせて、カルボン酸官能基及びアミン反応性官能基を含む様々なモノマーの添加を記載する。米国特許第2011/0049055号は、スルホニル、スルフィニル、スルフェニル、スルフリル、ホスホリル、ホスホニル、ホスフィニル、チオホスホリル、チオホスホニル、及びハロゲン化カルボニルに由来する部分の添加を記載する。米国特許第2009/0272692号、米国特許第2012/0261344号、及び米国特許第8177978号は、様々な多官能性ハロゲン化アシル及びそれらの対応する部分的に加水分解された対応物の使用を記載する。Cadotteに対する米国特許第4812270号及び米国特許第4888116号(国際公開第2013/047398号、米国特許第2013/0256215、米国特許第2013/0126419号、米国特許第2012/0305473号、米国特許第2012/0261332号、及び米国特許第2012/0248027号もまた参照)は、リン酸または亜硝酸を有する膜の後処理を記載する。研究は、膜性能をさらに改善するモノマー、添加剤、及び後処理の新たな組み合わせを求めて継続している。
i)多官能性アミンモノマーを含む極性溶液及び多官能性ハロゲン化アシルモノマーを含む非極性溶液を多孔質支持体の表面に適用し、該モノマーを界面重合して、薄フィルムポリアミド層を形成するステップと、
ii)薄フィルムポリアミド層を、下記の4つの官能基、すなわち、
(a)−NR4R5及び−OHから選択される第1の官能基(w)、
(b)−NR4R5、−OH、−COOH、及び−SO3Hから選択される第2の官能基(x)、
(c)−H、−NR4R5、−OH、−COOH、及び−SO3Hから選択される第3の官能基(y)、
(d)−H、−CH3、−NR4R5、−OH、−COOH、及び−SO3Hから選択される第4の官能基(z)、
[式中、(R4)及び(R5)は独立して、−H、及び1〜10個の炭素原子を含むヒドロカルビル基から選択される]で総じて置換される1つまたは2つのベンゼン環を含む多官能性アレーン化合物で処理するステップと、
iii)薄フィルムポリアミド層を亜硝酸に曝露するステップと、を含み、
該極性及び非極性溶液は、下記、すなわち、
(A)該溶液のうちの少なくとも一方が、式I、
式中、R1、R2、及びR3が独立して、水素、及び1〜10個の炭素原子を含むヒドロカルビル基から選択されるが、但し、R1、R2、及びR3のうちの1つよりも多くが水素であることはないものとする、ならびに
(B)該非極性溶液が、少なくとも1つのカルボン酸官能基またはそれらの塩、ならびにハロゲン化アシル、ハロゲン化スルホニル、及び無水物から選択される少なくとも1つのアミン反応性官能基で置換される、C2−C20炭化水素部分を含む、酸含有モノマーをさらに含み、該酸含有モノマーが、多官能性ハロゲン化アシルモノマーと明確に異なる、のうちの少なくとも一方をさらに含む。
式中、「P」は、亜リン酸であり、「O」は、酸素であり、R1、R2、及びR3は独立して、水素、及び1〜10個の炭素原子を含むヒドロカルビル基から選択されるが、但し、R1、R2、及びR3のうちの1つよりも多くが水素であることはないものとする。R1、R2、及びR3は、好ましくは、独立して、脂肪族基及び芳香族基から選択される。適用可能な脂肪族基は、分枝状及び非分枝状種の両方、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、ペンチル、2−ペンチル、3−ペンチルを含む。適用可能な環状基は、シクロペンチル及びシクロヘキシルを含む。適用可能な芳香族基は、フェニル及びナフチル基を含む。環状基及び芳香族基は、脂肪族連結基、例えば、メチル、エチルなどを手段として、リン原子に結合され得る。前述の脂肪族基及び芳香族基は、非置換であり得るか、または置換され得(例えば、メチル、エチル、プロピル、ヒドロキシル、アミド、エーテル、スルホン、カルボニル、エステル、シアン化物、ニトリル、イソシアネート、ウレタン、β−ヒドロキシエステルなどで置換される)、しかしながら、3〜10個の炭素原子を有する非置換アルキル基が好ましい。トリ−ヒドロカルビルホスフェート化合物の特定の例としては、トリエチルホスフェート、トリプロピルホスフェート、トリブチルホスフェート、トリペンチルホスフェート、トリヘキシルホスフェート、トリフェニルホスフェート、プロピルビフェニルホスフェート、ジブチルフェニルホスフェート、ブチルジエチルホスフェート、ジブチル水素ホスフェート、ブチルヘプチル水素ホスフェート、及びブチルヘプチルヘキシルホスフェートが挙げられる。選択される特定の化合物は、それが適用される溶液に少なくとも部分的に溶解できるべきである。追加の例としては、米国特許第6878278号、米国特許第6723241号、米国特許第6562266号、及び米国特許第6337018号に記載される化合物がある。
式中、Aは、酸素(例えば、−O−)、アミノ(−N(R)−)(式中、Rは、1〜6個の炭素原子を有する炭化水素基、例えば、アリール、シクロアルキル、アルキル(置換または非置換であるが、好ましくはハロゲン基及びカルボキシル基などの置換基を伴うか、または伴わない1〜3個の炭素原子を有するアルキル)から選択される)、アミド(−C(O)N(R))−(炭素または窒素のいずれかが、芳香族環と結合し、Rは前に定義した通りである)、カルボニル(−C(O)−)、スルホニル(−SO2−)から選択されるか、または存在せず(例えば、式IIIで示される通り)、nは1〜6の整数であるか、または全基はアリール基であり、Zは、ハロゲン化アシル、ハロゲン化スルホニル、及び無水物(好ましくはハロゲン化アシル)から選択されるアミン反応性官能基であり、Z’は、水素及びカルボン酸と共に、Zによって記載される官能基から選択される。Z及びZ’は独立して、環上のA置換基に対するメタまたはオルトに配置され得る。実施形態の群において、nは1または2である。さらに別の実施形態の群において、Z及びZ’の両方は、両方とも同じである(例えば、両方ハロゲン化アシル基)。別の実施形態の群において、Aは1〜3個の炭素原子を有するアルキル及びアルコキシ基から選択される。非限定的な代表的な種は、2−(3,5−ビス(クロロカルボニル)フェノキシ)酢酸、3−(3,5−ビス(クロロカルボニル)フェニル)プロパン酸、2−((1,3−ジオキソ−1,3−ジヒドロイソベンゾフラン−5−イル)オキシ)酢酸、3−(1,3−ジオキソ−1,3−ジヒドロイソベンゾフラン−5−イル)プロパン酸、2−(3−(クロロカルボニル)フェノキシ)酢酸、3−(3−(クロロカルボニル)フェニル)プロパン酸、3−((3,5ビス(クロロカルボニル)フェニル)スルホニル)プロパン酸、3−((3−(クロロカルボニル)フェニル)スルホニル)プロパン酸、3−((1,3−ジオキソ−1,3−ジヒドロイソベンゾフラン−5−イル)スルホニル)プロパン酸、3−((1,3−ジオキソ−1,3−ジヒドロイソベンゾフラン−5−イル)アミノ)プロパン酸、3−((1,3−ジオキソ−1,3−ジヒドロイソベンゾフラン−5−イル)(エチル)アミノ)プロパン酸、3−((3,5−ビス(クロロカルボニル)フェニル)アミノ)プロパン酸、3−((3,5−ビス(クロロカルボニル)フェニル)(エチル)アミノ)プロパン酸、4−(4−(クロロカルボニル)フェニル)−4−オキソブタン酸、4−(3,5−ビス(クロロカルボニル)フェニル)−4−オキソブタン酸、4−(1,3−ジオキソ−1,3−ジヒドロイソベンゾフラン−5−イル)−4−オキソブタン酸、2−(3,5−ビス(クロロカルボニル)フェニル)酢酸、2−(2,4−ビス(クロロカルボニル)フェノキシ)酢酸、4−((3,5−ビス(クロロカルボニル)フェニル)アミノ)−4−オキソブタン酸、2−((3,5−ビス(クロロカルボニル)フェニル)アミノ)酢酸、2−(N−(3,5−ビス(クロロカルボニル)フェニル)アセトアミド)酢酸、2,2’−((3,5−ビス(クロロカルボニル)フェニルアザンジイル)ジ酢酸、N−[(1,3−ジヒドロ−1,3−ジオキソ−5−イソベンゾフラニル)カルボニル]−グリシン、4−[[(1,3−ジヒドロ−1,3−ジオキソ−5−イソベンゾフラニル)カルボニル]アミノ]−安息香酸、1,3−ジヒドロ−1,3−ジオキソ−4−イソベンゾフランプロパン酸、5−[[(1,3−ジヒドロ−1,3−ジオキソ−5−イソベンゾフラニル)カルボニル]アミノ]−1,3−ベンゼンジカルボン酸、及び3−[(1,3−ジヒドロ−1,3−ジオキソ−5−イソベンゾフラニル)スルホニル]−安息香酸を含む。
式中、カルボン酸基は、フェニル環上のメタ、パラ、またはオルトに位置し得る。
式中、Xはハロゲン(好ましくは塩素)であり、nは1〜20、好ましくは2〜10の整数である。代表的な種は、4−(クロロカルボニル)ブタン酸、5−(クロロカルボニル)ペンタン酸、6−(クロロカルボニル)ヘキサン酸、7−(クロロカルボニル)ヘプタン酸、8−(クロロカルボニル)オクタン酸、9−(クロロカルボニル)ノナン酸、10−(クロロカルボニル)デカン酸、11−クロロ−11−オキソウンデカン酸、12−クロロ−12−オキソドデカン酸、3−(クロロカルボニル)シクロブタンカルボン酸、3−(クロロカルボニル)シクロペンタンカルボン酸、2,4−ビス(クロロカルボニル)シクロペンタンカルボン酸、3,5−ビス(クロロカルボニル)シクロヘキサンカルボン酸、及び4−(クロロカルボニル)シクロヘキサンカルボン酸を含む。ハロゲン化アシル基及びカルボン酸基は末端位置に示されるが、一方または両方が、脂肪族鎖に沿った代替的な位置に位置してもよい。式(IV)には示されないが、酸含有モノマーは、追加のカルボン酸基及びハロゲン化アシル基を含み得る。
a)−NR4R5(アミン)及び−OH(ヒドロキシル)から選択される第1の官能基(w)、
b)−NR4R5(アミン)、−OH(ヒドロキシル)、−COOH(カルボン酸)、及び−SO3H(スルホン酸)から選択される第2の官能基(x)、ならびに
c)−H(水素)、−NR4R5(アミン)、−OH(ヒドロキシル)、−COOH(カルボン酸)、及び−SO3H(スルホン酸)から選択される第3の官能基(y)、
d)−H(水素)、−CH3(メチル)、−NR4R5(アミン)、−OH(ヒドロキシル)、−COOH(カルボン酸)、及び−SO3H(スルホン酸)から選択される第4の官能基(z)で総じて置換される、
(融合しているか、または環間の直接結合、1〜6個の炭素原子を含むアルキレン基、及び1〜6個の炭素原子を含むオキシアルキレン基によって結合(L)され得る)1個または2個(好ましくは1個)のベンゼン環を含む、多官能性アレーン化合物で処理され、
(R4)及び(R5)は独立して、−H、及び1〜10個の炭素原子を含むヒドロカルビル基(好ましくは、1〜4個の炭素原子を有するアルキル基)から選択される。ベンゼン環(複数可)は、(w)、(x)、(y)、及び(z)に関して上に列挙されるもの、またはメチル基、エチル基、及びハロゲン等の他の基を含む追加の官能基で、さらに置換され得る。置換基(w)、(x)、(y)、及び(z)は、互いに対して、メタ、オルトまたはパラに位置し得る。適用可能な多官能性アレーン化合物は、式VII〜IX、
式中、(L)は、環間の直接結合、1〜6個の炭素原子を含むアルキレン基、及び1〜6個の炭素原子を含むオキシアルキレン基から選択される。
a) (w)は、−NR4R5及び−OHから選択され、
b) (x)は、−COOH及び−SO3Hから選択され、
c) (y)は、−H、−COOH、及び−SO3Hから選択され、
d) (z)は、−H、−CH、−COOH、及び−SO3Hから選択される。
a) (w)が、−NR4R5から選択され、
b) (x)が、−OHから選択され、
c) (y)が、−H、−COOH、及び−SO3Hから選択され、ならびに
d) (z)が、−H、−CH、−COOH、及び−SO3Hから選択される、架橋剤である。
Claims (10)
- 多孔質支持体及び薄フィルムポリアミド層を含む複合ポリアミド膜を作製するための方法であって、
i)多官能性アミンモノマーを含む極性溶液及び多官能性ハロゲン化アシルモノマーを含む非極性溶液を多孔質支持体の表面に適用し、前記モノマーを界面重合して、薄フィルムポリアミド層を形成することと、
ii)前記薄フィルムポリアミド層を、以下の4つの官能基、すなわち
(a)−NR4R5及び−OHから選択される第1の官能基(w)、
(b)−NR4R5、−OH、−COOH、及び−SO3Hから選択される第2の官能基(x)、
(c)−H、−NR4R5、−OH、−COOH、及び−SO3Hから選択される第3の官能基(y)、
(d)−H、−CH3、−NR4R5、−OH、−COOH、及び−SO3Hから選択される第4の官能基(z)、
[式中、(R4)及び(R5)は独立して、−H、及び1〜10個の炭素原子を含むヒドロカルビル基から選択される]で総じて置換される1個または2個のベンゼン環を含む多官能性アレーン化合物で処理することと、
iii)前記薄フィルムポリアミド層を亜硝酸に曝露することと、を含み、
前記極性及び非極性溶液は、下記、すなわち、
(A)前記溶液のうちの少なくとも一方が、式I、
式中、R1、R2、及びR3が独立して、水素、及び1〜10個の炭素原子を含むヒドロカルビル基から選択されるが、但し、R1、R2、及びR3のうちの1つよりも多くが水素であることはないものとする、ならびに
(B)前記非極性溶液が、少なくとも1つのカルボン酸官能基またはそれらの塩、ならびにハロゲン化アシル、ハロゲン化スルホニル、及び無水物から選択される少なくとも1つのアミン反応性官能基で置換される、C2−C20炭化水素部分を含む、酸含有モノマーをさらに含み、前記酸含有モノマーが、前記多官能性ハロゲン化アシルモノマーと明確に異なる、のうちの少なくとも一方をさらに含む、前記方法。 - (A)前記溶液のうちの少なくとも一方が、式I、
式中、R1、R2、及びR3が独立して、水素、及び1〜10個の炭素原子を含むヒドロカルビル基から選択されるが、但し、R1、R2、及びR3のうちの1つよりも多くが水素であることはないものとし、かつ
(B)前記非極性溶液が、少なくとも1つのカルボン酸官能基またはそれらの塩、ならびにハロゲン化アシル、ハロゲン化スルホニル、及び無水物から選択される少なくとも1つのアミン反応性官能基で置換される、C2−C20炭化水素部分を含む、酸含有モノマーを含み、酸含有モノマーが、前記多官能性ハロゲン化アシルモノマーと明確に異なる、請求項1に記載の前記方法。 - 前記非極性溶液は、アレーン部分を含む酸含有モノマーを含む、請求項1に記載の前記方法。
- 前記非極性溶液は、脂肪族部分を含む酸含有モノマーを含む、請求項1に記載の前記方法。
- 前記非極性溶液は、少なくとも2つのアミン反応性官能基を含む酸含有モノマーを含む、請求項1に記載の前記方法。
- 前記薄フィルムポリアミド層は、前記薄フィルムポリアミド層を亜硝酸に前記曝露するステップより前に、RBSによって測定するとき、pH9.5で少なくとも0.18モル/kgの解離したカルボン酸含有量を有する、請求項1に記載の前記方法。
- (w)は、−NR4R5及び−OHから選択され、
(x)は、−COOH及び−SO3Hから選択され、
(y)は、−H、−COOH、及び−SO3Hから選択され、
(z)は、−H、−CH、−COOH、及び−SO3Hから選択され、
(R4)及び(R5)は独立して、−H、及び1〜10個の炭素原子を含むヒドロカルビル基から選択される、請求項1に記載の前記方法。 - (w)は、−NR4R5から選択され、
(x)は、−OHから選択され、
(y)は、−H、−COOH、及び−SO3Hから選択され、
(z)は、−H、−CH、−COOH、及び−SO3Hから選択され、
(R4)及び(R5)は独立して、−H、及び1〜10個の炭素原子を含むヒドロカルビル基から選択される、請求項1に記載の前記方法。 - (w)及び(x)は、−NR4R5から選択され、
(y)及び(z)は、−Hから選択され、
(R4)及び(R5)は独立して、−H、及び1〜10個の炭素原子を含むヒドロカルビル基から選択される、請求項1に記載の前記方法。
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