CN1441693A - 复合膜及其制造方法 - Google Patents
复合膜及其制造方法 Download PDFInfo
- Publication number
- CN1441693A CN1441693A CN01808064A CN01808064A CN1441693A CN 1441693 A CN1441693 A CN 1441693A CN 01808064 A CN01808064 A CN 01808064A CN 01808064 A CN01808064 A CN 01808064A CN 1441693 A CN1441693 A CN 1441693A
- Authority
- CN
- China
- Prior art keywords
- phosphate
- phosphine
- complexing agent
- propyl
- methyl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 69
- 239000012528 membrane Substances 0.000 title claims abstract description 47
- 239000002131 composite material Substances 0.000 title claims abstract description 18
- 239000008139 complexing agent Substances 0.000 claims abstract description 121
- 150000001412 amines Chemical class 0.000 claims abstract description 105
- 239000004952 Polyamide Substances 0.000 claims abstract description 34
- 229920002647 polyamide Polymers 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 343
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 317
- 239000010452 phosphate Substances 0.000 claims description 223
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 207
- -1 carboxylic acid halides Chemical class 0.000 claims description 179
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 171
- 235000011180 diphosphates Nutrition 0.000 claims description 54
- 239000000243 solution Substances 0.000 claims description 49
- 239000007864 aqueous solution Substances 0.000 claims description 25
- 229910052698 phosphorus Inorganic materials 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 17
- 239000011574 phosphorus Substances 0.000 claims description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 16
- 239000011248 coating agent Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 10
- 239000004760 aramid Substances 0.000 claims description 9
- 229920003235 aromatic polyamide Polymers 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052787 antimony Inorganic materials 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229940048084 pyrophosphate Drugs 0.000 claims description 8
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 claims description 7
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims description 7
- 230000000737 periodic effect Effects 0.000 claims description 7
- 229910052711 selenium Inorganic materials 0.000 claims description 7
- 239000011669 selenium Substances 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 229910052785 arsenic Inorganic materials 0.000 claims description 6
- 229910052804 chromium Inorganic materials 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 229910052714 tellurium Inorganic materials 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 238000012695 Interfacial polymerization Methods 0.000 claims description 5
- 150000008301 phosphite esters Chemical class 0.000 claims description 5
- 238000001764 infiltration Methods 0.000 claims description 4
- 239000012466 permeate Substances 0.000 claims description 4
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 4
- 229940005657 pyrophosphoric acid Drugs 0.000 claims description 4
- 229940122361 Bisphosphonate Drugs 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 3
- 150000004663 bisphosphonates Chemical class 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 claims description 3
- 125000005538 phosphinite group Chemical group 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 230000007306 turnover Effects 0.000 claims description 3
- 229910052745 lead Inorganic materials 0.000 claims description 2
- 230000007928 solubilization Effects 0.000 claims description 2
- 238000005063 solubilization Methods 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
- 150000001266 acyl halides Chemical class 0.000 abstract description 22
- 238000001223 reverse osmosis Methods 0.000 abstract description 11
- 230000004907 flux Effects 0.000 abstract 1
- 238000001728 nano-filtration Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 564
- 235000021317 phosphate Nutrition 0.000 description 340
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 122
- 239000007983 Tris buffer Substances 0.000 description 85
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 48
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 48
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 48
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 34
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 33
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 31
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 28
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 26
- 230000004069 differentiation Effects 0.000 description 25
- 150000003839 salts Chemical class 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
- 239000000178 monomer Substances 0.000 description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 238000001035 drying Methods 0.000 description 15
- 150000003014 phosphoric acid esters Chemical class 0.000 description 15
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 12
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 12
- 235000010290 biphenyl Nutrition 0.000 description 11
- 239000004305 biphenyl Substances 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 10
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 8
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 8
- 229940018564 m-phenylenediamine Drugs 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 238000012805 post-processing Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 5
- 239000013626 chemical specie Substances 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 229910052797 bismuth Inorganic materials 0.000 description 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- PHNWGDTYCJFUGZ-UHFFFAOYSA-L hexyl phosphate Chemical compound CCCCCCOP([O-])([O-])=O PHNWGDTYCJFUGZ-UHFFFAOYSA-L 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- YJBMMHPCGWCCOH-UHFFFAOYSA-N octan-3-yl dihydrogen phosphate Chemical compound CCCCCC(CC)OP(O)(O)=O YJBMMHPCGWCCOH-UHFFFAOYSA-N 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229920002492 poly(sulfone) Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- OSRJBXRUXTUMBY-UHFFFAOYSA-N triheptylphosphane Chemical compound CCCCCCCP(CCCCCCC)CCCCCCC OSRJBXRUXTUMBY-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000000777 acyl halide group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 230000000536 complexating effect Effects 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- VEUUGZQJNGFYBU-UHFFFAOYSA-N decan-4-yl dihydrogen phosphate Chemical compound CCCCCCC(CCC)OP(O)(O)=O VEUUGZQJNGFYBU-UHFFFAOYSA-N 0.000 description 3
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- GGKJPMAIXBETTD-UHFFFAOYSA-L heptyl phosphate Chemical compound CCCCCCCOP([O-])([O-])=O GGKJPMAIXBETTD-UHFFFAOYSA-L 0.000 description 3
- AXSGBDGQLKZKQI-UHFFFAOYSA-N hexan-3-yl dihydrogen phosphate Chemical compound CCCC(CC)OP(O)(O)=O AXSGBDGQLKZKQI-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000002452 interceptive effect Effects 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
- STMLQIACVZOCHU-UHFFFAOYSA-N octan-2-yl dihydrogen phosphate Chemical compound CCCCCCC(C)OP(O)(O)=O STMLQIACVZOCHU-UHFFFAOYSA-N 0.000 description 3
- HLHZHCMELZFILJ-UHFFFAOYSA-N octan-4-yl dihydrogen phosphate Chemical compound CCCCC(CCC)OP(O)(O)=O HLHZHCMELZFILJ-UHFFFAOYSA-N 0.000 description 3
- RYIOLWQRQXDECZ-UHFFFAOYSA-N phosphinous acid Chemical compound PO RYIOLWQRQXDECZ-UHFFFAOYSA-N 0.000 description 3
- WDHYRUBXLGOLKR-UHFFFAOYSA-N phosphoric acid;prop-2-enoic acid Chemical compound OC(=O)C=C.OP(O)(O)=O WDHYRUBXLGOLKR-UHFFFAOYSA-N 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229910052706 scandium Inorganic materials 0.000 description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 3
- XGBSCBAEKRHTMZ-UHFFFAOYSA-N trihexan-2-yl phosphate Chemical compound CCCCC(C)OP(=O)(OC(C)CCCC)OC(C)CCCC XGBSCBAEKRHTMZ-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KHCSDAXTRLGATD-UHFFFAOYSA-N CCCCCC(CCC)OP(O)(O)=O Chemical compound CCCCCC(CCC)OP(O)(O)=O KHCSDAXTRLGATD-UHFFFAOYSA-N 0.000 description 2
- GUMDLEUUKYYYJT-UHFFFAOYSA-N CCCCCCCOP(O)(=O)OCC Chemical compound CCCCCCCOP(O)(=O)OCC GUMDLEUUKYYYJT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000370738 Chlorion Species 0.000 description 2
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 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
- FJTUUPVRIANHEX-UHFFFAOYSA-N butan-1-ol;phosphoric acid Chemical compound CCCCO.OP(O)(O)=O FJTUUPVRIANHEX-UHFFFAOYSA-N 0.000 description 2
- SPSGSQIUFBBUIE-UHFFFAOYSA-N butyl methyl hydrogen phosphate Chemical compound CCCCOP(O)(=O)OC SPSGSQIUFBBUIE-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- JAWGVVJVYSANRY-UHFFFAOYSA-N cobalt(3+) Chemical compound [Co+3] JAWGVVJVYSANRY-UHFFFAOYSA-N 0.000 description 2
- RXROGUYJTMLZHX-UHFFFAOYSA-N decan-5-yl dihydrogen phosphate Chemical compound CCCCCC(OP(O)(O)=O)CCCC RXROGUYJTMLZHX-UHFFFAOYSA-N 0.000 description 2
- DWHUEFYNZKYMMY-UHFFFAOYSA-N decylphosphinic acid Chemical group CCCCCCCCCCP(O)=O DWHUEFYNZKYMMY-UHFFFAOYSA-N 0.000 description 2
- XGARRRXZJOBLNO-UHFFFAOYSA-N decylphosphinous acid Chemical compound CCCCCCCCCCPO XGARRRXZJOBLNO-UHFFFAOYSA-N 0.000 description 2
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 2
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- GBAWQJNHVWMTLU-RQJHMYQMSA-N [(1R,5S)-7-chloro-6-bicyclo[3.2.0]hepta-2,6-dienyl] dimethyl phosphate Chemical compound C1=CC[C@@H]2C(OP(=O)(OC)OC)=C(Cl)[C@@H]21 GBAWQJNHVWMTLU-RQJHMYQMSA-N 0.000 description 1
- PTOIEUWJQMEUQM-UHFFFAOYSA-N [2-(aminomethyl)phenyl]phosphonic acid Chemical group NCC1=CC=CC=C1P(O)(O)=O PTOIEUWJQMEUQM-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- RPHKINMPYFJSCF-UHFFFAOYSA-N benzene-1,3,5-triamine Chemical compound NC1=CC(N)=CC(N)=C1 RPHKINMPYFJSCF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000005605 benzo group Chemical group 0.000 description 1
- LRNMTOCGEKHHAH-UHFFFAOYSA-N butan-2-yl dihydrogen phosphate Chemical compound CCC(C)OP(O)(O)=O LRNMTOCGEKHHAH-UHFFFAOYSA-N 0.000 description 1
- JUCNTEIJIIMFMY-UHFFFAOYSA-N butoxy-octyl-oxophosphanium Chemical compound CCCCCCCC[P+](=O)OCCCC JUCNTEIJIIMFMY-UHFFFAOYSA-N 0.000 description 1
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 1
- HJBHWZGXCLGKHJ-UHFFFAOYSA-N butyl ethyl hexyl phosphate Chemical compound CCCCCCOP(=O)(OCC)OCCCC HJBHWZGXCLGKHJ-UHFFFAOYSA-N 0.000 description 1
- GGSHLKDUFMSOGV-UHFFFAOYSA-N butyl ethyl methyl phosphate Chemical compound CCCCOP(=O)(OC)OCC GGSHLKDUFMSOGV-UHFFFAOYSA-N 0.000 description 1
- DPFMUGMJFGKXCL-UHFFFAOYSA-N butyl ethyl pentyl phosphate Chemical compound CCCCCOP(=O)(OCC)OCCCC DPFMUGMJFGKXCL-UHFFFAOYSA-N 0.000 description 1
- VOSBUBHATVNQIK-UHFFFAOYSA-N butyl ethyl propyl phosphate Chemical compound CCCCOP(=O)(OCC)OCCC VOSBUBHATVNQIK-UHFFFAOYSA-N 0.000 description 1
- ZZTJXBFUYJCWTM-UHFFFAOYSA-N butyl heptyl methyl phosphate Chemical compound CCCCCCCOP(=O)(OC)OCCCC ZZTJXBFUYJCWTM-UHFFFAOYSA-N 0.000 description 1
- GGHNPAHLYPMGCS-UHFFFAOYSA-N butyl hexyl methyl phosphate Chemical compound CCCCCCOP(=O)(OC)OCCCC GGHNPAHLYPMGCS-UHFFFAOYSA-N 0.000 description 1
- AIKSNHCVBLIKQW-UHFFFAOYSA-N butyl methyl octyl phosphate Chemical compound CCCCCCCCOP(=O)(OC)OCCCC AIKSNHCVBLIKQW-UHFFFAOYSA-N 0.000 description 1
- GVEKQFOKDAAWAY-UHFFFAOYSA-N butyl methyl pentyl phosphate Chemical compound CCCCCOP(=O)(OC)OCCCC GVEKQFOKDAAWAY-UHFFFAOYSA-N 0.000 description 1
- TZYXOYUCUPCMHA-UHFFFAOYSA-N butyl methyl propyl phosphate Chemical compound CCCCOP(=O)(OC)OCCC TZYXOYUCUPCMHA-UHFFFAOYSA-N 0.000 description 1
- FWNZSQVVCQVDOJ-UHFFFAOYSA-N butyl octyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCC FWNZSQVVCQVDOJ-UHFFFAOYSA-N 0.000 description 1
- OBUOEEUFMIUOIL-UHFFFAOYSA-N butyl-ethyl-heptylphosphane Chemical compound CCCCCCCP(CC)CCCC OBUOEEUFMIUOIL-UHFFFAOYSA-N 0.000 description 1
- DVQCSQKAKACEGZ-UHFFFAOYSA-N butyl-ethyl-hexylphosphane Chemical compound CCCCCCP(CC)CCCC DVQCSQKAKACEGZ-UHFFFAOYSA-N 0.000 description 1
- GAYBKVDVHBBMFM-UHFFFAOYSA-N butyl-ethyl-octylphosphane Chemical compound CCCCCCCCP(CC)CCCC GAYBKVDVHBBMFM-UHFFFAOYSA-N 0.000 description 1
- YCAOQCOXLTZQCF-UHFFFAOYSA-N butyl-ethyl-pentylphosphane Chemical compound CCCCCP(CC)CCCC YCAOQCOXLTZQCF-UHFFFAOYSA-N 0.000 description 1
- GTFOFESGWQFPGJ-UHFFFAOYSA-N butyl-ethyl-propylphosphane Chemical compound CCCCP(CC)CCC GTFOFESGWQFPGJ-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- DZQISOJKASMITI-UHFFFAOYSA-N decyl-dioxido-oxo-$l^{5}-phosphane;hydron Chemical group CCCCCCCCCCP(O)(O)=O DZQISOJKASMITI-UHFFFAOYSA-N 0.000 description 1
- PIXOLJPRTSVSFL-UHFFFAOYSA-N decylphosphonous acid Chemical compound CCCCCCCCCCP(O)O PIXOLJPRTSVSFL-UHFFFAOYSA-N 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- AJNJYBVMIMKWTP-UHFFFAOYSA-N di(heptan-2-yl)-phenylphosphane Chemical compound CCCCCC(C)P(C(C)CCCCC)C1=CC=CC=C1 AJNJYBVMIMKWTP-UHFFFAOYSA-N 0.000 description 1
- MQBZIDZJUNTDOE-UHFFFAOYSA-N di(heptan-3-yl)-methylphosphane Chemical compound CCCCC(CC)P(C)C(CC)CCCC MQBZIDZJUNTDOE-UHFFFAOYSA-N 0.000 description 1
- PENUQBNEBLSGAK-UHFFFAOYSA-N di(heptan-4-yl)-phenylphosphane Chemical compound CCCC(CCC)P(C(CCC)CCC)C1=CC=CC=C1 PENUQBNEBLSGAK-UHFFFAOYSA-N 0.000 description 1
- OPNLKQPHTFFCSW-UHFFFAOYSA-N di(hexan-2-yl)-phenylphosphane Chemical compound CCCCC(C)P(C(C)CCCC)C1=CC=CC=C1 OPNLKQPHTFFCSW-UHFFFAOYSA-N 0.000 description 1
- LYAXSFGRRWZNLH-UHFFFAOYSA-N di(hexan-3-yl)-phenylphosphane Chemical compound CCCC(CC)P(C(CC)CCC)C1=CC=CC=C1 LYAXSFGRRWZNLH-UHFFFAOYSA-N 0.000 description 1
- JILUVVJYOFGZAU-UHFFFAOYSA-N di(octan-2-yl)-phenylphosphane Chemical compound CCCCCCC(C)P(C(C)CCCCCC)C1=CC=CC=C1 JILUVVJYOFGZAU-UHFFFAOYSA-N 0.000 description 1
- QCXSXQYOHOXWEB-UHFFFAOYSA-N di(octan-3-yl)-phenylphosphane Chemical compound CCCCCC(CC)P(C(CC)CCCCC)C1=CC=CC=C1 QCXSXQYOHOXWEB-UHFFFAOYSA-N 0.000 description 1
- PUIOYIARFPAHRG-UHFFFAOYSA-N di(octan-4-yl)-phenylphosphane Chemical compound CCCCC(CCC)P(C(CCC)CCCC)C1=CC=CC=C1 PUIOYIARFPAHRG-UHFFFAOYSA-N 0.000 description 1
- QKGOFLSXJWNEQU-UHFFFAOYSA-N di(octan-4-yl)phosphane Chemical compound CCCCC(CCC)PC(CCC)CCCC QKGOFLSXJWNEQU-UHFFFAOYSA-N 0.000 description 1
- YICSVBJRVMLQNS-UHFFFAOYSA-N dibutyl phenyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OC1=CC=CC=C1 YICSVBJRVMLQNS-UHFFFAOYSA-N 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- HPGNDWLQFVMVSL-UHFFFAOYSA-N didecylphosphinic acid Chemical group CCCCCCCCCCP(O)(=O)CCCCCCCCCC HPGNDWLQFVMVSL-UHFFFAOYSA-N 0.000 description 1
- UKYYMGKWTRFBOJ-UHFFFAOYSA-N didecylphosphinous acid Chemical compound CCCCCCCCCCP(O)CCCCCCCCCC UKYYMGKWTRFBOJ-UHFFFAOYSA-N 0.000 description 1
- WNBWVMSMEVCXPP-UHFFFAOYSA-N diethoxy-methoxy-sulfanylidene-lambda5-phosphane Chemical compound CCOP(=S)(OC)OCC WNBWVMSMEVCXPP-UHFFFAOYSA-N 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- DHTQKXHLXVUBCF-UHFFFAOYSA-N diethyl phenyl phosphate Chemical compound CCOP(=O)(OCC)OC1=CC=CC=C1 DHTQKXHLXVUBCF-UHFFFAOYSA-N 0.000 description 1
- KTLIMPGQZDZPSB-UHFFFAOYSA-M diethylphosphinate Chemical compound CCP([O-])(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-M 0.000 description 1
- QZGRYBHHJBKFFN-UHFFFAOYSA-N diheptan-2-yl phenyl phosphate Chemical compound CCCCCC(C)OP(=O)(OC(C)CCCCC)OC1=CC=CC=C1 QZGRYBHHJBKFFN-UHFFFAOYSA-N 0.000 description 1
- WGQOQBPSMZCLFN-UHFFFAOYSA-N diheptan-3-yl phenyl phosphate Chemical compound CCCCC(CC)OP(=O)(OC(CC)CCCC)OC1=CC=CC=C1 WGQOQBPSMZCLFN-UHFFFAOYSA-N 0.000 description 1
- HDHASXPRDZUJCF-UHFFFAOYSA-N diheptan-4-yl phenyl phosphate Chemical compound CCCC(CCC)OP(=O)(OC(CCC)CCC)OC1=CC=CC=C1 HDHASXPRDZUJCF-UHFFFAOYSA-N 0.000 description 1
- REKYWQFSUOYXIC-UHFFFAOYSA-N diheptyl(phenyl)phosphane Chemical compound CCCCCCCP(CCCCCCC)C1=CC=CC=C1 REKYWQFSUOYXIC-UHFFFAOYSA-N 0.000 description 1
- XGVCGGYVDCBIQH-UHFFFAOYSA-N diheptylphosphinic acid Chemical group CCCCCCCP(O)(=O)CCCCCCC XGVCGGYVDCBIQH-UHFFFAOYSA-N 0.000 description 1
- MYHCUFHNVQONIR-UHFFFAOYSA-N dihexan-2-yl phenyl phosphate Chemical compound CCCCC(C)OP(=O)(OC(C)CCCC)OC1=CC=CC=C1 MYHCUFHNVQONIR-UHFFFAOYSA-N 0.000 description 1
- JLJBVTLOSXPYDG-UHFFFAOYSA-N dihexan-3-yl phenyl phosphate Chemical compound CCCC(CC)OP(=O)(OC(CC)CCC)OC1=CC=CC=C1 JLJBVTLOSXPYDG-UHFFFAOYSA-N 0.000 description 1
- DQLJOCWRWFJZMD-UHFFFAOYSA-N dihexyl phenyl phosphate Chemical compound CCCCCCOP(=O)(OCCCCCC)OC1=CC=CC=C1 DQLJOCWRWFJZMD-UHFFFAOYSA-N 0.000 description 1
- MRCWFLVFFDEGGJ-UHFFFAOYSA-N dihexyl(phenyl)phosphane Chemical compound CCCCCCP(CCCCCC)C1=CC=CC=C1 MRCWFLVFFDEGGJ-UHFFFAOYSA-N 0.000 description 1
- MPOGRWAICRNMOH-UHFFFAOYSA-N dihexylphosphinous acid Chemical compound CCCCCCP(O)CCCCCC MPOGRWAICRNMOH-UHFFFAOYSA-N 0.000 description 1
- RIEWSWCAHAVEKK-UHFFFAOYSA-N dioctan-2-yl phenyl phosphate Chemical compound CCCCCCC(C)OP(=O)(OC(C)CCCCCC)OC1=CC=CC=C1 RIEWSWCAHAVEKK-UHFFFAOYSA-N 0.000 description 1
- WUKJTCYTWJATLP-UHFFFAOYSA-N dioctan-3-yl phenyl phosphate Chemical compound CCCCCC(CC)OP(=O)(OC(CC)CCCCC)OC1=CC=CC=C1 WUKJTCYTWJATLP-UHFFFAOYSA-N 0.000 description 1
- DMEGVGQMHNHVMU-UHFFFAOYSA-N dioctan-4-yl phenyl phosphate Chemical compound CCCCC(CCC)OP(=O)(OC(CCC)CCCC)OC1=CC=CC=C1 DMEGVGQMHNHVMU-UHFFFAOYSA-N 0.000 description 1
- QHGRPTNUHWYCEN-UHFFFAOYSA-N dioctyl phenyl phosphate Chemical compound CCCCCCCCOP(=O)(OCCCCCCCC)OC1=CC=CC=C1 QHGRPTNUHWYCEN-UHFFFAOYSA-N 0.000 description 1
- HXUARCOTWDKZOU-UHFFFAOYSA-N dioctyl(phenyl)phosphane Chemical compound CCCCCCCCP(CCCCCCCC)C1=CC=CC=C1 HXUARCOTWDKZOU-UHFFFAOYSA-N 0.000 description 1
- BYYQOWAAZOHHFN-UHFFFAOYSA-N dioctylphosphane Chemical compound CCCCCCCCPCCCCCCCC BYYQOWAAZOHHFN-UHFFFAOYSA-N 0.000 description 1
- LRDNYVHXOLIAAL-UHFFFAOYSA-N dipentan-2-yl phenyl phosphate Chemical compound CCCC(C)OP(=O)(OC(C)CCC)OC1=CC=CC=C1 LRDNYVHXOLIAAL-UHFFFAOYSA-N 0.000 description 1
- NWEIRQMBFHIYBF-UHFFFAOYSA-N dipentan-3-yl phenyl phosphate Chemical compound CCC(CC)OP(=O)(OC(CC)CC)OC1=CC=CC=C1 NWEIRQMBFHIYBF-UHFFFAOYSA-N 0.000 description 1
- XGERJGRFYKEESL-UHFFFAOYSA-N dipentyl phenyl phosphate Chemical compound CCCCCOP(=O)(OCCCCC)OC1=CC=CC=C1 XGERJGRFYKEESL-UHFFFAOYSA-N 0.000 description 1
- KUFDFOXPFQCUST-UHFFFAOYSA-N dipentylphosphinic acid Chemical group CCCCCP(O)(=O)CCCCC KUFDFOXPFQCUST-UHFFFAOYSA-N 0.000 description 1
- CYCJADSSNQCEHO-UHFFFAOYSA-N dipentylphosphinous acid Chemical compound CCCCCP(O)CCCCC CYCJADSSNQCEHO-UHFFFAOYSA-N 0.000 description 1
- JIKVJUUIMIGAAO-UHFFFAOYSA-N diphenylphosphinous acid Chemical compound C=1C=CC=CC=1P(O)C1=CC=CC=C1 JIKVJUUIMIGAAO-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- QAZDVMGHQBYZBJ-UHFFFAOYSA-N dipropylphosphinous acid Chemical compound CCCP(O)CCC QAZDVMGHQBYZBJ-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- NJMBXZARVGYNSP-UHFFFAOYSA-N ethyl heptyl hexyl phosphate Chemical compound CCCCCCCOP(=O)(OCC)OCCCCCC NJMBXZARVGYNSP-UHFFFAOYSA-N 0.000 description 1
- YARXZVMNXKHGHL-UHFFFAOYSA-N ethyl heptyl methyl phosphate Chemical compound CCCCCCCOP(=O)(OC)OCC YARXZVMNXKHGHL-UHFFFAOYSA-N 0.000 description 1
- UCIDRXAWOCVRCU-UHFFFAOYSA-N ethyl heptyl pentyl phosphate Chemical compound CCCCCCCOP(=O)(OCC)OCCCCC UCIDRXAWOCVRCU-UHFFFAOYSA-N 0.000 description 1
- HLTMVBAXPFPFLC-UHFFFAOYSA-N ethyl heptyl propyl phosphate Chemical compound CCCCCCCOP(=O)(OCC)OCCC HLTMVBAXPFPFLC-UHFFFAOYSA-N 0.000 description 1
- KKLSTYKNFSNFAF-UHFFFAOYSA-N ethyl hexyl methyl phosphate Chemical compound CCCCCCOP(=O)(OC)OCC KKLSTYKNFSNFAF-UHFFFAOYSA-N 0.000 description 1
- MSNSKDGQLPLKKR-UHFFFAOYSA-N ethyl hexyl octyl phosphate Chemical compound CCCCCCCCOP(=O)(OCC)OCCCCCC MSNSKDGQLPLKKR-UHFFFAOYSA-N 0.000 description 1
- SRBJEMYIWDBZAB-UHFFFAOYSA-N ethyl hexyl pentyl phosphate Chemical compound CCCCCCOP(=O)(OCC)OCCCCC SRBJEMYIWDBZAB-UHFFFAOYSA-N 0.000 description 1
- GARMNWPAUGAYEW-UHFFFAOYSA-N ethyl hexyl propyl phosphate Chemical compound CCCCCCOP(=O)(OCC)OCCC GARMNWPAUGAYEW-UHFFFAOYSA-N 0.000 description 1
- XMNQCSOOUOJOLR-UHFFFAOYSA-N ethyl methyl hydrogen phosphate Chemical compound CCOP(O)(=O)OC XMNQCSOOUOJOLR-UHFFFAOYSA-N 0.000 description 1
- WANIKAUEWKIFAJ-UHFFFAOYSA-N ethyl methyl octyl phosphate Chemical compound CCCCCCCCOP(=O)(OC)OCC WANIKAUEWKIFAJ-UHFFFAOYSA-N 0.000 description 1
- WLPVPLKXNMSLLC-UHFFFAOYSA-N ethyl methyl pentyl phosphate Chemical compound CCCCCOP(=O)(OC)OCC WLPVPLKXNMSLLC-UHFFFAOYSA-N 0.000 description 1
- QOSZFDSHQYCCHU-UHFFFAOYSA-N ethyl methyl propyl phosphate Chemical compound CCCOP(=O)(OC)OCC QOSZFDSHQYCCHU-UHFFFAOYSA-N 0.000 description 1
- DNYWKFUDIOXPNR-UHFFFAOYSA-N ethyl octyl pentyl phosphate Chemical compound CCCCCCCCOP(=O)(OCC)OCCCCC DNYWKFUDIOXPNR-UHFFFAOYSA-N 0.000 description 1
- ZOWIODUPWXZSMJ-UHFFFAOYSA-N ethyl octyl propyl phosphate Chemical compound CCCCCCCCOP(=O)(OCC)OCCC ZOWIODUPWXZSMJ-UHFFFAOYSA-N 0.000 description 1
- BTYBQJRZZRGWQQ-UHFFFAOYSA-N ethyl pentyl propyl phosphate Chemical compound CCCCCOP(=O)(OCC)OCCC BTYBQJRZZRGWQQ-UHFFFAOYSA-N 0.000 description 1
- NPABQWSZGGHWCK-UHFFFAOYSA-N ethyl-heptyl-hexylphosphane Chemical compound CCCCCCCP(CC)CCCCCC NPABQWSZGGHWCK-UHFFFAOYSA-N 0.000 description 1
- DJRSBZANDOPWJE-UHFFFAOYSA-N ethyl-heptyl-pentylphosphane Chemical compound CCCCCCCP(CC)CCCCC DJRSBZANDOPWJE-UHFFFAOYSA-N 0.000 description 1
- LIPNXZVCUOAVLA-UHFFFAOYSA-N ethyl-heptyl-propylphosphane Chemical compound CCCCCCCP(CC)CCC LIPNXZVCUOAVLA-UHFFFAOYSA-N 0.000 description 1
- TUFSWEOPGKYREV-UHFFFAOYSA-N ethyl-hexyl-octylphosphane Chemical compound CCCCCCCCP(CC)CCCCCC TUFSWEOPGKYREV-UHFFFAOYSA-N 0.000 description 1
- OEWQLTOHXFMHMS-UHFFFAOYSA-N ethyl-hexyl-pentylphosphane Chemical compound CCCCCCP(CC)CCCCC OEWQLTOHXFMHMS-UHFFFAOYSA-N 0.000 description 1
- HYKBXPOGFCPEIX-UHFFFAOYSA-N ethyl-hexyl-propylphosphane Chemical compound CCCCCCP(CC)CCC HYKBXPOGFCPEIX-UHFFFAOYSA-N 0.000 description 1
- QCFKMMLFAJBTBJ-UHFFFAOYSA-N ethyl-octyl-pentylphosphane Chemical compound CCCCCCCCP(CC)CCCCC QCFKMMLFAJBTBJ-UHFFFAOYSA-N 0.000 description 1
- FRAVTKWAXSXKCB-UHFFFAOYSA-N ethyl-octyl-propylphosphane Chemical compound CCCCCCCCP(CC)CCC FRAVTKWAXSXKCB-UHFFFAOYSA-N 0.000 description 1
- QCRLZVFXLXXPMR-UHFFFAOYSA-N ethyl-pentyl-propylphosphane Chemical compound CCCCCP(CC)CCC QCRLZVFXLXXPMR-UHFFFAOYSA-N 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- KVGLBTYUCJYMND-UHFFFAOYSA-N fonofos Chemical compound CCOP(=S)(CC)SC1=CC=CC=C1 KVGLBTYUCJYMND-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- AATKOEMGUUJXCT-UHFFFAOYSA-N hept-1-ene phosphane Chemical compound P.C=CCCCCC.C=CCCCCC.C=CCCCCC AATKOEMGUUJXCT-UHFFFAOYSA-N 0.000 description 1
- CNPKMYBCUOVDCE-UHFFFAOYSA-N heptan-2-yl dihydrogen phosphate Chemical compound CCCCCC(C)OP(O)(O)=O CNPKMYBCUOVDCE-UHFFFAOYSA-N 0.000 description 1
- ZSPWOAWAUATDGM-UHFFFAOYSA-N heptan-2-ylphosphonous acid Chemical compound CCCCCC(C)P(O)O ZSPWOAWAUATDGM-UHFFFAOYSA-N 0.000 description 1
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- UGXUPAKCTYOISO-UHFFFAOYSA-N heptyl hexyl hydrogen phosphate Chemical compound CCCCCCCOP(O)(=O)OCCCCCC UGXUPAKCTYOISO-UHFFFAOYSA-N 0.000 description 1
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- DVETVHHTHXURNN-UHFFFAOYSA-N heptyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCCCCC)C1=CC=CC=C1 DVETVHHTHXURNN-UHFFFAOYSA-N 0.000 description 1
- RZUGYOGHACALHY-UHFFFAOYSA-N heptyl(methyl)phosphane Chemical compound CCCCCCCPC RZUGYOGHACALHY-UHFFFAOYSA-N 0.000 description 1
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- FEKFIHUXXGOQDC-UHFFFAOYSA-N heptyl-hexyl-methylphosphane Chemical compound CCCCCCCP(C)CCCCCC FEKFIHUXXGOQDC-UHFFFAOYSA-N 0.000 description 1
- OENLDWNOWWYDDQ-UHFFFAOYSA-N heptylphosphinous acid Chemical compound CCCCCCCPO OENLDWNOWWYDDQ-UHFFFAOYSA-N 0.000 description 1
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- UMTSHFHBPGIYPE-UHFFFAOYSA-N hexan-2-ylphosphonous acid Chemical compound CCCCC(C)P(O)O UMTSHFHBPGIYPE-UHFFFAOYSA-N 0.000 description 1
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- SVYJJKRYBVVZBR-UHFFFAOYSA-N hexyl methyl octyl phosphate Chemical compound CCCCCCCCOP(=O)(OC)OCCCCCC SVYJJKRYBVVZBR-UHFFFAOYSA-N 0.000 description 1
- WDBFTYDLTVFFPA-UHFFFAOYSA-N hexyl methyl pentyl phosphate Chemical compound CCCCCCOP(=O)(OC)OCCCCC WDBFTYDLTVFFPA-UHFFFAOYSA-N 0.000 description 1
- JUKBDQALRFRFHL-UHFFFAOYSA-N hexyl methyl propyl phosphate Chemical compound CCCCCCOP(=O)(OC)OCCC JUKBDQALRFRFHL-UHFFFAOYSA-N 0.000 description 1
- XSKAFUDYILXFEV-UHFFFAOYSA-N hexyl(methyl)phosphane Chemical compound CCCCCCPC XSKAFUDYILXFEV-UHFFFAOYSA-N 0.000 description 1
- ONFLZIROXGGDSF-UHFFFAOYSA-N hexyl(propyl)phosphane Chemical compound CCCCCCPCCC ONFLZIROXGGDSF-UHFFFAOYSA-N 0.000 description 1
- JAXRBLAJXQMBAK-UHFFFAOYSA-N hexyl-methyl-octylphosphane Chemical compound CCCCCCCCP(C)CCCCCC JAXRBLAJXQMBAK-UHFFFAOYSA-N 0.000 description 1
- KDAWQDICRKDWJQ-UHFFFAOYSA-N hexylphosphinous acid Chemical compound CCCCCCPO KDAWQDICRKDWJQ-UHFFFAOYSA-N 0.000 description 1
- GJWAEWLHSDGBGG-UHFFFAOYSA-N hexylphosphonic acid Chemical group CCCCCCP(O)(O)=O GJWAEWLHSDGBGG-UHFFFAOYSA-N 0.000 description 1
- SNJWJGFQAADYBL-UHFFFAOYSA-N hexylphosphonous acid Chemical compound CCCCCCP(O)O SNJWJGFQAADYBL-UHFFFAOYSA-N 0.000 description 1
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- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
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- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
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- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
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- 238000012423 maintenance Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
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- OKNOYTLCXPCLMI-UHFFFAOYSA-N methyl dioctan-2-yl phosphate Chemical compound CCCCCCC(C)OP(=O)(OC)OC(C)CCCCCC OKNOYTLCXPCLMI-UHFFFAOYSA-N 0.000 description 1
- BVAGTSRQKIVPOF-UHFFFAOYSA-N methyl octyl pentyl phosphate Chemical compound CCCCCCCCOP(=O)(OC)OCCCCC BVAGTSRQKIVPOF-UHFFFAOYSA-N 0.000 description 1
- CCSWTRHQFZMJLH-UHFFFAOYSA-N methyl octyl propyl phosphate Chemical compound CCCCCCCCOP(=O)(OC)OCCC CCSWTRHQFZMJLH-UHFFFAOYSA-N 0.000 description 1
- ZVLPNLQTSUJPIY-UHFFFAOYSA-N methyl pentyl propyl phosphate Chemical compound CCCCCOP(=O)(OC)OCCC ZVLPNLQTSUJPIY-UHFFFAOYSA-N 0.000 description 1
- HAAKZVKFOAEVNQ-UHFFFAOYSA-N methyl(octan-3-yl)phosphane Chemical compound C(C)C(CCCCC)PC HAAKZVKFOAEVNQ-UHFFFAOYSA-N 0.000 description 1
- JJMKKUACKBSMSY-UHFFFAOYSA-N methyl(octyl)phosphane Chemical compound CCCCCCCCPC JJMKKUACKBSMSY-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
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- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
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- WOEPYWGRHWVHPG-UHFFFAOYSA-N nonan-3-yl dihydrogen phosphate Chemical compound C(C)C(CCCCCC)OP(O)(O)=O WOEPYWGRHWVHPG-UHFFFAOYSA-N 0.000 description 1
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- CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical group C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 description 1
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- 230000037361 pathway Effects 0.000 description 1
- NCVVTDLFKVYDRI-UHFFFAOYSA-N pentan-2-yl dihydrogen phosphate Chemical compound CCCC(C)OP(O)(O)=O NCVVTDLFKVYDRI-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- VUTSVIHQBJIUOS-UHFFFAOYSA-N phenyl dipropyl phosphate Chemical compound CCCOP(=O)(OCCC)OC1=CC=CC=C1 VUTSVIHQBJIUOS-UHFFFAOYSA-N 0.000 description 1
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- JJGAPRHMGMSOLF-UHFFFAOYSA-N phosphonooxysulfamic acid Chemical compound S(=O)(=O)(O)NOP(O)(O)=O JJGAPRHMGMSOLF-UHFFFAOYSA-N 0.000 description 1
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- GQRQDDIGHMRDMG-UHFFFAOYSA-N tri(heptan-3-yl)phosphane Chemical compound CCCCC(CC)P(C(CC)CCCC)C(CC)CCCC GQRQDDIGHMRDMG-UHFFFAOYSA-N 0.000 description 1
- UXYMZAXLUPHEKH-UHFFFAOYSA-N tri(heptan-4-yl)phosphane Chemical compound CCCC(CCC)P(C(CCC)CCC)C(CCC)CCC UXYMZAXLUPHEKH-UHFFFAOYSA-N 0.000 description 1
- PCXNOYNWXOIZNT-UHFFFAOYSA-N tri(octan-4-yl)phosphane Chemical compound CCCCC(CCC)P(C(CCC)CCCC)C(CCC)CCCC PCXNOYNWXOIZNT-UHFFFAOYSA-N 0.000 description 1
- OACSUWPJZKGHHK-UHFFFAOYSA-N tribenzyl phosphate Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)(=O)OCC1=CC=CC=C1 OACSUWPJZKGHHK-UHFFFAOYSA-N 0.000 description 1
- ZUOKGVSVSVEDQU-UHFFFAOYSA-N tributan-2-yl phosphate Chemical compound CCC(C)OP(=O)(OC(C)CC)OC(C)CC ZUOKGVSVSVEDQU-UHFFFAOYSA-N 0.000 description 1
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- JPAGOYOANAPHML-UHFFFAOYSA-N triheptan-4-yl phosphate Chemical compound CCCC(CCC)OP(=O)(OC(CCC)CCC)OC(CCC)CCC JPAGOYOANAPHML-UHFFFAOYSA-N 0.000 description 1
- GSURLQOINUQIIH-UHFFFAOYSA-N triheptyl phosphate Chemical compound CCCCCCCOP(=O)(OCCCCCCC)OCCCCCCC GSURLQOINUQIIH-UHFFFAOYSA-N 0.000 description 1
- SFENPMLASUEABX-UHFFFAOYSA-N trihexyl phosphate Chemical compound CCCCCCOP(=O)(OCCCCCC)OCCCCCC SFENPMLASUEABX-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- USKZTLWUJGOWOL-UHFFFAOYSA-N trinonan-2-yl phosphate Chemical compound CCCCCCCC(C)OP(=O)(OC(C)CCCCCCC)OC(C)CCCCCCC USKZTLWUJGOWOL-UHFFFAOYSA-N 0.000 description 1
- YIZBZLXFYAOFDQ-UHFFFAOYSA-N trinonan-4-yl phosphate Chemical compound CCCCCC(CCC)OP(=O)(OC(CCC)CCCCC)OC(CCC)CCCCC YIZBZLXFYAOFDQ-UHFFFAOYSA-N 0.000 description 1
- IPLYEZKKADASMG-UHFFFAOYSA-N trioctan-3-yl phosphate Chemical compound CCCCCC(CC)OP(=O)(OC(CC)CCCCC)OC(CC)CCCCC IPLYEZKKADASMG-UHFFFAOYSA-N 0.000 description 1
- JFDIYJKFEQXGLQ-UHFFFAOYSA-N trioctan-4-yl phosphate Chemical compound CCCCC(CCC)OP(=O)(OC(CCC)CCCC)OC(CCC)CCCC JFDIYJKFEQXGLQ-UHFFFAOYSA-N 0.000 description 1
- WVPGXJOLGGFBCR-UHFFFAOYSA-N trioctyl phosphate Chemical compound CCCCCCCCOP(=O)(OCCCCCCCC)OCCCCCCCC WVPGXJOLGGFBCR-UHFFFAOYSA-N 0.000 description 1
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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
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
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Abstract
一种复合膜及其制备方法,它含有多孔载体和聚酰胺表面。本发明膜具有改善的流通率和/或排斥率。本发明膜能在低操作压力下操作。本发明方法包括将多官能胺与多功能酰卤反应以形成聚酰胺。本方法包括在多官能酰卤与多官能胺完全反应之前将络合剂与多官能酰卤反应的步骤。本方法容易的适合商业规模制造方法,特别适于制造毫微过滤膜和反渗透复合膜。
Description
发明背景
反渗透膜和毫微过滤膜被用于从原料流中分离溶解或分散的物料。分离方法通常包括在压力下使进料的水溶液与膜的一个表面接触,以使水相透过膜而同时溶解或分散的物料无法渗透。
反渗透膜和毫微过滤膜通常都包括一层安装在多孔载体上的薄膜甑别层,它们共同构成所谓的“复合膜”。超滤薄膜和微量过滤薄膜也可能具有复合结构。载体提供机械力,但由于其多孔性,几乎无法提供阻流性。另一方面,甑别层比较少孔,是分离溶解或分散物料的主要方法。因此,通常是甑别层决定了一种给定膜的“排斥率”——排斥的特定溶解物(即溶质)的百分比,和“流通率”——溶剂通过膜时每单位面积的流量。
反渗透膜和毫微过滤薄膜由于对不同离子和有机化合物的渗透度不同而各不相同。相对而言,几乎所有离子都不能透过反渗透膜,包括钠和氯离子。因此,由于反渗透膜对钠和氯离子的排斥率通常为约95%至约100%,它被广泛地用于微咸水或海水的脱盐,从而提供工业、商业或家庭使用的不含盐的水。
毫微过滤膜通常对离子的排斥更加特异。通常,毫微过滤膜能阻隔二价离子,包括镭、镁、钙、硫酸根和碳酸根。而且,毫微过滤膜通常对分子量在200道尔顿以上的有机化合物具有不可渗透性。另外,与反渗透膜相比,毫微过滤膜在同等压力下通常具有更高的流量。这些特性使毫微过滤膜适用于水的“软化”和清除水中的农药等不同的领域。例如,毫微过滤膜的氯化钠排斥率通常在约0%至约95%,但对硫酸镁等盐以及有时对阿特拉津(一种除草剂)等有机化合物却具有相对较高的排斥率。
在反渗透和毫微过滤应用中尤其有用的膜是甑别层为一种聚酰胺的膜。反渗透膜的聚酰胺甑别层通常是通过一种在多官能胺单体和一种多官能酰卤单体(也被称为多官能酰基卤)之间的界面缩聚反应制得,可见美国专利4277344的描述,此处将其作为参考。毫微渗透膜的聚酰胺甑别层通常是通过一种哌嗪或哌嗪取代胺或环己烷与一种多官能酰卤之间的界面聚合反应制得,可见美国专利4769148和4859384的描述,将它们的整体并入作为参考。制成适用于毫微过滤的聚酰胺甑别层的另一方法是通过如美国专利4765897;4812270;和4824574所述的方法。这些专利描述了将如美国专利4277344中的反渗透膜转化成毫微过滤膜的方法。
复合聚酰胺膜通常通过用多官能胺单体在多孔载体上涂层的方法制备,最常用的是用水溶液涂层。水是优选的溶剂,但也可使用非水性溶剂,如乙酰基腈和二甲基甲酰胺(DMF)。随后在载体上涂上一层多官能酰卤单体(也被称为酰基卤),通常来自有机溶液。尽管并不必需特定的添加顺序,但通常是在多孔载体上先涂层胺溶液,再涂层酰卤溶液。多官能胺或/和酰卤可以通过溶液施用到多孔载体上,它们也可以选择通过其他方式应用,如通过气相淀积,或不与其他物质混合。
通过在胺和/或酰卤溶液中添加成分来提高膜的性能的方法在文献中已有描述。例如,授予Chau的美国专利4950404描述了一种通过在胺和聚羧酸卤化物进行界面聚合之前在胺的水溶液中加入一种极性非质子溶剂和可选择的酸性接受体,以增强复合膜流量的方法。与此相似的,Hirose等人的美国专利6024873;5989426;5843351;5733602;5614099;和5576057描述了在界面聚合反应之前在胺的水溶液和/或有机酸卤化物溶液中加入经过挑选的醇、醚、酮、酯、卤代烃类,含氮的化合物和溶解参数为8至14(cal/cm3)1/2含硫的化合物。
通过后处理提高膜性能的方法也是已知的。例如,Jons等人的美国专利5876602就描述了用一种水溶性氯化剂处理聚酰胺复合膜以提高流量,减少盐的通过,和/或提高膜在基座上的稳定性。Mickols的美国专利5755964揭示了一种用氨或经过挑选的胺,如丁胺、环己胺、和1-6-己二胺处理聚酰胺甑别层的方法。Cadotte的美国专利4765897揭示了用强无机酸对膜进行后处理,随后再用一种清除加强剂处理。美国专利4765897、5876602、5755964在此作为参考。
需要制成在常规操作压力下具有较高流通率的膜,或是能够在相对较低的操作压力下保持流通率的膜。此外,提高了流通率和/或降低了压力要求的同时,仍具有较高排斥率的膜也是希望得到的。制造这样的膜的方法,尤其是那些容易适应大规模的膜制造的方法,也是需要的。
发明概要
本发明提供了一种改进的复合膜及其制造方法,该方法是通过多官能胺与多官能酰卤在多孔载体的至少一个表面进行界面聚合以在该表面形成聚酰胺层。该方法以在多官能酰卤与多官能胺反应之前和/或反应过程中用多官能酰卤接触络合剂的步骤为特征。
本发明的目的之一是提供具有更高流通率和/或更优排斥性(即高或低取决于膜的最终用途)的改进膜。本发明进一步的目的是提供能够在相对较低压力下运作并且还能具有特定流通率和/或排斥率的膜。本发明另一个目的是提供制造这些膜的方法,包括容易适应商用规模的膜制造的方法。此方法尤其适于制造毫微过滤和反渗透膜。发明的具体描述
本发明的复合膜是通过在多孔载体的至少一个表面上界面聚合多官能胺单体(此处也称为“胺”,“聚胺”,和“多官能胺”一其中每个术语都可指使用一类胺或合并使用多类胺)与多官能酰卤(也称为“酰卤”、“酰基卤”、多官能酰基卤一其中每个术语都可指使用一类酰卤或合并使用多类酰卤)。胺和酰卤通常通过溶液涂层步骤置于多孔载体上,其中胺主要是通过水溶液涂层,酰卤主要是通过无水、有机溶液涂层。尽管涂层过程可以是非有序性的,也就是说没有特定的顺序,但优选的是先在载体上涂上胺,再涂酰卤。涂层可以通过喷涂、滚涂、使用浸渍槽完成。从载体上除去过量的溶液可以利用空气和/或刮水刀、干燥器、烘箱等。
本发明中使用的多官能胺单体可以含有伯氨或仲氨基团,可以是芳族(如,间苯二胺、对苯二胺、1,3,5-三氨基苯、1,3,4-三氨基苯,3,5-二氨基苯甲酸、2,4-二氨基甲苯、2,4-二氨基苯甲醚,和亚二甲基苯二胺)或脂肪族(如乙烯二胺、丙邻二胺和三(2-二氨基乙基)胺。优选的胺类包括具有两个或三个氨基团的芳香族伯胺,尤其是间苯二胺,和含有两个氨基团的脂肪族仲胺,尤其是哌嗪。胺通常是作为水溶液应用到多微孔载体上。水溶液通常含有大约0.1至20wt%的胺,优选为大约0.5至6wt%。一旦涂上多微孔载体,过量的胺的水溶液可以随意除去。胺溶液并不必须是水性的,但优选与下述非极性非水溶剂不溶混的。
正如前文所述,单体多官能酰卤优选通过非极性溶剂涂层,尽管多官能酰卤可以通过汽相(对于具有足够蒸汽压力的多官能酰卤而言)涂层。多官能酰卤优选为天然的芳香族,并且每分子含有至少两个优选为三个酰卤基团。由于它们的低成本和高实用性,氯化物与相应的溴化物或碘化物相比,通常是首选的。一种优选的多功能酰卤是三内消旋酰氯化物(trimesoyl chloride,TMD)。多官能酰卤通常溶解于非极性有机溶剂中,占0.01至10.0wt%(优选为0.05至3wt%),并作为连续涂层操作的一部分进行。合适的非极性溶剂是那些能够溶解多官能酰卤和与水不溶混的溶剂。优选的溶剂包括那些不会对臭氧层造成威胁以及其闪燃性和易燃性足够安全,无须采取特别的预防措施也能进行常规操作的溶剂。高熔点的烃,也就是熔点高于90℃的烃,如C8-C14的烃和它们的混合物,比其C5-C7的对应物具有更适宜的闪燃点,但它们比较不容易挥发。
多官能酰卤与多官能胺一旦互相接触,就是它们表面接触面进行反应形成聚酰胺甑别层。反应时间通常少于一秒,但接触时间通常在一至60秒之间,此后,过量的液体可通过多种方式随意除去,如气刀、水浴,干燥器和相似物。尽管可以使用室温下的空气干燥,但通过在升高的温度中干燥来实现过量水和/或有机溶剂的清除是最为方便的,如从大约40℃至约120℃。
不希望受到理论的束缚,我们相信多官能酰卤单体的酰卤官能基团通常在与胺官能基团接触前就已经水解。在正常制造条件下,酰卤官能基团的这种水解是绝对不可逆的。也就是说,在大规模膜制造通常使用的时间、温度和浓度下,胺官能基团不会与水解的酰卤基团充分反应。酰卤基团的这种水解被认为会导致膜性能受损。
不希望受到理论的束缚,我们相信相关络合剂在按照本方法使用时,能够与多官能酰卤单体形成“缔合”。这种缔合的形成被认为会显著减少酰卤官能基团的水解,从而使此后酰卤和胺多官能基团之间的反应能够充分进行,并因此促成膜性能的上述改进。
术语“缔合”是为了描述在胺和酰卤多官能基团反应之前或反应过程中,相关络合剂与多官能酰卤之间产生的化学作用。这类缔合也能被描述成是多官能酰卤和溶液其他组分之间推斥力的消除。
另一种描述酰卤和络合剂之间交互作用的方式是它们的化合造成“总能量的改变”。按照外行人的说法,这是络合剂与酰卤之间产生的缔合造成的能量改变。更正式的说法中,总能量“U”可由等式I表示:
可见H.Callan’s“Thermodynamics”,(John Wily & Son,New York,1960)。截然不同的化学物类的化合造成的总量变化“ΔU”(变化“Δ”),可由公式II表示:
其中u是每种化学物类(如TMC和络合剂)的化学势,N是每种化学物类的摩尔数,T是温度,S是熵,P是压力,V是系统体积,i和m是从1开始的整数,其中m代表系统中化学物类的总数。总能量与有实验限制的能量的其他几种表示法有密切关系。例如,自由能“μ”通常用于在大气压力下进行的反应,可以由公式III表示:
μ=nG-TS-PV
其中n等于缔合的物类的摩尔数(如酰卤单体和络合剂的反应产物),G是吉布斯自由能,T是温度,S是熵,P是压力,V是系统体积。G可以由公式IV表示:
ΔG=ΔH-TS
其中H是系统的熵。所有能量的参比和相关术语和符号都与标准的化学规范相一致。
与酰卤结合时,本发明中的络合剂造成总量的变化优选为约3.5至20kcals/mole,更优选为5至15kcals/mole,再优选为5至10kcals/mole。在本发明中,酰卤与络合剂的化合造成的总量的变化接近于吉布斯自由能和热函的变化,如U≈G≈H。因此,熟知本领域的人通常可以通过测量络合剂和酰卤化合的热函来确定特定的络合剂与特定酰卤种类使用时的适合度。测量系统热函的量热方法是公知的。
在许多实例中,特定络合剂和酰卤交互作用的总能量和/或热函,约等于生产条件下使用的系统总能量和热函。也就是说,酰卤和络合剂之间交互作用的总能量或热函的变化可通过测量加入络合剂的系统的热函的变化,如含有酰卤、溶剂、添加剂、杂质等的酰卤涂层溶液,来近似地达到。对于络合剂与胺溶液中的酰卤接触的实施例来说,可适用的“系统”可以被附加的化学物类复杂化,如胺,水,等。在最后的分析中,最具实质性的正是酰卤和络合剂交互作用造成的总能量的变化。因此,我们应该意识到反应媒介对系统总能量的变化具有重大的影响。例如,在优选的实施例,酰卤和络合剂在它们涂层的溶液中都是完全可溶解的。
太弱的缔合(也就是总能量值低于3.5kcal/mole)致使缔合无法有效地阻止酰卤官能基团的水解。正如下文将要描述的那样,缔合足够强的一种测定方法就是在聚酰胺中存在“可检测的量”的“残留”络合剂,即使是在膜的后清洗之后。另一方面,太强的缔合(也就是总能量高于20或优选15kcal/mole)在膜形成过程中,不能带来胺足够的置换和反应,从而阻碍了所需聚酰胺的形成。太强缔合的一个实例是正常生产条件下TMC的氯化酰基基团水解,这造成总能量值高于25kcals/mole。
要实现本发明的最大价值,在酰卤和胺之间的反应之前或反应过程中,在络合剂和酰卤间形成所述的缔合是很重要的。因此,络合剂加入的时间和方式被认为是重要的。例如,在酰卤和胺已经充分反应之后再单独加入磷酸(如,美国专利4765897所述)就无法体现本发明的益处。而且,如果络合剂以无法在其间形成缔合的方式与酰卤相接触,本发明的价值也无法体现。例如,如果一种络合剂在酰卤溶液中不是完全可溶或可分散的,那么由于发生程度不够的缔合,本发明完整的价值就不可能得到实现。因此,本发明优选的实施方案采用在酰卤溶液中完全可溶而且容易与酰卤形成缔合的络合剂。正如别处所述,优选的络合剂溶解参数为约15至大约26,优选为18至23J1/2cm-3/2。
在优选的实施方案中,在酰卤与胺溶液接触之前,将本发明络合剂直接加入酰卤溶液中,以在胺和酰卤反应之前获得充分的形成缔合的机会。作为选择,还可以将酰卤和络合剂“不掺水”地接触,并随后加入涂层溶液中。
在次优选的实施例中,络合剂可以与酰卤溶液相接触(如,通过喷射),与此同时酰卤溶液与多官能胺溶液相接触。在此实施例中,络合剂必须在酰卤和胺溶液接触的步骤的同时与酰卤溶液相接触,但要先于酰卤和胺的完全反应。在该实施方案中,在酰卤和胺完全反映之前酰卤和络合剂经历较短的时间形成复合物。作为选择,还可以在酰卤与胺溶液接触之后完全反应之前,将络合剂与酰卤溶液相接触。如前所述,本实施例使酰卤与胺完全反应之前形成络合物所需的时间短的多。
在更次优选的实施例中,络合剂可以在与胺和酰卤溶液接触前,涂在载体上或是加入胺溶液中。这些方法是次优选的,释放因为很难以一种在酰卤与胺反应完成之前容许适当络合形成的方式来向酰卤中转移络合剂。然而,一种补救途径包括胺溶液中络合剂的高内相乳剂的形成,由此带来酰卤与胺反应过程中络合剂向酰卤中相对均衡的释放。高内相乳剂的形成是公知的,且在美国专利5977194中有所描述,此处作为参考列入。其他合适的方法包括选择在胺溶液中具有充分溶解度的络合剂,以均匀分散,同时还要在酰卤溶液(如有机溶液)中能充分溶解,从而能够在酰卤与胺完全反应之前为酰卤提供足量的络合剂。
上述实施例可以合并使用,如本发明络合剂可以在与溶液接触前同时加入酰卤和胺溶液中。可选择的是,络合剂可以加入任一溶液中,可在涂溶液的过程中通过喷射或气相淀积施用。
一种判定本发明络合剂是否通过本发明方法成功地与酰卤接触的方法是在聚酰胺膜中存在“可检测量”的“残留”络合剂。用语“残留”是指即使膜已经在反渗透模具中经过以下操作仍残存(如缔合、共价键合、络合、微弱结合等)在聚酰胺膜中的络合剂:25℃,用24gfd(加仑每平方英尺每天)(0.0011cm/sec/)流动率的纯净水流在0.5%至25%之间的渗透回收率下通过膜,持续24小时。这可以利用通常测试膜时所用的试验槽来完成。例如,试验槽可以是“平板和框架”式或者为膜准备螺旋缠绕元件。
用纯净水清洗,比如在大约70磅每平方英寸的压力、25℃下将纯净水通过聚酰胺膜达24小时。此种清洗清除了最初就存在但对本发明没有价值的物料的瞬时源。例如,众所周知磷酸可以作为一种pH缓冲剂加入到胺溶液中。在此类实施方案中,一部分磷酸可能在膜最初生成中就存在;然而,由于磷酸并不与酰卤以实现充分缔合的方式相作用,磷酸不会被保留并且在使用或清洗时就从膜中冲去。尽管磷酸的这些现有技术用途可以与本发明联合使用,此类现有技术实施方案并不产生“残留”的亚磷,也不影响本发明带来的膜性能的改善程度。
用语“可检测量”是指存在的残留络合剂的足够量,以使其可被测量、鉴别或通过定量分析或定性分析以别的方式检测。这些膜中的络合剂的检测可以通过任何适当的分析技术进行;然而,由于通常使用的是相对少量的络合剂,因此优选相对敏感的分析技术,如气相色谱法、X射线荧光,(XRF),次极离子质谱法,IR,和充分燃烧的聚酰胺的比色分析。通常络合剂的检测重点在络合剂的结合核。正如以下更具体的描述,结合核通常包括金属,如Pb,Fe,Cr,Ni,Co,Cu,Zn,Al,As,Sb,Te等,但也可以包括其他成分,如P,Si,Se,Ge等。一种特定的X射线荧光检测工艺尤其适合检测含亚磷的络合剂,它包括从多孔载体中提取一部分聚酰胺聚合物(如100mg),如将膜放在水中沸腾30分钟,然后用合适溶剂溶解多孔载体,如二氯甲烷,随后在同样的溶剂中粗提取聚酰胺。然后聚酰胺被离析并且用模头和液压机(10000Ibs.load)压成直径13mm的圆板。将得到的圆板放在聚丙烯样品载体膜(6.0微米厚)的两层之间,并且用标准支承环系在一个Chemplex直径30mm的XRF样品杯上。该样品可以用铅遮蔽层在塑料插入物中测量。可以在圆板两面都进行测量,再取平均值。该样品一准备好,就可以用装有钪阳极3KW X射线电子管的Philips PW1480波长分散X射线荧光分光计进行分析。例如,亚磷可以用K alpha X射线强度通过在下列条件下的操作来进行测量:50kY,50mA,甑别级别80/25上下,氦净化。亚磷的K alpha峰值可以在141.035的2 theta角测量,本底可以+和-1.5偏差来测量,峰值和本底的测量通常每次花10秒。
在优选的实施例中,聚酰胺复合膜在每克聚酰胺中包括至少大约25微克(优选为至少50微克,更优选为100微克,在某些实施例中至少200微克)的“残留”络合剂结合核。组成本发明络合剂结合核的成分通常在常规的膜制备过程中是不存在的。因此,这些成分可作为判断本发明络合剂在膜制备过程中是否已经有效使用的指示剂。
正如已经指出的,残留络合剂被认为是在络合剂和聚酰胺、残存单体、和/或反应产物间形成络合的结果。尽管由聚酰胺层的相对密度决定,但本发明中大多数膜在每平方米膜中都会包括至少0.02微克的络合剂,更常见的是每平方米膜中超过大约1微克络合剂。
本发明中的络合剂并没有特殊限制,而且不同种类的化合物也可结合使用。然而,优选的物类是非自燃的、在空气和水中足够稳定的(也就是在本方法期间内,不会分解、降解或与水或空气发生显著反应的物类),并且具有适当的工业卫生特性,如不会造成严重的环境危害、不需要庞大的操作条件、不会引起对安全的巨大关注等等。相关络合剂优选为在此描述的有机溶液中能够“充分可溶”的。用语“充分可溶”是指有足量的络合剂溶解在溶液中从而形成与不使用本发明络合剂制备的同一膜相比具有提高的流动性、排斥率和/或减低操作压力的最终膜。络合剂“充分可溶”的另一标志是在聚酰胺层中存在可检测量的残留络合剂。当在有效浓度使用时,该络合剂更适宜在前述有机溶剂中溶解并形成单个均相。优选的络合剂为溶解参数在大约15至26的,更优选为18至23J1/2cm-3/2。
不考虑络合剂与酰卤溶液接触的方式,络合剂的量与多官能酰卤量的关系优选为按化学量计算。优选的络合剂与多官能酰卤的化学量比是大约1∶5至约5∶1,最优选为1∶1至大约3∶1。尽管是优选的,络合剂的化学量比并不是必须的。直接与酰卤溶液结合时,络合剂通常占酰卤溶液的约0.001至约2wt%。按照前述作为选择的实施方案实施时,可能需要量更多的络合剂。
不像传统的多官能酰卤与多官能胺的界面聚合中酰卤类的相对浓度是速率控制的,本发明中胺类的相对浓度可能起到更重要的作用。通过常规的实验法,络合剂、酰卤和胺的特性和浓度、反应条件和想要的膜特性特定的条件下,熟知本领域的人可以得出多官能胺的最佳浓度。
本发明的络合剂包括种类繁多的化合物,通常可由结构式I表示:
α(Lxβ)y
其中α是从以下成分中挑选出的不含硫的结合核:(a)传统IUPAC周期表中的族IIIA-VIB(即族IIIA、IVA、VA、VIA、VIIA、VIIIA、IB、IIB、IIIB、IVB、VB、VIB)和b)元素周期3-6(即从Na、K、Rb和Cs开始的元素周期)。传统IUPAC元素周期表的族IIIA-VIB对应于:“新符号”IUPAC周期表的族3-16和元素周期表CAS版的族IIIB-VIA。为避免混淆,这里进一步的说明将采用传统的IUPAC元素周期表,即族IIIA对应于Sc、Y、La等为首的列,而族VIB对应于O、S、Se、Te、Po为首的列。特定例子包括:(1)以下金属:铝、钪、钛、钒、铬、镁、铁、钴、镍、铜、锌、镓、锗、呻、钇、锆、铌、钼、锝、钌、铑、钯、银、镉、铟、锡、锑、碲、镧、铈、镨、钕、钷、钐、铕、钆、铽、镝、钬、铒、铥、镱、镥、铪、钽、钨、铼、锇、铱、铂、金、汞、铊、铅、铋(铋通常不是优选)和钋;(2)以下半导体:硅、硒、锗;和(3)亚磷。尤其优选的结合核包括:Al、Si、P、As、Sb、Se和Te和如下金属:Fe、Cr、Co、Ni、Cu和Zn。L是任选的化学键合基团,相同或不同的,从如下键中选择:含碳部分,如芳基、烷烃、烯烃、-O-,-S-,-N-,-H-,-P-,-O-P,和-O-P-O-,(每种都可以是取代的或未取代的)。β是加溶基团,相同或不同的,包括1-12个取代或未取代的,可能包含L所述的内部键合基团的碳原子。实施例包括有1至6个碳原子的脂肪基和芳烃基、芳基、杂环基和烷基。“x”是0至1的整数,“y”是1至5的整数,优选为2至4。
尽管由使用的特定溶剂和酰卤种类决定,以下络合剂在本发明中通常有效:磷、铋、砷和锑的三苯基衍生物(如磷化氢、磷酸盐);包括亚磷酸三丁酯和亚磷酸二丁酯的亚磷的链烷含氧酯;有机金属化合物,如二茂铁和四乙铅,和铁(II)、铁(III)、钴(III)和铬(III)的乙酰丙酮化物。
现已发现,含有磷结合核的络合剂是尤其优选的。优选的此类含磷的化合物可由以下结构式1表示:
结构式1
其中Z是相同或不同的,选自X,O-P-(X)2,P(O)-X2,(P(-X))m-P-X2,(O-P(-X))m-O-P-X2,(P(O)(-X))m-P(O)-X2和(O-P(O)(-X))m-O-P(O)-X2,其中P是亚磷,O是氧,m是1至5的整数;Y是O(氧)或一对非键合电子,分别如结构式2和3所示,
结构式2 结构式3
其中X是相同或不同的,选自:R或含氧和/或烷基键的R,如R-O-R,O-R,等;R是相同或不同的,选自H(氢),和/或含碳单体。优选选择Z基团从而使它们能共同形成可充分溶于有机溶液的含亚磷化合物。
用语“相同或不同的”是指由单个符号,如“R”表示的单个基团在给定的化合物中可以各不相同。如,对任何给定化合物,一个R基团可以是氢,而其它R基团可以是丁基族。
用语“含碳单体”是指支链或非支链无环基,如甲基、乙基、丙基、异丙基、丁基、戊基、2-戊基、3-戊基,叔丁基等,它们可以是非取代的或取代的(如用酰胺基、醚基、酯基、砜基,碳酰基、酐、氰化物、腈、异氰酸酯、氨基甲酸乙酯、β-羟基酯、双键和三键等),和环状基,如环戊基、环己基、芳族化合物等,苯基、杂环(如pryridine)等,它们可以是取代或非取代的(如用甲基、乙基、丙基、羟基、酰胺、醚、砜、碳酰基、酯等)。环状部分可以通过一个脂肪族连接基,如甲基、乙基等,与亚磷原子相连。
优选的含碳单体包括非取代的、支链或非支链C1-C12基团,更优选的是C1-C8脂肪族基团如:甲基、乙基、丙基、异丙基、丁基、2-甲基丁基、3-甲基丁基、2-乙基丁基、戊基、己基等。另外,优选单体包括戊基基团。
结构式7 结构式8 结构式9
其中R、P和O如前所述。此类含亚磷化合物可通过商业途径获得或者是可以使用已知方法合成,可见Whtstone的美国专利2648696的实施例,此处列入作为参考,和Ahroni等人,Journal of Polymer Science,卷22,2579-2599。
这里使用的亚磷命名法与在Inorganic Chemistry,6:Phosphorous-AnOutline of its Chemistry,Biochemistry and Technology,third ed.,(Elsevier1985)里D.Corbridge的论文中使用的方法一致:可使用的含亚磷的化合物包括:磷酸盐(如磷酸酯),亚磷酸酯、膦、氧膦、膦酸酯,包括二膦酸酯、次磷酸盐、phosphinites、亚膦酸盐、焦磷酸酯、焦磷酸胺,磷酰胺,包括二硫代磷酸酯的硫代磷酸酯、二硫代磷酸酯、酰氨基硫代磷酸酯和包括磷酰基二硫代硫酸盐的酰基硫代磷酸酯。每类的详细实例的非综合性列表如下。
三磷酸酯的详细实例包括:
三甲基磷酸酯、三乙基磷酸酯、三-(1-丙基)磷酸酯、三-(2-丙基)磷酸酯、三-(1-丁基)磷酸酯、三-(2-丁基)磷酸酯、三-(1-叔丁基)磷酸酯、三-(2-叔丁基)磷酸酯、三-(1-戊基)磷酸酯、三-(2-戊基)磷酸酯、三-(3-戊基)磷酸酯、三-(1-己基)磷酸酯、三-(2-己基)磷酸酯、三-(3-己基)磷酸酯、三-(1-庚基)磷酸酯、三-(2-庚基)磷酸酯、三-(3-庚基)磷酸酯、三-(4-庚基)磷酸酯、三-(1-辛基)磷酸酯、三-(2-辛基)磷酸酯、三-(3-辛基)磷酸酯、三-(4-辛基)磷酸酯、三-(1-CH3(CH2)8)磷酸酯、三-(2-CH3(CH2)8)磷酸酯、三-(3-CH3(CH2)8)磷酸酯、三-(4-CH3(CH2)8)磷酸酯、三-(1-CH3(CH2)9)磷酸酯、三-(2-CH3(CH2)9)磷酸酯、三-(3-CH3(CH2)9)磷酸酯、三-(4-CH3(CH2)9)磷酸酯、三-(5-CH3(CH2)9)磷酸酯、、三-(1-CH3(CH2)10)磷酸酯、三-(2-CH3(CH2)10)磷酸酯、三-(3-CH3(CH2)10)磷酸酯、三-(4-CH3(CH2)10)磷酸酯、三-(5-CH3(CH2)10)磷酸酯、、三-(1-CH3(CH2)11)磷酸酯、三-(2-CH3(CH2)11)磷酸酯、三-(3-CH3(CH2)11)磷酸酯、三-(4-CH3(CH2)11)磷酸酯、三-(5-CH3(CH2)11)磷酸酯、三-(6-CH3(CH2)11)磷酸酯、三-(1-CH3(CH2)12)磷酸酯、三-(2-CH3(CH2)12)磷酸酯、三-(3-CH3(CH2)12)磷酸酯、三-(4-CH3(CH2)12)磷酸酯、三-(5-CH3(CH2)12)磷酸酯、三-(6-CH3(CH2)12)磷酸酯、三-(甲基戊基)磷酸酯、三-(乙基戊基)磷酸酯、三-(甲基己基)磷酸酯、三-(乙基己基)磷酸酯、三-(丙基己基)磷酸酯、三-(甲基庚基)磷酸酯、三-(乙基庚基)磷酸酯、三-(二乙基庚基)磷酸酯、三-(甲基辛基)磷酸酯、三-(乙基辛基)磷酸酯、三-(二甲基辛基)磷酸酯、甲基二(-乙基)磷酸酯、甲基二-(1-丙基)磷酸酯、甲基二-(2-丙基)磷酸酯、甲基二-(1-丁基)磷酸酯、甲基二-(2-丁基)磷酸酯、甲基二-(1-叔丁基)磷酸酯、甲基二-(2-叔丁基)磷酸酯、甲基二-(1-戊基)磷酸酯、甲基二-(2-戊基)磷酸酯、甲基二-(3-戊基)磷酸酯、甲基二-(1-己基)磷酸酯、甲基二-(2-己基)磷酸酯、甲基二-(3-己基)磷酸酯、甲基二-(1-庚基)磷酸酯、甲基二-(2-庚基)磷酸酯、甲基二-(3-庚基)磷酸酯、甲基二-(4-庚基)磷酸酯、甲基二-(1-辛基)磷酸酯、甲基二-(2-辛基)磷酸酯、甲基二-(3-辛基)磷酸酯、甲基二-(4-辛基)磷酸酯、甲基二-(1-CH3(CH2)8)磷酸酯、甲基二-(2-CH3(CH2)8)磷酸酯、甲基二-(3-CH3(CH2)8)磷酸酯、甲基二-(4-CH3(CH2)8)磷酸酯、甲基二-(1-CH3(CH2)9)磷酸酯、甲基二-(2-CH3(CH2)9)磷酸酯、甲基二-(3-CH3(CH2)9)磷酸酯、甲基二-(4-CH3(CH2)9)磷酸酯、甲基二-(5-CH3(CH2)9)磷酸酯、、甲基二-(1-CH3(CH2)10)磷酸酯、甲基二-(2-CH3(CH2)10)磷酸酯、甲基二-(3-CH3(CH2)10)磷酸酯、甲基二-(4-CH3(CH2)10)磷酸酯、甲基二-(5-CH3(CH2)10)磷酸酯、、甲基二-(1-CH3(CH2)11)磷酸酯、甲基二-(2-CH3(CH2)11)磷酸酯、甲基二-(3-CH3(CH2)11)磷酸酯、甲基二-(4-CH3(CH2)11)磷酸酯、甲基二-(5-CH3(CH2)11)磷酸酯、甲基二-(6-CH3(CH2)11)磷酸酯、甲基二-(1-CH3(CH2)12)磷酸酯、甲基二-(2-CH3(CH2)12)磷酸酯、甲基二-(3-CH3(CH2)12)磷酸酯、甲基二-(4-CH3(CH2)12)磷酸酯、甲基二-(5-CH3(CH2)12)磷酸酯、甲基二-(6-CH3(CH2)12)磷酸酯、乙基二-(1-丙基)磷酸酯、乙基二-(2-丙基)磷酸酯、乙基二-(1-丁基)磷酸酯、乙基二-(2-丁基)磷酸酯、乙基二-(1-叔丁基)磷酸酯、乙基二-(2-叔丁基)磷酸酯、乙基二-(1-戊基)磷酸酯、乙基二-(2-戊基)磷酸酯、乙基二-(3-戊基)磷酸酯、乙基二-(1-己基)磷酸酯、乙基二-(2-己基)磷酸酯、乙基二-(3-己基)磷酸酯、乙基二-(1-庚基)磷酸酯、乙基二-(2-庚基)磷酸酯、乙基二-(3-庚基)磷酸酯、乙基二-(4-庚基)磷酸酯、乙基二-(1-辛基)磷酸酯、乙基二-(2-辛基)磷酸酯、乙基二-(3-辛基)磷酸酯、乙基二-(4-辛基)磷酸酯、乙基二-(1-CH3(CH2)8)磷酸酯、乙基二-(2-CH3(CH2)8)磷酸酯、乙基二-(3-CH3(CH2)8)磷酸酯、乙基二-(4-CH3(CH2)8)磷酸酯、乙基二-(1-CH3(CH2)9)磷酸酯、乙基二-(2-CH3(CH2)9)磷酸酯、乙基二-(3-CH3(CH2)9)磷酸酯、乙基二-(4-CH3(CH2)9)磷酸酯、乙基二-(5-CH3(CH2)9)磷酸酯、、乙基二-(1-CH3(CH2)10)磷酸酯、乙基二-(2-CH3(CH2)10)磷酸酯、乙基二-(3-CH3(CH2)10)磷酸酯、乙基二-(4-CH3(CH2)10)磷酸酯、乙基二-(5-CH3(CH2)10)磷酸酯、、乙基二-(1-CH3(CH2)11)磷酸酯、乙基二-(2-CH3(CH2)11)磷酸酯、乙基二-(3-CH3(CH2)11)磷酸酯、乙基二-(4-CH3(CH2)11)磷酸酯、乙基二-(5-CH3(CH2)11)磷酸酯、乙基二-(6-CH3(CH2)11)磷酸酯、乙基二-(1-CH3(CH2)12)磷酸酯、乙基二-(2-CH3(CH2)12)磷酸酯、乙基二-(3-CH3(CH2)12)磷酸酯、乙基二-(4-CH3(CH2)12)磷酸酯、乙基二-(5-CH3(CH2)12)磷酸酯、乙基二-(6-CH3(CH2)12)磷酸酯、1-丙基二-(2-丙基)磷酸酯、1-丙基二-(1-丁基)磷酸酯、1-丙基二-(2-丁基)磷酸酯、1-丙基二-(1-叔丁基)磷酸酯、1-丙基二-(2-叔丁基)磷酸酯、1-丙基二-(1-戊基)磷酸酯、1-丙基二-(2-戊基)磷酸酯、1-丙基二-(3-戊基)磷酸酯、1-丙基二-(1-己基)磷酸酯、1-丙基二-(2-己基)磷酸酯、1-丙基二-(3-己基)磷酸酯、1-丙基二-(1-庚基)磷酸酯、1-丙基二-(2-庚基)磷酸酯、1-丙基二-(3-庚基)磷酸酯、1-丙基二-(4-庚基)磷酸酯、1-丙基二-(1-辛基)磷酸酯、1-丙基二-(2-辛基)磷酸酯、1-丙基二-(3-辛基)磷酸酯、1-丙基二-(4-辛基)磷酸酯、1-丙基二-(1-CH3(CH2)8)磷酸酯、1-丙基二-(2-CH3(CH2)8)磷酸酯、1-丙基二-(3-CH3(CH2)8)磷酸酯、1-丙基二-(4-CH3(CH2)8)磷酸酯、1-丙基二-(1-CH3(CH2)9)磷酸酯、1-丙基二-(2-CH3(CH2)9)磷酸酯、1-丙基二-(3-CH3(CH2)9)磷酸酯、1-丙基二-(4-CH3(CH2)9)磷酸酯、1-丙基二-(5-CH3(CH2)9)磷酸酯、、1-丙基二-(1-CH3(CH2)10)磷酸酯、1-丙基二-(2-CH3(CH2)10)磷酸酯、1-丙基二-(3-CH3(CH2)10)磷酸酯、1-丙基二-(4-CH3(CH2)10)磷酸酯、1-丙基二-(5-CH3(CH2)10)磷酸酯、、1-丙基二-(1-CH3(CH2)11)磷酸酯、1-丙基二-(2-CH3(CH2)11)磷酸酯、1-丙基二-(3-CH3(CH2)11)磷酸酯、1-丙基二-(4-CH3(CH2)11)磷酸酯、1-丙基二-(5-CH3(CH2)11)磷酸酯、1-丙基二-(6-CH3(CH2)11)磷酸酯、1-丙基二-(1-CH3(CH2)12)磷酸酯、1-丙基二-(2-CH3(CH2)12)磷酸酯、1-丙基二-(3-CH3(CH2)12)磷酸酯、1-丙基二-(4-CH3(CH2)12)磷酸酯、1-丙基二-(5-CH3(CH2)12)磷酸酯、1-丙基二-(6-CH3(CH2)12)磷酸酯、2-丙基二-(1-丁基)磷酸酯、2-丙基二-(2-丁基)磷酸酯、2-丙基二-(1-叔丁基)磷酸酯、2-丙基二-(2-叔丁基)磷酸酯、2-丙基二-(1-戊基)磷酸酯、2-丙基二-(2-戊基)磷酸酯、2-丙基二-(3-戊基)磷酸酯、2-丙基二-(1-己基)磷酸酯、2-丙基二-(2-己基)磷酸酯、2-丙基二-(3-己基)磷酸酯、2-丙基二-(1-庚基)磷酸酯、2-丙基二-(2-庚基)磷酸酯、2-丙基二-(3-庚基)磷酸酯、2-丙基二-(4-庚基)磷酸酯、2-丙基二-(1-辛基)磷酸酯、2-丙基二-(2-辛基)磷酸酯、2-丙基二-(3-辛基)磷酸酯、2-丙基二-(4-辛基)磷酸酯、2-丙基二-(1-CH3(CH2)8)磷酸酯、2-丙基二-(2-CH3(CH2)8)磷酸酯、2-丙基二-(3-CH3(CH2)8)磷酸酯、2-丙基二-(4-CH3(CH2)8)磷酸酯、2-丙基二-(1-CH3(CH2)9)磷酸酯、2-丙基二-(2-CH3(CH2)9)磷酸酯、2-丙基二-(3-CH3(CH2)9)磷酸酯、2-丙基二-(4-CH3(CH2)9)磷酸酯、2-丙基二-(5-CH3(CH2)9)磷酸酯、、2-丙基二-(1-CH3(CH2)10)磷酸酯、2-丙基二-(2-CH3(CH2)10)磷酸酯、2-丙基二-(3-CH3(CH2)10)磷酸酯、2-丙基二-(4-CH3(CH2)10)磷酸酯、2-丙基二-(5-CH3(CH2)10)磷酸酯、2-丙基二-(1-CH3(CH2)11)磷酸酯、2-丙基二-(2-CH3(CH2)11)磷酸酯、2-丙基二-(3-CH3(CH2)11)磷酸酯、2-丙基二-(4-CH3(CH2)11)磷酸酯、2-丙基二-(5-CH3(CH2)11)磷酸酯、2-丙基二-(6-CH3(CH2)11)磷酸酯、2-丙基二-(1-CH3(CH2)12)磷酸酯、2-丙基二-(2-CH3(CH2)12)磷酸酯、2-丙基二-(3-CH3(CH2)12)磷酸酯、2-丙基二-(4-CH3(CH2)12)磷酸酯、2-丙基二-(5-CH3(CH2)12)磷酸酯、2-丙基二-(6-CH3(CH2)12)磷酸酯、丁基二-(1-叔丁基)磷酸酯、丁基二-(2-叔丁基)磷酸酯、丁基二-(1-戊基)磷酸酯、丁基二-(2-戊基)磷酸酯、丁基二-(3-戊基)磷酸酯、丁基二-(1-己基)磷酸酯、丁基二-(2-己基)磷酸酯、丁基二-(3-己基)磷酸酯、丁基二-(1-庚基)磷酸酯、丁基二-(2-庚基)磷酸酯、丁基二-(3-庚基)磷酸酯、丁基二-(4-庚基)磷酸酯、丁基二-(1-辛基)磷酸酯、丁基二-(2-辛基)磷酸酯、丁基二-(3-辛基)磷酸酯、丁基二-(4-辛基)磷酸酯、丁基二-(1-CH3(CH2)8)磷酸酯、丁基二-(2-CH3(CH2)8)磷酸酯、丁基二-(3-CH3(CH2)8)磷酸酯、丁基二-(4-CH3(CH2)8)磷酸酯、丁基二-(1-CH3(CH2)9)磷酸酯、丁基二-(2-CH3(CH2)9)磷酸酯、丁基二-(3-CH3(CH2)9)磷酸酯、丁基二-(4-CH3(CH2)9)磷酸酯、丁基二-(5-CH3(CH2)9)磷酸酯、、丁基二-(1-CH3(CH2)10)磷酸酯、丁基二-(2-CH3(CH2)10)磷酸酯、丁基二-(3-CH3(CH2)10)磷酸酯、丁基二-(4-CH3(CH2)10)磷酸酯、丁基二-(5-CH3(CH2)10)磷酸酯、丁基二-(1-CH3(CH2)11)磷酸酯、丁基二-(2-CH3(CH2)11)磷酸酯、丁基二-(3-CH3(CH2)11)磷酸酯、丁基二-(4-CH3(CH2)11)磷酸酯、丁基二-(5-CH3(CH2)11)磷酸酯、丁基二-(6-CH3(CH2)11)磷酸酯、丁基二-(1-CH3(CH2)12)磷酸酯、丁基二-(2-CH3(CH2)12)磷酸酯、丁基二-(3-CH3(CH2)12)磷酸酯、丁基二-(4-CH3(CH2)12)磷酸酯、丁基二-(5-CH3(CH2)12)磷酸酯、丁基二-(6-CH3(CH2)12)磷酸酯、甲基乙基丙基磷酸酯、甲基乙基丁基磷酸酯、甲基乙基戊基磷酸酯、甲基乙基己基磷酸酯、甲基乙基庚基磷酸酯、甲基乙基辛基磷酸酯、甲基丙基丁基磷酸酯、甲基丙基戊基磷酸酯、甲基丙基己基磷酸酯、甲基丙基庚基磷酸酯、甲基丙基辛基磷酸酯、甲基丁基戊基磷酸酯、甲基丁基己基磷酸酯、甲基丁基庚基磷酸酯、甲基丁基辛基磷酸酯、甲基戊基己基磷酸酯、甲基戊基庚基磷酸酯、甲基戊基辛基磷酸酯、甲基己基庚基磷酸酯、甲基己基辛基磷酸酯、乙基丙基丁基磷酸酯、乙基丙基戊基磷酸酯、乙基丙基己基磷酸酯、乙基丙基庚基磷酸酯、乙基丙基辛基磷酸酯、乙基丁基戊基磷酸酯、乙基丁基己基磷酸酯、乙基丁基庚基磷酸酯、乙基丁基辛基磷酸酯、乙基戊基己基磷酸酯、乙基戊基庚基磷酸酯、乙基戊基辛基磷酸酯、乙基己基庚基磷酸酯、乙基己基辛基磷酸酯、三-苯基磷酸酯、甲基二-苯基磷酸酯、乙基二-苯基磷酸酯、1-丙基二-苯基磷酸酯、2-丙基二苯基磷酸酯、1-丁基二-苯基磷酸酯、2-丁基二苯基磷酸酯、1-叔丁基二-苯基磷酸酯、2-叔丁基二苯基磷酸酯、1-戊基二-苯基磷酸酯、2-戊基二苯基磷酸酯、3-戊基二苯基磷酸酯、1-己基二-苯基磷酸酯、2己基二苯基磷酸酯、3-己基二苯基磷酸酯、1-庚基戊基二-苯基磷酸酯、2庚基二苯基磷酸酯、3-庚基二苯基磷酸酯、4-庚基二-苯基磷酸酯、1-辛基戊基二-苯基磷酸酯、2辛基二苯基磷酸酯、3-辛基二苯基磷酸酯、4-辛基二-苯基磷酸酯、1-CH3(CH2)8二-苯基磷酸酯、2-CH3(CH2)8二-苯基磷酸酯、3-CH3(CH2)8二-苯基磷酸酯、4-CH3(CH2)8二-苯基磷酸酯、1-CH3(CH2)9二-苯基磷酸酯、2-CH3(CH2)9二-苯基磷酸酯、3-CH3(CH2)9二-苯基磷酸酯、4-CH3(CH2)9二-苯基磷酸酯、5-CH3(CH2)9二-苯基磷酸酯、、1-CH3(CH2)10二-苯基磷酸酯、2-CH3(CH2)10二-苯基磷酸酯、3-CH3(CH2)10二-苯基磷酸酯、4-CH3(CH2)10二-苯基磷酸酯、5-CH3(CH2)10二-苯基磷酸酯、、1-CH3(CH2)11二-苯基磷酸酯、2-CH3(CH2)11二-苯基磷酸酯、3-CH3(CH2)11二-苯基磷酸酯、4-CH3(CH2)11二-苯基磷酸酯、5-CH3(CH2)11二-苯基磷酸酯、6-CH3(CH2)11二-苯基磷酸酯、1-CH3(CH2)12二-苯基磷酸酯、2-CH3(CH2)12二-苯基磷酸酯、3-CH3(CH2)12二-苯基磷酸酯、4-CH3(CH2)12二-苯基磷酸酯、5-CH3(CH2)12二-苯基磷酸酯、6-CH3(CH2)12二-苯基磷酸酯、二-甲基苯基磷酸酯、二-乙基苯基磷酸酯、二-(1-丙基)苯基磷酸酯、二-(2-丙基)苯基磷酸酯、二-(-异丙)苯基磷酸酯、二-(1-丁基)苯基磷酸酯、二-(2-丁基)苯基磷酸酯、二-(1-叔丁基)苯基磷酸酯、二-(2-叔丁基)苯基磷酸酯、二-(1-戊基)苯基磷酸酯、二-(2-戊基)苯基磷酸酯、二-(3-戊基)苯基磷酸酯、二-(1-己基)苯基磷酸酯、二-(2-己基)苯基磷酸酯、二-(3-己基)苯基磷酸酯、二-(1-庚基)苯基磷酸酯、二-(2-庚基)苯基磷酸酯、二-(3-庚基)苯基磷酸酯、二-(4-庚基)苯基磷酸酯、二-(1-辛基)苯基磷酸酯、二-(2-辛基)苯基磷酸酯、二-(3-辛基)苯基磷酸酯、二-(4-辛基)苯基磷酸酯、二-(1-CH3(CH2)8)苯基磷酸酯、二-(2-CH3(CH2)8)苯基磷酸酯、二-(3-CH3(CH2)8)苯基磷酸酯、二-(4-CH3(CH2)8)苯基磷酸酯、二-(1-CH3(CH2)9)苯基磷酸酯、二-(2-CH3(CH2)9)苯基磷酸酯、二-(3-CH3(CH2)9)苯基磷酸酯、二-(4-CH3(CH2)9)苯基磷酸酯、二-(5-CH3(CH2)9)苯基磷酸酯、二-(1-CH3(CH2)10)苯基磷酸酯、二-(2-CH3(CH2)10)苯基磷酸酯、二-(3-CH3(CH2)10)苯基磷酸酯、二-(4-CH3(CH2)10)苯基磷酸酯、二-(5-CH3(CH2)10)苯基磷酸酯、二-(1-CH3(CH2)11)苯基磷酸酯、二-(2-CH3(CH2)11)苯基磷酸酯、二-(3-CH3(CH2)11)苯基磷酸酯、二-(4-CH3(CH2)11)苯基磷酸酯、二-(5-CH3(CH2)11)苯基磷酸酯、二-(6-CH3(CH2)11)苯基磷酸酯、二-(1-CH3(CH2)12)苯基磷酸酯、二-(2-CH3(CH2)12)苯基磷酸酯、二-(3-CH3(CH2)12)苯基磷酸酯、二-(4-CH3(CH2)12)苯基磷酸酯、二-(5-CH3(CH2)12)苯基磷酸酯、二-(6-CH3(CH2)12)苯基磷酸酯、三-乙烯磷酸酯、三-(1-丙烯)磷酸酯、三-(2-丙烯)磷酸酯、三-(3-丙烯)磷酸酯、 三-(1-(1-丁烯))磷酸酯、三-(2-(1-丁烯))磷酸酯、三-(3-(1-丁烯))磷酸酯、三-(4-(1-丁烯))磷酸酯、三-(1-(2-丁烯))磷酸酯、三-(2-(2-丁烯))磷酸酯、三-(3-(2-丁烯))磷酸酯、三-(4-(2-丁烯))磷酸酯、 三-(1-(1-戊烯))磷酸酯、三-(2-(1-戊烯))磷酸酯、三-(3-(1-戊烯))磷酸酯、三-(4-(1-戊烯))磷酸酯、三-(5-(1-戊烯))磷酸酯、三-(1-(2-戊烯))磷酸酯、三-(2-(2-戊烯))磷酸酯、三-(3-(2-戊烯))磷酸酯、三-(4-(2-戊烯))磷酸酯、三-(5-(2-戊烯))磷酸酯、三-(1-(1-己烯))磷酸酯、三-(2-(1-己烯))磷酸酯、三-(3-(1-己烯))磷酸酯、三-(4-(1-己烯))磷酸酯、三-(5-(1-己烯))磷酸酯、三-(6-(1-己烯))磷酸酯、三-(1-(2-己烯))磷酸酯、三-(2-(2-己烯))磷酸酯、三-(3-(2-己烯))磷酸酯、三-(4-(2-己烯))磷酸酯、三-(5-(2-己烯))磷酸酯、三-(6-(2-己烯))磷酸酯、三-(苯基甲基)磷酸酯、三-(2-甲基苯基)磷酸酯、三-(3-甲基苯基)磷酸酯、三-(4-甲基苯基)磷酸酯、、三-(2-乙基苯基)磷酸酯、三-(3-乙基苯基)磷酸酯、三-(4-乙基苯基)磷酸酯。
二-磷酸酯的详细实施例包括:
二甲基磷酸酯、二乙基磷酸酯、二-(1-丙基)磷酸酯、二-(2-丙基)磷酸酯、二-(1-丁基)磷酸酯、二-(2-丁基)磷酸酯、二-(1-叔丁基)磷酸酯、二-(2-叔丁基)磷酸酯、二-(1-戊基)磷酸酯、二-(2-戊基)磷酸酯、二-(3-戊基)磷酸酯、二-(1-己基)磷酸酯、二-(2-己基)磷酸酯、二-(3-己基)磷酸酯、二-(1-庚基)磷酸酯、二-(2-庚基)磷酸酯、二-(3-庚基)磷酸酯、二-(4-庚基)磷酸酯、二-(1-辛基)磷酸酯、二-(2-辛基)磷酸酯、二-(3-辛基)磷酸酯、二-(4-辛基)磷酸酯、二-(1-CH3(CH2)8)磷酸酯、二-(2-CH3(CH2)8)磷酸酯、二-(3-CH3(CH2)8)磷酸酯、二-(4-CH3(CH2)8)磷酸酯、二-(1-CH3(CH2)9)磷酸酯、二-(2-CH3(CH2)9)磷酸酯、二-(3-CH3(CH2)9)磷酸酯、二-(4-CH3(CH2)9)磷酸酯、二-(5-CH3(CH2)9)磷酸酯、二-(1-CH3(CH2)10)磷酸酯、二-(2-CH3(CH2)10)磷酸酯、二-(3-CH3(CH2)10)磷酸酯、二-(4-CH3(CH2)10)磷酸酯、二-(5-CH3(CH2)10)磷酸酯、、二-(1-CH3(CH2)11)磷酸酯、二-(2-CH3(CH2)11)磷酸酯、二-(3-CH3(CH2)11)磷酸酯、二-(4-CH3(CH2)11)磷酸酯、二-(5-CH3(CH2)11)磷酸酯、二-(6-CH3(CH2)11)磷酸酯、二-(1-CH3(CH2)12)磷酸酯、二-(2-CH3(CH2)12)磷酸酯、二-(3-CH3(CH2)12)磷酸酯、二-(4-CH3(CH2)12)磷酸酯、二-(5-CH3(CH2)12)磷酸酯、二-(6-CH3(CH2)12)磷酸酯、二-(1-(甲基戊基))磷酸酯、二-(2-(甲基戊基))磷酸酯、二-(3-(甲基戊基))磷酸酯、二-(1-(二-甲基戊基))磷酸酯、二-(2-(二-甲基戊基))磷酸酯、二-(3-(二-甲基戊基))磷酸酯、二-(1-(乙基戊基))磷酸酯、二-(2-(乙基戊基))磷酸酯、二-(3-(乙基戊基))磷酸酯、二-(1-(甲基己基))磷酸酯、二-(2-(甲基己基))磷酸酯、二-(3-(甲基己基))磷酸酯、二-(1-(二-甲基己基))磷酸酯、二-(2-(二-甲基己基))磷酸酯、二-(3-(二-甲基己基))磷酸酯、二-(1-(乙基己基))磷酸酯、二-(2-(乙基己基))磷酸酯、二-(3-(乙基己基))磷酸酯、二-(甲基庚基)磷酸酯、二-(二-甲基庚基)磷酸酯、二-(乙基庚基)磷酸酯、二-(甲基辛基)磷酸酯、二-(二-甲基辛基)磷酸酯、二-(乙基辛基)磷酸酯、甲基乙基磷酸酯、甲基丙基磷酸酯、甲基丁基磷酸酯、甲基叔丁基磷酸酯、甲基戊基磷酸酯、甲基己基磷酸酯、甲基庚基磷酸酯、甲基辛基磷酸酯、甲基CH3(CH2)8磷酸酯、甲基CH3(CH2)9磷酸酯、甲基CH3(CH2)10磷酸酯、甲基CH3(CH2)11磷酸酯、甲基CH3(CH2)12磷酸酯、乙基丙基磷酸酯、乙基丁基磷酸酯、乙基叔丁基磷酸酯、乙基戊基磷酸酯、乙基己基磷酸酯、乙基庚基磷酸酯、乙基辛基磷酸酯、乙基CH3(CH2)8磷酸酯、乙基CH3(CH2)9磷酸酯、乙基CH3(CH2)10磷酸酯、乙基CH3(CH2)11磷酸酯、乙基CH3(CH2)12磷酸酯、丙基丁基磷酸酯、丙基叔丁基磷酸酯、丙基戊基磷酸酯、丙基己基磷酸酯、丙基庚基磷酸酯、丙基辛基磷酸酯、丙基CH3(CH2)8磷酸酯、丙基CH3(CH2)9磷酸酯、丙基CH3(CH2)10磷酸酯、丙基CH3(CH2)11磷酸酯、丙基CH3(CH2)12磷酸酯、丁基叔丁基磷酸酯、叔丁基戊基磷酸酯、叔丁基己基磷酸酯、叔丁基庚基磷酸酯、叔丁基辛基磷酸酯、叔丁基CH3(CH2)8磷酸酯、叔丁基CH3(CH2)9磷酸酯、叔丁基CH3(CH2)10磷酸酯、叔丁基CH3(CH2)11磷酸酯、叔丁基CH3(CH2)12磷酸酯、戊基己基磷酸酯、戊基庚基磷酸酯、戊基辛基磷酸酯、戊基CH3(CH2)8磷酸酯、戊基CH3(CH2)9磷酸酯、戊基CH3(CH2)10磷酸酯、戊基CH3(CH2)11磷酸酯、戊基CH3(CH2)12磷酸酯、己基庚基磷酸酯、己基辛基磷酸酯、己基CH3(CH2)8磷酸酯、己基CH3(CH2)9磷酸酯、己基CH3(CH2)10磷酸酯、己基CH3(CH2)11磷酸酯、己基CH3(CH2)12磷酸酯、二-丁烯磷酸酯、二-戊烯磷酸酯、二-己烯磷酸酯、二-庚烯磷酸酯和二-辛烯磷酸酯。
一磷酸酯的详细实施例包括:
甲基磷酸酯、乙基磷酸酯、丙基磷酸酯、丁基磷酸酯、戊基磷酸酯、己基磷酸酯、庚基磷酸酯、辛基磷酸酯、CH3(CH2)8磷酸酯、CH3(CH2)9磷酸酯、CH3(CH2)10磷酸酯、CH3(CH2)11磷酸酯、CH3(CH2)12磷酸酯、甲基乙基磷酸酯、甲基丙基磷酸酯、甲基丁基磷酸酯、甲基叔丁基磷酸酯、甲基戊基磷酸酯、甲基己基磷酸酯、甲基庚基磷酸酯、甲基辛基磷酸酯、甲基CH3(CH2)8磷酸酯、甲基CH3(CH2)9磷酸酯、甲基CH3(CH2)10磷酸酯、甲基CH3(CH2)11磷酸酯、甲基CH3(CH2)12磷酸酯、二-甲基乙基磷酸酯、二-甲基丙基磷酸酯、二-甲基丁基磷酸酯、二-甲基叔丁基磷酸酯、二-甲基戊基磷酸酯、二-甲基己基磷酸酯、二-甲基庚基磷酸酯、二-甲基辛基磷酸酯、二-甲基CH3(CH2)8磷酸酯、二-甲基CH3(CH2)9磷酸酯、二-甲基CH3(CH2)10磷酸酯、二-甲基CH3(CH2)11磷酸酯、二-甲基CH3(CH2)12磷酸酯、乙基丙基磷酸酯、乙基丁基磷酸酯、乙基叔丁基磷酸酯、乙基戊基磷酸酯、乙基己基磷酸酯、乙基庚基磷酸酯、乙基辛基磷酸酯、乙基CH3(CH2)8磷酸酯、乙基CH3(CH2)9磷酸酯、乙基CH3(CH2)10磷酸酯、乙基CH3(CH2)11磷酸酯、乙基CH3(CH2)12磷酸酯、丁烯磷酸酯、戊烯磷酸酯、己烯磷酸酯、庚烯磷酸酯、和辛烯磷酸酯。
出于简短的目的,没有提供亚磷酸酯的完整列表;然而,可使用的亚磷酸种类与前表中提供的每种的三、二、一磷酸酯是相对应的。例如,通过简单地将前表中的“磷酸酯”替换成“亚磷酸酯”,就可以迅速地得出适用于本发明的典型的亚磷酸种类。
膦化合物的实施例包括:
三-(1-己基)膦、三-(2-己基)膦、三-(3-己基)膦、三-(1-庚基)膦、三-(2-庚基)膦、三-(3-庚基)膦、三-(4-庚基)膦、三-(1-辛基)膦、三-(2-辛基)膦、三-(3-辛基)膦、三-(4-辛基)膦、三-(1-CH3(CH2)8)膦、三-(2-CH3(CH2)8)膦、三-(3-CH3(CH2)8)膦、三-(4-CH3(CH2)8)膦、三-(1-CH3(CH2)9)膦、三-(2-CH3(CH2)9)膦、三-(3-CH3(CH2)9)膦、三-(4-CH3(CH2)9)膦、三-(5-CH3(CH2)9)膦、三-(1-CH3(CH2)10)膦、三-(2-CH3(CH2)10)膦、三-(3-CH3(CH2)10)膦、三-(4-CH3(CH2)10)膦、三-(5-CH3(CH2)10)膦、三-(1-CH3(CH2)11)膦、三-(2-CH3(CH2)11)膦、三-(3-CH3(CH2)11)膦、三-(4-CH3(CH2)11)膦、三-(5-CH3(CH2)11)膦、三-(6-CH3(CH2)11)膦、三-(1-CH3(CH2)12)膦、三-(2-CH3(CH2)12)膦、三-(3-CH3(CH2)12)膦、三-(4-CH3(CH2)12)膦、三-(5-CH3(CH2)12)膦、三-(6-CH3(CH2)12)膦、甲基二-(1-己基)膦、甲基二-(2-己基)膦、甲基二-(3-己基)膦、甲基二-(1-庚基)膦、甲基二-(2-庚基)膦、甲基二-(3-庚基)膦、甲基二-(4-庚基)膦、甲基二-(1-辛基)膦、甲基二-(2-辛基)膦、甲基二-(3-辛基)膦、甲基二-(4-辛基)膦、甲基二-(1-CH3(CH2)8)膦、甲基二-(2-CH3(CH2)8)膦、甲基二-(3-CH3(CH2)8)膦、甲基二-(4-CH3(CH2)8)膦、甲基二-(1-CH3(CH2)9)膦、甲基二-(2-CH3(CH2)9)膦、甲基二-(3-CH3(CH2)9)膦、甲基二-(4-CH3(CH2)9)膦、甲基二-(5-CH3(CH2)9)膦、甲基二-(1-CH3(CH2)10)膦、甲基二-(2-CH3(CH2)10)膦、甲基二-(3-CH3(CH2)10)膦、甲基二-(4-CH3(CH2)10)膦、甲基二-(5-CH3(CH2)10)膦、甲基二-(1-CH3(CH2)11)膦、甲基二-(2-CH3(CH2)11)膦、甲基二-(3-CH3(CH2)11)膦、甲基二-(4-CH3(CH2)11)膦、甲基二-(5-CH3(CH2)11)膦、甲基二-(6-CH3(CH2)11)膦、甲基二-(1-CH3(CH2)12)膦、甲基二-(2-CH3(CH2)12)膦、甲基二-(3-CH3(CH2)12)膦、甲基二-(4-CH3(CH2)12)膦、甲基二-(5-CH3(CH2)12)膦、甲基二-(6-CH3(CH2)12)膦、乙基二-(1-己基)膦、乙基二-(2-己基)膦、乙基二-(3-己基)膦、乙基二-(1-庚基)膦、乙基二-(2-庚基)膦、乙基二-(3-庚基)膦、乙基二-(4-庚基)膦、乙基二-(1-辛基)膦、乙基二-(2-辛基)膦、乙基二-(3-辛基)膦、乙基二-(4-辛基)膦、乙基二-(1-CH3(CH2)8)膦、乙基二-(2-CH3(CH2)8)膦、乙基二-(3-CH3(CH2)8)膦、乙基二-(4-CH3(CH2)8)膦、乙基二-(1-CH3(CH2)9)膦、乙基二-(2-CH3(CH2)9)膦、乙基二-(3-CH3(CH2)9)膦、乙基二-(4-CH3(CH2)9)膦、乙基二-(5-CH3(CH2)9)膦、乙基二-(1-CH3(CH2)10)膦、乙基二-(2-CH3(CH2)10)膦、乙基二-(3-CH3(CH2)10)膦、乙基二-(4-CH3(CH2)10)膦、乙基二-(5-CH3(CH2)10)膦、乙基二-(1-CH3(CH2)11)膦、乙基二-(2-CH3(CH2)11)膦、乙基二-(3-CH3(CH2)11)膦、乙基二-(4-CH3(CH2)11)膦、乙基二-(5-CH3(CH2)11)膦、乙基二-(6-CH3(CH2)11)膦、乙基二-(1-CH3(CH2)12)膦、乙基二-(2-CH3(CH2)12)膦、乙基二-(3-CH3(CH2)12)膦、乙基二-(4-CH3(CH2)12)膦、乙基二-(5-CH3(CH2)12)膦、乙基二-(6-CH3(CH2)12)膦、1-丙基二-(1-己基)膦、1-丙基二-(2-己基)膦、1-丙基二-(3-己基)膦、1-丙基二-(1-庚基)膦、1-丙基二-(2-庚基)膦、1-丙基二-(3-庚基)膦、1-丙基二-(4-庚基)膦、1-丙基二-(1-辛基)膦、1-丙基二-(2-辛基)膦、1-丙基二-(3-辛基)膦、1-丙基二-(4-辛基)膦、1-丙基二-(1-CH3(CH2)8)膦、1-丙基二-(2-CH3(CH2)8)膦、1-丙基二-(3-CH3(CH2)8)膦、1-丙基二-(4-CH3(CH2)8)膦、1-丙基二-(1-CH3(CH2)9)膦、1-丙基二-(2-CH3(CH2)9)膦、1-丙基二-(3-CH3(CH2)9)膦、1-丙基二-(4-CH3(CH2)9)膦、1-丙基二-(5-CH3(CH2)9)膦、1-丙基二-(1-CH3(CH2)10)膦、1-丙基二-(2-CH3(CH2)10)膦、1-丙基二-(3-CH3(CH2)10)膦、1-丙基二-(4-CH3(CH2)10)膦、1-丙基二-(5-CH3(CH2)10)膦、1-丙基二-(1-CH3(CH2)11)膦、1-丙基二-(2-CH3(CH2)11)膦、1-丙基二-(3-CH3(CH2)11)膦、1-丙基二-(4-CH3(CH2)11)膦、1-丙基二-(5-CH3(CH2)11)膦、1-丙基二-(6-CH3(CH2)11)膦、1-丙基二-(1-CH3(CH2)12)膦、1-丙基二-(2-CH3(CH2)12)膦、1-丙基二-(3-CH3(CH2)12)膦、1-丙基二-(4-CH3(CH2)12)膦、1-丙基二-(5-CH3(CH2)12)膦、1-丙基二-(6-CH3(CH2)12)膦、2-丙基二-(1-己基)膦、2-丙基二-(2-己基)膦、2-丙基二-(3-己基)膦、2-丙基二-(1-庚基)膦、2-丙基二-(2-庚基)膦、2-丙基二-(3-庚基)膦、2-丙基二-(4-庚基)膦、2-丙基二-(1-辛基)膦、2-丙基二-(2-辛基)膦、2-丙基二-(3-辛基)膦、2-丙基二-(4-辛基)膦、2-丙基二-(1-CH3(CH2)8)膦、2-丙基二-(2-CH3(CH2)8)膦、2-丙基二-(3-CH3(CH2)8)膦、2-丙基二-(4-CH3(CH2)8)膦、2-丙基二-(1-CH3(CH2)9)膦、2-丙基二-(2-CH3(CH2)9)膦、2-丙基二-(3-CH3(CH2)9)膦、2-丙基二-(4-CH3(CH2)9)膦、2-丙基二-(5-CH3(CH2)9)膦、2-丙基二-(1-CH3(CH2)10)膦、2-丙基二-(2-CH3(CH2)10)膦、2-丙基二-(3-CH3(CH2)10)膦、2-丙基二-(4-CH3(CH2)10)膦、2-丙基二-(5-CH3(CH2)10)膦、、2-丙基二-(1-CH3(CH2)11)膦、2-丙基二-(2-CH3(CH2)11)膦、2-丙基二-(3-CH3(CH2)11)膦、2-丙基二-(4-CH3(CH2)11)膦、2-丙基二-(5-CH3(CH2)11)膦、2-丙基二-(6-CH3(CH2)11)膦、2-丙基二-(1-CH3(CH2)12)膦、2-丙基二-(2-CH3(CH2)12)膦、2-丙基二-(3-CH3(CH2)12)膦、2-丙基二-(4-CH3(CH2)12)膦、2-丙基二-(5-CH3(CH2)12)膦、2-丙基二-(6-CH3(CH2)12)膦、丁基二-(1-己基)膦、丁基二-(2-己基)膦、丁基二-(3-己基)膦、丁基二-(1-庚基)膦、丁基二-(2-庚基)膦、丁基二-(3-庚基)膦、丁基二-(4-庚基)膦、丁基二-(1-辛基)膦、丁基二-(2-辛基)膦、丁基二-(3-辛基)膦、丁基二-(4-辛基)膦、丁基二-(1-CH3(CH2)8)膦、丁基二-(2-CH3(CH2)8)膦、丁基二-(3-CH3(CH2)8)膦、丁基二-(4-CH3(CH2)8)膦、丁基二-(1-CH3(CH2)9)膦、丁基二-(2-CH3(CH2)9)膦、丁基二-(3-CH3(CH2)9)膦、丁基二-(4-CH3(CH2)9)膦、丁基二-(5-CH3(CH2)9)膦、丁基二-(1-CH3(CH2)10)膦、丁基二-(2-CH3(CH2)10)膦、丁基二-(3-CH3(CH2)10)膦、丁基二-(4-CH3(CH2)10)膦、丁基二-(5-CH3(CH2)10)膦、、丁基二-(1-CH3(CH2)11)膦、丁基二-(2-CH3(CH2)11)膦、丁基二-(3-CH3(CH2)11)膦、丁基二-(4-CH3(CH2)11)膦、丁基二-(5-CH3(CH2)11)膦、丁基二-(6-CH3(CH2)11)膦、丁基二-(1-CH3(CH2)12)膦、丁基二-(2-CH3(CH2)12)膦、丁基二-(3-CH3(CH2)12)膦、丁基二-(4-CH3(CH2)12)膦、丁基二-(5-CH3(CH2)12)膦、丁基二-(6-CH3(CH2)12)膦、甲基己基庚基膦、甲基己基辛基膦、乙基丙基丁基膦、乙基丙基戊基膦、乙基丙基己基膦、乙基丙基庚基膦、乙基丙基辛基膦、乙基丁基戊基膦、乙基丁基己基膦、乙基丁基庚基膦、乙基丁基辛基膦、乙基戊基己基膦、乙基戊基庚基膦、乙基戊基辛基膦、乙基己基庚基膦、乙基己基辛基膦、三-苯基膦、1-己基二-苯基膦、2己基二苯基膦、3-己基二苯基膦、1-庚基戊基二-苯基膦、2庚基二苯基膦、3-庚基二苯基膦、4-庚基二-苯基膦、1-辛基戊基二-苯基膦、2辛基二苯基膦、3-辛基二苯基膦、4-辛基二-苯基膦、1-CH3(CH2)8二-苯基膦、2-CH3(CH2)8二-苯基膦、3-CH3(CH2)8二-苯基膦、4-CH3(CH2)8二-苯基膦、1-CH3(CH2)9二-苯基膦、2-CH3(CH2)9二-苯基膦、3-CH3(CH2)9二-苯基膦、4-CH3(CH2)9二-苯基膦、5-CH3(CH2)9二-苯基膦、1-CH3(CH2)10二-苯基膦、2-CH3(CH2)10二-苯基膦、3-CH3(CH2)10二-苯基膦、4-CH3(CH2)10二-苯基膦、5-CH3(CH2)10二-苯基膦、、1-CH3(CH2)11二-苯基膦、2-CH3(CH2)11二-苯基膦、3-CH3(CH2)11二-苯基膦、4-CH3(CH2)11二-苯基膦、5-CH3(CH2)11二-苯基膦、6-CH3(CH2)11二-苯基膦、1-CH3(CH2)12二-苯基膦、2-CH3(CH2)12二-苯基膦、3-CH3(CH2)12二-苯基膦、4-CH3(CH2)12二-苯基膦、5-CH3(CH2)12二-苯基膦、6-CH3(CH2)12二-苯基膦、二-(1-己基)苯基膦、二-(2-己基)苯基膦、二-(3-己基)苯基膦、二-(1-庚基)苯基膦、二-(2-庚基)苯基膦、二-(3-庚基)苯基膦、二-(4-庚基)苯基膦、二-(1-辛基)苯基膦、二-(2-辛基)苯基膦、二-(3-辛基)苯基膦、二-(4-辛基)苯基膦、二-(1-CH3(CH2)8)苯基膦、二-(2-CH3(CH2)8)苯基膦、二-(3-CH3(CH2)8)苯基膦、二-(4-CH3(CH2)8)苯基膦、二-(1-CH3(CH2)9)苯基膦、二-(2-CH3(CH2)9)苯基膦、二-(3-CH3(CH2)9)苯基膦、二-(4-CH3(CH2)9)苯基膦、二-(5-CH3(CH2)9)苯基膦、二-(1-CH3(CH2)10)苯基膦、二-(2-CH3(CH2)10)苯基膦、二-(3-CH3(CH2)10)苯基膦、二-(4-CH3(CH2)10)苯基膦、二-(5-CH3(CH2)10)苯基膦、二-(1-CH3(CH2)11)苯基膦、二-(2-CH3(CH2)11)苯基膦、二-(3-CH3(CH2)11)苯基膦、二-(4-CH3(CH2)11)苯基膦、二-(5-CH3(CH2)11)苯基膦、二-(6-CH3(CH2)11)苯基膦、二-(1-CH3(CH2)12)苯基膦、二-(2-CH3(CH2)12)苯基膦、二-(3-CH3(CH2)12)苯基膦、二-(4-CH3(CH2)12)苯基膦、二-(5-CH3(CH2)12)苯基膦、二-(6-CH3(CH2)12)苯基膦、三-(苯基甲基)膦、三-(2-甲基苯基)膦、三-(3-甲基苯基)膦、三-(4-甲基苯基)膦、、三-(2-乙基苯基)膦、三-(3-乙基苯基)膦、三-(4-乙基苯基)膦、三-(己烯)膦、三-(庚烯)膦、三-(辛烯)膦、三-(庚基)膦、三-(庚基)膦、三-(庚基)膦和三-(庚基)膦。
膦的氧化物的实施例与上列的每种膦相对应。通过简单地将“氧”字加到上列每种膦上就可以迅速地得到这类氧化物的名单。
二-膦酸酯的实施例包括:
四-甲基二-膦酸酯、四-乙基二-膦酸酯、四-(1-丙基)二-膦酸酯、四-(2-丙基)二-膦酸酯、四-(1-丁基)二-膦酸酯、四-(2-丁基)二-膦酸酯、四-(1-叔丁基)二-膦酸酯、四-(2-叔丁基)二-膦酸酯、四-(1-戊基)二-膦酸酯、四-(2-戊基)二-膦酸酯、四-(3-戊基)二-膦酸酯、四-(1-己基)二-膦酸酯、四-(2-己基)二-膦酸酯、四-(3-己基)二-膦酸酯、四-(1-庚基)二-膦酸酯、四-(2-庚基)二-膦酸酯、四-(3-庚基)二-膦酸酯、四-(4-庚基)二-膦酸酯、四-(1-辛基)二-膦酸酯、四-(2-辛基)二-膦酸酯、四-(3-辛基)二-膦酸酯、四-(4-辛基)二-膦酸酯、四-(1-CH3(CH2)8)二-膦酸酯、四-(2-CH3(CH2)8)二-膦酸酯、四-(3-CH3(CH2)8)二-膦酸酯、四-(4-CH3(CH2)8)二-膦酸酯、四-(1-CH3(CH2)9)二-膦酸酯、四-(2-CH3(CH2)9)二-膦酸酯、四-(3-CH3(CH2)9)二-膦酸酯、四-(4-CH3(CH2)9)二-膦酸酯、四-(5-CH3(CH2)9)二-膦酸酯、四-(1-CH3(CH2)10)二-膦酸酯、四-(2-CH3(CH2)10)二-膦酸酯、四-(3-CH3(CH2)10)二-膦酸酯、四-(4-CH3(CH2)10)二-膦酸酯、四-(5-CH3(CH2)10)二-膦酸酯、四-(1-CH3(CH2)11)二-膦酸酯、四-(2-CH3(CH2)11)二-膦酸酯、四-(3-CH3(CH2)11)二-膦酸酯、四-(4-CH3(CH2)11)二-膦酸酯、四-(5-CH3(CH2)11)二-膦酸酯、四-(6-CH3(CH2)11)二-膦酸酯、四-(1-CH3(CH2)12)二-膦酸酯、四-(2-CH3(CH2)12)二-膦酸酯、四-(3-CH3(CH2)12)二-膦酸酯、四-(4-CH3(CH2)12)二-膦酸酯、四-(5-CH3(CH2)12)二-膦酸酯、四-(6-CH3(CH2)12)二-膦酸酯、四-苯基二-膦酸酯、二-甲基-(二-乙基)二-膦酸酯,二-甲基-(二-苯基)二-膦酸酯和二-甲基-(二-4-戊烯)二-膦酸酯。
焦磷酸化合物的实施例包括:
四-甲基焦磷酸酯、四-乙基焦磷酸酯、四-(1-丙基)焦磷酸酯、四-(2-丙基)焦磷酸酯、四-(1-丁基)焦磷酸酯、四-(2-丁基)焦磷酸酯、四-(1-叔丁基)焦磷酸酯、四-(2-叔丁基)焦磷酸酯、四-(1-戊基)焦磷酸酯、四-(2-戊基)焦磷酸酯、四-(3-戊基)焦磷酸酯、四-(1-己基)焦磷酸酯、四-(2-己基)焦磷酸酯、四-(3-己基)焦磷酸酯、四-(1-庚基)焦磷酸酯、四-(2-庚基)焦磷酸酯、四-(3-庚基)焦磷酸酯、四-(4-庚基)焦磷酸酯、四-(1-辛基)焦磷酸酯、四-(2-辛基)焦磷酸酯、四-(3-辛基)焦磷酸酯、四-(4-辛基)焦磷酸酯、四-(1-CH3(CH2)8)焦磷酸酯、四-(2-CH3(CH2)8)焦磷酸酯、四-(3-CH3(CH2)8)焦磷酸酯、四-(4-CH3(CH2)8)焦磷酸酯、四-(1-CH3(CH2)9)焦磷酸酯、四-(2-CH3(CH2)9)焦磷酸酯、四-(3-CH3(CH2)9)焦磷酸酯、四-(4-CH3(CH2)9)焦磷酸酯、四-(5-CH3(CH2)9)焦磷酸酯、、四-(1-CH3(CH2)10)焦磷酸酯、四-(2-CH3(CH2)10)焦磷酸酯、四-(3-CH3(CH2)10)焦磷酸酯、四-(4-CH3(CH2)10)焦磷酸酯、四-(5-CH3(CH2)10)焦磷酸酯、四-(1-CH3(CH2)11)焦磷酸酯、四-(2-CH3(CH2)11)焦磷酸酯、四-(3-CH3(CH2)11)焦磷酸酯、四-(4-CH3(CH2)11)焦磷酸酯、四-(5-CH3(CH2)11)焦磷酸酯、四-(6-CH3(CH2)11)焦磷酸酯、四-(1-CH3(CH2)12)焦磷酸酯、四-(2-CH3(CH2)12)焦磷酸酯、四-(3-CH3(CH2)12)焦磷酸酯、四-(4-CH3(CH2)12)焦磷酸酯、四-(5-CH3(CH2)12)焦磷酸酯、四-(6-CH3(CH2)12)焦磷酸酯、四-苯基焦磷酸酯、二-甲基-(二-乙基)焦磷酸酯,二-甲基-(二-苯基)焦磷酸酯和二-甲基-(二-4-戊烯)焦磷酸酯。
添加的含亚磷的化合物包括在A.Toy和E.Walsh所著的“PhosphorusChemistry in Everyday Living”(第二版,1987,ACS,Washington,DC)中描述的那些。例子包括:焦磷酸酯、亚膦酸酯、硫代磷酸酯,硫代膦酸酯、膦酸酯、二硫代磷酸酯、二-二硫代磷酸酯、二硫代膦酸酯、硫代氨基磷酸酯、和焦酰胺。详细种类包括:四丙基二硫代焦硫酸酯,四乙基二硫代焦硫酸酯,O-乙基O-[2-(二异丙基氨基)乙基]甲基亚磷酸酯,O,O-二甲基O-p-硝基乙基硫代磷酸酯,O,O-二乙基O-p-硝基乙基硫代磷酸酯,O,O-二甲基O-(4-硝基-m-甲苯基)硫代磷酸酯,O-乙基O-p-硝苯基苯基硫代膦酸酯,O,O-二乙基O-(3,5,6-三氯-2-吡啶基)硫代磷酸酯,O,O-二乙基O-(2-异丙基-6-甲基-4-嘧啶基)硫代磷酸酯,O,O-二甲基O-[3-甲基-4-(甲基硫代)苯基]硫代磷酸酯,O,O-二甲基(2,2,2-三氯-1-羟基-乙基)膦酸酯,2,2-二氯乙烯基二甲基磷酸酯,1,2-二溴代-2,2-二氯乙基二甲基磷酸酯,2-氯-1-(2,3,4-三氯苯基)乙烯基二甲基磷酸酯,O-(4-溴代-2-氯苯基)O-乙基S-丙基硫代磷酸酯,O-乙基-O-[4-(甲基硫代)苯基]S-丙基二硫代磷酸酯,O-乙基S,S-二丙基二硫代磷酸酯,二乙基巯基琥珀酸酯,S-酯与O,O-二甲基二硫代磷酸酯,S-[(1,1-二甲基-乙基)-硫代]甲基]O,O-二乙基二硫代磷酸酯,O,O-二甲基S-苯二甲酰亚氨基-甲基二硫代磷酸酯,O,O-二甲基S-4-氧代-1,2,3-苯并三嗪3(4H)-基甲基二硫代磷酸酯,O,O’,O”,O-三乙基S,S-亚甲基二-二硫代磷酸酯,S-[(6-氯-2-氧代-3-(2H)苯并口恶唑)甲基]O,O-二乙基二硫代磷酸酯,S-[(p-氯苯基-硫代)甲基O,O-二乙基二硫代磷酸酯,1,4-p-二氧杂环己烷-2,3-二硫羟S,S-二(O,O-二乙基二硫代磷酸酯,O-乙基S-苯基乙基二硫代膦酸酯,O,S-二甲基硫代磷酰胺,O,S-二甲基乙酰基-硫代磷酰胺,1-甲基乙基2-[[乙氧基[(1-甲基乙基)氨基]硫膦基]氧代]苯甲酸酯,二甲基二氯乙烯基磷酸酯,O,O-二乙基S-乙基-硫代甲基二硫代磷酸酯,O,O-二甲基S-(甲基-氨基甲酰基)二硫代磷酸酯,乙基3-甲基-4-(硫代甲基)苯基(1-甲基乙基)氨基膦酸盐,O,O-二甲基O-[2-(甲基氨基甲酰基)-1-甲基-乙烯基]磷酸酯和十八甲基焦磷酸酰胺。
次膦酸酯的详细实施例包括:乙基戊基次膦酸酯、乙基己基次膦酸酯、乙基庚基次膦酸酯、乙基辛基次膦酸酯、乙基癸基次膦酸酯、乙基苯基次膦酸酯、丁基戊基次膦酸酯、丁基己基次膦酸酯、丁基庚基次膦酸酯、戊基二丁基次膦酸酯、己基二丁基次膦酸酯、庚基二丁基次膦酸酯。
次膦酸的实施例包括:戊基次膦酸、己基次膦酸、庚基次膦酸、辛基次膦酸、癸基次膦酸、苯基次膦酸、二戊基次膦酸、二庚基次膦酸、二癸基次膦酸、二苯基次膦酸、苯基己基次膦酸、戊基癸基次膦酸。
三价膦酸的实施例包括:一戊基三价膦酸、一己基三价膦酸、一庚基三价膦酸、一辛基三价膦酸、一癸基三价膦酸、一苯基三价膦酸、二丙基三价膦酸、二戊基三价膦酸、二己基三价膦酸、二癸基三价膦酸、二苯基三价膦酸、丙基癸基三价膦酸。
膦酸酯的实施例包括:己基戊基膦酸酯、庚基戊基膦酸酯、辛基戊基膦酸酯、癸基戊基膦酸酯、苯基戊基膦酸酯、二丁基戊基膦酸酯、二己基膦酸酯、庚基膦酸酯、戊基膦酸酯、辛基膦酸酯、和苯基膦酸酯。
膦酸的实施例包括:戊基膦酸、己基膦酸、庚基膦酸、辛基膦酸、癸基膦酸、苯基膦酸、甲基戊基膦酸、甲基苯基膦酸、戊基膦的酸、辛基瞵的酸、苯基膦的酸、和戊基辛基膦酸。
亚膦酸酯的实施例包括:乙基戊基亚膦酸酯、乙基庚基亚膦酸酯、乙基辛基亚膦酸酯、乙基癸基亚膦酸酯、乙基苯基亚膦酸酯、丁基基戊基亚膦酸酯、丁基庚基亚膦酸酯、丁基辛基亚膦酸酯、丁基庚基亚膦酸酯、二乙基亚膦酸酯、二己基亚膦酸酯、二乙基庚基亚膦酸酯。
亚膦酸的实施例包括:1-戊基亚膦酸、2-戊基亚膦酸、3-戊基亚膦酸、1-己基亚膦酸、2-己基亚膦酸、3-己基亚膦酸、1-庚基亚膦酸、2-庚基亚膦酸、3-庚基亚膦酸、4-庚基亚膦酸、辛基亚膦酸、癸基亚膦酸、和苯基亚膦酸。
复合膜的多孔载体的制造材料对本发明并不重要。任何为甑别层提供物理上的机械力的多孔载体都可以使用,只要孔足够大以使渗透物无障碍通过但又不能大到对支撑形成的甑别层造成影响。通常孔的大小是在10至1000毫微米之间。通常本领域中公知的载体材料包括纤维素酯、聚砜、聚醚砜、聚氯乙烯、氯化聚氯乙烯、聚偏二氟乙烯、聚苯乙烯、聚碳酸酯、聚酰亚胺、聚丙烯腈、和聚酯。载体材料尤其优选的是聚砜。此类载体的在美国专利3926798、4039440、4277344中有所描述,它们在此都列入作为参考。微孔载体的厚度通常是25至125微米,优选为40至75微米。
在本发明中,各种形状的膜在工业上都是适用和有效的。这些包括螺旋缠绕、空心纤维、管状或平板膜。考虑到膜的成分,通常甑别层在其表面涂层的是吸湿聚合物而非聚酰胺。这些聚合物是阴离子、阳离子、中性的、两性离子,如聚合表面活性剂、聚乙烯醇、聚乙烯亚胺和聚丙烯酸。
本发明的膜可以经受如美国专利4765897、5876602和5755964所述的各种后处理,这里将它们列入作为参考。这些后处理可以进一步增强膜的性能,如增加流通率和/或降低盐通过率。
例如,如美国专利5876602所述,膜在暴露的底座上的稳定性(保持流通率和盐通过率的同时)可以通过在膜已经在多孔载体上形成后(无论是平板或元素形态)将膜与pH值至少为10.5的次氯酸盐溶液接触的方式来实现。最佳暴露时间由温度和使用的次氯酸盐的浓度决定。在室温下,实现所述目标的条件通常在10分钟至5小时,以氯测量按重量计算的次氯酸盐浓度为200至10000ppm(按氯计算)时达到。优选的次氯酸盐浓度为500至7000ppm;优选的暴露时间为30分钟至3小时。在优选的实施方案中,膜在进行前述氯处理之前,要经历一次热处理。膜在40℃至100℃下在水中加热30秒至24小时。热处理能够进一步降低盐通过率并进一步清除膜中含有的可能妨碍氯处理的有益结果的杂质。由所需的应用实际决定,两种处理条件可以在所述范围内调整从而单独通过某一处理可以在保持甚至提高流通率时改进盐通过率。两种处理的顺序是至关重要的,因为在氯处理的同时或是之后热处理膜不能带来先热处理再氯处理时得到的改进效果。
另一可以使用的后处理的实施例在美国专利5755964中有所描述,它包括将甑别层与由如下基团组成的胺接触:由一个或多个含一至二个碳的烷基任意替代的氨(烷基可以由选自羟基、苯基、或氨基的一个或多个取代分子任意取代)、丁胺、环己胺、1,6-己二胺和以上物质的混合物。优选的取代氨物质包括如二甲基胺、三乙甲基胺、乙基胺、三乙醇胺、N,N-二甲基乙醇胺、乙二胺、和苯胺。据发现,将上述胺与甑别层接触,流通率会提高而对特定物质的排斥率也会改变。膜的流通增加或是提高的程度可以通过改变所使用的特定的胺、胺的浓度、甑别层与胺的接触时间、接触温度、胺溶液的pH值或共同以上几种情况来控制。随着流通率的提高,膜的选择性也会改变,即膜可以允许一价离子如钠高比例地通过膜,而同时只阻挡二价离子和有机化合物。
用来处理聚酰胺甑别层的胺可以在溶液中、完全不掺水、或者甚至是气相中,只要它能够与聚酰胺接触。对于低分子量的胺通常采用气相,如氨、甲胺和二甲胺。溶剂可以是任何可溶胺的溶剂,只要流通率的增强和膜的性能不会因与溶剂的接触受阻碍。常用的溶剂包括水和有机化合物,如醇类和羟类,条件是载体不会被溶剂溶解。由于容易处理和获得,需要溶剂时通常使用水。
用本发明中的胺处理时,膜的流通率提高的程度由于使用的特定的胺而变化。然而,在大多数情形中至少有一种通常的趋势存在。该趋势是胺中存在的功能基团越多,如醇类和/或胺基,流通率的提高越大。相应地,胺的浓度和接触的时间是相互联系而且影响着流通率的提高程度。要使流通率提高需要的特定胺和甑别层接触的最短时间很大程度上是由胺的浓度决定的。通常,胺的浓度越高,所需的提高流通率的时间就越短。大多数情况中,胺的浓度应该至少为5,优选为至少约20,最优选为至少约50,到100wt%。在室温下,接触的最少时间可以至少约15秒,优选为至少约一分钟,更优选为至少约30分钟。
通常,接触的时间越长,胺的浓度越高,流通率的提高越大。在经过了一段时间的接触后,流通率的增加将到达最大值,就不再增加了。这时,膜可以使用或是继续存放在胺中。达到最高增长点的时间随着使用特定的胺、胺的浓度以及接触温度的不同而不同,但是利用以上揭示的趋势、没有不适当的操作,熟知本领域的人是可以发现该时间的。对大多数的胺和浓度而言,膜的流通率在甑别层已经与胺接触大约5天时达到最大。如果需要缩短最小接触时间,就要提高聚酰胺甑别层的表面温度。尽管通常也使用这种方法,但使用可能需要长时间接触的低浓度的胺是尤其有利的。尽管大约0℃至大约30℃的温度最方便采用,但升高的温度可以缩短必要的接触时间。升高的温度不能太高以至于使膜的性能受损,即不要高于130℃。常用的可以加速膜的流通效果的温度是至少大约30℃,优选为至少约60℃至大约130℃。可以通过在一个类似烘箱或干燥器的装置内将胺和聚酰胺甑别层接触来达到这些温度。常用的烘箱或干燥器包括对流式、红外线或强迫通风干燥器。
与聚酰胺接触的胺溶液的pH值不是本发明的重要方面。然而,pH值不可以太低以至于使用的胺在溶液中沉淀。另一方面,pH值也不能太高以至于聚酰胺甑别层降解或性能降低。本发明的方法中优选的pH值为约7至大约12,对某些胺来说,更高的pH值可以提高流通率的增强度。
采用的将胺与甑别层接触的方法可以是任何能使胺与聚酰胺在充分的时间内缔合以增强流通率。例如,聚酰胺可以部分或全部浸入胺或胺溶液中。胺或胺溶液也可以被通过、被喷上或是被辊在甑别层上。尽管上述方法在胺是气体时也是有效的,但气态胺与甑别层的接触最有利的是在一个封闭的容器内进行以将使用的胺的量降至最低。
改进流通率和舍弃性也可以通过将膜与强无机酸接触进行膜的后处理来实现,如磷酸、聚磷酸、亚磷酸、硫酸等。磷酸的浓度在10至85wt%是尤其优选的。正如美国专利4765987所述,膜可以通过如将水性酸溶液喷在膜上、将膜浸在水性酸溶液中等方式与无机酸接触。在某些实施方案中,酸溶液可以加热。一旦使用无机酸来处理,膜可以进一步用排斥率增强剂处理,如胶体、单宁酸、聚酰胺等,如美国专利4765897所述。
这里使用的以下用语具有如下定义:“排斥率”是未随溶剂通过膜的特定溶解的或分散物质(即溶质)的百分比。排斥率为100减去通过膜的溶解或分散物质的百分比,即溶质通过率,如果溶解物质是盐就是“盐通过率”。“流通率”是在溶剂,通常是水,通过膜的单位面积上的流量。“反渗透膜”是对NaCl的排斥率为大约95%至100%的膜。“毫微过滤膜”是对NaCl的排斥率为大约0%至95%而且对至少一种二价铁或有机化合物的排斥率为大约20%至100%的膜。“聚酰胺”是胺键(-C(O)NH-)沿着分子链的聚合物。“络合剂”、“胺”、和“酰卤”是指混杂的化合物的一种或多种物类。例如,“胺”可以指多官能胺单体的混合物。“重量计算的百分比”、“百分比重量”、“重量百分比”是指100x(溶质的克数/100毫升溶剂)。
实施例:
以下例子是用来帮助阐明本发明的,不应被解释为是限制附加权利要求的范围。除了另行指明的以外,复合膜是在实验室中使用由溶于DMF的16.5%聚砜溶液形成的多孔聚砜载体制造的。载体被切成矩形(11英寸/7英寸),被夹成网架,放在2.5%间苯二胺(MPD)溶液中大约20分钟。然后将吸收了MPD的载体放在纸巾上用橡皮辊子在前后两面棍以清除过量的溶液。然后将载体放在一块塑料板上,在边缘周围安上硅橡胶封圈。将塑料板切出相同大小的口子,口子在封圈内。这被夹紧在边缘形成防渗漏封条。将50ml含1∶2化学计量比(TMC:络合剂)的络合剂的氯化甲磺酰基(TMC)(0.09wt%)的Lsopar L溶液倒在上面。每个实施例中使用的特定络合剂在下表中列出。对比实例中不含络合剂。反应一分钟后,TMC溶液被倒出,将膜用己烷漂洗,在下表所示的时间内干燥。然后将形成的复合膜放在水中,并用2000ppm、pH值在6.5和8之间的NaCl溶液,在130psi的压力下测试。膜在这些测试条件下达30分钟,然后收集并分析其渗透性。结果在下表中列出。由于制作和测试条件的可变性,单独的对比膜和每组制备的膜一起制备并测试,如下表所示。
表1
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
1(对比) | 无 | 60 | 11.7 | 0.79 |
2 | 三-甲基磷酸酯 | 60 | 23.3 | 2.7 |
3 | 三-乙基磷酸酯 | 60 | 13.4 | 0.46 |
4 | 三-丁基磷酸酯 | 60 | 20.3 | 0.88 |
表2
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
5(对比) | 无 | 60 | 12.1 | 1.2 |
6 | 二丁基-亚磷酸酯 | 60 | 14.4 | 0.62 |
表3
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
7(对比) | 无 | 10 | 14.7 | 0.7 |
8 | 二(2-甲基己基)亚磷酸酯 | 10 | 23.7 | 1.06 |
表4
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
9(对比) | 无 | 10 | 13.7 | 0.69 |
10 | 三-苯基膦 | 10 | 22.11 | 2.6 |
11 | 三-乙基磷酸酯 | 10 | 20.5 | 1.5 |
表5
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
12(对比) | 无 | 10 | 16.6 | 0.26 |
13 | 三-苯基膦 | 10 | 31.8 | 3.32 |
14 | 三-苯基磷酸酯 | 10 | 22.9 | 0.34 |
表6
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
15(对比) | 无 | 10 | 12.6 | 0.35 |
16 | 三苯基膦 | 10 | 17.7 | 0.41 |
17 | 三丁基磷酸酯 | 10 | 16.2 | 0.53 |
表7
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
18(对比) | 无 | 10 | 12.0 | 0.38 |
19 | 二叔丁基二异丙基氨基磷酸酯[(CH3)2CH]2NP[OC(CH3)3]2 | 10 | 16.0 | 0.45 |
表8
*TMC与三-辛基膦的化学计量比为4∶1
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
20(对比) | 无 | 10 | 13.8 | 0.38 |
21 | 二丁基丁基膦酸酯CH3(CH2)3P(O)[O(CH2)3CH3]2 | 10 | 16.1 | 0.30 |
22 | *三-辛基膦 | 10 | 17.5 | 0.39 |
表9
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
23(对比) | 无 | 30 | 11.9 | 0.49 |
24 | 50mM二茂铁 | 30 | 14.7 | 0.39 |
25 | 100mM二茂铁 | 30 | 16.5 | 0.37 |
表10
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
26(对比) | 无 | 10 | 14.2 | 0.341 |
27 | 5mM三苯基铋 | 10 | 12.8 | 0.341 |
表11
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
28(对比) | 无 | 10 | 16.6 | 0.259 |
29 | 2.5mM三苯基膦 | 10 | 31.8 | 3.32 |
30 | 2.5mM三苯基磷酸酯 | 10 | 22.9 | 0.343 |
31 | 2.5mM三苯基胂 | 10 | 29.9 | 0.498 |
32 | 2.5mM三苯基锑 | 10 | 25.1 | 0.442 |
表10和表11揭示了与不同三苯基金属和非金属络合剂相关的性能上的不同。正如表10所示,当在含有TMC和Isopar L溶剂的系统中使用时,三辛基铋不是优选的络合剂。
表12
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
33(对比) | 无 | 10 | 13.7 | 0.30 |
34 | 3mM三辛基铝 | 10 | 40.9 | 72 |
35 | 5mM三丁基磷酸酯 | 10 | 19.47 | 0.42 |
表12揭示了优选的与TMC和Isopar L溶剂(如35)一起使用的络合剂和如其不理想的盐通过率所示的被认为总能量值在本发明需要的范围之上的络合剂(如34)的性能上的不同。
表13
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
36(对比) | 无 | 10 | 19.0 | 0.45 |
37 | 铁(III)三TMH | 10 | 16.72 | 0.326 |
38 | 铁(II)二Acac | 10 | 22.8 | 0.65 |
39 | 铁(III)三Acac | 10 | 24.0 | 0.71 |
表14
实施例号 | 络合剂 | 干燥时间(秒) | 流通率(gfd) | 盐通过率(%) |
40(对比) | 无 | 10 | 18.3 | 0.48 |
41 | 钴(III)三Acac | 10 | 19.5 | 0.96 |
42 | 铬(III)三Acac | 10 | 22.0 | 0.50 |
“Acac”代表乙酰丙酮化物(2,4戊二酮),“TMH”代表2,2,6,6四甲基-3,5庚二酮。实施例36-42的试验是在150psi和2000ppm的NaCl中完成的。实施例37的TMC溶液中有浓度为2.5mM的络合剂;实施例38、39、41和42所用的TMC溶液是不含不可溶解成分的饱和溶液。因此实施例38、39、41和42使用的溶液的浓度低于2.5mM。
正如以上表格所示,将本发明络合剂加入多官能酰卤溶液中可以改进得到膜的流通率和/或排斥率(如盐通过率)。
Claims (36)
1.一种制造复合膜的方法,包括多官能胺与多官能酰卤在多孔载体表面的界面聚合,从而在其上形成聚酰胺层,本方法的特征在于,在多官能酰卤与多官能胺反应之前,将一种络合剂与多官能酰卤接触的步骤。
其中所述的络合剂含有选自非硫化原子的结合核,非硫化原子选自传统的IUPAC元素周期表的族IIIA-VIB和元素周期3-6。
2.如权利要求1所述的方法,其中所述的将络合剂与多官能酰卤接触的步骤形成具有如下特征的聚酰胺层:膜已经在反渗透模具中经过以下操作后仍含有残存的可检测量的络合剂结合核:25℃,用24gfd流动率的纯净水流在0.5%至25%之间的渗透回收率下通过膜,持续24小时。
3.如权利要求2所述的方法,其中所述的聚酰胺层的每克聚酰胺中含有至少25微克残留的络合剂结合核。
4.如权利要求1所述的方法,其中所述的由多官能酰卤与络合剂交互作用引起的总能量变化在3.5至20kcals/mole之间。
5.如权利要求4所述的方法,其中所述的络合剂的溶解参数为18至23J1/2cm-3/2,而且其中所述的多官能酰卤与络合剂交互作用引起的总能量的变化在5.0至15.0kcals/mole之间。
6.如权利要求1所述的方法,其中所述的络合剂的溶解参数为大约15至大约26J1/2cm-3/2。
7.如权利要求1所述的方法,其中所述的络合剂可由以下结构式表示:
α(Lxβ)y
其中α是结合核,L是一种相同或不同的化学键合基,β是加溶基团,相同或不同的,包括1-12个碳原子,x是0至1的整数,y是1至5的整数。
8.如权利要求1所述的方法,其中所述的络合剂的结合核是金属。
9.如权利要求1所述的方法,其中所述的络合剂的结合核选自硅和硒。
10.如权利要求1所述的方法,其中所述的络合剂的结合核是选自以下元素中的至少一种:Al、Si、P、As、Sb、Bi、Se、Te、Fe、Cr、Co、Ni、Cu、和Zn。
11.如权利要求1所述的方法,其中所述的多官能胺存在于水溶液中,多官能酰卤存在于含有络合剂的非水性溶液中,其中所述的络合剂在上述非水性溶液中能够充分溶解,其溶解参数为大约15至大约26J1/2cm-3/2,其中所述的溶液依序涂层在多孔载体表面。
12.如权利要求1所述的方法,其中所述的络合剂含有亚磷结合核,而且其中所述的络合剂选自以下化合物中的至少一种:磷酸酯、亚磷酸酯、膦、氧膦、膦酸酯,二膦酸酯、次磷酸酯、phosphinites、亚膦酸盐、焦磷酸酯、焦磷酸胺、磷酰胺、硫代磷酸酯、二硫代磷酸酯、酰氨基硫代磷酸酯。
13.如权利要求1所述的方法,其中所述的络合剂包括由以下结构式表示的化合物:
其中Z是相同或不同的,选自X、O-P-(X)2、P(O)-X2,(P(-X))m-P-X2、(O-P(-X))m-O-P-X2、(P(O)(-X))m-P(O)-X2和(O-P(O)(-X))m-O-P(O)-X2,P是亚磷,O是氧,m是1至5的整数;Y是O或一对非键合电子,X是相同或不同的,选自:R和含一个或多个氧和/或烷基键的R;R是相同或不同的,选自H,和/或含碳部分。
14.如权利要求13所述的方法,其中所述的Z选自C1-C8的脂肪族。
15.如权利要求13所述的方法,其中至少一个R是选自芳香族或杂环基。
16.如权利要求13所述的方法,其中所述的Y是氧;Z是相同或不同的,选自R和含一个或多个氧键的R;R是相同或不同的,选自:H和含C1-C12的部分。
17.如权利要求16所述的方法,其中所述的R选自C1-C8的脂肪族。
18.如权利要求16所述的方法,其中至少一个R是选自芳香族和/或杂环基。
20.如权利要求19所述的方法,其中所述的R选自C1-C8的脂肪族。
21.如权利要求19所述的方法,其中所述的至少一个R选自芳香族。
22.如权利要求19所述的方法,其中所述的至少一个R选自杂环基。
23.如权利要求16所述的方法,其中所述的含亚磷化合物包括由以下结构式表示的化合物:
24.如权利要求23所述的方法,其中所述的R选自C1-C8的脂肪族。
25.如权利要求23所述的方法,其中至少一个R是选自芳香族和/或杂环基。
26.一种制造复合膜的方法,包括以下步骤:用含有多官能胺的水溶液给多孔载体涂层,随后再用含多官能酰卤的有机溶液涂层,以使多官能胺和多官能酰卤互相接触并反应从而在多孔载体上形成聚酰胺层,本方法的特征在于,在多官能酰卤与多官能胺反应之前,将络合剂与多官能酰卤接触的步骤。
其中所述的络合剂的溶解参数为大约15至26J1/2cm-3/2,并且含有一个结合核,该结合核含有至少一种选自传统IUPAC元素周期表的族IIIA-VIB和元素周期3-6的非硫化原素。
27.如权利要求26所述的方法,其中所述的络合剂的结合核是选自以下元素中的至少一种:Al、Si、P、As、Sb、Se、Te、Fe、Cr、Co、Ni、Cu、Zn和Pb。
28.一种复合膜,含有附在多孔载体上的聚酰胺层,其中所述的聚酰胺层含有一种选自传统IUPAC元素周期表的族IIIA-VIB和元素周期3-6的非硫化元素,而且其中所述的所述元素在膜已经在反渗透模具中经过了下述操作后仍在聚酰胺膜中可检测到:25℃,用24gfd流动率的纯净水流在0.5%至25%之间的渗透回收率下通过膜,持续24小时。
29.如权利要求28所述的膜,其每克聚酰胺中含有至少25微克的所述元素。
30.如权利要求29所述的膜,其每克聚酰胺中含有至少50微克的所述元素。
31.如权利要求30所述的膜,其每克聚酰胺中含有至少200微克的所述元素。
32.如权利要求28所述的膜,其中所述的所述元素是金属。
33.如权利要求28所述的膜,其中所述的所述元素是亚磷。
34.如权利要求28所述的膜,其中所述的所述元素选自硅和硒。
35.如权利要求28所述的膜,其中所述的所述元素选自以下元素中的至少一种:Al、Si、As、Sb、Se、Te、Fe、Cr、Co、Ni、Cu和Zn。
36.如权利要求28所述的膜,其中所述的络合剂含有一个亚磷结合核,而且其中所述的络合剂选自以下化合物中的至少一种:磷酸酯、亚磷酸酯、膦、氧膦、膦酸酯,二膦酸酯、次磷酸酯、phosphinites、亚膦酸盐、焦磷酸酯、焦磷酸胺、磷酰胺、硫代磷酸酯、二硫代磷酸酯、酰氨基硫代磷酸酯。
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CN114307652A (zh) * | 2021-12-23 | 2022-04-12 | 中南大学湘雅医院 | 一种硫代磷酸血液净化改性膜及其制备方法 |
CN115055064A (zh) * | 2022-08-17 | 2022-09-16 | 苏州苏瑞膜纳米科技有限公司 | 一种高性能聚酰胺复合反渗透膜的制备方法 |
CN116116235A (zh) * | 2023-02-02 | 2023-05-16 | 中复新水源科技有限公司 | 一种具有自愈合功能的反渗透膜及其制备方法 |
Families Citing this family (179)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0952885B1 (en) * | 1996-12-20 | 2010-09-22 | Siemens Water Technologies Corp. | Scouring method |
US6536605B2 (en) * | 1997-06-06 | 2003-03-25 | Koch Membrane Systems, Inc. | High performance composite membrane |
JP4289757B2 (ja) * | 2000-03-23 | 2009-07-01 | 日東電工株式会社 | 複合逆浸透膜の製造方法 |
US6337018B1 (en) | 2000-04-17 | 2002-01-08 | The Dow Chemical Company | Composite membrane and method for making the same |
AUPR143400A0 (en) * | 2000-11-13 | 2000-12-07 | Usf Filtration And Separations Group Inc. | Modified membranes |
AUPR421501A0 (en) | 2001-04-04 | 2001-05-03 | U.S. Filter Wastewater Group, Inc. | Potting method |
AUPR584301A0 (en) * | 2001-06-20 | 2001-07-12 | U.S. Filter Wastewater Group, Inc. | Membrane polymer compositions |
US20030015470A1 (en) * | 2001-07-20 | 2003-01-23 | Muralidhara Harapanahalli S. | Nanofiltration water-softening apparatus and method |
AUPR692401A0 (en) | 2001-08-09 | 2001-08-30 | U.S. Filter Wastewater Group, Inc. | Method of cleaning membrane modules |
US7247238B2 (en) * | 2002-02-12 | 2007-07-24 | Siemens Water Technologies Corp. | Poly(ethylene chlorotrifluoroethylene) membranes |
AUPS300602A0 (en) * | 2002-06-18 | 2002-07-11 | U.S. Filter Wastewater Group, Inc. | Methods of minimising the effect of integrity loss in hollow fibre membrane modules |
KR20040018716A (ko) * | 2002-08-26 | 2004-03-04 | 삼성전자주식회사 | 무정류자 직류모터의 속도제어장치 및 방법 |
JP4282598B2 (ja) * | 2002-10-10 | 2009-06-24 | シーメンス・ウォーター・テクノロジーズ・コーポレーション | 濾過装置及び該濾過装置を洗浄する方法 |
AU2002953111A0 (en) * | 2002-12-05 | 2002-12-19 | U. S. Filter Wastewater Group, Inc. | Mixing chamber |
WO2005028519A2 (en) * | 2003-02-19 | 2005-03-31 | Vanderbilt University | Polymer matrixes having nanoscale channels and uses |
CN100411719C (zh) * | 2003-03-03 | 2008-08-20 | 通用电气公司 | 半渗透膜的制备方法 |
US7182858B2 (en) * | 2003-03-04 | 2007-02-27 | Kinetico Incorporated | Multiple barrier filter apparatus |
AU2003903507A0 (en) | 2003-07-08 | 2003-07-24 | U. S. Filter Wastewater Group, Inc. | Membrane post-treatment |
EP1677898B1 (en) | 2003-08-29 | 2016-03-09 | Evoqua Water Technologies LLC | Backwash |
JP4427291B2 (ja) * | 2003-09-03 | 2010-03-03 | 東亞合成株式会社 | 機能性膜の連続製造方法 |
WO2005046849A1 (en) | 2003-11-14 | 2005-05-26 | U.S. Filter Wastewater Group, Inc. | Improved module cleaning method |
US8758621B2 (en) | 2004-03-26 | 2014-06-24 | Evoqua Water Technologies Llc | Process and apparatus for purifying impure water using microfiltration or ultrafiltration in combination with reverse osmosis |
EP1747058A4 (en) * | 2004-04-22 | 2009-09-30 | Siemens Water Tech Corp | FILTRATION APPARATUS COMPRISING A MEMBRANE BIOREACTOR AND A TREATMENT TANK FOR THE DIGESTION OF ORGANIC MATERIALS |
US7074256B2 (en) * | 2004-05-13 | 2006-07-11 | Battelle Energy Alliance, Llc | Phosphazene membranes for gas separations |
CA2571498A1 (en) * | 2004-07-02 | 2006-01-12 | U.S. Filter Wastewater Group, Inc. | Gas transfer membrane |
CA2571502A1 (en) | 2004-07-05 | 2006-01-12 | U.S. Filter Wastewater Group, Inc. | Hydrophilic membranes |
WO2006017911A1 (en) * | 2004-08-20 | 2006-02-23 | Siemens Water Technologies Corp. | Square mbr manifolding system |
AU2005282211B2 (en) | 2004-09-07 | 2011-04-21 | Evoqua Water Technologies Llc | Reduction of backwash liquid waste |
CN101039739B (zh) | 2004-09-14 | 2014-10-08 | 伊沃夸水处理技术有限责任公司 | 从薄膜组件上去除固体的方法和设备 |
CA2579894A1 (en) | 2004-09-15 | 2006-03-23 | Siemens Water Technologies Corp. | Continuously variable aeration |
JP4656511B2 (ja) * | 2004-10-04 | 2011-03-23 | 日東電工株式会社 | 複合逆浸透膜の製造方法 |
US7591950B2 (en) * | 2004-11-02 | 2009-09-22 | Siemens Water Technologies Corp. | Submerged cross-flow filtration |
JP2008518748A (ja) * | 2004-11-02 | 2008-06-05 | シーメンス・ウォーター・テクノロジーズ・コーポレーション | 浸漬クロスフロー濾過 |
NL1030346C2 (nl) * | 2004-11-15 | 2006-09-20 | Toray Industries | Semipermeabel composietmembraan, productiewerkwijze daarvan, en element, fluïdumscheidingsinstallatie en werkwijze voor behandeling van water onder toepassing van hetzelfde. |
MY141919A (en) * | 2004-12-03 | 2010-07-30 | Siemens Water Tech Corp | Membrane post treatment |
US8758622B2 (en) | 2004-12-24 | 2014-06-24 | Evoqua Water Technologies Llc | Simple gas scouring method and apparatus |
EP2394731A1 (en) | 2004-12-24 | 2011-12-14 | Siemens Industry, Inc. | Cleaning in membrane filtration systems |
CA2593412A1 (en) * | 2005-01-14 | 2006-07-20 | Siemens Water Technologies Corp. | Filtration system |
CN101137427B (zh) * | 2005-03-09 | 2011-08-03 | 加利福尼亚大学校务委员会 | 纳米复合材料膜及其制备和使用方法 |
EP1885475B1 (en) | 2005-04-29 | 2015-03-25 | Evoqua Water Technologies LLC | Chemical clean for membrane filter |
GB0512248D0 (en) | 2005-06-16 | 2005-07-27 | Bp Exploration Operating | Water flooding method |
US20080214687A1 (en) * | 2005-06-20 | 2008-09-04 | Heinz-Joachim Muller | Cross Linking Treatment of Polymer Membranes |
KR20080042078A (ko) * | 2005-07-12 | 2008-05-14 | 카아길, 인코포레이팃드 | 수명이 연장된 연수화 시스템, 장치 및 방법 |
US7988891B2 (en) | 2005-07-14 | 2011-08-02 | Siemens Industry, Inc. | Monopersulfate treatment of membranes |
EP1913061A1 (en) * | 2005-08-08 | 2008-04-23 | Kolon Industries, Inc. | Method of manufacturing for aromatic polyamide composite membrane |
US7727434B2 (en) * | 2005-08-16 | 2010-06-01 | General Electric Company | Membranes and methods of treating membranes |
SG164499A1 (en) | 2005-08-22 | 2010-09-29 | Siemens Water Tech Corp | An assembly for water filtration using a tube manifold to minimise backwash |
US7510280B2 (en) * | 2005-08-30 | 2009-03-31 | Real D | High yield bonding process for manufacturing polycarbonate polarized lenses |
US7381331B2 (en) * | 2005-09-30 | 2008-06-03 | General Electric Company | Hydrophilic membrane and associated method |
WO2007044415A2 (en) * | 2005-10-05 | 2007-04-19 | Siemens Water Technologies Corp. | Method and apparatus for treating wastewater |
WO2007044345A2 (en) * | 2005-10-05 | 2007-04-19 | Siemens Water Technologies Corp. | Method and apparatus for treating wastewater |
US7537697B2 (en) * | 2006-02-01 | 2009-05-26 | Woongjin Chemical Co., Ltd. | Selective membrane having a high fouling resistance |
US20070251883A1 (en) * | 2006-04-28 | 2007-11-01 | Niu Q Jason | Reverse Osmosis Membrane with Branched Poly(Alkylene Oxide) Modified Antifouling Surface |
WO2007133362A1 (en) * | 2006-05-12 | 2007-11-22 | Dow Global Technologies Inc. | Modified membrane |
JP2008093544A (ja) * | 2006-10-10 | 2008-04-24 | Nitto Denko Corp | 複合半透膜及びその製造方法 |
US8293098B2 (en) | 2006-10-24 | 2012-10-23 | Siemens Industry, Inc. | Infiltration/inflow control for membrane bioreactor |
JP2010508140A (ja) * | 2006-10-27 | 2010-03-18 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 逆浸透薄膜のためのミクロおよびナノ複合支持体構造 |
WO2008097786A2 (en) * | 2007-02-05 | 2008-08-14 | Dow Global Technologies Inc. | Modified polyamide membrane |
JP2008246419A (ja) * | 2007-03-30 | 2008-10-16 | Nitto Denko Corp | 複合半透膜の製造方法 |
CA2682707C (en) | 2007-04-02 | 2014-07-15 | Siemens Water Technologies Corp. | Improved infiltration/inflow control for membrane bioreactor |
US9764288B2 (en) | 2007-04-04 | 2017-09-19 | Evoqua Water Technologies Llc | Membrane module protection |
KR101402291B1 (ko) | 2007-05-29 | 2014-06-02 | 에보쿠아 워터 테크놀로지스 엘엘씨 | 펄스형 공기리프트 펌프를 이용한 막 세정 방법 및 장치 |
CA2700333A1 (en) * | 2007-09-21 | 2009-03-26 | The Regents Of The University Of California | Nanocomposite membranes and methods of making and using same |
KR20100114048A (ko) * | 2007-12-28 | 2010-10-22 | 다우 글로벌 테크놀로지스 인크. | 액정 물질로 침윤된 중합체 나노 입자를 포함하는 위상 보상 필름 |
US20100294989A1 (en) * | 2007-12-28 | 2010-11-25 | Shaffer Ii Edward O | Small scale functional materials |
US8177978B2 (en) | 2008-04-15 | 2012-05-15 | Nanoh20, Inc. | Reverse osmosis membranes |
WO2009148959A2 (en) * | 2008-05-29 | 2009-12-10 | Lawrence Livermore National Security, Llc | Membranes with functionalized carbon nanotube pores for selective transport |
US7993524B2 (en) * | 2008-06-30 | 2011-08-09 | Nanoasis Technologies, Inc. | Membranes with embedded nanotubes for selective permeability |
US20090321355A1 (en) * | 2008-06-30 | 2009-12-31 | NANOASIS TECHNOLOGIES, INC., a corporation of the state of Delaware | Membranes with embedded nanotubes for selective permeability |
US8147735B2 (en) * | 2008-07-09 | 2012-04-03 | Eltron Research & Development, Inc. | Semipermeable polymers and method for producing same |
WO2010009518A1 (en) | 2008-07-24 | 2010-01-28 | Siemens Water Technologies Corp. | Frame system for membrane filtration modules |
AU2009282912B2 (en) | 2008-08-20 | 2014-11-27 | Evoqua Water Technologies Llc | Improved membrane system backwash energy efficiency |
US7815987B2 (en) | 2008-12-04 | 2010-10-19 | Dow Global Technologies Inc. | Polyamide membrane with coating of polyalkylene oxide and polyacrylamide compounds |
DK2393481T3 (da) | 2009-02-03 | 2019-07-15 | Applied Biomimetic As | Nanofabrikeret membran med polymeriserede proteoliposomer |
TWI398353B (zh) * | 2009-03-02 | 2013-06-11 | Ind Tech Res Inst | 奈米纖維材料與脫鹽過濾材料 |
US8580341B2 (en) * | 2009-05-22 | 2013-11-12 | General Electric Company | Method of making composite membrane |
AU2010257526A1 (en) | 2009-06-11 | 2012-01-12 | Siemens Industry, Inc | Methods for cleaning a porous polymeric membrane and a kit for cleaning a porous polymeric membrane |
JP5745512B2 (ja) | 2009-06-29 | 2015-07-08 | ナノエイチツーオー・インコーポレーテッド | 窒素添加剤を含む改良された混成tfcro膜 |
EP2452741A4 (en) * | 2009-07-06 | 2013-12-04 | Sekisui Chemical Co Ltd | POLYMERIC MEMBRANE FOR TREATING WATER |
WO2011005657A1 (en) | 2009-07-09 | 2011-01-13 | Dow Global Technologies Inc. | Spiral wound module including membrane sheet with capillary channels |
WO2011049790A1 (en) | 2009-10-19 | 2011-04-28 | Dow Global Technologies Llc | Method of testing the integrity of spiral wound modules |
WO2011053452A1 (en) | 2009-10-27 | 2011-05-05 | Dow Global Technologies Llc | Method for applying tape layer to outer periphery of spiral wound module |
US20110277631A1 (en) * | 2009-11-12 | 2011-11-17 | National University Of Singapore | Method for modifying a polyimide membrane |
US8557031B1 (en) | 2010-01-07 | 2013-10-15 | Sandia Corporation | Methods for attaching polymerizable ceragenins to water treatment membranes using amine and amide linkages |
US8348499B2 (en) * | 2010-01-12 | 2013-01-08 | Dow Global Technologies Llc | Method of testing spiral wound modules by thermal imaging |
WO2011112351A1 (en) | 2010-03-10 | 2011-09-15 | Dow Global Technologies Llc | Polyamide membrane with a coating comprising polyalkylene oxide and acetophenone compounds |
US8661648B2 (en) * | 2010-03-24 | 2014-03-04 | Dow Global Technologies Llc | Spiral wound filtration module |
WO2011136865A1 (en) | 2010-04-26 | 2011-11-03 | Dow Global Technologies Llc | Polyamide membrane with a coating comprising polyalkylene oxide and triazine compounds |
AU2011245709B2 (en) | 2010-04-30 | 2015-06-11 | Evoqua Water Technologies Llc | Fluid flow distribution device |
WO2011149572A1 (en) | 2010-05-24 | 2011-12-01 | Dow Global Technologies Llc | Polyamide membrane with coating comprising polyalkylene oxide and imidazol compounds |
WO2011149573A1 (en) | 2010-05-24 | 2011-12-01 | Dow Global Technologies Llc | Polyamide membrane with coating comprising polyalkylene oxide and oxy- substituted phenyl compounds |
US8733558B2 (en) | 2010-05-24 | 2014-05-27 | Dow Global Technologies Llc | Composite membrane with coating comprising polyalkylene oxide and biguanide-type compounds |
NO335286B1 (no) * | 2010-06-04 | 2014-11-03 | Tom-Nils Nilsen | Tynnfilmkompositter |
KR101031918B1 (ko) * | 2010-07-16 | 2011-05-02 | 이송근 | 액자형 조립식 간판 프레임 |
US8114478B1 (en) | 2010-09-17 | 2012-02-14 | Dow Global Technologies Llc | Dual-sided membrane sheet and method for making the same |
CN103118766B (zh) | 2010-09-24 | 2016-04-13 | 伊沃夸水处理技术有限责任公司 | 膜过滤系统的流体控制歧管 |
US9216385B2 (en) * | 2010-10-04 | 2015-12-22 | Saudi Arabian Oil Company | Application of rejection enhancing agents (REAs) that do not have cloud point limitations on desalination membranes |
WO2012058038A1 (en) | 2010-10-26 | 2012-05-03 | Dow Global Technologies Llc | Spiral wound module including membrane sheet with regions having different permeabilities |
WO2012064939A2 (en) | 2010-11-10 | 2012-05-18 | Nanoh2O, Inc. | Improved hybrid tfc ro membranes with non-metallic additives |
US20130287944A1 (en) | 2011-01-24 | 2013-10-31 | Dow Global Technologies Llc | Composite polyamide membrane |
US8968828B2 (en) | 2011-01-24 | 2015-03-03 | Dow Global Technologies Llc | Composite polyamide membrane |
WO2012102942A1 (en) | 2011-01-24 | 2012-08-02 | Dow Global Technologies Llc | Composite polyamide membrane |
KR101240956B1 (ko) * | 2011-02-18 | 2013-03-11 | 웅진케미칼 주식회사 | 내오염성능이 우수한 역삼투 복합막 및 그의 제조방법 |
KR101440968B1 (ko) * | 2011-06-17 | 2014-09-17 | 주식회사 엘지화학 | 초친수성 보호층을 포함하는 역삼투막 및 이의 제조방법 |
US8895104B2 (en) * | 2011-07-01 | 2014-11-25 | International Business Machines Corporation | Thin film composite membranes embedded with molecular cage compounds |
US8778182B2 (en) | 2011-07-28 | 2014-07-15 | Dow Global Technologies Llc | Spiral wound element and seal assembly |
CN103764264B (zh) * | 2011-08-31 | 2016-11-16 | 陶氏环球技术有限责任公司 | 源自包含胺反应性官能团和含磷官能团的单体的复合聚酰胺膜 |
US9029600B2 (en) | 2011-09-29 | 2015-05-12 | Dow Global Technologies Llc | Method for preparing high purity mono-hydrolyzed acyl halide compound |
WO2013048801A1 (en) | 2011-09-30 | 2013-04-04 | Siemens Industry, Inc. | Improved manifold arrangement |
HUE058060T2 (hu) | 2011-09-30 | 2022-07-28 | Rohm & Haas Electronic Mat | Szigetelõ szelep |
CN104039429B (zh) | 2012-01-06 | 2016-05-04 | 陶氏环球技术有限责任公司 | 复合聚酰胺膜 |
US9440196B2 (en) | 2012-02-21 | 2016-09-13 | Dow Global Technologies Llc | Composite membrane |
US20150182918A1 (en) | 2012-03-02 | 2015-07-02 | Dow Global Technologies Llc | Multi-pass hyperfiltration system |
RU2492916C1 (ru) * | 2012-03-12 | 2013-09-20 | Закрытое акционерное общество "РМ Нанотех" | Композитная полимерная мембрана для нанофильтрации и способ ее получения |
EP2866922B1 (en) | 2012-06-28 | 2018-03-07 | Evoqua Water Technologies LLC | A potting method |
CN104684632A (zh) | 2012-09-14 | 2015-06-03 | 伊沃夸水处理技术有限责任公司 | 用于膜的聚合物共混物 |
AU2013324056B2 (en) | 2012-09-26 | 2017-11-16 | Evoqua Water Technologies Llc | Membrane securement device |
US9962865B2 (en) | 2012-09-26 | 2018-05-08 | Evoqua Water Technologies Llc | Membrane potting methods |
WO2014052139A1 (en) | 2012-09-27 | 2014-04-03 | Evoqua Water Technologies Llc | Gas scouring apparatus for immersed membranes |
WO2014109945A1 (en) * | 2013-01-14 | 2014-07-17 | Dow Global Technologies Llc | Composite polyamide membrane including tri-hydrocarbyl phosphate |
US9895666B2 (en) | 2013-01-14 | 2018-02-20 | Dow Global Technologies Llc | Composite polyamide membrane made using substituted benzamide monomer |
WO2014109946A1 (en) * | 2013-01-14 | 2014-07-17 | Dow Global Technologies Llc | Composite polyamide membrane |
US9623379B2 (en) | 2013-03-13 | 2017-04-18 | Dow Global Technologies Llc | Spliced fiber-reinforced outer shell for cylindrical filtration element |
WO2014158660A1 (en) | 2013-03-14 | 2014-10-02 | Dow Global Technologies Llc | Composite polyamide membrane including dissolvable polymer coating |
US9051417B2 (en) | 2013-03-16 | 2015-06-09 | Dow Global Technologies Llc | Method for solubilizing carboxylic acid-containing compound in hydrocarbon solvent |
US9289729B2 (en) | 2013-03-16 | 2016-03-22 | Dow Global Technologies Llc | Composite polyamide membrane derived from carboxylic acid containing acyl halide monomer |
US9051227B2 (en) | 2013-03-16 | 2015-06-09 | Dow Global Technologies Llc | In-situ method for preparing hydrolyzed acyl halide compound |
EP2958665B1 (en) | 2013-04-26 | 2018-07-04 | Dow Global Technologies LLC | Assembly including serially connected spiral wound modules with permeate flow controller |
WO2014179024A1 (en) | 2013-05-03 | 2014-11-06 | Dow Global Technologies Llc | Composite polyamide membrane derived from an aliphatic acyclic tertiary amine compound |
CN104209012A (zh) * | 2013-05-29 | 2014-12-17 | 成都慧成科技有限责任公司 | 一种高通量、高盐截留率反渗透膜的制备方法 |
KR101451304B1 (ko) * | 2013-07-18 | 2014-10-16 | 한국화학연구원 | 유·무기 나노복합막의 제조방법 및 이로부터 제조된 유·무기 나노복합막 |
HUE061765T2 (hu) | 2013-10-02 | 2023-08-28 | Rohm & Haas Electronic Mat Singapore Pte Ltd | Berendezés membrán filtrációs modul javítására |
CN105873665B (zh) | 2013-12-02 | 2019-01-01 | 陶氏环球技术有限责任公司 | 用亚硝酸后处理的复合聚酰胺膜 |
US9452391B1 (en) | 2013-12-02 | 2016-09-27 | Dow Global Technologies Llc | Composite polyamide membrane treated with dihyroxyaryl compounds and nitrous acid |
WO2015105632A1 (en) | 2014-01-07 | 2015-07-16 | Dow Global Technologies Llc | Separation of hydrocarbons from aqueous mixture using fouling resistant reverse osmosis membrane |
US20160303519A1 (en) | 2014-01-07 | 2016-10-20 | Dow Global Technologies Llc | Treatment of aqueous mixtures containing anionic surfactants using fouling resistant reverse osmosis membrane |
JP6535010B2 (ja) * | 2014-01-09 | 2019-06-26 | ダウ グローバル テクノロジーズ エルエルシー | 好ましいアゾ含有量を有する複合ポリアミド皮膜 |
WO2015105637A1 (en) | 2014-01-09 | 2015-07-16 | Dow Global Technologies Llc | Composite polyamide membrane having high acid content and low azo content |
JP6535011B2 (ja) | 2014-01-09 | 2019-06-26 | ダウ グローバル テクノロジーズ エルエルシー | アゾ含有量及び高酸含有量を有する複合ポリアミド皮膜 |
KR20160107206A (ko) * | 2014-01-13 | 2016-09-13 | 다우 글로벌 테크놀로지스 엘엘씨 | 고 팽창성 복합 폴리아마이드 멤브레인 |
CN105916573A (zh) | 2014-01-31 | 2016-08-31 | 陶氏环球技术有限责任公司 | 包括纤维素基季铵涂层的复合聚酰胺膜 |
US10258928B2 (en) | 2014-03-31 | 2019-04-16 | Dow Global Technologies Llc | Spiral wound membrane module adapted for high recovery |
US9776141B2 (en) | 2014-04-28 | 2017-10-03 | Dow Global Technologies Llc | Composite polyamide membrane post-treated with nitrous acid |
SG11201609169UA (en) * | 2014-05-08 | 2016-12-29 | Organo Corp | Filtration treatment system and filtration treatment method |
JP6640739B2 (ja) * | 2014-05-14 | 2020-02-05 | ダウ グローバル テクノロジーズ エルエルシー | 亜硝酸で後処理される複合ポリアミド膜 |
US20170065938A1 (en) * | 2014-05-14 | 2017-03-09 | Dow Global Technologies Llc | Composite polyamide membrane post-treated with nitrous acid |
AU2015259613B2 (en) | 2014-05-14 | 2019-07-04 | Dow Global Technologies Llc | Composite polyamide membrane post treated with nitrous acid |
CN104056494B (zh) * | 2014-07-07 | 2016-04-13 | 岳阳唯尔复合材料科技有限公司 | 聚合物超薄亚纳滤复合膜滤芯的溶液涂层连续生产设备及方法 |
US9725344B1 (en) | 2014-09-24 | 2017-08-08 | Dow Global Technologies Llc | Spiral wound filtration assembly including integral bioreactor |
WO2016057427A1 (en) | 2014-10-06 | 2016-04-14 | Lawrence Livermore National Security, Llc | Nanotube trans-membrane channels mimicking biological porins |
AU2016218454A1 (en) | 2015-02-11 | 2017-09-14 | Dow Global Technologies Llc. | Submerged hyperfiltration system |
US10010833B2 (en) | 2015-02-18 | 2018-07-03 | Lg Nanoh2O, Inc. | Spiral wound membrane module with reinforced fold line |
CN107531526B (zh) | 2015-04-16 | 2021-04-06 | 陶氏环球技术有限责任公司 | 包含螺旋卷绕生物反应器和超滤膜模块的过滤总成 |
EP3283197B1 (en) | 2015-04-16 | 2019-06-19 | Dow Global Technologies LLC | Filtration assembly including spiral wound bioreactors and membrane modules positioned in separate pressure vessels |
US9731985B2 (en) * | 2015-06-03 | 2017-08-15 | Lg Nanoh2O, Inc. | Chemical additives for enhancement of water flux of a membrane |
US9695065B2 (en) * | 2015-06-03 | 2017-07-04 | Lg Nanoh2O, Inc. | Combination of chemical additives for enhancement of water flux of a membrane |
US9724651B2 (en) | 2015-07-14 | 2017-08-08 | Lg Nanoh2O, Inc. | Chemical additives for water flux enhancement |
US10322375B2 (en) | 2015-07-14 | 2019-06-18 | Evoqua Water Technologies Llc | Aeration device for filtration system |
JP6683800B2 (ja) | 2015-07-29 | 2020-04-22 | ダウ グローバル テクノロジーズ エルエルシー | 渦巻き状膜モジュール及び塩水シールを含むフィルタアセンブリ |
US9861940B2 (en) | 2015-08-31 | 2018-01-09 | Lg Baboh2O, Inc. | Additives for salt rejection enhancement of a membrane |
KR101892343B1 (ko) * | 2015-09-01 | 2018-08-27 | 주식회사 엘지화학 | 수처리 분리막의 제조방법, 이를 이용하여 제조된 수처리 분리막, 및 수처리 분리막을 포함하는 수처리 모듈 |
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US10155203B2 (en) | 2016-03-03 | 2018-12-18 | Lg Nanoh2O, Inc. | Methods of enhancing water flux of a TFC membrane using oxidizing and reducing agents |
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US12048903B2 (en) | 2016-09-12 | 2024-07-30 | Fluid Technology Solutions (Fts), Inc. | Thin films covalently bonded to cellulose ester membranes and methods of making the same |
JP7121036B2 (ja) | 2017-04-05 | 2022-08-17 | ダウ グローバル テクノロジーズ エルエルシー | 統合圧力モニタリングを含むスパイラル巻きモジュールアセンブリ |
WO2018192549A1 (en) * | 2017-04-19 | 2018-10-25 | The University Of Hong Kong | Thin film composite membrane with nano-sized bubbles having enhanced membrane permeability, preparation methods and uses thereof |
ES2890815T3 (es) | 2017-07-27 | 2022-01-24 | Ddp Specialty Electronic Mat Us Llc | Módulo de membrana enrollada en espiral que incluye supervisión de presión diferencial integrada |
JP7300810B2 (ja) * | 2017-09-15 | 2023-06-30 | 日東電工株式会社 | 複合半透膜及びその製造方法 |
JP2019098329A (ja) * | 2017-11-30 | 2019-06-24 | 東レ株式会社 | 複合半透膜および複合半透膜の製造方法 |
KR20200109321A (ko) | 2018-01-15 | 2020-09-22 | 디디피 스페셜티 일렉트로닉 머티리얼즈 유에스, 인크. | 일체형 유동 제한기 및 센서를 갖는 와권형 조립체 |
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CN110697833A (zh) * | 2019-10-09 | 2020-01-17 | 宁波泰意德过滤技术有限公司 | 一种重金属处理用纳滤膜及其制备方法 |
WO2022152748A1 (en) | 2021-01-13 | 2022-07-21 | Aquaporin A/S | Membrane for water filtration |
Family Cites Families (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US525261A (en) * | 1894-08-28 | Oil-burner attachment | ||
NL82724C (zh) | 1951-06-19 | |||
FR1587422A (zh) * | 1968-10-07 | 1970-03-20 | ||
DE2602493A1 (de) * | 1975-01-27 | 1976-07-29 | Ramot Plastics | Verfahren zur entfernung von harnstoff aus waessrigen loesungen |
JPS54151570A (en) | 1978-05-22 | 1979-11-28 | Teijin Ltd | Selectively permeable composite membrane and its manufacture |
US4277344A (en) * | 1979-02-22 | 1981-07-07 | Filmtec Corporation | Interfacially synthesized reverse osmosis membrane |
CH660852A5 (de) * | 1982-11-23 | 1987-05-29 | Aligena Ag | Dynamische membranen, die sich als duenne polymerschichten auf poroesen, polymeren traegermaterialien befinden. |
US4758343A (en) | 1985-09-20 | 1988-07-19 | Toray Industries, Inc. | Interfacially synthesized reverse osmosis membrane |
US4765897A (en) | 1986-04-28 | 1988-08-23 | The Dow Chemical Company | Polyamide membranes useful for water softening |
US4824574A (en) | 1986-04-28 | 1989-04-25 | The Dow Chemical Company | Novel water softening process using membranes |
US4948506A (en) * | 1986-07-07 | 1990-08-14 | Bend Research, Inc. | Physicochemically functional ultrathin films by interfacial polymerization |
US4834886A (en) * | 1987-01-08 | 1989-05-30 | Filmtec Corporation | Process for making alkali resistant hyperfiltration membrane and resulting product |
JPS63271847A (ja) | 1987-04-28 | 1988-11-09 | Mitsubishi Electric Corp | シヤドウマスク式カラ−ブラウン管 |
JPH0622424B2 (ja) | 1989-08-24 | 1994-03-30 | 株式会社オシキリ | 生地制御システム |
US4950404A (en) | 1989-08-30 | 1990-08-21 | Allied-Signal Inc. | High flux semipermeable membranes |
US4983291A (en) * | 1989-12-14 | 1991-01-08 | Allied-Signal Inc. | Dry high flux semipermeable membranes |
JP2505631B2 (ja) | 1990-08-09 | 1996-06-12 | 東レ株式会社 | 複合半透膜およびその製造方法および高純度水の製造方法 |
JPH04161234A (ja) * | 1990-10-24 | 1992-06-04 | Toray Ind Inc | 複合膜の製造方法 |
US5254261A (en) * | 1991-08-12 | 1993-10-19 | Hydranautics | Interfacially synthesized reverse osmosis membranes and processes for preparing the same |
US5271843A (en) * | 1991-09-09 | 1993-12-21 | Allied-Signal Inc. | Chlorine-tolerant, thin-film composite membrane |
US5271483A (en) | 1992-12-02 | 1993-12-21 | Hong Young K | Apparatus for lifting false floor in swimming pool |
JP3489922B2 (ja) | 1994-12-22 | 2004-01-26 | 日東電工株式会社 | 高透過性複合逆浸透膜の製造方法 |
US5614099A (en) | 1994-12-22 | 1997-03-25 | Nitto Denko Corporation | Highly permeable composite reverse osmosis membrane, method of producing the same, and method of using the same |
US5989426A (en) | 1995-07-05 | 1999-11-23 | Nitto Denko Corp. | Osmosis membrane |
US5755964A (en) | 1996-02-02 | 1998-05-26 | The Dow Chemical Company | Method of treating polyamide membranes to increase flux |
JP3681214B2 (ja) | 1996-03-21 | 2005-08-10 | 日東電工株式会社 | 高透過性複合逆浸透膜 |
JP4080565B2 (ja) * | 1996-04-26 | 2008-04-23 | 大日本インキ化学工業株式会社 | 多孔質体の製造方法および多孔質体 |
US5658460A (en) * | 1996-05-07 | 1997-08-19 | The Dow Chemical Company | Use of inorganic ammonium cation salts to maintain the flux and salt rejection characteristics of reverse osmosis and nanofiltration membranes during drying |
JP3849263B2 (ja) * | 1996-12-27 | 2006-11-22 | 東レ株式会社 | 複合半透膜及びその製造方法 |
US5876602A (en) | 1997-11-04 | 1999-03-02 | The Dow Chemical Company | Treatment of composite polyamide membranes to improve performance |
JP3985387B2 (ja) | 1998-04-27 | 2007-10-03 | 東レ株式会社 | 複合半透膜の製造方法 |
ATE306312T1 (de) * | 1999-06-08 | 2005-10-15 | Nitto Denko Corp | Membranmodul zur trennung von flüssigkeiten und verfahren zu seiner herstellung |
US6337018B1 (en) * | 2000-04-17 | 2002-01-08 | The Dow Chemical Company | Composite membrane and method for making the same |
-
2000
- 2000-04-17 US US09/550,527 patent/US6337018B1/en not_active Expired - Lifetime
-
2001
- 2001-04-09 AU AU5524601A patent/AU5524601A/xx active Pending
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- 2001-04-09 DK DK01928384T patent/DK1276551T3/da active
- 2001-04-09 US US09/829,024 patent/US6562266B2/en not_active Expired - Lifetime
- 2001-04-16 TW TW090109021A patent/TWI243707B/zh active
- 2001-11-02 US US10/005,455 patent/US6723241B2/en not_active Expired - Lifetime
-
2002
- 2002-10-14 IL IL152286A patent/IL152286A/en not_active IP Right Cessation
- 2002-11-13 US US10/294,440 patent/US6878278B2/en not_active Expired - Lifetime
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JP2003531219A (ja) | 2003-10-21 |
US6562266B2 (en) | 2003-05-13 |
AU2001255246B2 (en) | 2005-02-10 |
ES2328449T3 (es) | 2009-11-13 |
WO2001078882A3 (en) | 2002-02-28 |
IL152286A0 (en) | 2003-05-29 |
CN1210093C (zh) | 2005-07-13 |
JP4932120B2 (ja) | 2012-05-16 |
US6723241B2 (en) | 2004-04-20 |
WO2001078882A2 (en) | 2001-10-25 |
EP1276551B1 (en) | 2009-08-19 |
CA2403301C (en) | 2009-08-25 |
KR100839805B1 (ko) | 2008-06-19 |
AU5524601A (en) | 2001-10-30 |
US20030116498A1 (en) | 2003-06-26 |
DK1276551T3 (da) | 2009-11-16 |
DE60139615D1 (de) | 2009-10-01 |
CA2403301A1 (en) | 2001-10-25 |
TWI243707B (en) | 2005-11-21 |
EP1276551A2 (en) | 2003-01-22 |
US20020113008A1 (en) | 2002-08-22 |
US6878278B2 (en) | 2005-04-12 |
US6337018B1 (en) | 2002-01-08 |
KR20030001430A (ko) | 2003-01-06 |
US20010050252A1 (en) | 2001-12-13 |
IL152286A (en) | 2006-10-05 |
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