TWI243707B - Composite membrane and method for making the same - Google Patents
Composite membrane and method for making the same Download PDFInfo
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- TWI243707B TWI243707B TW090109021A TW90109021A TWI243707B TW I243707 B TWI243707 B TW I243707B TW 090109021 A TW090109021 A TW 090109021A TW 90109021 A TW90109021 A TW 90109021A TW I243707 B TWI243707 B TW I243707B
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- Prior art keywords
- phosphate
- phosphine
- bis
- tri
- patent application
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 49
- 239000012528 membrane Substances 0.000 title claims abstract description 36
- 239000002131 composite material Substances 0.000 title claims abstract description 17
- 150000001412 amines Chemical class 0.000 claims abstract description 90
- 239000008139 complexing agent Substances 0.000 claims abstract description 77
- 230000004907 flux Effects 0.000 claims abstract description 41
- 239000004952 Polyamide Substances 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 229920002647 polyamide Polymers 0.000 claims abstract description 17
- 238000001223 reverse osmosis Methods 0.000 claims abstract description 16
- 230000008569 process Effects 0.000 claims abstract description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 332
- 229910019142 PO4 Inorganic materials 0.000 claims description 307
- 239000010452 phosphate Substances 0.000 claims description 305
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 293
- -1 fluorenyl compound Chemical class 0.000 claims description 203
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 168
- 239000010408 film Substances 0.000 claims description 78
- 239000000243 solution Substances 0.000 claims description 61
- 150000003839 salts Chemical class 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 30
- 235000011180 diphosphates Nutrition 0.000 claims description 30
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 29
- 229940122361 Bisphosphonate Drugs 0.000 claims description 28
- 150000004663 bisphosphonates Chemical class 0.000 claims description 28
- 229910052698 phosphorus Inorganic materials 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000011574 phosphorus Substances 0.000 claims description 26
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 24
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 15
- 229920000768 polyamine Polymers 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 230000008859 change Effects 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 10
- 230000000737 periodic effect Effects 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 230000003993 interaction Effects 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 6
- 229910052787 antimony Inorganic materials 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229910052785 arsenic Inorganic materials 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000012466 permeate Substances 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 229910052714 tellurium Inorganic materials 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000004642 Polyimide Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229920001721 polyimide Polymers 0.000 claims description 4
- 238000004090 dissolution Methods 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 150000003003 phosphines Chemical class 0.000 claims description 3
- VKFFEYLSKIYTSJ-UHFFFAOYSA-N tetraazanium;phosphonato phosphate Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[O-]P([O-])(=O)OP([O-])([O-])=O VKFFEYLSKIYTSJ-UHFFFAOYSA-N 0.000 claims description 3
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 229910052745 lead Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- DAVPISDSWNRILV-UHFFFAOYSA-N P(=O)(O)(O)C1=NC=2NC(NC(C=2N1)=O)=O Chemical compound P(=O)(O)(O)C1=NC=2NC(NC(C=2N1)=O)=O DAVPISDSWNRILV-UHFFFAOYSA-N 0.000 claims 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims 2
- 238000011084 recovery Methods 0.000 claims 2
- 239000004254 Ammonium phosphate Substances 0.000 claims 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 claims 1
- 235000019289 ammonium phosphates Nutrition 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 150000002632 lipids Chemical group 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 150000008300 phosphoramidites Chemical class 0.000 claims 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims 1
- 238000001728 nano-filtration Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 150000001266 acyl halides Chemical class 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 509
- 235000021317 phosphate Nutrition 0.000 description 306
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 55
- 238000011049 filling Methods 0.000 description 42
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 30
- 229940048084 pyrophosphate Drugs 0.000 description 30
- 230000002079 cooperative effect Effects 0.000 description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 27
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 25
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 24
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 14
- 238000001035 drying Methods 0.000 description 14
- 241000894007 species Species 0.000 description 13
- 239000002585 base Substances 0.000 description 12
- 239000004305 biphenyl Substances 0.000 description 12
- 235000010290 biphenyl Nutrition 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 7
- 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 7
- 230000000717 retained effect Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 229910052776 Thorium Inorganic materials 0.000 description 6
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical class CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 150000007857 hydrazones Chemical class 0.000 description 5
- 238000001471 micro-filtration Methods 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- HLHZHCMELZFILJ-UHFFFAOYSA-N octan-4-yl dihydrogen phosphate Chemical compound CCCCC(CCC)OP(O)(O)=O HLHZHCMELZFILJ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- OSRJBXRUXTUMBY-UHFFFAOYSA-N triheptylphosphane Chemical compound CCCCCCCP(CCCCCCC)CCCCCCC OSRJBXRUXTUMBY-UHFFFAOYSA-N 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- LRNMTOCGEKHHAH-UHFFFAOYSA-N butan-2-yl dihydrogen phosphate Chemical compound CCC(C)OP(O)(O)=O LRNMTOCGEKHHAH-UHFFFAOYSA-N 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- 239000013626 chemical specie Substances 0.000 description 4
- DVZIQPGIAQDYQH-UHFFFAOYSA-N diheptyl hydrogen phosphate Chemical compound CCCCCCCOP(O)(=O)OCCCCCCC DVZIQPGIAQDYQH-UHFFFAOYSA-N 0.000 description 4
- QDMDHWSMYFYOTN-UHFFFAOYSA-N heptan-4-yl dihydrogen phosphate Chemical compound CCCC(CCC)OP(O)(O)=O QDMDHWSMYFYOTN-UHFFFAOYSA-N 0.000 description 4
- IDWOBGCWYWUXCW-UHFFFAOYSA-N hexan-2-yl dihydrogen phosphate Chemical compound CCCCC(C)OP(O)(O)=O IDWOBGCWYWUXCW-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- STMLQIACVZOCHU-UHFFFAOYSA-N octan-2-yl dihydrogen phosphate Chemical compound CCCCCCC(C)OP(O)(O)=O STMLQIACVZOCHU-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
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical class OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000001409 amidines Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- LJJVZJSGXHJIPP-UHFFFAOYSA-N ethylpentyl Chemical group [CH2+]CCC[CH]C[CH2-] LJJVZJSGXHJIPP-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
- 229910052732 germanium Inorganic materials 0.000 description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- CNPKMYBCUOVDCE-UHFFFAOYSA-N heptan-2-yl dihydrogen phosphate Chemical compound CCCCCC(C)OP(O)(O)=O CNPKMYBCUOVDCE-UHFFFAOYSA-N 0.000 description 3
- WUFOXJPREAWDFD-UHFFFAOYSA-N heptan-3-yl dihydrogen phosphate Chemical compound CCCCC(CC)OP(O)(O)=O WUFOXJPREAWDFD-UHFFFAOYSA-N 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
- PHNWGDTYCJFUGZ-UHFFFAOYSA-N hexyl dihydrogen phosphate Chemical compound CCCCCCOP(O)(O)=O PHNWGDTYCJFUGZ-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 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 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 229920002098 polyfluorene Polymers 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 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
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- JGSYKOGZFMBYAQ-UHFFFAOYSA-N CC[P]CC Chemical compound CC[P]CC JGSYKOGZFMBYAQ-UHFFFAOYSA-N 0.000 description 2
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 239000003125 aqueous solvent Substances 0.000 description 1
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- 150000001491 aromatic compounds Chemical class 0.000 description 1
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- VEYMELJZIZTCKO-UHFFFAOYSA-N butyl diheptan-3-yl phosphate Chemical compound CCCCC(CC)OP(=O)(OCCCC)OC(CC)CCCC VEYMELJZIZTCKO-UHFFFAOYSA-N 0.000 description 1
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- LRIOWFFQMMTNAF-UHFFFAOYSA-N butyl diheptyl phosphate Chemical compound CCCCCCCOP(=O)(OCCCC)OCCCCCCC LRIOWFFQMMTNAF-UHFFFAOYSA-N 0.000 description 1
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- KXRDCTOXSGAUJA-UHFFFAOYSA-N butyl dihexyl phosphate Chemical compound CCCCCCOP(=O)(OCCCC)OCCCCCC KXRDCTOXSGAUJA-UHFFFAOYSA-N 0.000 description 1
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- GURGLJZVSNHVCE-UHFFFAOYSA-N butyl dipentan-3-yl phosphate Chemical compound CCCCOP(=O)(OC(CC)CC)OC(CC)CC GURGLJZVSNHVCE-UHFFFAOYSA-N 0.000 description 1
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- DJQFQXHRKYELGT-UHFFFAOYSA-N butyl heptyl hydrogen phosphate Chemical compound CCCCCCCOP(O)(=O)OCCCC DJQFQXHRKYELGT-UHFFFAOYSA-N 0.000 description 1
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- MDUACDVHFVHCRK-UHFFFAOYSA-N butyl-di(heptan-2-yl)phosphane Chemical compound CCCCCC(C)P(CCCC)C(C)CCCCC MDUACDVHFVHCRK-UHFFFAOYSA-N 0.000 description 1
- NRRNMGXRQHERLW-UHFFFAOYSA-N butyl-di(heptan-3-yl)phosphane Chemical compound CCCCC(CC)P(CCCC)C(CC)CCCC NRRNMGXRQHERLW-UHFFFAOYSA-N 0.000 description 1
- WBZJCLRWVREOHH-UHFFFAOYSA-N butyl-di(heptan-4-yl)phosphane Chemical compound CCCCP(C(CCC)CCC)C(CCC)CCC WBZJCLRWVREOHH-UHFFFAOYSA-N 0.000 description 1
- LWQFACWEKHDRLT-UHFFFAOYSA-N butyl-di(hexan-2-yl)phosphane Chemical compound CCCCC(C)P(CCCC)C(C)CCCC LWQFACWEKHDRLT-UHFFFAOYSA-N 0.000 description 1
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- IYNSIOSWDRZKSP-UHFFFAOYSA-N butyl-di(octan-2-yl)phosphane Chemical compound CCCCCCC(C)P(CCCC)C(C)CCCCCC IYNSIOSWDRZKSP-UHFFFAOYSA-N 0.000 description 1
- UGNJZLLOWOWYGQ-UHFFFAOYSA-N butyl-di(octan-3-yl)phosphane Chemical compound CCCCCC(CC)P(CCCC)C(CC)CCCCC UGNJZLLOWOWYGQ-UHFFFAOYSA-N 0.000 description 1
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- OBUOEEUFMIUOIL-UHFFFAOYSA-N butyl-ethyl-heptylphosphane Chemical compound CCCCCCCP(CC)CCCC OBUOEEUFMIUOIL-UHFFFAOYSA-N 0.000 description 1
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- IYEONUWDCJJQLZ-UHFFFAOYSA-N butyl-trihydroxy-undecan-4-yl-lambda5-phosphane Chemical compound CCCCCCCC(CCC)P(O)(O)(O)CCCC IYEONUWDCJJQLZ-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
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
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- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
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- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- JAWGVVJVYSANRY-UHFFFAOYSA-N cobalt(3+) Chemical compound [Co+3] JAWGVVJVYSANRY-UHFFFAOYSA-N 0.000 description 1
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- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
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- 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- LQVWRJVXNVMLKR-UHFFFAOYSA-N decan-3-yl dihydrogen phosphate Chemical compound CCCCCCCC(CC)OP(O)(O)=O LQVWRJVXNVMLKR-UHFFFAOYSA-N 0.000 description 1
- VEUUGZQJNGFYBU-UHFFFAOYSA-N decan-4-yl dihydrogen phosphate Chemical compound CCCCCCC(CCC)OP(O)(O)=O VEUUGZQJNGFYBU-UHFFFAOYSA-N 0.000 description 1
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- 230000001419 dependent effect Effects 0.000 description 1
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- DBUFZLCXJQFEBP-UHFFFAOYSA-N di(heptan-2-yl)-methylphosphane Chemical compound CCCCCC(C)P(C)C(C)CCCCC DBUFZLCXJQFEBP-UHFFFAOYSA-N 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
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- LMYBOJICJLLAHL-UHFFFAOYSA-N di(heptan-2-yl)-propylphosphane Chemical compound CCCCCC(C)P(CCC)C(C)CCCCC LMYBOJICJLLAHL-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
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- ICLSLMPMMCPQST-UHFFFAOYSA-N di(hexan-2-yl)-methylphosphane Chemical compound CCCCC(C)P(C)C(C)CCCC ICLSLMPMMCPQST-UHFFFAOYSA-N 0.000 description 1
- FFXJGANYEWKUQZ-UHFFFAOYSA-N di(hexan-2-yl)-propylphosphane Chemical compound CCCCC(C)P(CCC)C(C)CCCC FFXJGANYEWKUQZ-UHFFFAOYSA-N 0.000 description 1
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- DTQXKAMYVZJNDY-UHFFFAOYSA-N di(hexan-3-yl)-propylphosphane Chemical compound CCCC(CC)P(CCC)C(CC)CCC DTQXKAMYVZJNDY-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
- JRPWZVGPIHSVSX-UHFFFAOYSA-N di(octan-2-yl)-propan-2-ylphosphane Chemical compound CCCCCCC(C)P(C(C)C)C(C)CCCCCC JRPWZVGPIHSVSX-UHFFFAOYSA-N 0.000 description 1
- RCNDVLRYKKZKBS-UHFFFAOYSA-N di(octan-2-yl)-propylphosphane Chemical compound CCCCCCC(C)P(CCC)C(C)CCCCCC RCNDVLRYKKZKBS-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
- SRQYNRZLITUHBC-UHFFFAOYSA-N di(octan-3-yl)-propan-2-ylphosphane Chemical compound CCCCCC(CC)P(C(C)C)C(CC)CCCCC SRQYNRZLITUHBC-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
- CFJYXIAWNRUKOC-UHFFFAOYSA-N di(octan-4-yl)-propan-2-ylphosphane Chemical compound CCCCC(CCC)P(C(C)C)C(CCC)CCCC CFJYXIAWNRUKOC-UHFFFAOYSA-N 0.000 description 1
- UAJUDLKNGNDXKW-UHFFFAOYSA-N di(octan-4-yl)-propylphosphane Chemical compound CCCCC(CCC)P(CCC)C(CCC)CCCC UAJUDLKNGNDXKW-UHFFFAOYSA-N 0.000 description 1
- HDFFVHSMHLDSLO-UHFFFAOYSA-M dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)([O-])OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-M 0.000 description 1
- QZVALCYYGHPQRD-UHFFFAOYSA-N dibutan-2-yl hydrogen phosphate Chemical compound CCC(C)OP(O)(=O)OC(C)CC QZVALCYYGHPQRD-UHFFFAOYSA-N 0.000 description 1
- KOZZHKFDXSNGNX-UHFFFAOYSA-N dibutan-2-yl phenyl phosphate Chemical compound CCC(C)OP(=O)(OC(C)CC)OC1=CC=CC=C1 KOZZHKFDXSNGNX-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
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 1
- FEYYOXFAQQJEIG-UHFFFAOYSA-N dibutyl sulfite Chemical compound CCCCOS(=O)OCCCC FEYYOXFAQQJEIG-UHFFFAOYSA-N 0.000 description 1
- CBAXKGZPFRYMIV-UHFFFAOYSA-N didecyl(trihydroxy)-$l^{5}-phosphane Chemical compound CCCCCCCCCCP(O)(O)(O)CCCCCCCCCC CBAXKGZPFRYMIV-UHFFFAOYSA-N 0.000 description 1
- KLXFSKITMRWDPM-UHFFFAOYSA-N diethyl 2-sulfanylbutanedioate Chemical compound CCOC(=O)CC(S)C(=O)OCC KLXFSKITMRWDPM-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
- UAEWCWCMYQAIDR-UHFFFAOYSA-N diethyl methyl phosphate Chemical compound CCOP(=O)(OC)OCC UAEWCWCMYQAIDR-UHFFFAOYSA-N 0.000 description 1
- ITJPTURSPJESQC-UHFFFAOYSA-N diethyl pentyl phosphate Chemical compound CCCCCOP(=O)(OCC)OCC ITJPTURSPJESQC-UHFFFAOYSA-N 0.000 description 1
- KROAAJPGNMNTTP-UHFFFAOYSA-N diheptan-2-yl hydrogen phosphate Chemical compound CCCCCC(C)OP(O)(=O)OC(C)CCCCC KROAAJPGNMNTTP-UHFFFAOYSA-N 0.000 description 1
- QJERURIAEWFRBH-UHFFFAOYSA-N diheptan-3-yl hydrogen phosphate Chemical compound CCCCC(CC)OP(O)(=O)OC(CC)CCCC QJERURIAEWFRBH-UHFFFAOYSA-N 0.000 description 1
- GQZUIPGTJYLKSK-UHFFFAOYSA-N diheptan-4-yl methyl phosphate Chemical compound CCCC(CCC)OP(=O)(OC)OC(CCC)CCC GQZUIPGTJYLKSK-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
- KHCZGCMALIRTMF-UHFFFAOYSA-N diheptyl phenyl phosphate Chemical compound CCCCCCCOP(=O)(OCCCCCCC)OC1=CC=CC=C1 KHCZGCMALIRTMF-UHFFFAOYSA-N 0.000 description 1
- DNJWGDRCDNRDIL-UHFFFAOYSA-N diheptyl(propan-2-yl)phosphane Chemical compound CCCCCCCP(C(C)C)CCCCCCC DNJWGDRCDNRDIL-UHFFFAOYSA-N 0.000 description 1
- RXLRDQWFWTWSAH-UHFFFAOYSA-N diheptyl(propyl)phosphane Chemical compound CCCCCCCP(CCC)CCCCCCC RXLRDQWFWTWSAH-UHFFFAOYSA-N 0.000 description 1
- TWYAWLYZDNVYPT-UHFFFAOYSA-N dihexan-2-yl hydrogen phosphate Chemical compound CCCCC(C)OP(O)(=O)OC(C)CCCC TWYAWLYZDNVYPT-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
- GJZKQIFATBQWBJ-UHFFFAOYSA-N dihexyl(methyl)phosphane Chemical compound CCCCCCP(C)CCCCCC GJZKQIFATBQWBJ-UHFFFAOYSA-N 0.000 description 1
- ICGRXOJPKLUZID-UHFFFAOYSA-N dihexyl(propan-2-yl)phosphane Chemical compound CCCCCCP(C(C)C)CCCCCC ICGRXOJPKLUZID-UHFFFAOYSA-N 0.000 description 1
- GXIMEGMEYWTKRN-UHFFFAOYSA-N dihexyl(propyl)phosphane Chemical compound CCCCCCP(CCC)CCCCCC GXIMEGMEYWTKRN-UHFFFAOYSA-N 0.000 description 1
- WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- AXDCOWAMLFDLEP-UHFFFAOYSA-N dimethoxyphosphoryl dimethyl phosphate Chemical compound COP(=O)(OC)OP(=O)(OC)OC AXDCOWAMLFDLEP-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OGUWNVAAFURAQD-UHFFFAOYSA-N dimethyl pentyl phosphate Chemical compound CCCCCOP(=O)(OC)OC OGUWNVAAFURAQD-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
- BLTQUMGSCQHJAM-UHFFFAOYSA-N dioctan-3-yl hydrogen phosphate Chemical compound CCCCCC(CC)OP(O)(=O)OC(CC)CCCCC BLTQUMGSCQHJAM-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
- BPWXJCCABQQWQA-UHFFFAOYSA-N dioctan-4-yl hydrogen phosphate Chemical compound CCCCC(CCC)OP(O)(=O)OC(CCC)CCCC BPWXJCCABQQWQA-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
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-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
- AZKYRJFAQUTGPQ-UHFFFAOYSA-N dioctyl(propan-2-yl)phosphane Chemical compound CCCCCCCCP(C(C)C)CCCCCCCC AZKYRJFAQUTGPQ-UHFFFAOYSA-N 0.000 description 1
- PRBYIGPVGVDJLI-UHFFFAOYSA-N dioctyl(propyl)phosphane Chemical compound CCCCCCCCP(CCC)CCCCCCCC PRBYIGPVGVDJLI-UHFFFAOYSA-N 0.000 description 1
- AKQLEQJPAXULST-UHFFFAOYSA-N dipentan-2-yl hydrogen phosphate Chemical compound CCCC(C)OP(O)(=O)OC(C)CCC AKQLEQJPAXULST-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
- WJZUIWBZDGBLKK-UHFFFAOYSA-N dipentyl hydrogen phosphate Chemical compound CCCCCOP(O)(=O)OCCCCC WJZUIWBZDGBLKK-UHFFFAOYSA-N 0.000 description 1
- WJZUIWBZDGBLKK-UHFFFAOYSA-M dipentyl phosphate Chemical compound CCCCCOP([O-])(=O)OCCCCC WJZUIWBZDGBLKK-UHFFFAOYSA-M 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- QVKQJEWZVQFGIY-UHFFFAOYSA-N dipropyl hydrogen phosphate Chemical compound CCCOP(O)(=O)OCCC QVKQJEWZVQFGIY-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- OCATXDXVSFLBRW-UHFFFAOYSA-N ethene;phosphoric acid Chemical compound C=C.OP(O)(O)=O.OP(O)(O)=O OCATXDXVSFLBRW-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- HCDLTAHUJKIXJE-UHFFFAOYSA-N ethoxy(heptyl)phosphinic acid Chemical compound CCCCCCCP(O)(=O)OCC HCDLTAHUJKIXJE-UHFFFAOYSA-N 0.000 description 1
- IMCARZNNWXRLAN-UHFFFAOYSA-N ethoxy(octyl)phosphinic acid Chemical compound CCCCCCCCP(O)(=O)OCC IMCARZNNWXRLAN-UHFFFAOYSA-N 0.000 description 1
- UMBYQXLEVYPMHV-UHFFFAOYSA-N ethoxy(pentyl)phosphinic acid Chemical compound CCCCCP(O)(=O)OCC UMBYQXLEVYPMHV-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- SMHZBABQDPBZSJ-UHFFFAOYSA-N ethyl diheptan-2-yl phosphate Chemical compound CCCCCC(C)OP(=O)(OCC)OC(C)CCCCC SMHZBABQDPBZSJ-UHFFFAOYSA-N 0.000 description 1
- WWCCAGFVZQUJPI-UHFFFAOYSA-N ethyl diheptan-3-yl phosphate Chemical compound CCCCC(CC)OP(=O)(OCC)OC(CC)CCCC WWCCAGFVZQUJPI-UHFFFAOYSA-N 0.000 description 1
- VWUSXGSZDZHRSL-UHFFFAOYSA-N ethyl diheptyl phosphate Chemical compound CCCCCCCOP(=O)(OCC)OCCCCCCC VWUSXGSZDZHRSL-UHFFFAOYSA-N 0.000 description 1
- ZVEVEWIDWZDHKE-UHFFFAOYSA-N ethyl dihexan-2-yl phosphate Chemical compound CCCCC(C)OP(=O)(OCC)OC(C)CCCC ZVEVEWIDWZDHKE-UHFFFAOYSA-N 0.000 description 1
- XMHITHWDFUKKNT-UHFFFAOYSA-N ethyl dihexan-3-yl phosphate Chemical compound CCCC(CC)OP(=O)(OCC)OC(CC)CCC XMHITHWDFUKKNT-UHFFFAOYSA-N 0.000 description 1
- PJUWDWLIKQZRKX-UHFFFAOYSA-N ethyl dihexyl phosphate Chemical class CCCCCCOP(=O)(OCC)OCCCCCC PJUWDWLIKQZRKX-UHFFFAOYSA-N 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
- LNIQAUJVHAMHIQ-UHFFFAOYSA-N ethyl dipentan-2-yl phosphate Chemical compound CCCC(C)OP(=O)(OCC)OC(C)CCC LNIQAUJVHAMHIQ-UHFFFAOYSA-N 0.000 description 1
- KABLEHWCLUCHAT-UHFFFAOYSA-N ethyl dipentan-3-yl phosphate Chemical compound CCC(CC)OP(=O)(OCC)OC(CC)CC KABLEHWCLUCHAT-UHFFFAOYSA-N 0.000 description 1
- KRKNUAGEKOBLSU-UHFFFAOYSA-N ethyl dipentyl phosphate Chemical compound CCCCCOP(=O)(OCC)OCCCCC KRKNUAGEKOBLSU-UHFFFAOYSA-N 0.000 description 1
- JSPBAVGTJNAVBJ-UHFFFAOYSA-N ethyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCC)OC1=CC=CC=C1 JSPBAVGTJNAVBJ-UHFFFAOYSA-N 0.000 description 1
- YYJCIPQEOSOUSV-UHFFFAOYSA-N ethyl dipropan-2-yl phosphate Chemical compound CCOP(=O)(OC(C)C)OC(C)C YYJCIPQEOSOUSV-UHFFFAOYSA-N 0.000 description 1
- ANPYQJSSFZGXFE-UHFFFAOYSA-N ethyl dipropyl phosphate Chemical compound CCCOP(=O)(OCC)OCCC ANPYQJSSFZGXFE-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
- HCIQUGMKXQZZMG-UHFFFAOYSA-N ethyl hexyl hydrogen phosphate Chemical compound CCCCCCOP(O)(=O)OCC HCIQUGMKXQZZMG-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
- 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
- MNKNAPFEXFDRAP-UHFFFAOYSA-M ethyl propyl phosphate Chemical compound CCCOP([O-])(=O)OCC MNKNAPFEXFDRAP-UHFFFAOYSA-M 0.000 description 1
- VRROQFXKEVCQBZ-UHFFFAOYSA-N ethyl(dioctyl)phosphane Chemical compound CCCCCCCCP(CC)CCCCCCCC VRROQFXKEVCQBZ-UHFFFAOYSA-N 0.000 description 1
- ZNOXPPRACNEBIA-UHFFFAOYSA-N ethyl(phenyl)phosphane Chemical compound CCPC1=CC=CC=C1 ZNOXPPRACNEBIA-UHFFFAOYSA-N 0.000 description 1
- JHKPXKJDHILFHA-UHFFFAOYSA-N ethyl-di(heptan-4-yl)phosphane Chemical compound CCCC(CCC)P(CC)C(CCC)CCC JHKPXKJDHILFHA-UHFFFAOYSA-N 0.000 description 1
- UGWGXKVPGFKBNI-UHFFFAOYSA-N ethyl-di(octan-2-yl)phosphane Chemical compound CCCCCCC(C)P(CC)C(C)CCCCCC UGWGXKVPGFKBNI-UHFFFAOYSA-N 0.000 description 1
- JDHCFWIXEGQJJS-UHFFFAOYSA-N ethyl-di(octan-3-yl)phosphane Chemical compound CCCCCC(CC)P(CC)C(CC)CCCCC JDHCFWIXEGQJJS-UHFFFAOYSA-N 0.000 description 1
- RTEDZLVDNZVVHW-UHFFFAOYSA-N ethyl-di(octan-4-yl)phosphane Chemical compound CCCCC(CCC)P(CC)C(CCC)CCCC RTEDZLVDNZVVHW-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
- 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
- RRTXPTNZWBIAKG-UHFFFAOYSA-N ethyl-hexyl-trihydroxy-$l^{5}-phosphane Chemical compound CCCCCCP(O)(O)(O)CC RRTXPTNZWBIAKG-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
- ZIOQQMCUVFIHJZ-UHFFFAOYSA-N ethyl-trihydroxy-octyl-$l^{5}-phosphane Chemical compound CCCCCCCCP(O)(O)(O)CC ZIOQQMCUVFIHJZ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 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
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- GGKJPMAIXBETTD-UHFFFAOYSA-N heptyl dihydrogen phosphate Chemical compound CCCCCCCOP(O)(O)=O GGKJPMAIXBETTD-UHFFFAOYSA-N 0.000 description 1
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- YMRHNWOPOBYBPY-UHFFFAOYSA-N heptyl methyl hydrogen phosphate Chemical compound CCCCCCCOP(O)(=O)OC YMRHNWOPOBYBPY-UHFFFAOYSA-N 0.000 description 1
- GGKJPMAIXBETTD-UHFFFAOYSA-L heptyl phosphate Chemical compound CCCCCCCOP([O-])([O-])=O GGKJPMAIXBETTD-UHFFFAOYSA-L 0.000 description 1
- FEKFIHUXXGOQDC-UHFFFAOYSA-N heptyl-hexyl-methylphosphane Chemical compound CCCCCCCP(C)CCCCCC FEKFIHUXXGOQDC-UHFFFAOYSA-N 0.000 description 1
- VAJFLSRDMGNZJY-UHFFFAOYSA-N heptylphosphonic acid Chemical compound CCCCCCCP(O)(O)=O VAJFLSRDMGNZJY-UHFFFAOYSA-N 0.000 description 1
- DEKKNVOOBDLURO-UHFFFAOYSA-N hexan-2-ylphosphonic acid Chemical compound CCCCC(C)P(O)(O)=O DEKKNVOOBDLURO-UHFFFAOYSA-N 0.000 description 1
- LYEBVZZLFOFERJ-UHFFFAOYSA-N hexan-3-ylphosphinic acid Chemical compound C(C)C(CCC)P(O)=O LYEBVZZLFOFERJ-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- MUEVYRUGFRAAIB-UHFFFAOYSA-N hexyl methyl hydrogen phosphate Chemical compound CCCCCCOP(O)(=O)OC MUEVYRUGFRAAIB-UHFFFAOYSA-N 0.000 description 1
- XWKFRUCQRXQQIF-UHFFFAOYSA-N hexyl pentyl hydrogen phosphate Chemical compound CCCCCCOP(O)(=O)OCCCCC XWKFRUCQRXQQIF-UHFFFAOYSA-N 0.000 description 1
- PHNWGDTYCJFUGZ-UHFFFAOYSA-L hexyl phosphate Chemical compound CCCCCCOP([O-])([O-])=O PHNWGDTYCJFUGZ-UHFFFAOYSA-L 0.000 description 1
- JAXRBLAJXQMBAK-UHFFFAOYSA-N hexyl-methyl-octylphosphane Chemical compound CCCCCCCCP(C)CCCCCC JAXRBLAJXQMBAK-UHFFFAOYSA-N 0.000 description 1
- GJWAEWLHSDGBGG-UHFFFAOYSA-N hexylphosphonic acid Chemical compound CCCCCCP(O)(O)=O GJWAEWLHSDGBGG-UHFFFAOYSA-N 0.000 description 1
- 239000012510 hollow fiber Substances 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 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
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
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- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
- MGHBWQMOJPRVKE-UHFFFAOYSA-N methyl dioctan-3-yl phosphate Chemical compound CCCCCC(CC)OP(=O)(OC)OC(CC)CCCCC MGHBWQMOJPRVKE-UHFFFAOYSA-N 0.000 description 1
- QRFTZUVEVYZZKT-UHFFFAOYSA-N methyl dioctyl phosphate Chemical compound CCCCCCCCOP(=O)(OC)OCCCCCCCC QRFTZUVEVYZZKT-UHFFFAOYSA-N 0.000 description 1
- VOWPVJACXJNHBC-UHFFFAOYSA-N methyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OC)OC1=CC=CC=C1 VOWPVJACXJNHBC-UHFFFAOYSA-N 0.000 description 1
- FKOZQALYXWKSAF-UHFFFAOYSA-N methyl dipropan-2-yl phosphate Chemical class CC(C)OP(=O)(OC)OC(C)C FKOZQALYXWKSAF-UHFFFAOYSA-N 0.000 description 1
- KCJPXMHUFVFEGM-UHFFFAOYSA-N methyl dipropyl phosphate Chemical compound CCCOP(=O)(OC)OCCC KCJPXMHUFVFEGM-UHFFFAOYSA-N 0.000 description 1
- GFOAOEDAKIXISY-UHFFFAOYSA-N methyl pentyl hydrogen phosphate Chemical compound CCCCCOP(O)(=O)OC GFOAOEDAKIXISY-UHFFFAOYSA-N 0.000 description 1
- JXWKMMCPAYWOKV-UHFFFAOYSA-M methyl propyl phosphate Chemical compound CCCOP([O-])(=O)OC JXWKMMCPAYWOKV-UHFFFAOYSA-M 0.000 description 1
- BMWOMXHGRVLKCW-UHFFFAOYSA-N methyl(dioctyl)phosphane Chemical compound CCCCCCCCP(C)CCCCCCCC BMWOMXHGRVLKCW-UHFFFAOYSA-N 0.000 description 1
- VIPDUXHNDAXVBZ-UHFFFAOYSA-N methyl-di(octan-4-yl)phosphane Chemical compound CCCCC(CCC)P(C)C(CCC)CCCC VIPDUXHNDAXVBZ-UHFFFAOYSA-N 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000004712 monophosphates Chemical class 0.000 description 1
- XPLOQMVUXWZLET-UHFFFAOYSA-N n-hexylphosphonate ethyl ester Chemical compound CCCCCC[P@@](O)(=O)OCC XPLOQMVUXWZLET-UHFFFAOYSA-N 0.000 description 1
- 239000002120 nanofilm Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- IDNPKSLIPKVTPV-UHFFFAOYSA-N octyl propyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCC IDNPKSLIPKVTPV-UHFFFAOYSA-N 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- OHEMLAUGLPRNIV-UHFFFAOYSA-N octylphosphinic acid Chemical compound CCCCCCCCP(O)=O OHEMLAUGLPRNIV-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- NIFSKIGEQZXNBS-UHFFFAOYSA-N pentan-3-yl dihydrogen phosphate Chemical compound CCC(CC)OP(O)(O)=O NIFSKIGEQZXNBS-UHFFFAOYSA-N 0.000 description 1
- NVTPMUHPCAUGCB-UHFFFAOYSA-L pentyl phosphate Chemical compound CCCCCOP([O-])([O-])=O NVTPMUHPCAUGCB-UHFFFAOYSA-L 0.000 description 1
- CKVICYBZYGZLLP-UHFFFAOYSA-N pentylphosphonic acid Chemical compound CCCCCP(O)(O)=O CKVICYBZYGZLLP-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- NFBAXHOPROOJAW-UHFFFAOYSA-N phenindione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C1=CC=CC=C1 NFBAXHOPROOJAW-UHFFFAOYSA-N 0.000 description 1
- LCNPPGIYNLTPFC-UHFFFAOYSA-N phenylphosphanium phosphate Chemical compound P(=O)([O-])([O-])[O-].C1(=CC=CC=C1)[PH3+].C1(=CC=CC=C1)[PH3+].C1(=CC=CC=C1)[PH3+] LCNPPGIYNLTPFC-UHFFFAOYSA-N 0.000 description 1
- MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910052699 polonium Inorganic materials 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
- MHZDONKZSXBOGL-UHFFFAOYSA-N propyl dihydrogen phosphate Chemical compound CCCOP(O)(O)=O MHZDONKZSXBOGL-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OATPTEJWZSGIME-UHFFFAOYSA-N tert-butyl ethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OC(C)(C)C OATPTEJWZSGIME-UHFFFAOYSA-N 0.000 description 1
- OMXBGKCMXUAHQB-UHFFFAOYSA-N tert-butyl methyl hydrogen phosphate Chemical compound COP(O)(=O)OC(C)(C)C OMXBGKCMXUAHQB-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- OBSZRRSYVTXPNB-UHFFFAOYSA-N tetraphosphorus Chemical compound P12P3P1P32 OBSZRRSYVTXPNB-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 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
- MBFBOWOPHAIFBS-UHFFFAOYSA-N tri(hexan-2-yl)phosphane Chemical compound CCCCC(C)P(C(C)CCCC)C(C)CCCC MBFBOWOPHAIFBS-UHFFFAOYSA-N 0.000 description 1
- PEMAVITZVCTFHJ-UHFFFAOYSA-N tri(hexan-3-yl)phosphane Chemical compound CCCC(CC)P(C(CC)CCC)C(CC)CCC PEMAVITZVCTFHJ-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
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 description 1
- KREGXBHGJXTOKZ-UHFFFAOYSA-N tridecylphosphonic acid Chemical compound CCCCCCCCCCCCCP(O)(O)=O KREGXBHGJXTOKZ-UHFFFAOYSA-N 0.000 description 1
- MHOHPNGCKKJHSD-UHFFFAOYSA-N triheptan-3-yl phosphate Chemical compound CCCCC(CC)OP(=O)(OC(CC)CCCC)OC(CC)CCCC MHOHPNGCKKJHSD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CDYVQSZPXAFIFA-UHFFFAOYSA-N trihydroxy(dipentyl)-lambda5-phosphane Chemical compound CCCCCP(O)(O)(O)CCCCC CDYVQSZPXAFIFA-UHFFFAOYSA-N 0.000 description 1
- BEFUBHVQRFELBK-UHFFFAOYSA-N trihydroxy(diphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(O)(O)(O)C1=CC=CC=C1 BEFUBHVQRFELBK-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- SDKSPURNWCSROF-UHFFFAOYSA-N trinonan-3-yl phosphate Chemical compound CCCCCCC(CC)OP(=O)(OC(CC)CCCCCC)OC(CC)CCCCCC SDKSPURNWCSROF-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
- 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
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- FWPDHLNSPBCAFO-UHFFFAOYSA-N trioctylbismuthane Chemical compound CCCCCCCC[Bi](CCCCCCCC)CCCCCCCC FWPDHLNSPBCAFO-UHFFFAOYSA-N 0.000 description 1
- BCIFMBSWFCXFAS-UHFFFAOYSA-N tripentan-2-yl phosphate Chemical compound CCCC(C)OP(=O)(OC(C)CCC)OC(C)CCC BCIFMBSWFCXFAS-UHFFFAOYSA-N 0.000 description 1
- ALCLDNINWGASPT-UHFFFAOYSA-N tripentan-3-yl phosphate Chemical compound CCC(CC)OP(=O)(OC(CC)CC)OC(CC)CC ALCLDNINWGASPT-UHFFFAOYSA-N 0.000 description 1
- ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- DTOOHWOPSUKNJL-UHFFFAOYSA-N tris(2-ethylphenyl) phosphate Chemical compound CCC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)CC)OC1=CC=CC=C1CC DTOOHWOPSUKNJL-UHFFFAOYSA-N 0.000 description 1
- RLRSSUBSVSBAJD-UHFFFAOYSA-N tris(2-ethylphenyl)phosphane Chemical compound CCC1=CC=CC=C1P(C=1C(=CC=CC=1)CC)C1=CC=CC=C1CC RLRSSUBSVSBAJD-UHFFFAOYSA-N 0.000 description 1
- XWJWJLGDEPPVJH-UHFFFAOYSA-N tris(2-methylnonan-2-yl) phosphate Chemical compound CCCCCCCC(C)(C)OP(=O)(OC(C)(C)CCCCCCC)OC(C)(C)CCCCCCC XWJWJLGDEPPVJH-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- NCXYBZTUGKHJFB-UHFFFAOYSA-N tris(3-ethylnonan-3-yl) phosphate Chemical compound CCCCCCC(CC)(CC)OP(=O)(OC(CC)(CC)CCCCCC)OC(CC)(CC)CCCCCC NCXYBZTUGKHJFB-UHFFFAOYSA-N 0.000 description 1
- QZWWNNQRBSJVLL-UHFFFAOYSA-N tris(3-ethylphenyl) phosphate Chemical compound CCC1=CC=CC(OP(=O)(OC=2C=C(CC)C=CC=2)OC=2C=C(CC)C=CC=2)=C1 QZWWNNQRBSJVLL-UHFFFAOYSA-N 0.000 description 1
- VTDQEJSEFIJDRP-UHFFFAOYSA-N tris(3-ethylphenyl)phosphane Chemical compound CCC1=CC=CC(P(C=2C=C(CC)C=CC=2)C=2C=C(CC)C=CC=2)=C1 VTDQEJSEFIJDRP-UHFFFAOYSA-N 0.000 description 1
- RMLPZKRPSQVRAB-UHFFFAOYSA-N tris(3-methylphenyl) phosphate Chemical compound CC1=CC=CC(OP(=O)(OC=2C=C(C)C=CC=2)OC=2C=C(C)C=CC=2)=C1 RMLPZKRPSQVRAB-UHFFFAOYSA-N 0.000 description 1
- BMPBPTNLNBRGOT-UHFFFAOYSA-N tris(4-ethylphenyl) phosphate Chemical compound C1=CC(CC)=CC=C1OP(=O)(OC=1C=CC(CC)=CC=1)OC1=CC=C(CC)C=C1 BMPBPTNLNBRGOT-UHFFFAOYSA-N 0.000 description 1
- PCCAGZSOGFNURV-UHFFFAOYSA-N tris(4-ethylphenyl)phosphane Chemical compound C1=CC(CC)=CC=C1P(C=1C=CC(CC)=CC=1)C1=CC=C(CC)C=C1 PCCAGZSOGFNURV-UHFFFAOYSA-N 0.000 description 1
- BOSMZFBHAYFUBJ-UHFFFAOYSA-N tris(4-methylphenyl) phosphate Chemical compound C1=CC(C)=CC=C1OP(=O)(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 BOSMZFBHAYFUBJ-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
- B01D69/1251—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction by interfacial polymerisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/56—Polyamides, e.g. polyester-amides
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Polyamides (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/550,527 US6337018B1 (en) | 2000-04-17 | 2000-04-17 | Composite membrane and method for making the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI243707B true TWI243707B (en) | 2005-11-21 |
Family
ID=24197538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090109021A TWI243707B (en) | 2000-04-17 | 2001-04-16 | Composite membrane and method for making the same |
Country Status (13)
| Country | Link |
|---|---|
| US (4) | US6337018B1 (enExample) |
| EP (1) | EP1276551B1 (enExample) |
| JP (1) | JP4932120B2 (enExample) |
| KR (1) | KR100839805B1 (enExample) |
| CN (1) | CN1210093C (enExample) |
| AU (2) | AU5524601A (enExample) |
| CA (1) | CA2403301C (enExample) |
| DE (1) | DE60139615D1 (enExample) |
| DK (1) | DK1276551T3 (enExample) |
| ES (1) | ES2328449T3 (enExample) |
| IL (2) | IL152286A0 (enExample) |
| TW (1) | TWI243707B (enExample) |
| WO (1) | WO2001078882A2 (enExample) |
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-
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
- 2001-04-09 JP JP2001576176A patent/JP4932120B2/ja not_active Expired - Lifetime
- 2001-04-09 EP EP01928384A patent/EP1276551B1/en not_active Expired - Lifetime
- 2001-04-09 US US09/829,024 patent/US6562266B2/en not_active Expired - Lifetime
- 2001-04-09 KR KR1020027013894A patent/KR100839805B1/ko not_active Expired - Lifetime
- 2001-04-09 DK DK01928384T patent/DK1276551T3/da active
- 2001-04-09 ES ES01928384T patent/ES2328449T3/es not_active Expired - Lifetime
- 2001-04-09 AU AU2001255246A patent/AU2001255246B2/en not_active Expired
- 2001-04-09 WO PCT/US2001/011265 patent/WO2001078882A2/en not_active Ceased
- 2001-04-09 IL IL15228601A patent/IL152286A0/xx active IP Right Grant
- 2001-04-09 CN CNB018080642A patent/CN1210093C/zh not_active Expired - Lifetime
- 2001-04-09 DE DE60139615T patent/DE60139615D1/de not_active Expired - Lifetime
- 2001-04-09 CA CA002403301A patent/CA2403301C/en not_active Expired - Fee Related
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| US20020113008A1 (en) | 2002-08-22 |
| US20010050252A1 (en) | 2001-12-13 |
| DK1276551T3 (da) | 2009-11-16 |
| CN1441693A (zh) | 2003-09-10 |
| CN1210093C (zh) | 2005-07-13 |
| EP1276551B1 (en) | 2009-08-19 |
| US6337018B1 (en) | 2002-01-08 |
| CA2403301C (en) | 2009-08-25 |
| KR100839805B1 (ko) | 2008-06-19 |
| ES2328449T3 (es) | 2009-11-13 |
| WO2001078882A3 (en) | 2002-02-28 |
| US6562266B2 (en) | 2003-05-13 |
| DE60139615D1 (de) | 2009-10-01 |
| US6878278B2 (en) | 2005-04-12 |
| KR20030001430A (ko) | 2003-01-06 |
| US6723241B2 (en) | 2004-04-20 |
| WO2001078882A2 (en) | 2001-10-25 |
| IL152286A (en) | 2006-10-05 |
| IL152286A0 (en) | 2003-05-29 |
| AU2001255246B2 (en) | 2005-02-10 |
| AU5524601A (en) | 2001-10-30 |
| JP2003531219A (ja) | 2003-10-21 |
| CA2403301A1 (en) | 2001-10-25 |
| EP1276551A2 (en) | 2003-01-22 |
| JP4932120B2 (ja) | 2012-05-16 |
| US20030116498A1 (en) | 2003-06-26 |
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