JP2004510847A5 - - Google Patents
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- JP2004510847A5 JP2004510847A5 JP2002532495A JP2002532495A JP2004510847A5 JP 2004510847 A5 JP2004510847 A5 JP 2004510847A5 JP 2002532495 A JP2002532495 A JP 2002532495A JP 2002532495 A JP2002532495 A JP 2002532495A JP 2004510847 A5 JP2004510847 A5 JP 2004510847A5
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- JP
- Japan
- Prior art keywords
- polymerization
- reaction
- initiator
- water
- mmol
- 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
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- 238000006116 polymerization reaction Methods 0.000 description 140
- 239000000178 monomer Substances 0.000 description 131
- 238000006243 chemical reaction Methods 0.000 description 120
- 239000003999 initiator Substances 0.000 description 116
- 229920000642 polymer Polymers 0.000 description 91
- 238000000034 method Methods 0.000 description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
- 229910052723 transition metal Inorganic materials 0.000 description 55
- 239000000243 solution Substances 0.000 description 54
- 150000003624 transition metals Chemical class 0.000 description 53
- 239000003446 ligand Substances 0.000 description 52
- 239000000203 mixture Substances 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 43
- 125000000524 functional group Chemical group 0.000 description 40
- 150000003254 radicals Chemical class 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 238000007323 disproportionation reaction Methods 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- 239000010949 copper Substances 0.000 description 29
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 28
- 125000004429 atom Chemical group 0.000 description 25
- 229920001400 block copolymer Polymers 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- 229920001223 polyethylene glycol Polymers 0.000 description 23
- 150000001540 azides Chemical class 0.000 description 22
- 238000012546 transfer Methods 0.000 description 22
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 17
- 238000002474 experimental method Methods 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 230000003647 oxidation Effects 0.000 description 16
- 238000007254 oxidation reaction Methods 0.000 description 16
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 15
- 229910052802 copper Inorganic materials 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 229910002476 CuII Inorganic materials 0.000 description 14
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- -1 transition metal salts Chemical class 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000010526 radical polymerization reaction Methods 0.000 description 12
- ZPAICLPTNKAJHB-UHFFFAOYSA-M sodium;4-ethenylbenzoate Chemical compound [Na+].[O-]C(=O)C1=CC=C(C=C)C=C1 ZPAICLPTNKAJHB-UHFFFAOYSA-M 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- BSULWPSUVMOMAN-UHFFFAOYSA-N 2-azidoethanol Chemical compound OCCN=[N+]=[N-] BSULWPSUVMOMAN-UHFFFAOYSA-N 0.000 description 10
- 102100026735 Coagulation factor VIII Human genes 0.000 description 10
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 10
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 10
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 10
- 230000000977 initiatory effect Effects 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000002091 cationic group Chemical group 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000000306 component Substances 0.000 description 8
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 8
- 239000003444 phase transfer catalyst Substances 0.000 description 8
- 238000006479 redox reaction Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 7
- 238000005755 formation reaction Methods 0.000 description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
- 230000000379 polymerizing effect Effects 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 150000003623 transition metal compounds Chemical class 0.000 description 7
- 229920003169 water-soluble polymer Polymers 0.000 description 7
- IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 150000001412 amines Chemical group 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- MBZXZCVEFCLXRV-UHFFFAOYSA-N ethyl 2-azido-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)N=[N+]=[N-] MBZXZCVEFCLXRV-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 229920002521 macromolecule Polymers 0.000 description 6
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- XXSPGBOGLXKMDU-UHFFFAOYSA-N 2-bromo-2-methylpropanoic acid Chemical compound CC(C)(Br)C(O)=O XXSPGBOGLXKMDU-UHFFFAOYSA-N 0.000 description 5
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 5
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000004699 copper complex Chemical class 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- KOFFFKMEMKRWMT-UHFFFAOYSA-N 1-azidoethylbenzene Chemical compound [N-]=[N+]=NC(C)C1=CC=CC=C1 KOFFFKMEMKRWMT-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 4
- 230000011987 methylation Effects 0.000 description 4
- 238000007069 methylation reaction Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 3
- 235000006506 Brasenia schreberi Nutrition 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 3
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910001431 copper ion Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- AMZGOPVHQLKMPR-UHFFFAOYSA-M methanesulfonate;trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium Chemical compound CS([O-])(=O)=O.CC(=C)C(=O)OCC[N+](C)(C)C AMZGOPVHQLKMPR-UHFFFAOYSA-M 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- XFTALRAZSCGSKN-UHFFFAOYSA-M sodium;4-ethenylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=C(C=C)C=C1 XFTALRAZSCGSKN-UHFFFAOYSA-M 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- HSXAMLBRNJRCFI-UHFFFAOYSA-M trifluoromethanesulfonate;trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC(=C)C(=O)OCC[N+](C)(C)C HSXAMLBRNJRCFI-UHFFFAOYSA-M 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- YKPFXAHKQLQHCJ-UHFFFAOYSA-N 1-azidopropan-2-ol Chemical compound CC(O)CN=[N+]=[N-] YKPFXAHKQLQHCJ-UHFFFAOYSA-N 0.000 description 2
- IINOTNZQTDMTGM-UHFFFAOYSA-N 2-azidoethyl 2-bromopropanoate Chemical compound CC(Br)C(=O)OCCN=[N+]=[N-] IINOTNZQTDMTGM-UHFFFAOYSA-N 0.000 description 2
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229920000028 Gradient copolymer Polymers 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- JWZBOJUPGSZUHH-UHFFFAOYSA-N azidoethane 2-methylpropanoic acid Chemical compound CCN=[N+]=[N-].CC(C)C(O)=O JWZBOJUPGSZUHH-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000009739 binding Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- OWMBTIRJFMGPAC-UHFFFAOYSA-N dimethylamino 2-methylprop-2-enoate Chemical compound CN(C)OC(=O)C(C)=C OWMBTIRJFMGPAC-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000006897 homolysis reaction Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 150000002496 iodine Chemical class 0.000 description 2
- 125000003010 ionic group Chemical group 0.000 description 2
- 238000012886 linear function Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 238000010550 living polymerization reaction Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 2
- 239000012022 methylating agents Substances 0.000 description 2
- 230000001035 methylating effect Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- SYZCZDCAEVUSPM-UHFFFAOYSA-M tetrahexylazanium;bromide Chemical compound [Br-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC SYZCZDCAEVUSPM-UHFFFAOYSA-M 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- USFMMZYROHDWPJ-UHFFFAOYSA-N trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium Chemical class CC(=C)C(=O)OCC[N+](C)(C)C USFMMZYROHDWPJ-UHFFFAOYSA-N 0.000 description 2
- XIXDXIUWZQJVHJ-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;iodide Chemical compound [I-].CC(=C)C(=O)OCC[N+](C)(C)C XIXDXIUWZQJVHJ-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
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| US5807937A (en) | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
| US7125938B2 (en) * | 1997-03-11 | 2006-10-24 | Carnegie Mellon University | Atom or group transfer radical polymerization |
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| WO2002028914A2 (en) | 2000-10-06 | 2002-04-11 | Carnegie Mellon University | A catalyst system for controlled polymerization |
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| EP1377519B1 (en) * | 2001-04-06 | 2010-06-09 | Carnegie-Mellon University | A process for the preparation of nanostructured materials |
| EP1397403B1 (fr) * | 2001-05-04 | 2008-03-12 | Rhodia Chimie | Copolymeres a blocs tensioactifs prepares par polymerisation radicalaire controlee |
| WO2003031481A2 (en) * | 2001-10-12 | 2003-04-17 | Carnegie Mellon University | Simultaneous reverse and normal initiation of atrp |
| US7064166B2 (en) * | 2001-10-12 | 2006-06-20 | Carnegie Mellon University | Process for monomer sequence control in polymerizations |
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| WO2004014963A2 (en) * | 2002-08-09 | 2004-02-19 | Carnegie Mellon University | Polymers, supersoft elastomers and methods for preparing the same |
| US7893174B2 (en) | 2004-03-05 | 2011-02-22 | Carnegie Mellon University | Atom transfer radical polymerization process |
| WO2005087818A1 (en) * | 2004-03-05 | 2005-09-22 | Carnegie Mellon University | Preparation of functional polymers |
| US7902321B2 (en) * | 2004-11-17 | 2011-03-08 | Cornell Research Foundation, Inc. | One-pot, one-step in situ living polymerization from silicate anchored multifunctional initiator |
| WO2006074202A2 (en) * | 2005-01-04 | 2006-07-13 | Intezyne Technologies, Incorporated | Synthesis of hybrid block copolymers and uses thereof |
| DE602006012336D1 (de) | 2005-08-23 | 2010-04-01 | Univ Carnegie Mellon | Radikalische atomtransfer-polymerisation in mikroemulsion und echte emulsionspolymerisation |
| EP1943278B1 (en) | 2005-08-26 | 2010-10-06 | Carnegie Mellon University | Polymerization process with catalyst reactivation |
| US20070123646A1 (en) * | 2005-09-13 | 2007-05-31 | Lele Bhalchandra S | Protein-polymer conjugates and synthesis thereof |
| WO2008048295A2 (en) * | 2005-11-18 | 2008-04-24 | Northwestern University | Stable dispersions of polymer-coated graphitic nanoplatelets |
| FI20051226L (fi) | 2005-12-01 | 2007-06-02 | Jvs Polymers Oy | Nanorakenteinen hylkivä kuitumateriaali |
| KR100738580B1 (ko) * | 2005-12-23 | 2007-07-11 | 제일모직주식회사 | 스티렌계 고분자-실리카 나노복합체의 제조방법 |
| DK1988910T3 (en) | 2006-02-28 | 2018-01-22 | Kodiak Sciences Inc | ACRYLOYLOXYETHYLPHOSPHORYLCHOLINE-CONTAINING POLYMER CONJUGATES AND PREPARATION thereof |
| US8349410B2 (en) | 2006-08-17 | 2013-01-08 | University of Pittsburgh—of the Commonwealth System of Higher Education | Modification of surfaces with polymers |
| US8367051B2 (en) | 2006-10-09 | 2013-02-05 | Carnegie Mellon University | Preparation of functional gel particles with a dual crosslink network |
| WO2008148000A1 (en) | 2007-05-23 | 2008-12-04 | Carnegie Mellon University | Atom transfer dispersion polymerization |
| US8865797B2 (en) | 2007-05-23 | 2014-10-21 | Carnegie Mellon University | Hybrid particle composite structures with reduced scattering |
| US20090074709A1 (en) * | 2007-09-14 | 2009-03-19 | Koepsel Richard R | Methods, devices and systems for biocidal surface activity |
| DE102008043666A1 (de) * | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von AB-Diblockcopolymeren mit einem bimodalen verteilten A-Block |
| US8541621B2 (en) | 2008-12-05 | 2013-09-24 | Electronics And Telecommunications Research Institute | Polymerization initiator having aryl azide and surface modification method of cyclic olefin copolymer using the same |
| US8822610B2 (en) | 2008-12-22 | 2014-09-02 | ATRP Solutions, Inc. | Control over controlled radical polymerization processes |
| US8815971B2 (en) | 2008-12-22 | 2014-08-26 | ATRP Solutions, Inc. | Control over controlled radical polymerization processes |
| GB2481561B (en) | 2009-03-27 | 2013-12-11 | Univ Carnegie Mellon | Preparation of functional star macromolecules |
| US9783628B2 (en) | 2009-04-23 | 2017-10-10 | ATRP Solutions, Inc. | Dual-mechanism thickening agents for hydraulic fracturing fluids |
| US8173750B2 (en) | 2009-04-23 | 2012-05-08 | ATRP Solutions, Inc. | Star macromolecules for personal and home care |
| US8569421B2 (en) | 2009-04-23 | 2013-10-29 | ATRP Solutions, Inc. | Star macromolecules for personal and home care |
| WO2011075185A1 (en) | 2009-12-18 | 2011-06-23 | Oligasis | Targeted drug phosphorylcholine polymer conjugates |
| US8816001B2 (en) | 2010-09-10 | 2014-08-26 | Franklin And Marshall College | Genetically encoded initiator for polymer growth from proteins |
| US9587064B2 (en) | 2010-12-08 | 2017-03-07 | ATRP Solutions, Inc. | Salt-tolerant star macromolecules |
| WO2012091965A1 (en) | 2010-12-17 | 2012-07-05 | Carnegie Mellon University | Electrochemically mediated atom transfer radical polymerization |
| JP5881317B2 (ja) * | 2011-06-14 | 2016-03-09 | Ｋｊケミカルズ株式会社 | 不飽和第４級アンモニウム塩化合物の製造方法及びそれからなる帯電防止剤と帯電防止組成物 |
| WO2013028756A1 (en) | 2011-08-22 | 2013-02-28 | Carnegie Mellon University | Atom transfer radical polymerization under biologically compatible conditions |
| US9790305B2 (en) | 2011-09-09 | 2017-10-17 | Franklin And Marshall College | Site specifically incorporated initiator for growth of polymers from proteins |
| WO2013158183A2 (en) | 2012-01-27 | 2013-10-24 | Carnegie Mellon University | Processable self-organizing nanoparticles |
| US9533297B2 (en) | 2012-02-23 | 2017-01-03 | Carnegie Mellon University | Ligands designed to provide highly active catalyst complexes |
| ITMI20120808A1 (it) * | 2012-05-11 | 2013-11-12 | Versalis Spa | "procedimento per la preparazione di polibutadiene ramificato ad alto contenuto in unita' 1,4-cis" |
| US8975346B2 (en) | 2012-05-18 | 2015-03-10 | Sabic Global Technologies B.V. | Polycarbonate copolymers via controlled radical polymerization |
| MX368683B (es) | 2012-08-30 | 2019-10-11 | Pilot Polymer Tech Inc | Agentes espesantes de mecanismo dual para fluidos de fracturación hidráulica. |
| US9914870B2 (en) | 2013-01-22 | 2018-03-13 | Carnegie Mellon University | Lignin-containing polymers and compositions including lignin-containing polymers |
| EP2951220B1 (en) | 2013-02-04 | 2020-11-25 | Pilot Polymer Technologies, Inc. | Salt-tolerant star macromolecules |
| WO2014172557A1 (en) | 2013-04-18 | 2014-10-23 | Carnegie Mellon University | Functionalized polymer hybrids |
| EP2999738B1 (en) | 2013-05-22 | 2019-02-20 | Triblue Corporation | Methods of forming a polymer layer on a polymer surface |
| PL3041513T3 (pl) | 2013-09-08 | 2021-01-25 | Kodiak Sciences Inc. | Obojnaczojonowe polimerowe koniugaty czynnika viii |
| US9840553B2 (en) | 2014-06-28 | 2017-12-12 | Kodiak Sciences Inc. | Dual PDGF/VEGF antagonists |
| CA2956431C (en) | 2014-07-03 | 2023-01-31 | ATRP Solutions, Inc. | Surfactant-compatible star macromolecules |
| KR102210104B1 (ko) | 2014-10-17 | 2021-02-01 | 코디악 사이언시스 인코포레이티드 | 부티릴콜린에스테라제 양성이온성 중합체 컨쥬게이트 |
| US9982070B2 (en) | 2015-01-12 | 2018-05-29 | Carnegie Mellon University | Aqueous ATRP in the presence of an activator regenerator |
| US10382746B1 (en) * | 2015-09-22 | 2019-08-13 | Rockwell Collins, Inc. | Stereoscopic augmented reality head-worn display with indicator conforming to a real-world object |
| CA3010056A1 (en) | 2015-12-30 | 2017-07-06 | Kodiak Sciences Inc. | Antibodies and conjugates thereof |
| CN105670343B (zh) * | 2016-01-08 | 2017-05-03 | 厦门大学 | 一种含硅氮阻燃型聚合物染料及其制备方法 |
| US10934383B2 (en) | 2016-01-25 | 2021-03-02 | Carnegie Mellon University | Composite compositions and modification of inorganic particles for use in composite compositions |
| US10982266B2 (en) | 2016-11-03 | 2021-04-20 | Carnegie Mellon University | Nucleic acid-polymer conjugates for bright fluorescent tags |
| WO2018132696A2 (en) | 2017-01-12 | 2018-07-19 | Russell Alan J | Stomach acid-stable and mucin-binding protein-polymer conjugates |
| WO2018132582A1 (en) | 2017-01-12 | 2018-07-19 | Carnegie Mellon University | Surfactant assisted formation of a catalyst complex for emulsion atom transfer radical polymerization processes |
| CN107540028B (zh) * | 2017-08-16 | 2020-07-10 | 中国石油天然气集团公司 | 一种聚磺钻井废弃物无害化处理剂及其制备方法与应用 |
| CN112203679A (zh) | 2018-03-02 | 2021-01-08 | 科达制药股份有限公司 | Il-6抗体及其融合构建体和缀合物 |
| US10853014B2 (en) | 2018-04-17 | 2020-12-01 | Rockwell Collins, Inc. | Head wearable device, system, and method |
| US11857634B2 (en) | 2018-04-20 | 2024-01-02 | University of Pittsburgh—of the Commonwealth System of Higher Education | Cationic amphiphilic polymers for codelivery of hydrophobic agents and nucleic acids |
| US11472894B2 (en) | 2018-07-23 | 2022-10-18 | Carnegie Mellon University | Enzyme-assisted ATRP procedures |
| WO2020028715A1 (en) | 2018-08-01 | 2020-02-06 | Russell Alan J | Amino-reactive positively charged atrp initiators that maintain their positive charge during synthesis of biomacro-initiators |
| WO2020077170A1 (en) | 2018-10-12 | 2020-04-16 | University Of Pittsburgh- Of The Commonwealth System Of Higher Education | Small polymeric carriers for delivery of agents |
| CN114786731A (zh) | 2019-10-10 | 2022-07-22 | 科达制药股份有限公司 | 治疗眼部病症的方法 |
| US20250188325A1 (en) * | 2022-04-22 | 2025-06-12 | Purdue Research Foundation | Positively charged adhesives |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62292806A (ja) * | 1986-06-10 | 1987-12-19 | イ−・アイ・デユポン・ド・ネモア−ス・アンド・コンパニ− | 原子団移動重合法およびリビングポリマ− |
| GB8803765D0 (en) * | 1988-02-18 | 1988-03-16 | Ici Plc | Polymerisation process |
| US5444135A (en) * | 1992-12-17 | 1995-08-22 | Exxon Chemical Patents Inc. | Direct synthesis by living cationic polymerization of nitrogen-containing polymers |
| US5763548A (en) | 1995-03-31 | 1998-06-09 | Carnegie-Mellon University | (Co)polymers and a novel polymerization process based on atom (or group) transfer radical polymerization |
| US5807937A (en) * | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
| US5789487A (en) * | 1996-07-10 | 1998-08-04 | Carnegie-Mellon University | Preparation of novel homo- and copolymers using atom transfer radical polymerization |
| US5886118C1 (en) * | 1997-04-14 | 2001-02-20 | Univ Case Western Reserve | Process for polymerizing acrylonitrile |
| FR2771407B1 (fr) * | 1997-11-25 | 2001-06-01 | Nalco Chemical Co | Materiau precurseur de ceramique non cuit et procede de preparation d'un materiau ceramique a partir de celui-ci |
| GB9725455D0 (en) | 1997-12-02 | 1998-01-28 | Univ Warwick | Supported polymerisation catalyst |
| US6121371A (en) | 1998-07-31 | 2000-09-19 | Carnegie Mellon University | Application of atom transfer radical polymerization to water-borne polymerization systems |
| US20010047065A1 (en) | 1999-06-03 | 2001-11-29 | Sun-Chueh Kao | Method for preparing a supported catalyst system and its use in a polymerization process |
| US6441066B1 (en) * | 1999-12-16 | 2002-08-27 | Ppg Industries Ohio, Inc. | Pigment dispersions containing dispersants prepared by controlled radical polymerization and having pendent hydrophobic polymeric segments |
-
2001
- 2001-10-05 AU AU2002216619A patent/AU2002216619A1/en not_active Abandoned
- 2001-10-05 EP EP06025550A patent/EP1801129A3/en not_active Withdrawn
- 2001-10-05 WO PCT/US2001/031323 patent/WO2002028913A2/en not_active Ceased
- 2001-10-05 JP JP2002532495A patent/JP5005155B2/ja not_active Expired - Fee Related
- 2001-10-05 DE DE60125409T patent/DE60125409T2/de not_active Expired - Lifetime
- 2001-10-05 US US09/972,260 patent/US6624262B2/en not_active Expired - Lifetime
- 2001-10-05 EP EP01986304A patent/EP1337563B1/en not_active Expired - Lifetime
-
2003
- 2003-07-23 US US10/625,890 patent/US20040044152A1/en not_active Abandoned
-
2008
- 2008-07-14 JP JP2008182957A patent/JP2009013414A/ja active Pending
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