IT201800005186A1 - Procedimento di polimerizzazione per la produzione di polimeri vinil aromatici a struttura controllata - Google Patents
Procedimento di polimerizzazione per la produzione di polimeri vinil aromatici a struttura controllata Download PDFInfo
- Publication number
- IT201800005186A1 IT201800005186A1 IT102018000005186A IT201800005186A IT201800005186A1 IT 201800005186 A1 IT201800005186 A1 IT 201800005186A1 IT 102018000005186 A IT102018000005186 A IT 102018000005186A IT 201800005186 A IT201800005186 A IT 201800005186A IT 201800005186 A1 IT201800005186 A1 IT 201800005186A1
- Authority
- IT
- Italy
- Prior art keywords
- process according
- styrene
- reaction
- vinyl
- ethyl
- Prior art date
Links
- 238000006116 polymerization reaction Methods 0.000 title claims description 26
- 229920002554 vinyl polymer Polymers 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 108
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 102
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 85
- 229920000642 polymer Polymers 0.000 claims description 81
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 70
- 238000006243 chemical reaction Methods 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 62
- 239000003999 initiator Substances 0.000 claims description 55
- 230000008569 process Effects 0.000 claims description 55
- 235000010323 ascorbic acid Nutrition 0.000 claims description 52
- 239000011668 ascorbic acid Substances 0.000 claims description 51
- 229960005070 ascorbic acid Drugs 0.000 claims description 51
- 239000000178 monomer Substances 0.000 claims description 47
- 235000019441 ethanol Nutrition 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical group 0.000 claims description 36
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims description 33
- 235000019439 ethyl acetate Nutrition 0.000 claims description 30
- 230000015572 biosynthetic process Effects 0.000 claims description 26
- 239000003638 chemical reducing agent Substances 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 150000001412 amines Chemical class 0.000 claims description 22
- 239000003446 ligand Substances 0.000 claims description 20
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 19
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 17
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 15
- 238000003786 synthesis reaction Methods 0.000 claims description 15
- -1 benzal halides Chemical class 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 13
- 239000010949 copper Substances 0.000 claims description 13
- 150000001340 alkali metals Chemical class 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000011261 inert gas Substances 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims description 8
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229960004592 isopropanol Drugs 0.000 claims description 7
- VAPJFYJBCCPOAV-UHFFFAOYSA-N methyl 2,2-dichlorobutanoate Chemical compound CCC(Cl)(Cl)C(=O)OC VAPJFYJBCCPOAV-UHFFFAOYSA-N 0.000 claims description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 239000012190 activator Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 claims description 5
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 5
- 229940011051 isopropyl acetate Drugs 0.000 claims description 5
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 5
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims description 5
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 4
- TWJKBMRWJYYYFO-UHFFFAOYSA-N ethyl 2,2-dichloropropanoate Chemical compound CCOC(=O)C(C)(Cl)Cl TWJKBMRWJYYYFO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- BOZRCGLDOHDZBP-UHFFFAOYSA-N 2-ethylhexanoic acid;tin Chemical compound [Sn].CCCCC(CC)C(O)=O BOZRCGLDOHDZBP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- ARQNAXVQDYBTEE-UHFFFAOYSA-N ethyl 2-chloro-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Cl ARQNAXVQDYBTEE-UHFFFAOYSA-N 0.000 claims description 3
- 229940093915 gynecological organic acid Drugs 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical class ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 claims description 2
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical class COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 claims description 2
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical class CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical class CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052792 caesium Inorganic materials 0.000 claims description 2
- 150000005323 carbonate salts Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 2
- 229940093499 ethyl acetate Drugs 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- KHMYONNPZWOTKW-UHFFFAOYSA-N pent-1-enylbenzene Chemical class CCCC=CC1=CC=CC=C1 KHMYONNPZWOTKW-UHFFFAOYSA-N 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- 150000003606 tin compounds Chemical class 0.000 claims description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 2
- 235000010384 tocopherol Nutrition 0.000 claims description 2
- 229960001295 tocopherol Drugs 0.000 claims description 2
- 229930003799 tocopherol Natural products 0.000 claims description 2
- 239000011732 tocopherol Substances 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 51
- 229910000029 sodium carbonate Inorganic materials 0.000 description 25
- 235000017550 sodium carbonate Nutrition 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- URYAFVKLYSEINW-UHFFFAOYSA-N Chlorfenethol Chemical compound C=1C=C(Cl)C=CC=1C(O)(C)C1=CC=C(Cl)C=C1 URYAFVKLYSEINW-UHFFFAOYSA-N 0.000 description 21
- 239000003153 chemical reaction reagent Substances 0.000 description 15
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 229920006037 cross link polymer Polymers 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 238000000569 multi-angle light scattering Methods 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 6
- 239000011877 solvent mixture Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical group [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000003586 protic polar solvent Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- VGUWFGWZSVLROP-UHFFFAOYSA-N 1-pyridin-2-yl-n,n-bis(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC=NC=1CN(CC=1N=CC=CC=1)CC1=CC=CC=N1 VGUWFGWZSVLROP-UHFFFAOYSA-N 0.000 description 2
- XHCNINMOALIGKM-UHFFFAOYSA-N 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetrazacyclotetradecane Chemical compound CC1CC(C)(C)NCCNC(C)CC(C)(C)NCCN1 XHCNINMOALIGKM-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000001902 propagating effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- OBLYWUBMZGHQDN-UHFFFAOYSA-N 2,2-dichlorobutanoic acid Chemical compound CCC(Cl)(Cl)C(O)=O OBLYWUBMZGHQDN-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000000994 L-ascorbates Chemical class 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 101000701521 Mus musculus Phospholipid-transporting ATPase IK Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 244000089486 Phragmites australis subsp australis Species 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical class Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000004320 controlled atmosphere Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052730 francium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 102200145452 rs121908580 Human genes 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F112/02—Monomers containing only one unsaturated aliphatic radical
- C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F112/06—Hydrocarbons
- C08F112/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT102018000005186A IT201800005186A1 (it) | 2018-05-09 | 2018-05-09 | Procedimento di polimerizzazione per la produzione di polimeri vinil aromatici a struttura controllata |
| BR112020022613-0A BR112020022613B1 (pt) | 2018-05-09 | 2019-05-08 | Processo de polimerização para a síntese de polímeros aromáticos de vinila com uma estrutura controlada |
| MX2020011895A MX2020011895A (es) | 2018-05-09 | 2019-05-08 | Procedimiento de polimerizacion para la sintesis de polimeros aromaticos de vinilo con estructura controlada. |
| US17/052,880 US11725070B2 (en) | 2018-05-09 | 2019-05-08 | Polymerization process for the synthesis of vinyl aromatic polymers with a controlled structure |
| PCT/IB2019/053763 WO2019215626A1 (en) | 2018-05-09 | 2019-05-08 | Polymerization process for the synthesis of vinyl aromatic polymers with a controlled structure |
| CN201980031287.5A CN112154161B (zh) | 2018-05-09 | 2019-05-08 | 用于合成具有可控结构的乙烯基芳香族聚合物的聚合方法 |
| ES19727912T ES2912891T3 (es) | 2018-05-09 | 2019-05-08 | Proceso de polimerización para la síntesis de polímeros aromáticos vinílicos con una estructura controlada |
| JP2020562186A JP7570923B2 (ja) | 2018-05-09 | 2019-05-08 | 制御された構造を有するビニル芳香族ポリマーの合成のための重合方法 |
| HUE19727912A HUE057878T2 (hu) | 2018-05-09 | 2019-05-08 | Polimerizációs eljárás ellenõrzött szerkezetû vinilaromás polimerek szintézisére |
| EP19727912.8A EP3790910B1 (en) | 2018-05-09 | 2019-05-08 | Polymerization process for the synthesis of vinyl aromatic polymers with a controlled structure |
| PL19727912T PL3790910T3 (pl) | 2018-05-09 | 2019-05-08 | Sposób polimeryzacji w syntezie winylowych polimerów aromatycznych o kontrolowanej strukturze |
| KR1020207035293A KR102819629B1 (ko) | 2018-05-09 | 2019-05-08 | 제어된 구조를 가진 비닐 방향족 폴리머를 합성하기 위한 중합 방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT102018000005186A IT201800005186A1 (it) | 2018-05-09 | 2018-05-09 | Procedimento di polimerizzazione per la produzione di polimeri vinil aromatici a struttura controllata |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IT201800005186A1 true IT201800005186A1 (it) | 2019-11-09 |
Family
ID=63244731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT102018000005186A IT201800005186A1 (it) | 2018-05-09 | 2018-05-09 | Procedimento di polimerizzazione per la produzione di polimeri vinil aromatici a struttura controllata |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US11725070B2 (https=) |
| EP (1) | EP3790910B1 (https=) |
| JP (1) | JP7570923B2 (https=) |
| KR (1) | KR102819629B1 (https=) |
| CN (1) | CN112154161B (https=) |
| BR (1) | BR112020022613B1 (https=) |
| ES (1) | ES2912891T3 (https=) |
| HU (1) | HUE057878T2 (https=) |
| IT (1) | IT201800005186A1 (https=) |
| MX (1) | MX2020011895A (https=) |
| PL (1) | PL3790910T3 (https=) |
| WO (1) | WO2019215626A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113956468B (zh) * | 2021-12-14 | 2024-04-16 | 陕西科技大学 | 一种聚肽/聚烯烃杂化共聚物的合成方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998040415A1 (en) * | 1997-03-11 | 1998-09-17 | Carnegie Mellon University | Improvements in atom or group transfer radical polymerization |
| CN101555306A (zh) * | 2009-05-05 | 2009-10-14 | 苏州大学 | 一种合成水凝胶的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2757865B1 (fr) * | 1996-12-26 | 1999-04-02 | Atochem Elf Sa | Procede de polymerisation ou copolymerisation radicalaire controlee de monomeres (meth)acryliques, vinyliques, vinylideniques et dieniques et (co)polymeres obtenus |
| CN1060184C (zh) * | 1998-05-06 | 2001-01-03 | 华东理工大学 | 活性阴离子向活性自由基变换合成嵌段共聚物的方法 |
| CN1456577A (zh) * | 2003-05-26 | 2003-11-19 | 华南理工大学 | 有机硅氧烷改性苯乙烯－丙烯酸酯纳米乳液及其制备方法 |
| US7893174B2 (en) | 2004-03-05 | 2011-02-22 | Carnegie Mellon University | Atom transfer radical polymerization process |
| JP2010095591A (ja) * | 2008-10-15 | 2010-04-30 | Seiko Pmc Corp | 水性インク用顔料分散剤及び水性インク組成物 |
| WO2012020545A1 (ja) | 2010-08-10 | 2012-02-16 | 株式会社カネカ | （メタ）アクリル系重合体の製造方法 |
| US9533297B2 (en) * | 2012-02-23 | 2017-01-03 | Carnegie Mellon University | Ligands designed to provide highly active catalyst complexes |
| WO2014175221A1 (ja) | 2013-04-25 | 2014-10-30 | 株式会社カネカ | ビニル系重合体の製造方法 |
| CN104961133B (zh) * | 2015-06-24 | 2017-01-04 | 齐鲁工业大学 | 一种制备具有核壳间距的二氧化硅核壳材料的方法 |
| CN108884004B (zh) | 2016-02-13 | 2020-02-25 | 多尔夫凯塔尔化学制品（I）私人有限公司 | 用于控制和抑制乙烯基芳族单体聚合的组合物，及其使用方法 |
-
2018
- 2018-05-09 IT IT102018000005186A patent/IT201800005186A1/it unknown
-
2019
- 2019-05-08 WO PCT/IB2019/053763 patent/WO2019215626A1/en not_active Ceased
- 2019-05-08 BR BR112020022613-0A patent/BR112020022613B1/pt active IP Right Grant
- 2019-05-08 PL PL19727912T patent/PL3790910T3/pl unknown
- 2019-05-08 KR KR1020207035293A patent/KR102819629B1/ko active Active
- 2019-05-08 CN CN201980031287.5A patent/CN112154161B/zh active Active
- 2019-05-08 ES ES19727912T patent/ES2912891T3/es active Active
- 2019-05-08 MX MX2020011895A patent/MX2020011895A/es unknown
- 2019-05-08 HU HUE19727912A patent/HUE057878T2/hu unknown
- 2019-05-08 EP EP19727912.8A patent/EP3790910B1/en active Active
- 2019-05-08 US US17/052,880 patent/US11725070B2/en active Active
- 2019-05-08 JP JP2020562186A patent/JP7570923B2/ja active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998040415A1 (en) * | 1997-03-11 | 1998-09-17 | Carnegie Mellon University | Improvements in atom or group transfer radical polymerization |
| CN101555306A (zh) * | 2009-05-05 | 2009-10-14 | 苏州大学 | 一种合成水凝胶的方法 |
Non-Patent Citations (1)
| Title |
|---|
| WEI TANG ET AL: "Understanding Atom Transfer Radical Polymerization: Effect of Ligand and Initiator Structures on the Equilibrium Constants", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 130, no. 32, 1 August 2008 (2008-08-01), pages 10702 - 10713, XP055176475, ISSN: 0002-7863, DOI: 10.1021/ja802290a * |
Also Published As
| Publication number | Publication date |
|---|---|
| US11725070B2 (en) | 2023-08-15 |
| WO2019215626A1 (en) | 2019-11-14 |
| JP2021523267A (ja) | 2021-09-02 |
| JP7570923B2 (ja) | 2024-10-22 |
| EP3790910A1 (en) | 2021-03-17 |
| EP3790910B1 (en) | 2022-03-02 |
| HUE057878T2 (hu) | 2022-06-28 |
| KR102819629B1 (ko) | 2025-06-11 |
| CN112154161B (zh) | 2023-08-01 |
| BR112020022613B1 (pt) | 2023-10-03 |
| CN112154161A (zh) | 2020-12-29 |
| KR20210008398A (ko) | 2021-01-21 |
| US20210371555A1 (en) | 2021-12-02 |
| PL3790910T3 (pl) | 2022-05-16 |
| MX2020011895A (es) | 2021-01-29 |
| ES2912891T3 (es) | 2022-05-30 |
| BR112020022613A2 (pt) | 2021-02-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Feng et al. | Preparation and properties of optically active poly (N-methacryloyl L-leucine methyl ester) | |
| CN104151483A (zh) | 一种端羟基超支化聚丙烯酸酯的制备方法 | |
| WO2015122404A1 (ja) | リビングラジカル重合触媒及びそれを用いた重合体の製造方法 | |
| CN106633087A (zh) | 一种八臂杂臂星形聚合物及其制备方法 | |
| CN102753588B (zh) | 阳离子聚合性树脂、阳离子聚合性树脂组合物、及其固化物 | |
| JPH03195711A (ja) | 耐熱性の改良されたマレインイミド由来の単位を含有するポリマー | |
| KR101489564B1 (ko) | 신규 공중합체 | |
| IT201800005186A1 (it) | Procedimento di polimerizzazione per la produzione di polimeri vinil aromatici a struttura controllata | |
| TWI388580B (zh) | 活性自由基聚合反應助觸媒 | |
| CN104945255B (zh) | 一种甲基丙烯酸环己酯的制备方法 | |
| CN106065044A (zh) | 一种木器漆苯丙乳液的制备方法 | |
| Li et al. | Synthesis of High‐Molecular‐Weight Brush Polymers via RAFT Polymerization within the Micellar Nanoreactor of a PEG‐Based Macromonomer | |
| Wang et al. | Avoiding Disulfides: Improvement of Initiation and End‐Capping Reactions in the Synthesis of Polysulfide Block Copolymers | |
| Nasrullah et al. | Block copolymer synthesis via a combination of ATRP and RAFT using click chemistry | |
| WO2020255727A1 (ja) | ブロック共重合体用中間体、ブロック共重合体及びそれらの製造方法 | |
| RU2795681C2 (ru) | Способ полимеризации для синтеза винилароматических полимеров с контролируемой структурой | |
| WO2013170536A1 (zh) | 低残单中高分子量均聚n-乙烯基丁内酰胺k60水溶液的合成方法 | |
| JP2009067902A (ja) | テトラヒドロピランを溶媒とするカチオン重合方法 | |
| Zhang et al. | Synthesis, characterization and properties of a novel fluorinated methacrylate polymer | |
| CN100412101C (zh) | 一种两亲性含氟嵌段共聚物及其制备方法 | |
| WO2013170534A1 (zh) | 低残单n-乙烯基丁内酰胺均聚物k90水溶液的制备方法 | |
| CN101906185B (zh) | 两种温度敏感可逆溶解成相聚合物、其制备方法及形成的再生型两水相体系 | |
| Peng et al. | Novel amphiphilic graft copolymers bearing hydrophilic poly (acrylic acid) backbones and hydrophobic poly (butyl methacrylate) side chains | |
| CN103724572A (zh) | 一种具有低表面能及温度响应特性的梯度分子刷聚合物及其制备方法 | |
| JP2010111766A (ja) | ブロック共重合体 |