JP2006521442A5 - - Google Patents
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- Publication number
- JP2006521442A5 JP2006521442A5 JP2006506008A JP2006506008A JP2006521442A5 JP 2006521442 A5 JP2006521442 A5 JP 2006521442A5 JP 2006506008 A JP2006506008 A JP 2006506008A JP 2006506008 A JP2006506008 A JP 2006506008A JP 2006521442 A5 JP2006521442 A5 JP 2006521442A5
- Authority
- JP
- Japan
- Prior art keywords
- halide
- lewis acid
- chloride
- reactive substrate
- halogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000758 substrate Substances 0.000 claims description 13
- QFEOTYVTTQCYAZ-UHFFFAOYSA-N dimanganese decacarbonyl Chemical group [Mn].[Mn].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] QFEOTYVTTQCYAZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims 26
- -1 manganese carbonyl radical Chemical class 0.000 claims 15
- 239000000178 monomer Substances 0.000 claims 14
- 239000002841 Lewis acid Substances 0.000 claims 12
- 150000007517 lewis acids Chemical class 0.000 claims 12
- 239000003999 initiator Substances 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 239000003054 catalyst Substances 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 229920001577 copolymer Polymers 0.000 claims 5
- 229920000642 polymer Polymers 0.000 claims 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 239000011572 manganese Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 230000000379 polymerizing effect Effects 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 150000001225 Ytterbium Chemical class 0.000 claims 2
- 229910052769 Ytterbium Inorganic materials 0.000 claims 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims 2
- 150000002603 lanthanum Chemical class 0.000 claims 2
- JLRJWBUSTKIQQH-UHFFFAOYSA-K lanthanum(3+);triacetate Chemical compound [La+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JLRJWBUSTKIQQH-UHFFFAOYSA-K 0.000 claims 2
- 239000011777 magnesium Substances 0.000 claims 2
- 229910052749 magnesium Inorganic materials 0.000 claims 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims 2
- 229910001623 magnesium bromide Inorganic materials 0.000 claims 2
- 229910001629 magnesium chloride Inorganic materials 0.000 claims 2
- 159000000003 magnesium salts Chemical class 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical group ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims 2
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 claims 2
- CKLHRQNQYIJFFX-UHFFFAOYSA-K ytterbium(III) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Yb+3] CKLHRQNQYIJFFX-UHFFFAOYSA-K 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 229940102001 zinc bromide Drugs 0.000 claims 2
- 239000011592 zinc chloride Substances 0.000 claims 2
- 235000005074 zinc chloride Nutrition 0.000 claims 2
- ZMLPZCGHASSGEA-UHFFFAOYSA-M zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F ZMLPZCGHASSGEA-UHFFFAOYSA-M 0.000 claims 2
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Substances [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 claims 2
- ZDUOUNIIAGIPSD-UHFFFAOYSA-N 1,1,1-tribromoethane Chemical compound CC(Br)(Br)Br ZDUOUNIIAGIPSD-UHFFFAOYSA-N 0.000 claims 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 claims 1
- KGKAYWMGPDWLQZ-UHFFFAOYSA-N 1,2-bis(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1CBr KGKAYWMGPDWLQZ-UHFFFAOYSA-N 0.000 claims 1
- KQNBRMUBPRGXSL-UHFFFAOYSA-N 1-(bromomethyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CBr)C=C1 KQNBRMUBPRGXSL-UHFFFAOYSA-N 0.000 claims 1
- NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 claims 1
- IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 claims 1
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 claims 1
- OGZJULUCZAZKHP-UHFFFAOYSA-N 2,2-dibromoethanol Chemical compound OCC(Br)Br OGZJULUCZAZKHP-UHFFFAOYSA-N 0.000 claims 1
- IDJOCJAIQSKSOP-UHFFFAOYSA-N 2,2-dichloroethanol Chemical compound OCC(Cl)Cl IDJOCJAIQSKSOP-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 claims 1
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 claims 1
- KSLINXQJWRKPET-UHFFFAOYSA-N 3-ethenyloxepan-2-one Chemical compound C=CC1CCCCOC1=O KSLINXQJWRKPET-UHFFFAOYSA-N 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Chemical group 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims 1
- 229950005228 bromoform Drugs 0.000 claims 1
- 150000001720 carbohydrates Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 229960001701 chloroform Drugs 0.000 claims 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Chemical group 0.000 claims 1
- 238000001782 photodegradation Methods 0.000 claims 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 150000003461 sulfonyl halides Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 238000005979 thermal decomposition reaction Methods 0.000 claims 1
- GKXZMEXQUWZGJK-UHFFFAOYSA-N tribromo(chloro)methane Chemical compound ClC(Br)(Br)Br GKXZMEXQUWZGJK-UHFFFAOYSA-N 0.000 claims 1
- YFDSDPIBEUFTMI-UHFFFAOYSA-N tribromoethanol Chemical compound OCC(Br)(Br)Br YFDSDPIBEUFTMI-UHFFFAOYSA-N 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 150000003751 zinc Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FALCMQXTWHPRIH-UHFFFAOYSA-N 2,3-dichloroprop-1-ene Chemical compound ClCC(Cl)=C FALCMQXTWHPRIH-UHFFFAOYSA-N 0.000 description 1
- 101150119033 CSE2 gene Proteins 0.000 description 1
- 101100007792 Escherichia coli (strain K12) casB gene Proteins 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0306820.2A GB0306820D0 (en) | 2003-03-25 | 2003-03-25 | Polymerisation of ethylenically unsaturated monomers |
| GB0306820.2 | 2003-03-25 | ||
| PCT/GB2004/001260 WO2004085494A1 (en) | 2003-03-25 | 2004-03-24 | Polymerisation of ethylenically unsaturated monomers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006521442A JP2006521442A (ja) | 2006-09-21 |
| JP2006521442A5 true JP2006521442A5 (https=) | 2007-06-14 |
| JP4855925B2 JP4855925B2 (ja) | 2012-01-18 |
Family
ID=9955481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006506008A Expired - Fee Related JP4855925B2 (ja) | 2003-03-25 | 2004-03-24 | エチレン不飽和モノマーの重合 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7759443B2 (https=) |
| EP (1) | EP1606323A1 (https=) |
| JP (1) | JP4855925B2 (https=) |
| GB (1) | GB0306820D0 (https=) |
| WO (1) | WO2004085494A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2479182B8 (en) * | 2009-09-16 | 2016-07-13 | Wave Life Sciences Japan, Inc. | Novel protecting group for synthesizing rna and derivative thereof |
| KR20140127299A (ko) * | 2012-02-03 | 2014-11-03 | 커먼웰쓰 사이언티픽 앤드 인더스트리얼 리서치 오가니제이션 | 가지형 폴리머 |
| KR102201713B1 (ko) | 2012-07-19 | 2021-01-12 | 돌비 인터네셔널 에이비 | 다채널 오디오 신호들의 렌더링을 향상시키기 위한 방법 및 디바이스 |
| CN106164109A (zh) * | 2014-04-07 | 2016-11-23 | 陶氏环球技术有限责任公司 | 通过光的丙烯酸酯的可控自由基聚合的调节 |
| CN108070063B (zh) * | 2017-12-29 | 2020-03-24 | 中国科学院广州能源研究所 | 一种乙烯基酰胺类嵌段共聚物水合物动力学抑制剂及其制备方法与应用 |
| CN112004674A (zh) * | 2018-02-22 | 2020-11-27 | 北卡罗莱纳州立大学 | 纤维素酯膜及其制造与使用方法 |
| CN116408119B (zh) * | 2021-12-29 | 2024-11-01 | 中国石油天然气股份有限公司 | 一种用于co2和环氧化物合成环碳酸酯的非金属催化剂、制备方法及应用 |
| CN115260350B (zh) * | 2022-08-25 | 2024-02-23 | 中国科学院长春应用化学研究所 | 一种超分子阴离子结合催化单体进行活性阳离子聚合的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1149961A (en) * | 1965-07-06 | 1969-04-23 | Ici Ltd | Polymerisation process using metal carbonyl catalysts |
| US3982942A (en) * | 1973-03-16 | 1976-09-28 | Ici United States Inc. | Photopolymerization of ethylenically-unsaturated organic compounds |
| US4053316A (en) * | 1973-03-16 | 1977-10-11 | Ici United States Inc. | Photopolymerization of ethylenically-unsaturated organic compounds |
| JPH072838B2 (ja) * | 1985-03-22 | 1995-01-18 | 鐘淵化学工業株式会社 | 分子末端に不飽和基を含有するポリアルキレンオキシドの製造方法 |
| JPS62215622A (ja) * | 1986-03-15 | 1987-09-22 | Showa Highpolymer Co Ltd | 硬化可能な樹脂の製造方法 |
| US5789487A (en) * | 1996-07-10 | 1998-08-04 | Carnegie-Mellon University | Preparation of novel homo- and copolymers using atom transfer radical polymerization |
| JP4057190B2 (ja) * | 1998-04-28 | 2008-03-05 | 株式会社カネカ | ブロック共重合体 |
| EP0992519B1 (en) * | 1998-04-28 | 2004-10-20 | Kaneka Corporation | Block copolymer |
| JP4418082B2 (ja) * | 2000-05-11 | 2010-02-17 | 株式会社カネカ | ビニル系重合体の精製方法 |
-
2003
- 2003-03-25 GB GBGB0306820.2A patent/GB0306820D0/en not_active Ceased
-
2004
- 2004-03-24 US US10/549,856 patent/US7759443B2/en not_active Expired - Fee Related
- 2004-03-24 JP JP2006506008A patent/JP4855925B2/ja not_active Expired - Fee Related
- 2004-03-24 EP EP04722885A patent/EP1606323A1/en not_active Withdrawn
- 2004-03-24 WO PCT/GB2004/001260 patent/WO2004085494A1/en not_active Ceased
-
2010
- 2010-06-09 US US12/801,447 patent/US20100249321A1/en not_active Abandoned
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