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Organic acids as efficient catalysts for group transfer polymerization of N,N-disubstituted acrylamide with silyl ketene acetal : polymerization mechanism and synthesis of diblock copolymers

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Title: Organic acids as efficient catalysts for group transfer polymerization of N,N-disubstituted acrylamide with silyl ketene acetal : polymerization mechanism and synthesis of diblock copolymers
Authors: Kikuchi, Seiya Browse this author
Chen, Yougen Browse this author
Kitano, Kodai Browse this author
Takada, Kenji Browse this author
Satoh, Toshifumi Browse this author
Kakuchi, Toyoji Browse this author →KAKEN DB
Issue Date: 2015
Publisher: Royal Society of Chemistry
Journal Title: Polymer chemistry
Volume: 6
Issue: 38
Start Page: 6845
End Page: 6856
Publisher DOI: 10.1039/c5py01104c
Abstract: The group transfer polymerization (GTP) of N,N-diethylacrylamide (DEAA) was studied using various combinations of an organic acid of N-(trimethylsilyl) bis-(trifluoromethanesulfonyl) imide (Me3SiNTf2), 1-(2,3,4,5,6-pentafluorophenyl)-1,1-bis(trifluoromethanesulfonyl) methane (C6F5CHTf2), and tris(pentafluorophenyl) borane (B(C6F5)(3)) and a silyl ketene acetal (SKA) of 1-methoxy-1-(trimethylsiloxy)-2-methyl-1-propene (MeSKA), 1-methoxy-1-(triethylsiloxy)-2-methyl-1-propene (EtSKA), 1-methoxy1-(triisopropylsiloxy)-2-methyl-1-propene (iPrSKA), and 1-methoxy-1-(triphenylsiloxy)-2-methyl-1-propene (PhSKA), among which the combination of B(C6F5)(3) and EtSKA afforded a relatively better control over the molecular weight distribution. The polymerization behavior of DEAA using B(C6F5)(3) and EtSKA was then intensively investigated in terms of the polymerization kinetics, chain extension experiments, and MALDI-TOF MS analyses, by which the polymerization was proven to proceed in a living fashion though an induction period of tens of minutes occurred. The B(C6F5)(3)-catalyzed GTP was further extended to various N, N-disubstituted acrylamides (DAAs), such as N, N-dimethylacrylamide (DMAA), N, N-di-n-propylacrylamide (DnPAA), N-acryloylpiperidine (API), N-acryloylmorpholine (NAM), N-(2-methoxyethyl)-N-methylacrylamide (MMEAA), N, N-bis(2-methoxyethyl) acrylamide (BMEAA), N, N-diallylacrylamide (DAlAA), and N-methyl-N-propargylacrylamide (MPAA). Finally, the livingness of the polymerization was used to synthesize acrylamide-acrylamide block copolymers and methacrylate-acrylamide hetero-block copolymers.
Type: article (author version)
URI: http://hdl.handle.net/2115/62628
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

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