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Morpholine‐based RAFT agents for the reversible deactivation radical polymerization of vinyl acetate and N ‐vinylimidazole
Author(s) -
Vijayakrishna Kari,
Manojkumar Kasina,
Haribabu PM,
GyanaRanjan Behera,
Tilottama Baisakhi,
Agirre Amaia,
Meabe Leire,
Mantione Daniele,
Porcarelli Luca,
R Leiza Jose,
Mecerreyes David
Publication year - 2020
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.6032
Subject(s) - chain transfer , chemistry , reversible addition−fragmentation chain transfer polymerization , morpholine , polymerization , raft , polymer chemistry , vinyl acetate , radical polymerization , living free radical polymerization , polymer , organic chemistry , copolymer
Reversible addition–fragmentation chain transfer (RAFT) polymerization of less‐activated monomers in a controlled fashion is challenging due to the high reactivity and instability of the propagating radicals. We have designed dithiocarbamate‐based RAFT agents with morpholine as activating ‘Z’ group and benzyl, ethyl(1‐ethanoate)yl, ethyl(2‐propanoate)yl and cyanomethyl as ‘R’ leaving groups and investigated them for the reversible deactivation radical polymerization of vinyl acetate (VAc) and N ‐vinylimidazole ( N ‐VIm). RAFT polymerization of VAc and N ‐VIm at 70 °C using azobisisobutyronitrile as a free radical initiator proceeded in a controlled fashion as demonstrated by a linear increase in molar mass with conversion. Interestingly, the polymerization of VAc followed fast kinetics (approx. 60 min) with good to moderate control affording high‐molar‐mass poly(VAc) polymers. Furthermore, the synthesized chain transfer agents were able to polymerize N ‐VIm under controlled conditions. The morpholine RAFT agents bearing cyanomethyl and ethyl(2‐propanoate)yl leaving groups showed better control of the polymerization of VAc and N ‐VIm compared to the others. © 2020 Society of Chemical Industry