Synthesis and Characterization of Novel Quaternary Ammonium RAFT Agents

Abstract

Synthesis of three new cationic thio compounds suitable to control free‐radical polymerization according to the reversible addition fragmentation chain transfer (RAFT) process (reversible addition fragmentation transfer) is presented. Among them, two bear a quaternary ammonium group in the R group [i.e., N,N‐dimethyl‐N‐(4‐(((phenylcarbonothionyl)thio)methyl)benzyl)ethanammonium bromide and N‐(4‐((((dodecylthio) carbonothioyl)thio)methyl)benzyl)‐N,N‐dimethylethanammonium bromide, a dithioester and a trithiocarbonate, respectively]. The synthesis of a trithiocarbonate bearing an ammonium group in the Z group [i.e., 2‐((11‐((benzylthio)carbonothioyl)thio)undecanoyl)oxy)‐N,N,N‐trimethylammonium iodide] is also presented. Another three thio compounds, namely 1,4‐phenylenebis(methylene)dibenzenecarbodithioate, didodecyl‐1,4‐phenylenebis(methylene)bistrithiocarbonate, and 11‐(((benzylthio)carbonothioyl)thio)undecanoic acid, identified as other potentially interesting mono‐or difunctional RAFT agents, which were obtained as side products or intermediates, were isolated and fully characterized.

Keywords:

• cationic transurf
• dithioester
• RAFT
• trithiocarbonate

Acknowledgments

The authors thank the National Research Foundation (NRF) of South Africa and MONDI Packaging South Africa (MPSA) for funding.