Polymerization of Free Secondary Amine Bearing Monomers by RAFT Polymerization and Other Controlled Radical Techniques

Janoschka, Tobias; Teichler, Anke; Krieg, Andreas; Hager, Martin D.; Schubert, Ulrich S.

Abstract:

This work describes the polymerization of the free secondary amine bearing monomer 2,2,6,6-tetramethylpiperidin-4-yl methacrylate (TMPMA) by means of different controlled radical polymerization techniques (ATRP, RAFT, NMP). In particular, reversible addition-fragmentation chain transfer (RAFT) polymerization enabled a good control at high conversions and a polydispersity index below 1.3, thereby enabling the preparation of well-defined polymers. Remarkably, the polymerization of the secondary amine bearing methacrylate monomer was not hindered by the presence of the free amine that commonly induces degradation of the RAFT reagent. Subsequent oxidation of the polymer yielded the polyradical poly(2,2,6,6-tetramethylpiperidinyloxy-4-yl methacrylate), which represents a valuable material used in catalysis as well as for modern batteries. The obtained polymers having a molar mass (Mn) of 10,000–20,000 g/mol were used to fabricate well-defined, radical-bearing polymer films by inkjetprinting.

Year:

2012

Type of Publication:

Article

Keywords:

atom transfer radical polymerization ATRP; battery material; nitroxide mediated polymerization NMP; organic radical battery; radical polymerization; reversible addition fragmentation chain transfer polymerization RAFT; secondary amine; TEMPO polymer

Journal:

Journal of Polymer Science: Part A: Polymer Chemistry

Volume:

50

Pages:

1394-1407