Synthesis and Characterisation of Polymers Containing the Pyrrolidone Functional Group

Abstract

The exceptional properties of polymers containing the pyrrolidone functional group (aqueous & organic solvent soluble, high complexation ability, non-toxic and FDA approved) allow for wide-ranging product application. The development of pyrrolidone containing polymers is therefore, a highly interesting area for academic and commercial research. The focus of this project is the synthesis and characterisation of a range of novel pyrrolidone containing homo- and co-polymers. The work uses two approaches: 1) a bottom up, with the synthesis of known and novel pyrrolidone containing monomers and, 2) a top down, by functionalisation of commercially available polymer precursors.
A range of molecules containing the pyrrolidone moiety and monomer functional groups (styrene, epoxide and acrylate), were prepared. The homo- and co-polymerisation of the known and novel monomers, 1-(2-(oxiran-2-ylmethoxy) ethyl) pyrrolidin-2-one) or glycidyl ethylpyrrolidone (GEP, 1), 4-vinylbenzyloxy ethyl pyrrolidone (2) and 5-ethacryloxyethyl-12-ethylpyrrolidyl-N,N’hexane biscarbamate (3) were explored. The polymerisation methods were chosen to be synthetically simple, industrially viable and, were designed to produce pyrrolidone containing polymers with varying properties. The polymeric products were characterised by solution and solid state NMR, thermal analysis, mass spectrometry and, FTIR. GEP (1) was also successfully utilised in the post polymerisation modification of two commercial (poly(epichlorohydrin), poly(butadiene)) and one novel (poly(vinyl alcohol-graft-hyperbranched polyglycerol) (PVA-g-hPG)) polymer motifs.
The development, synthesis and characterisation of a range of novel pyrrolidone containing homo- and co-polymers is detailed herein. The success of the synthesis in an industrially viable manner provides a unique insight into the possibilities of pyrrolidone polymer progress.