Diallyl Tartrate as a Multifunctional Monomer for Bio-polymer Synthesis

Abstract

This paper introduces the use of a diallyl dicarboxylate compound, diallyl tartrate, as a monomer in the synthesis of a biodegradable polymer. Although the allyl functional group is generally known for not being able to polymerize to high conversions, it was found in this study that by using photoinitiation instead of thermal initiation, a highly cross-linked polymer could be obtained from the polymerization of diallyl tartrate in a relatively short time. The details of the polymerization reaction were investigated in detail using differential photocalorimetry (DPC). The final thermoset obtained was shown to be completely amorphous and rigid, with a glass transition temperature of approx. 90 degrees C and a storage modulus of approx. 1 GPa at room temperature, via thermal analysis. It was also found to biodegrade in vitro via hydrolysis of its ester groups at a moderate rate, taking nearly 12 weeks to lose 50% of its mass. Both the photo-polymerized material and its water-soluble degradation products were further shown to be non-cytotoxic to fibroblast cells over at least 24 h of exposure. These results aim to initiate the use of this class of monomers in the synthesis of new polymers with tailored properties for biomaterial applications.

Synthesis of bio-sourced liquid resins and their photopolymerization with poly(ethylene glycol) diacrylate in the roadmap to more sustainable digital light processing technologies

“…The structures of the bio-based monomers were corroborated by comparison of the 1 H-NMR spectra with previously published works. 38,40 DAS is a symmetric molecule with only four signals in 1 H-NMR (Fig. S1.A†): one singlet at 2.63 ppm, from 4Hs of methylenes beside the carbonyl groups; 4Hs at 4.60 ppm, from methylene linked to the CH and oxygen from the ester group; a multiplet at ∼5.90 ppm attributed to 2Hs from CH– bonds; and two doublets at 5.31 ppm, corresponding to the 4Hs of the terminal double bond CH 2 .…”

Synthesis and characterization of novel biodegradable crosslinked polyesters

“…Such polymers based on the photopolymerization of diallyl compounds, however, have great potential for hard tissue engineering instead. Hence the results obtained on the synthesis and characterization of photopolymerized diallyl tartrate have been published [159] for its potential future use in bio-applications.…”