Novel cationically polymerizable propenyl and vinyl ethers derived from renewable sources

Abstract

SYNOPSISThe preparation of several novel mono-and dipropenyl and divinyl ethers derived from renewable starting materials is described using simple, straightforward synthetic methods. Utilizing real-time infrared spectroscopy, the reactivity of the monomers in photoinitiated cationic polymerization was studied employing diaryliodonium and triarylsulfonium salts as photoinitiators. The monomers were shown to undergo very rapid cationic photopolymerization.

Bio-sourced monomers and cationic photopolymerization–The green combination towards eco-friendly and non-toxic materials

“…During the propagation step, polymerization proceeds, thereby consuming ether derivatives, until the density of the crosslinked network prevents the diffusion of unreacted monomer towards fixed reactive propagating centres. Gelation and subsequent vitrification drastically lower polymerization rates and significant amounts of vinyl ether monomers can remain trapped within the glassy polymer matrix [196].…”

“…In this matter, PHAs are biopolyesters also receiving increasing interest for their biodegradation ability and great potential for biobased drug delivery systems and tissue engineering applications. Alternatively, allylation and subsequent isomerization steps carried out on isosorbide afforded highly reactive vinyl and propenyl ether derivatives of isosorbide [196,319]. These monomers exhibited high reactivity in cationic photopolymerization experiments, with final monomer conversions higher than 60%.…”

Novel green route towards polyesters-based resin by photopolymerization of star polymers

“…the same ratio as that used for film formulations) into PDVE does not occur ( Figure 6 and 7a). Vinyl ether compounds are known to photopolymerize with a cationic photoinitiator and not with a radical photoinitiator [36,37]. Nevertheless, knowing that the vinyl ether cannot homopolymerize ( Figure 7a), and given the stoichiometric ratio maleate/vinyl ether used in the experiment, the full conversion of vinyl ether implies a full conversion of the maleate (Figure 7b).…”

The synthesis and cationic polymerization of novel monomers from renewable sources

“…One route which was employed for the conversion of cellulose or starch to cationically polymerizable monomers is shown in Scheme 2 (Ref. 19). Figure 3 shows a study of the photopolymerization of of these two monomers indicating that these monomers are very reactive.…”