Polyanhydrides have found a niche in the degradable polymer field, largely because they often undergo surface erosion. An intriguing property of these polymers is the ability of the anhydride moiety to undergo dynamic covalent exchange, thus making them a covalent adaptable network (CAN) system. Using an approach based on radical-mediated thiol-ene polymerization, a facile step-growth polymerization, polyanhydrides with relatively uniform network structure can be readily made using photo, redox or thermal initiators and a wide variety of comonomers. We previously developed polyanhydride-poly(ε-caprolactone) composites that are not only capable of exhibiting shape memory properties but the dynamic covalent exchange between anhydride moieties also allows for permanent shape reconfiguration of the crosslinked polymer. We have exploited this process to create stress-free network (crosslinked) polyanhydrides that can be recycled. Furthermore, we studied the exchange dynamics of model compounds in order to understand the dependence of exchange on temperature, the presence of carboxylic acid, and anhydride molecular structure.

Dynamic covalent chemistry in polyanhydride networks

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