Combining uretdione and disulfide reversibly degradable polyurethanes: route to alternating block copolymers

Abstract

Uretdione (temperature and catalyst controlled) and disulphide (REDOX controlled) functionalised polyurethanes have been described and the reversibility of these bonds tested. The polymers have been synthesised with reversible covalent groups present throughout their backbone, developing routes to reversibly degradable polyurethanes. These materials degrade and reheal in response to different external stimuli, which supplies a proof of concept for controlling the molecular weight, and therefore, the physical properties of a polyurethane. Further, a unique route to an alternating block copolymer is also discussed that utilises a mixture of disulphide and uretdione functionalised polymers as the reagents to form a thiourethane. The dramatically reduced safety hazards of dealing with the functionalised polymers, in comparison to the free isocyanate and thiols, could be of great interest to industrial application for current drives towards safer routes to polyurethanes.