Publication Date

Spring 2016

Degree Type


Degree Name

Master of Science (MS)




Marc d'Alarcao

Subject Areas

Chemistry; Organic chemistry


Crosslinked polymers have a covalent bridge that connects two polymer strands at multiple points, creating a network or matrix that is very robust. These types of polymers may either be stable indefinitely, or degrade over time; those that degrade over time typically do so at a constant rate. What is not available currently is a polymer that is stable indefinitely, but then can be degraded on command. Being able to create an adhesive that could undergo de-bonding on command would be very useful. We have designed an electrochemically degradable crosslinking reagent (EDCR) composed of a bi-functional polymer crosslinking moiety and an electroactive core that undergoes degradation under reductive conditions. The EDCR is composed of a quinone center with two terminal amines attached. This crosslinker will be used to make a reversible epoxy adhesive. Epoxys are two-component adhesives that consist of a crosslinking amine hardener and an epoxide-containing polymer resin. Mixing of these components leads to a reaction between the epoxy groups and the terminal amines on the hardener. This work shows the construction of a protected form of an EDCR. Once deprotected, it should work as a hardener that will be stable indefinitely, but will degrade with the application of a low voltage current.