(181be) Bio-Based Thermosets Prepared Using Aza-Michael Addition of Furan and Isosorbide Building Blocks
AIChE Annual Meeting
2019 AIChE Annual Meeting
Materials Engineering and Sciences Division
Poster Session: Materials Engineering & Sciences (08A - Polymers)
Monday, November 11, 2019 - 3:30pm to 5:00pm
The Aza-Michael addition reaction of (meth)acrylates with amines can be used for the preparation of thermosets for coating applications because fast reaction kinetics allow for rapid cure at a low temperature. Furan-based building blocks have been investigated as alternatives to incumbent phenolic systems and have been found to possess good mechanical and barrier properties. Multifunctional furan-based amine cross-linkers and Isosorbide Methacrylate (IM) were used to create thermosets utilizing the Aza-Michael addition reaction. The system can be cured at low temperatures in a relatively short period of time while yielding good thermal and mechanical properties due to high functionality of the amine cross-linkers and high reactivity of IM. In this investigation, the cure behavior of these new systems was investigated using spectroscopic techniques. The relative reactivity of primary and secondary amine was evaluated and formulations were obtained that resulted in IM conversion greater than 90%. Furthermore, furan-based epoxy was also introduced into the formulation to react with secondary amine moieties to add crosslinking to the system with improved glass transition temperature and modulus. It is found that unreacted secondary amines in such networks react freely with epoxy monomers providing additional control of network structure and composition. The Aza-Michael addition scheme for network formation provides an effective platform to design hybrid systems incorporating bio-based building blocks that express specific behavioral characteristics.