2021 Annual Meeting

Incorporating Degradable and Reconfigurable Monomers into Vinyl Thermoplastics and Thermosets

Within the waste management system of plastics, polystyrene (PS) and polyvinyl chloride (PVC)
are of the least recycled even though they are thermoplastics, recyclable polymers. This is mainly due to
their chemical and physical properties. PVC produces gaseous hydrochloric acid when heated while PS is
a costly material to recycle. A possible solution to reducing the difficulty in recycling PS and PVC would
be to incorporate reconfigurable comonomers into these vinyl polymers. Doing so could allow the
polymers to more easily solvolyze into oligomers or crosslink into vitrimers. Through an SN2 reaction,
Meldrum’s acid is reacted with carbon disulfide and 1,4-dibromo-2-butene to synthesize a monomer for
radical ring-opening polymerization. However, after attempting to polymerize the compound using
several initiators and at various temperatures, it was determined that the monomer was not reactive
under these conditions. A more strained compound was computationally identified for future studies.