Polyacrylates are widely used polymers in industry, however their all aliphatic backbone leads to minimal degradability with challenges in recovery and recyclability. Insertion of a CO2 into the backbone, forming polycarbonate analogues of polyacrylates provides for an environmentally friendly alternative polymer. The synthesis of five polycarbonate analogues of poly(methyl acrylate), poly(ethyl acrylate), and poly(butyl acrylate) is described. The polymers are synthesized via the copolymerization of CO2 and an oxirane catalyzed by a salen cobalt complex. All of the carbonate acrylate analogues possess higher glass transition temperatures (Tg = 32 to -4.7 oC) than alkyl acrylates (Tg = 10 to -55 oC), however, the carbonate analogues undergo thermal decomposition at lower temperatures (&gt;100 oC difference). Additionally, we synthesized constitutionally isomeric polycarbonates where the pendant ester group is in the reverse orientation to the backbone to investigate how this electronic and steric change affects the bulk properties. Compared to the acrylate derivative, the reverse analogues possess lower thermal properties (Tg = 24 to 0 oC). However, the polymerization reactions are 10X more efficient and with more polymer product produced than the cyclic carbonate byproduct. Finally, the polycarbonate analogues degrade into glycerol, alcohol, and CO2 in a time and pH dependent manner with the rate of degradation accelerated at higher pH conditions. Both polycarbonate analogues degrade within an appreciable time span (3 to &gt;30 days) while the polyacrylate shows no degradation. Cytotoxicity studies indicate that all of the carbonate and acrylate polymers are non-toxic to NIH 3T3 fibroblast cells at 2.5 mg/mL concentration for 24 hours (ANOVA, p &gt;0.05).

Poly(alkyl glycidate carbonate)s as degradable poly(alkyl acrylates) analogues

256th National Meeting (2018)

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