Three dimensional cross-linked polymers were synthesized using plant-based monomer carvomenthide prepared via alternative green procedure. Ring-opening transesterification polymerization of carvomenthide using diethylene glycol as an initiator gave telechelic hydroxyl poly(carvomenthide) (HO-PCM-OH). Adjusting monomer to initiator ratio, target molar masses of 3, 6, and 12 kg mol–1 were precisely controlled with narrow dispersity. Subsequently, hydroxyl functional groups were converted to carboxyl acid resulting acid-terminated poly(carvomenthide) (HOOC-PCM-COOH) by esterification with excess succinic anhydride. Transesterification or polymer chain scission was minimized during esterification, showing unimodal trace and low dispersity in size-exclusion chromatography (SEC). Thermal curing process of the resulting prepolymers was carried out at 180 °C with trifunctional aziridine to give cross-linked elastomers (XL-PCM). All polymers including HO-PCM-OH, HOOC-PCM-COOH, and thermoset elastomers exhibited high thermal resistance. The mechanical behavior of the thermoset elastomers were evaluated using dynamic mechanical analysis and tensile tests under static and cyclic loads, proving viscoelastic properties and rubbery behaviors with exceptional elongation at break, tensile strength, and elastomeric recovery properties. Cell adherence and proliferation on the elastomer surface were investigated for in vitro cytocompatibility. Therefore, this thermoset elastomer system derived from renewable materials offer useful approaches for the tissue engineering scaffold applications. References 1. Lee, S.; Kim, Y.-W.; Shin, J. et al. Biomacromolecules 2015, 16, 246–256. 2. Martinez, H.; Hillmyer, M. A. Macromolecules 2014, 47, 479–485.

Renewable crosslinked elastomer derived from carvomenthide

251st National Meeting (2016)

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