1. Rapidly-cured isosorbide-based cross-linked polycarbonate elastomers
- Author
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Jeffery E. Raymond, Soon-Mi Lim, Lauren A. Link, Tyler S. Kristufek, Duncan J. Maitland, Karen L. Wooley, Samantha L. Kristufek, Sarosh Khan, Andrew C. Weems, and Alexander T. Lonnecker
- Subjects
Isosorbide ,Materials science ,Polymers and Plastics ,Bioengineering ,02 engineering and technology ,010402 general chemistry ,Elastomer ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Polymer chemistry ,medicine ,Trimethylolpropane ,Polycarbonate ,Organic Chemistry ,Thermal decomposition ,Substrate (chemistry) ,021001 nanoscience & nanotechnology ,0104 chemical sciences ,chemistry ,visual_art ,visual_art.visual_art_medium ,0210 nano-technology ,Glass transition ,Photoinitiator ,medicine.drug ,Nuclear chemistry - Abstract
The rapid synthesis of an optically-transparent, flexible elastomer was performed utilizing the naturally-derived source, isosorbide. A novel monomer based on isosorbide (isosorbide dialloc, IDA) was prepared by installing carbonate functionalities along with external olefins for use in thiol–ene click chemistry. Cross-linked networks were created using the commercially-available cross-linker, trimethylolpropane tris(3-mercaptopropionate) (TMPTMP) and resulted in IDA-co-TMPTMP, an optically-transparent elastomer. Systematically, IDA-co-TMPTMP networks were synthesized using a photoinitiator, a UV cure time of one minute and varied post cure times (0–24 h, 125 mm Hg) at 100 °C to observe effects on mechanical, thermal and surface alterations. The mechanical properties also had limited changes with post cure time, including a modulus at 25 °C of 1.9–2.8 MPa and an elongation of 220–344%. The thermal decomposition temperatures of the networks were consistent, ca. 320 °C, while the glass transition temperature remained below room temperature for all samples. A cell viability assay and fluorescence imaging with adherent cells are also reported in this study to show the potential of the material as a biomedical substrate. A degradation study for 60 days resulted in 8.3 ± 3.5% and 97.7 ± 0.3% mass remaining under accelerated (1 M NaOH, 60 °C) and biological conditions (pH 7.4 PBS at 37 °C), respectively. This quickly-synthesized material has the potential to hydrolytically degrade into biologically-benign and environmentally-friendly by-products and may be utilized in renewable plastics and/or bioelastomer applications.
- Published
- 2016