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Issue 15, 2016
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Rapidly-cured isosorbide-based cross-linked polycarbonate elastomers

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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.

Graphical abstract: Rapidly-cured isosorbide-based cross-linked polycarbonate elastomers

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Publication details

The article was received on 13 Oct 2015, accepted on 17 Mar 2016 and first published on 29 Mar 2016


Article type: Communication
DOI: 10.1039/C5PY01659B
Polym. Chem., 2016,7, 2639-2644

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    Rapidly-cured isosorbide-based cross-linked polycarbonate elastomers

    T. S. Kristufek, S. L. Kristufek, L. A. Link, A. C. Weems, S. Khan, S. Lim, A. T. Lonnecker, J. E. Raymond, D. J. Maitland and K. L. Wooley, Polym. Chem., 2016, 7, 2639
    DOI: 10.1039/C5PY01659B

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