Tunable poly(hydroxyl urethane) from CO2‐Based intermediates using thiol‐ene chemistry |
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Authors: | Chau N Tang Hunaid B Nulwala Krishnan Damodaran Palwinder Kaur David R Luebke |
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Institution: | 1. National Energy Technology Laboratory, P.O. Box 10940, Pittsburgh, Pennsylvania 15236;2. Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260;3. Department of Chemical and Petroleum Engineering, University of Pittsburgh, Pittsburgh, Pennsylvania 15260 |
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Abstract: | CO2‐based, crosslinked poly(hydroxyl urethane)s (PHUs) are accessed via a set of efficient reactions based on the addition chemistry of thiol‐ene and amines‐cyclic carbonates. This strategy to utilize 5‐membered cyclic carbonates produced from CO2 is robust, facile, modular, and atomically efficient in nature. The thiol‐ene reaction was utilized to access bis(cyclic carbonate), tris(cyclic carbonate), and tetrakis(cyclic carbonate) in quantitative yield from 4‐vinyl‐1,3‐dioxolan‐2‐one and thiols. Multi‐functional cyclic carbonates were simply mixed with diethylenetriamine and/or 1,6‐diaminohexane to generate crosslinked PHUs from 25 to 80 °C. These materials are easy to scale‐up and are potential candidates in many applications such as coatings, binders, and resins. The resulting polymers have glass transition temperatures between ?1 and 16 °C and thermal decomposition temperatures from 190 to 230 °C. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011 |
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Keywords: | amine carbonate crosslinked polyurethanes poly(hydroxyl urethane)s thiol‐ene chemistry |
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