Mild incorporation of CO2 into epoxides: Application to nonisocyanate synthesis of poly(hydroxyurethane) containing triazole segment by polyaddition of novel bifunctional five-membered cyclic carbonate and diamines

5 years ago

Mild incorporation of CO2 into epoxides: Application to nonisocyanate synthesis of poly(hydroxyurethane) containing triazole segment by polyaddition of novel bifunctional five-membered cyclic carbonate and diamines

Takeshi Endo, Yoshio Furusho, Naoto Aoyagi

The cyclic amidinium iodide effectively catalyzed the ring-expansion addition of epoxides with carbon dioxide under ordinary pressure and mild conditions to obtain the corresponding five-membered cyclic carbonates in high yield. The novel triazole-linked bifunctional five-membered cyclic carbonate was synthesized successfully by the click reaction of the azide- and the alkyne-substituted five-membered cyclic carbonates under ambient temperature in high yield. The chemical structure of the novel bis(cyclic carbonate) was characterized by one- and two-dimensional nuclear magnetic resonance spectra. The obtained bis(cyclic carbonate) was converted with commercially available diamines to poly(hydroxyurethane) containing triazole segment without catalyst in high yield. Analyses of the resulting poly(hydroxyurethane)s were performed by proton nuclear magnetic resonance, size exclusion chromatography, thermogravimetric analysis, and differential scanning calorimetry. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018. The new triazole-linked bifunctional five-membered cyclic carbonate was synthesized via the reaction of epoxides with CO2 and the click reaction of the azide- and the alkyne-substituted five-membered cyclic carbonates under ambient temperature. The obtained bis(cyclic carbonate) was converted with diamines to the hydrophobic and the hydrophilic poly(hydroxyurethane)s containing triazole segment without catalyst. The thermal degradation behaviors of poly(hydroxyurethane)s were almost identical. The values of glass transition temperature of poly(hydroxyurethane)s were observed at around room temperature.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/pola.28967