Bio-based thermo-healable non-isocyanate polyurethane DA network in comparison with its epoxy counterpart. (March 2017)

• Record Type: Journal Article
• Authors: Karami, Z.; Zohuriaan-Mehr, M.J.; Rostami, A.
• Is Part Of: Journal of CO₂ utilization. Volume 18(2017)
• Page Start: 294
• Page End: 302
• Publication Date: 2017-03
• Subjects: CO2 fixation -- Non-isocyanate polyurethane -- Diels-Alder reaction -- Thermo-mechanical properties -- Thermo-healing; Carbon dioxide -- Periodicals; Carbon dioxide -- Environmental aspects -- Periodicals; Carbon dioxide mitigation -- Periodicals; Carbon dioxide; Carbon dioxide -- Environmental aspects; Carbon dioxide mitigation; Periodicals; 628.53205
• DOI: 10.1016/j.jcou.2017.02.009
• Languages: English
• ISSNs: 2212-9820

Abstract

Graphical abstract: Highlights: A furfuryl cyclocarbonate ether based NIPU network was prepared, characterized and compared with its epoxy counterpart. Thermal and mechanical properties of the networks were investigated. Thermo-healability of the NIPU was superior than that of the epoxy counterpart. The NIPU solubility at retro-DA conditions makes it a good candidate for reusability. Abstract: Degradability, reusability or healability of polymer networks have significant importance in features of the environmental, economic and materials application. This study deals with synthesis of a reversible non-isocyanate polyurethane (NIPU) network in comparison with its epoxy counterpart. First, furfuryl cyclocarbonate ether (FCE) was synthesized by a green method of CO2 fixation (carbonation reaction) on furfuryl glycidyl ether (FGE; a bio-based compound). Afterwards, Diels-Alder (DA) adducts were synthesized by the reaction between a bismaleimide and FGE or FCE. The DA adducts were characterized by 1 H NMR and FTIR. Amine-curing of the adducts produced two different networks. According to dynamic mechanical thermal analysis, the existence of the cyclocarbonate ring resulted in the formation of a more flexible network having less cross-link density in comparison with its epoxy counterpart. Thermal behavior of the DA adducts were studied by differential scanning calorimetry (DSC) and thermogravimetric analysis. The results showed a retro-DA process occurred at ∼130 °C. Unlike the epoxy network, molecular disconnection of the NIPU network occurred completely at this temperature after 25 min. Disconnected moieties of both networks were re-casted and DA re-structuring of networks was confirmed by solubility test and DSC. Finally, the NIPU showed superior thermo-healing behavior comparing with its epoxy counterpart.