title: Smart, Sustainable, and Ecofriendly Chemical Design of Fully Bio-Based Thermally Stable Thermosets Based on Benzoxazine Chemistry.
abstract: A smart synthetic chemical design incorporating furfurylamine, a natural renewable amine, into a partially bio-based coumarin-containing benzoxazine is presented. The versatility of the synthetic approach is shown to be flexible and robust enough to be successful under more ecofriendly reaction conditions by replacing toluene with ethanol as the reaction solvent and even under solventless conditions. The chemical structure of this coumarin-furfurylamine-containing benzoxazine is characterized by FTIR, (1) H NMR spectroscopy and two-dimensional (1) H-(1) H nuclear Overhauser effect spectroscopy (2D (1) H-(1) H NOESY). The thermal properties of the resin toward polymerization are characterized by differential scanning calorimetry (DSC) and the thermal stability of the resulting polymers by thermogravimetric analysis (TGA). The results reveal that the furanic moiety induces a co-operative activating effect, thus lowering the polymerization temperature and also contributes to a better thermal stability of the resulting polymers. These results, in addition to those of natural renewable benzoxazine resins reviewed herein, highlight the positive and beneficial implication of designing novel bio-based polybenzoxazine and possibly other thermosets with desirable and competitive properties.
authors.affiliation: Design and Chemistry of Macromolecules Group, Institute of Technology in Polymers and Nanotechnology (ITPN), UBA-CONICET, School of Engineering, University of Buenos Aires., Av. Gral. Las Heras 2214 (CP 1127AAR), Buenos Aires, Argentina. pxf106@case.edu.
authors.forename: Pablo
authors.initials: P
authors.lastname: Froimowicz
authors.affiliation: Department of Macromolecular Science and Engineering, Case Western Reserve University, Cleveland, Ohio, 44106-7202, USA.
authors.forename: Carlos
authors.initials: C
authors.lastname: R Arza
authors.affiliation: Department of Macromolecular Science and Engineering, Case Western Reserve University, Cleveland, Ohio, 44106-7202, USA.
authors.forename: Lu
authors.initials: L
authors.lastname: Han
authors.affiliation: Department of Macromolecular Science and Engineering, Case Western Reserve University, Cleveland, Ohio, 44106-7202, USA. hxi3@case.edu.
authors.forename: Hatsuo
authors.initials: H
authors.lastname: Ishida
mesh_terms: D048588:Benzoxazines / Q000737:chemistry*; D003374:Coumarins / Q000737:chemistry; D015195:Drug Design; D004355:Drug Stability; D005663:Furans / Q000737:chemistry*; D055772:Green Chemistry Technology; D058105:Polymerization; D013696:Temperature
chemical_list: D048588:Benzoxazines; D003374:Coumarins; D005663:Furans; C439622:furfurylamine
keywords: benzoxazine; chemical design; ecofriendly; sustainable; thermoset