Design and Effects of the Cinnamic Acids Chemical Structures as Organocatalyst on the Polymerization of Benzoxazines
Rocío B Rodríguez1, Daniela Iguchi1, Rosa Erra-Balsells2,3
1Design and Chemistry of Macromolecules Group, Institute of Technology in Polymers and Nanotechnology (ITPN), UBA-CONICET, FADU, University of Buenos Aires, Intendente Güiraldes 2160, Pabellón III, subsuelo, Ciudad Universitaria, Buenos Aires C1428EGA, Argentina.
Abstract:
This study focuses on the catalytic effect of the two geometric isomers of a cinnamic acid derivative, E and Z-forms of 3-methoxycinnamic acid (3OMeCA), analyzing the influence of their chemical structures. E and Z-3OMeCA isomers show very good catalytic effect in the polymerization of benzoxazines, decreasing by 40 and 55 °C, respectively, the polymerization temperatures, for catalyst contents of up to 10% w/w. Isothermal polymerizations show that polymerizations are easily realized and analyzed at temperatures as low as 130 °C and at much shorter times using Z-3OMeCA instead of E-3OMeCA. Thus, both cinnamic acids are good catalysts, with Z-3OMeCA being better. The molecular reasons for this difference and mechanistic implications in benzoxazine polymerizations are also presented.
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