Quantitative Studies on the p-Substituent Effect of Phenolic Component on the Polymerization of Benzoxazines

TYLER HEYL; SEISHI OHASHI; PABLO FROIMOWICZ; DANIELA IGUCHI; HATSUO ISHIDA

Polymer Chemistry

Royal Society of Chemistry

Año: 2018 vol. 9 p. 4189 - 4252

1759-9954

Quantitative Studies on the p-Substituent Effect of Phenolic Component on the Polymerization of BenzoxazinesAbstractThe pure monofunctional benzoxazines substituted by either electron donating or withdrawing group are synthesized to verify the electronic effect in the polymerization behaviors without any complicated factors of the impurities. The analytical data of each compounds are collected by 1H-NMR, 13C-NMR, and differential scanning calorimetry (DSC). In order to quantify the electronic effect in the polymerization behavior, the Hammett substituent constant is utilized and plotted against resonances of 1H-NMR, 13C-NMR spectra and DSC exotherm maximum temperature. The use of the Hammett substituent constant is reexamined by calculating the natural charge on the phenolic moiety via ab initio calculation using Gaussian program and corelated with the polymerization exotherm temperature. The activation energies obtained by the Kissinger and Ozawa methods are related to the electronic effect of the substituents on phenolic part.