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Bio-based phthalonitrile compounds: Synthesis, curing behavior, thermomechanical and thermal properties

Publication date:

June 2018


Source:Reactive and Functional Polymers, Volume 127

Author(s): An-ran Wang, Abdul Qadeer Dayo, Li-wu Zu, Yi-le Xu, Dan Lv, Sha Song, Tao Tang, Wen-bin Liu, Jun Wang, Bao-chang Gao

Two bio-based phthalonitrile (PN) monomers, eugenol-based phthalonitrile (EPN) and guaiacol-based phthalonitrile (GPN), were successfully synthesized by the reaction of 4-nitrophthalonitrile with eugenol and guaiacol derived from clove and lignin, respectively, in the presence of potassium carbonate via nucleophilic substitution reaction. Their chemical structures were confirmed by the Fourier transform infrared spectra (FTIR), hydrogen and carbon nuclear magnetic resonances (1H and 13C NMR), and elemental analysis. The curing behavior of the blends of the prepared PN monomers with 10 wt% of 4-(4-aminophenoxy)-phthalonitrile (4-APN) as curing agent was evaluated by FTIR and differential scanning calorimetry (DSC), while rheometer was used to analyze the processability of the blends. Moreover, the thermomechanical and thermal properties of the polymers were studied by dynamic mechanical analyzer (DMA) and thermogravimetric analysis (TGA). The results confirmed that the bio-based PN monomers and its blends show low melting temperatures, wide processing windows (>186 °C), and low melt viscosity (<0.03 Pa·s). The cured bio-based PN resins exhibited higher glass transition temperature and better thermal stability and toughness than those of typical bisphenol A-based phthalonitrile polymer. Meanwhile, the phthalodinitrile resins form a homogeneous, void-free network structure, which also confirm the excellent thermal and mechanical properties of the polymers.
Graphical abstract




Authors:   Author(s): An-ran Wang, Abdul Qadeer Dayo, Li-wu Zu, Yi-le Xu, Dan Lv, Sha Song, Tao Tang, Wen-bin Liu, Jun Wang, Bao-chang Gao
Journal:   Reactive and Functional Polymers
Volume:   127
Year:   2018
Pages:   1
DOI:   10.1016/j.reactfunctpolym.2018.03.017
Publication date:   20-May-2018
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