Polymer, Vol.146, 12-20, 2018
Synthesis of semicrystalline poly(guanamine)s based on 2-substituted-4,6-dichloro-1,3,5-triazine with alpha, omega-alkylene diamines, and the formation of cyclic tetramers
Polycondensation of various 2-substituted-4,6-dichloro-1,3,5-triazine such as N,N-diphenylamino (DCPT), benzylamino (BnDCT) substituents with alpha, omega - alkylene diamines including hexamethylene (HMDA), octamethylene (OcDA), decamethylene (DcDA), and dodecamethylene diamine (DdDA) was performed, and the resultant polymers were analyzed. Two-phase polymerization in nitrobenzene/aqueous NaHCO3 at 100 degrees C resulted in a high molecular weight (MW) polymer (M-n = 12,400) with a small fraction (26.7 wt%) of low MW oligomer, whose main component was confirmed as a 4-membered cyclic compound. Polymers prepared with HMDA were crystalline with poor solubility, whereas those with OcDA, DcDA, and DdDA were all amorphous with high MWs (M-n = 40,000-60,000) and good solubility enough to prepare the self-standing transparent films. The polymers show moderate glass transition temperatures from 76 degrees C to 159 degrees C. In differential scanning calorimetry measurements, only poly(BnDCT-HMDA) showed a clear endothermic peak (Delta H = 119 J/g), which corresponds to melting at 220 degrees C. (C) 2018 Elsevier Ltd. All rights reserved.