Synthesis and characterization of an aromatic diamine and its polyimides containing asymmetric large side groups

A novel aromatic diamine monomer with asymmetric large side group: 4-(2,4,6-trimethyl)phenoxy-1,3-diaminobenzene, was synthesized by a two-step organic reaction. The monomer was separately subjected to a one-step high-temperature polycondensation reaction with three commercial aromatic dianhydrides to obtain a series of polyimides. Their structures and properties were characterized and studied by FTIR, NMR, UV, TGA, DSC, etc. The obtained polyimides showed excellent solubility not only in high-boiling solvents such as NMP, DMAc, and DMF, but also in low-boiling solvents such as CHCl 3 and CH 2 Cl 2 . Their tensile strength was in the range of 76.9–93.5 MPa, the elongation at break was between 4.8% and 7.3%, and the modulus of elasticity was in the range of 1.6–1.8 GPa. The obtained films exhibited good optical transparency, and the representative polyimide derived from 4,4′-oxydiphthalic dianhydride exhibited a light transmittance of more than 83% at a wavelength of 450 nm. Moreover, these polyimides also possessed good thermal properties. Their glass transition temperatures are between 285 °C and 345 °C, and the 10% weight loss temperature in air and nitrogen is above 463 °C, showing excellent thermal properties.