Highly transparent and organosoluble poly(ether amide)s derived from new diamine: 10,10-bis [4-(4-amino-2-pyridinoxy)phenyl]-9(10H)-anthracenone

Abstract

A new aromatic diamine, 10,10-bis [4-(4-amino-2-pyridinoxy)phenyl]-9(10H)-anthracenone (BAPPA) was synthesized from anthrone as the starting material, and the corresponding pyridine- and anthrone-containing poly(ether amide)s (PEAs) were prepared from BAPPA with various aromatic diacid chlorides via a low-temperature solution polycondensation. The resulting PEAs having number-average molecular weights (Mn) of 29,500–33,400 g/mol with the polydispersity index ranged from 1.75 to 1.84, were all amorphous, and displayed excellent thermal stability with the glass transition temperatures of 263–355 °C, the temperatures of 415–441 °C at 5% weight loss and the higher than 50% residues at 800 °C in nitrogen. These new PEAs were soluble in polar solvents such as N-methyl-2-pyrrolidone, N,N-dimethylacetamide and pyridine, even almost in tetrahydrofuran at room temperature and could form transparent, strong and flexible films with tensile strengths of 84–97 MPa, tensile moduli of 2.1–3.2 GPa and elongations at break of 4–13%. Also, the present PEAs exhibited high optical transparence with the UV cutoff wavelength in the 342–362 nm range, and 83–90% transmittance at 500 nm. These results indicated the introduction of anthrone and pyridine groups into the backbone could improve the solubility and transparence of polyamides.