New transparent and thermally stable cardo poly(ether imide)s derived from 10,10-bis[4-(4-amino-2-pyridinoxy)phenyl]-9(10 H )-anthrone

Abstract

A new diamine bearing flexible ether, rigid pyridine, and bulky anthrone pendent group, 10,10-bis[4-(4-amino-2-pyridinoxy)phenyl]-9(10H)-anthrone (BAPPA), was prepared in three steps from anthrone. BAPPA was reacted with six conventional aromatic dianhydrides in N, N-dimethylacetamide (DMAc) to form the corresponding new poly(ether imide)s (PEIs) via the poly(ether amic acid) (PEAA) precursors with inherent viscosities ranging from 0.85 dL g⁻¹ to 1.26 dL g⁻¹ and thermal imidization. All the PEAAs could be cast from DMAc solution and thermally converted into transparent, flexible, and tough PEI films with tensile strength of 72.2–112.4 MPa, tensile modulus of 1.8–2.1 GPa, and elongation at break of 10–18%. These PEIs were predominantly amorphous and displayed excellent thermal stability with the glass transition temperature of 290–388°C, the 5% weight loss temperature of 480–514°C, and the residue of 68–43% at 800°C in nitrogen. The PEIs derived from 1,4-bis(3,4-dicarboxyphenoxy)benzene dianhydride and 4,4′-hexafluoroisopropylidenediphathalic anhydride exhibited excellent solubility in organic solvents such as N-methyl-2-pyrrolidinone, DMAc, N, N-dimethylformamide, pyridine, and even in tetrahydrofuran. Meanwhile, these PEIs also exhibited high optical transparency with the ultraviolet cutoff wavelength in the 374–427 nm range and the wavelength of 80% transparency in the range of 468–493 nm.