Synthesis and characterization of novel polyimides based on 10,10-bis[4-(4-aminophenoxy)-3-methylphenyl]-9(10H)-anthrone

Abstract

10,10-Bis[4-(4-aminophenoxy)-3-methylphenyl]-9(10H)-anthrone, as a novel aromatic diamine, was synthesized from anthrone by three-step process. A series of polyimides containing methyl substituents and 9(10H)-anthrone pendant groups was prepared from this diamine with various aromatic dianhydrides via the poly(amic acid) (PAA) precursors and subsequent thermal or chemical imidization procedure. Inherent viscosities of PAAs are between 0.87 and 1.58 dL/g, and the corresponding polyimides have the weight-average molecular weight and number-average molecular weight in the range of 49,400–64,200 and 28,700–37,700, respectively. Most of the polyimides obtained through the chemical cyclodehydration method are soluble in NMP, DMF, DMAc, Py and m-cresol at room temperature. These polyimides have glass transition temperatures of 289–313 °C, 10% weight loss temperatures of 484–524 °C, char yields of 55–63% at 800 °C, and temperature at the maximum-rate degradation of 560–584 °C in nitrogen, respectively. The polyimide films obtained through the thermal imidization have tensile strength of 76.43–119.74 MPa, elongation at break of 6.93–12.33%, and tensile modulus of 1.91–2.38 GPa.

Graphical Abstract

Keywords:

• Aromatic polyimides
• 10,10-bis[4-(4-aminophenoxy)-3-methylphenyl]-9(10H)-anthrone
• bulky pendant groups
• ether linkages
• methyl substituents
• synthesis and properties