Synthesis and characterization of new polyamides and polyimides prepared from 2,2-bis[4-(4-aminophenoxy)phenyl]adamantane

Abstract

In this work, we synthesized a new diamine containing a pendant adamantane group and a flexible aryl ether unit, 2,2-bis[4-(4-aminophenoxy)phenyl]adamantane (BAPA) in three steps starting from 2-adamantanone. A series of new polyamides having inherent viscosities of 0.72-0.90 dL.g -1 were prepared by direct polycondensation with aromatic dicarboxylic acids using triphenyl phosphite and pyridine as condensing agents. All polymers revealed an amorphous nature and were almost readily soluble in a variety of polar solvents. The glass transition temperature of these polyamides range from 254-294°C. The polyamides remain fairly stable up to a temperature around 450°C and lose 10% weight between 490 and 524°C in nitrogen atmosphere. A series of new polyimides were also synthesized from BAPA and various aromatic tetracarboxylic dianhydrides by the conventional two-step method. The inherent viscosities of polyimides were in the range of 0.66-0.77 dL.g -1 . The polyimides are amorphous and have glass transition temperatures between 276 and 310°C. Thermogravimetric analyses demonstrated that almost all polymers are stable up to 450 °C, and the 10% weight loss temperatures were recorded in the range of 515 to 541°C in nitrogen.