Synthesis and properties of new polyimides derived from 1,1-bis[4-(4-aminophenoxy)phenyl]cyclododecane

Abstract

A new diamine, 1,1-bis[4-(4-aminophenoxy)phenyl] cyclododecane ( BAPCD), bearing flexible ether and bulky pendant cyclododecylidene groups was prepared in three steps from cyclododecanone. The monomer was reacted with six conventional aromatic dianhydrides in N, N-dimethylacetamide (DMAc) to obtain the corresponding new polyimides via the poly(amic acid) precursors and thermal or chemical imidization. The poly(amic acid)s obtained had inherent viscosities ranging from 1.10–1.42 dl g −1. All the poly(amic acid)s could be cast from DMAc solutions and thermally converted into transparent, flexible, and tough polyimide films, except for polymer V a which was derived from pyromellitic dianhydride. X-ray diffractograms of polyimides indicated all polymers were amorphous except the polymer V a . Polyimides derived from 4,4′-sulfonyldiphthalic anhydride and 4,4′-hexafluoroisopropylidenediphathalic anhydride exhibited excellent solubility in various polar solvents. These polymers showed glass transition temperatures between 259°C and 276°C, and decomposition temperatures at initial and 10% mass loss ranging from 430°C to 483°C and from 504°C to 526°C in nitrogen, respectively. The polyimide films, except V a , had a tensile strength in the range 76–112 MPa and a tensile modulus in the range 2.1–3.5 GPa.