Processable heat-resistant resins based on novel monomers containing o-phenylene rings: 2. Ordered benzoxazole- and benzthiazole-imide copolymers

Abstract

Highly processable heat-resistant resins containing o-phenylene rings have been prepared with high molecular weight from the reaction of simple aromatic dianhydrides with aromatic diamines containing preformed bisbenzoheterocyclic groups connected by an o-phenylene ring. Thus, 2,2′- o-phenylene-bis(5-aminobenzoxazole) was polycondensed with 3,3′4,4′-benzophenone dianhydride to yield a polyamic acid precursor, which was converted to an ordered benzoxazole-imide copolymer via cyclodehydration. Polymers can be prepared from diamines that are structural isomers, e.g. the amino groups can be in the 6-position instead of the 5-position. Additionally, polymers have been prepared from diamines, e.g. 2,2′- o-bis(6-aminobenzothiazole), having structurally similar heterocyclic units such as benzothiazole in place of benzoxazole rings. The preparation of the dinitro precursors to the bisbenzoheterocyclic diamines and their reduction is described along with nuclear magnetic resonance data. Polymers were characterized by differential scanning calorimetry, thermogravimetric analysis and inherent viscosity measurements of the polyamic acid precursors.