Syntheses and Properties of Polyamides and Polyesters Containing 1, 3, 5-Triazine Rings Using Diphenyl Ester

Abstract

Diesters containing 1, 3, 5-triazine ring ((1 a) and (1 b)) were prepared in dimethylsulfoxide (DMSO) by treating dicarboxylic acid and diphenylester with p, p'-bis (biguanidinophenyl) methane.
Polytriazinylamides (2) ware synthesized by copolycondensation of hexamethylenediamine with (1 a) and diphenyl adipate. Polytriazinylesters (3) were synthesized by copolycondensation of 1, 4-butanediol with (1 b) and diphenyl sebacate.
(2) had reduced viscosity O.4 - 1.4 dl/g in m-cresol and formed a hard flexible film. (2)became more soluble in methylcellosolve and DMSO with increasing 1, 3, 5-triazine ring content. Polymer melting temperature (Tm) gave the minimum values (240 C) at X=0.20 and above 330 C at X=0.40 - 1.0 as shown in Table 4.
The thermal stability was improved and specific gravity increased slowly from 1.14 to 1.25with increasing guanamine structure content.
(3) had reduce d viscosity 0.23 - 0.38 dl/g and formed a flexible film. (3) became slightly soluble in chloroform and readily soluble in DMSO and specific gravity increased with increasing 1, 3, 5-triazine ring content. Tm gave a curve of V-shape having a minimum value at X=0.40. The entropy of fusion of (3) (X=1) became much smaller than that of polytetramethylene sebacate (X=O).