Synthesis of Aromatic Polyester (Polyarylate) by Removal of Phenol
from Condensation Polymerization of Bisphenol A and Diphenyl
Terephthalate/Isophthalate Mixtures

Takashi IWAMOTO†, Takashi KINOSHITA† and Junzo MASAMOTO*

Department of Polymer Science and Engineering, Kyoto Institute of Technology;
Matsugasaki, Sakyo-ku, Kyoto-shi 606-8585 Japan
† Chemicals and Plastics Development Laboratory, Asahi Chemical Industry Co., Ltd.;
3-13, Ushiodori, Kurashiki-shi 712-8633 Japan

Industrially available poly (bisphenol A arenedicarboxylate) (polyarylate) is conventionally produced by the interfacial condensation polymerization of bisphenol A and the mixture of terephthaloyl/isophthaloyl chlorides. We now report a new synthetic method without using the acid chloride derivatives, and the synthesis of oligomeric arenedicarboxylate by the melt condensation polymerization of bisphenol A and diphenyl terephthalate/isophthalate (mole ratio of reactants is 1/0.5/0.5). By removal of phenol from the reaction mixture, we obtained oligomeric ester, which can be changed to a high molecular weight polyester in the subsequent reactions. This report discussed the kinetics of the melt condensation of bisphenol A and diphenyl terephthalate/isophthalate mixtures. The melt condensation polymerization of bisphenol A and diphenyl terephthalate/isophthalate was analyzed by the bimolecular reaction of --OH and a phenyl ester. The activation energy was estimated to be 32.2 kcal/mol. The relationships between the reduced viscosity and molecular weight was estimated and the following experimental equation was obtained; ηsp/C=7.46×10−5− M0.83w. Polymer was analyzed by 1H-NMR, and the ratio of the end group of the hydroxy group to phenyl ester group was determined. FD-MS suggested four types of oligomeric ester end groups: phenyl-phenyl, phenyl-hydroxy, hydroxy-hydroxy, and cyclic.


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