Linear polymers with sulfur in the main chain. II. Synthesis of polyesters by interfacial polycondensation of bis(4,4′‐hydroxyphenyl)sulfide with several aliphatic acid dichlorides and their properties

Abstract

AbstractThe synthesis and properties of sulfur‐containing polyesters derived from bis(4,4′‐hydroxyphenyl)sulfide (TDP) and various acid dichlorides (AC) have been studied to evaluate the effect of the incorporation of sulfur in the main chains of polyesters. Polyesters derived from TDP and AC (with methylene numbers of 2–10) were synthesized by interfacial polycondensation in a 1,1,2,2‐tetrachloroethane /water mixture using tetra‐n‐butyl ammonium bromide as a phase transfer catalyst. Through the use of gel permeation chromatography, it was determined that the polyesters thus obtained had high molecular weights. The thermal properties of the polyesters including the TDP moiety were evaluated by thermogravimetry/differential thermal analysis and by differential scanning calorimetry. The analyses indicated that the polyesters including the TDP moiety were crystalline polymers with relatively high heat resistance. These polyesters were found to show an odd–even effect with the glass transition temperature and the melting point based on the methylene numbers. The tensile strength and storage modulus decreased with the methylene numbers. It was further found that the polyesters evidenced excellent barrier properties towards oxygen gas having an odd–even effect. In particular, it was shown that the polyesters with methylene numbers of 3, 4, 6, and 8 of methylene units have lower oxygen permeability than poly(ethylene terephthalate) (PET).©2003 Wiley Periodicals, Inc. J Appl Polym Sci 91: 1865–1872, 2004