Synthesis and characterization of new soluble cardo polyesters derived from 1,1-bis-[4-(4-chlorocarboxyphenoxy)phenyl]-4-tert-butylcyclohexane with various bisphenols by solution polycondensation

Authors

  • Der-Jang Liaw,

    Corresponding author
    1. Department of Chemical Engineering, National Taiwan University of Science and Technology, Taipei 106, Taiwan (Republic of China)
    • Department of Chemical Engineering, National Taiwan University of Science and Technology, Taipei 106, Taiwan (Republic of China)
    Search for more papers by this author
  • Jun-Jang Hsu,

    1. Department of Chemical Engineering, National Taiwan University of Science and Technology, Taipei 106, Taiwan (Republic of China)
    Search for more papers by this author
  • Been-Yang Liaw

    1. Department of Chemical Engineering, National Taiwan University of Science and Technology, Taipei 106, Taiwan (Republic of China)
    Search for more papers by this author

Abstract

A new cardo diacid chloride, 1,1-bis-[4-(4-chlorocarboxyphenoxy)phenyl]-4-tert-butylcyclohexane (4), was synthesized from 1,1-bis-[4-(4-carboxyphenoxy)phenyl]-4-tert-butylcyclohexane in refluxing thionyl chloride. Subsequently, various new polyesters were prepared from 4 with various bisphenols by solution polycondensation in nitrobenzene using pyridine as a hydrogen chloride quencher at 150 °C. These polyesters were produced with inherent viscosities of 0.32–0.50 dL · g−1. Most of these polyesters exhibited excellent solubility in a variety of solvents such as N,N-dimethylformamide, tetrahydrofuran, tetrachloroethane, dimethyl sulfoxide, N,N-dimethylacetamide, N-methyl-2-pyrrolidinone, m-cresol, o-chlorophenol, and chloroform. These polymers showed glass-transition temperatures (Tg's) between 144 and 197 °C. The polymer containing the adamantane group exhibited the highest Tg value. The 10% weight loss temperatures of the polyesters, measured by thermogravimetric analysis, were found to be in the range of 426–451 °C in nitrogen. These cardo polyesters exhibited higher Tg's and better solubility than bisphenol A-based polyesters. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 39: 2951–2956, 2001

Ancillary