Rigid Polyurethanes, Polyesters, and Polycarbonates from Renewable Ketal Monomers

S. Lingier, Y. Spiesschaert, B. Dhanis, S. De Wildeman, F.E. Du Prez*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

Two novel biobased diols containing rigid cyclic ketal functionalities have been synthesized on a relatively large scale from glycerol and two diketones, i.e., 1,4-cyclohexanedione and 4,4'-bicyclohexanone. The diols have been used in several types of step growth reactions, resulting in polycarbonates, polyesters, and polyurethanes. While molecular weights (M-n) of up to 50 kg mol(-1) are obtained for the polyurethanes, they also exhibit high glass transition (T-g = 95-150 degrees C) and degradation temperatures (T-d = 260-320 degrees C), are transparent, and show a high mechanical strength (E = 1.10-1.35 GPa) but brittle behavior. For the polycarbonates, M-n values higher than 24 kg mol(-1) and T-g's in the range of 70-100 degrees C have been obtained. Moreover, the polycarbonates show good mechanical properties like ductility and are transparent. Finally, a new generation of fully renewable polyesters have been synthesized with dimethyl succinate and dimethyl furan dicarboxylate. While moderate molecular weight values are obtained, the polyesters show T-g's of up to 96 degrees C as well as high T-d's (+/- 315 degrees C).
Original languageEnglish
Pages (from-to)5346-5352
Number of pages7
JournalMacromolecules
Volume50
Issue number14
DOIs
Publication statusPublished - 25 Jul 2017

Keywords

  • ACETALIZED GALACTARIC ACID
  • ALIPHATIC POLYESTERS
  • AROMATIC COPOLYESTERS
  • THERMAL-PROPERTIES
  • BIOBASED POLYMERS
  • BICYCLIC MONOMERS
  • MOLECULAR-WEIGHT
  • CO-POLYESTERS
  • BISPHENOL-A
  • D-MANNITOL

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