Polycycloacetals via polytransacetalization of diglycerol bisacetonide

Andrea Hufendiek, Sophie Lingier, Pieter Espeel, Stefaan De Wildeman, Filip E. Du Prez*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

3 Citations (Web of Science)

Abstract

Diglycerol bisacetonide was synthesized and isolated from acetone and diglycerol, which is renewable and available in large scale. DGA was directly used in polytransacetalization with 1,4-cyclohexanedione or 4,4-bicyclohexanone as diketone monomers. Polycycloacetals were obtained with molecular weights (M-n) of up to 28 kg mol(-1), broad dispersities (D = 1.5-4.0) and as semi-crystalline polymers with high melting points (T-m = 210-241 degrees C) and glass transition temperatures (T-g) of 48 degrees C or 65 degrees C. Introducing di(trimethylolpropane) (di-TMP) in the polymerization of DGA and 1,4-cyclohexanedione resulted in copolymers as confirmed by H-1-NMR and C-13-NMR spectroscopy. Increasing the di-TMP content from 10 to 50 mol% reduces the crystallinity of the polycycloacetals and increases the T-g, eventually yielding amorphous polymers (T-g = 60-71 degrees C). For the amorphous polycycloacetals, Young's moduli could be determined by tensile strength testing (E = 1.1-1.4 GPa). The polycycloacetals with renewable carbon contents in the range of 33-100% cover a wide range in material properties and are stable against hydrolysis at pH > 1-3, depending on the polycycloacetal composition.
Original languageEnglish
Pages (from-to)4789-4797
Number of pages9
JournalPolymer Chemistry
Volume9
Issue number38
DOIs
Publication statusPublished - 14 Oct 2018

Keywords

  • ACETAL METATHESIS POLYMERIZATION
  • DELIVERY VEHICLE
  • POLYKETAL MICROPARTICLES
  • GLYCEROL
  • POLYACETALS
  • POLYMERS
  • POLYURETHANES
  • POLYESTERS
  • COPOLYMERS
  • MONOMERS

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