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

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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