Polymers (Sep 2022)

The Synthesis of Bio-Based Michael Donors from Tall Oil Fatty Acids for Polymer Development

  • Ralfs Pomilovskis,
  • Inese Mierina,
  • Hynek Beneš,
  • Olga Trhlíková,
  • Arnis Abolins,
  • Anda Fridrihsone,
  • Mikelis Kirpluks

DOI
https://doi.org/10.3390/polym14194107
Journal volume & issue
Vol. 14, no. 19
p. 4107

Abstract

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In this study, the synthesis of a Michael donor compound from cellulose production by-products—tall oil fatty acids—was developed. The developed Michael donor compounds can be further used to obtain polymeric materials after nucleophilic polymerization through the Michael reaction. It can be a promising alternative method for conventional polyurethane materials, and the Michael addition polymerization reaction takes place under milder conditions than non-isocyanate polyurethane production technology, which requires high pressure, high temperature and a long reaction time. Different polyols, the precursors for Michael donor components, were synthesized from epoxidized tall oil fatty acids by an oxirane ring-opening and esterification reaction with different alcohols (trimethylolpropane and 1,4-butanediol). The addition of functional groups necessary for the Michael reaction was carried out by a transesterification reaction of polyol hydroxyl groups with tert-butyl acetoacetate ester. The following properties of the developed polyols and their acetoacetates were analyzed: hydroxyl value, acid value, moisture content and viscosity. The chemical structure was analyzed using Fourier transform infrared spectroscopy, gel permeation chromatography, size-exclusion chromatography and nuclear magnetic resonance. Matrix-assisted laser desorption/ionization analysis was used for structure identification for this type of acetoacetate for the first time.

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