The synthesis of bio-based Michael donors from tall oil fatty acids for polymer development

0563192 - ÚMCH 2023 RIV CH eng J - Journal Article
Pomilovskis, R. - Mierina, I. - Beneš, Hynek - Trhlíková, Olga - Abolins, A. - Fridrihsone, A. - Kirpluks, M.
The synthesis of bio-based Michael donors from tall oil fatty acids for polymer development.
Polymers. Roč. 14, č. 19 (2022), č. článku 4107. E-ISSN 2073-4360
Grant - others:AV ČR(CZ) LZA-22-02
Program: Bilaterální spolupráce
Institutional support: RVO:61389013
Keywords : Michael addition components * Michael donor * tall oil fatty acids
OECD category: Polymer science
Impact factor: 5, year: 2022
Method of publishing: Open access
https://www.mdpi.com/2073-4360/14/19/4107

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.
Permanent Link: https://hdl.handle.net/11104/0335234