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ARTICLE

Polymer Resins Synthesized via the Michael 1,4-addition from Tall Oil Fatty Acids Using Various Epoxidation Techniques

Aiga Ivdre*, Ralfs Pomilovskis, Arnis Abolins
Latvian State Institute of Wood Chemistry, Riga, LV-1047, Latvia
* Corresponding Author: Aiga Ivdre. Email: email
(This article belongs to the Special Issue: Advances in Biorefinery Technologies and Products – 2024)

Journal of Renewable Materials https://doi.org/10.32604/jrm.2024.056820

Received 31 July 2024; Accepted 23 October 2024; Published online 10 December 2024

Abstract

Studies on the use of renewable materials for various applications, including polymers, have gained momentum due to global climate change and the push towards a circular economy. In this study, polymer resins were developed through Michael 1,4-addition. The precursors were synthesized from tall oil-based acetoacetates derived from epoxidized tall oil fatty acids or their methyl esters. Two different epoxidation methods were employed: enzymatic epoxidation of tall oil fatty acids and ion-exchange resin epoxidation of tall oil fatty acid methyl esters. Following oxirane opening and transesterification with trimethylolpropane, further esterification or transesterification was carried out to obtain the acetoacetates. These synthesized acetoacetates were then reacted with acrylates of various functionalities to obtain polymer resins with differing degrees of crosslinking. The developed polymer resins were characterized using differential scanning calorimetry, dynamic mechanical analysis, and thermogravimetric analysis. The results indicated that the glass transition temperature and storage modulus of the polymer resins were significantly influenced by both the functionality of the acrylates used and the epoxidation technique employed. Higher acrylate functionality resulted in increased stiffness, while enzymatic epoxidation enhanced the polymer’s mechanical properties, nearly doubling the storage modulus, achieving approximately 470 MPa, compared to the ion-exchange resin technique. Therefore, selecting the appropriate acrylate functionality and epoxidation method could tailor the mechanical properties of the polymer resins.

Keywords

Tall oil fatty acids; bio-based resin; enzymes; epoxidation; enzymatic; ion resin; Michael 1,4-addition

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