Development of an Innovative Biobased UV Coating Synthesized from Acrylated Epoxidized Soybean Oil and Poly(octamethylene maleate (anhydride) citrate)

Abstract

Acrylated epoxidized soybean oil (AESO) as a biobased curable oligomer with different functionalities and poly­(octamethylene maleate (anhydride) citrate) (POMaC) as a biobased unsaturated monomer with polar groups were both synthesized. The chemical structures of POMaC and AESO were confirmed by Fourier transform infrared (FT-IR) and 1H nuclear magnetic resonance (1H NMR) spectroscopies. Then POMaC was used to copolymerize with AESO to prepare a series of high biobased content coatings via an ultraviolet (UV) curing process. The thermomechanical properties and coating properties in terms of hardness, adhesion, and water contact angle (WCA) were also investigated. The results show that AESO/POMaC coating has improved thermal stability and improved hardness compared with bare AESO-based coating. Furthermore, the adhesion of AESO/POMaC was markedly improved by 290%. The mechanism of adhesion enhancement was investigated by the combination of experiment and simulation. The decreased water contact angle represents the enhanced surface free energy of AESO/POMaC, and the molecular dynamics simulation results show higher binding energy and more hydrogen bonds of AESO/POMaC with the substrate. These results confirm that the polar groups and high soft-segment content of AESO/POMaC coating could strongly interact with the surface and could provide more adhesion contact area, which is responsible for the increased adhesion under dry and wet conditions. This work illustrates the potential of POMaC, as a renewable alternative component for the development of high-performance AESO-based green coatings in the future.

Bio‐Based Piezo‐ and Thermoresistive Photocurable Sensing Materials from Acrylated Epoxidized Soybean Oil

“…[13] Thus, accordingly to the European Green Deal and Circular Economy policies, [14] renewable feedstock materials are increasingly explored nowadays, including for UV-curable materials. [15,16] In fact, the consumption of nonrenewable energy and the carbon dioxide emission can be reduced through the use of natural-based materials, being bio-based thermoplastics widely available but bio-based thermosets still limited, representing thus an interesting and urgent challenge for materials research. [17] The use of renewable resources for the production of thermosets polymers are continuously increasing.…”

Polymers without Petrochemicals: Sustainable Routes to Conventional Monomers

“…As well as synthetic routes from fatty alcohols, other routes have been proposed to functionalize fatty acids directly. One method is through an epoxidation-acrylation approach. ,− The general approach is to first convert double bonds in the fatty acid to the corresponding epoxide through reaction with peracids or peroxides in the presence of a carboxylic acid, such as formic acid. ,− The epoxy group can then be ring-opened with acrylic acid resulting in the acrylate monomer. This procedure has been carried out on various different substrates including soybean oil and methyl oleate. ,− Huang and co-workers investigated two separate systems for the epoxidation of fatty esters .…”

Soybean oil‐based nanocomposites for dye adsorption: AESO‐chitosan‐graphene oxide synergy in water treatment

“…Over the past decade, the utilization of plant oils as eco‐friendly raw materials for the synthesis of biopolymers has garnered considerable attention within the scientific community 29 . Among the plant oil family, soybean oil and its derivatives stand out as some of the most accessible and well‐regarded members, with recent research exploring their applications in areas such as bioinks, 30 green composites, 31 bio‐based coatings, 32 and autonomous self‐healing materials 33 . The unsaturated fatty acid double bonds present in plant oils exhibit a high degree of reactivity.…”