Renewable Myrcene-based UV-curable Monomer and its Copolymers with Acrylated Epoxidized Soybean Oil: Design, Preparation, and Characterization

Abstract

An innovative myrcene-based ultraviolet curable vinyl ester monomer was synthesized, and its molecular structure was analyzed with Fourier transform infrared spectroscopy and nuclear magnetic resonance ( 1 HNMR and 13 CNMR) analysis. A series of copolymers were also prepared by mixing the myrcene-derived monomer with another vinyl ester monomer, acrylated epoxidized soybean oil, under ultraviolet light. The curing process was monitored using Fourier transform infrared spectroscopy. Ultraviolet curing analysis showed that all the mixed systems had high curing rates and were fully cured within the first 30 seconds. When the weight ratio of myrcene-derived monomer to acrylated epoxidized soybean oil was 50/50, the ultimate double bond conversion reached 94.08%. Dynamic mechanical analysis showed that the storage modulus and glass transition temperature of the cured resins both increased with increasing content of myrcene vinyl ester monomer because the molecular structure of myrcene-derived vinyl ester monomer was more rigid and stronger than that of acrylated epoxidized soybean oil. Thermogravimetric analysis indicated that the main thermal initial decomposition temperatures were all above 360 °C, demonstrating that the copolymers had modest thermal stability.

Photoinitiator Free Resins Composed of Plant-Derived Monomers for the Optical µ-3D Printing of Thermosets

“…AESO can be polymerized by UV/VIS light using appropriate photoinitiators and can form a cross-linked polymer network. AESO is already photopolymerized with polycaprolactone diacrylate and polyethylenglycol diacrylate [25], tetrahydrophurphuryl acrylate [26,27], myrcene [28], and various thiols [29,30]. The addition of comonomers improved the mechanical and thermal properties as well as solvent resistance of the resulted polymers.…”

Soybean oil-based UV-curable coatings strengthened by crosslink agent derived from itaconic acid together with 2-hydroxyethyl methacrylate phosphate

“…[6,7] However, due to the flexible long aliphatic chain of soybean oil, as much as 50% or more petroleum-based rigid compounds, such as styrene [8,9], acrylate acid [10] and divinylbenzene [11,12], are necessary to make its mechanical or thermal properties acceptable for end use. Recently, with the rapid progress on bio-based materials, the exploration of bio-based compounds to strengthen the polymers derived from soybean oil so as to ensure a higher bio-based content has been frequently reported [5,[13][14][15][16][17]. For instance, acrylated sucrose monomers and tetrahydrofurfural acrylate were co-photopolymerized with AESO to obtain a highperformance coating with a higher bio-based content in Chen's work [13].…”

“…Liu et al [14] synthesized hyperbranched methacrylates (TAHAs) from tannic acid to improve the properties of AESO-based coatings. Yang et al reported the bio-based films with good coating properties derived from AESO and myrcene derivatives [15]. However, it is easy to notice that the volatile organic compounds (VOC) emission during the synthesis process is inevitable and eager to be overcome.…”

A Review on Styrene Substitutes in Thermosets and Their Composites

“…These commercially available or synthesized resins and their composites are attractive for respective merits and have been widely used in coating, adhesive, automobile parts, turbine blade, etc. [7,8,9,10,11].…”