Abstract
A series of materials was prepared by curing acrylated epoxidized soybean oil (AESO) and dibutyl itaconate (DBI) or ethyl cinnamate (EC) comonomers to provide examples of thermosets with a high proportion of bio-based carbon, in accordance with the principles of green chemistry. The comonomers, representative of cellulose-derived (DBI) or potentially lignin-derived (EC) raw materials, were tested at levels of 25%, 33%, and 50% by mass and the resulting products were characterized by infrared spectroscopy, thermogravimetric analysis, and dynamic mechanical analysis. Both DBI and EC were incorporated into the thermosets to a high extent (>90%) at all concentrations tested. The AESO-DBI and AESO-EC blends showed substantial degradation at 390–400 °C, similar to pure AESO. Glass transition temperatures decreased as comonomer content increased; the highest Tg of 41.4 °C was observed for AESO-EC (3:1) and the lowest Tg of 1.4 °C was observed for AESO-DBI (1:1). Accordingly, at 30 °C the storage modulus values were highest for AESO-EC (3:1, 37.0 MPa) and lowest for AESO-DBI (1:1, 1.5 MPa).
Highlights
The reactivity of olefins found in natural oils has been widely exploited as a means of preparing novel polymers with a high proportion of the carbon derived from renewable resources
The latter, in the form of acrylated epoxidized soybean oil (AESO, representative structure shown in Figure 1A) has been extensively developed as the foundation for a range of bio-based polymer and composite materials: AESO has been copolymerized with numerous petroleum-derived monomers such as alkyl acrylates and methacrylates, vinyl alcohol, vinyl acetate, acrylic acid, and styrene, in thermosetting reactions promoted by free radical initiators
Thermosets were prepared with AESO-dibutyl itaconate (DBI) or AESO-ethyl cinnamate (EC) mixtures with mass ratios of 3:1, 2:1, and
Summary
The reactivity of olefins found in natural oils has been widely exploited as a means of preparing novel polymers with a high proportion of the carbon derived from renewable resources. Unsaturated fatty chains may be converted to epoxides, which may be used in curing chemistries directly or further modified with reactive maleic or acrylic functionality [4]. The latter, in the form of acrylated epoxidized soybean oil (AESO, representative structure shown in Figure 1A) has been extensively developed as the foundation for a range of bio-based polymer and composite materials: AESO has been copolymerized with numerous petroleum-derived monomers such as alkyl acrylates and methacrylates, vinyl alcohol, vinyl acetate, acrylic acid, and styrene, in thermosetting reactions promoted by free radical initiators. The 12 Principles of Green Chemistry call for use of renewable resources whenever practicable [6,7], recent work has focused on maximizing the bio-based content in triglyceride-derived polymer systems
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