Vegetable oil-derived epoxy monomers and polymer blends: A comparative study with review

Abstract

Abstract. Glycidyl esters of epoxidized fatty acids derived from soybean oil (EGS) and linseed oil (EGL) have been synthesized to have higher oxirane content, more reactivity and lower viscosity than epoxidized soybean oil (ESO) or epoxidized linseed oil (ELO). The EGS and ESO, for comparison, were used neat and in blends with diglycidyl ether of bisphenol A (DGEBA). Thermosetting resins were fabricated with the epoxy monomers and either BF 3 catalyst or anhydride. The curing behaviors, glass transition temperatures, crosslink densities and mechanical properties were tested. The results indicated that polymer glass transition temperatures were mostly a function of oxirane content with additional influence of glycidyl versus internal oxirane reactivity, pendant chain content, and chemical structure and presence of saturated components. EGS provided better compatibility with DGEBA, improved intermolecular crosslinking and glass transition temperature, and yielded mechanically stronger polymerized materials than materials obtained using ESO. Other benefits of the EGS resin blend systems were significantly reduced viscosities compared to either DGEBA or ESO-blended DGEBA counterparts. Therefore, EGS that is derived from renewable sources has improved potential for fabrication of structural and structurally complex epoxy composites, e.g., by vacuum-assisted resin transfer molding.

Green Nanocomposites from Renewable Plant Oils and Polyhedral Oligomeric Silsesquioxanes

“…Furthermore, various cationic polymerization of epoxidized plant oils can be achieved by photoinitiators, latent catalysts, or acid catalysts. These epoxy compounds from renewable resources possess high potential as a starting material for bio-based thermosetting plastics [35][36][37][38]. The composites of plant oil-based network polymers from epoxidized plant oils and inorganic substances were developed [39][40][41].…”

Synthesis and Properties of Polyesters from Waste Grapeseed Oil: Comparison with Soybean and Rapeseed Oils

“…ESBO derived polymers have been used mainly in nonstructural applications [24]. In polyesters ESBO has mainly been used as an additive and reactive diluent to partially replace BADGE, and as such can lower the cost and improve the processability of materials [49][50][51].…”

“…Typically, ESBO monomers are blended with commercial petrochemical epoxides, such as bisphenol A diglycidyl ether (BADGE), and reacted with anhydrides, such as maleic anhydride (MA), to give polyesters (epoxy resins). Usually an increase in renewable ESBO content leads to greater flexibility in the polymer with a loss in tensile strength (tensile strength; 100% BADGE/MA = 70 MPa, 100% ESBO/MA = 36 MPa) [24]. Unfortunately, replacing petrochemical epoxides (typically containing terminal epoxides) with less reactive plant oil derived internal epoxides leads to increases in cure temperatures by as much as 40°C [25].…”

“…1) is one of the most common vegetable oil feedstocks used in industry, traditionally it has been used as a plasticizer for PVC [22,23], as well as for producing polyesters from anhydrides [24][25][26].…”

Bio-based Flexible Network Polymer from Epoxidized Soybean Oil Reinforced by Poly(butyl methacrylate)

“…Acrylates and polyols derived from epoxidized plant oils have also been used as a monomer for preparation of bio-based polymeric materials (Biresaw et al 2008, Lligadas et al 2010, Luo et al 2011, Saithai et al 2013. Furthermore, various cationic polymerization of epoxidized plant oil can be achieved by photoinitiators, latent catalysts, or acid catalysts (Chakrapani & Crivello 1998, Shibata et al 2009, Wang & Schuman 2013. These epoxy compounds from renewable resources possess high potential as a starting material for bio-based thermosetting plastics , Petrović et al 2005, Campanella et al 2009, Gupta et al 2011.…”