Bio‐based Epoxy Resins from Epoxidized Plant Oils and Their Shape Memory Behaviors

Abstract

In this study, bio‐based epoxy materials containing functionalized plant oil, such as epoxidized soybean oil (ESO) and epoxidized linseed oil (ELO), were processed with 4‐methylhexahydrophthalic anhydride (MHPA) as a curing agent. In the presence of tetraethylammonium bromide, the curing reaction of epoxidized plant oil and MHPA proceeded at 130 °C to give transparent plant oil‐based epoxy materials. The resulting bio‐based epoxy materials exhibited relatively soft and flexible characters, due to the aliphatic chains of plant oil. The thermal and mechanical properties of the ESO/MHPA polymers depended on the feed molar ratio of anhydride to oxirane. The mechanical properties such as tensile strength and Young's modulus of the ELO/MHPA polymer increased, compared with those of the ESO/MHPA polymer. The glass transition temperature of the ELO/MHPA polymer was higher than that of the ESO/MHPA polymer, because of the high oxirane number of ELO. Furthermore, the ELO/MHPA polymer showed excellent shape memory property.

Properties of biobased epoxy resins from epoxidized linseed oil (ELO) crosslinked with a mixture of cyclic anhydride and maleinized linseed oil

“…It is possible to obtain biobased epoxy resins with different approaches. In the last years, many investigations have been developed and characterized in the field of epoxy resins from vegetable oils such as epoxidized linseed oil (ELO) [13][14][15][16][17], modified soybean oil [15,16,[18][19][20][21][22][23][24] and other less known oils such as those derived from microalgal oil [25], jatropha oil [26], 407 Properties of biobased epoxy resins from epoxidized linseed oil (ELO) crosslinked with a mixture of cyclic anhydride and maleinized linseed oil M. D. Samper * , J. M. Ferri, A. Carbonell-Verdu, R. Balart, O. Fenollar Instituto de Tecnología de Materiales (ITM), Universitat Politècnica de València (UPV), Plaza Ferrándiz y Carbonell 1, 03801 Alcoy (Alicante), Spain karanja oil [27], tung oil [28], cottonseed oil [29] or hemp oil [30].…”

Bio-Based Epoxy Shape-Memory Thermosets from Triglycidyl Phloroglucinol

“…The cured resin showed good shape-memory properties: near 100% shape-recovery ratio, 97% shape-fixity ratio, and a fast shape-recovery speed. Tsujimoto et al [23] synthesized bio-based epoxy materials from epoxidized soybean oil (ESO) and epoxidized linseed oil (ELO) with 4-methylhexahydrophthalic anhydride (MHPA) as a curing agent. The materials showed shape-memory properties although the authors only evaluated them in qualitative way.…”

Shape memory polymer networks based on methacrylated fatty acids

“…Few of those works have focused in polymers with functional properties, reporting, for example, shape memory properties. Most of them were prepared by combining different proportions of a vegetable oil (as modified soybean oil or tung oil), with styrene (ST) and/or divinylbenzene (DVB) [8,18,19] while others were prepared from epoxidized vegetable oils (epoxidized soybean oil or epoxidized linseed oil) and a curing agents such as dicarboxylic acids and anhydrides [20,21]. Examples of the first group are the work of Meiorin et al [8] that reports the mechanical, damping and shape memory behavior of copolymers obtained by cationic copolymerization of tung oil with styrene at different stoichiometric ratios and the work of Li and Larock [18] that deals with the synthesis and characterization of bio-polymers obtained by cationic copolymerization of regular soybean oil, low saturation soybean oil (LoSatSoy oil), and/or conjugated LoSatSoy oil with styrene and divinylbenzene, norbornadiene, or dicyclopentadiene.…”

“…Examples of the first group are the work of Meiorin et al [8] that reports the mechanical, damping and shape memory behavior of copolymers obtained by cationic copolymerization of tung oil with styrene at different stoichiometric ratios and the work of Li and Larock [18] that deals with the synthesis and characterization of bio-polymers obtained by cationic copolymerization of regular soybean oil, low saturation soybean oil (LoSatSoy oil), and/or conjugated LoSatSoy oil with styrene and divinylbenzene, norbornadiene, or dicyclopentadiene. Regarding the second group, Wang et al [20] cured epoxy polymers (EPs) derived from soybean oil with varied chemical compounds containing anhydride groups to yield soybean-oil-derived epoxy polymers ranging from soft elastomers to tough thermosets, whose properties were adjusted by using different EPs and/or by controlling feed ratios of EPs to anhydrides; Tsujimoto et al [21] developed a polymer by curing epoxidized linseed oil with 4-methylhexahydrophthalic anhydride that showed excellent shape memory-recovery behavior. Likewise, sebacic acid was directly used to synthesize functional bio-polyesters by reacting it with 1,3-propanediol and itaconic acid [22].…”