Synthesis and characterization of itaconic‐based epoxy resins

Abstract

A trifunctional epoxy resin from itaconic acid (TEIA) was synthesized from a renewable resource-based itaconic acid by allylation of itaconic acid to form diallyl itaconate by using m-chloroperoxybenzoic acid as oxidizing agents followed by epoxidation of allylic C═C bond of diallyl itaconate methylhexahydropthalic anhydride as curing agent in the presence of 2-methyl imidazole as a catalyst. The chemical structure of the synthesized resins was confirmed by Fourier transform infrared and nuclear magnetic resonance ( 1 H-NMR and Pan et al [26] synthesized a highly functional bio-based epoxy resin from sucrose fatty acids. The higher epoxy value means that the highest number of epoxy rings, the more cross-linking occurs.Therefore, the result shows that higher mechanical properties and glass transition temperature contrast to commercialized bio-based epoxidized soybean oil (ESO). The overall properties of ESO were not similar to the conventional DGEBA, while they both are cured with methylhexahydrophthalic anhydride (MHHPA) curing agent because of the presence of long triglyceride aliphatic chain structure.Xin et al 27 synthesized cinnamic acid (Cin-epoxy)-based liquid epoxy resin with lower viscosity (0.67 Pa s) at room temperature than epoxy resin (DER 332; 3.31 Pa s), which indicates that Cin-epoxy systems have better processability and similar (T g 85°C) value of the biobased dimethylpropionic acid cured Cin-epoxy/dimethylpropionic acid networks and petroleum-based Cin-epoxy/HHPA network (T g 90°C).Samantha et al studied that the bio-based quercetin epoxy monomer that displayed comparable T g and thermal and mechanical properties than DGEBA was cured with nadic methyl anhydride curing agent.Wan et al 28 described that a eugenol-based epoxy resin (DEU-EP) with higher bio-based content of 70.2 wt% showed a higher storage,

Synthesis and characterization of petroleum and biobased epoxy resins: a review

“…Rosin is a mixture of acidic (90%) and neutral (10%) compounds. The acidic part is known as rosin acid and is a mixture of abietic type acid (40–60%) and pimaric type acids (9–27%) on the basis of total rosin weight . Rosin acid exhibits a large hydrogenated phenanthrene ring structure and is similar in rigidity to petroleum based cyclic aliphatic or aromatic compounds.…”

“…Owing to these exceptional properties, epoxy resins are utilized for various applications such as paintings, coatings, insulation materials, composites and constructions, as shown in Fig. . The market size of epoxy resins also reveals their significance: the epoxy resin market in North America was around $1.0 billion in 2015, and by 2020 it is expected to reach by $1.4 billion, and by 2017 the global epoxy production is anticipated to reach 3 million tons with a market size of $21.5 billion .…”

“…Furthermore, the uncertainties in the cost of petroleum as well as the social affinity towards renewable materials and sustainable resources have encouraged researchers to concentrate on biobased materials. Different renewable feedstocks, such as epoxidized plant oils, isosorbide, cardanol, lignin derivatives, itaconic acid and vanillin, have been used to synthesize biobased epoxy thermosets. The structure of the epoxide group is shown in Fig.…”

Synthesis and Characterization of Nanoclay‐Reinforced Trifunctional “Bioresin‐Modified” Epoxy Blends Enhanced with Mechanical and Thermal Properties

“…The static, heat-resistant temperature (T s ) is calculated by "Equation 1". [45,46] T s ¼ 0:49 T d5% þ 0:6 T d30% À T d5% ð Þ ½ ð 1Þ Table 4 indicates that the statistic heat-resistant index values of the cured virgin epoxy, epoxy/30%TEIA blend and nanocomposites system. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 Addition of 2.5 wt% clay into the epoxy blend the statistic heat-resistant of nanocomposites increased which is higher than the blend system and comparable to the virgin epoxy.…”

Itaconic acid used as a versatile building block for the synthesis of renewable resource‐based resins and polyesters for future prospective: a review

“…They are better alternatives to chemicals derived from petroleum feedstock. Gradually, they are increasing in the public consciousness, and as a result a higher demand for bio‐based materials and products is considered as an effective approach to reduce the dependency on petroleum resources and protect the living environment …”