Itaconic Acid as a Green Alternative to Acrylic Acid for Producing a Soybean Oil-Based Thermoset: Synthesis and Properties

Abstract

In this paper, itaconic acid was monomethylated with methanol to produce monomethyl itaconate, and then monomethyl itaconated epoxidized soybean oil (IESO) was obtained by melt ring-opening esterification of monomethyl itaconate with ESO. For comparison, acrylated epoxidized soybean oil (AESO) was also synthesized from ESO and acrylic acid with the same synthetic method. The chemical structures of monomethyl itaconate, IESO, and AESO were characterized in detail by differential scanning calorimetry (DSC), FTIR, and 1H NMR. The isothermal thermogravimetric analysis at 30, 60, and 90 °C indicated that monomethyl itaconate exhibited extremely low volatility even at 90 °C, while acrylic acid volatilized very fast even at 30 °C, which suggested that monomethyl itaconate could be used as a green alternative to acrylic acid. Under UV radiation, IESO showed good copolymerization ability with reactive monomers such as glycidyl methacrylate modified itaconic acid (IG), trimethylolpropane triacrylate (TMPTMA), and styrene. The cured neat IESO exhibited similar properties to the neat AESO, and the IESO/reactive monomers systems showed higher glass transition temperature (T g), modulus, and comparable or better tensile strength and coating properties than the AESO/reactive monomers systems.

Preparation and Properties of Plant-Oil-Based Epoxy Acrylate-Like Resins for UV-Curable Coatings

“…Plant-oil-based epoxy acrylate (EA) is one of the common UV-curable prepolymers, which is usually prepared through the ring-opening reaction of epoxidized plant oils with acrylic acid (AA) or its derivatives. Acrylated epoxidized soybean oil (AESO), perhaps the most often bio-based UV-curable prepolymer, has been proverbially employed in the fields of coatings and adhesives [ 7 , 15 , 20 , 21 , 22 ]. However, most of the reported oil-based EA resins usually possessed low stiffness and heat resistance, which greatly limited their application in the areas where petroleum-based EA resins can be used.…”

First Example of Unsaturated Poly(Ester Amide)s Derived From Itaconic Acid and Their Application as Bio-Based UV-Curing Polymers

“…The α,β-unsaturated double bonds, allows for radical polymerization reactions, which has been exploited in several homopolymers and co-polymers of itaconic acid with a range of applications [9][10][11][12][13]. As a second pathway, the two carboxylic acid groups allow for polycondensation reactions to obtain polyesters [14][15][16][17][18][19][20]. These have been used as reactive binder resins for coatings, shape-memory materials, printing inks, etc [21][22][23][24][25].…”

Epoxidized soybean oil cured with tannic acid for fully bio-based epoxy resin

“…In the EP eld in particular, exploring sustainable epoxy thermosets, including both EP and curing agents from renewable resources, has been an area of ever-increasing concern in recent years. [9][10][11][12] Different biomass resources, through years of research, such as plant oils, [13][14][15][16] isosorbide, 17,18 itaconic acid, 19,20 lignin derivatives, 21 vanillin, 22 and sugar, [23][24][25] have been used to design and prepare bio-based epoxy thermosets.…”