Synthesis and Characterization of Novel Star-Shaped Itaconic Acid Based Thermosetting Resins
A star-shaped thermoset resin was synthesized by direct condensation reaction of itaconic acid and glycerol (star-Ita.Gly). In order to decrease the viscosity of the resin, the carboxyl groups of the oligomers were reacted with ethanol (Tstar-Ita.Gly). Chemical structures of the resins were studied by 1H and 13C NMR and Fourier-transform infrared spectroscopy (FT-IR). The curing process was optimized by studying the residual exotherms during the curing process. Thermomechanical properties of the cured samples were studied by Differential Scanning Calorimetry (DSC) and Dynamic Mechanical Analysis (DMA). Thermogravimetric analyses (TGA) were also carried out on both treated and pure resins to study the thermal stability of the cured samples. The viscosity of both resins were measured at different temperatures and different stress levels. Water adsorption tests were also carried out to check the water absorption properties of Tstar-Ita.Gly’s cured samples. The viscosity of the star-Ita.Gly was 154.9 Pa s at room temperature which dropped to 1.8 Pa s upon increasing the temperature to 70 °C. The viscosity of the Tstar-Ita.Gly resin was 0.35 Pa s at room temperature, and 0.04 Pa s at 70 °C. The glass temperature (Tg) of the alcohol-treated resin was 122 °C. Fully biobased content and inexpensive raw materials, biodegradability, very good thermomechanical and comparably very promising rheological properties and processability along with good thermal stability are of advantages of the synthesized resin which make the resin comparable with other thermosetting systems as well as the commercial unsaturated polyester resins.
KeywordsItaconic acid Synthesis Thermosets Crosslinking Star-shaped Thermal mechanical properties
The authors would like to acknowledge the funds provided by Agricultural Experiment Station, South Dakota State University and US Department of Agriculture, Washington, DC in support of this research work.
- 10.Bakare FO, Skrifvars M, Åkesson D, Wang Y, Afshar SJ, Esmaeili N (2014) Synthesis and characterization of bio-based thermosetting resins from lactic acid and glycerol. J Appl Polym Sci 131(13)Google Scholar
- 20.Kim SH, Kim YH (eds) (1999) Direct condensation polymerization of lactic acid. Macromolecular symposia. Wiley, New YorkGoogle Scholar
- 26.Lin Y, Zhang A, Wang L (2012) Synthesis and characterization of star-shaped poly(ethylene glycol)-block-poly(l-lactic acid) copolymers by melt polycondensation. J Appl Polym Sci 124(6):4496–4501Google Scholar
- 31.Vergnaud J-M, Bouzon J (2012) Cure of thermosetting resins: modelling and experiments. Springer, New YorkGoogle Scholar
- 34.Otsu T, Watanabe H, Yang JZ, Yoshioka M, Matsumoto A (eds) (1992) Synthesis and characterization of polymers from itaconic acid derivatives. Makromolekulare chemie Macromolecular symposia. Wiley, New YorkGoogle Scholar
- 36.Werpy T, Petersen G, Aden A, Bozell J, Holladay J, White J et al (2004) Top value added chemicals from biomass. Volume 1-results of screening for potential candidates from sugars and synthesis gas. DTIC DocumentGoogle Scholar
- 44.Jahandideh A, Esmaeili N, Muthukumarappan K (2017) Effect of lactic acid chain lengths on thermomechanical properties of star-LA-xylitol resins and jute reinforced biocomposites. Polym Int 66(7):1021–1030Google Scholar
- 47.Xiong JF, Wang QF, Peng P, Shi J, Wang ZY, Yang Cl (2014) Design, synthesis, and characterization of a potential flame retardant poly(lactic acid-co-pyrimidine-2,4,5,6-tetramine) via direct melt polycondensation. J Appl Polym Sci 131(10):1–10Google Scholar
- 54.Hisham SF, Ahmad I, Daik R, Ramli A (2011) Blends of LNR with unsaturated polyester resin from recycled PET: comparison of mechanical properties and morphological analysis with the optimum blend by commercial resin. Sains Malaysia 40(7):729–735Google Scholar
- 57.Bakare FO, Ramamoorthy SK, Åkesson D, Skrifvars M (2015) Thermomechanical properties of bio-based composites made from a lactic acid thermoset resin and flax and flax/basalt fibre reinforcements. Compos A 83:176–184Google Scholar
- 61.Li WH, Wong A, Leach D (eds) (2010) Advances in benzoxazine resins for aerospace applications. Proceedings of 2010 SAMPE international symposium, Seattle WA, SAMPE Covina CAGoogle Scholar
- 63.ASTM D570-98(2010)e1 (2010) Standard test method for water absorption of plastics. ASTM International, West Conshohocken, PA. http://www.astmorg.