Synthesis, Characterization, and Study of Proton Exchange Polymer Membrane Properties of Sulfonated Copolymer Eugenol-diallyl Phthalate

Ngadiwiyana Ngadiwiyana; Nor Basid Adiwibawa Prasetya; Gunawan Gunawan; Tutuk Djoko Kusworo; Heru Susanto

doi:10.22146/ijc.55353

Synthesis, Characterization, and Study of Proton Exchange Polymer Membrane Properties of Sulfonated Copolymer Eugenol-diallyl Phthalate

https://doi.org/10.22146/ijc.55353

Ngadiwiyana Ngadiwiyana^(1*), Nor Basid Adiwibawa Prasetya⁽²⁾, Gunawan Gunawan⁽³⁾, Tutuk Djoko Kusworo⁽⁴⁾, Heru Susanto⁽⁵⁾

(1) Department of Chemistry, Faculty of Science and Mathematics, Universitas Diponegoro, Jl. Prof. Soedharto SH, Tembalang, Semarang 50275, Indonesia
(2) Department of Chemistry, Faculty of Science and Mathematics, Universitas Diponegoro, Jl. Prof. Soedharto SH, Tembalang, Semarang 50275, Indonesia
(3) Department of Chemistry, Faculty of Science and Mathematics, Universitas Diponegoro, Jl. Prof. Soedharto SH, Tembalang, Semarang 50275, Indonesia
(4) Department of Chemical Engineering, Faculty of Engineering, Universitas Diponegoro, Jl. Prof. Soedharto SH, Tembalang, Semarang 50275, Indonesia
(5) Department of Chemical Engineering, Faculty of Engineering, Universitas Diponegoro, Jl. Prof. Soedharto SH, Tembalang, Semarang 50275, Indonesia
(*) Corresponding Author

Abstract

Synthesis biopolymer of sulfonated copolymer eugenol-diallyl phthalate (PEGDAF), its characterization, and study of proton exchange polymer membrane properties had been done. This synthesis was conducted by eugenol and diallyl phthalate reaction to form PEGDAF, which is sulfonated using sulfuric acid. In addition, the functional groups of the PEGDAF and its sulfonated form were analyzed using FT-IR. Furthermore, the polymer properties were determined by measuring values of sulfonation degree, cation exchange capacity, proton conductivity, and water uptake. FT-IR spectra showed that the vinyl group had been added to the process of PEGDAF formation, while spectra deconvolution was used to confirm the occurrence of sulfonation reaction. The sulfonation of PEGDAF in 2 h optimum reaction time produces a black solid with a melting point of 133 °C in 16.55% yield. The highest proton conductivity, cation exchange capacity (CEC), and water uptake were 8.334 × 10^–6 S cm^–1, 0.44 meq/g, and 73.0%, respectively.

Keywords

eugenol; diallyl phthalate; membrane; proton exchange; polymer

Full Text:

Full Text PDF

References

[1] Modjinou, T., Versace, D.L., Abbad-Andallousi, S., Bousserrhine, N., Dubot, P., Langlois, V., and Renard, E., 2016, Antibacterial and antioxidant bio-based networks derived from eugenol using photo-activated thiol-ene reaction, React. Funct. Polym., 101, 47–53.

[2] Eissen, M., Metzger, J.O., Schmidt, E., and Schneidewind, U., 2002, 10 Years after Rio–Concepts on the contribution of chemistry to a sustainable development, Angew. Chem. Int. Ed., 41 (3), 414–436.

[3] Khalil, A.A., Ur Rahman, U., Khan, R.M., Sahar, A., Mehmood, T., and Khan, M., 2017, Essential oil eugenol: Sources, extraction techniques and nutraceutical perspectives, RSC Adv., 7, 32669–32681.

[4] Neda, M., Okinaga, K., and Shibata, M., 2014, High-performance bio-based thermosetting resins based on bismaleimide and allyl-etherified eugenol derivatives, Mater. Chem. Phys., 148 (1-2), 319–327.

[5] Li, Q., Ma, Z., Yue, Q., Gao, B., Li, W., and Xu, X., 2012, Synthesis, characterization and swelling behavior of superabsorbent wheat straw graft copolymers, Bioresour. Technol., 118, 204–209.

[6] Munavalli, B.B., and Kariduraganavar, Y.M., 2018, Enhancement of fuel cell performance of sulfonated poly(arylene ether ketone) membrane using different crosslinkers, J. Membr. Sci., 566, 383–395.

[7] Müller, F., Ferreira, C.A., Franco, L., Puiggalí, J., Alemán, C., and Armelin, E., 2012, New sulfonated polystyrene and styrene–ethylene/butylene–styrene block copolymers for applications in electrodialysis, J. Phys. Chem. B, 116 (38), 11767–11779.

[8] Ngadiwiyana, Ismiyarto, Gunawan, Purbowatiningrum, R.S., Prasetya, N.B.A., Kusworo, T.D., and Susanto, H., 2018, Sulfonated polystyrene and its characterization as a material of electrolyte polymer, J. Phys. Conf. Ser., 1025, 012133.

[9] Liu, S., Wang, L., Ding, Y., Liu, B., Han, X., and Song, Y., 2014, Novel sulfonated poly(ether ether ketone)/polyetherimide acid-base blend membranes for vanadium redox flow battery applications, Electrochim. Acta, 130, 90–96.

[10] Zhu, Y., Liang, C., Bo Y., and Xu, S., 2015, Compatibilization of polypropylene/recycled polyethylene terephthalate blends with maleic anhydride grafted polypropylene in the presence of diallyl phthalate, J. Polym. Res., 22 (3), 35.

[11] Prasetya, N.B.A., Ngadiwiyana, Ismiyarto, and Purbowatiningrum, R.S., 2019, Synthesis of copolymer eugenol crosslinked with divinyl benzene and preliminary study on its antibacterial activity, IOP Conf. Ser.: Mater. Sci. Eng., 509, 012102.

[12] An, D., Wu, B., Zhang, G., Zhang, W., and Wang, Y., 2016, Gradiently crosslinked polymer electrolyte membranes in fuel cells, J. Power Sources, 301, 204–209.

[13] Zhai, S., Dai, W., Lin, J., He, S., Zhang, B., and Chen, L., 2019, Enhanced proton conductivity in sulfonated poly(ether ether ketone) membranes by incorporating sodium dodecyl benzene sulfonate, Polymers, 11 (2), 203.

[14] Wang, Q., Lu, Y., and Li, N., 2016, Preparation, characterization and performance of sulfonated poly(styrene-ethylene/butylene-styrene) block copolymer membranes for water desalination by pervaporation, Desalination, 390, 33–46.

[15] Guimet, A., Chikh, L., Morin, A., and Fichet, O., 2016, Strengthening of perfluorosulfonic acid ionomer with sulfonated hydrocarbon polyelectrolyte for application in medium-temperature fuel cell, J. Membr. Sci., 514, 358–365.

[16] Larminie, J., and Dicks, A., 2013, Fuel Cell Systems Explained, 2^nd Ed., John Willey & Son, Chichester, England.

[17] Fang, J.H., 2018, “Polyimide proton exchange membranes” in Advanced Polyimide Materials, Synthesis, Characterization and Applications, Eds. Yang, S.Y., Elsevier Science, Amsterdam, 323–383.

[18] Kiswandono, A.A., Hadi, S., Mudasir, Sinjia, F., Sari, M.Y., and Irfan, M., 2019, Copoly eugenol crosslinked dialylphthalate 8% as a carrier in phenol and Pb(II) metal transport, J. Phys. Conf. Ser., 1338, 012004.

[19] Parnian, M.J., Rowshanzamir, S., and Gashoul, F., 2017, Comprehensive investigation of physicochemical and electrochemical properties of sulfonated poly(ether ether ketone) membranes with different degrees of sulfonation for proton exchange membrane fuel cell applications, Energy, 125, 614–628.

[20] Tang, Y., Xue, Z., Zhou, X., Xie, X., and Tang, C., 2014, Novel sulfonated polysulfone ion exchange membranes for ionic polymer-metal composite actuators, Sens. Actuators, B, 202, 1164–1174.

DOI: https://doi.org/10.22146/ijc.55353