Nucleophilic amino acids as a renewable alternative to petrochemically-derived amines in glycerol epoxy resins

Yunyi Liang; Yonghong Luo; Yingji Wu; Xiaona Li; Quyet Van Le; Jianzhang Li; Changlei Xia

doi:10.1016/j.jobab.2024.01.003

Volume 9 Issue 2

May 2024

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Article Navigation > Journal of Bioresources and Bioproducts > 2024 > 9(2): 222-232

Yunyi Liang, Yonghong Luo, Yingji Wu, Xiaona Li, Quyet Van Le, Jianzhang Li, Changlei Xia. Nucleophilic amino acids as a renewable alternative to petrochemically-derived amines in glycerol epoxy resins[J]. Journal of Bioresources and Bioproducts, 2024, 9(2): 222-232. doi: 10.1016/j.jobab.2024.01.003

Citation:

Yunyi Liang, Yonghong Luo, Yingji Wu, Xiaona Li, Quyet Van Le, Jianzhang Li, Changlei Xia. Nucleophilic amino acids as a renewable alternative to petrochemically-derived amines in glycerol epoxy resins[J]. Journal of Bioresources and Bioproducts, 2024, 9(2): 222-232. doi: 10.1016/j.jobab.2024.01.003

Citation:

Yunyi Liang, Yonghong Luo, Yingji Wu, Xiaona Li, Quyet Van Le, Jianzhang Li, Changlei Xia. Nucleophilic amino acids as a renewable alternative to petrochemically-derived amines in glycerol epoxy resins[J]. Journal of Bioresources and Bioproducts, 2024, 9(2): 222-232. doi: 10.1016/j.jobab.2024.01.003

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Nucleophilic amino acids as a renewable alternative to petrochemically-derived amines in glycerol epoxy resins

doi: 10.1016/j.jobab.2024.01.003

a.
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, College of Materials Science and Engineering, Nanjing Forestry University, Nanjing 210037, China
b.
Department of Materials Science and Engineering, Institute of Green Manufacturing Technology, Korea University, Seoul 02841, South Korea

More Information

Corresponding author: E-mail address: changlei.xia@njfu.edu.cn (C. Xia)
Available Online: 2024-01-23
Publish Date: 2024-05-01

Abstract

Abstract

The standard epoxy resin curing agents revealed are from unsustainable petroleum-based sources, which produce poisonous exhaust when cured. Amino acids, a bio-based epoxy curing agent with amino and carboxyl groups, are another potential curing agent. Water-soluble epoxy resins cured with lysine (Lys), glutamic acid (Glu), leucine (Leu), and serine (Ser) as amino acids were investigated. The results showed that the water-soluble epoxy resin (glycerol epoxy resins, GER) was cured with Lys and Glu after reacting. Fourier transform infrared (FT-IR) spectroscopic analysis of the GER-Lys showed that the amino and carboxyl groups of Lys primarily reacted with the epoxy groups of GER. The elongation at break of Lys-cured GER (GER-Lys) cured at 70 ℃ with a molar ratio of 1꞉0.75 was 75.32%. The fact that elongations at break of GER-Lys (79.43%) were higher than those of GER-Glu (17.33%), respectively supports the decrease of crosslinking density by the amino acid-cured GER reaction. The potential of Lys and Glu alternatives for petrochemical amines is demonstrated and provides promising opportunities for industrial application.
- Curing agent,
- Amino acids,
- Bio-based epoxy resins,
- Lysine,
- Glutamic acid

Declaration of competing interest
There are no conflicts to declare.
^# Yunyi Liang and Yonghong Luo contributed equally to this work and should be considered co-first authors.

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References

Aadil, K.R., Jha, H., 2016. Physico-chemical properties of lignin–alginate based films in the presence of different plasticizers. Iran. Polym. J. 25, 661–670. doi: 10.1007/s13726-016-0449-1

Aristri, M.A., Lubis, M.A.R., Yadav, S.M., Antov, P., Papadopoulos, A.N., Pizzi, A., Fatriasari, W., Ismayati, M., Iswanto, A.H., 2021. Recent developments in lignin- and tannin-based non-isocyanate polyurethane resins for wood adhesives: a review. Appl. Sci. 11, 4242. doi: 10.3390/app11094242

Baroncini, E.A., Kumar Yadav, S., Palmese, G.R., Stanzione, J.F. Ⅲ, 2016. Recent advances in bio-based epoxy resins and bio-based epoxy curing agents. J. Appl. Polym. Sci. 133, 44103. doi: 10.1002/app.44103

Barth, A., 2000. The infrared absorption of amino acid side chains. Prog. Biophys. Mol. Biol. 74, 141–173. doi: 10.1016/S0079-6107(00)00021-3

Blake, L.I., Cann, M.J., 2022. Carbon dioxide and the carbamate post-translational modification. Front. Mol. Biosci. 9, 825706. doi: 10.3389/fmolb.2022.825706

Cividanes, L.S., Simonetti, E.A.N., Moraes, M.B., Fernandes, F.W., Thim, G.P., 2014. Influence of carbon nanotubes on epoxy resin cure reaction using different techniques: a comprehensive review. Polym. Eng. Sci. 54, 2461–2469. doi: 10.1002/pen.23775

Elizondo, N.J., Sobral, P.J.A., Menegalli, F.C., 2009. Development of films based on blends of Amaranthus cruentus flour and poly(vinyl alcohol). Carbohydr. Polym. 75, 592–598. doi: 10.1016/j.carbpol.2008.08.020

Froidevaux, V., Negrell, C., Caillol, S., Pascault, J.P., Boutevin, B., 2016. Biobased amines: from synthesis to polymers; present and future. Chem. Rev. 116, 14181–14224. doi: 10.1021/acs.chemrev.6b00486

Gaifutdinov, A.M., Andrianova, K.A., Amirova, L.M., Milyukov, V.A., Zagidullin, A.A., Amirov, R.R., 2022. Promising low-viscosity phosphorus-containing epoxy compounds: features of interaction with aromatic amines. Res. Eng. 14, 100421.

Gao, T.Y., Wang, F.D., Xu, Y., Wei, C.X., Zhu, S.E., Yang, W., Lu, H.D., 2022. Luteolin-based epoxy resin with exceptional heat resistance, mechanical and flame retardant properties. Chem. Eng. J. 428, 131173. doi: 10.1016/j.cej.2021.131173

Gu, W.D., Liu, X.R., Ye, Q.Q., Gao, Q., Gong, S.S., Li, J.Z., Shi, S.Q., 2020. Bio-inspired co-deposition strategy of aramid fibers to improve performance of soy protein isolate-based adhesive. Ind. Crops Prod. 150, 112424. doi: 10.1016/j.indcrop.2020.112424

Humphrey, J.M., Chamberlin, A.R., 1997. Chemical synthesis of natural product peptides: coupling methods for the incorporation of noncoded amino acids into peptides. Chem. Rev. 97, 2243–2266. doi: 10.1021/cr950005s

Ifuku, S., Nogi, M., Yoshioka, M., Morimoto, M., Yano, H., Saimoto, H., 2010. Fibrillation of dried chitin into 10–20 nm nanofibers by a simple grinding method under acidic conditions. Carbohydr. Polym. 81, 134–139. doi: 10.1016/j.carbpol.2010.02.006

Jiang, T.W., Reddy, K.S.K., Chen, Y.C., Wang, M.W., Chang, H.C., Abu-Omar, M.M., Lin, C.H., 2022. Recycling waste polycarbonate to bisphenol A-based oligoesters as epoxy-curing agents, and degrading epoxy thermosets and carbon fiber composites into useful chemicals. ACS Sustainable Chem. Eng. 10, 2429–2440. doi: 10.1021/acssuschemeng.1c07247

Jin, P.K., Song, J.N., Wang, X.C., Jin, X., 2018. Two-dimensional correlation spectroscopic analysis on the interaction between humic acids and aluminum coagulant. J. Environ. Sci. (China) 64, 181–189. doi: 10.1016/j.jes.2017.06.018

Kang, H.J., Wang, Z., Wang, Y.Y., Zhao, S.J., Zhang, S.F., Li, J.Z., 2019. Development of mainly plant protein-derived plywood bioadhesives via soy protein isolate fiber self-reinforced soybean meal composites. Ind. Crops Prod. 133, 10–17. doi: 10.1016/j.indcrop.2019.03.022

Lee, C.H., Wang, Y.Z., 2008. Synthesis and characterization of epoxy-based semi-interpenetrating polymer networks sulfonated polyimides proton-exchange membranes for direct methanol fuel cell applications. J. Polym. Sci. A Polym. Chem. 46, 2262–2276. doi: 10.1002/pola.22561

Li, Y., Xiao, F., Moon, K.S., Wong, C.P., 2006. Novel curing agent for lead-free electronics: Amino acid. J. Polym. Sci. A Polym. Chem. 44, 1020–1027. doi: 10.1002/pola.21239

Li, Y., Xiao, F., Wong, C.P., 2007. Novel, environmentally friendly crosslinking system of an epoxy using an amino acid: Tryptophan-cured diglycidyl ether of bisphenol A epoxy. J. Polym. Sci. A Polym. Chem. 45, 181–190. doi: 10.1002/pola.21742

Liang, Y.Y., Luo, Y.H., Wang, Y., Fei, T.Y., Dai, L.L., Zhang, D.H., Ma, H.Z., Cai, L.P., Xia, C.L., 2023. Effects of lysine on the interfacial bonding of epoxy resin cross-linked soy-based wood adhesive. Molecules 28, 1391. doi: 10.3390/molecules28031391

Luo, Y.H., Wang, Y., Xia, C.L., Ahmad, A., Yang, R., Li, X.N., Shi, S.Q., Li, J.Z., Guo, M., Nadda, A.K., Ahamad, T., Van Le, Q., 2022. Eco-friendly soy protein isolate-based films strengthened by water-soluble glycerin epoxy resin. Prog. Org. Coat. 162, 106566. doi: 10.1016/j.porgcoat.2021.106566

Milewski, A., Dydo, P., Jakóbik-Kolon, A., Czechowicz, D., Babilas, D., Burek, M., Waśkiewicz, S., Byczek-Wyrostek, A., Krawczyk, T., Kasprzycka, A., 2018. Preparation of triglycerol from glycerol and epichlorohydrin at room temperature: synthesis optimization and toxicity studies. ACS Sustain. Chem. Eng. 6, 13208–13216. doi: 10.1021/acssuschemeng.8b02817

Pawlukojć, A., Leciejewicz, J., Ramirez-Cuesta, A.J., Nowicka-Scheibe, J., 2005. L-Cysteine: neutron spectroscopy, Raman, IR and ab initio study. Spectrochim. Acta A Mol. Biomol. Spectrosc. 61, 2474–2481. doi: 10.1016/j.saa.2004.09.012

Rashid, M.A., Liu, W.S., Wei, Y., Jiang, Q.R., 2022. Review of intrinsically recyclable biobased epoxy thermosets enabled by dynamic chemical bonds. Polym. Plast. Technol. Mater. 61, 1740–1782. doi: 10.1080/25740881.2022.2080559

Reinhardt, N., Breitsameter, J.M., Drechsler, K., Rieger, B., 2022. Fully bio-based epoxy thermoset based on epoxidized linseed oil and tannic acid. Macromol. Mater. Eng. 307, 2200455. doi: 10.1002/mame.202200455

Shibata, M., Fujigasaki, J., Enjoji, M., Shibita, A., Teramoto, N., Ifuku, S., 2018. Amino acid-cured bio-based epoxy resins and their biocomposites with chitin- and chitosan-nanofibers. Eur. Polym. J. 98, 216–225. doi: 10.1016/j.eurpolymj.2017.11.024

Stagi, L., Farris, R., de Villiers Engelbrecht, L., Mocci, F., Maria Carbonaro, C., Innocenzi, P., 2022. At the root of l-lysine emission in aqueous solutions. Spectrochim. Acta A Mol. Biomol. Spectrosc. 283, 121717. doi: 10.1016/j.saa.2022.121717

Sun, T., Zhang, X.Q., Qiu, B.W., Luo, Y.F., Ling, Y.Q., Chen, Y., Xu, Z.W., Liang, M., Zou, H.W., 2022. Controllable construction of gradient modulus intermediate layer on high strength and high modulus carbon fibers to enhance interfacial properties of epoxy composites by efficient electrochemical grafting. Compos. Part B Eng. 247, 110279. doi: 10.1016/j.compositesb.2022.110279

Teng, N., Dai, J.Y., Wang, S.P., Hu, J.Y., Liu, X.Q., 2022. Hyperbranched flame retardant for epoxy resin modification: simultaneously improved flame retardancy, toughness and strength as well as glass transition temperature. Chem. Eng. J. 428, 131226. doi: 10.1016/j.cej.2021.131226

Tesser, R., Santacesaria, E., Di Serio, M., Di Nuzzi, G., Fiandra, V., 2007. Kinetics of glycerol chlorination with hydrochloric acid: A new route to α, γ-dichlorohydrin. Ind. Eng. Chem. Res. 46, 6456–6465. doi: 10.1021/ie070708n

Tian, Q., Yuan, Y.C., Rong, M.Z., Zhang, M.Q., 2009. A thermally remendable epoxy resin. J. Mater. Chem. 19, 1289–1296. doi: 10.1039/b811938d

Wang, W.T., Yu, B.S., Zhang, Y.W., Peng, M., 2022. Fully aminated rigid-rod aramid reinforced high strength epoxy resin and its composite with carbon fibers. Compos. Sci. Technol. 221, 109324. doi: 10.1016/j.compscitech.2022.109324

Yu, Z., Ma, S.Q., Liu, Y.L., Su, Y., Feng, H.Z., Li, P.Y., Dong, Y.X., Tang, Z.B., Zhang, K.W., Zhu, J., 2022. Facile synthesis of bio-based latent curing agent and its high-Tg epoxy network. Eur. Polym. J. 164, 110965. doi: 10.1016/j.eurpolymj.2021.110965

Zhang, X., Xu, C.J., Liu, Z., Shi, S.Q., Li, J.Z., Luo, J., Gao, Q., 2022a. A water-resistant and mildewproof soy protein adhesive enhanced by epoxidized xylitol. Ind. Crops Prod. 180, 114794. doi: 10.1016/j.indcrop.2022.114794

Zhang, Y.B., Liu, R., Yu, R.Z., Yang, K.M., Guo, L.L., Yan, H.X., 2022b. Phosphorus-free hyperbranched polyborate flame retardant: ultra-high strength and toughness, reduced fire hazards and unexpected transparency for epoxy resin. Compos. Part B Eng. 242, 110101. doi: 10.1016/j.compositesb.2022.110101

Zhang, Y.H., Yuan, L., Liang, G.Z., Gu, A.J., 2018. Developing reversible self-healing and malleable epoxy resins with high performance and fast recycling through building cross-linked network with new disulfide-containing hardener. Ind. Eng. Chem. Res. 57, 12397–12406. doi: 10.1021/acs.iecr.8b02572

Zhang, Z., Li, J.S., Wang, Z.Y., Long, S.Y., Jiang, S.J., Liu, G.L., 2020. Preparation and performance characterization of a novel high-performance epoxy resin modified reactive liquid asphalt. Constr. Build. Mater. 263, 120113. doi: 10.1016/j.conbuildmat.2020.120113

Zhong, Z.K., Sun, X.S., 2007. Plywood adhesives by blending soy protein polymer with phenol-formaldehyde resin. J. Biobased Mater. Bioenergy 1, 380–387. doi: 10.1166/jbmb.2007.014

Zou, G.L., Sun, X.K., Liu, X.H., Zhang, J.J., 2020. Influence factors on using recycled concrete aggregate in foamed asphalt mixtures based on tensile strength and moisture resistance. Constr. Build. Mater. 265, 120363. doi: 10.1016/j.conbuildmat.2020.120363

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