Abstract
Regarding the sustainability point of view, this study is dedicated to the use of two bio-based star-shaped crosslinkers for superabsorbent hydrogel (SAP) applications as replacement of fossil-based counterparts. The epoxide crosslinker (E-st-G-SA) was synthesized from the reaction of a star-shaped macromonomer based-on glycerol and succinic acid with epichlorohydrin. The second crosslinker (C-st-G-SA) was prepared through the CO2 fixation reaction of E-st-G-SA. After characterization of crosslinkers by 1H NMR and FTIR spectroscopies, E-st-G-SA was used as an internal crosslinker for SAP formulations. Next, the potential of E-st-G-SA and C-st-G-SA as surface crosslinkers for the abovementioned SAP was examined and C-st-G-SA presented a significant improvement of swelling under load up to − 38%, so it was selected as the preferred surface crosslinker for additional investigations. Moreover, rheological properties of the surface crosslinked SAPs demonstrated a higher swollen gel strength compared to that of intact SAP. The thermal stability of the intact and surface crosslinked samples was compared and the result showed an overall similar trend. Finally, the antibacterial activity of samples was evaluated and the results presented a satisfactory antibacterial property especially against S. aureus bacterium for the surface crosslinked sample but not for the intact one.
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Zohuriaan-Mehr MJ, Kabiri K, Materials SP: Review A (2008) Iran Polym J 17:451–477. http://journal.ippi.ac.ir doi
Zohuriaan-Mehr MJ, Omidian H, Doroudiani S, Kabiri K (2010) Advances in non-hygienic applications of superabsorbent hydrogel materials. J Mater Sci 45:5711–5735. doi:https://doi.org/10.1007/s10853-010-4780-1
Moini N, Kabiri K, Zohuriaan-Mehr MJ, Omidian H, Esmaeili N (2017) Fine tuning of SAP properties via epoxy‐silane surface modification. Polym. Adv Technol 28:1132–1147
Shahi S, Zohuriaan-mehr MJ, Antibacterial superabsorbing hydrogels with high saline-swelling properties without gel blockage: Toward ideal superabsorbents for hygienic applications, J Bioact Compat Polym (2016) 1–18. doi:https://doi.org/10.1177/0883911516658782
Sina Shahi MJZ-M, Motasadizadeh HR (2017) Surface modification of superabsorbing hydrogels via a feasible esterification reaction: towards tunable superabsorbent for hygienic applications. Int J Polym Mater Polym Biomater 66:544–557. doi:https://doi.org/10.1080/00914037.2016.1252348
Azizi A, Kabiri K, Zohuriaan-mehr MJ, Bouhendi H, Karami Z, Zeinab K (2018) Transamidation: a feasible approach of surface modification to improve absorbency under load of agricultural superabsorbent materials. J Mater Res 33:2327–2335. doi:https://doi.org/10.1557/jmr.2018.240
Moini N, Kabiri K (2015) Effective parameters in surface cross-linking of acrylic-based water absorbent polymer particles using bisphenol A diethylene glycidyl ether and cycloaliphatic diepoxide. Iran Polym J 24:977–987
Moini N, Kabiri K, Zohuriaan-Mehr MJ, Esmaeili N (2016) Simple and efficient approach for recycling of fine acrylic-based superabsorbent waste. Polym Bull 73:1119–1133. doi:https://doi.org/10.1007/s00289-015-1538-6
Moini N, Kabiri K, Zohuriaan-Mehr MJ (2015) Practical improvement of SAP hydrogel properties via facile tunable cross-linking of the particles surface. Polym Plast Technol Eng 55:278–290. doi:https://doi.org/10.1080/03602559.2015.1070873
Ghasri M, Bouhendi H, Kabiri K, Jalal M, Mehr Z, Karami Z (2019) Superabsorbent polymers achieved by surface cross linking of poly (sodium acrylate) using microwave method. Iran Polym J 28:539–548. doi:https://doi.org/10.1007/s13726-019-00722-6
Auvergne R, Caillol S, David G, Boutevin B, Pascault JP (2014) Biobased thermosetting epoxy: present and future. Chem Rev 114:1082–1115. doi:https://doi.org/10.1021/cr3001274
Steinbüchel A, Christina, Andreeßen (2018) Recent developments in non-biodegradable biopolymers: precursors, production processes, and future perspectives. Appl Microbiol Biotechnol 103:143–157
Dabbaghi A, Ramazani A, Synthesis of bio - based internal and external cross ‐ linkers based on tannic acid for preparation of antibacterial superabsorbents, Polym. Adv Technol (2019) 1–12. doi:https://doi.org/10.1002/pat.4722
Jahandideh A, Muthukumarappan K (2017) Star-shaped lactic acid based systems and their thermosetting resins; synthesis, characterization, potential opportunities and drawbacks. Eur Polym J 87:360–379. doi:https://doi.org/10.1016/j.eurpolymj.2016.12.035
Jahandideh A, Esmaeili N, Muthukumarappan K (2018) Facile synthesis and characterization of activated star-shaped itaconic acid based thermosetting resins. Polym Degrad Stab 153:201–209. doi:https://doi.org/10.1016/j.polymdegradstab.2018.04.035
Esmaeili N, Jahandideh A, Åkesson D, Skrifvars M (2017) Synthesis and characterization of methacrylated star-shaped poly (lactic acid) employing core molecules with different hydroxyl groups. Appl Polym Sci 39:45341. doi:https://doi.org/10.1002/app.45341
Dabbaghi A, Jahandideh A, Kabiri K, Ramazani A, Zohuriaan-mehr MJ, The synthesis and incorporation of a star-shaped bio-based modifier in the acrylic acid based superabsorbent: a strategy to enhance the absorbency under load, Polym Technol Mater (2019) 1–13. doi:https://doi.org/10.1080/25740881.2018.1563140
Ghasri M, Jahandideh A, Kabiri K, Bouhendi H, Zohuriaan-Mehr M, Moini N, Glycerol-lactic acid star-shaped oligomers as efficient biobased surface-modifiers for improving superabsorbent polymer hydrogels, Polym. Adv Technol 30 (2018). doi:https://doi.org/10.1002/pat.4476
Akesson D, Skrifvars M, Seppala J, Turunen M, Martinelli A, Matic A (2010) Synthesis and characterization of a lactic acid-based thermoset resin suitable for structural composites and coatings. J Appl Polym Sci 115:480–486. doi:https://doi.org/10.1002/app
Zeinab Karami MJZ-M, Kabiri K (2019) Non-isocyanate polyurethane thermoset based on a bio-resourced starshaped epoxy macromonomer in comparison with a cyclocarbonate fossilbased epoxy resin: A preliminary study on thermo-mechanical and antibacterial properties. J CO2 Util 34:558–567
Shen L, Worrell E, Patel M (2010) Present and future development in plastics from biomass. Biofuels Bioprod Biorefining 4:25–40. doi:https://doi.org/10.1002/bbb
Guan J., Song Y., Lin Y., Yin X., Zhao M., Tao X., Zheng Q. (2011) Progress in study of non-isocyanate polyurethane. Ind. Eng. Chem. Res 50:6517–6527
Zohuriaan-Mehr MJ, Kabiri K (2008) Superabsorbent polymer materials: a review. Iran Polym J 17:451–477
Pavia DL, Lampman GM, Kriz GS, Vyvyan JA (2009) Introduction to spectroscopy. In: Nucl. Magn. Reson. Spectrosc, 4th edn. Cole, Cengage Learning, Whashington
Carré C, Bonnet L, Avérous L (2014) Original biobased nonisocyanate polyurethanes: solvent- and catalyst-free synthesis, thermal properties and rheological behaviour. RSC Adv 4:54018–54025. doi:https://doi.org/10.1039/C4RA09794G
Clements JH (2003) Reactive applications of cyclic alkylene carbonates. Ind Eng Chem Res 42:663–674
Buchholz GAT (1998) F. L., Modern superabsorbent polymer technology, 1st edn. Wiley-VCH, New York
Yazici I, Okay O, Spatial inhomogeneity in poly (acrylic acid) hydrogels, Polymer (Guildf). 46 (2005) 2595–2602. doi:https://doi.org/10.1016/j.polymer.2005.01.079
Pourjavadi A, Samadi M, Ghasemzadeh H (2008) Fast-swelling superabsorbent hydrogels from poly (2-hydroxy ethyl acrylate-co-sodium acrylate). Starch 60:79–86. doi:https://doi.org/10.1002/star.200700666
Pourjavadi A, Mahdavinia GR, Zohuriaan-Mehr MJ, Chitosan M (2003) II. H-ChitoPAN, a novel pHResponsive superabsorbent hydrogel. J Appl Polym Sci 90:3115–3121
Asri HC, Crismaru LATW, Roest M, Chen S, Ivashenko Y, Rudolf O, Tiller P, Van der Mei JC, Loontjens HJ, Busscher TJA (2014) A shape-adaptive, antibacterial-coating of immobilized quaternary-ammonium-compounds tethered on hyperbranched polyurea and its mechanism of action. Adv Funct Mater 24:346–355
Kenawy E-R, Worley SD, Broughton R (2007) The chemistry and applications of antimicrobial polymers: a state-of-the-art review. Biomacromolecules 8:1359–1384
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The authors would like to acknowledge the Iran National Science Foundation (INSF) for financial support (Grant No. 97004559).
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Karami, Z., Naderi, P., Kabiri, K. et al. Epoxidized and Cyclocarbonated Star-Shaped Macromolecules as Bio-Based Internal and External Crosslinkers for Superabsorbent Polymer Hydrogels. J Polym Environ 28, 1684–1695 (2020). https://doi.org/10.1007/s10924-020-01718-7
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DOI: https://doi.org/10.1007/s10924-020-01718-7