The Preparation of Electrolyte Hydrogels with the Water Solubilization of Polybenzoxazine
Abstract
:1. Introduction
2. Results and Discussion
3. Conclusions
4. Materials and Methods
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
- Ishida, H.; Agag, T. (Eds.) Handbook of Benzoxazine Resins; Elsevier: Amsterdam, The Netherlands, 2011. [Google Scholar]
- Ishida, H.; Froimowicz, P. (Eds.) Advanced and Emerging Polybenzoxazine Science and Technology; Elsevier: Amsterdam, The Netherlands, 2017. [Google Scholar]
- Takeichi, T.; Kawauchi, T.; Agag, T. High Performance Polybenzoxazines as a Novel Type of Phenolic Resin. Polym. J. 2008, 40, 1121–1131. [Google Scholar] [CrossRef]
- Lyu, Y.; Ishida, H. Natural-sourced benzoxazine resins, homopolymers, blends and composites: A review of their synthesis, manufacturing and applications. Prog. Polym. Sci. 2019, 99, 101168. [Google Scholar] [CrossRef]
- Lochab, B.; Monisha, M.; Amarnath, N.; Sharma, P.; Mukherjee, S.; Ishida, H. Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers. Polymers 2021, 13, 1260. [Google Scholar] [CrossRef] [PubMed]
- Machado, I.; Shaer, C.; Hurdle, K.; Calado, V.; Ishida, H. Towards the Development of Green Flame Retardancy by Polybenzoxazines. Prog. Polym. Sci. 2021, 121, 101435. [Google Scholar] [CrossRef]
- Gao, S.; Liu, Y.; Feng, S.; Lu, Z. Synthesis of borosiloxane/polybenzoxazine hybrids as highly efficient and environmentally friendly flame retardant materials. J. Polym. Sci. A Polym. Chem. 2017, 55, 2390–2396. [Google Scholar] [CrossRef]
- Wang, C.-F.; Su, Y.-C.; Kuo, S.-W.; Huang, C.-F.; Sheen, Y.-C.; Chang, F.-C. Low-surface-free-energy materials based on Polybenzoxazines. Angew. Chem. Int. Ed. 2006, 45, 2248–2251. [Google Scholar] [CrossRef]
- Juan, L.; Lu, X.; Xin, Z.; Zhou, C. Synthesis and Surface Properties of Low Surface Free Energy Silane-Functional Polybenzoxazine Films. Langmuir 2013, 29, 411–416. [Google Scholar] [CrossRef]
- Shang, Q.; Cheng, J.; Liu, C.; Hu, L.; Bo, C.; Hu, Y.; Yang, X.; Ren, X.; Zhou, Y.; Lei, W. Fabrication of sustainable and durable bio-polybenzoxazine based superhydrophobic cotton fabric for efficient oil/water separation. Prog. Org. Coat. 2021, 158, 106343. [Google Scholar] [CrossRef]
- Klfout, H.A.; Asiri, A.M.; Alamry, K.A.; Hussein, M.A. Recent advances in bio-based polybenzoxazines as an interesting adhesive coating. RSC Adv. 2023, 13, 19817–19835. [Google Scholar] [CrossRef] [PubMed]
- Tuzun, A.; Kiskan, B.; Alemdar, N.; Erciyes, A.T.; Yagci, Y. Benzoxazine containing polyester thermosets with improved adhesion and flexibility. J. Polym. Sci. A Polym. Chem. 2010, 48, 4279–4284. [Google Scholar] [CrossRef]
- Aydogan, C.; Kiskan, B.; Hacioglu, S.O.; Toppare, L.; Yagci, Y. Electrochemical manipulation of adhesion strength of polybenzoxazines on metal surfaces: From strong adhesion to dismantling. RSC Adv. 2014, 4, 27545–27551. [Google Scholar] [CrossRef]
- Shukla, S.; Ghosh, A.; Sen, U.K.; Roy, P.K.; Mitra, S.; Lochab, B. Cardanol benzoxazine-sulfur copolymers for Li-S batteries: Symbiosis of sustainability and performance. ChemistrySelect 2016, 1, 594–600. [Google Scholar] [CrossRef]
- Lin, L.-C.; Yen, H.-J.; Kung, Y.-R.; Leu, C.-M.; Lee, T.-M.; Liou, G.-S. Novel near-infrared and multi-colored electrochromic polybenzoxazines with electroactive triarylamine moieties. J. Mater. Chem. C 2014, 2, 7796–7803. [Google Scholar] [CrossRef]
- Gascó, C.; Rodríguez-Santiago, L.; Sodupe, M.; Sebastián, R.M.; Guirado, G. Electroinduced crosslinking of triphenylamine-based polybenzoxazines. Microchem. J. 2022, 182, 107878. [Google Scholar] [CrossRef]
- Wang, Y.; Wu, W.; Drummer, D.; Liu, C.; Shen, W.; Tomiak, F.; Schneider, K.; Liu, X.; Chen, Q. Highly thermally conductive polybenzoxazine composites based on boron nitride flakes deposited with copper particles. Mater. Des. 2020, 191, 108698. [Google Scholar] [CrossRef]
- Wang, W.; Liu, H.; Pei, L.; Liu, H.; Wang, M.; Li, S.; Wang, Z. Modified polybenzoxazine and carbon fiber surface with improved mechanical properties by introducing hydrogen bonds. Eur. Polym. J. 2023, 182, 111717. [Google Scholar] [CrossRef]
- Iguchi, D.; Ohashi, S.; Abarro, G.J.E.; Yin, X.; Winroth, S.; Scott, C.; Gleydura, M.; Jin, L.; Kanagasegar, N.; Lo, C.; et al. Development of Hydrogen-Rich Benzoxazine Resins with Low Polymerization Temperature for Space Radiation Shielding. ACS Omega 2018, 3, 11569–11581. [Google Scholar] [CrossRef] [PubMed]
- Goto, M.; Yajima, T.; Minami, M.; Sogawa, H.; Sanda, F. Synthesis and Cross-Linking of a Benzoxazine-Containing Anthracene Moiety: Thermally Stable Photoluminescent Benzoxazine Resin. Macromolecules 2020, 53, 6640–6648. [Google Scholar] [CrossRef]
- Ohara, M.; Yoshimoto, K.; Kawauchi, T.; Takeichi, T. Synthesis of high-molecular-weight benzoxazines having azomethine linkages in the main-chain and the properties of their thermosetting resins. Polymer 2020, 202, 122668. [Google Scholar] [CrossRef]
- Shibatsuka, T.; Kawauchi, T. Improvement of thermal properties of polybenzoxazines synthesized from an oligonuclear phenolic compound without sacrificing toughness by introducing crosslinkable groups separated by rigid biphenyl linkers. Polymer 2023, 265, 125613. [Google Scholar] [CrossRef]
- Zhu, Z.; West, S.; Chen, H.; Lai, G.-H.; Uenuma, S.; Ito, K.; Kotaki, M.; Sue, H.-J. Mechanically Interlocked Vitrimer Based on Polybenzoxazine and Polyrotaxane. ACS Appl. Polym. Mater. 2023, 5, 3971–3978. [Google Scholar] [CrossRef]
- Sharma, P.; Tanwar, V.; Tiwari, I.; Ingole, P.P.; Nebhani, L. Sustainable Upcycling of Nitrogen-Enriched Polybenzoxazine Thermosets into Nitrogen-Doped Carbon Materials for Contriving High-Performance Supercapacitors. Energy Fuels 2023, 37, 7445–7467. [Google Scholar] [CrossRef]
- Kiskan, B.; Yagci, Y. Self-healing of poly(propylene oxide)-polybenzoxazine thermosets by photoinduced coumarine dimerization. J. Polym. Sci. A Polym. Chem. 2014, 52, 2911–2918. [Google Scholar] [CrossRef]
- Arslan, M.; Kiskan, B.; Yagci, Y. Recycling and Self-Healing of Polybenzoxazines with Dynamic Sulfide Linkages. Sci. Rep. 2017, 7, 5207. [Google Scholar] [CrossRef]
- Zhang, K.; Han, M.; Liu, Y.; Froimowicz, P. Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources. ACS Sustain. Chem. Eng. 2019, 7, 9399–9407. [Google Scholar] [CrossRef]
- Adjaoud, A.; Puchot, L.; Verge, P. High-Tg and Degradable Isosorbide-Based Polybenzoxazine Vitrimer. ACS Sustain. Chem. Eng. 2022, 10, 594–602. [Google Scholar] [CrossRef]
- Duhan, V.; Amarnath, N.; Yadav, S.; Lochab, B. Greening Biobased Polybenzoxazine Network: Three Benefits in One Go. ACS Appl. Polym. Mater. 2023, 5, 2971–2982. [Google Scholar] [CrossRef]
- Machado, I.; Isabel Hsieh, I.; Rachita, E.; Salum, M.L.; Iguchi, D.; Pogharian, N.; Pellot, A.; Froimowicz, P.; Calado, V.; Ishida, H. A truly bio-based benzoxazine derived from three natural reactants obtained under environmentally friendly conditions and its polymer properties. Green Chem. 2021, 23, 4051–4064. [Google Scholar] [CrossRef]
- Osada, Y.; Khokhlov, A.R. (Eds.) Polymer Gels and Networks; Marcel Dekker: New York, NY, USA, 2002. [Google Scholar]
- Horkay, F.; Douglas, J.F.; Del Gado, E. (Eds.) Gels and Other Soft Amorphous Solids; ACS Symposium Series 1296; American Chemical Society: Washington, DC, USA, 2018. [Google Scholar] [CrossRef]
- Lee, K.Y.; Mooney, D.J. Hydrogels for Tissue Engineering. Chem. Rev. 2001, 101, 1869–1880. [Google Scholar] [CrossRef] [PubMed]
- Bonard, S.; Nandi, M.; García, J.I.H.; Maiti, B.; Abramov, A.; Díaz Díaz, D. Self-Healing Polymeric Soft Actuators. Chem. Rev. 2023, 123, 736–810. [Google Scholar] [CrossRef]
- Shibayama, M. Small-angle neutron scattering on polymer gels: Phase behavior, inhomogeneities and deformation mechanisms. Polym. J. 2011, 43, 18–34. [Google Scholar] [CrossRef]
- Ohsedo, Y.; Taniguchi, M.; Saruhashi, K.; Watanabe, H. Improved mechanical properties of polyacrylamide hydrogels created in the presence of low-molecular-weight hydrogelators. RSC Adv. 2015, 5, 90010–90013. [Google Scholar] [CrossRef]
- Gong, J.P.; Katsuyama, Y.; Kurokawa, T.; Osada, Y. Double-Network Hydrogels with Extremely High Mechanical Strength. Adv. Mater. 2003, 15, 1155–1158. [Google Scholar] [CrossRef]
- Haque, M.A.; Kurokawa, T.; Gong, J.P. Super tough double network hydrogels and their application as biomaterials. Polymer 2012, 53, 1805–1822. [Google Scholar] [CrossRef]
- Zhang, H.J.; Sun, T.L.; Zhang, A.K.; Ikura, Y.; Nakajima, T.; Nonoyama, T.; Kurokawa, T.; Ito, O.; Ishitobi, H.; Gong, J.P. Tough Physical Double-Network Hydrogels Based on Amphiphilic Triblock Copolymers. Adv. Mater. 2016, 28, 4884–4890. [Google Scholar] [CrossRef]
- Haraguchi, K.; Takehisa, T. Nanocomposite Hydrogels: A Unique Organic–Inorganic Network Structure with Extraordinary Mechanical, Optical, and Swelling/De-swelling Properties. Adv. Mater. 2002, 14, 1120–1124. [Google Scholar] [CrossRef]
- Haraguchi, K.; Uyama, K.; Tanimoto, H. Self-healing in Nanocomposite Hydrogels. Macromol. Rapid Commun. 2011, 32, 1253–1258. [Google Scholar] [CrossRef]
- Okumura, Y.; Ito, K. The Polyrotaxane Gel: A Topological Gel by Figure-of-Eight Cross-Links. Adv. Mater. 2001, 13, 485–487. [Google Scholar] [CrossRef]
- Liu, C.; Morimoto, N.; Jiang, L.; Kawahara, S.; Noritomi, T.; Yokoyama, H.; Mayumi, K.; Ito, K. Tough Hydrogels with Rapid Self-Reinforcement. Science 2021, 372, 1078–1081. [Google Scholar] [CrossRef]
- Kihara, N.; Hinoue, K.; Takata, T. Solid-State End-Capping of Pseudopolyrotaxane Possessing Hydroxy-Terminated Axle to Polyrotaxane and Its Application to the Synthesis of a Functionalized Polyrotaxane Capable of Yielding a Polyrotaxane Network. Macromolecules 2005, 38, 223–226. [Google Scholar] [CrossRef]
- Imran, A.B.; Esaki, K.; Gotoh, H.; Seki, T.; Ito, K.; Sakai, Y.; Takeoka, Y. Extremely stretchable thermosensitive hydrogels prepared by introducing polyrotaxane-based slide-ring cross-linkers and ionic groups into the polymer network. Nat. Commun. 2014, 5, 5124. [Google Scholar] [CrossRef] [PubMed]
- Sakai, T.; Matsunaga, T.; Yamamoto, Y.; Ito, C.; Yoshida, R.; Suzuki, S.; Sasaki, N.; Shibayama, M.; Chung, U.-I. Design and fabrication of a high-strength hydrogel with ideally homogeneous network structure from tetrahedron-like macromonomers. Macromolecules 2008, 41, 5379–5384. [Google Scholar] [CrossRef]
- Kamata, H.; Akagi, Y.; Kayasuga-Kariya, Y.; Chung, U.; Sakai, T. “Nonswellable” hydrogel without mechanical hysteresis. Science 2014, 343, 873–875. [Google Scholar] [CrossRef] [PubMed]
- Gong, J.P. Why are double network hydrogels so tough? Soft Matter 2010, 6, 2583–2590. [Google Scholar] [CrossRef]
- Long, R.; Hui, C.-Y.; Gong, J.P.; Bouchbinder, E. The Fracture of Highly Deformable Soft Materials: A Tale of Two Length Scales. Annu. Rev. Condens. Matter Phys. 2021, 12, 71–94. [Google Scholar] [CrossRef]
- Sawaryn, C.; Landfester, K.; Taden, A. Cationic Polybenzoxazines. A Novel Polyelectrolyte Class with Adjustable Solubility and Unique Hydrogen-Bonding Capabilities. Macromolecules 2011, 44, 7668–7674. [Google Scholar] [CrossRef]
- Dumas, L.; Bonnaud, L.; Olivier, M.; Poorteman, M.; Dubois, P. Arbutin-based benzoxazine: En route to an intrinsic water soluble biobased resin. Green Chem. 2016, 18, 4954–4960. [Google Scholar] [CrossRef]
- Mohamed, M.G.; Meng, T.S.; Kuo, W.S. Intrinsic water-soluble benzoxazine-functionalized cyclodextrin and its formation of inclusion complex with polymer. Polymer 2021, 226, 123827. [Google Scholar] [CrossRef]
- Periyasamy, T.; Asrafali, S.P.; Raorane, C.J.; Raj, V.; Shastri, D.; Kim, S.C. Sustainable Chitosan/Polybenzoxazine Films: Synergistically Improved Thermal, Mechanical, and Antimicrobial Properties. Polymers 2023, 15, 1021. [Google Scholar] [CrossRef]
- Periyasamy, T.; Asrafali, S.P.; Kim, S.-C. Bio-Based Polybenzoxazine–Cellulose Grafted Films: Material Fabrication and Properties. Polymers 2023, 15, 849. [Google Scholar] [CrossRef]
- Alhwaige, A.A.; Agag, T.; Ishida, H.; Qutubuddin, S. Biobased Chitosan/Polybenzoxazine Cross-Linked Films: Preparation in Aqueous Media and Synergistic Improvements in Thermal and Mechanical Properties. Biomacromolecules 2013, 14, 1806–1815. [Google Scholar] [CrossRef]
- Wang, T.-C.; Tsai, C.-Y.; Liu, Y.-L. Solid Polymer Electrolytes Based on Cross-Linked Polybenzoxazine Possessing Poly(ethylene oxide) Segments Enhancing Cycling Performance of Lithium Metal Batteries. ACS Sustain. Chem. Eng. 2021, 9, 6274–6283. [Google Scholar] [CrossRef]
- Zhang, X.; Zhao, J.; Xie, P.; Wang, S. Biomedical Applications of Electrets: Recent Advance and Future Perspectives. J. Funct. Biomater. 2023, 14, 320. [Google Scholar] [CrossRef]
- Liu, J.; Lu, X.; Xin, Z.; Zhou, C.-l. Surface Properties and Hydrogen Bonds of Mono-functional Polybenzoxazines with Different N-substituents. Chin. J. Polym. Sci. 2015, 34, 919–932. [Google Scholar] [CrossRef]
- Fleming, I.; Williams, D. Spectroscopic Methods in Organic Chemistry, 7th ed.; Springer Nature: Cham, Switzerland, 2019. [Google Scholar]
- Bienz, S.; Bigler, L.; Fox, T.; Meier, H. Spectroscopic Methods in Organic Chemistry, 3rd ed.; Thieme Chemistry, Georg Thieme Verlag KG: Stuttgart, Germany, 2021. [Google Scholar]
- Igder, A.; Pye, S.; Al-Antaki, A.H.M.; Keshavarz, A.; Raston, C.L.; Nosrati, A. Vortex fluidic mediated synthesis of polysulfone. RSC Adv. 2020, 10, 14761–14767. [Google Scholar] [CrossRef] [PubMed]
- Kusoglu, A.; Weber, A.Z. New Insights into Perfluorinated Sulfonic-Acid Ionomers. Chem. Rev. 2017, 117, 987–1104. [Google Scholar] [CrossRef] [PubMed]
- Xue, Z.; Heb, D.; Xie, X. Poly(ethylene oxide)-based electrolytes for lithium-ion batteries. J. Mater. Chem. A 2015, 3, 19218–19253. [Google Scholar] [CrossRef]
- Zhu, M.; Wu, J.; Wang, Y.; Song, M.; Long, L.; Siyal, S.H.; Yang, X.; Sui, G. Recent advances in gel polymer electrolyte for high-performance lithium batteries. J. Energy Chem. 2019, 37, 126–142. [Google Scholar] [CrossRef]
Sample | q |
---|---|
PB | 1.5 |
PB-A1-10 | 1.5 |
PB-A1-5 | 1.9 |
A1-10 | 4.9 |
A1-5 | 5.9 |
Sample | Ionic Conductivity (S cm−1) |
---|---|
Dried PB | 6.7 × 10−5 |
PB | 1.9 × 10−4 |
PB-A1-10 | 8.1 × 10−5 |
Dried PB-A1-10 | 8.9 × 10−5 |
PB-A1-5 | 1.3 × 10−4 |
Dried PB-A1-5 | 5.8 × 10−5 |
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Ohsedo, Y.; Kaneizumi, A. The Preparation of Electrolyte Hydrogels with the Water Solubilization of Polybenzoxazine. Gels 2023, 9, 819. https://doi.org/10.3390/gels9100819
Ohsedo Y, Kaneizumi A. The Preparation of Electrolyte Hydrogels with the Water Solubilization of Polybenzoxazine. Gels. 2023; 9(10):819. https://doi.org/10.3390/gels9100819
Chicago/Turabian StyleOhsedo, Yutaka, and Ami Kaneizumi. 2023. "The Preparation of Electrolyte Hydrogels with the Water Solubilization of Polybenzoxazine" Gels 9, no. 10: 819. https://doi.org/10.3390/gels9100819