Amid-İmit ve Boronik Esterin Dinamik Bağlarını İçeren Bitkisel Yağ Bazlı Kompozit Vitrimerler

Öz

Son yıllarda çevre dostu, sürdürülebilir, yenilenebilir çapraz bağlı malzemeler oldukça odaklanılan bir araştırma alanı haline gelmiştir. Bu çalışmada bitkisel yağ esaslı tamamen sürdürülebilir malzemeler geliştirilmiştir. Bu amaçla tung yağı ve bitkisel bazlı amin, gallik asit ve borik asitten kompozit filmler hazırlanmıştır. Malzemeler, herhangi bir katalizör olmadan dinamik bağlarla mükemmel kendi kendini iyileştirme özellikleri sergilemiştir. Malzemelerin kendi kendine iyileşmesi hem amid-imid değişim reaksiyonları hem de borik asit ester bağları yoluyla sağlanmıştır. Sonuçlar, bu malzemelerin çeşitli endüstriyel uygulamalar için uygun maliyetli bir çözüm olma potansiyeline sahip olduğunu göstermektedir.

Anahtar Kelimeler

• sürdürülebilir malzemeler
• vitrimer
• kendi-kendini onarma
• bitkisel yağlar

Vegetable oil-based Composite Vitrimers containing Dynamic Bonds of Amide-Imide and Boronic Ester

Öz

Eco-friendly, sustainable, renewable cross-linked materials have become a highly focused area of research in recent years. In this study, vegetable oil-based fully sustainable materials were developed. For this purpose, the composite films were prepared from tung oil and vegetable-based amine, gallic acid, and boric acid. The materials exhibited excellent self-healing properties without any catalyst by dynamic bonds. Self-healing of the materials has been achieved through both amide-imide exchange reactions and boric acid ester bonds. The results show that these materials have the potential as a cost-effective solution for various industrial applications.

Anahtar Kelimeler

• sustainable materials
• vitrimer
• self-healing
• vegetable oils

Kaynakça

1. Wu, J., Yu, X., Zhang, H., Guo, J., Hu, J., & Li, M. H. (2020). Fully biobased vitrimers from glycyrrhizic acid and soybean oil for self-healing, shape memory, weldable, and recyclable materials. ACS Sustainable Chemistry & Engineering, 8(16), 6479-6487.
2. Liu, X., Zhang, E., Feng, Z., Liu, J., Chen, B., & Liang, L. (2021). Degradable bio-based epoxy vitrimers based on imine chemistry and their application in recyclable carbon fiber composites. Journal of Materials Science, 56, 15733-15751.
3. Gandini, A., Lacerda, T.M., Carvalho, A.J.F., Trovatti, E., (2016). Progress of polymers from renewable resources: furans, vegetable oils, and polysaccharides. Chem. Rev. 116, 1637–1669.
4. Altuna, F.I., Pettarin, V., Williams, R.J.J., 2013. Self-healable polymer networks based on the cross-linking of epoxidised soybean oil by an aqueous citric acid solution. Green Chem. 15, 3360–3366.
5. Zhang, S., Liu, T., Hao, C., Wang, L.W., Han, J.R., Liu, H., Zhang, J.W., 2018. Preparation of a lignin-based vitrimer material and its potential use for recoverable adhesives. Green Chem. 20, 2995–3000.
6. Shibata, M., Teramoto, N., & Nakamura, Y. (2011). High performance bio‐based thermosetting resins composed of tung oil and bismaleimide. Journal of Applied Polymer Science, 119(2), 896-901.
7. Li, F., & Larock, R. C. (2003). Synthesis, structure and properties of new tung oil− styrene− divinylbenzene copolymers prepared by thermal polymerization. Biomacromolecules, 4(4), 1018-1025.
8. Casado, U., Marcovich, N. E., Aranguren, M. I., & Mosiewicki, M. A. (2009). High‐strength composites based on tung oil polyurethane and wood flour: Effect of the filler concentration on the mechanical properties. Polymer Engineering & Science, 49(4), 713-721.

9. Biermann, U., Bornscheuer, U., Meier, M. A., Metzger, J. O., & Schäfer, H. J. (2011). Oils and fats as renewable raw materials in chemistry. Angewandte Chemie International Edition, 50(17), 3854-3871.
10. Chen, Y., Zhang, H., Majumdar, S., van Benthem, R. A., Heuts, J. P., & Sijbesma, R. P. (2021). Dynamic polyamide networks via amide–imide exchange. Macromolecules, 54(20), 9703-9711.
11. Zhang, H., Majumdar, S., van Benthem, R. A., Sijbesma, R. P., & Heuts, J. P. (2020). Intramolecularly catalyzed dynamic polyester networks using neighboring carboxylic and sulfonic acid groups. ACS Macro Letters, 9(2), 272-277.
12. Delahaye, M.; Winne, J. M.; Du Prez, F. E. Internal Catalysis in Covalent Adaptable Networks: Phthalate Monoester Transesterification As a Versatile Dynamic Cross-Linking Chemistry. J. Am. Chem. Soc. 2019, 141, 15277−15287.
13. Liu, Z.; Yu, C.; Zhang, C.; Shi, Z.; Yin, J. Revisiting Acetoacetyl Chemistry to Build Malleable Cross-Linked Polymer Networks via Transamidation. ACS Macro Lett. 2019, 8, 233−238.
14. Gallart-Sirvent, P., Li, A., Li, K., Villorbina, G., & Canela-Garayoa, R. (2017). Preparation of pressure-sensitive adhesives from tung oil via Diels-Alder reaction. International Journal of Adhesion and Adhesives, 78, 67-73.
15. Chen, L., Li, Z., Ma, Y., Shang, Q., Hu, Y., Huang, Q., Zhou, Y. (2023). Tung Oil-Based Degradable Vitrimer for Reprocessable and Recyclable Vitrimer–MWCNT Composites with Self-Healing Ability Triggered by Multiple Stimuli. ACS Applied Polymer Materials, 5(11), 9203-9212.
16. Oktay, B., Türkcan, J. H., Özdemir, O. K., & Kayaman-Apohan, N. (2023). Vegetable oil-based epoxy coating materials for self-healing and anticorrosive applications. Macromolecular Research, 31(11), 1077-1086.
17. Schmidt, M. P., Siciliano, S. D., & Peak, D. (2021). The role of monodentate tetrahedral borate complexes in boric acid binding to a soil organic matter analogue. Chemosphere, 276, 130150.
18. Güneş, I., & Oktay, B. (2023). Fabrication of Eco-friendly Sustainable Superhydrophobic and Anticorrosive Coatings from Acrylated Soybean Oil and Biobased Amine by the Aza-Michael Reaction. ACS Sustainable Chemistry & Engineering, 11(42), 15253-15261.
19. Hernández, M. F., Suárez, G., Cipollone, M., Conconi, M. S., Aglietti, E. F., & Rendtorff, N. M. (2017). Formation, microstructure and properties of aluminum borate ceramics obtained from alumina and boric acid. Ceramics International, 43(2), 2188-2195.
20. Teotonico, J., Mantione, D., Ballester-Bayarri, L., Ximenis, M., Sardon, H., Ballard, N., & Ruipérez, F. (2024). A combined computational and experimental study of metathesis and nucleophile-mediated exchange mechanisms in boronic ester-containing vitrimers. Polymer Chemistry, 15(3), 181-192.
21. M. Röttger, T. Domenech, R. Van Der Weegen, A. Breuillac, R. Nicolaÿ and L. Leibler, High-Performance Vitrimers from Commodity Thermoplastics through Dioxaborolane Metathesis, Science, 2017, 356(6333), 62–65.