Abstract
To modify the flexibility of chitosan (CS), poly(trimethylene carbonate) (PTMC) and its derivatives and copolymers were blended with a chitosan derivative, N,N,N-trimethylchitosan (TM-CS). The tensile strength of the CS and TM-CS films blended with PTMC was found to cause brittleness, but a PTMC derivative copolymer bearing carboxylic acid improved the elongation properties of TM-CS. A softer film was obtained for a blend film composed of TM-CS with 25% consisting of an added PTMC derivative copolymer bearing a 10% carboxylic acid moiety on the side chain. This film showed an elongation at break of 20.6 ± 9.3% with a tensile strength of 2.2 ± 0.83 MPa, while the original CS and TM-CS films showed an elongation at break of 7.4 ± 3.4% and 9.2 ± 1.6% with a tensile strength of 13.6 ± 1.0 MPa and 3.7 ± 0.35 MPa, respectively. This is the first report of the modification of CS using polymers with a PTMC backbone.
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References
Phillips PJ. Mechanism of orientation of aromatic molecules by stretched polyethylene. Chem Rev. 1990;90:425–36.
Chum PS, Swogger KW. Olefin polymer technologies – History and recent progress at The Dow Chemical Company. Prog Polym Sci. 2008;33:797–819.
Sturzel M, Mihan S, Mulhaupt R. From multisite polymerization catalysis to sustainable materials and all-polyolefin composites. Chem Rev. 2016;116:1398–433.
Malikmammadov E, Tanir TE, Kiziltay A, Hasirci V, Hasirci NPCL. and PCL-based materials in biomedical applications. J Biomater Sci Polym Ed. 2018;29:863–93.
Tempelaar S, Mespouille L, Coulembier O, Dubois P, Dove AP. Synthesis and post-polymerization modifications of aliphatic poly(carbonate)s prepared by ring-opening polymerization. Chem Soc Rev. 2013;42:1312–36.
Sionkowska A. Current research on the blends of natural and synthetic polymers as new biomaterials: Review. Prog Polym Sci. 2011;36:1254–76.
Imre B, Pukanszky B. Compatibilization in bio-based and biodegradable polymer blends. Eur Polym J. 2013;49:1215–33.
Saini P, Arora M, Ravi Kumar MNV. Poly(lactic acid) blends in biomedical applications. Adv Drug Deliv. Rev 2016;107:47–59.
Kun D, Pukanszky B. Polymer/lignin blends: Interactions, properties, applications. Eur Polym J. 2017;93:618–41.
Wang C, Kelley SS, Venditti RA. Lignin-based thermoplastic materials. CHEMSUSCHEM. 2016;9:770–83.
Pillai CKS, Paul W, Sharma CP. Chitin and chitosan polymers: Chemistry, solubility and fiber formation. Prog Polym Sci. 2009;34:641–78.
Liu X, Hu Q, Fang Z, Zhang X, Zhang B. Magnetic chitosan nanocomposites: A useful recyclable tool for heavy metal ion removal. Langmuir. 2009;25:3–8.
Jung CL, Park SC, Lim H. Synthesis of surface-reinforced biodegradable chitosan nanoparticles and their application in nanostructured antireflective and self-cleaning surfaces. ACS Appl Mater Interf. 2019;11:40835–41.
Zhou X, Wang H, Zhang J, Li X, Wu Y, Wei Y, et al. Functional poly(ε-caprolactone)/chitosan dressings with nitric oxide-releasing property improve wound healing. Acta Biomaterialia. 2017;54:128–37.
Zhao X, Wu H, Guo B, Dong R, Qiu Y, Ma PX. Antibacterial anti-oxidant electroactive injectable hydrogel as self-healing wound dressing with hemostasis and adhesiveness for cutaneous wound healing. Biomaterials. 2017;122:34–47.
Sarasam AR, Krishnaswamy RK, Madihally SV. Blending chitosan with polycaprolactone: effects on physicochemical and antibacterial properties. Biomacromolecules. 2006;7:1131–8.
Yang J, Li M, Wang Y, Wu H, Zhen T, Xiong L, et al. Double cross-linked chitosan composite films developed with oxidized tannic acid and ferric ions exhibit high strength and excellent water resistance. Biomacromolecules. 2019;20:801–12.
Kwon S, Park JH, Chung H, Kwon IC, Jeong SY, Kim IS. Physicochemical characteristics of self-assembled nanoparticles based on glycol chitosan bearing 5β-cholanic acid. Langmuir. 2003;19:10188–93.
Razi MA, Wakabayashi R, Goto M, Kamiya N. Self-assembled reduced albumin and glycol chitosan nanoparticles for paclitaxel delivery. Langmuir. 2019;35:2610–8.
Sashiwa H, Yamamori N, Ichinose Y, Sunamoto J, Aiba S. Chemical modification of chitosan 17. Macromol Biosci. 2003;3:231–3.
Jayakumar R, Prabaharan M, Nair SV, Tokura S, Tamura H, Selvamurugan N. Novel carboxymethyl derivatives of chitin and chitosan materials and their biomedical applications. Prog Mater Sci. 2010;55:675–709.
Kim CH, Choi JW, Chun HJ, Choi KS. Synthesis of chitosan derivatives with quaternary ammonium salt and their antibacterial activity. Polym Bull. 1996;38:387–93.
Rúnarsson ÖV, Holappa J, Nevalainen T, Hjálmarsdóttir M, Järvinen T, Loftsson T, et al. Antibacterial activity of methylated chitosan and chitooligomer derivatives: Synthesis and structure activity relationships. Eur Polym J. 2007;43:2660–71.
Kadokawa J, Shimohigoshi R, Yamashita K, Yamamoto K. Synthesis of chitin and chitosan stereoisomers by thermostable α-glucan phosphorylase-catalyzed enzymatic polymerization of α-d-glucosamine 1-phosphate. Org Biomol Chem. 2015;13:4336–43.
Li J, Zivanvic S, Davidson PM, Kit K. Characterization and comparison of chitosan/PVP and chitosan/PEO blend films. Carbohydr Polym. 2010;79:786–91.
You J, Xie S, Cao J, Ge H, Xu M, Zhang L, et al. Quaternized chitosan/poly(acrylic acid) polyelectrolyte complex hydrogels with tough, self-recovery, and tunable mechanical properties. Macromolecules. 2016;49:1049–59.
Wan Y, Wu H, Yu A, Wen D. Biodegradable polylactide/chitosan blend membrances. Biomacromolecules. 2006;7:1362.
Tempelaar S, Mespouille L, Coulembier O, Dubois P, Dove AP. Synthesis and post-polymerisation modifications of aliphatic poly(carbonate)s prepared by ring-opening polymerization. R Soc Chem. 2013;42:1312–36.
Ajiro H, Takahashi Y, Akashi M. Thermosensitive biodegradable homopolymer of trimethylene carbonate derivative at body temperature. Macromolecules. 2012;45:2668–74.
Nederberg F, Zhang Y, Tan JPK, Xu K, Wang H, Yang C, et al. Biodegradable nanostructures with selective lysis of microbial membranes. Nat Chem. 2011;3:409–14.
Zhao C, Shao L, Lu J, Deng X, Wu Y. Tumor acidity-induced sheddable polyethylenimine-poly(trimethylene carbonate)/DNA/polyethylene glycol-2,3-dimethylmaleicanhydride ternary complex for efficient and safe gene delivery. ACS Appl Mater Inter. 2016;8:6400–10.
Fukushima K. Poly(trimethylene carbonate)-based polymers engineered for biodegradable functional biomaterials. Biomater Sci 2016;4:9–24.
Chanthaset N, Ajiro H. Preparation of thermosensitive biodegradable hydrogel using poly(5-[2-{2-(2-methoxyethoxy)ethyoxy}-ethoxymethyl]−5-methyl-1,3-dioxa-2-one) derivatives. Materialia.2019;5:100178
Liu D, Lia H, Zhoua G, Yuana M, Qin Y. Biodegradable poly(lactic‐acid)/poly(trimethylene‐carbonate)/laponite composite film: development and application to the packaging of mushrooms (Agaricus bisporus). Polym Adv Technol. 2015;26:1600–7.
Choi J, Kwak SY. Synthesis and characterization of hyperbranched poly(ε-caprolactone)s having different lengths of homologous backbone segments. Macromolecules. 2003;36:8630–7.
Ariga T, Tanaka T, Endo T. Alkyl halide‐initiated cationic polymerization of cyclic carbonate. J Polym Sci Part A: Polym Chem. 1993;31:581–4.
Mady MF, Charoensumran P, Ajiro H, Kelland MA. Synthesis and characterization of modified aliphatic polycarbonates as environmentally friendly oilfield scale inhibitors. Energ Fuels. 2018;32:6746–55.
Al-Azemi TF, Harmon JP, Bisht KS. Enzyme-catalyzed ring-opening copolymerization of 5-methyl-5-benzyloxycarbonyl-1,3-dioxan-2-one (MBC) with trimethylene carbonate (TMC): synthesis and characterization. Biomacromolecules. 2000;1:493–500.
Sébastien F, Stéphane G, Copinet A, Coma V. Novel biodegradable films made from chitosan and poly(lactic acid) with antifungal properties against mycotoxinogen strains. Carbohydr Polym. 2006;65:185–93.
Zhanga J, Tana W, Zhang Z, Song Y, Li Q, Dong F. Guo Z. Int J Biol Macromol. 2018;109:1061.
Cazóna P, Velázqueza G, Vázquez M. Characterization of bacterial cellulose films combined with chitosan and polyvinyl alcohol: Evaluation of mechanical and barrier properties. Carbohydr Polym. 2019;216:72–85.
Nobuoka H, Ajiro H. Development of ester free type poly(trimethylene carbonate) derivatives with pendant fluoroaromatic groups. Macromol Chem Phys. 2019;220:1900051.
Kulig D, Zimoch-Korzycka A, Jarmoluk A, Marycz K. Study on alginate–chitosan complex formed with different polymers ratio. Polymers. 2016;8:167.
Cao J, Li J, Chen Y, Zhang L, Zhou J. Dual physical crosslinking strategy to construct moldable hydrogels with ultrahigh strength and toughness. Adv Funct Mater. 2018;28:1800739.
Mi FL, Wu YY, Lin YH, Sonaje K, Ho YC, Chen CT, et al. Oral delivery of Ppeptide drugs using nanoparticles self-assembled by poly(γ-glutamic acid) and a chitosan derivative functionalized by trimethylation. Bioconjugate Chem. 2008;19:1248–55.
Alhwaige AA, Ishida H, Qutubuddin S. Poly(benzoxazine-f-chitosan) films: The role of aldehyde neighboring groups on chemical interaction of benzoxazine precursors with chitosan. Carbohydr Polym. 2019;209:122–9.
Neto RJG, Genevro GM, Paulo LA, Lopes PS, Moraes MA, Beppu MM. Characterization and in vitro evaluation of chitosan/konjac glucomannan bilayer film as a wound dressing. Carbohydr Polym. 2019;212:59–66.
Chen M, Runge T, Wang L, Li R, Feng J, Shu XL, et al. Hydrogen bonding impact on chitosan plasticization. Carbohydr Polym. 2018;200:115–21.
Acknowledgements
This work is partly supported by the Bilateral program: Joint Research Thailand-Japan (JSPS-NRCT), Grant Number JPJSBP120189206. This work was supported by JSPS KAKENHI Grant-in-Aid for Scientific Research (B), Grant Number JP20H02799.
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Irikura, K., Ekapakul, N., Choochottiros, C. et al. Fabrication of flexible blend films using a chitosan derivative and poly(trimethylene carbonate). Polym J 53, 823–833 (2021). https://doi.org/10.1038/s41428-021-00470-6
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DOI: https://doi.org/10.1038/s41428-021-00470-6