مروری بر پلی‌یورتان‌های دارای کیتوسان: سنتز، خواص و کاربردها

نوع مقاله : مروری

نویسندگان

اصفهان، دانشگاه اصفهان، دانشکده شیمی، کد پستی 73441-81746

چکیده

امروزه توجه به پلی‌یورتان‌ها به‌دلیل‌ سنتز آسان، مواد اولیه در دسترس، خواص مکانیکی مطلوب، زیست‌سازگاری و امکان ارائه محصولات متفاوت به‌شکل پلی‌یورتان‌های آب‌پایه، اسفنج، هیدروژل و چسب در حال افزایش است. کیتوسان پلیمری طبیعی بوده که از استیل‌زدایی کیتین استخراج می‌شود و دارای واحد‌های گلوکوزآمین و N-استیل گلوکوزآمین است. این پلیمر طبیعی غیرسمی، خواص بسیار مفیدی نظیر فعالیت ضدمیکروبی، زیست‌سازگاری، زیست‌تخریب‌پذیری و آثار ترمیم و بازسازی بافت را دارد. از ضعف‌های کیتوسان می‌توان به حل‌پذیری و فرایندپذیری ضعیف به‌دلیل تعدد پیوندهای هیدروژنی درون و بین‌مولکولی قوی آن اشاره کرد. از این‌رو، به‌طور عمده از کیتوسان به‌صورت اصلاح‌شده یا در ترکیب با سایر پلیمر‌ها در کاربرد‌های گوناگون استفاده شده‌ است. ترکیب پلیمر‌های سنتزی با پلیمر‌های طبیعی از اهمیت ویژه‌ای برخوردار است، زیرا پلیمرهای طبیعی مانند کیتوسان می‌توانند برخی از خواص مانند زیست‌سازگاری، زیست‌تخریب‌پذیری، سمیت کم، زنده‌مانی یاخته‌ای زیاد و رشد ذاتی بافت را نشان دهند، در حالی که پلیمرهای سنتزی ویژگی‌های دیگری مانند فرایندپذیری مطلوب، خواص فیزیکی و مکانیکی و پایداری شیمیایی و گرمایی مناسب را دارند. اخیراً از کیتوسان به‌منظور بهبود در خواص مکانیکی، پایداری گرمایی، زیست‌تخریب‌پذیری، خاصیت ضدمیکروبی و فعالیت زیستی در ترکیب با پلی‌یورتان‌ها استفاده شده است. طی این مطالعات، محصولاتی گوناگون مانند کامپوزیت، الاستومر، الیاف، اسفنج، داربست و هیدروژل برای کاربرد‌های مختلف تهیه شده است. در این مقاله،‌ پلی‌یورتان‌های دارای کیتوسان و روش‌های سنتز آن‌ها برای کاربردهای مختلف مرور شده است. محصولات تهیه‌شده در این مطالعات برای کاربرد‌های متنوع نظیر اصلاح پارچه‌ها، تهیه پوشش‌های ضدباکتری، زخم‌پوش‌ها، داربست‌های مهندسی بافت، ، الیاف، هیدروژل‌ و اسفنج پیشنهاد شده است.

کلیدواژه‌ها


عنوان مقاله [English]

A Review on Chitosan-Containing Polyurethanes: Synthesis, Properties and Applications

نویسندگان [English]

  • Abbas Mohammadi
  • Zahra Shahsanaei Goneirani
  • Alireza Fatahi
Department of Organic Chemistry and Polymer, Faculty of Chemisty, University of Isfahan, Postal Code 81746-73441, Isfahan, Iran
چکیده [English]

Today, the specialists’ attention on polyurethanes is increasing day by day due to easy synthesis, available raw materials, favorable mechanical properties, biocompatibility, and the possibility of providing different products, such as water-based polyurethanes, foams, hydrogels and glues. Chitosan is a natural polymer that is extracted from the deacetylation of chitin and contains glucosamine and N-acetyl glucosamine units. This non-toxic natural polymer has very useful properties such as antimicrobial activity, biocompatibility, biodegradability, and tissue repair and regeneration effects. One of the weaknesses of chitosan is its poor solubility and processability due to its strong intra- and intermolecular hydrogen bonding. Therefore, chitosan has been used mainly in modified form or in combination with other polymers in various applications. The combination of synthetic polymers with natural polymers is of particular importance because natural polymers such as chitosan can show some properties such as biocompatibility, biodegradability, low toxicity, high cell viability, and internal tissue growth; while the synthetic polymers have other characteristics such as favorable processing, mechanical and physical properties, and appropriate chemical and thermal stability. Recently, chitosan has been used in combination with polyurethanes to improve its mechanical properties, thermal stability, biodegradability, antimicrobial properties and biological activity. During these studies, products in various forms such as composite, elastomer, fiber, foam, scaffold, and hydrogel have been prepared for different applications. In this review, polyurethanes containing chitosan and their synthesis methods for various applications are discussed. The products prepared in these studies have been suggested for various applications such as antibacterial coating, wound dressing, tissue engineering scaffold, fabric modification, fibers, hydrogels and foams.

کلیدواژه‌ها [English]

  • polyurethane
  • Chitosan
  • synthesis
  • Properties
  • application
  1. Petrović Z.S., Cho Y.J., Javni I., Magonov S., Yerina N., Schaefer D.W., and Waddon A., Effect of Silica Nanoparticles on Morphology of Segmented Polyurethanes, Polymer, 45, 4285-4295, 2004.
  2. Domb A.J., Beyth N., and Farah S., Quaternary Ammonium Antimicrobial Polymers, MRS Online Proceedings Library (OPL), 1569, 97-107, 2013.
  3. Teo L.S., Chen C.Y., and Kuo J.F., Fourier Transform Infrared Spectroscopy Study on Effects of Temperature on Hydrogen Bonding in Amine-Containing Polyurethanes and Poly(urethane-urea)s, Macromolecules, 30, 1793-1799, 1997.
  4. Hepburn C., Polyurethane Elastomers, Springer Science and Business Media, 2nd ed., London and New Yor, 2, 6-29, 2012.
  5. Hood M.A., Wang B., Sands J.M., La Scala J.J., Beyer F.L., and Li C.Y., Morphology Control of Segmented Polyurethanes by Crystallization of Hard and Soft Segments, Polymer, 51, 2191-2198, 2010.
  6. Mohammadi A., Barikani M., and Lakouraj M.M.,
    Biocompatible Polyurethane/Thiacalix[4]arenes Functionalized Fe3O4 Magnetic Nanocomposites: Synthesis and Properties, Sci. Eng., C, 66, 106-118, 2016.
  7. Mohammadi A., Barikani M., and Barmar M., Effect of Polyol Structure on the Properties of the Resultant Magnetic Polyurethane Elastomer Nanocomposites, Adv. Technol., 24, 978-985, 2013.
  8. Bankoti K., Rameshbabu A.P., Datta S., Maity P.P., Goswami P., Datta P., and Dhara S., Accelerated Healing of Full Thickness Dermal Wounds by Macroporous Waterborne Polyurethane-Chitosan Hydrogel Scaffolds, Sci. Eng., C, 81, 133-143, 2017.
  9. Daemi H., Barikani M., and Barmar M., Compatible Compositions Based on Aqueous Polyurethane Dispersions and Sodium Alginate, Polym., 92, 490-496, 2013.
  10. Mohammadi A., Lakouraj M.M., and Barikani M., Synthesis and Investigation of Properties of Thiacalix[4]arene-Based Polyurethane Elastomers, Int., 64, 421-429, 2015.
  11. Dutta A.S., Polyurethane Foam Chemistry, In Recycling of Polyurethane Foams, William Andrew, 17-27, 2018.
  12. Bil M., The Effect of Chitosan Form on the Shape Memory Properties of Polyurethane Based Composites, Lett., 284, 129007, 2021.
  13. Silva S.S., Menezes S.M.C., and Garcia R.B., Synthesis and Characterization of Polyurethane-g-Chitosan, Polym., 39, 1515-1519, 2003.‏
  14. Elieh-Ali-Komi D. and Hamblin M.R., Chitin and Chitosan: Production and Application of Versatile Biomedical Nanomaterials, J. Adv. Res., 4, 411, 2016.
  15. Chitin, Chitosan, Oligosaccharides and Their Derivatives: Biological Activities and Applications, Kim S.K. (Ed.), CRC, Boca Raton, 2010.
  16. Yao K., Li J., Yao F., and Yin Y., Chitosan-Based Hydrogels: Functions and Applications, Taylor and Francis Group, CRC, 1st. ed., 1-39, 2012.
  17. Younes I. and Rinaudo M., Chitin and Chitosan Preparation from Marine Sources. Structure, Properties and Applications, Marine Drugs, 13, 1133-1174, 2015.
  18. Kou S.G., Peters L.M., and Mucalo M.R., Chitosan: A Review of Sources and Preparation Methods, J. Biolog. Macromol., 169, 85-94, 2021.
  19. Zhang S., Hydroxyapatite Coatings for Biomedical Applications, Taylor and Francis Group, CRC, 1st ed., 39-40, 2013.
  20. Mahanta A.K., Mittal V., Singh N., Dash D., Malik S., Kumar M., and Maiti P., Polyurethane-grafted Chitosan as New Biomaterials for Controlled Drug Delivery, Macromolecules, 48, 2654-2666, 2015.
  21. Kara F., Aksoy E.A., Yuksekdag Z., Hasirci N., and Aksoy S., Synthesis and Surface Modification of Polyurethanes with Chitosan for Antibacterial Properties, Polym., 112, 39-47, 2014.
  22. Young D.H. and Kauss H., Release of Calcium from Suspension-Cultured Glycine Max Cells by Chitosan, Other Polycations, and Polyamines in Relation to Effects on Membrane Permeability, Plant Physiol., 73, 698-702, 1983.
  23. Sahariah P. and Másson M., Antimicrobial Chitosan and Chitosan Derivatives: A Review of the Structure–Activity Relationship, Biomacromolecules, 18, 3846-3868, 2017.
  24. Chung Y.C. and Chen C.Y., Antibacterial Characteristics and Activity of Acid-Soluble Chitosan, Technol., 99, 2806-2814, 2008.
  25. Snyman D., Hamman J.H., Kotze J.S., Rollings J.E., and Kotze A.F., The Relationship between the Absolute Molecular Weight and the Degree of Quaternisation of N-Trimethyl Chitosan Chloride, Polym., 50, 145-150, 2002.
  26. Bakshi P.S., Selvakumar D., Kadirvelu K., and Kumar N.S., Chitosan as an Environment Friendly Biomaterial–A Review on Recent Modifications and Applications, J. Biolog. Macromol., 150, 1072-1083, 2020.
  27. Electroactive Polymers: Materials and Devices, Hashmi S.A., Chandra A., Singh R.K., Chandra A., and Chandra S. (Eds.), Allied, India, 5, 3-5, 2015.
  28. Zia K.M., Zuber M., Bhatti I.A., Barikani M., and Sheikh M.A., Evaluation of Biocompatibility and Mechanical Behavior of Polyurethane Elastomers Based on Chitin/1,4-Butane Diol Blends, J. Biolog. Macromol., 44, 18-22, 2009.
  29. Usman A., Zia K.M., Zuber M., Tabasum S., Rehman S., and Zia F., Chitin and Chitosan Based Polyurethanes: A Review of Recent Advances and Prospective Biomedical Applications, J. Biolog. Macromol., 86, 630-645, 2016.
  30. Zia K.M., Anjum S., Zuber M., Mujahid M., and Jamil T., Synthesis and Molecular Characterization of Chitosan Based Polyurethane Elastomers Using Aromatic Diisocyanate, J. Biolog. Macromol., 66, 26-32, 2014.
  31. Zhang S., Liu X., Jin X., Li H., Sun J., and Gu X., The Novel Application of Chitosan: Effects of Cross-Linked Chitosan on the Fire Performance of Thermoplastic Polyurethane, Polym., 189, 313-321, 2018.
  32. Indumathi M.P. and Rajarajeswari G.R., Mahua Oil-Based Polyurethane/Chitosan/Nano ZnO Composite Films for Biodegradable Food Packaging Applications, J. Biolog. Macromol., 124, 163-174, 2019.
  33. Wang R., Song X., Xiang T., Liu Q., Su B., Zhao W., and Zhao C., Mussel-Inspired Chitosan-Polyurethane Coatings for Improving the Antifouling and Antibacterial Properties of Polyethersulfone Membranes, Polym., 168, 310-319, 2017.
  34. Najafabadi S.A.A., Mohammadi A., and Kharazi A.Z., Polyurethane Nanocomposite Impregnated with Chitosan-Modified Graphene Oxide as a Potential Antibacterial Wound Dressing, Sci. Eng., C, 115, 110899, 2020.‏
  35. Mohammadi A., Lakouraj M.M., and Barikani M., Waterborne Polyurethanes Based on Macrocyclic Thiacalix[4]arenes as Novel Emulsifiers: Synthesis, Characterization and Anti-Corrosion Properties, RSC Adv., 6, 87539-87554, 2016.
  36. Kim B.K., Aqueous Polyurethane Dispersions, Colloid Polym. Sci., 274, 599-611, 1996.
  37. Liu N., Zhao Y., Kang M., Wang J., Wang X., Feng Y., and Li Q., The Effects of the Molecular Weight and Structure of Polycarbonatediols on the Properties of Waterborne Polyurethanes, Org. Coat., 82, 46-56, 2015.
  38. Honarkar H., Barmar M., Barikani M., and Shokrollahi P., Synthesis and Characterization of Polyhedral Oligomeric Silsesquioxane-Based Waterborne Polyurethane Nano- composites, Korean J. Chem. Eng., 33, 319-329, 2016.
  39. Mohammadi A., Doctorsafaei A.H., Burujeny S.B., Rudbari H.A., Kordestani N., and Najafabadi S.A.A., Silver (I) Complex with a Schiff Base Ligand Extended Waterborne Polyurethane: A Developed Strategy to Obtain a Highly Stable Antibacterial Dispersion Impregnated with in Situ Formed Silver Nanoparticles, Eng. J., 381, 122776, 2020.
  40. Xia Y., Zhang Z., Kessler M.R., Brehm-Stecher B., and Larock R.C., Antibacterial Soybean-Oil-Based Cationic Polyurethane Coatings Prepared from Different Amino Polyols, ChemSusChem, 5, 2221-2227, 2012.
  41. Mohammadi A., Hosseini D., Isfahani A.P., Dehghani Z., and Shams E., Waterborne Polyurethane Nanocomposite Incorporated with Phytic Acid Intercalated Layered Double Hydroxides: A Highly Stable Aqueous Dispersion with Desired Corrosion Protection Capability, Adv. Technol., 32, 4014-4028, 2021.
  42. Zo S., Choi S., Kim H., Shin E., and Han S., Synthesis and Characterization of Carboxymethyl Chitosan Scaffolds Grafted with Waterborne Polyurethane, Nanosci. Nanotechnol., 20, 5014-5018, 2020.
  43. Cakić S.M., Ristić I.S., Marinović-Cincović M., and Špírková M., The Effects of the Structure and Molecular Weight of the Macrodiol on the Properties Polyurethane Anionic Adhesives, J. Adhes. Adhes., 41, 132-139, 2013.
  44. Fu H., Wang Y., Chen W., and Xiao J., Reinforcement of Waterborne Polyurethane with Chitosan-Modified Halloysite Nanotubes, Surface Sci., 346, 372-378, 2015.
  45. Barni A. and Levi M., Aqueous Polyurethane Dispersions: A Comparative Study of Polymerization Processes, Appl. Polym. Sci., 88, 716-723, 2003.
  46. Barikani M., Valipour Ebrahimi M., and Seyed Mohaghegh S.M., Preparation and Characterization of Aqueous Polyurethane Dispersions Containing Ionic Centers, Appl. Polym. Sci., 104, 3931-3937, 2007.
  47. Jayakumar R., Nanjundan S., and Prabaharan M., Developments in Metal-Containing Polyurethanes, Copolyurethanes and Polyurethane Ionomers, Macromol. Sci., Part C: Polym, Rev., 45, 231-261, 2005.
  48. Arshad N., Zia K.M., Jabeen F., Anjum M.N., Akram N., and Zuber M., Synthesis, Characterization of Novel Chitosan Based Water Dispersible Polyurethanes and Their Potential Deployment as Antibacterial Textile Finish, J. Biolog. Macromol., 111, 485-492, 2018.
  49. Xu D., Wu K., Zhang Q., Hu H., Xi K., Chen Q., and Jia X., Synthesis and Biocompatibility of Anionic Polyurethane Nanoparticles Coated with Adsorbed Chitosan, Polymer, 51, 1926-1933, 2010.
  50. Ghosh B., Gogoi S., Thakur S., and Karak N., Bio-Based Waterborne Polyurethane/Carbon Dot Nanocomposite as a Surface Coating Material, Org. Coat., 90, 324-330, 2016.‏
  51. Zhang W., Deng H., Xia L., Shen L., Zhang C., Lu Q., and Sun S., Semi-Interpenetrating Polymer Networks Prepared from Castor Oil-Based Waterborne Polyurethanes and Carboxymethyl Chitosan, Polym., 256, 117507, 2021.
  52. Song M., Zhou M., Hu H., and Fu H., Research on WPU-RGO/ATP-Fe3O4/Chitosan Composites with Excellent Electrical and Magnetic Properties, Adv. Technol., 31, 1164-1171, 2020.
  53. Mo Q., Li W., Yang H., Gu F., Chen Q., and Yang R., Water Resistance and Corrosion Protection Properties of Waterborne Polyurethane Coating Enhanced by Montmorillonite Modified with Ce3+, Org. Coat., 136, 105213, 2019.
  54. Greiner A. and Wendorff J.H., Electrospinning: A Fascinating Method for the Preparation of Ultrathin Fibers, Chem. Int. Ed., 46, 5670-5703, 2007.‏
  55. Dzenis Y., Spinning Continuous Fibers for Nanotechnology, Science, 304, 1917-1919, 2004.
  56. Elsabee M.Z., Naguib H.F., and Morsi R.E., Chitosan Based Nanofibers, Review, Sci. Eng., C, 32, 1711-1726, 2012.
  57. Schiffman J.D. and Schauer C.L., A Review: Electrospinning of Biopolymer Nanofibers and Their Applications, Rev., 48, 317-352, 2008.
  58. Klossner R.R., Queen H.A., Coughlin A.J., and Krause W.E., Correlation of Chitosan’s Rheological Properties and Its Ability to Electrospin, Biomacromolecules, 9, 2947-2953, 2008.
  59. Gu B.K., Park S.J., Kim M.S., Kang C.M., Kim J.I., and Kim C.H., Fabrication of Sonicated Chitosan Nanofiber Mat with Enlarged Porosity for Use as Hemostatic Materials, Polym., 97, 65-73, 2013.
  60. Ahmadi P., Nazeri N., Derakhshan M.A., and Ghanbari H., Preparation and Characterization of Polyurethane/Chitosan/CNT Nanofibrous Scaffold for Cardiac Tissue Engineering, J. Biolog. Macromol., 180, 590-598, 2021.
  61. Mohraz M.H., Golbabaei F., Yu I.J., Mansournia M.A., Zadeh A.S., and Dehghan S.F., Preparation and Optimization of Multifunctional Electrospun Polyurethane/Chitosan Nanofibers for Air Pollution Control Applications, J. Env. Sci. Technol., 16, 681-694, 2019.
  62. Shrestha S., Shrestha B.K., Ko S.W., Kandel R., Park C.H., and Kim C.S., Engineered Cellular Microenvironments from Functionalized Multiwalled Carbon Nanotubes Integrating Zein/Chitosan@Polyurethane for Bone Cell Regeneration, Polym., 251, 117035, 2021.
  63. Lee S.J., Heo D.N., Moon J.H., Park H.N., Ko W.K., Bae M.S., and Kwon I.K., Chitosan/Polyurethane Blended Fiber Sheets Containing Silver Sulfadiazine for Use as an Antimicrobial Wound Dressing, Nanosci. Nanotechnol., 14, 7488-7494, 2014.
  64. Khan M.S.J., Kamal T., Ali F., Asiri A.M., and Khan S.B., Chitosan-Coated Polyurethane Sponge Supported Metal Nanoparticles for Catalytic Reduction of Organic Pollutants, J. Biolog. Macromol., 132, 772-783, 2019.
  65. Qin H. and Wang K., Study on Preparation and Performance of PEG-Based Polyurethane Foams Modified by the Chitosan with Different Molecular Weight, J. Biolog. Macromol., 140, 877-885, 2019.
  66. Mohammadi A., Lakouraj M.M., and Barikani M., Preparation and Characterization of p-tert-Butyl Thiacalix[4]arene Imbedded Flexible Polyurethane Foam: An Efficient Novel Cationic Dye Adsorbent, Funct. Polym., 83, 14-23, 2014.
  67. Dmitrienko S.G. and Zolotov Y.A., Polyurethane Foams in Chemical Analysis: Sorption of Various Substances and Its Analytical Applications, Russ Chem. Rev., 71, 159-174, 2002.
  68. Abrishamkar S., Mohammadi A., De La Vega J., Wang D.Y., and Kalali E.N., Layer-by-Layer Assembly of Calixarene Modified GO and LDH Nanostructures on Flame Retardancy, Smoke Suppression, and Dye Adsorption Behavior of Flexible Polyurethane Foams, Degrad. Stab., 207, 110242, 2023.
  69. Ashida K., Polyurethane and Related Foams: Chemistry and Technology, CRC, Boca Raton, 1st ed., 2006.
  70. Mohammadi A., Wang D.Y., Hosseini A.S., and De La Vega J., Effect of Intercalation of Layered Double Hydroxides with Sulfonate-Containing Calix[4]arenes on the Flame Retardancy of Castor Oil-Based Flexible Polyurethane Foams, Test., 79, 106055, 2019.
  71. Lin B., Yuen A.C.Y., Li A., Zhang Y., Chen T.B.Y., Yu B., and Wang C.H., MXene/Chitosan Nanocoating for Flexible Polyurethane Foam towards Remarkable Fire Hazards Reductions, Hazard. Mater., 381, 120952, 2020
  72. Qin J., Qiu F., Rong X., Yan J., Zhao H., and Yang D., Adsorption Behavior of Crystal Violet from Aqueous Solutions with Chitosan–Graphite Oxide Modified Polyurethane as an Adsorbent, Appl. Polym. Sci., 132, 41828, 2015.
  73. da Rosa Schio R., da Rosa B.C., Gonçalves J.O., Pinto L.A., Mallmann E.S. and Dotto G.L., Synthesis of a Bio–Based Polyurethane/Chitosan Composite Foam Using Ricinoleic Acid for the Adsorption of Food Red 17 Dye, J. Biolog. Macromol., 121, 373-380, 2019.
  74. Ren L., Tang Z., Du J., Chen L., and Qiang T., Recyclable Polyurethane Foam Loaded with Carboxymethyl Chitosan for Adsorption of Methylene Blue, Hazard. Mater., 417, 126130, 2021.‏
  75. Viezzer C., Mazzuca R., Machado D.C., de Camargo Forte M.M., and Ribelles J.L.G., A New Waterborne Chitosan-Based Polyurethane Hydrogel as a Vehicle to Transplant Bone Marrow Mesenchymal Cells Improved Wound Healing of Ulcers in a Diabetic Rat Model, Polym., 231, 115734, 2020.
  76. Lin T.W. and Hsu S.H., Self-Healing Hydrogels and Cryogels from Biodegradable Polyurethane Nanoparticle Crosslinked Chitosan, Sci., 7, 1901388, 2020.
  77. Zhang M., Yang M., Woo M.W., Li Y., Han W., and Dang X., High-Mechanical Strength Carboxymethyl Chitosan-Based Hydrogel Film for Antibacterial Wound Dressing, Polym., 256, 117590, 2021.
  78. Atef El-Sayed A., El Gabry L.K., and Allam O.G., Application of Prepared Waterborne Polyurethane Extended with Chitosan to Impart Antibacterial Properties to Acrylic Fabrics, Mater. Sci., Mater. Med., 21, 507-514, 2010.
  79. Naz F., Zuber M., Zia K.M., Salman M., Chakraborty J., Nath I., and Verpoort F., Synthesis and Characterization of Chitosan-Based Waterborne Polyurethane for Textile Finishes, Polym., 200, 54-62, 2018.
  80. Shi J., Han X., and Kelu Y., A Novel Bio-Functional Finishing Agent for Wool Based on Waterborne Polyurethane Mixed with Chitosan, Res. J., 84, 1174-1182, 2014.
  81. Lee D.I., Kim S.H., and Lee D.S., Synthesis of Self-Healing Waterborne Polyurethane Systems Chain Extended with Chitosan, Polymers, 11, 503, 2019.
  82. Shaabani A. and Sedghi R., Preparation of Chitosan Biguanidine/PANI-Containing Self-Healing Semi-Conductive Waterborne Scaffolds for Bone Tissue Engineering, Polym., 264, 118045, 2021.
  83. Xu J., Fu C.Y., Tsai Y.L., Wong C.W., and Hsu S.H., Thermoresponsive and Conductive Chitosan-Polyurethane Biocompatible Thin Films with Potential Coating Application, Polymers, 13, 326, 2021.
  84. Liu Y., Zou Y., Wang J., Wang S., and Liu X., A Novel Cationic Waterborne Polyurethane Coating Modified by Chitosan Biguanide Hydrochloride with Application Potential in Medical Catheters, Appl. Polym. Sci., 138, 50290, 2021.
  85. Xie C., Jia Y., Xue M., Yin Z., Luo Y., Hong Z., and Liu W., Anti-Corrosion and Self-Healing Behaviors of Waterborne Polyurethane Composite Coatings Enhanced via Chitosan-Modified Graphene Oxide and Phosphate Intercalated Hydrotalcite, Org. Coat., 168, 106881, 2022.
  86. Yan K., Liu C., and Ma J., Dendritic Fibrous Nanosilica Loaded Chitosan for Improving Water Vapor Permeability and Antibacterial Properties of Waterborne Polyurethane Acrylate Membranes, Clean. Prod., 291, 125922, 2021.
  87. Feng Z., Zheng Y., Zhao L., Zhang Z., Sun Y., Qiao K., and He W., An Ultrasound-Controllable Release System Based on Waterborne Polyurethane/Chitosan Membrane for Implantable Enhanced Anticancer Therapy, Sci. Eng. C, 104, 109944, 2019.
  88. Alves P., Ferreira P., and Gil M.H., Biomedical Polyurethanes-Based Materials, Polyurethane: Properties, Structure and Applications, in Polymer Science and Technology, Nova Science, New York, 25-50, 2012.‏
  89. Han J., Chen B., Ye L., Zhang A.Y., Zhang J., and Feng Z.G., Synthesis and Characterization of Biodegradable Polyurethane Based on Poly(ε-caprolactone) and L-Lysine Ethyl Ester Diisocyanate, Mater. Sci. China, 3, 25-32, 2009.
  90. Krajewska B., Application of Chitin- and Chitosan-Based Materials for Enzyme Immobilizations: A Review, Enzyme Microb. Technol., 35, 126-139, 2004.
  91. Huang Y.J., Chou Y.N., Lin Y.J., Chen W.Y., Chen C.Y., and Lin H.R., Polyurethane Modified by Oxetane Grafted Chitosan as Bioadhesive, J. Polym. Mater. Polym. Biomater., 70, 1100-1114, 2021.