Furan–chitosan hydrogels based on click chemistry

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• 作者：Marcelino Montiel-Herrera ; Alessandro Gandini…
• 关键词：Chitosan ; Furan ; Click chemistry ; Diels–Alder ; Hydrogels ; Maleimide
• 刊名：Iranian Polymer Journal
• 出版年：2015
• 出版时间：May 2015
• 年：2015
• 卷：24
• 期：5
• 页码：349-357
• 全文大小：599 KB
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• 作者单位：Marcelino Montiel-Herrera (1)
  Alessandro Gandini (2)
  Francisco M. Goycoolea (3) (5)
  Neil E. Jacobsen (4)
  Jaime Lizardi-Mendoza (5)
  Maricarmen T. Recillas-Mota (1)
  Waldo M. Argüelles-Monal (1)
  
  1. Laboratorio de Polímeros Naturales, Centro de Investigación en Alimentación y Desarrollo A. C., Carretera al Varadero Nacional km 6.6, Col. Las Playitas, 85480, Guaymas, Sonora, Mexico
  2. Materials Engineering Department, Engineering School of S?o Carlos, University of S?o Paulo, S?o Carlos, 13566-590, Brazil
  3. Institut für Biologie und Biotechnologie der Pflanzen, Westf?lische Wilhelms-Universt?t Münster, Hindernburgplatz 55, 48143, Münster, Germany
  5. Lab. de Biopolímeros, Centro de Investigación en Alimentación y Desarrollo A.C., Carretera a la Victoria km 0.6, Ejido La Victoria, 83000, Hermosillo, Sonora, Mexico
  4. Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd, Tucson, AZ, 85721, USA
  
• 刊物主题：Polymer Sciences; Ceramics, Glass, Composites, Natural Methods;
• 出版者：Springer Berlin Heidelberg
• ISSN：1735-5265

文摘

The modification of polymers by click chemistry has increased abruptly over the past years. In this study, furan groups were attached onto chitosan chain via reaction of 6-azido-6-deoxy chitosan and furfuryl propargyl ether. With this purpose, 6-azido-6-deoxy chitosan was synthesized by bromination and the subsequent nucleophilic substitution with sodium azide on the C6 hydroxyl groups of a previously amino-protected N-phthaloyl chitosan. Then, 6-azido-6-deoxy chitosan was reacted with furfuryl propargyl ether by the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction, resulting in an o-substituted furan–chitosan derivative with a degree of substitution of 10?%. The structure of all derivatives was analyzed and confirmed by means of infrared and nuclear magnetic resonance spectroscopies. Clicked chitosan with furan side groups was cross-linked with a bismaleimide to produce a polymer network via Diels–Alder reaction at 75?°C. The system presented a sol–gel transition with some syneresis. The gelation process was monitored by the evolution of the viscoelastic properties of the reaction mixture. The generated chitosan–furan–maleimide polymer network exhibited the typical pattern of a soft polymer hydrogel, in which both moduli were almost frequency independent with values lower than 10?Pa. These weak mechanical properties were interpreted as a consequence of the polymer degradation, which took place during the N-phthaloyl deprotection procedure.