Optimization of chitosan adhesive properties by means of genipin crosslinking

References

• NF EN 204: 2016, Classification of Thermoplastic Wood Adhesives for Non-Structural Applications 2016.
   Google Scholar
• NF EN 205: 2016, Adhesives - Wood Adhesives for Non-Structural Applications - Determination of Tensile Shear Strength of Lap Joints 2016.
   Google Scholar
• Patel, A. K.; Michaud, P.; Petit, E.; de Baynast, H.; Grediac, M.; Mathias, J. D. Development of a Chitosan Based Adhesive. Application to Wood Bonding. J. Appl. Polym. Sci. 2012, 127(6), 5014–5021. DOI: 10.1002/app.38097.
   Web of Science ®Google Scholar
• Mati-Baouche, N.; Delattre, C.; de Baynast, H.; Grediac, M.; Mathias, J. D.; Ursu, A. V.; Desbrières, J.; Michaud, P. Alkyl-Chitosan-Based Adhesive: Water Resistance Improvement. Molecules. 2019, 24(10), 1987. DOI: 10.3390/molecules24101987.
   PubMed Web of Science ®Google Scholar
• Mati-Baouche, N.; Elchinger, P. H.; de Baynast, H.; Pierre, G.; Delattre, C.; Michaud, P. Chitosan as an Adhesive. Eur. Polym. J. 2014, 60, 198–212. DOI: 10.1016/j.eurpolymj.2014.09.008.
   Web of Science ®Google Scholar
• Jayakumar, R.; Menon, D.; Manzoor, K.; Nair, S. V.; Tamura, H. Biomedical Applications of Chitin and Chitosan Based Nanomaterials—A Short Review. Carbohyd. Polym. 2010, 82, 227–232. DOI: 10.1016/j.carbpol.2010.04.074.
   Web of Science ®Google Scholar
• Laroche, C.; Delattre, C.; Mati-Baouche, N.; Salah, R.; Ursu, A. V.; Moulti-Mati, F.; Michaud, P.; Pierre, G. Bioactivity of Chitosan and Its Derivatives. COC. 2018, 22(7), 641–667. DOI: 10.2174/1385272821666170811114145.
   Google Scholar
• Lehr, C.-M.; Bouwstra, J. A.; Schacht, E. H.; Junginger, H. E. In vitro Evaluation of Mucoadhesive Properties of Chitosan and Some Other Natural Polymers. Int. J. Pharmaceutics. 1992, 78(1–3), 43–48. DOI: 10.1016/0378-5173(92)90353-4.
   Web of Science ®Google Scholar
• Sorlier, P.; Denuzière, A.; Viton, C.; Domard, A. Relation Between the Degree of Acetylation and the Electrostatic Properties of Chitin and Chitosan. Biomacromolecules. 2001, 2, 765–772. DOI: 10.1021/bm015531+.
   PubMed Web of Science ®Google Scholar
• Yamada, K.; Chen, T.; Kumar, G.; Vesnovsky, O.; Topoleski, L. D. T.; Payne, G. F. Chitosan Based Water-Resistant Adhesive. Analogy to Mussel Glue. Biomacromolecules. 2000, 1(2), 252–258. DOI: 10.1021/bm0003009.
   PubMed Web of Science ®Google Scholar
• Umemura, K.; Inoue, A.; Kawai, S. Development of New Natural Polymer-Based Wood Adhesives I: Dry Bond Strength and Water Resistance of Konjac Glucomannan, Chitosan, and Their Composites. J. Wood Sci. 2003, 49(3), 221–226. DOI: 10.1007/s10086-002-0468-8.
   Web of Science ®Google Scholar
• Desbrières, J. Autoassociative Natural Polymer Derivatives: The Alkylchitosans. Rheological Behaviour and Temperature Stability. Polymer. 2004, 45, 3285–3295. DOI: 10.1016/j.polymer.2004.03.032.
   Web of Science ®Google Scholar
• Pellá, M. C. G.; Lima-Tenório, M. K.; Tenório-Neto, E. T.; Guilherme, M. R.; Muniz, E. C.; Rubira, A. F. Chitosan-Based Hydrogels: From Preparation to Biomedical Applications. Carbohydr. Polym. 2018, 196, 233–245. DOI: 10.1016/j.carbpol.2018.05.033.
   PubMed Web of Science ®Google Scholar
• Silvestre, J.; Delattre, C.; Michaud, P.; de Baynast, H. Optimization of Chitosan Properties with the Aim of a Water Resistant Adhesive Development. Polymers. 2021, 13, 4031. DOI: 10.3390/polym13224031.
   PubMed Web of Science ®Google Scholar
• Sung, H. W.; Chang, Y.; Chiu, C. T.; Chen, C. N.; Liang, H. C. Crosslinking Characteristics and Mechanical Properties of a Bovine Pericardium Fixed with a Naturally Occurring Crosslinking Agent. J. Biomed. Mater. Res. 1999, 47, 116–126. DOI: 10.1002/(SICI)1097-4636(199911)47:2<116:AID-JBM2>3.0.CO;2-J.
   PubMed Web of Science ®Google Scholar
• Tsai, C. C.; Huang, R. N.; Sung, H. W.; Liang, H. C. In vitro Evaluation of the Genotoxicity of a Naturally Occurring Crosslinking Agent (Genipin) for Biologic Tissue Fixation. J. Biomed. Mater. Res. 2000, 52, 58–65. DOI: 10.1002/1097-4636(200010)52:1<58:AID-JBM8>3.0.CO;2-0.
   PubMed Web of Science ®Google Scholar
• Muzzarelli, R. A. A. Genipin-Crosslinked Chitosan Hydrogels as Biomedical and Pharmaceutical Aids. Carbohydr. Polym. 2009, 77, 1–9. DOI: 10.1016/j.carbpol.2009.01.016.
   Web of Science ®Google Scholar
• Dimida, S.; Demitri, C.; De Benedictis, V. M.; Scalera, F.; Gervaso, F.; Sannino, A. Genipin-Cross-Linked Chitosan-Based Hydrogels: Reaction Kinetics and Structure-Related Characteristics. J. Appl. Polym. Sci. 2015, 132, n/a–n/a. DOI: 10.1002/app.42256.
   Web of Science ®Google Scholar
• Yang, Y. S.; Zhang, T.; Yu, S. C.; Ding, Y.; Zhang, L. Y.; Qiu, C.; Jin, D. Transformation of Geniposide into Genipin by Immobilized β-Glucosidase in a Two-Phase Aqueous-Organic System. Molecules. 2011, 16, 4295–4304. DOI: 10.3390/molecules16054295.
   PubMed Web of Science ®Google Scholar
• Wang, G.; Wu, S.; Rao, J.; Lü, L.; Xu, W.; Pang, J.; Liu, Z.; Wu, S.; Zhang, J. Genipin Inhibits Endothelial Exocytosis via Nitric Oxide in Cultured Human Umbilical Vein Endothelial Cells. Acta. Pharmacol. Sin. 2009, 30, 589–596. DOI: 10.1038/aps.2009.31.
   PubMed Web of Science ®Google Scholar
• Cao, H.; Feng, Q.; Xu, W.; Li, X.; Kang, Z.; Ren, Y.; Du, L. Genipin Induced Apoptosis Associated with Activation of the C-Jun NH2-Terminal Kinase and P53 Protein in HeLa Cells. Biol. Pharm. Bull. 2010, 33, 1343–1348. DOI: 10.1248/bpb.33.1343.
   PubMed Web of Science ®Google Scholar
• Lelono, R. A. A.; Tachibana, S.; Itoh, K. Isolation of Antifungal Compounds from Gardenia Jasminoides. Pak. J. Biol. Sci. 2009, 12, 949–956. DOI: 10.3923/pjbs.2009.949.956.
   PubMedGoogle Scholar
• Suzuki, Y.; Kondo, K.; Ikeda, Y.; Umemura, K. Antithrombotic Effect of Geniposide and Genipin in the Mouse Thrombosis Model. Planta. med. 2001, 67, 807–810. DOI: 10.1055/s-2001-18842.
   PubMed Web of Science ®Google Scholar
• Lee, J. H.; Lee, D. U.; Jeong, C. S. Gardenia Jasminoides Ellis Ethanol Extract and Its Constituents Reduce the Risks of Gastritis and Reverse Gastric Lesions in Rats. Food. Chem. Toxicol. 2009, 47, 1127–1131. DOI: 10.1016/j.fct.2009.01.037.
   PubMed Web of Science ®Google Scholar
• Zhang, C. Y.; Parton, L. E.; Ye, C. P.; Krauss, S.; Shen, R.; Lin, C. T.; Porco, J. A.; Lowell, B. B. Genipin Inhibits UCP2-Mediated Proton Leak and Acutely Reverses Obesity- and High Glucose-Induced β Cell Dysfunction in Isolated Pancreatic Islets. Cell Metab. 2006, 3, 417–427. DOI: 10.1016/j.cmet.2006.04.010.
   PubMed Web of Science ®Google Scholar
• Yamazaki, M.; Chiba, K.; Yoshikawa, C. Genipin Suppresses A23187-Induced Cytotoxicity in Neuro2a Cells. Biol. Pharm. Bull. 2009, 32, 1043–1046. DOI: 10.1248/bpb.32.1043.
   PubMed Web of Science ®Google Scholar
• Tian, J.-S.; Cui, Y.-L.; Hu, L.-M.; Gao, S.; Chi, W.; Dong, T.-J.; Liu, L.-P. Antidepressant-Like Effect of Genipin in Mice. Neurosci. Lett. 2010, 479, 236–239. DOI: 10.1016/j.neulet.2010.05.069.
   PubMed Web of Science ®Google Scholar
• Madhavan, K.; Belchenko, D.; Tan, W. Roles of Genipin Crosslinking and Biomolecule Conditioning in Collagen-Based Biopolymer: Potential for Vascular Media Regeneration. J. Biomed. Mater. Res. 2011, 97A, 16–26. DOI: 10.1002/jbm.a.33006.
   Web of Science ®Google Scholar
• Fujikawa, S.; Nakamura, S.; Kooa, K. Genipin, a New Type of Protein Crosslinking Reagent from Gardenia Fruits. Agric. Biol. Chem. 1988, 52, 869–870. DOI: 10.1080/00021369.1988.10868755.
   Web of Science ®Google Scholar
• Hou, Y. C.; Tsai, S. Y.; Lai, P. Y.; Chen, Y. S.; Chao, P. D. L. Metabolism and Pharmacokinetics of Genipin and Geniposide in Rats. Food. Chem. Toxicol. 2008, 46, 2764–2769. DOI: 10.1016/j.fct.2008.04.033.
   PubMed Web of Science ®Google Scholar
• Patel, A. K.; Michaud, P.; de Baynast, H.; Grediac, M. Preparation of Chitosan-Based Adhesives and Assessment of Their Mechanical Properties. J. Appl. Polym. Sci. 2012, 127, 3869–3876. DOI: 10.1002/app.37685.
   Google Scholar
• Touyama, R.; Inoue, K.; Takeda, Y.; Yatsuzuka, M.; Ikumoto, T.; Moritome, N.; Shingu, T.; Yokoi, T.; Inouye, H. Studies on the Blue Pigments Produced from Genipin and Methylamine. II. On the Formation Mechanisms of Brownish-Red Intermediates Leading to the Blue Pigment Formation. Chem. Pharm. Bull. 1994, 42, 1571–1578. DOI: 10.1248/cpb.42.1571.
   Web of Science ®Google Scholar
• Yao, C. H.; Liu, B. S.; Chang, C. J.; Hsu, S. H.; Chen, Y. S. Preparation of Networks of Gelatin and Genipin as Degradable Biomaterials. Mater. Chem. Phys. 2004, 83, 204–208. DOI: 10.1016/j.matchemphys.2003.08.027.
   Web of Science ®Google Scholar
• Butler, M. F.; Ng, Y. F.; Pudney, P. D. A. Mechanism and Kinetics of the Crosslinking Reaction Between Biopolymers Containing Primary Amine Groups and Genipin. J. Polym. Sci. A Polym. Chem. 2003, 41, 3941–3953. DOI: 10.1002/pola.10960.
   Web of Science ®Google Scholar
• Desbrières, J. Viscosity of Semiflexible Chitosan Solutions: Influence of Concentration, Temperature, and Role of Intermolecular Interactions. Biomacromolecules. 2002, 3, 342–349.
   PubMed Web of Science ®Google Scholar
• Narayanan, A.; Kartik, R.; Sangeetha, E.; Dhamodharan, R. Super Water Absorbing Polymeric Gel from Chitosan, Citric Acid and Urea_ Synthesis and Mechanism of Water Absorption. Carbohydrate. Polymers. 2018, 9, 152–160. DOI: 10.1016/j.carbpol.2018.03.028.
   Google Scholar
• Narayanan, A.; Dhamodharan, R. Super Water-Absorbing New Material from Chitosan, EDTA and Urea. Carbohyd. Polym. 2015, 134, 337–343. DOI: 10.1016/j.carbpol.2015.08.010.
   PubMed Web of Science ®Google Scholar
• Correlo, V. M.; Pinho, E. D.; Pashkuleva, I.; Bhattacharya, M.; Neves, N. M.; Reis, R. L. Water Absorption and Degradation Characteristics of Chitosan-Based Polyesters and Hydroxyapatite Composites. Macromol. Biosci. 2007, 7, 354–363. DOI: 10.1002/mabi.200600233.
   PubMed Web of Science ®Google Scholar
• Domján, A.; Bajdik, J.; Pintye-Hódi, K. Understanding of the Plasticizing Effects of Glycerol and PEG 400 on Chitosan Films Using Solid-State NMR Spectroscopy. Macromolecules. 2009, 42, 4667–4673. DOI: 10.1021/ma8021234.
   Web of Science ®Google Scholar
• Burdurlu, E.; Kılıç, Y.; Elibol, G. C.; Kılıç, M. The Shear Strength of Calabrian Pine (Pinus Brutia Ten.) Bonded with Polyurethane and Polyvinyl Acetate Adhesives. J. Appl. Polym. Sci. 2006, 99, 3050–3061. DOI: 10.1002/app.22905.
   Web of Science ®Google Scholar
• Lee, D.; Lee, M. J.; Son, D. W.; Park, B. D. Adhesive Performance of Woods Treated with Alternative Preservatives. Wood Sci. Technol. 2006, 40, 228–236. DOI: 10.1007/s00226-005-0036-7.
   Web of Science ®Google Scholar
• Abdelmoula, M.; Hlima, H. B.; Michalet, F.; Bourduche, G.; Delattre, A.; Gravier, C.; Grédiac, M.; Mathias, J.-D.; Michaud, P.; de Baynast, H. Chitosan-Based Adhesive: Optimization of Tensile Shear Strength in Dry and Wet Conditions. Polysaccharides. 2020, 2, 110–120. DOI: 10.3390/polysaccharides2010008.
   Google Scholar