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Dynamic covalent cross-linked polymer gels through the reaction between side-chain β-keto ester and primary amine groups
Affiliation:1. Department of Food Science and Human Nutrition, College of Applied and Health Sciences, A''Sharqiah University, Ibra, Oman;2. Department of Chemistry, College of Science, Sultan Qaboos University, PO Box 36, Al-Khod 123, Muscat, Oman;3. Biomolecular NMR, Ruhr University of Bochum, 44780 Bochum, Germany;4. Inorganic Chemistry 1, Ruhr-University Bochum, Universitätsstrasse 150, 44801 Bochum, Germany;1. Departamento de Química, Facultad de Química, Universidad de Chile, La Palmeras 3425, Nuñoa, casilla 653, Santiago de Chile, Chile;2. Universidad Autónoma de Chile, Instituto de Ciencias Químicas Aplicadas, Inorganic Chemistry and Molecular Material Center, Av. El Llano Subercaseaux 2801, San Miguel, Santiago de Chile, Chile;3. Departamento de Química Orgánica e Inorgánica (IUQOEM), Facultad de Química, Universidad de Oviedo, Julián Clavería s/n, 33006 Oviedo, Spain
Abstract:A dynamic covalent gel network was constructed via the coupling reaction between the pendant primary amine groups of poly(l-leucine methacryloyloxyethyl ester) (P(H2N-Leu-EMA)) and the side-chain β-keto ester functionalities of poly(2-(acetoacetoxy)ethyl methacrylate) (PAEMA) by varying the molar ratios of P(H2N-Leu-EMA)/PAEMA and the concentration of polymers in different solvents at room temperature. Fourier transform infrared (FT-IR) spectroscopy and solid-state 13C nuclear magnetic resonance (NMR) study confirmed the newly formed enamine bonds in the polymeric gel. Rheological studies showed that the mechanical strength of gels increased with increasing weight percentage (wt.%) of polymers in solution. Furthermore, polymer gels can be transferred to the mixture of starting polymer solutions by regulating the pH of the system, which can be further transformed into the gel state by adding an external base.
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