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Hydrogels are soft water-rich materials with physical properties that can be easily tuned by modifying their network structure. For instance, increasing or decreasing the cross-linking density has a profound effect on their water absorption capabilities and mechanical strength. These physical changes are showcased in a new experiment for organic chemistry and polymer science teaching laboratories based on the practical green synthesis and characterization of lactose methacrylate derived hydrogels. Lactose, a disaccharide derived from dairy waste byproducts, is functionalized with photoreactive methacrylate groups using methacrylic anhydride. The resulting mixture is subsequently photoirradiated to generate a cross-linked hydrogel. Structure–property relationships are assessed through comparative studies of three hydrogels of varying compositions. Compression tests and swelling studies in different aqueous environments offer a guided-inquiry experience. Students determine a relationship between cross-linking density and the physical properties of the hydrogels. This experiment highlights the valorization of biomass and multiple green chemistry principles including use of renewable feedstocks, atom economy, energy efficiency, waste prevention, and water as a benign solvent. Learning outcomes for an organic chemistry laboratory course include introduction to disaccharide and cross-linked polymer structures, observable physical change dependency with cross-linking density, and laboratory methods for evaluating water absorption capacities. Objectives aligned with a polymer course are incorporating mechanical compression instrumentation, mechanistic understanding of light-induced free radical polymerizations, and an appreciation for the application of hydrogels to commercial products. Overall, the translation of a current literature publication to an inexpensive and versatile experiment engages students in a modern example of sustainable polymer chemistry.more » « less
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Abstract Teaching experiments involving edible, biodegradable calcium alginate beads serve as an attractive model system to introduce upper secondary age students to core chemistry topics through innovations in sustainable consumer products. A teaching experiment is described that engages students with the synthesis of calcium alginate hydrogel beads from sodium alginate and calcium lactate, two food-safe and renewable materials. The beads’ outer membranes are a result of ionic interactions between carboxylate groups from alginate strands and the divalent calcium cations between them, thus forming cross-linked polymers. Protonation of the carboxylate groups on the alginate strands decreases crosslinking density affecting bead formation. First, various concentrations of citric acid are used to lower the pH of the sodium alginate solution and the effect on the calcium alginate bead formation is observed. A correlation between pH and bead shape and firmness is derived. This information is then used to explore juices with varying natural acidities. The experiment is amenable to implementation in the classroom or as an at-home activity. Learning outcomes include acid-base reactions, chemical bonding, polymer structures, and green chemistry concepts. Students consider the environmental challenges of traditional plastics used in packaging and how innovative new commercial products are attempting to provide solutions.more » « less
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