Sustainable, Naringenin-Based Thermosets Show Reversible Macroscopic Shape Changes and Enable Modular Recycling

Abstract

A sustainable biobased thermoset exhibiting shape-memory behavior and modular recycling capabilities has been developed herein. The prepared thermoset consists of naringenin and biocompatible polymer components. Naringenin, which has three phenolic moieties, has been converted to a multifunctional monomer containing glycidyl groups and readily formed a thermosetting network via epoxide ring opening reaction with a poly­(ethylene glycol) diacid under solvent-free conditions. The resulting material is malleable yet as strong as articular cartilage and selectively absorbs water when compared with n-dodecane oil. Moreover, the thermoset can be physically reused. After being crumpled, stretched, or coiled, the initial shape of the material is restored in response to heat or water. Furthermore, the material is amenable to chemical recycling in a bulk state via transesterification, and its components can be recovered on a molecular level after degradation under benign conditions, as was confirmed using a model compound.

Smart and sustainable design of latent catalyst-containing benzoxazine-bio-resins and application studies

“…1b), which presents an intramolecular hydrogenbonding motif formed between a phenolic hydroxyl group and the oxygen atom of a carbonyl. The phenolic compound used, naringenin, is a natural renewable raw material abundant in different fruits, such as grapefruit, 31 sour orange, 32 and tart cherries. 33 The extraction method and content vary depending on the fruit.…”

Recent Progress on Molecular Photoacoustic Imaging with Carbon-Based Nanocomposites

“…We anticipate that the imaging techniques and the contrast agents described will be further developed into more advanced materials and to monitor or manipulate them using the PA signals generated from the materials [ 124 , 125 ]. Therefore, on the one hand, the agent materials can be incorporated into biocompatible polymers such as hydrogels or bio-based thermosets, to enhance sensing ability as a signal transducer for PA signals under physiological conditions [ 123 , 124 , 125 , 126 , 127 , 128 , 129 , 130 , 131 , 132 ]. On the other hand, they would provide spatiotemporal control of stimuli-responsive materials that exhibit auto-inductive or reversible responses [ 133 , 134 , 135 , 136 , 137 , 138 ] or would be used to analyze interior structures when embedded in complex materials containing biomimetic or hierarchical structures [ 104 , 117 , 139 , 140 , 141 ].…”

Recent Progress on Near-Infrared Photoacoustic Imaging: Imaging Modality and Organic Semiconducting Agents

“…Additionally, self-propagating reactions, such as self-assembly or triggered head-to-tail depolymerization [114,115,116,117,118], can readily turn on–off or even amplify the PA signal. Furthermore, addition of the PA properties to various network materials, such as porous materials or hydrogels [119,120,121,122,123,124,125,126], can provide a non-destructible in situ monitoring system or facile, selective manipulation of physical properties of the networks in response to NIR.…”