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Updated: Jun 7, 2025

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
Published on: August 25, 2016
Chemical and Solvent-Based Recycling of DGEBA-Based Epoxy Thermoset and Carbon-Fiber Reinforced Epoxy Composite
Özgün Dağlar1, Tankut Türel1, Christos Pantazidis1
1Polymer Performance Materials Group, Department of Chemical Engineering and Chemistry, and Institute for Complex Molecular Systems (ICMS), Eindhoven University of Technology, Eindhoven, 5600 MB, The Netherlands.
Abstract:
Epoxy systems are essential in numerous industrial applications due to their exceptional mechanical properties, thermal stability, and chemical resistance. Yet, recycling epoxy networks and reinforcing materials in epoxy composites remains challenging, raising environmental concerns. The critical challenge is the recovery of well-defined molecules upon depolymerization. To address these issues, an innovative strategy is developed utilizing imine-containing secondary amine hardener (M1). The reaction of M1 with DGEBA produced high-performance epoxy thermoset P1, which exhibits Young's modulus of 2.18 GPa and tensile strength of 63.4 MPa, and excellent stability in neutral aqueous conditions. Upon carbon-fiber reinforcement, Young's modulus and tensile strength are significantly elevated to 10.99 GPa and 328.3 MPa, respectively. The reactive secondary amine functionalities enabled the tailored network to display a well-defined growth pattern, yielding only well-defined molecules and intact carbon fibers upon acidic depolymerization. Consequently, the recycled polymers retained properties identical to those of P1. Notably, it is discovered that despite the cross-linked nature of the epoxy networks, complete dissolution in dichloromethane facilitated straightforward solvent-based recycling, allowing the recovery of undamaged carbon fibers and an epoxy thermoset with properties matching the virgin material. Presented novel monomer design and approach showcased two important and efficient recycling options for epoxy systems.
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