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Updated: Jan 15, 2026

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
Published on: August 25, 2016
From Levulinic Acid to Imines: Creating Biobased, Recyclable, Cross-linked Rubbers through Covalent Adaptive Networks
Luca Lenzi1,2, Juan Carlos Chicharro3, Micaela Degli Esposti1,2
1Department of Civil, Chemical, Environmental and Materials Engineering (DICAM), Università di Bologna, Via Terracini 28, 40131 Bologna, Italy.
This study introduces a novel, fully biobased rubber network using dynamic imine bonds for recyclability. The optimized formulation demonstrates enhanced mechanical properties after recycling, showcasing sustainable material potential.
Area of Science:
- Materials Science
- Polymer Chemistry
- Sustainable Materials
Background:
- Dynamic covalent bonds enable the design of recyclable materials.
- Imine chemistry is a key strategy for creating adaptive polymer networks.
- Developing sustainable and recyclable rubber-based materials is crucial.
Purpose of the Study:
- To create a fully biobased and recyclable rubber network using imine chemistry.
- To investigate the use of biobased ketones and amines as cross-linkers.
- To evaluate the recyclability and mechanical performance of the novel rubber network.
Main Methods:
- Cross-linking epoxidized natural rubber (ENR) with glycerol trilevulinate (GT) and hexamethylene diamine (HMDA).
- Characterization using mechanical tests, swelling measurements, and dielectric investigations.
- Assessing network reconstruction and performance after reprocessing.
Main Results:
- A hybrid adaptive network based on imine and hydrogen bonds was successfully formed.
- The optimal formulation (5 phr GT and 5 phr HMDA) showed improved tensile strength after recycling.
- Network integrity and mechanical properties were preserved through synergistic covalent and noncovalent interactions.
Conclusions:
- The developed biobased rubber network exhibits excellent recyclability and adaptability.
- Levulinic acid derivatives are effective for creating sustainable rubber materials.
- This approach offers a promising route for producing high-performance, eco-friendly rubber products.
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