The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry

Lorenzo Massimo Polgar*, Martin van Duin, Francesco Picchioni

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

4 Citations (Scopus)
8 Downloads (Pure)

Abstract

A method for using Diels Alder thermo-reversible chemistry as cross-linking tool for rubber products is demonstrated. In this work, a commercial ethylene-propylene rubber, grafted with maleic anhydride, is thermo-reversibly cross-linked in two steps. The pending anhydride moieties are first modified with furfurylamine to graft furan groups to the rubber backbone. These pendant furan groups are then cross-linked with a bismaleimide via a Diels-Alder coupling reaction. Both reactions can be performed under a broad range of experimental conditions and can easily be applied on a large scale. The material properties of the resulting Diels-Alder cross-linked rubbers are similar to a peroxide-cured ethylene/ propylene/diene rubber (EPDM) reference. The cross-links break at elevated temperatures (> 150 degrees C) via the retro-Diels-Alder reaction and can be reformed by thermal annealing at lower temperatures (50-70 degrees C). Reversibility of the system was proven with infrared spectroscopy, solubility tests and mechanical properties. Recyclability of the material was also shown in a practical way, i.e., by cutting a cross-linked sample into small parts and compression molding them into new samples displaying comparable mechanical properties, which is not possible for conventionally cross-linked rubbers.

Original languageEnglish
Article number54496
Number of pages9
JournalJournal of visualized experiments : JoVE
Issue number114
DOIs
Publication statusPublished - Aug-2016

Keywords

  • Chemistry
  • Issue 114
  • Rubber
  • cross-linking
  • recycling
  • modification
  • Diels-Alder
  • thermo-reversibility
  • chemical engineering
  • MALEATED ETHYLENE/PROPYLENE COPOLYMERS
  • SOLID-STATE H-1-NMR
  • MALEIC-ANHYDRIDE
  • CLICK CHEMISTRY
  • NATURAL-RUBBER
  • CHAIN ENTANGLEMENTS
  • REACTIVE EXTRUSION
  • LINKING
  • FURAN
  • EPDM

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