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Related Experiment Videos

Why does Kevlar decompose, while Nomex does not, when treated with aqueous chlorine solutions?

Akin Akdag1, Hasan B Kocer, S D Worley

  • 1Department of Chemistry and Biochemistry and Department of Polymer and Fiber Engineering, Auburn University, Auburn, Alabama 36849.

The Journal of Physical Chemistry. B
|May 1, 2007
PubMed
Summary
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Kevlar decomposes when treated with bleach, unlike Nomex. This study found Kevlar’s diaminophenylene component oxidizes to a quinone, causing decomposition, while Nomex remains stable, explaining their different reactions to chlorination for biocidal applications.

Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Biocidal Applications

Background:

  • High-performance polymers Kevlar and Nomex have potential biocidal applications.
  • Reaction with sodium hypochlorite solution can create biocidal N-halamine groups.
  • Kevlar decomposes during chlorination, while Nomex does not.

Purpose of the Study:

  • To investigate the differing stability of Kevlar and Nomex under chlorination conditions.
  • To elucidate the chemical mechanisms behind Kevlar's decomposition during N-halamine formation.

Main Methods:

  • Synthesis of polymer mimics for Kevlar and Nomex.
  • Treatment of mimics with hypochlorous acid (a component of bleach).
  • Spectroscopic analysis to identify reaction products and mechanisms.

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Main Results:

  • The p-diaminophenylene component in the Kevlar mimic was oxidized to a quinone structure.
  • This quinone intermediate subsequently decomposed.
  • The Nomex mimic did not undergo a similar decomposition pathway.

Conclusions:

  • The oxidation and subsequent decomposition of the p-diaminophenylene moiety explain Kevlar's instability.
  • This mechanistic difference accounts for why Nomex is stable under chlorination while Kevlar is not.
  • Understanding these mechanisms is crucial for developing N-halamine biocidal materials from these polymers.