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    Redesigned Hybrid Nylons with Optical Clarity and Chemical Recyclability
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    • Robin M. Cywar
      Robin M. Cywar
      Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, United States
      Renewable Resources and Enabling Sciences Center, National Renewable Energy Laboratory, Golden, Colorado 80401, United States
      More by Robin M. Cywar
    • Nicholas A. Rorrer
      Nicholas A. Rorrer
      Renewable Resources and Enabling Sciences Center, National Renewable Energy Laboratory, Golden, Colorado 80401, United States
      More by Nicholas A. Rorrer
      Orcidhttps://orcid.org/0000-0001-9134-5853
    • Heather B. Mayes
      Heather B. Mayes
      Renewable Resources and Enabling Sciences Center, National Renewable Energy Laboratory, Golden, Colorado 80401, United States
      More by Heather B. Mayes
      Orcidhttps://orcid.org/0000-0001-9373-0106
    • Anjani K. Maurya
      Anjani K. Maurya
      SLAC National Accelerator Laboratory, Stanford Synchrotron Radiation Lightsource, Menlo Park, California 94025, United States
      More by Anjani K. Maurya
    • Christopher J. Tassone
      Christopher J. Tassone
      SLAC National Accelerator Laboratory, Stanford Synchrotron Radiation Lightsource, Menlo Park, California 94025, United States
      More by Christopher J. Tassone
    • Gregg T. Beckham
      Gregg T. Beckham
      Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, United States
      Renewable Resources and Enabling Sciences Center, National Renewable Energy Laboratory, Golden, Colorado 80401, United States
      More by Gregg T. Beckham
      Orcidhttps://orcid.org/0000-0002-3480-212X
    • Eugene Y.-X. Chen*
      Eugene Y.-X. Chen
      Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, United States
      *Email: [email protected]
      More by Eugene Y.-X. Chen
      Orcidhttps://orcid.org/0000-0001-7512-3484
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2022, 144, 12, 5366–5376
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    https://doi.org/10.1021/jacs.1c12611
    Published March 15, 2022
    Copyright © 2022 American Chemical Society
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    Abstract

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    Aliphatic polyamides, or nylons, are typically highly crystalline and thermally robust polymers used in high-performance applications. Nylon 6, a high-ceiling-temperature (HCT) polyamide from ε-caprolactam, lacks expedient chemical recyclability, while low-ceiling temperature (LCT) nylon 4 from pyrrolidone exhibits complete chemical recyclability, but it is thermally unstable and not melt-processable. Here, we introduce a hybrid nylon, nylon 4/6, based on a bicyclic lactam composed of both HCT ε-caprolactam and LCT pyrrolidone motifs in a hybridized offspring structure. Hybrid nylon 4/6 overcomes trade-offs in (de)polymerizability and performance properties of the parent nylons, exhibiting both excellent polymerization and facile depolymerization characteristics. This stereoregular polyamide forms nanocrystalline domains, allowing optical clarity and high thermal stability, however, without displaying a melting transition before decomposition. Of a series of statistical copolymers comprising nylon 4/6 and nylon 4, a 50/50 copolymer achieves the greatest synergy in both reactivity and polymer properties of each homopolymer, offering an amorphous nylon with favorable properties, including optical clarity, a high glass transition temperature, melt processability, and full chemical recyclability.

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    Cite this: J. Am. Chem. Soc. 2022, 144, 12, 5366–5376
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