Cited by 88Polymer crystallization and propertiesbiodegradable polymer synthesis and propertiesAdvanced Polymer Synthesis and Characterization

Polyethylene Incorporating Diels–Alder Comonomers: A “Trojan Horse” Strategy for Chemically Recyclable Polyolefins

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Parke, Sarah M., Lopez, Jaqueline C., Cui, Shilin, LaPointe, Anne M., Coates, Geoffrey W.·2023·Angewandte Chemie International Edition

Abstract

Polyolefins with periodic unsaturation in the backbone chain are sought after for synthesizing chemically recyclable polymers or telechelic polyolefin macromonomers. Here we introduce a bottom‐up synthesis of unsaturated high‐density polyethylene (HDPE) via copolymerization of ethylene with dimethyl 7‐oxabicyclo[2.2.1]hepta‐2,5‐diene‐3,5‐dicarboxylate followed by post‐polymerization retro‐Diels–Alder to unveil hidden double bonds in the polymer backbone. The incorporation of this “Trojan Horse” comonomer was varied and a series of unsaturated HDPE polymers with block lengths of 1.2, 1.9, and 3.5 kDa between double bonds was synthesized. Cross metathesis of unsaturated HDPE samples with 2‐hydroxyethyl acrylate yielded telechelic ester terminated PE macromonomers suitable for the preparation of ester‐linked PE. These materials were depolymerized and repolymerized, making them suitable candidates for chemical recycling. The ester‐linked PE displayed thermal and mechanical properties comparable to commercial HDPE.

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Cited by

Sorted by citations

Authors
Parke, S. M., Lopez, J. C., Cui, S., LaPointe, A. M., & Coates, G. W.
Affiliations
Cornell University (US)
Corresponding author
Coates, Geoffrey W.
Venue
Angewandte Chemie International Edition
Publisher
Wiley
Published
2023-06-15
Volume
62
Issue
30
Pages
e202301927-e202301927
ISSN
  • 1433-7851 (ISSN-L)
  • 1521-3773
OpenAlex
W4376108845
Cited by
88
References
59
Citations by year
2026: 27 · 2025: 30 · 2024: 23 · 2023: 8
FWCI
6.69
Type
journal article
Language
en
Open access
Locations
  • Angewandte Chemie International Edition (publishedVersion)
  • PubMed (publishedVersion)
  • OSTI OAI (U.S. Department of Energy Office of Scientific and Technical Information) (submittedVersion)
Funders
U.S. Department of Energy (DE-AC02-07CH11358)
Topics
  • Physical Sciences › Materials Science › Polymers and Plastics › Polymer crystallization and properties
  • Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
  • Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
Keywords
retro-Diels-Alder reaction, ethylene copolymerization, cross-metathesis, 2-hydroxyethyl acrylate, chemical recycling, block copolymers

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