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Title: Closed-loop recycling of plastics enabled by dynamic covalent diketoenamine bonds

Journal Article · · Nature Chemistry
ORCiD logo [1];  [2];  [1]; ORCiD logo [3]
  1. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). The Molecular Foundry
  2. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). The Molecular Foundry; Univ. of California, Berkeley, CA (United States). Dept. of Chemistry
  3. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). The Molecular Foundry and Materials Science Div.

Recycled plastics are low-value commodities due to residual impurities and the degradation of polymer properties with each cycle of re-use. Plastics that undergo reversible polymerization allow high-value monomers to be recovered and re-manufactured into pristine materials, which should incentivize recycling in closed-loop life cycles. However, monomer recovery is often costly, incompatible with complex mixtures and energy-intensive. Here, we show that next-generation plastics-polymerized using dynamic covalent diketoenamine bonds-allow the recovery of monomers from common additives, even in mixed waste streams. Poly(diketoenamine)s 'click' together from a wide variety of triketones and aromatic or aliphatic amines, yielding only water as a by-product. Recovered monomers can be re-manufactured into the same polymer formulation, without loss of performance, as well as other polymer formulations with differentiated properties. The ease with which poly(diketoenamine)s can be manufactured, used, recycled and re-used-without losing value-points to new directions in designing sustainable polymers with minimal environmental impact.

Research Organization:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
AC02-05CH11231
OSTI ID:
1596671
Journal Information:
Nature Chemistry, Vol. 11, Issue 5; ISSN 1755-4330
Publisher:
Nature Publishing GroupCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 259 works
Citation information provided by
Web of Science

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Cited By (21)

Microplasmas for Advanced Materials and Devices journal December 2019
Polymernetzwerke: Von Kunststoffen und Gelen zu porösen Gerüsten journal January 2020
Polar‐Functionalized, Crosslinkable, Self‐Healing, and Photoresponsive Polyolefins journal November 2019
Conformational Entropy as a Means to Control the Behavior of Poly(diketoenamine) Vitrimers In and Out of Equilibrium journal November 2019
Polymer Networks: From Plastics and Gels to Porous Frameworks journal March 2020
Polar‐Functionalized, Crosslinkable, Self‐Healing, and Photoresponsive Polyolefins journal November 2019
Conformational Entropy as a Means to Control the Behavior of Poly(diketoenamine) Vitrimers In and Out of Equilibrium journal January 2020
Eutectic Molecular Liquids Based on Hydrogen Bonding and π–π Interaction for Exfoliating Two‐dimensional Materials and Recycling Polymers journal August 2019
Reflections on the Evolution of Smart Polymers journal January 2020
Dynamic multiphase semi-crystalline polymers based on thermally reversible pyrazole-urea bonds journal October 2019
Facile synthesis of “digestible”, rigid-and-flexible, bio-based building block for high-performance degradable thermosetting plastics journal January 2020
Bulk network polymers with dynamic B–O bonds: healable and reprocessable materials journal January 2020
Recyclable sulfone-containing polymers via ring-opening polymerization of macroheterocyclic siloxane monomers: synthesis, properties and recyclability journal January 2019
Solvent processable and recyclable covalent adaptable organogels based on dynamic trans-esterification chemistry: separation of toluene from azeotropic mixtures journal January 2020
Structural tuning of polycaprolactone based thermadapt shape memory polymer journal January 2020
Dynamic covalent polymers for biomedical applications journal January 2020
Synthesis of novel polycarbonyl Schiff bases by ring-opening reaction of ethyl 5-acyl-4-pyrone-2-carboxylates with primary mono- and diamines journal January 2019
Facile catalyst-free synthesis, exchanging, and hydrolysis of an acetal motif for dynamic covalent networks journal January 2019
High-performance, command-degradable, antibacterial Schiff base epoxy thermosets: synthesis and properties journal January 2019
Assembling a Natural Small Molecule into a Supramolecular Network with High Structural Order and Dynamic Functions journal July 2019
Solid Wastes Provide Breeding Sites, Burrows, and Food for Biological Disease Vectors, and Urban Zoonotic Reservoirs: A Call to Action for Solutions-Based Research journal January 2020


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