Related Experiment Video
Updated: Jun 28, 2025

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
Published on: November 21, 2017
Chemically Recyclable, High Molar Mass Polyoxazolidinones via Ring-Opening Metathesis Polymerization
Arpan Pal1, Allison R Wong1, Jessica R Lamb1
1Department of Chemistry, University of Minnesota-Twin Cities, Minneapolis, Minnesota 55455, United States.
Chemically recyclable polyoxazolidinones (POxa) were synthesized with high molar masses using a novel ring-opening metathesis polymerization. This breakthrough enables facile monomer recycling and versatile applications for advanced materials.
Area of Science:
- Polymer Chemistry
- Materials Science
- Organic Synthesis
Background:
- Developing chemically recyclable polymers with tunable properties is crucial for next-generation materials.
- Polyoxazolidinones (POxa) offer high polarity and thermal stability but face limitations in synthesis and recycling.
Purpose of the Study:
- To develop a robust synthesis for high molar mass polyoxazolidinones (POxa).
- To establish facile chemical recycling methods for POxa to their monomeric units.
- To explore the tunable properties of these novel polymers.
Main Methods:
- Ring-opening metathesis polymerization (ROMP) of oxazolidinone-fused cyclooctenes.
- Characterization of polymer thermal stability and glass transition temperatures.
- Demonstration of chemical recycling and repolymerization.
Main Results:
- Achieved synthesis of high molar mass POxa via ROMP.
- Polymers exhibited high thermal stability (mass loss <5% at 382-411 °C).
- Tunable glass transition temperatures (14-48 °C) were achieved by controlling side chain structure.
- Facile chemical recycling to monomer and subsequent repolymerization was demonstrated.
Conclusions:
- This study presents the first chain-growth synthesis of POxa, overcoming limitations of previous methods.
- The developed method provides a versatile platform for POxa synthesis and application.
- Facile recyclability and tunable properties position POxa as a promising class of polyurethanes.
Related Concept Videos
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
Olefin Metathesis Polymerization: Overview
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
Base-Catalyzed Ring-Opening of Epoxides
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Ziegler–Natta Chain-Growth Polymerization: Overview
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...

