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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
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Radical Chain-Growth Polymerization: Chain Branching01:17

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The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Polymers02:34

Polymers

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The word polymer is derived from the Greek words “poly” which means “many” and “mer” which means “parts”. Polymers are long chains of molecules composed of repeating units of smaller molecules, known as monomers. They either occur naturally, such as DNA and proteins, or can be constructed synthetically, like plastics. They have varied structural characteristics, such as linear chains, branched chains, or complex networks, that contribute to the...
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Cross-Linked Polyolefins through Tandem ROMP/Hydrogenation.

Caitlin S Sample1, Brenden D Hoehn2, Marc A Hillmyer1

  • 1Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455-0431, United States.

ACS Macro Letters
|March 19, 2024
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Summary

This study introduces a novel tandem ring-opening metathesis polymerization (ROMP) and hydrogenation method for creating cross-linked polyolefins. This process enhances oxidative stability and mechanical properties of polyolefin networks.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Organic Synthesis

Background:

  • Cross-linked polyolefins offer superior impact strength, abrasion resistance, and chemical/thermal stability compared to thermoplastic polyolefins.
  • Traditional methods often rely on post-polymerization cross-linking, which can be inefficient.
  • Developing new synthetic routes for robust cross-linked polyolefin networks is crucial for advanced material applications.

Purpose of the Study:

  • To present a novel tandem ring-opening metathesis polymerization (ROMP) and hydrogenation approach for synthesizing cross-linked polyolefin networks.
  • To investigate the effect of hydrogenation on the oxidative stability and mechanical properties of these novel networks.
  • To explore the structure-property relationships in cyclooctene (COE)-co-dicyclopentadiene (DCPD) based networks.

Main Methods:

  • Synthesis of COE-co-DCPD networks via ring-opening metathesis polymerization (ROMP).
  • In-situ activation of the dispersed ruthenium metathesis catalyst for subsequent hydrogenation using hydrogen gas.
  • Characterization of thermal transitions (glass and melting transitions) to determine optimal hydrogenation temperatures.

Main Results:

  • COE-rich materials exhibited polyethylene-like crystallinity (25%) and melting points (Tm = 107 °C) with high ductility (>750% extension).
  • DCPD-rich materials displayed glassy behavior (Tg = 84 °C) and higher stiffness (E = 710 MPa), with all materials showing high tensile toughness.
  • Hydrogenation significantly improved oxidative stability, preventing mechanical degradation observed in unsaturated counterparts upon air exposure.

Conclusions:

  • The tandem ROMP/hydrogenation method provides an effective route to produce cross-linked polyolefin networks with enhanced properties.
  • Hydrogenation is critical for improving the long-term oxidative stability of these polyolefin networks.
  • The developed materials demonstrate tunable properties based on COE/DCPD ratios, offering potential for diverse applications.