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Olefin Metathesis Polymerization: Overview01:13

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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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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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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Cationic Chain-Growth Polymerization: Mechanism00:57

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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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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Oxime-Based and Catalyst-Free Dynamic Covalent Polyurethanes.

Wen-Xing Liu1,2, Chi Zhang3, Huan Zhang1,2

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This study introduces poly(oxime-urethanes) (POUs), a novel dynamic polymer class. These polymers offer catalyst-free, healable, and recyclable materials with excellent mechanical properties, overcoming limitations of traditional polyurethanes.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Polyurethanes (PUs) are widely used but face limitations due to toxic catalysts and poor processability of thermosets.
  • Developing sustainable and processable alternatives to conventional PUs is crucial for advanced material applications.

Purpose of the Study:

  • To synthesize and characterize a new class of dynamic covalent polymers, poly(oxime-urethanes) (POUs).
  • To investigate the catalyst-free synthesis, thermal reversibility, and mechanical properties of POUs.
  • To explore the potential of POUs as sustainable alternatives to traditional polyurethanes.

Main Methods:

  • Uncatalyzed polyaddition of multifunctional oximes and hexamethylene diisocyanate (HDI) at ambient temperature.
  • Kinetics studies in various solvents, including dichloromethane (DCM), to determine optimal polymerization conditions.
  • Thermogravimetric analysis and dynamic mechanical analysis to assess thermal stability and reversibility.
  • Density functional theory (DFT) calculations to elucidate reaction mechanisms.

Main Results:

  • Achieved high polymerization conversion (∼99%) in 3 hours at 30 °C in DCM, producing linear POUs.
  • Demonstrated thermoreversible oxime-carbamate bonds at approximately 100 °C via a dissociative mechanism.
  • Cross-linked POUs exhibited catalyst-free healable and recyclable properties.
  • DFT calculations indicated the nitrone tautomer of oxime mediates fast polymerization and thermoreversibility.

Conclusions:

  • Poly(oxime-urethanes) (POUs) represent a promising new class of dynamic covalent polymers.
  • POUs offer facile, catalyst-free preparation, excellent mechanical performance, and dynamic properties (healability/recyclability).
  • The unique properties of POUs stem from the reversible oxime-carbamate linkage, mediated by the nitrone tautomer, paving the way for sustainable material development.