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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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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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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Radical Chain-Growth Polymerization: Overview01:10

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Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael...
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Microstructural Analysis of Benzoxazine Cationic Ring-Opening Polymerization Pathways.

Francisco W M Ribeiro1, Isaac Omari2, Gilian T Thomas2

  • 1Department of Fundamental Chemistry, Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes, 748, Cidade Universitária, São Paulo, SP, 05508-000, Brazil.

Macromolecular Rapid Communications
|September 16, 2023
PubMed
Summary

This study differentiates phenoxy and phenolic products in benzoxazine polymerization using mass spectrometry. The findings reveal the initial step favors the phenoxy product via the type I pathway.

Keywords:
benzoxazinesinfrared multiple photon dissociationion mobility spectrometrypolymerization mechanismring opening polymerization

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Area of Science:

  • Polymer Chemistry
  • Materials Science

Background:

  • Benzoxazine polymerization is crucial for advanced materials.
  • Understanding the cationic ring-opening polymerization (ROP) mechanism is key to controlling polymer properties.

Purpose of the Study:

  • To differentiate phenoxy and phenolic products formed during benzoxazine polymerization.
  • To elucidate the initial steps and pathways of cationic ring-opening polymerization (ROP) in polybenzoxazine formation.

Main Methods:

  • Utilized mass spectrometry for evaluating the initial polymerization step.
  • Employed infrared multiple photon dissociation (IRMPD) and ion mobility spectrometry (IMS) for pathway differentiation.

Main Results:

  • Successfully differentiated between phenoxy and phenolic products.
  • Identified the type I pathway as dominant in the initial stages, yielding the phenoxy product.
  • Proposed that the phenoxy product interconverts to the more stable type II phenolic product at later stages.

Conclusions:

  • Provided critical insights into the initial step of benzoxazine polymerization.
  • The findings enable the development of optimized polymerization conditions.
  • Established a method for evaluating other multifunctional polymerization processes.