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Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

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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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Radical Chain-Growth Polymerization: Mechanism01:09

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The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this...
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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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Anionic Chain-Growth Polymerization: Mechanism01:04

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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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Amines to Amides: Acylation of Amines01:19

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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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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Low-Migration Compounds with Amine Functionality as Coinitiators of Radical Polymerization.

Hong Chen1,2, Michael Schmitt1,2, Bernadette Graff1,2

  • 1Université de Haute-Alsace, CNRS, IS2M UMR 7361, Mulhouse, F-68100, France.

Macromolecular Rapid Communications
|June 3, 2024
PubMed
Summary

Researchers developed a novel, non-leaching photoinitiator system for dental resins. This camphorquinone (CQ) and amine combination enhances safety by preventing toxic amine leaching during polymerization.

Keywords:
coinitiatorsdental materialsfree radical photopolymerizationlow‐migration compounds

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Biomaterials

Background:

  • Two-component camphorquinone (CQ)/aromatic amine systems are widely used in photopolymerization.
  • Concerns exist regarding the toxicity and leaching of aromatic amines from these systems.
  • Dental materials require safe and effective photoinitiation systems.

Purpose of the Study:

  • To develop novel, non-leaching coinitiator systems for dental methacrylate resins.
  • To create a camphorquinone (CQ)-based system with copolymerizable amines.
  • To ensure free radical polymerization under blue light with minimal migration.

Main Methods:

  • Molecular modeling to design hydrogen donors with low C─H bond dissociation energy.
  • Chemical modification to incorporate copolymerizable methacrylate groups into amines.
  • Synthesis and performance comparison of the novel photoinitiation system (PIS) against CQ/ethyl-4-dimethylaminobenzoate (EDB).
  • Mechanistic investigation using molecular orbital calculations and electron spin resonance (ESR).

Main Results:

  • Successful synthesis of a novel, copolymerizable coinitiator.
  • Demonstrated effectiveness of the new PIS in dental methacrylate resin polymerization.
  • Confirmation of low migration and leachability of the novel coinitiator.
  • Elucidation of the reaction mechanism of the proposed PIS.

Conclusions:

  • The developed CQ-based PIS with copolymerizable amines offers a safer alternative to traditional systems.
  • This innovation addresses concerns about aromatic amine toxicity and leaching in photopolymerized dental materials.
  • The study provides a new strategy for designing low-migration photoinitiators for various applications.