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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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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: 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 species into...
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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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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Anionic Chain-Growth Polymerization: Overview01:20

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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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A New Phosphine for Efficient Free Radical Polymerization under Air.

Julie Kirschner1, Jean-Michel Becht1, Joachim E Klee2

  • 1Institut de Sciences des Matériaux de Mulhouse (IS2M), UMR CNRS 7361, University of Haute-Alsace, 15 rue Jean Starcky, Mulhouse Cedex, 68057, France.

Macromolecular Rapid Communications
|March 21, 2020
PubMed
Summary

A novel phosphine coinitiator enhances camphorquinone-based polymerization of (meth)acrylates. This dual-function molecule overcomes oxygen inhibition and initiates polymerization, enabling amine-free systems and improved depth of cure under blue light.

Keywords:
oxygen inhibitionphotoinitiatorsphotopolymerization

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Area of Science:

  • Polymer Chemistry
  • Photopolymerization
  • Organic Synthesis

Background:

  • Camphorquinone (CQ) is a common photoinitiator for dental composites.
  • Oxygen inhibition is a major challenge in free radical polymerization.
  • Amine-based coinitiators are often used but can cause discoloration.

Purpose of the Study:

  • To develop a novel phosphine coinitiator for camphorquinone-based photoinitiating systems.
  • To investigate its dual functionality in overcoming oxygen inhibition and initiating polymerization.
  • To explore amine-free systems and assess the depth of cure in composites.

Main Methods:

  • Synthesis of a novel phosphine molecule with an integrated iodonium salt moiety.
  • Evaluation of the phosphine as a coinitiator with camphorquinone for (meth)acrylate polymerization under blue light.
  • Investigation of photopolymerization in composite formulations using the developed system.
  • Assessment of oxygen inhibition mitigation and depth of cure using standard techniques.

Main Results:

  • The new phosphine acts as an efficient coinitiator with camphorquinone for (meth)acrylate polymerization under blue light.
  • The phosphine moiety effectively overcomes oxygen inhibition.
  • The iodonium salt moiety initiates the polymerization process, enabling amine-free systems.
  • Excellent polymerization performance and significant depth of cure (in composites) were achieved with short irradiation times (20 s).

Conclusions:

  • A novel dual-functional phosphine coinitiator offers an efficient alternative for camphorquinone-based photopolymerization systems.
  • The developed system effectively mitigates oxygen inhibition and allows for amine-free formulations.
  • The photoinitiating system demonstrates potential for applications requiring rapid curing and good depth of cure, such as in dental composites.