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A Nitroxide for Effecting Controlled Nitroxide-Mediated Radical Polymerization at Temperatures ≤90 °C.

Neil R Cameron1, Olivier Lagrille1, Peter A Lovell2

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|May 24, 2022
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A new nitroxide, TITNO, and its alkoxyamine, Styryl-TITNO, enable controlled nitroxide-mediated polymerization (NMP) at lower temperatures. This allows for precise polymer synthesis with reduced thermal initiation, expanding NMP applications.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis

Background:

  • Nitroxide-mediated polymerization (NMP) is a controlled radical polymerization technique.
  • Established NMP methods often require high temperatures, limiting their applicability and potentially causing side reactions.

Purpose of the Study:

  • To design and synthesize a novel nitroxide (TITNO) and its alkoxyamine (Styryl-TITNO) for efficient NMP at lower temperatures (≤90 °C).
  • To investigate the thermal dissociation kinetics of Styryl-TITNO and its performance in polymerizing n-butyl acrylate and styrene.

Main Methods:

  • Synthesis of the TITNO nitroxide and its styrene alkoxyamine derivative.
  • Determination of the thermal dissociation rate coefficient (kd) and Arrhenius parameters for Styryl-TITNO.
  • NMP of n-butyl acrylate and styrene using Styryl-TITNO at temperatures below 90 °C.

Main Results:

  • Styryl-TITNO exhibits low activation energy (Ed = 104.1 kJ mol⁻¹) for thermal dissociation.
  • Lower dissociation rate coefficients and equilibrium constants compared to established nitroxides were observed.
  • Controlled polymerization of n-butyl acrylate and styrene was achieved at 90 °C and 70 °C, respectively, with good molecular weight control and low dispersity.
  • Elimination of complicating styrene thermal initiation at lower temperatures.

Conclusions:

  • TITNO and Styryl-TITNO represent a new class of alkoxyamines for NMP.
  • These new agents enable controlled polymerization at significantly lower temperatures than previously possible.
  • This advancement opens new avenues for synthesizing polymers with controlled architectures and properties under milder conditions.