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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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Bio-based aliphatic polyurethanes through ADMET polymerization in bulk and green solvent.

Thomas Lebarbé1, Arvind Sudhakar More, Prakash Sudhir Sane

  • 1Laboratoire de Chimie des Polymères Organiques, Université de Bordeaux, ENSCBP, 16 Avenue Pey-Berland, F 33607, Pessac Cedex, France; Laboratoire de Chimie des Polymères Organiques, CNRS, F 33607, Pessac Cedex, France; French Environment and Energy Management Agency, 20 avenue du Grésillé-BP, 90406, F 49004, Angers Cedex 01, France.

Macromolecular Rapid Communications
|December 17, 2013
PubMed
Summary

Researchers developed a new method for creating α,ω-diene urethane monomers from bio-based resources. These monomers were polymerized using metathesis, and their properties were analyzed, offering insights into sustainable polymer development.

Keywords:
ADMETCurtius rearrangementfatty acidspolyurethanesolution

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Developing sustainable monomers is crucial for green chemistry.
  • Metathesis polymerization offers a versatile route to novel polymer architectures.
  • Bio-based feedstocks are increasingly important for reducing reliance on petrochemicals.

Purpose of the Study:

  • To synthesize a novel α,ω-diene urethane monomer via a new synthetic route.
  • To investigate the Ring-Opening Metathesis Polymerization (ROMP) of this monomer and other bio-based α,ω-dienes.
  • To evaluate catalyst tolerance and the impact of different organic functionalities on polymer properties.

Main Methods:

  • Synthesis of α,ω-diene urethane monomer from 10-undecenoic acid.
  • Ring-Opening Metathesis Polymerization (ADMET) in bulk and solution.
  • Screening of common metathesis catalysts for functional group tolerance.
  • Analysis of thermomechanical properties of the resulting polymers.

Main Results:

  • A new synthetic pathway to α,ω-diene urethane monomers was established.
  • Successful ADMET polymerization of urethane-containing and other bio-based α,ω-dienes was achieved.
  • Metathesis catalyst tolerance towards urethane groups and the green solvent Polarclean was evaluated.
  • The influence of various organic functionalities on polymer thermomechanical properties was determined.

Conclusions:

  • The proposed synthetic route provides access to novel urethane-containing monomers.
  • ADMET polymerization is a viable method for creating polymers from these bio-based dienes.
  • Understanding structure-property relationships is key for designing advanced sustainable polymers.