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Issue 46, 2016
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Synthesis and post-polymerisation modification of an epoxy-functional polycarbonate

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Abstract

The synthesis of an epoxide-functional polycarbonate via the selective carbonate ring-opening polymerisation (ROP) of trimethylenepropane oxirane ether carbonate (TMOC) monomer was investigated using a range of organocatalysts. The catalyst 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) provided the best polymerisation control without reacting with the epoxide functionality and the resulting polymers presented low dispersities and molecular weights close to that predicted from the monomer-to-initiator ratio. Subsequently, the post-polymerisation functionalisation of PTMOC through thiol–epoxy reactions was investigated using a series of thiols and showed to be effective especially for thiophenols. Finally, modification of PTMOC by ring-opening the epoxide with amines proved to be challenging as the conditions applied led to a degradation of the polymer backbone and/or formation of crosslinked materials.

Graphical abstract: Synthesis and post-polymerisation modification of an epoxy-functional polycarbonate

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Supplementary files

Article information


Submitted
17 Sep 2016
Accepted
29 Oct 2016
First published
31 Oct 2016

Polym. Chem., 2016,7, 7108-7115
Article type
Paper

Synthesis and post-polymerisation modification of an epoxy-functional polycarbonate

P. K. Kuroishi, M. J. Bennison and A. P. Dove, Polym. Chem., 2016, 7, 7108
DOI: 10.1039/C6PY01636G

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