Issue 2, 2010
From the journal:

Polymer Chemistry

Direct RAFT polymerization of an unprotected isocyanate-containing monomer and subsequent structopendant functionalization using “click”-type reactions†

Joel D. Flores,a   Junghwan Shin,a   Charles E. Hoyleab  and  Charles L. McCormick*ab  

* Corresponding authors

a Department of Polymer Science, The University of Southern Mississippi, 118 College Drive #10076, Hattiesburg, MS, USA
E-mail: charles.mccormick@usm.edu
Fax: +1 601 266 5504
Tel: +1 601 266 4872

b Department of Chemistry and Biochemistry, The University of Southern Mississippi, 118 College Drive #10076, Hattiesburg, MS, USA

Abstract

The controlled reversible addition–fragmentation chain transfer (RAFT) homopolymerization of an unprotected isocyanate-containing monomer, in this case 2-(acryloyloxy)ethylisocyanate (AOI), is reported. The polymerization conditions were optimized in terms of the choice of RAFT chain transfer agent (CTA), polymerization temperature and the reaction medium. Direct RAFT polymerization of AOI requires a neutral CTA, and relatively low reaction temperature to yield AOI homopolymers with low polydispersities. Efficient side-chain functionalization of poly(2-(acryloyloxy)ethylisocyanate) (PAOI) homopolymers was achieved via reaction with model amine, thiol and alcohol compounds yielding urea, thiourethane and urethane derivatives, respectively. Reactions with amines and thiols (in the presence of base) were rapid, quantitative and efficient. However, the reaction with alcohols catalyzed by dibutyltin dilaurate (DBTDL) was relatively slow but proceeded to completion. Selective reaction pathways for the addition of difunctional ethanolamine and mercaptoethanol were also investigated.

Graphical abstract: Direct RAFT polymerization of an unprotected isocyanate-containing monomer and subsequent structopendant functionalization using “click”-type reactions

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Article information

DOI
https://doi.org/10.1039/B9PY00294D
Article type
Paper
Submitted
13 Oct 2009
Accepted
11 Nov 2009
First published
22 Dec 2009

Polym. Chem., 2010,1, 213-220

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Direct RAFT polymerization of an unprotected isocyanate-containing monomer and subsequent structopendant functionalization using “click”-type reactions

J. D. Flores, J. Shin, C. E. Hoyle and C. L. McCormick, Polym. Chem., 2010, 1, 213 DOI: 10.1039/B9PY00294D

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