Jump to main content
Jump to site search

Issue 11, 2015
Previous Article Next Article

Poly(alkylene itaconate)s – an interesting class of polyesters with periodically located exo-chain double bonds susceptible to Michael addition

Author affiliations

Abstract

Itaconic acid is a bio-sourced dicarboxylic acid that carries a double bond; although several reports have dealt with the radical-initiated chain polymerization of dialkyl itaconates, only a few studies have utilized it as a di-acid monomer to prepare polyesters. In this study, we demonstrate that dibutyl itaconate can be melt-condensed with aliphatic diols to generate unsaturated polyesters; importantly, we show that the double bonds remain unaffected during the melt polymerization. A particularly useful attribute of these polyesters is that the exo-chain double bonds are conjugated to the ester carbonyl and, therefore, can serve as excellent Michael acceptors. A variety of organic thiols, such as alkane thiols, MPEG thiol, thio-glycerol, derivatized cysteine etc., were shown to quantitatively Michael-add to the exo-chain double bonds and generate interesting functionalized polyesters. Similarly, organic amines, such as N-methylbenzylamine, diallyl amine and proline, also add across the double bond; thus, these poly(alkylene itaconate)s could serve as potentially bio-benign polyesters that could be quantitatively transformed into a variety of interesting and potentially useful functionalized polymers.

Graphical abstract: Poly(alkylene itaconate)s – an interesting class of polyesters with periodically located exo-chain double bonds susceptible to Michael addition

Back to tab navigation

Supplementary files

Publication details

The article was received on 21 Nov 2014, accepted on 07 Jan 2015 and first published on 08 Jan 2015


Article type: Paper
DOI: 10.1039/C4PY01613K
Author version
available:
Download author version (PDF)
Citation: Polym. Chem., 2015,6, 2108-2114
  •   Request permissions

    Poly(alkylene itaconate)s – an interesting class of polyesters with periodically located exo-chain double bonds susceptible to Michael addition

    S. Chanda and S. Ramakrishnan, Polym. Chem., 2015, 6, 2108
    DOI: 10.1039/C4PY01613K

Search articles by author

Spotlight

Advertisements