| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1398270 | European Polymer Journal | 2012 | 12 Pages |
The first step in the synthesis of functionalized polyamides consisted in the introduction of alkyne side groups in several types of linear polyamides by interfacial step-growth polymerization of hexane-1,6-diamine or 4,9-dioxadodecane-1,12-diamine in combination with on one hand adipoyl or sebacoyl chloride and on the other hand an alkyne-containing building block, i.e. 2-methyl-2-propargylmalonic acid dichloride. Both homo- and copolyamides were synthesized, creating a large range of alkyne-containing polyamides with degrees of functionalization ranging between 5% and 100%. Subsequently, these polyamide chains have been modified with two types of linking chemistries, respectively with azides through the copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition or with thiols through the thiol-yne addition reaction.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Linear, aliphatic polyamides containing alkyne functional groups were prepared via step-growth polymerization. ► Homo- and copolyamides were synthesized without protection or deprotection steps. ► The polyamides were functionalized using the Cu(I)-catalyzed azide-alkyne cycloaddition and thiol-yne reaction. ► The thermal properties before and after functionalization were investigated.
