Abstract
In this article, we report the synthesis of poly(oxanorbornene imide) (PONB) with internal epoxy groups (epoxidized-PONB30) and its ring-opening reactions with various nucleophiles, such as amine, azide, and thiols. The ring-opening reactions with amines yielded the amine-hydroxyl PONBs in the range of 36-95% of functionalization depending upon the amine content per epoxy. An allylamine-hydroxyl functionalized PONB was further functionalized efficiently with 1-octanethiol by radical thiol-ene reaction. The ring-opening reaction of the main chain epoxy using thiols resulted in a lower functionalization than amines with a similar functional group (e.g., allyl). In addition, sodium azide together with NH4Cl, was employed efficiently in the ring-opening reaction of the main chain epoxy, resulting in an azide/hydroxyl-functional PONB30 with 53% efficiency, which was determined after a model copper-catalyzed azide-alkyne cycloaddition (CuAAC) experiment was carried out.
Original language | English |
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Pages (from-to) | 35-42 |
Number of pages | 8 |
Journal | Reactive and Functional Polymers |
Volume | 94 |
DOIs | |
Publication status | Published - 27 Jul 2015 |
Bibliographical note
Publisher Copyright:© 2015 Elsevier B.V. All rights reserved.
Keywords
- Amine-epoxy ring-opening reaction
- Backbone epoxidation
- Poly(oxanorbornene imide) (PONB)
- Ring-opening metathesis polymerization (ROMP)
- Thiol-epoxy ring-opening reaction