Azide/Alkyne‐“Click”‐Reactions of Encapsulated Reagents: Toward Self‐Healing Materials
- 17 January 2011
- journal article
- Published by Wiley in Macromolecular Rapid Communications
- Vol. 32 (5), 419-425
- https://doi.org/10.1002/marc.201000687
Abstract
The successful encapsulation of reactive components for the azide/alkyne-"click"-reaction is reported featuring for the first time the use of a liquid polymer as reactive component. A liquid, azido-telechelic three-arm star poly(isobutylene) (M(n) = 3900 g · mol⁻¹) as well as trivalent alkynes were encapsulated into micron-sized capsules and embedded into a polymer-matrix (high-molecular weight poly(isobutylene), M(n) = 250,000 g · mol⁻¹). Using (Cu(I)Br(PPh₃)₃) as catalyst for the azide/alkyne-"click"-reaction, crosslinking of the two components at 40 °C is observed within 380 min and as fast as 10 min at 80 °C. Significant recovery of the tensile storage modulus was observed in a material containing 10 wt.-% and accordingly 5 wt.-% capsules including the reactive components within 5 d at room temperature, thus proving a new concept for materials with self-healing properties.This publication has 45 references indexed in Scilit:
- Masked Cyanoacrylates Unveiled by Mechanical ForceJournal of the American Chemical Society, 2010
- Polymers react to stressNature, 2009
- “Click” Chemistry in Macromolecular SynthesisPublished by Wiley ,2009
- ‘Click’ Chemistry in Polymer and Material Science: An UpdateMacromolecular Rapid Communications, 2008
- Self-Healing Polymeric Materials Using Epoxy/Mercaptan as the HealantMacromolecules, 2008
- Click chemistry in materials synthesis. III. Metal‐adhesive polymers from Cu(I)‐catalyzed azide–alkyne cycloadditionJournal of Polymer Science Part A: Polymer Chemistry, 2007
- ‘Click’ Chemistry in Polymer and Materials ScienceMacromolecular Rapid Communications, 2007
- Mechanism of the Ligand‐Free CuI‐Catalyzed Azide–Alkyne Cycloaddition ReactionAngewandte Chemie-International Edition, 2005
- Self-repairing mechanism of plasticsScience and Technology of Advanced Materials, 2003
- A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal AlkynesAngewandte Chemie, 2002