Related Experiment Video
Updated: Sep 8, 2025

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
Published on: August 25, 2016
Dynamic reversible adhesives based on crosslinking network via Schiff base and Michael addition
Junyu Ren1, Hongxing Yang1, Yingchen Wu1
1International Joint Research Center for Biomass Materials, Yunnan Province Key Lab of Wood Adhesives and Glued Products, Southwest Forestry University Kunming 650224 China guanben@swfu.edu.cn long133109070@126.com.
Abstract:
It is of practical interest to obtain polymers with complex material properties in a simplified synthetic manner for a broader range of practical applications. In this work, we constructed a dynamic reversible adhesive based on branched polyamine (PA) and p-formylphenyl acrylate (FPA) by simultaneously performing Michael addition reaction and Schiff base reaction. Branched polyamines provide a large number of amino groups as reaction sites that can react with both carbon-carbon double bonds and aldehyde groups. This enables the branched polymeric adhesive system to have a large number of Schiff base bonds within it, an important property of Schiff base bonds is that they are dynamically reversible. This allows us to prepare adhesives with hyperbranched crosslinking networks and recycling properties, and we have verified that FPA-PA adhesives do not exhibit significant fatigue after multiple recycling through the gluing-destruction-gluing process. The resulting FPA-PA adhesives produce tough bonding on multi-substrates such as steel, aluminum, glass, PVC, PTFE, birch and moso bamboo, which exhibited by lap shear strength of 2.4 MPa, 1.7 MPa, 1.4 MPa, 1.3 MPa, 0.4 MPa, 1.6 MPa, and 1.8 MPa, respectively. The feasibility of the synthesis idea of simultaneous Michael addition reaction and Schiff base reaction was demonstrated, as well as the excellent performance and great application potential of FPA-PA adhesives to be recyclable on multi-substrates.
More Related Videos
Related Concept Videos
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Anionic Chain-Growth Polymerization: Overview
Conjugate Addition of Enolates: Michael Addition
Cycloaddition Reactions: Overview
Anionic Chain-Growth Polymerization: Mechanism
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

