A Single Molecular Diels-Alder Crosslinker for Achieving Recyclable Cross-Linked Polymers

A triol‐functional crosslinker combining the thermoreversible properties of Diels–Alder (DA) adducts in one molecule is designed, synthesized, and used as an ideal substitute of a traditional crosslinker to prepare thermal recyclable cross‐linked polyurethanes with excellent mechanical properties an...

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Bibliographic Details
Published in:Macromolecular rapid communications. 2015-09, Vol.36 (18), p.1687-1692
Main Authors: Chen, Shengli, Wang, Fenfen, Peng, Yongjin, Chen, Tiehong, Wu, Qiang, Sun, Pingchuan
Format: Article
Language:English
Subjects:
Adducts
Calorimetry
Chemical synthesis
Cross-Linking Reagents
Crosslinking
Cycloaddition Reaction
Diels-Alder reactions
Differential scanning calorimetry
Elongation
Furans
Injection molding
Mechanical properties
Nanotechnology
NMR
Nuclear magnetic resonance
Polymers
Polymers - chemistry
Polyurethane
Polyurethane resins
Polyurethanes - chemistry
Recyclability
recycle
Recycled
Recycling
single molecular crosslinkers
Thermal cycling
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Summary:A triol‐functional crosslinker combining the thermoreversible properties of Diels–Alder (DA) adducts in one molecule is designed, synthesized, and used as an ideal substitute of a traditional crosslinker to prepare thermal recyclable cross‐linked polyurethanes with excellent mechanical properties and recyclability in a very simple and efficient way. The recycle property of these materials achieved by the DA/retro‐DA reaction at a suitable temperature is verified by differential scanning calorimetry and in situ variable temperature solid‐state NMR experiments during the cyclic heating and cooling processes. The thermal recyclability and remending ability of the bulk polyurethanes is demonstrated by three polymer processing methods, including hot‐press molding, injection molding, and solution casting. It is notable that all the recycled cross‐linked polymers display nearly invariable elongation/stress at break compared to the as‐synthesized samples. Further end‐group functionalization of this single molecular DA crosslinker provides the potential in preparing a wide range of recyclable cross‐linked polymers. A single molecular Diels–Aldercrosslinker integrating furan and maleic moieties is used to crosslink isocyanate‐terminated polyurethane under mild conditions by a simple and solvent‐free method. The prepared cross‐linked polyurethanes with excellent mechanical properties are thermally recycled by three polymer processing methods, including injection molding, hot‐press molding, and solution casting.
ISSN:1022-1336
1521-3927
DOI:10.1002/marc.201500257