Dynamic Curing Agents for Amine-Hardened Epoxy Vitrimers with Short (Re)processing Times

被引:120
作者
Spiesschaert, Yann [1 ,2 ]
Guerre, Marc [1 ,2 ,3 ]
Baere, Ives De [4 ]
Van Paepegem, Wim [4 ]
Winne, Johan M. [1 ,2 ]
Du Prez, Filip E. [1 ,2 ]
机构
[1] Univ Ghent, Fac Sci, Dept Organ & Macromol Chem, Polymer Chem Res Grp, B-9000 Ghent, Belgium
[2] Univ Ghent, Fac Sci, Dept Organ & Macromol Chem, Lab Organ Synth, B-9000 Ghent, Belgium
[3] Univ Paul Sabatier, CNRS, Lab IMRCP, Univ Toulouse,UMR5623, F-31062 Toulouse 9, France
[4] Univ Ghent, Dept Mat Text & Chem Engn, B-9052 Zwijnaarde, Belgium
关键词
MECHANICAL-PROPERTIES; OXIRANE RINGS; EPOXIDATION; CHEMISTRY; NETWORKS; DESIGN; RESINS;
D O I
10.1021/acs.macromol.9b02526
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
This work presents a straightforward strategy to introduce highly dynamic and adaptable cross-links into common epoxy resin formulations. For this, an oligomeric amine-based curing agent containing vinylogous urethane (VU) bonds was developed. This novel polyfunctional amine curing agent can be used as a drop-in solution for existing epoxy resin technologies, resulting in transparent, rigid, and, at the same time, highly reprocessable catalyst-free epoxy vitrimers. The oligomeric VU-curing agents are prepolymerized via a straightforward condensation reaction between acetoacetates extended with different classical amine monomers and epoxy hardeners. It is found that vitrimer properties can be readily introduced into these epoxy formulations by converting <50 mol % of the hardener's amine functionalities into dynamic vinylogous urethane bonds. In this way, epoxy vitrimers can be obtained with material properties comparable to ones of the VU-free epoxy formulations. In addition, remarkably short processing times are observed in the absence of any catalyst, and the material displayed very short stress relaxation times and good recyclability, actually representing the most performant VU-based vitrimers so far. Furthermore, a proof of concept for its use in obtaining glass-fiber-reinforced epoxy composites is also presented.
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页码:2485 / 2495
页数:11
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