Biobased imine vitrimers obtained by photo and thermal curing procedures-promising materials for 3D printing
Imine-based vitrimers were prepared from synthesized diimine-dimethacrylate monomer derived from biobased vanillin. First, a methacrylate derivative starting from vanillin was synthesized. The diimine derivative was synthesized by condensation of the aldehyde groups from two vanillin methacrylate un...
| Autores: | , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2024 |
| País: | España |
| Institución: | Universitat Politècnica de Catalunya (UPC) |
| Repositorio: | UPCommons. Portal del coneixement obert de la UPC |
| Idioma: | inglés |
| OAI Identifier: | oai:upcommons.upc.edu:2117/405472 |
| Acceso en línea: | https://hdl.handle.net/2117/405472 https://dx.doi.org/10.1021/acsapm.3c03234 |
| Access Level: | acceso abierto |
| Palabra clave: | Three-dimensional printing Materials science Chemistry, Organic Vitrimer Imine metathesis 3D printing Vanillin Methacrylate Impressió 3D Ciència dels materials Química orgànica Àrees temàtiques de la UPC::Enginyeria dels materials |
| Sumario: | Imine-based vitrimers were prepared from synthesized diimine-dimethacrylate monomer derived from biobased vanillin. First, a methacrylate derivative starting from vanillin was synthesized. The diimine derivative was synthesized by condensation of the aldehyde groups from two vanillin methacrylate units with the amine groups of hexamethylenediamine (HMDA). The synthesized product was used in formulations containing ethylene glycol phenyl ether methacrylate (EGPMA) as a reactive diluent for the customization of final material properties and cured by exposure to ultraviolet (UV)-light using suitable radical photoinitiators or else with temperature using a radical thermal initiator. Materials with glass transition temperatures (Tgs) ranging from 70 to 90 °C were prepared, showing good thermal stability and mechanical and thermomechanical properties. The evaluation of their vitrimeric characteristics revealed that all materials achieved a stress-relaxation factor (s = 0.37s0) in less than 130 s at 160 °C, with photocured materials exhibiting faster relaxation rates. The catalytic effect of phosphine oxide groups in imine metathesis has also been evidenced. All prepared materials could be mechanically recycled and completely solubilized in a two-step degradation process, putting evidence of their potential use for carbon fiber-reinforced composites (CFRCs). In addition, they demonstrated promising self-repairing abilities. Finally, as a proof of concept, it was established that these formulations could be effectively processed using a Digital Light Processing three-dimensional (3D) Printer (DLP), resulting in the fabrication of complex shapes with high resolution. |
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