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Nitro-Carbazole Based Oxime Esters as Dual Photo/Thermal Initiators for 3D Printing and Composite Preparation.

Authors
  • Liu, Shaohui1, 2
  • Graff, Bernadette1, 2
  • Xiao, Pu3
  • Dumur, Frédéric4
  • Lalevée, Jacques1, 2
  • 1 Université de Haute-Alsace, CNRS, IS2M UMR 7361, Mulhouse, F-68100, France. , (France)
  • 2 Université de Strasbourg, France. , (France)
  • 3 Research School of Chemistry, Australian National University, Canberra, ACT 2601, Australia. , (Australia)
  • 4 Aix Marseille University, CNRS, ICR UMR 7273, Marseille, F-13397, France. , (France)
Type
Published Article
Journal
Macromolecular rapid communications
Publication Date
Aug 01, 2021
Volume
42
Issue
15
Identifiers
DOI: 10.1002/marc.202100207
PMID: 33938080
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

A series of Type I photoinitiators (PIs) based on a nitrocarbazole scaffold are developed and examined for the first time as photoinitiators for visible light photopolymerization. Three oxime esters (OXE-M, OXE-V, OXE-P) varying by the terminal groups (acetyl, acryloyl and benzoyl) attached via the oxime ester group are originally prepared. As a result of this, the three PIs exhibit excellent photoinitiation abilities in the presence of acrylate monomers upon [email protected] 405 nm irradiation. Markedly, OXE-M exhibits a better performance than the benchmark Type I phosphine-oxide (diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide TPO). Chemical mechanisms supporting the polymerization process with these PIs are investigated by steady state photolysis, molecular orbital calculations and real-time Fourier transformed infrared spectroscopy. After the cleavage of N─O bond and decarboxylation, free radicals are generated to initiate the free radical polymerization efficiently. Free radical photopolymerization of OXE-M is applied in direct laser write and 3D printing. Interestingly, OXE-M exhibits thermal initiation behaviors in monomers and can be used as dual photo and thermal initiators. The highly opaque feature of carbon fibers makes it difficult for light penetration, so dual photo/thermal curing are used here to prepare carbon fiber composites. © 2021 Wiley-VCH GmbH.

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