Issue 12, 2020

In silico rational design by molecular modeling of new ketones as photoinitiators in three-component photoinitiating systems: application in 3D printing

Abstract

One of the main challenges in the field of 3D printing/vat photopolymerization is the poor adaption of existing commercial photoinitiators (PIs) for the recently popular 3D printers with the irradiation wavelength at 405 nm. It is thus desirable to design and develop high-performance PIs which can work efficiently at this wavelength. In this work, different ketones were specifically designed by molecular modeling for good light absorption properties at 405 nm and the best theoretical structures showing intense violet/blue light absorption were synthesized for further investigation. The new proposed ketones were used in conjunction with different tertiary amines (e.g. ethyl dimethylaminobenzoate (EDB) or triethanolamine (TEA)) and iodonium salt as photoinitiating systems (PISs) for the photopolymerization of trimethylolpropane triacrylate (TMPTA) and Ebecryl 40 (a tetrafunctional polyether acrylate) via an oxidation–reduction reaction mechanism. The results demonstrate that several ketone-based PISs can initiate free radical photopolymerization. The final conversions of Ebecryl 40 resin are higher than those of TMPTA, particularly in the presence of TEA. In addition, the light absorption properties and the photoinitiation mechanisms are also studied using UV-Visible absorption spectra, cyclic voltammetry, and fluorescence approaches. Moreover, the formation of the radicals is clearly determined by the electron spin resonance (ESR) spin-trapping experiments. Finally, the developed ketone-based three-component systems are applied to the generation of macroscopically stereoscopic letter patterns using the 3D printing technique. This research is expected to offer some fresh insights into photopolymerization reactions with three-component photoinitiating systems used in 3D printing. All this work shows that the in silico rational design of new photoinitiators by molecular modeling for specific wavelength (here 405 nm) and specific applications is a powerful tool for the development of high performance photosensitive resins.

Graphical abstract: In silico rational design by molecular modeling of new ketones as photoinitiators in three-component photoinitiating systems: application in 3D printing

Supplementary files

Article information

Article type
Paper
Submitted
12 ডিসে. 2019
Accepted
15 ফেব্রু. 2020
First published
17 ফেব্রু. 2020

Polym. Chem., 2020,11, 2230-2242

In silico rational design by molecular modeling of new ketones as photoinitiators in three-component photoinitiating systems: application in 3D printing

K. Sun, Y. Xu, F. Dumur, F. Morlet-Savary, H. Chen, C. Dietlin, B. Graff, J. Lalevée and P. Xiao, Polym. Chem., 2020, 11, 2230 DOI: 10.1039/C9PY01874C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements