Disubstituted Aminoanthraquinone-Based Photoinitiators for Free Radical Polymerization and Fast 3D Printing under Visible Light

• Published in: Macromolecules 2018-12, Vol.51 (24), p.10104-10112
• Main Authors: Zhang, J, Launay, K, Hill, N. S, Zhu, D, Cox, N, Langley, J, Lalevée, J, Stenzel, M. H, Coote, M. L, Xiao, P
• Format: Article
• Language: English
• ISSN: 0024-9297; 1520-5835
• DOI: 10.1021/acs.macromol.8b02145

The development of highly efficient and rapid photoinitiating systems for free radical photopolymerization under the irradiation of visible light has attracted increasing attention due to their widespread potential applications in, for example, 3D printing or dental polymers. Unfortunately, currently available visible-light-sensitive photoinitiators are not efficient enough for 3D printing applications suffering from low printing speeds. Here we describe a series of photoinitiating systems consisting of disubstituted amino­anthraquinone derivatives (i.e., 1-amino-4-hydroxy­anthraquinone, 1,4-diamino­anthraquinone, and 1,5-diamino­anthraquinone) and various additives (e.g., tertiary amine and phenacyl bromide) toward the free radical photopolymerization of various acrylate monomers (such as commercial 3D resin) under the irradiation of blue to red LEDs. It is shown that the type and position of substituents of the amino­anthraquinone derivative can significantly affect its photoinitiation properties. The most efficient disubstituted amino­anthraquinone derivative-based photoinitiating system was selected and used for the 3D printing of a commercial 3D resin in a 3D printer with polychromatic visible light as the irradiation source. It is shown that its printing speed was dramatically enhanced compared to a commercial photoinitiator 2,4,6-trimethyl­benzoyldiphenyl­phosphine oxide (TPO).