Novel ketone derivatives based photoinitiating systems for free radical polymerization under mild conditions and 3D printing

Yangyang Xu (1) , Guillaume Noirbent (2) , Damien Brunel (2) , Zhaofu Ding (1) , Didier Gigmes (2) , Yijun Zhang (1) , Shaohui Liu (1) , Bernadette Graff (1) , Pu Xiao (3) , Frédéric Dumur (2) , Jacques Lalevée (1)

1 IS2M - Institut de Science des Matériaux de Mulhouse
2 ICR - Institut de Chimie Radicalaire
3 ANU - Australian National University

Photopolymerization of acrylates under mild conditions is promising for not only academic research, but also for industrialization applications. However, it still remains a huge challenge to develop effective photoinitiators or photoinitiating systems for the free radical polymerization of acrylates upon visible light-emitting diode (LED) irradiation. In this work, twelve novel ketone derivatives containing either tertiary amines or anthracenes as peripheral substituting groups (noted as Ami-1~Ami-6 and Anth-1~Anth-6) were elaborately synthesized and proposed for the polymerization of di(trimethylolpropane) tetraacrylate (TA), a tetrafunctional polyether acrylate, in both thin and thick films conditions under the LED@405 nm irradiation. In combination with an amine and an iodonium salt (Iod), these ketones could form distinct three-component photoinitiating systems, among which the Ami-2/amine/Iod system could lead to the highest final conversion of acrylates in the thick film (~1.4 mm) condition while Ami-6/amine/Iod system could induce the highest final conversion of acrylates in the thin film (~25 μm) condition. Photosensitivity of Ami-2 and Ami-6 was systematically investigated by the steady state photolysis and fluorescence quenching experiments. Finally, photocuring 3D printing technique was applied to TA, and both Ami-2 and Ami-6 based photoinitiating systems could be used to fabricate macroscopically tridimensional patterns with excellent spatial resolution.

Domaines: Matériaux

Yangyang Xu, Guillaume Noirbent, Damien Brunel, Zhaofu Ding, Didier Gigmes, et al.. Novel ketone derivatives based photoinitiating systems for free radical polymerization under mild conditions and 3D printing. Polymer Chemistry, 2020, 11 (36), pp.5767-5777. ⟨10.1039/d0py00990c⟩. ⟨hal-02946028⟩