Coumarin derivatives as dual photo/thermal initiators for free radical polymerization and 3D printing,Polymer Chemistry

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Coumarin derivatives as dual photo/thermal initiators for free radical polymerization and 3D printing
Polymer Chemistry ( IF 4.1 ) Pub Date : 2024-05-24 , DOI: 10.1039/d4py00485j
Tong Gao _{1,

2} , Fabrice Morlet-Savary _{1,

2} , Bernadette Graff _{1,

2} , Frédéric Dumur ₃ , Jing Zhang ₄ , Pu Xiao ₅ , Jacques Lalevée _{1,

2}

Affiliation

In this study, five coumarin derivatives (Coums) were developed and synthesized to serve as visible light photoinitiators for the free radical photopolymerization of acrylates upon irradiation with a 405 nm LED. Their photoinitiating abilities were compared to that of a commercial photoinitiator, ketocoumarin (KC). By incorporating the ethyl 4-(dimethylamino)benzoate (EDB)/di-tert-butylphenyliodonium hexafluoro-phosphate (Iod) combination into the photoinitiating system, some of the resulting three-component Coums/EDB/Iod systems could lead to higher photopolymerization conversions than that obtained with the reference KC/EDB/Iod system. Parallel to their photoinitiating abilities, the different compounds also possess excellent thermal initiation capabilities, allowing their use as dual photo/thermal initiators. A comprehensive investigation of the photochemical mechanism was conducted utilizing various experimental techniques, including steady state photolysis, fluorescence quenching, cyclic voltammetry, and electron spin resonance spin trapping. Due to their excellent photoinitiation performance, the Coums/EDB/Iod combinations were successfully applied to 3D printing using different printing technologies.

中文翻译：

香豆素衍生物作为自由基聚合和 3D 打印的双光/热引发剂

在这项研究中，开发并合成了五种香豆素衍生物 (Coums)，作为可见光光引发剂，在 405 nm LED 照射下进行丙烯酸酯的自由基光聚合。将它们的光引发能力与商业光引发剂酮香豆素 (KC) 进行比较。通过将 4-(二甲基氨基)苯甲酸乙酯 (EDB)/二叔丁基苯基碘鎓六氟磷酸酯 (Iod) 组合纳入光引发体系中，所得的一些三组分 Coums/EDB/Iod 体系可以带来更高的光聚合转化率比参考 KC/EDB/Iod 系统获得的结果。除了光引发能力之外，不同的化合物还具有优异的热引发能力，使其可以用作光/热双重引发剂。利用稳态光解、荧光猝灭、循环伏安法和电子自旋共振自旋捕获等各种实验技术对光化学机制进行了全面研究。由于其优异的光引发性能，Coums/EDB/Iod组合成功应用于使用不同打印技术的3D打印。

更新日期：2024-05-29

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