Towards safe phosphine oxides photoinitiators with good cytocompatibility for 3D printing of thermoplastics
Résumé
3D printing is the technology of choice for the rapid production of objects withcomplex morphologies and controlled physical and chemical properties. 3D print-ing by photopolymerization is of great interest because of its ability to access verysmall scales and its high resolution. In thecaseofrecent3Dprinters, the preferredwavelength for light irradiation is 405 nmsince it is a safe and energy-economicalirradiation. For 3D printing to be effective,it is therefore necessary to develop eas-ily accessible, stable and highly efficient photoinitiating systems at the 405 nmwavelength. Beside, with the increasing use of photoinitiators, it is essential todevelop structures with low cytotoxicity. Hence, the development of new photoini-tiators is currently of major interest. To this end, the photochemical properties(triplet energy, bond dissociation energy,cleavage reaction enthalpy, and absorp-tion properties) of several molecules havebeen calculated by molecular modelingand the most promising compounds havebeen synthesized. In this paper, fourphosphine oxides photoinitiators (ADPO-1, CPO-2, CPO-3, and FPO-1) aresynthesized and characterized. Subsequently, their absorption properties are mea-sured and their efficiencies in photopolymerization under LED irradiation at405 nm are evaluated. It is important to note that these structures have neverbeen reported in 3D printing. Markedly, among the obtained photoinitiators, twoof them show better efficiency than the commercially available and widely usedphenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (BAPO) in photopolymeriza-tion (i.e., (Rp/[M0]) x100 values are 6.94, 12.95, and 4.93 s1for CPO-2, ADPO-1,and BAPO; with [M0] the initial acrylate function concentration). Furthermore,one of the synthesized photoinitiators is successfully used in 3D printing ofthermoplastics for potential recycling ability. Finally, one of the obtainedstructures shows a lower cytotoxicity than the benchmark structurediphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO)
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