A multifunctionalized macromolecular silicone-naphthalimide visible photoinitiator for free radical polymerization

Multifunctionalization strategy in the photoinitiator design keeps in step with the requirement of the green chemistry in photopolymerization techniques. Therefore, a multifunctional macromolecular silicone-naphthalimide visible photoinitiator (SND) has been designed and prepared by a convenient thermal polymerization process of 441,3-dioxo-6-(piperidin-1-yl)-1H-benzo[de]isoquinolin-2(3H)-yl)phenyl acrylate (ND-PA) and 3-bis (trimethylsilyoxy)methylsiyl-propylmethacrylate (TSMSPM). Its structure has been confirmed by H-1 NMR, C-13 NMR, FT-IR and GPC analysis. On one hand, SND has been evidenced as a visible photoinitiator by its successfully initiating the free radical polymerization of acrylate monomers in the presence or absence of a hydrogen donor under the irradiation of different LEDs (405 nm, 455 nm and 470 nm). Furthermore, SND/MDEA (N-methyldiethanolamine) system shows higher photoinitiating activity than that of the commercial CQ (camphorquinone)/MDEA system. On the other hand, this multifunctionalization strategy also brings about some desired modification for cured-materials. After employing only 5 wt% SND as the photoinitiator, for example, a photo-cured film of urethane diacrylate prepolymer (PUA) increases its water contact angles from 70.1 degrees to 101.2 degrees, implying that SND could change the surface property of the PUA cured film from hydrophilic to hydrophobic. Meanwhile, the use of SND as an initiator could significantly improve the resistance against water and ethanol. When the mass fraction of SND increases to 15%, the water and ethanol absorption ratios of the cured PUA films decrease from 4.4% to 1.0% and 8.9% to 2.8%, respectively.