Blue Light Sensitive Dyes for Various Photopolymerization Reactions: Naphthalimide and Naphthalic Anhydride Derivatives

Novel naphthalimide derivatives (or naphthalic anhydride derivatives) have been prepared and combined with an iodonium salt, N-vinylcarbazole, amines or 2,4,6-tris(trichloromethyl)-1,3,5-triazine to produce radicals and cations upon exposure to low intensity blue lights (e.g., a household blue LED b...

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Bibliographic Details
Published in:Macromolecules 2014-01, Vol.47 (2), p.601-608
Main Authors: Xiao, Pu, Dumur, Frédéric, Graff, Bernadette, Gigmes, Didier, Fouassier, Jean Pierre, Lalevée, Jacques
Format: Article
Language:English
Subjects:
Applied sciences
Chemical Sciences
Exact sciences and technology
Material chemistry
Physicochemistry of polymers
Polymerization
Polymers
Polymers and radiations
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Summary:Novel naphthalimide derivatives (or naphthalic anhydride derivatives) have been prepared and combined with an iodonium salt, N-vinylcarbazole, amines or 2,4,6-tris(trichloromethyl)-1,3,5-triazine to produce radicals and cations upon exposure to low intensity blue lights (e.g., a household blue LED bulb). The photochemical mechanisms are studied by electron spin resonance spin trapping, fluorescence, cyclic voltammetry, laser flash photolysis, and steady state photolysis techniques. The naphthalimide derivatives (ND4) or the naphthalic anhydride derivative (ND10) based photoinitiating systems are particularly efficient for cationic, radical and thiol–ene photopolymerizations; the synthesis of interpenetrated polymer networks IPNs can also be easily carried out. Compared to camphorquinone/amine or camphorquinone/iodonium salt, the new proposed combinations appear as highly versatile and high performance visible light photoinitiating systems. Some of these photoinitiating systems can also be used for UV LED irradiations (e.g., 365, 385, or 395 nm).
ISSN:0024-9297
1520-5835
DOI:10.1021/ma402376x