Naphthalimide-Tertiary Amine Derivatives as Blue-Light-Sensitive Photoinitiators

Jing Zhang (1) , Nicolas Zivic (2) , Frédéric Dumur (2) , Pu Xiao (1) , Bernadette Graff (1) , Jean Pierre Fouassier (1) , Didier Gigmes (2) , Jacques Lalevee (1)

1 IS2M - Institut de Science des Matériaux de Mulhouse
2 ICR - Institut de Chimie Radicalaire

The photochemical mechanism of the radical generation from photoinitiating systems based on 1, 8-naphthalimide derivatives (ANDs; with tertiary amine moieties) are investigated by using various approaches including cyclic voltammetry, steady-state photolysis, and electron spin resonance spin-trapping techniques. It reveals that radicals can be produced from ANDs alone or ANDs/additive (e.g. iodonium salt or chloro triazine) combinations. The generated radicals and cations can initiate both free-radical and cationic photopolymerization reactions under irradiation with various light-emitting diodes or a halogen lamp. For most of the AND-based photoinitiating systems, more than 60% of acrylate or epoxide conversions were attained, and were even higher than those obtained by using commercial photoinitiators, for example, bisacylphosphine oxide or camphorquinone. More interestingly, the AND1-based photoinitiating system can also initiate concomitant cationic/radic al polymerizations and can be used for the synthesis of interpenetrated polymer networks.

Mots clés: cationic photopolymerization; cationic-polymerization; curcumin; interpenetrated polymer networks; kinetics; laser flash-photolysis; light-emitting diodes; naphthalimide derivatives; photochemistry; photoinitiators; photophysical properties; photopolymerization; polymerization reactions; radical photopolymerization; versatile photoinitiators; visible lights

Domaines: Chimie

Jing Zhang, Nicolas Zivic, Frédéric Dumur, Pu Xiao, Bernadette Graff, et al.. Naphthalimide-Tertiary Amine Derivatives as Blue-Light-Sensitive Photoinitiators. ChemPhotoChem, 2018, 2 (6), pp.481--489. ⟨10.1002/cptc.201800006⟩. ⟨hal-02091858⟩