Study of Reactivity of 3-[{Oxiran-2-yl)methoxy}methyl]-9-ethyl-9H-carbazole in Cationic Photopolymerization

Abstract

A new monomer, 3-[{(oxiran-2-yl)methoxy}methyl]-9-ethyl-9H-carbazole (OMEC), was synthesized by the reaction of 9-ethyl-3-(hydroxymethyl)carbazole with (1-chloromethyl)oxirane in the presence of KOH. Cationic photopolymerization of OMEC initiated with diphenyliodonium tetrafluoroborate (DPIB), cyclopropyldiphenylsulfonium tetrafluoroborate (CPB) and (η ⁵-2,4-cyclopentadien-1-yl) [(1,2,3,4,5-η)-(1-methylethyl) benzene]-iron (+)-hexafluorophosphate (–1) (Irgacure 261) was studied. The initiator exponent was established for the photopolymerization of OMEC initiated with DPIB. The influence of the temperature and oxidizing agent benzoyl peroxide on the polymerization rate and the conversion limit of OMEC photopolymerization initiated with Irgacure 261 is discussed. An activation energy value of 17 kJ/mol was estimated for OMEC when photopolymerization was initiated with Irgacure 261. Post-polymerization reactions of OMEC were studied.

Keywords:

• PHOTOPOLYMERIZATION
• EPOXIDE
• CARBAZOLE
• IODONIUM SALTS
• SULFONIUM SALTS
• IRON ARENE COMPLEX