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

• Published in: Designed monomers and polymers Vol. 12; no. 4; pp. 331 - 342
• Main Authors: Sakalyte, A., Lazauskaite, R., Simokaitiene, J., Buika, G., Grazulevicius, J. V.
• Format: Journal Article
• Language: English
• Published: Leiden Taylor & Francis Group 01.01.2009; Brill
• Subjects: Applied sciences; CARBAZOLE; EPOXIDE; Exact sciences and technology; IODONIUM SALTS; IRON ARENE COMPLEX; PHOTOPOLYMERIZATION; Physicochemistry of polymers; Polymerization; Polymers and radiations; SULFONIUM SALTS; Cationic complex; Ring opening polymerization; iodonium salts; Bulk polymerization; Priming activity; Cationic polymerization; Experimental study; Reaction rate; Chemical reaction kinetics; iron arene complex; Sandwich compound; Iron complex; Photopolymerization; Iodonium compounds; Carbazole derivative polymer; Epoxide; sulfonium salts; carbazole; Glycidyl ether polymer; Monomer; Chemical reactivity; Sulfonium compound; Activation energy; Comparative study
• ISSN: 1385-772X; 1568-5551; 1568-5551
• DOI: 10.1163/156855509X448307

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.