Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization

Abstract

In order to discuss the polymerization effect from the substituted position and methoxy group of Type I photinitiators, a series of naphthalene-based oxime esters was designed and synthesized. Compared to the 2-naphthalene-substituted compound, the UV absorption region of the 1-naphthalene-based compound was greatly improved. In addition, the methoxy substitution exhibited longer absorption characteristics than did the methoxy-free one. The photochemical reaction behavior of these novel compounds was also studied by photolysis, cyclic voltammetry (CV), and electron spin resonance (ESR) experiments. Finally, the initiation abilities of naphthalene-based oxime esters toward trimethylolpropane triacrylate (TMPTA) monomer were conducted through the photo-DSC instrument under UV and a 405@nm LED lamp. Remarkedly, the naphthalene-based oxime ester (NA-3) that contains 1-naphthalene with o-methoxy substituent showed the rather red-shifted absorption region with the highest final conversion efficiency under UV (46%) and 405@nm LED (41%) lamp irradiation.

Keywords

• free radical photopolymerization
• methoxy
• naphthalene
• oxime ester
• substitution
• Type I photoinitiator