Visible-light initiator system using thiobarbituric acid derivatives with methyl substituent

Abstract

Seven 2-thiobarbituric acid derivatives with methyl substituents were synthesized. Experimental visible-light curing resins were prepared using these compounds as a reducing agent in the dl-camphorquinone (CQ)-reducing agent initiator system. The effects of methyl substitution for thiobarbituric acid on initiation behavior of CQ-thiobarbituric acid initiator system were examined by analysis of polymerization of triethylene glycol dimethacrylate (3 G) in DSC and depth of cure. The solubility of thiobarbituric acid derivatives in 3 G was markedly changed by the introduction of the methyl group. Although the methyl group substitution at position 1 (3) in thiobarbituric acid improved the solubility of the acid in 3 G, it did not enhance the initiation ability. Maximum exothermic rate, time at maximum exothermic peak, amount of insufficiently polymerized layer and depth of cure were significantly improved by the introduction of one methyl group at the position 5. Thus the initiation ability was enhanced by the substitution. However, the introduction of two methyl groups at position 5 did not promote polymerization, but the inhibitory effect became apparent as the concentration of the reducing agent was increased.