110782-91-7Relevant academic research and scientific papers
Novel monovinyl methacrylic monomers containing secondary functionality for ultrarapid polymerization: Steady-state evaluation
Berchtold, Kathryn A.,Nie, Jun,Stansbury, Jeffrey W.,Hacioglu, Bilge,Beckel, Eric R.,Bowman, Christopher N.
, p. 3165 - 3179 (2004)
Experimental investigations were made into the effects of monomer structure and functionality on free-radical polymerization kinetics. A more comprehensive understanding of how structural characteristics, monomer traits, and polymerization conditions influence the polymerization mechanisms and network evolution was desired. Variations in the nature of the monomers' secondary functionality and the terminal substitution were the primary variables examined. The three factors hypothesized as important to the advantageous polymerization characteristics observed are hydrogen bonding, hydrogen abstraction, and the electronic characteristics of the monomer. The experimental evaluations presented clearly demonstrate that each of these mechanisms contributes to the reactivity of these monomers and the networks that they form. The combination of these factors leads to cross-linked network formation and enhanced polymerization kinetics, i.e., monovinyl monomers with reactivities that rival those of commonly used divinyl monomers.
Synthesis and photopolymerization of novel, highly reactive phosphonated-urea-methacrylates for dental materials
Altin, Ayse,Akgun, Burcin,Buyukgumus, Ozlem,Bilgici, Zeynep Sarayli,Agopcan, Sesil,Asik, Didar,Acar, Havva Yagci,Avci, Duygu
, p. 1319 - 1326 (2013)
An urea methacrylate (1) and two phosphonated methacrylates (2-3) were synthesized from 2-isocyanatoethyl methacrylate (IEM) and benzyl amine (1), diethyl aminomethylphosphonate (2) and diethyl amino(phenyl)methylphosphonate (3). Their photopolymerization rates are notably higher than commercial monomers, despite the presence of only one double bond. Their polymerization rates follow the order 1 ～ 2 > 3 ～ triethylene glycol dimethacrylate (TEGDMA) > 2-hydroxyethyl methacrylate (HEMA). A tendency toward high crosslinking density during thermal bulk polymerizations, low oxygen sensitivity and high conversions with benzophenone during photopolymerization indicated the importance of hydrogen abstraction/chain transfer reactions. It was found that the addition of the monomers to HEMA significantly increased its polymerization rate, proving their utility as replacements for TEGDMA as reactive diluents for 2,2-bis[4-(2-hydroxy-3-methacryloyloxy propyloxy) phenyl] propane (Bis-GMA). Copolymer systems containing 2 and 3 showed improved Tg values compared to Bis-GMA/ TEGDMA systems.
