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Synthesis and photopolymerization of novel, highly reactive phosphonated-urea-methacrylates for dental materials

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Altin, Ayse
Akgun, Burcin
Buyukgumus, Ozlem
Bilgici, Zeynep Sarayli
Agopcan, Sesil
Avci, Duygu

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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 similar to 2 > 3 similar to 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 T-g values compared to Bis-GMA/TEGDMA systems. (C) 2013 Elsevier Ltd. All rights reserved.

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Elsevier Science Bv

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Chemistry, Applied chemistry, Engineering, Chemical engineering, Polymer science

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Reactive & Functional Polymers

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10.1016/j.reactfunctpolym.2013.07.006

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