Synthesis and modeling of new phosphorus-containing acrylates

Salman S., Albayrak A., Avci D., Aviyente V.

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, cilt.43, sa.12, ss.2574-2583, 2005 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 43 Sayı: 12
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1002/pola.20733
  • Dergi Adı: JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED)
  • Sayfa Sayıları: ss.2574-2583
  • Anahtar Kelimeler: adhesives, dental polymers, modeling, photopolymerization, radical polymerization, synthesis, ETHYL ALPHA-HYDROXYMETHYLACRYLATE, RADICAL POLYMERIZATION, AB-INITIO, PREDICTING REACTIVITY, ADHESIVE POLYMERS, MONOMERS, DIALLYLAMINE, CYCLOPOLYMERIZATION, COPOLYMERIZATION, KINETICS
  • Dokuz Eylül Üniversitesi Adresli: Hayır

Özet

New methacrylate monomers containing phosphonic acid or both phosphonic and carboxylic acids were synthesized through the reaction of t-butyl alpha-bromomethyl acrylate with triethyl phosphite followed by the selective hydrolysis of the phosphonate or t-butyl ester groups with trimethylsilyl bromide and trifluoroacetic acid. The copolymerization of these monomers with 2-hydroxyethylmethacrylate was investigated with photodifferential scanning calorimetry at 40 degrees C with 2,2 '-dimethoxy-2-phenyl acetophenone as a photoinitiator. Quantum mechanical tools were also used to understand the mechanistic behavior of the polymerization reactions of these synthesized monomers. The propagation and chain-transfer reactions were considered and rationalized. A strong effect of the monomer structure on the rate of polymerization was observed. The polymerization reactivities of the monomers increased with decreasing steric hindrance and/or increasing hydrogen-bonding capacity because of the hydrolysis of the phosphonate and the t-butyl ester groups. (c) 2005 Wiley Periodicals, Inc.