Synthesis and modeling of new phosphorus-containing acrylates
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, vol.43, no.12, pp.2574-2583, 2005 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 43 Issue: 12
- Publication Date: 2005
- Doi Number: 10.1002/pola.20733
- Journal Name: JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Page Numbers: pp.2574-2583
- Keywords: adhesives, dental polymers, modeling, photopolymerization, radical polymerization, synthesis
- Dokuz Eylül University Affiliated: No
Abstract
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.