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Development of Reactive Phosphonated Methacrylates

Edizer, Seda; Sahin, Gorkem; Avci, Duygu


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{
  "DOI": "10.1002/pola.23618", 
  "abstract": "Five novel phosphonated mono- and dimethacrylate monomers have been synthesized by two different routes. Monomers 1 and 2 were synthesized by reactions of methacryloyl chloride with diethyl (2-hydroxyphenyl) phosphonate or tetraethyl (2,5-dihydroxy-1,4-phenylene) bisphosphonate; monomers 3 and 4 by reactions of alpha-(chloromethyl)acryloylchloride (CMAC) first with dimethyl (2-hydroxyethyl) phosphonate and then with benzoic or formic acids. The reaction of CMAC with two moles of dimethyl (2-hydroxyethyl) phosphonate gave monomer 5. Thermal homopolymerization of monomers 1, 3, 4, and 5 and copolymerization of monomer 1 with methyl methacrylate (MMA) were investigated using azobisisobutyronitrile (AIBN) at 60 degrees C. Glass transition temperatures were observed for poly-1, poly(MMA-co-1) (50:50), poly(MMA-co-1) (90:10), PMMA, poly-3, and poly-5 at 52, 90, 99, 129, 50, and 70 degrees C, respectively. TGA analysis of these polymers indicated formation of char on combustion. Homo- and/or copolymerization behavior of the synthesized monomers with 2,2-bis[4-(2-hydroxy-3-methaeryloyloxy propyloxy) phenyl] propane (Bis-GMA) were investigated with photodifferential scanning calorimetry. The maximum rate of polymerizations decreased in the following order: Bis-GMA similar to 3 > 1 > 4 > 5. The conversions of monomers 1, 3, 4, and 5 (73.9, 85.9, 98.2, and 62.2%) were very high compared with Bis-GMA (40.5%). (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 5737-5746, 2009", 
  "author": [
    {
      "family": "Edizer", 
      "given": " Seda"
    }, 
    {
      "family": "Sahin", 
      "given": " Gorkem"
    }, 
    {
      "family": "Avci", 
      "given": " Duygu"
    }
  ], 
  "container_title": "JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY", 
  "id": "37179", 
  "issue": "21", 
  "issued": {
    "date-parts": [
      [
        2009, 
        1, 
        1
      ]
    ]
  }, 
  "page": "5737-5746", 
  "title": "Development of Reactive Phosphonated Methacrylates", 
  "type": "article-journal", 
  "volume": "47"
}
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