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Synthesis and evaluation of new phosphonic acid-functionalized acrylamides with potential biomedical applications

Bingol, H. Betul; Altin, Ayse; Bal, Tugba; Agopcan-Cinar, Sesil; Kizilel, Seda; Avci, Duygu


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{
  "DOI": "10.1002/pola.27746", 
  "abstract": "Phosphorus-containing acidic monomers are able to interact with the inorganic phase of mineralized tissues such as enamel, dentin, and bone. From this perspective, three phosphonic acid-containing acrylamide monomers with different lengths of alkyl chains were synthesized to be used for both self-etching dental adhesives and mineralized hydrogel scaffolds. Monomers were synthesized by the reaction of -aminophosphonates (diethyl aminomethylphosphonate, diethyl 2-aminobutan-2-ylphosphonate, and diethyl 2-aminooctan-2-ylphosphonate) with acryloyl chloride followed by the hydrolysis of phosphonate groups by using trimethylsilyl bromide. The properties such as pH in the range of mild self-etching adhesives, hydrolytic stability, high rate of copolymerizations with 2-hydroxyethyl methacrylate (HEMA) and HEMA/glycerol dimethacrylate, giving high-molecular-weight polymers on thermal polymerization, and strong decalcification ability of hydroxyapatite make these monomers good candidates for self-etching adhesives, although no appreciable effect of the number and size of the -substituents was observed. Hydrogel scaffolds containing phosphonic acid groups were fabricated, characterized, and mineralized. Altogether, the results suggest that these phosphonic acid-containing monomers have suitable properties to be used in fabrication of biomaterials for both dental and bone tissue engineering applications. (c) 2015 Wiley Periodicals, Inc.", 
  "author": [
    {
      "family": "Bingol", 
      "given": " H. Betul"
    }, 
    {
      "family": "Altin", 
      "given": " Ayse"
    }, 
    {
      "family": "Bal", 
      "given": " Tugba"
    }, 
    {
      "family": "Agopcan-Cinar", 
      "given": " Sesil"
    }, 
    {
      "family": "Kizilel", 
      "given": " Seda"
    }, 
    {
      "family": "Avci", 
      "given": " Duygu"
    }
  ], 
  "container_title": "JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY", 
  "id": "78891", 
  "issue": "23", 
  "issued": {
    "date-parts": [
      [
        2015, 
        1, 
        1
      ]
    ]
  }, 
  "page": "2755-2767", 
  "title": "Synthesis and evaluation of new phosphonic acid-functionalized acrylamides with potential biomedical applications", 
  "type": "article-journal", 
  "volume": "53"
}
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