Publication:
Synthesis and photopolymerizations of first monomers with phosphonate and bisphosphonate or phosphonic and bisphosphonic acid functionalities for potential dental applications

dc.contributor.coauthorGencoglu, Turkan
dc.contributor.coauthorOlcay, Keziban
dc.contributor.departmentDepartment of Chemistry
dc.contributor.departmentGraduate School of Sciences and Engineering
dc.contributor.kuauthorAcar, Havva Funda Yağcı
dc.contributor.kuauthorDuman, Fatma Demir
dc.contributor.schoolcollegeinstituteCollege of Sciences
dc.contributor.schoolcollegeinstituteGRADUATE SCHOOL OF SCIENCES AND ENGINEERING
dc.date.accessioned2024-11-10T00:00:58Z
dc.date.issued2018
dc.description.abstractThe first monomers containing both phosphonate and bisphosphonate (M1) or phosphonic and bisphosphonic acid (M2) functionalities are synthesized, aiming to improve binding abilities of self-etching adhesive systems and composites: An amine having both phosphonate and bisphosphonate functionalities is prepared via Michael addition reaction between diethyl (6-aminohexyl)phosphonate and tetraethyl vinylidene bisphosphonate, its reaction with 2-isocyanatoethyl methacrylate gives M1 which is converted to M2 by selective dealkylation of the phosphonate/bisphosphonate ester groups. Their copolymerization with commercial dental monomers (bisphenol A glycidyl methacrylate, triethylene glycol dimethacrylate, and 2-hydroxyethyl methacrylate) investigated by photo-differential scanning calorimetry shows adequate photopolymerization rate and conversion. X-ray diffraction, Fourier transform infrared, and X-ray photoelectron spectroscopy analyses of M2-treated hydroxyapatite particles show formation of stable M2-calcium salts. These monomers are assessed to be not toxic according to MTT standards by in vitro cytotoxicity studies with NIH 3T3, U2OS, and Saos-2 cells. All these properties make these monomers potential candidates as biocompatible components for dental adhesives and composites. (c) 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 2739-2751
dc.description.indexedbyWOS
dc.description.indexedbyScopus
dc.description.issue24
dc.description.openaccessNO
dc.description.publisherscopeInternational
dc.description.sponsoredbyTubitakEuN/A
dc.description.sponsorshipThis research has been financially supported by The Scientific and Technological Research Council of Turkey (TUBITAK
dc.description.sponsorship215Z060) and Bogazici University Research Fund (11680). The authors would like to thank Ozlem Karahan for XRD measurements.
dc.description.volume56
dc.identifier.doi10.1002/pola.29260
dc.identifier.eissn1099-0518
dc.identifier.issn0887-624X
dc.identifier.scopus2-s2.0-85055252272
dc.identifier.urihttps://doi.org/10.1002/pola.29260
dc.identifier.urihttps://hdl.handle.net/20.500.14288/15878
dc.identifier.wos450460600005
dc.keywordsBisphosphonic acid
dc.keywordsDental adhesive
dc.keywordsHydroxyapatite
dc.keywordsPhotopolymerization
dc.keywordsPhosphonate
dc.language.isoeng
dc.publisherWiley
dc.relation.ispartofJournal Of Polymer Science Part A-Polymer Chemistry
dc.subjectPolymer science
dc.titleSynthesis and photopolymerizations of first monomers with phosphonate and bisphosphonate or phosphonic and bisphosphonic acid functionalities for potential dental applications
dc.typeJournal Article
dspace.entity.typePublication
local.contributor.kuauthorAcar, Havva Funda Yağcı
local.contributor.kuauthorDuman, Fatma Demir
local.publication.orgunit1College of Sciences
local.publication.orgunit1GRADUATE SCHOOL OF SCIENCES AND ENGINEERING
local.publication.orgunit2Department of Chemistry
local.publication.orgunit2Graduate School of Sciences and Engineering
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