Synthesis and Polymerizations of Six Aminophosphonate-Containing Methacrylates

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dc.authoridDEMIR-ORDU, Oznur/0000-0002-5647-7559
dc.authoridIsik Bennett, Mehtap/0000-0002-6789-952X
dc.contributor.authorBilgici, Zeynep Sarayli
dc.contributor.authorOrdu, Oznur Demir
dc.contributor.authorIsik, Mehtap
dc.contributor.authorAvci, Duygu
dc.date.accessioned2024-09-29T15:50:50Z
dc.date.available2024-09-29T15:50:50Z
dc.date.issued2011
dc.departmentKarabük Üniversitesien_US
dc.description.abstractTwo different groups of novel aminophosphonate-containing methacrylates were synthesized. The route to the first group involves reactions of ethyl alpha-bromomethacryate (EBBr) and t-butyl alpha-bromomethacryate (TBBr) with diethyl aminomethylphosphonate and diethyl 2-aminoethylphosphonate. Bulk and solution polymerizations at 60-80 degrees C with 2,2'-azobis(isobutyronitrile) (AIBN) gave crosslinked or soluble polymers depending on monomer structure and polymerization conditions. Increasing bulkiness from ethyl to t-butyl decreases the polymerization rate, correlated well with the chemical shift differences of double bond carbons and consistent with the lower molecular weights of t-butyl ester polymers (M(n) 1800-7900 vs. 50,000-72,000). The route to the second group involves the Michael addition reaction between diethyl aminomethylphosphonate and diethyl 2-aminoethylphosphonate with 3-(acryloyloxy)-2-hydroxypropyl methacrylate (AHM) to give secondary amines. The photopolymerization using differential scanning calorimeter showed that these monomers have similar or higher reactivities than AHM, even though AHM has two double bonds. The high rates of polymerization of these monomers were attributed to both hydrogen bonding interactions due to additional NH groups as well as chain transfer reactions. All the homopolymers obtained produced char (17-35%) on combustion. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 5042-5048, 2011en_US
dc.description.sponsorshipBogazici University [5697]en_US
dc.description.sponsorshipFinancial support by Bogazici University Research Fund (5697) is gratefully acknowledged.en_US
dc.identifier.doi10.1002/pola.24965
dc.identifier.endpage5048en_US
dc.identifier.issn0887-624X
dc.identifier.issue23en_US
dc.identifier.scopus2-s2.0-80054985602en_US
dc.identifier.scopusqualityN/Aen_US
dc.identifier.startpage5042en_US
dc.identifier.urihttps://doi.org/10.1002/pola.24965
dc.identifier.urihttps://hdl.handle.net/20.500.14619/3738
dc.identifier.volume49en_US
dc.identifier.wosWOS:000297456700014en_US
dc.identifier.wosqualityQ1en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherWiley-Blackwellen_US
dc.relation.ispartofJournal of Polymer Science Part A-Polymer Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectaminophosphonatesen_US
dc.subjectalkyl alpha-bromomethacrylatesen_US
dc.subjectcyclopolymerizationen_US
dc.subjectradical polymerizationen_US
dc.subjectphotopolymerizationen_US
dc.titleSynthesis and Polymerizations of Six Aminophosphonate-Containing Methacrylatesen_US
dc.typeArticleen_US

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