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Artículo

New copolymers of a tautomerizable beta-ketonitrile monomer: synthesis, characterization and solution tautomerism

Giussi, Juan MartínIcon ; Allegretti, Patricia Ercilia; Cortizo, Maria SusanaIcon
Fecha de publicación: 10/2012
Editorial: Wiley
Revista: Journal Of Polymer Science Part A: Polymer Chemistry
ISSN: 0887-624X
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Físico-Química, Ciencia de los Polímeros, Electroquímica

Resumen

The monomer 2-methyl-3-oxo-5-phenyl-4-pentenonitrile (MOP) was prepared by reaction of ethyl cinnamate and propionitrile in alkaline mixture. This monomer exhibits three possible tautomeric forms. The tautomeric equilibria of MOP and its copolymers with styrene in different solvents were analyzed by 1H NMR spectroscopy. The bulk and solution radical copolymerization behavior initiated with azobisisobutyronitrile was carried out at 60 ºC. The products were characterized by 1H NMR, 13C NMR, HSQC NMR, HMBC NMR and FTIR spectroscopies. The average molecular weight and polydispersity index were analyzed with size exclusion chromatography (SEC). The monomer reactivity ratios were obtained with the Fineman-Ross method, obtaining a value of r1r2 = 0.301. MOP copolymer composition as well as the nature of the solvent significantly affected the tautomeric equilibrium. Regression analysis of the copolymer composition with solvatochromic parameters showed a good linear correlation, as quantitatively expressed by means of the linear salvation energy relationship using the empirical set of Kamlet-Taft solvent parameters. This behavior could be attributed to polymer-polymer or polymer-solvent interactions prevalent in solvents of different polarity, which are responsible for changes in macromolecular chain conformations, as confirmed by FTIR and viscometric studies.
Palabras clave: Radical Polymerization , Beta-Ketonitrile , Tautomeric Equilibria , Nmr And Ftir Spectroscopies , Viscosity
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info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/5463
URL: http://onlinelibrary.wiley.com/doi/10.1002/pola.26238/abstract
DOI: http://dx.doi.org/10.1002/pola.26238
DOI: http://dx.doi.org/ 10.1002/pola.26238
Colecciones
Articulos(CCT - LA PLATA)
Articulos de CTRO.CIENTIFICO TECNOL.CONICET - LA PLATA
Articulos(INIFTA)
Articulos de INST.DE INV.FISICOQUIMICAS TEORICAS Y APLIC.
Citación
Giussi, Juan Martín; Allegretti, Patricia Ercilia; Cortizo, Maria Susana; New copolymers of a tautomerizable beta-ketonitrile monomer: synthesis, characterization and solution tautomerism; Wiley; Journal Of Polymer Science Part A: Polymer Chemistry; 50; 20; 10-2012; 4161-4169
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