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Abstract:

α-Azide-ω-alkynyl ester monomers were designed and synthesized in order to obtain hydrolytically degradable polymers. The monomers were prepared from d-galactose, as a renewable resource. Environmentally benign azido-alkyne cycloaddition polymerizations were conducted to afford poly(ester-triazole)s, with complete atom economy. Although polymer formation prevailed under optimized polymerization conditions, variable proportions of cyclic oligomer byproducts were detected. The Cu-catalyzed click polymerization led regioselectively to 1,4-disubstituted triazole linkages, while the thermal, metal-free polymerization produced a random distribution of 1,4- and 1,5-disubstituted triazoles in the polymer backbone. The poly(ester-triazole)s exhibited high molecular weights (M w in the range 35-85 kDa). They were soluble in organic solvents but highly insoluble in water, thus removal of the Cu(i) catalyst was simplified. The polymers were stable up to 300 °C, and had T g values in the range 90-100 °C. The materials were hydrolysed under either basic or strong acid conditions, and the degradation products have been characterized. © The Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose
Autor:Rivas, M.V.; Petroselli, G.; Erra-Balsells, R.; Varela, O.; Kolender, A.A.
Filiación:Universidad de Buenos Aires, Facultad Ciencias Exactas y Naturales, Departamento de Química Orgánica, Ciudad Universitaria, Pab. 2, Buenos Aires, C1428EHA, Argentina
Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), UBA Centro de Investigación en Hidratos de Carbono (CIHIDECAR), Argentina
Palabras clave:Copper compounds; Degradation; Monomers; Polymerization; Chemical degradation; Cycloaddition polymerization; Degradable polymers; Degradation products; Environmentally benign; High molecular weight; Polymerization conditions; Random distribution; Esters
Año:2019
Volumen:9
Número:17
Página de inicio:9860
Página de fin:9869
DOI: http://dx.doi.org/10.1039/C9RA00398C
Título revista:RSC Advances
Título revista abreviado:RSC Adv.
ISSN:20462069
CODEN:RSCAC
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20462069_v9_n17_p9860_Rivas

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Citas:

---------- APA ----------
Rivas, M.V., Petroselli, G., Erra-Balsells, R., Varela, O. & Kolender, A.A. (2019) . Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose. RSC Advances, 9(17), 9860-9869.
http://dx.doi.org/10.1039/C9RA00398C
---------- CHICAGO ----------
Rivas, M.V., Petroselli, G., Erra-Balsells, R., Varela, O., Kolender, A.A. "Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose" . RSC Advances 9, no. 17 (2019) : 9860-9869.
http://dx.doi.org/10.1039/C9RA00398C
---------- MLA ----------
Rivas, M.V., Petroselli, G., Erra-Balsells, R., Varela, O., Kolender, A.A. "Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose" . RSC Advances, vol. 9, no. 17, 2019, pp. 9860-9869.
http://dx.doi.org/10.1039/C9RA00398C
---------- VANCOUVER ----------
Rivas, M.V., Petroselli, G., Erra-Balsells, R., Varela, O., Kolender, A.A. Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose. RSC Adv. 2019;9(17):9860-9869.
http://dx.doi.org/10.1039/C9RA00398C