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
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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
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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
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Volumen: | 9
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Número: | 17
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Página de inicio: | 9860
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Página de fin: | 9869
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DOI: |
http://dx.doi.org/10.1039/C9RA00398C |
Título revista: | RSC Advances
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Título revista abreviado: | RSC Adv.
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ISSN: | 20462069
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CODEN: | RSCAC
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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