Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose
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...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_20462069_v9_n17_p9860_Rivas |
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todo:paper_20462069_v9_n17_p9860_Rivas2023-10-03T16:38:40Z Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose Rivas, M.V. Petroselli, G. Erra-Balsells, R. Varela, O. Kolender, A.A. Copper compounds Degradation Monomers Polymerization Chemical degradation Cycloaddition polymerization Degradable polymers Degradation products Environmentally benign High molecular weight Polymerization conditions Random distribution Esters 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_20462069_v9_n17_p9860_Rivas |
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Universidad de Buenos Aires |
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I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Copper compounds Degradation Monomers Polymerization Chemical degradation Cycloaddition polymerization Degradable polymers Degradation products Environmentally benign High molecular weight Polymerization conditions Random distribution Esters |
| spellingShingle |
Copper compounds Degradation Monomers Polymerization Chemical degradation Cycloaddition polymerization Degradable polymers Degradation products Environmentally benign High molecular weight Polymerization conditions Random distribution Esters 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 |
| topic_facet |
Copper compounds Degradation Monomers Polymerization Chemical degradation Cycloaddition polymerization Degradable polymers Degradation products Environmentally benign High molecular weight Polymerization conditions Random distribution Esters |
| description |
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. |
| format |
JOUR |
| author |
Rivas, M.V. Petroselli, G. Erra-Balsells, R. Varela, O. Kolender, A.A. |
| author_facet |
Rivas, M.V. Petroselli, G. Erra-Balsells, R. Varela, O. Kolender, A.A. |
| author_sort |
Rivas, M.V. |
| title |
Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose |
| title_short |
Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose |
| title_full |
Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose |
| title_fullStr |
Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose |
| title_full_unstemmed |
Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose |
| title_sort |
synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose |
| url |
http://hdl.handle.net/20.500.12110/paper_20462069_v9_n17_p9860_Rivas |
| work_keys_str_mv |
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1807322184772747264 |