Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol
Novel linear carbohydrate-derived [m,n]-polyurethanes are successfully prepared using D-mannitol as renewable and low cost starting material. The key comonomer, 1,6-di-O-phenylcarbonyl-2,3,4,5-tetra-O-methyl-D-mannitol is polymerized with a diamine synthesized from D-mannitol or with alkylenediamine...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_0887624X_v51_n2_p463_Fidalgo |
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todo:paper_0887624X_v51_n2_p463_Fidalgo2023-10-03T15:41:00Z Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol Fidalgo, D.M. Kolender, A.A. Varela, O. biodegradable biomaterials carbohydrates D -mannitol polyurethanes Axis of symmetry biodegradable Carbohydrate derivatives Co-monomer D-mannitol FTIR GPC analysis Low costs Optically Active Polymerization reaction Polymethylene chain Standard method Stereoregular Thermal study Weight-average molecular weight Biological materials Biomaterials Carbohydrates Drug products Polymers Polyurethanes Novel linear carbohydrate-derived [m,n]-polyurethanes are successfully prepared using D-mannitol as renewable and low cost starting material. The key comonomer, 1,6-di-O-phenylcarbonyl-2,3,4,5-tetra-O-methyl-D-mannitol is polymerized with a diamine synthesized from D-mannitol or with alkylenediamines. These polymerization reactions afford, respectively, a [6,6]-polyurethane entirely based on a carbohydrate derivative or [m,n]-polyurethanes constituted by a poly-O-methyl substituted unit alternating with a polymethylene chain. All these polymers are stereoregular, as result of the C2 axis of symmetry of mannitol. The optically active polyurethanes are characterized by standard methods (FTIR, RMN, GPC, TGA, and DSC). Thus, GPC analysis reveals weight-average molecular weights between 18,000 and 25,000 Da. Thermal studies (DSC) indicate that the polymers obtained are amorphous materials with T g values dependent on the structure and chain length of the diamine constituent. © 2012 Wiley Periodicals, Inc. Fil:Kolender, A.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0887624X_v51_n2_p463_Fidalgo |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
biodegradable biomaterials carbohydrates D -mannitol polyurethanes Axis of symmetry biodegradable Carbohydrate derivatives Co-monomer D-mannitol FTIR GPC analysis Low costs Optically Active Polymerization reaction Polymethylene chain Standard method Stereoregular Thermal study Weight-average molecular weight Biological materials Biomaterials Carbohydrates Drug products Polymers Polyurethanes |
| spellingShingle |
biodegradable biomaterials carbohydrates D -mannitol polyurethanes Axis of symmetry biodegradable Carbohydrate derivatives Co-monomer D-mannitol FTIR GPC analysis Low costs Optically Active Polymerization reaction Polymethylene chain Standard method Stereoregular Thermal study Weight-average molecular weight Biological materials Biomaterials Carbohydrates Drug products Polymers Polyurethanes Fidalgo, D.M. Kolender, A.A. Varela, O. Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol |
| topic_facet |
biodegradable biomaterials carbohydrates D -mannitol polyurethanes Axis of symmetry biodegradable Carbohydrate derivatives Co-monomer D-mannitol FTIR GPC analysis Low costs Optically Active Polymerization reaction Polymethylene chain Standard method Stereoregular Thermal study Weight-average molecular weight Biological materials Biomaterials Carbohydrates Drug products Polymers Polyurethanes |
| description |
Novel linear carbohydrate-derived [m,n]-polyurethanes are successfully prepared using D-mannitol as renewable and low cost starting material. The key comonomer, 1,6-di-O-phenylcarbonyl-2,3,4,5-tetra-O-methyl-D-mannitol is polymerized with a diamine synthesized from D-mannitol or with alkylenediamines. These polymerization reactions afford, respectively, a [6,6]-polyurethane entirely based on a carbohydrate derivative or [m,n]-polyurethanes constituted by a poly-O-methyl substituted unit alternating with a polymethylene chain. All these polymers are stereoregular, as result of the C2 axis of symmetry of mannitol. The optically active polyurethanes are characterized by standard methods (FTIR, RMN, GPC, TGA, and DSC). Thus, GPC analysis reveals weight-average molecular weights between 18,000 and 25,000 Da. Thermal studies (DSC) indicate that the polymers obtained are amorphous materials with T g values dependent on the structure and chain length of the diamine constituent. © 2012 Wiley Periodicals, Inc. |
| format |
JOUR |
| author |
Fidalgo, D.M. Kolender, A.A. Varela, O. |
| author_facet |
Fidalgo, D.M. Kolender, A.A. Varela, O. |
| author_sort |
Fidalgo, D.M. |
| title |
Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol |
| title_short |
Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol |
| title_full |
Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol |
| title_fullStr |
Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol |
| title_full_unstemmed |
Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol |
| title_sort |
stereoregular poly-o-methyl [m,n]-polyurethanes derived from d-mannitol |
| url |
http://hdl.handle.net/20.500.12110/paper_0887624X_v51_n2_p463_Fidalgo |
| work_keys_str_mv |
AT fidalgodm stereoregularpolyomethylmnpolyurethanesderivedfromdmannitol AT kolenderaa stereoregularpolyomethylmnpolyurethanesderivedfromdmannitol AT varelao stereoregularpolyomethylmnpolyurethanesderivedfromdmannitol |
| _version_ |
1807317138026790912 |