Abstract:
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.
Registro:
Documento: |
Artículo
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Título: | Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol |
Autor: | Fidalgo, D.M.; Kolender, A.A.; Varela, O. |
Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
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Palabras clave: | 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 |
Año: | 2013
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Volumen: | 51
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Número: | 2
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Página de inicio: | 463
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Página de fin: | 470
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DOI: |
http://dx.doi.org/10.1002/pola.26406 |
Título revista: | Journal of Polymer Science, Part A: Polymer Chemistry
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Título revista abreviado: | J Polym Sci Part A
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ISSN: | 0887624X
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CODEN: | JPACE
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0887624X_v51_n2_p463_Fidalgo |
Referencias:
- Jayabalan, M., Lizymol, P.P., Thomas, V., (2000) Polym. Int., 49, pp. 88-92
- Galbis, J.A., García-Martín, M.G., (2010) Top. Curr. Chem., 295, pp. 147-176
- Van De Manakker, F., Vermonden, T., Van Nostrum, C.F., Hennink, W.E., (2009) Biomacromolecules, 10, pp. 3157-3175
- Okada, M., (2002) Prog. Polym. Sci., 27, pp. 87-133
- Varela, O., Orgueira, H.A., (1999) Adv. Carbohydr. Chem. Biochem., 55, pp. 137-174
- Paz, M.V., Marín, R., Zamora, F., Hakkou, K., Alla, A., Galbis, J.A., Muñoz-Guerra, S., (2007) J. Polym. Sci. Part A: Polym. Chem., 45, pp. 4109-4117
- Paz, M.V., Aznar, J.A., Galbis, J.A., (2008) J. Carbohydr. Chem., 27, pp. 120-140
- Marín, R., Muñoz-Guerra, S., (2008) J. Polym. Sci. Part A: Polym. Chem., 46, pp. 7996-8012
- Marín, R., Paz, M.V., Ittobane, N., Galbis, J.A., Muñoz-Guerra, S., (2009) Macromol. Chem. Phys., 210, pp. 486-494
- De Paz, M.V., Zamora, F., Begines, B., Ferris, C., Galbis, J.A., (2010) Biomacromolecules, 11, pp. 269-276
- Ferris, C., Violante De Paz, M., Zamora, F., Galbis, J.A., (2010) Polym. Degrad. Stab., 95, pp. 1480-1487
- Ferris, C., De Paz, M.V., Galbis, J.A., (2011) J. Polym. Sci. Part A: Polym. Chem., 49, pp. 1147-1154
- Begines, B., Zamora, F., Roffé, I., Mancera, M., Galbis, J.A., (2011) J. Polym. Sci. Part A: Polym. Chem., 49, pp. 1953-1961
- Ferris, C., De Paz, M.V., Galbis, J.A., (2012) Macromol. Chem. Phys., 213, pp. 480-488
- Marín, R., Muñoz-Guerra, S., (2009) J. Appl. Polym. Sci., 114, pp. 3723-3736
- Marín, R., Alla, A., Martínez De Ilarduya, A., Muñoz-Guerra, S., (2012) J. Appl. Polym. Sci., 123, pp. 986-994
- Marín, R., De Ilarduya, A.M., Muñoz-Guerra, S., (2012) J. Polym. Sci. Part A: Polym. Chem., 123, pp. 986-994
- Garçon, R., Clerk, C., Gesson, J.-P., Bordado, J., Nunes, T., Caroço, S., Gomes, P.T., Rauter, A.P., (2001) Carbohydr. Polym., 45, pp. 123-127
- Hashimoto, K., Yaginuma, K., Nara, S.-I., Okawa, H., (2005) Polym. J., 37, pp. 384-390
- Hashimoto, K., Wibullcksanakul, S., Okada, M., (1995) J. Polym. Sci. Part A: Polym. Chem., 33, pp. 1495-1503
- Yamanaka, C., Hashimoto, K., (2002) J. Polym. Sci. Part A: Polym. Chem., 40, pp. 4158-4166
- Thiem, J., Luders, H., (1986) Makromol. Chem., 187, pp. 2775-2785
- Bachmann, F., Reimer, J., Ruppenstein, M., Thiem, J., (1998) Macromol. Rapid Commun., 19, pp. 21-26
- Bachmann, F., Ruppenstein, M., Thiem, J., (2001) J. Polym. Sci. Part A: Polym. Chem., 39, pp. 2332-2341
- Ubaghs, L., Fricke, N., Keul, H., Höcker, H., (2004) Macromol. Rapid Commun., 25, pp. 517-521
- Prömpers, G., Keul, H., Höcker, H., (2005) Des. Monomers Polym., 8, pp. 547-569
- Prömpers, G., Keul, H., Höcker, H., (2006) Green Chem., 8, pp. 467-478
- Gomez, R.V., Varela, O., (2009) Macromolecules, 42, pp. 8112-8117
- Arce, S.M., Kolender, A.A., Varela, O., (2010) Polym. Int., 59, pp. 1212-1220
- Kolender, A.A., Arce, S.M., Varela, O., (2011) Carbohydr. Res., 346, pp. 1398-1405
- Crombez-Robert, C., Benazza, M., Fréchou, C., Demailly, G., (1997) Carbohydr. Res., 303, pp. 359-365
- Glaçon, V., Benazza, M., El Anzi, A., Beaupère, D., Demailly, G., (2004) J. Carbohydr. Chem., 23, pp. 95-110
- Mancera, M., Roffé, I., Rivas, M., Silva, C., Galbis, J.A., (2002) Carbohydr. Res., 337, pp. 607-611
- Mancera, M., Roffé, I., Rivas, M., Silva, C., Galbis, J.A., (2003) Carbohydr. Res., 338, pp. 1115-1119
- Le Merrer, Y., Duréault, A., Greck, C., Micas-Languin, D., Gravier, C., Depezay, J.-C., (1987) Heterocycles, 25, pp. 541-548
- Le Merrer, Y., Gauzy, L., Gravier-Pelletier, C., Depezay, J.-C., (2000) Bioorg. Med. Chem., 8, pp. 307-320
- Fitremann, J., Duréault, A., Depezay, J.-C., (1994) Tetrahedron Lett., 35, pp. 1201-1204
- Nazhaoui, M., Joly, J.P., Kitane, S., Berrada, M., (1998) J. Chem. Soc. Perkin Trans. 1, 22, pp. 3845-3850
- Rokicki, G., Piotrowska, A.J., (2002) Polymer, 43, pp. 2927-2935
- Versteegen, R.M., Sijbesma, R.P., Meijer, E.W., (1999) Angew. Chem. Int. Ed. Engl., 38, pp. 2917-2919
- Deepa, P., Jayakannan, M., (2008) J. Polym. Sci. Part A: Polym. Chem., 46, pp. 2445-2458
Citas:
---------- APA ----------
Fidalgo, D.M., Kolender, A.A. & Varela, O.
(2013)
. Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol. Journal of Polymer Science, Part A: Polymer Chemistry, 51(2), 463-470.
http://dx.doi.org/10.1002/pola.26406---------- CHICAGO ----------
Fidalgo, D.M., Kolender, A.A., Varela, O.
"Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol"
. Journal of Polymer Science, Part A: Polymer Chemistry 51, no. 2
(2013) : 463-470.
http://dx.doi.org/10.1002/pola.26406---------- MLA ----------
Fidalgo, D.M., Kolender, A.A., Varela, O.
"Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol"
. Journal of Polymer Science, Part A: Polymer Chemistry, vol. 51, no. 2, 2013, pp. 463-470.
http://dx.doi.org/10.1002/pola.26406---------- VANCOUVER ----------
Fidalgo, D.M., Kolender, A.A., Varela, O. Stereoregular poly-O-methyl [m,n]-polyurethanes derived from D-mannitol. J Polym Sci Part A. 2013;51(2):463-470.
http://dx.doi.org/10.1002/pola.26406