Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes
Aliphatic [n]-polyurethanes have recently been synthesized from ω-isocyanato-α-alkanols or, more traditionally, by cationic ring-opening polymerization of cyclourethanes or by the Bu2Sn(OMe)2-promoted polycondensation of ω-hydroxy-α-O- phenylurethane alkanes. For the latter procedures, the condition...
Guardado en:
| Autor principal: | |
|---|---|
| Otros Autores: | , |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2010
|
| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 06802caa a22009497a 4500 | ||
|---|---|---|---|
| 001 | PAPER-7668 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203726.0 | ||
| 008 | 190411s2010 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-77956607405 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Arce, S.M. | |
| 245 | 1 | 0 | |a Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes |
| 260 | |c 2010 | ||
| 270 | 1 | 0 | |m Varela, O.; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: varela@qo.fcen.uba |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Król, P., (2007) Prog Mater Sci, 52, pp. 915-1015 | ||
| 504 | |a Nair, L.S., Laurencin, C.T., (2007) Prog Polym Sci, 32, pp. 762-798 | ||
| 504 | |a Chattopadhyay, D.K., Raju, K.V.S.N., (2007) Prog Polym Sci, 32, pp. 352-418 | ||
| 504 | |a Wolinska-Grabczyk, A., Muszynski, J., Penczek, P., (1997) Polimery, 42, pp. 55-58 | ||
| 504 | |a Li, W., Pham, H.H., Nie, Z., MacDonald, B., Güenther, A., Kumacheva, E.J., (2008) J Am Chem Soc, 130, pp. 9935-9941 | ||
| 504 | |a Poussard, L., Burel, F., Couvercelle, J.P., Merhi, Y., Tabrizian, M., Bunel, C., (2004) Biomaterials, 25, pp. 3473-3483 | ||
| 504 | |a Dieter, J.A., Frisch, K.C., Wolgemuth, L.G., (1975) J Paint Technol, 47, pp. 65-70 | ||
| 504 | |a Rokicki, G., Piotrowska, A., (2002) Polymer, 43, pp. 2927-2935 | ||
| 504 | |a Kihara, N., Kushida, Y., Endo, T., (1996) J Polym Sci A: Polym Chem, 34, pp. 2173-2179 | ||
| 504 | |a Deepa, P., Jayakannan, (2008) J Polym Sci A: Polym Chem, 46, pp. 2445-2458 | ||
| 504 | |a Matsumura, S., Soeda, Y., Toshima, K., (2006) Appl Microbiol Biotechnol, 70, pp. 12-20 | ||
| 504 | |a Versteegen, R.M., Sijbesma, R.P., Meijer, E.W., (1999) Angew Chem Int Ed, 38, pp. 2917-2919 | ||
| 504 | |a Hall H.K., Jr., (1958) J Am Chem Soc, 80, pp. 6412-6420 | ||
| 504 | |a Kušan, J., Keul, H., Höcker, H., (2001) Macromolecules, 34, pp. 389-395. , and references therein | ||
| 504 | |a Neffgen, S., Kušan, J., Fey, T., Keul, H., Höcker, H., (2000) Macromol Chem Phys, 201, pp. 2108-2114 | ||
| 504 | |a Varela, O., Orgueira, H.A., (2000) Adv Carbohydr Chem Biochem, 55, pp. 137-174 | ||
| 504 | |a Orgueira, H.A., Varela, O., (2001) J Polym Sci A: Polym Chem, 39, pp. 1024-1030 | ||
| 504 | |a Romero Zaliz, C.L., Varela, O., (2003) Tetrahedron: Asym, 14, pp. 2579-2586 | ||
| 504 | |a Romero Zaliz, C.L., Varela, O., (2005) Tetrahedron: Asym, 16, pp. 97-103 | ||
| 504 | |a Gómez, R.V., Kolender, A.A., Varela, O., (2006) Carbohydr Res, 341, pp. 1498-1504 | ||
| 504 | |a Gómez, R.V., Varela, O., (2007) Tetrahedron: Asym, 18, pp. 2190-2196 | ||
| 504 | |a Gibson, F.S., Bergmeier, S.C., Rapoport, H., (1994) J Org Chem, 59, pp. 3216-3218 | ||
| 504 | |a Prömpers, G., Keul, H., Höcker, H., (2006) Green Chem, 8, pp. 467-478 | ||
| 504 | |a Gresser, M.J., Jencks, W.P., (1977) J Am Chem Soc, 99, pp. 6970-6980 | ||
| 504 | |a Jacobi, E., Schuttenberg, H., Schultz, R.C., (1980) Makromol Chem Rapid Commun, 1, pp. 397-402 | ||
| 504 | |a Lebedev, B.V., Bykova, T.A., Kiparisova, E.G., Kochetkov, A.M., Höcker, H., Kušan, J., (1999) Macromol Chem Phys, 200, pp. 1863-1869 | ||
| 520 | 3 | |a Aliphatic [n]-polyurethanes have recently been synthesized from ω-isocyanato-α-alkanols or, more traditionally, by cationic ring-opening polymerization of cyclourethanes or by the Bu2Sn(OMe)2-promoted polycondensation of ω-hydroxy-α-O- phenylurethane alkanes. For the latter procedures, the conditions employed do not seem to be suitable for highly functionalized monomers. In contrast, the polymerization of ω-amino-α-phenylcarbonate alkanes is expected to occur under milder conditions. ω-Amino-α-phenylcarbonate alkanes have been synthesized from 6-aminohexanol (1) and 3-aminopropanol (6). The procedure involves the N-Boc protection of the amino group, followed by activation of the alcohol. Removal of the N-Boc affords the corresponding ω-amino-1-O-phenyloxycarbonyloxyalkane hydrochlorides. Other oligomeric comonomers between 1 and 6 have been prepared. The polymerization of these precursors takes place in the absence of metal catalysts to afford the corresponding linear and regioregular [n]-polyurethanes. The procedure described is useful for the preparation of stable ω-amino-α-phenylcarbonate alkane derivatives, which possess varied chain lengths between the terminal functions. These monomers yield [n]-polyurethanes having various structures starting from just two aminoalkanols. The polyurethanes were obtained in high yields, with reasonable molecular weight and polydispersity values, and they were characterized spectroscopically and thermally. These studies reveal constitutionally uniform structures that are free of carbonate or urea linkages. © 2010 Society of Chemical Industry. |l eng | |
| 593 | |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a Ω-AMINO-Α-PHENYLCARBONATE ALKANES |
| 690 | 1 | 0 | |a AMINOALKANOLS |
| 690 | 1 | 0 | |a POLYMERIZATION |
| 690 | 1 | 0 | |a POLYURETHANES |
| 690 | 1 | 0 | |a ALKANOLS |
| 690 | 1 | 0 | |a AMINO GROUP |
| 690 | 1 | 0 | |a AMINOALKANOLS |
| 690 | 1 | 0 | |a AMINOPROPANOL |
| 690 | 1 | 0 | |a BOC PROTECTION |
| 690 | 1 | 0 | |a CATIONIC RING OPENING POLYMERIZATION |
| 690 | 1 | 0 | |a COMONOMERS |
| 690 | 1 | 0 | |a FUNCTIONALIZED MONOMERS |
| 690 | 1 | 0 | |a HIGH YIELD |
| 690 | 1 | 0 | |a METAL CATALYST |
| 690 | 1 | 0 | |a REGIO-REGULAR |
| 690 | 1 | 0 | |a TERMINAL FUNCTIONS |
| 690 | 1 | 0 | |a UNIFORM STRUCTURE |
| 690 | 1 | 0 | |a CATALYSTS |
| 690 | 1 | 0 | |a CATIONIC POLYMERIZATION |
| 690 | 1 | 0 | |a MONOMERS |
| 690 | 1 | 0 | |a PARAFFINS |
| 690 | 1 | 0 | |a POLYCONDENSATION |
| 690 | 1 | 0 | |a POLYDISPERSITY |
| 690 | 1 | 0 | |a POLYMERS |
| 690 | 1 | 0 | |a POLYURETHANES |
| 690 | 1 | 0 | |a TIN |
| 690 | 1 | 0 | |a UREA |
| 690 | 1 | 0 | |a RING OPENING POLYMERIZATION |
| 700 | 1 | |a Kolender, A.A. | |
| 700 | 1 | |a Varela, O. | |
| 773 | 0 | |d 2010 |g v. 59 |h pp. 1212-1220 |k n. 9 |p Polym. Int. |x 09598103 |t Polymer International | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-77956607405&doi=10.1002%2fpi.2850&partnerID=40&md5=1f115dd4be95b9b283b1af39679a8c6a |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1002/pi.2850 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_09598103_v59_n9_p1212_Arce |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09598103_v59_n9_p1212_Arce |y Registro en la Biblioteca Digital |
| 961 | |a paper_09598103_v59_n9_p1212_Arce |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 999 | |c 68621 | ||