Abstract
Optically active poly(imide-amide)s (PIAs) and poly(imide-ester)s (PIEs) containing two silicon atoms in the main chain and l-alanine as chiral residue, were synthesized. The former were prepared by direct polycondensation between two dicarboxilic acids and bis(4-aminophenyl)dipenylsilane according to the triphenyl phosphate method. PIEs were synthesized with bis(4-hydroxyphenyl)dimethyl o ethylmethylsilane, according to the tosyl chloride method. Monomers and polymers were characterized by IR and 1H, 13C, and 29Si NMR spectroscopy and elemental analysis, and the results were in agreement with the proposed structures. PIAs and PIEs showed low values of ηinh, indicative of low molecular weight species, probably of oligomeric nature. Polymers were soluble in polar aprotic solvents and also in common solvents such as CH2Cl2, CHCl3, and acetone, due to the effect of both, the polarity of the Si–C bond and the presence of an aliphatic residue provided by the l-alanine amino acid. The glass transition temperatures (T g) of the PIAs were higher than those obtained for PIEs, due to the higher flexibility of the ester group. The thermal decomposition temperatures (TDT) were lower than 400 °C and dependent of the polymer structure.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Ehsani S, Mehdipour-Atei S, Ali M (2011) Synthesis and characterization of novel optically active polyesters with high thermal stability. J Appl Polym Sci 120:2146–2153. doi:10.1002/app.33392
Eastmond GC, Paprotny J, Irwin RS (1996) Melt processable poly(ether-imide)s based on catechol bis(ether anhydride). Macromolecules 29:1382–1388. doi:10.1021/ma951007h
Bruma M, Schulz B (2001) Silicon-containing aromatic polymers. J Macromol Sci Polym Rev 41:1–40. doi:10.1081/MC-100002054
Mallakpour S, Zadehnazari A (2011) Advances in synthetic optically active condensation polymers—a review. Exp Polym Lett 5:142–181. doi:10.3144/expresspolymlett.com
Tagle LH, Terraza C, Leiva A, Yazigi N, Lopez L (2010) Poly(imide-amide)s and poly(imide-ester)s obtained from N,N′-(4, 4′-Me, R-diphthaloyl)-bis-glycine acid dichloride (R = Me, Et): synthesis, characterization, and thermal studies. J Appl Polym Sci 117:1526–1534. doi:10-1002/app.32007
Kovaks HN, Delman AD, Simms BB (1968) Silicon-containing amide benzimidazole hydrazide and oxadiazole polymers. J Polym Sci A-1 6: 2103–2115. doi:10.1002/pol.1968.150060808
Ghatge ND, Jadhav JY (1983) Preparation of silicon-containing polymers. I. Polyimides from dianhydrides and organosilicon diisocyanates. J Polym Sci Polym Chem Ed 21:3055–3061. doi:10.1002/pol1983.170211103
Tagle LH, Terraza CA, Leiva A, Valenzuela P (2006) Poly(amides) and poly(imides) containing silicon and germanium in the main chain:synthesis, characterization and termal studies. J Appl Polym Sci 102:2768–2776. doi:10.1002/app.24454
Tagle LH, Terraza CA, Leiva A, Devilat F (2008) Synthesis, characterization, and termal studies of polyamides and polyimides containing two silarylene units in the main chain. J Appl Polym Sci 110:2424–2431. doi:10.1002/app.28830
Davidsohn W, Laliberte BR, Goddard CM, Henry, M (1972) Organometallic bis(p-hydroxyphenyl) derivatives of group IV elements and related compounds. J Organomet Chem 36:283–291. doi:10.1016/S0022-328X(00)80676-2
Pratt JR, Massey WD, Pinkerton FH, Thames F (1975) Organo silicon compounds. XX. Synthesis of aromatic diamines via trimethylsilyl-protecting aniline intermediates. J Org Chem 40:1090–1094. doi:10.1021/jo00896a021
Faghihi K, Gholizadeh M (2009) Rapid synthesis of new poly(amide-imide)s based on N-(4-carboxy phenyl) trimetillimide and hydantoin derivatives under microwave irradiation. Turk J Chem 33:87–97. doi:10.3906/kim-0807-27
Yamazaki N, Matsumoto M, Higashi F (1975) Studies on reactions of the N-phosphonium salts of pyridines. XIV. Wholly aromatic polyamides by the direct polycondensation reaction by using phosphites in the presence of metal salts. J Polym Sci Polym Chem Ed 13:1373–1380. doi:10.1002/pol.1975.170130609
Tundidor-Camba A, Terraza CA, Tagle LH, Coll D (2011) Polyamides obtained by direct polycondensation of 4-[4-[9-[4-(4-aminophenoxy)-3-methyl-phenyl]fuoren-9-YL]-2-methyl-phenoxy]aniline with dicarboxylic acids based on a diphenyl-silane moiety. J Appl Polym Sci 120:2381–2389. doi:10.1002/app.33443
Mallakpour S, Kowsari E (2006) Synthesis of novel optically active poly(ester-imide)s by direct polycondensation reaction promoted by tosyl chloride in pyridine in the presence of N,N-dimethylformamide. J Appl Poly Sci 101:455–460. doi:10.1002/app.23289
Terraza CA, Tagle LH, Concha F, Poblete L (2007) Synthesis and characterization of new bifunctional monomers based on germarylene or silarylene units: 4,4′-(R1R2-silylene)bis(phenyl chloroformates) and 4,4′-(R1R2-germylene)bis(phenyl chloroformates). Des Mon Polym 10:253–261. doi:10.1163/156855507780949209
Acknowledgment
The authors acknowledge Fondo Nacional de Investigación Científica y Tecnológica, FONDECYT, through Project 1100015, for financial assistance.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Tagle, L.H., Terraza, C.A., Villagra, H. et al. Poly(imide-amide)s and poly(imide-esters)s based on silarylene units containing (l)-alanine moiety: synthesis and characterization. Polym. Bull. 67, 1799–1807 (2011). https://doi.org/10.1007/s00289-011-0507-y
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-011-0507-y