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Synthesis and characterization of new poly(amide)s derived from bis(4-(4-aminophenoxy)phenyl)methylphenylsilane and bis(4-carboxyphenyl)R1R2 silane acids

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Abstract

This study describes the synthesis and characterization of a new diamine; bis(4-(4-aminophenoxy)phenyl)methylphenylsilane, which by reaction with bis(4-carboxyphenyl)R1R2 silane derivatives, and following the methodology of the direct polycondensation, allowed the preparation of three new poly(amide)s (PAs). These polymers contain two diphenylsilane (Ph–Si–Ph) and oxyether moieties in their repetitive unit. The reaction to obtain the diamine starting from the respective diphenol was developed in two steps. The first step consisted on obtaining the dinitro derivative, bis(4-(4-nitrophenoxy)phenyl)methylphenylsilane, with a yield of 83 %. Then, this compound was reduced by reaction with hydrazine and Pd-activated carbon, with a yield of 67 % in the diamine. Both compounds were characterized by spectroscopic techniques (FT-IR, 1H, 13C and 29Si NMR). The synthesis of the PAs (PA-I, PA-II and PA-III) presented a yield of 35–79 %, glass transition temperature between 136 and 149 °C and inherent viscosities in the range 0.08–0.16 g/dL. PA-I and PA-III presented a transmittance value (at 400 nm) of 91 and 87 %, respectively, while PA-II only reached a value of 70 %. All these results were analysed in accordance with structural details of each repetitive unit and were also compared with those obtained from poly(amides) series not containing flexible elements in their chains. The TGA analyses demonstrated that the new polymers still maintain a high thermal resistance, despite the incorporation of the flexible units.

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References

  1. Lin J, Sherrington DC (1994) Recent developments in the synthesis, thermostability and liquid crystal properties of aromatic polyamides. Adv Polym Sci 111:177

    Article  CAS  Google Scholar 

  2. Yang HH (1989) Aromatic high-strength fibers. Wiley, New York

    Google Scholar 

  3. Mittal KL (1984) Polyimides: synthesis, characterization and applications, vols 1 and 2. Springer, New York

    Google Scholar 

  4. Yang CP, Chen YP, Woo EM (2006) Novel organosoluble poly(amide-imide-imide)s synthesized from new tetraimide-dicarboxylic acid by condensation with 4,4′-oxydiphthalic anhydride, 1,4-bis(4-amino-2-trifluoromethylphenoxy)benzene, trimellitic anhydride, and various aromatic diamines. J Appl Polym Sci 101:2854

    Article  CAS  Google Scholar 

  5. Burkhard CA, Rochow EG, Booth SH, Hartt J (1947) The present state of organosilicon chemistry. Chem Rev 41:97

    Article  CAS  Google Scholar 

  6. Hsiao SH, Yang CP, Chu K-Y (1997) Synthesis and properties of aromatic polyamides based on 4,4′-(2,7-naphthalenedioxy)dibenzoic acid. J Polym Sci Part A 35:1469

    Article  CAS  Google Scholar 

  7. Hsiao SH, Chang YM (2004) Synthesis and properties of novel soluble polyamides having ether linkages and laterally attached p-terphenyl units. J Polym Sci Part A 42:4056

    Article  CAS  Google Scholar 

  8. Terraza CA, Liu JG, Nakamura Y, Shibasaki Y, Ando S, Ueda M (2008) Synthesis and properties of highly refractive polyimides derived from fluorene-bridged sulfur-containing dianhydrides and diamines. J Polym Sci Part A 46:1510

    Article  CAS  Google Scholar 

  9. 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]fluoren-9-yl]-2-methyl-phenoxy]aniline with dicarboxylic acids based on a diphenyl-silane moiety. J Appl Polym Sci 120:2381

    Article  CAS  Google Scholar 

  10. Yang CP, Lin JH (1994) Syntheses and properties of aromatic polyamides and polyimides based on N-phenyl-3,3-bis[4-(p-aminophenoxy)phenyl] phthalimidine. J Polym Sci Part A 32:369

    Article  CAS  Google Scholar 

  11. Yang CP, Lin JH (1994) Preparation and properties of aromatic polyamides and polyimides derived from 3,3-bis [4-(4-aminophenoxy)phenyl] phthalide. J Polym Sci Part A 32:423

    Article  CAS  Google Scholar 

  12. Yang CP, Lin JH (1995) Synthesis and polymerization of a bulky styrenic monomer as an in-chain ‘knot’ for polyrotaxanes. Polymer 36:2607

    Article  CAS  Google Scholar 

  13. Tundidor-Camba A, Terraza CA, Tagle LH, Coll D (2012) Synthesis of poly(urethane)s based on diphenyl-silane/germane and oxyphenyl units. Structure–properties relationship. J Appl Polym Sci 124(2):1036

    Article  CAS  Google Scholar 

  14. Bruma M, Schulz B (2001) Silicon-containing aromatic polymers. Macromol Sci Polym Rev 41:1

    Article  Google Scholar 

  15. Pratt JR, Massey WD, Pinkerton FH, Thames SF (1975) Organosilicon compounds. XX. Synthesis of aromatic diamines via trimethylsilyl-protecting aniline intermediates. J Org Chem 40:1090

    Article  CAS  Google Scholar 

  16. Tagle LH, Terraza CA, Leiva A, Devilat F (2008) Synthesis, characterization and thermal studies of poly(amides) and poly(imides) that contain two silarylene units in the main chain. J Appl Polym Sci 110:2424

    Article  CAS  Google Scholar 

  17. Tagle LH, Terraza CA, 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

    CAS  Google Scholar 

  18. Terraza CA, Tagle LH, Leiva A, Poblete L, Concha FJ (2008) Poly(urethanes) containing silarylene and/or germarylene units. J Appl Polym Sci 109:303

    Article  CAS  Google Scholar 

  19. Tagle LH, Diaz FR, Vega JC, Valenzuela P (2003) Synthesis and characterization of poly(esters) derived from diacids and diphenols containing silicon and germanium. Eur Polym J 39:407

    Article  CAS  Google Scholar 

  20. González-Henríquez CM, Tagle LH, Terraza CA, Barriga A, Cabrera AL, Volkmann UG (2012) Poly(ester)s and poly(amide)s with fluorene and diphenyl-silane units in the main chain. Effect of iodine doping on the structure and electrical conductivity. J Appl Polym Sci 125:477

    Article  Google Scholar 

  21. González-Henríquez CM, Terraza CA, Tagle LH, Barriga A, Volkmann UG, Cabrera AL, Ramos-Moore E, Retamal MJ (2012) Inclusion effect of gold and copper particles in a poly(amide) matrix that contains a thiophene moiety and Si or Ge atoms in the main chain. J Mater Chem 22:6782

    Article  Google Scholar 

  22. Terraza CA, Tagle LH, Tundidor-Camba A, González-Henríquez CM, Ortiz P, Coll D (2012) Poly(amide)s obtained from 4-(4-((4-(4-aminophenoxy)phenyl)diphenyl silyl)phenoxy)benzenamine and dicarboxylic acids containing diphenylsilarylene units. Synthesis and characterization. Eur Polym J 48:649

    Article  CAS  Google Scholar 

  23. Tagle LH, Terraza CA, Ahlers W, Vera C (2005) Synthesis of condensation polymers derived from silylated monomers under phase transfer catalysis. J Chil Chem Soc 50(3):535

    Article  CAS  Google Scholar 

  24. Gunthener AJ, Yandek GR, Writh ME, Petteys BJ, Quintana R, Connor D, Gilardi RD, Marchant D (2006) A new silicon-containing bis(cyanate) ester resin with improved thermal oxidation and moisture resistance. Macromolecules 39:6046

    Article  Google Scholar 

  25. Davidsohn W, Laliberte BR, Goddard CM, Henry CM (1972) Organometallic bis(p-hydroxyphenyl) derivatives of group IV elements and related compounds. J Organomet Chem 36:283

    Article  CAS  Google Scholar 

  26. 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 13:1373

    CAS  Google Scholar 

  27. Terraza CA, Tagle LH, Concha F, Poblete L (2007) Synthesis and characterization of new bifunctional monomers based on germarylene and silarylene units. 4,4′-(R1,R2-silylene)bis(phenyl chloroformates) and 4,4′-(R1,R2-germarylene) bis(phenyl chloroformates). Des Mon Polym 10:253

    Article  CAS  Google Scholar 

  28. The Periodic Table. University of Sheffield, Webelements Ltd. OK. Available at http://www.webelements.com. Accessed April 2012

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Acknowledgments

The authors acknowledge the financial assistance by Fondo Nacional de Investigación Científica y Tecnológica, FONDECYT, through Project 1095151. A. Tundidor-Camba thanks CONICYT for a fellowship.

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Authors and Affiliations

  1. Departamento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, P.O. Box 306, Correo 22, 6094411, Santiago, Chile

    C. A. Terraza, L. H. Tagle, D. Mejías, A. Tundidor-Camba, P. Ortiz, D. Muñoz, F. Alvarez & C. M. González-Henríquez

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  1. C. A. Terraza
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  2. L. H. Tagle
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  3. D. Mejías
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  4. A. Tundidor-Camba
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  5. P. Ortiz
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  6. D. Muñoz
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  7. F. Alvarez
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  8. C. M. González-Henríquez
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Correspondence to C. A. Terraza.

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Terraza, C.A., Tagle, L.H., Mejías, D. et al. Synthesis and characterization of new poly(amide)s derived from bis(4-(4-aminophenoxy)phenyl)methylphenylsilane and bis(4-carboxyphenyl)R1R2 silane acids. Polym. Bull. 70, 773–788 (2013). https://doi.org/10.1007/s00289-012-0824-9

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  • DOI: https://doi.org/10.1007/s00289-012-0824-9

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