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Journals / Turkish Journal of Chemistry / 2008 / Cilt: 32 - Sayı: 1

New Polyamides Based on Bis(p-amidobenzoic acid)-p-phenylene diacrylic acid and Hydantoin Derivatives: Synthesis and Characterization

Khalil FAGHIHI
Pages
75–86
Publication Date
2008-01-01
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The resulting polyamides were characterized by elemental analysis, viscosity measurements, thermal gravimetric analysis (TGA and DTG), solubility test, FT-IR, and UV-vis spectroscopy.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Bis(p-amidobenzoic acid)-p-phenylene diacrylic acid (6) as a new monomer containing p-phenylenediacryloyl moiety was synthesized by using a 3-step reaction.
📊
Key Findings & Data:At first p-phenylenediacrylic acid (3) was prepared by reaction of terephthal aldehyde (1) with malonic acid (2) in the presence of pyridine, and then diacid 3 was converted to p-phenylenediacryloyl chloride (4) by reaction with thionyl chloride.
💡
Conclusion & Impact:The resulting polyamides were characterized by elemental analysis, viscosity measurements, thermal gravimetric analysis (TGA and DTG), solubility test, FT-IR, and UV-vis spectroscopy.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Polyamides · p-phenylenediacryloyl moieties · bis(p-amidobenzoic acid)-p-phenylene diacrylic acid

Abstract

Bis(p-amidobenzoic acid)-p-phenylene diacrylic acid (6) as a new monomer containing p-phenylenediacryloyl moiety was synthesized by using a 3-step reaction. At first p-phenylenediacrylic acid (3) was prepared by reaction of terephthal aldehyde (1) with malonic acid (2) in the presence of pyridine, and then diacid 3 was converted to p-phenylenediacryloyl chloride (4) by reaction with thionyl chloride. Finally bis(p-amidobenzoic acid)-p-phenylene diacrylic acid (6) was prepared by the condensation reaction of phenylenediacryloyl chloride (4) with p-aminobenzoic acid (5). Then 6 new polyamides (8a-f) containing p-phenylenediacryloyl and hydantoin moiety in the main chain were prepared by the direct polycondensation reaction of bis(p-amidobenzoic acid)-p-phenylene diacrylic acid (6) with 6 different hydantoin derivatives (7a-f) by thionyl chloride, N-methyl-2-pyrolidone and pyridine as condensing agents. These new polymers (8a-f) were obtained in high yield and inherent viscosity between 0.32-0.50 dL/g. The resulting polyamides were characterized by elemental analysis, viscosity measurements, thermal gravimetric analysis (TGA and DTG), solubility test, FT-IR, and UV-vis spectroscopy.

Özet

Bis(p-amidobenzoic acid)-p-phenylene diacrylic acid (6) as a new monomer containing p-phenylenediacryloyl moiety was synthesized by using a 3-step reaction. At first p-phenylenediacrylic acid (3) was prepared by reaction of terephthal aldehyde (1) with malonic acid (2) in the presence of pyridine, and then diacid 3 was converted to p-phenylenediacryloyl chloride (4) by reaction with thionyl chloride. Finally bis(p-amidobenzoic acid)-p-phenylene diacrylic acid (6) was prepared by the condensation reaction of phenylenediacryloyl chloride (4) with p-aminobenzoic acid (5). Then 6 new polyamides (8a-f) containing p-phenylenediacryloyl and hydantoin moiety in the main chain were prepared by the direct polycondensation reaction of bis(p-amidobenzoic acid)-p-phenylene diacrylic acid (6) with 6 different hydantoin derivatives (7a-f) by thionyl chloride, N-methyl-2-pyrolidone and pyridine as condensing agents. These new polymers (8a-f) were obtained in high yield and inherent viscosity between 0.32-0.50 dL/g. The resulting polyamides were characterized by elemental analysis, viscosity measurements, thermal gravimetric analysis (TGA and DTG), solubility test, FT-IR, and UV-vis spectroscopy.

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Cite This Article

FAGHIHI, K. (2008). New Polyamides Based on Bis(p-amidobenzoic acid)-p-phenylene diacrylic acid and Hydantoin Derivatives: Synthesis and Characterization. Turkish Journal of Chemistry, Cilt: 32 - Sayı: 1, 75–86. https://ajindex.com/articles/217978

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References (27)

  1. P. E. Cassidy, Thermally Stable Polymers, Dekker, New York (1980).
  2. H. H. Yang, Aromatic High-Strength Fibers, Wiley, New York (1989).
  3. S. H. Hsiao, C. P. Yang and K. Y. Chu, J. Polym. Sci. Part A: Polym. Chem. 35, 1469 (1997)
  4. S. H. Hsiao and K. Y. Chu, J. Polym. Sci. Part A: Polym. Chem. 35, 3385 (1997).
  5. P. W. Morgan, Chemtech. 9, 316 (1979).
  6. K. P. Park, M. A. Kakimoto and Y. Imai, J. Pol ym. Sci. Part A: Pol ym. Chem. 33, 1031 (1995).
  7. C. P. Yang, S. H. Hsiao and C. C. Yang, J. Polym. Sci. Part A: Polym. Chem. 35, 2147 (1997).
  8. J. A. Mikroyannidis, J. Polym. Sci. Part A: Polym. Chem. 35, 1353 (1997).
  9. S. H. Hsiao and K. Y. Chu, J. Polym. Sci. Part A: Polym. Chem. 35, 3385 (1997).
  10. Y. L. Liu and S. H. Tsai, Polym. 43, 5757 (2002).
  11. Z. Ge, S. Yang, Z. Tao, J. Liu and I. Fan, Polym. 45, 3627 (2004).
  12. S. A. Mehdipour, Y. SarraŞ, M. Hatami and L. F. Akbarian, Eur. Polym. J. 41, 491 (2005).
  13. N. Avella, G. Maglio, R.; Palumbo, F. Russo and M. C. Vignola, Makromol. Chem. Rapid Commun. 14, (1993).
  14. H. J. Jeong, Y. Oishi, M. Kakimoto and Y.Imai, J. Polym. Sci. Part A: Polym. Chem. 28, 3293 (1990).
  15. H. J. Jeong, M. A. Kakimoto and Y. Imai, J. Pol ym. Sci. Pol ym. Chem. 29, 767 (1991).
  16. A. L. Cimecioglu and R. A. Weiss, J. Polym. Sci. Polym. Chem. 30, 1051 (1992).
  17. Y. Delaviz, A. Gungor, J. E. McGrath and H. W. Gibson, Pol ym. 34, 210 (1993).
  18. M. Takayanagi and T. Katayose, J. Polym. Sci. Polym. Chem. Ed. 19, 1133 (1981).
  19. H. G. Rogers, R. A. Gaudiana, W. C. Hollinsed, P. S. Kalyanaraman, J. S. Manello, C. McGowan, R. A. Minns and R. Sahatjian, Macromol. 18, 1058 (1985).
  20. N. Yamazaki, F. Higashi and J. Kawabata, J. Polym. Sci. Polym. Chem. Ed. 12, 2149 (1974).
  21. N. Yamazaki, M. Matsumoto and F. Higashi, J. Polym. Sci. Polym. Chem. Ed. 13, 1373 (1975).
  22. P. L. Egertone, J. Trigg, E. M. Hyde and A. Reiser, Macromol. 14, 100 (1984).
  23. L. Chienhui, C. Tehchou and H. Kehying, J. Polym. Sci. Polym. Chem. Ed. 31, 1119 (1993).
  24. H. Kehying, L. Chienhui, C. Tehchou and C. Tsuyao, J. Pol ym. Sci. Pol ym. Chem. Ed. 31, 971 (1993).
  25. H. Tanaka, K. Sasai, T. Sato and O. Tadatoshi, Macromol. 21, 3536 (1988).
  26. Kh. Faghihi and M. Hajibeygi, Eur. Polym. J. 2003. 39, 2307 (2003).
  27. M. Lamothe, M. Lannuzel and M. Perez, J. Comb. Chem. 4, 73 (2002). Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley and Sons, New York, 3rdEd, 12, 692 (1983).