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Syntheses and properties of fluorinated polyamides and poly(amide imide)s based on 9,9-bis[4-(4-amino-2-trifluromethylphenoxy)phenyl]fluroene, aromatic dicarboxylic acids, and various monotrimellitimides and bistrimellitimides

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Abstract

A diamine, 9,9-bis[4-(4-amino-2-trifluromethylphenoxy)phenyl]fluroene (I) containing the CF3 group, was prepared from 9,9-bis(4-hydroxyphenyl)fluorene and 2-chloro-5-nitrobenzotrifluoride. The imide-containing diacids (V a-j and VI a,b) were prepared by condensation reaction of amino acids, aromatic diamines, and trimellitic anhydride. Then, a series of soluble fluorinated polyamides (VII a-e) and poly(amide imide)s (VIII a-j and X a,b) were synthesized from diamine (I) with various aromatic diacids II a-h and the imide-containing diacids (V a-j and VI a,b) via direct polycondensation with triphenyl phosphate and pyridine. All polymers showed excellent solubility in amide-type solvents such as N-dimethylforamide and can also be dissolved in pyridine, m-cresol, and tetrahydrofuran. Polymers afford transparent and tough films by solvent casting. The glass transition temperature of these polymers were in the range of 278–366°C, and the poly(amide imide)s had better thermal stability than polyamides. In comparison with the isomeric IX a-d, VIII a-d showed a lighter color with lower b* (yellowness index) values than the corresponding IX series.

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References

  1. Cassidy PE (1980) Thermally stable polymers. Marcel Dekker, New York

    Google Scholar 

  2. Seymour RB, Carraher CE (1981) Polym chem: an introduction. Marcel Dekker, New York

    Google Scholar 

  3. Kricheldrof HR, Schmidt B (1992) Macromolecules 25:5471

    Article  Google Scholar 

  4. Kricheldrof HR, Burger R (1994) J Polym Sci [A1] 32:355

    Article  Google Scholar 

  5. Fled WA, Ramalingam B, Harria FW (1983) J Polym Sci [A1] 21:319

    Google Scholar 

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

    Google Scholar 

  7. Imai Y, Malder NN, Kakimoto M (1989) J Polym Sci [A1] 22:2189

    Google Scholar 

  8. Bruma M, Mercer F, Fitch J, Cassidy P (1995) J Appl Polym Sci 56:527

    Article  CAS  Google Scholar 

  9. Jeong HJ, Oishi Y, Kakimoto M, Imai Y (1991) J Polym Sci [A1] 2:39

    Article  Google Scholar 

  10. Oishi Y, Ishida M, Kakimoto M, Imai Y, Kurosaki T (1992) J Polym Sci [A1] 30:1027

    Article  CAS  Google Scholar 

  11. Liou GS, Kakimoto M, Imai Y (1993) J Polym Sci [A1] 31:3265

    Article  CAS  Google Scholar 

  12. Song CE (1979) J Polym Sci D 11:161

    Google Scholar 

  13. Imai Y, Kakimoto NN, Kakimoto M (1995) J Polym Sci [A1] 33:2209

    Article  Google Scholar 

  14. Ghosh MK, Mittal KL (eds) (1996) Polyimides: fundamentals and applications. Marcel Dekker, New York

    Google Scholar 

  15. R Buch P, R Reddy AV (2005) Polymer 46:5524

    Article  CAS  Google Scholar 

  16. Hitachi Chemical Co (1967) French Patent 1,473,600

  17. Kakimoto M, Akiyama R, Negi YS, Imai Y (1988) J Polym Sci [A1] 26:99

    Article  CAS  Google Scholar 

  18. Imai Y, Malder NN, Kakimoto M (1985) J Polym Sci [A1] 23:2077

    CAS  Google Scholar 

  19. Dezern JF (1988) J Polym Sci [A1] 26:2157

    Article  CAS  Google Scholar 

  20. Bower GM, Frost LW. (1988) J Polym Sci Part A: Polym Chem 26:2157

    Article  Google Scholar 

  21. Yang CP, Chen RS, Chen KH, Chen YP (2002) J Chin Chem Soc 49:927

    CAS  Google Scholar 

  22. Yang CP, Hsiao SH, Lin JH (1992) Macromol Chem 193:1299

    Article  CAS  Google Scholar 

  23. Yang CP, Chen WT, Lin JH (1994) J Polym Sci Part A: Polym Chem 32:435

    Article  CAS  Google Scholar 

  24. Xie K, Shang SY, Liu JG., He MH, Yang SY (2001) J Polym Sci Part A: Polym Chem 39:2581

    Article  CAS  Google Scholar 

  25. Yang CP, Lin, J H (1995) Polym Int 38:335

    Article  CAS  Google Scholar 

  26. Yang CP, Chiang HC (2004) Colloid Polym Sci 282:1347

    Article  CAS  Google Scholar 

Download references

Acknowledgement

The authors are grateful to the National Science Council of the Republic of China for the support of this work (Grant NSC 93-2216-E-036-003).

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Authors and Affiliations

  1. Department of Chemical Engineering, Tatung University, 40 Chungshan North Road, 3rd Section, Taipei, Taiwan, 104, People’s Republic of China

    Chin-Ping Yang, Yu-Yang Su & Mei-Yuan Hsu

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  1. Chin-Ping Yang
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  2. Yu-Yang Su
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  3. Mei-Yuan Hsu
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Correspondence to Chin-Ping Yang.

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Yang, CP., Su, YY. & Hsu, MY. Syntheses and properties of fluorinated polyamides and poly(amide imide)s based on 9,9-bis[4-(4-amino-2-trifluromethylphenoxy)phenyl]fluroene, aromatic dicarboxylic acids, and various monotrimellitimides and bistrimellitimides. Colloid Polym Sci 284, 990–1000 (2006). https://doi.org/10.1007/s00396-005-1440-0

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