Using Microwave Irradiation to Prepare New Poly(amide-imide)s Containing Tetrahydropyrimidinone, Tetrahydro-2-thioxopyrimidine, and Trimellitic Rings in Their Main Chains: Synthesis and Characterization

Khalil Faghihi; Mohsen Hagibeygi

Macromolecular Research, Vol.13, No.1, 14-18, February, 2005

Khalil Faghihi^{1, 2, †}, and Mohsen Hagibeygi³

¹Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Arak University, 38156, Arak, Iran
² Dept. of Chemical Eng., Faculty of Eng., Azad University of Arak, Arak, Iran
³Dept. of Chemical Eng., Faculty of Eng., Azad University of Arak, Arak, Iran

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Under irradiation in a microwave oven, six novel poly(amide-imide)s containing tetrahydropyrimidinone, tetrahydro-2-thioxopyrimidine moieties and trimellitic rings in their main chains were synthesized through the polycondensation reaction of N,N'-(4,4'-diphenylether)bis(trimellitimide) diacid chloride with six different derivatives of tetrahydropyrimidinone and tetrahydro-2-thioxopyrimidine in the presence of a small amount of a polar organic medium, such as o-cresol. The polycondensation proceeded rapidly and completed within 7-9 min, producing a series of new poly(amide-imide)s in high yield that showed inherent viscosities in the range 0.33-0.52 dL/g. These poly(amide-imide)s were characterized by elemental analysis, viscosity measurement, thermal gravimetric analysis, solubility test, and FT-IR spectroscopy. All of the polymers were soluble at room temperature in polar solvents such as N,N-dimethylacetamide, N,N-dimethylformamide, dimethylsulfoxide, tetrahydrofuran, and N-methyl-2-pyrrolidone.

Keywords:poly(amide-imide)s;polycondensation;microwave irradiation;characterization;thermally-stable polymers

[References]

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Baudel V, Cazier F, Woisel P, Surpateanu G, Eur. Polym. J., 38, 615 (2002)
Varma SR, Green Chem., 1, 43 (1999)
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Caddick S, Tetrahedron, 38, 10403 (1995)
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Mijovic J, Fishbain A, Wijaya J, Macromolecules, 25, 986 (1992)
Hottong U, Wei J, Dhulipala R, Hawley MC, Ceram. Trans., 21, 587 (1991)
Jullien H, Valot H, Polymer, 26, 505 (1985)
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Peng Y, Song G, Green Chem., 3, 302 (2001)
Mallakpour SE, Hajipour AR, Faghihi K, Polym. Int., 49, 1383 (2000)
Mallakpour SE, Hajipour AR, Faghihi K, Eur. Polym. J., 37, 119 (2001)
Mallakpour SE, Hajipour AR, Faghihi K, Foroughifar N, Bagheri J, J. Appl. Polym. Sci., 80(13), 2416 (2001)
Faghihi K, Zamani K, Mirsamie A, Sangi MR, Eur. Polym. J., 39, 247 (2003)
Faghihi K, Zamani K, Mirsamie A, Mallakpour S, Polym. Int., 53, 1226 (2004)
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Abadie MJM, Sillion B, Polyimide and Other High Temperature Polymers, Elesevier, New York (1991)
Ghosh MK, Mittal KL, Polyimide: Fundamentals and Applications, Elesevier, New York (1996)
Zhang W, Jin JI, Lenz RW, Makromol. Chem., 189, 2219 (1988)
Krigbaum WR, Hakemi H, Kotek R, Macromolecules, 18, 965 (1985)
Jedlinski Z, Franek J, Uryu K, Song JC, Kato T, Polym. J., 21, 409 (1989)
Chen JP, Natansohn A, Macromolecules, 32(10), 3171 (1999)
Yeganeh H, Barikani M, Khodabadi FN, Eur. Polym. J., 36, 2207 (2000)
Esfandiary D, Synthesis of New Different Derivatives of Tetrahydropyrimidinone and Tetrahydro-2-thioxopyrimidine Compounds, M. S. Thesis, University of Arek, Iran (1999)
Kappe CO, Accounts Chem. Res., 33, 879 (2000)

[Referenced By]

[1] Lidstrom P, Tierney J, Wathey B, Westman J, Tetrahedron, 57, 9225 (2001)

[2] Baudel V, Cazier F, Woisel P, Surpateanu G, Eur. Polym. J., 38, 615 (2002)

[3] Varma SR, Green Chem., 1, 43 (1999)

[4] Watanabe S, Hayama K, Park KH, Kakimoto M, Imai Y, Macromol. Rapid Commun., 14, 481 (1993)

[5] Caddick S, Tetrahedron, 38, 10403 (1995)

[6] Wei J, DeLong JD, DeMeuse M, Hawley MC, Polym. Eng. Sci., 33, 1132 (1993)

[7] Mijovic J, Fishbain A, Wijaya J, Macromolecules, 25, 986 (1992)

[8] Hottong U, Wei J, Dhulipala R, Hawley MC, Ceram. Trans., 21, 587 (1991)

[9] Jullien H, Valot H, Polymer, 26, 505 (1985)

[10] Ward TC, Chen M, Polym. Mater. Sci. Eng., 66, 335 (1992)

[11] Lewis DA, Mater. Res. Soc. Symp. Proc., 269, 21 (1992)

[12] Peng Y, Song G, Green Chem., 3, 302 (2001)

[13] Mallakpour SE, Hajipour AR, Faghihi K, Polym. Int., 49, 1383 (2000)

[14] Mallakpour SE, Hajipour AR, Faghihi K, Eur. Polym. J., 37, 119 (2001)

[15] Mallakpour SE, Hajipour AR, Faghihi K, Foroughifar N, Bagheri J, J. Appl. Polym. Sci., 80(13), 2416 (2001)

[16] Faghihi K, Zamani K, Mirsamie A, Sangi MR, Eur. Polym. J., 39, 247 (2003)

[17] Faghihi K, Zamani K, Mirsamie A, Mallakpour S, Polym. Int., 53, 1226 (2004)

[18] Faghihi K, Zamani K, Mirsamie A, Mallakpour S, J. Appl. Polym. Sci., 91(1), 516 (2004)

[19] Abadie MJM, Sillion B, Polyimide and Other High Temperature Polymers, Elesevier, New York (1991)

[20] Ghosh MK, Mittal KL, Polyimide: Fundamentals and Applications, Elesevier, New York (1996)

[21] Zhang W, Jin JI, Lenz RW, Makromol. Chem., 189, 2219 (1988)

[22] Krigbaum WR, Hakemi H, Kotek R, Macromolecules, 18, 965 (1985)

[23] Jedlinski Z, Franek J, Uryu K, Song JC, Kato T, Polym. J., 21, 409 (1989)

[24] Chen JP, Natansohn A, Macromolecules, 32(10), 3171 (1999)

[25] Yeganeh H, Barikani M, Khodabadi FN, Eur. Polym. J., 36, 2207 (2000)

[26] Esfandiary D, Synthesis of New Different Derivatives of Tetrahydropyrimidinone and Tetrahydro-2-thioxopyrimidine Compounds, M. S. Thesis, University of Arek, Iran (1999)

[27] Kappe CO, Accounts Chem. Res., 33, 879 (2000)