New Highly Thermostable Aromatic Polyamides with Pendant Phthalonitrile Groups

Ionela-Daniela Carja; Corneliu Hamciuc; Elena Hamciuc; Tachita Vlad-Bubulac; Gabriela Lisa

Macromolecular Research, Vol.20, No.10, 1011-1020, October, 2012

DOI10.1007/s13233-012-0147-6 Export Citation

New Highly Thermostable Aromatic Polyamides with Pendant Phthalonitrile Groups

Ionela-Daniela Carja, Corneliu Hamciuc^†, Elena Hamciuc, Tachita Vlad-Bubulac, and Gabriela Lisa¹

“Petru Poni” Institute of Macromolecular Chemistry, Aleea Gr. Ghica Voda 41A, Iasi, 700487, Romania
¹Faculty of Chemical Engineering and Environmental Protection, “Gh. Asachi” Technical University, B-dul D. Mangeron 71, Iasi, 700050, Romania

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A phthalonitrile-containing diamine monomer, 4,4'-diamino-4''-(3,4-dicyanophenoxy)-triphenylmethane, 1, was prepared, and its cure behavior was investigated. The diamine 1 was thermally polymerized at 250 ℃ even in absence of curing additives. The resulting resins exhibited exceptional high thermal and thermo-oxidative stability, with the 5% weight loss being above 500 ℃ and the char yield at 700 ℃ being over 62%, in air or inert atmosphere. New soluble aromatic polyamides derived from diamine 1, 2,2-bis[4-(4-aminophenoxy)phenyl]propane and terephthaloyl chloride were synthesized. They showed good solubility in organic solvents, film forming properties, and high thermal stability, with the decomposition temperature being above 400 ℃. The kinetic processing of thermogravimetric data was carried out using differential and integral methods. Electrical properties of the polymer films were evaluated on the basis of dielectric constant and dielectric loss and their variation with frequency and temperature. The influence of the phthalonitrile content on the polymer properties was studied.

Keywords:aromatic polyamides;phthalonitrile groups;thin films;thermal properties;dielectric constant.

[References]

Keller TM,, J. Polym. Sci. Part C: Polym. Lett., 24, 211 (1986)
Keller TM, Roland CM, US Patent 5242755 (1993)
Sastri SB, Armistead JP, Keller TM, Polym. Compos., 17, 816 (1996)
Sastri SB, Armistead JP, Keller TM, Sorathia U, Polym. Compos., 18, 48 (1997)
Dominguez DD, Jones YN, Keller TM, Polym.Compos., 25, 554 (2004)
Zeng K, Zhou K, Zhou S, Hong H, Zhou H, Wang Y, Miao P, Yang G, Eur. Polym. J., 45, 1328 (2009)
Keller TM, J. Polym. Sci. Part A: Polym. Chem., 26, 3199 (1988)
Keller TM, Polymer., 234, 952 (1993)
Keller TM, Chem. Mater., 6, 302 (1994)
Sastri SB, Keller TM, J. Polym. Sci. A: Polym. Chem., 36(11), 1885 (1998)
Keller TM, Dominguez DD, Polymer, 46(13), 4614 (2005)
Laskoski M, Dominguez DD, Keller TM, J. Polym. Sci. A: Polym. Chem., 43(18), 4136 (2005)
Cao GP, Chen WJ, Wei JJ, Li WT, Liu XB, Exp.Polym. Lett., 1, 512 (2007)
Selvakumar P, Sarojadevi M, Sundararajan P, Mater.Sci. Eng. B., 168, 214 (2010)
Selvakumar P, Padmini K, Sarojadevi M, Leelavanthy MF, J. Macromol. Sci. A., 47, 76 (2010)
Yang XL, Lei YJ, Zhong JC, Zhao R, Liu XB, J. Appl. Polym. Sci., 119(2), 882 (2011)
Zeng K, Hong HB, Zhou SH, Wu DM, Miao PK, Huang ZF, Yang G, Polymer, 50(21), 5002 (2009)
Zeng K Zhou K, Tang WR, Tang Y, Zhou HF, Liu T, Wang YP, Zhou HB, Yang G, Chin. Chem. Lett.
Zhou SH, Hong HB, Zeng K, Miao PK, Zhou HF, Wang YP, Liu T, Zhao CN, Xu GL, Yang G, Polym. Bull., 62(5), 581 (2009)
Selvakumar P, Sarojadevi M, Macromol. Symp., 277, 190 (2009)
Vollbracht L, in Comprehensive Polymer Science, Allen G, Bevington B, Eastmond GV, Ledwith A, Russo S, Sigwald P, Eds., Pergamon Press, Oxford, 5, 373 (1989)
Gallini J, in Encyclopedia of Polymer Science and Technology, John Wiley & Sons, New York, 3, 558 (2005)
Negi YS, Razdan U, Saran V, J. Macromol. Chem.Rev. Macromol. Chem. Phys., C39, 391 (1999)
Garcia JM, Garcia FC, Serna F, de la Pena JL, Prog. Polym. Sci., 35, 623 (2010)
Hamciuc C, Hamciuc E, Ipate AM, Okrasa L, Polymer, 49(3), 681 (2008)
Vlad-Bubulac T, Hamciuc C, Polymer, 50(10), 2220 (2009)
Chen BK, Chiu TM, Tsay SY, J. Appl. Polym. Sci., 94(1), 382 (2004)
Chang YT, Shu CF, Leu CM, Wei KH, J. Polym. Sci. A: Polym. Chem., 41(23), 3726 (2003)
Socrate G, Infrared and Raman Characteristic Group Frequencies: Tables and Charts, 3rd ed., John Wiley & Sons, New York, 177 (2004)
ASTM Test method E698, Standard Test Method for Arrhenius Kinetic Constants for Thermally Unstable Materials, ASTM International, West Conshohocken, 56 (1984)
Vyazovkin S, Wight CA, Thermochim. Acta, 340-341, 53 (1999)
METTLER TOLEDO STARe, System Manual for Kinetic Analysis by TGA/DSC.
ASTM Test method E1641, Standard Test Method for Decomposition Kinetics by Thermogravimetry, ASTM Book of Standards, American Society for Testing and Materials, West Conshohocken, Vol. 14.02, 1042 (1994)
Diazcalleja R, Deabajo J, Delacampa JG, J. Polym. Sci. B: Polym. Phys., 35(6), 919 (1997)
Lee HT, Chuang KR, Chen SA, Wei PK, Hsu JH, Fann WS, Macromolecules, 28(23), 7645 (1995)

[1] Keller TM,, J. Polym. Sci. Part C: Polym. Lett., 24, 211 (1986)

[2] Keller TM, Roland CM, US Patent 5242755 (1993)

[3] Sastri SB, Armistead JP, Keller TM, Polym. Compos., 17, 816 (1996)

[4] Sastri SB, Armistead JP, Keller TM, Sorathia U, Polym. Compos., 18, 48 (1997)

[5] Dominguez DD, Jones YN, Keller TM, Polym.Compos., 25, 554 (2004)

[6] Zeng K, Zhou K, Zhou S, Hong H, Zhou H, Wang Y, Miao P, Yang G, Eur. Polym. J., 45, 1328 (2009)

[7] Keller TM, J. Polym. Sci. Part A: Polym. Chem., 26, 3199 (1988)

[8] Keller TM, Polymer., 234, 952 (1993)

[9] Keller TM, Chem. Mater., 6, 302 (1994)

[10] Sastri SB, Keller TM, J. Polym. Sci. A: Polym. Chem., 36(11), 1885 (1998)

[11] Keller TM, Dominguez DD, Polymer, 46(13), 4614 (2005)

[12] Laskoski M, Dominguez DD, Keller TM, J. Polym. Sci. A: Polym. Chem., 43(18), 4136 (2005)

[13] Cao GP, Chen WJ, Wei JJ, Li WT, Liu XB, Exp.Polym. Lett., 1, 512 (2007)

[14] Selvakumar P, Sarojadevi M, Sundararajan P, Mater.Sci. Eng. B., 168, 214 (2010)

[15] Selvakumar P, Padmini K, Sarojadevi M, Leelavanthy MF, J. Macromol. Sci. A., 47, 76 (2010)

[16] Yang XL, Lei YJ, Zhong JC, Zhao R, Liu XB, J. Appl. Polym. Sci., 119(2), 882 (2011)

[17] Zeng K, Hong HB, Zhou SH, Wu DM, Miao PK, Huang ZF, Yang G, Polymer, 50(21), 5002 (2009)

[18] Zeng K Zhou K, Tang WR, Tang Y, Zhou HF, Liu T, Wang YP, Zhou HB, Yang G, Chin. Chem. Lett.

[19] Zhou SH, Hong HB, Zeng K, Miao PK, Zhou HF, Wang YP, Liu T, Zhao CN, Xu GL, Yang G, Polym. Bull., 62(5), 581 (2009)

[20] Selvakumar P, Sarojadevi M, Macromol. Symp., 277, 190 (2009)

[21] Vollbracht L, in Comprehensive Polymer Science, Allen G, Bevington B, Eastmond GV, Ledwith A, Russo S, Sigwald P, Eds., Pergamon Press, Oxford, 5, 373 (1989)

[22] Gallini J, in Encyclopedia of Polymer Science and Technology, John Wiley & Sons, New York, 3, 558 (2005)

[23] Negi YS, Razdan U, Saran V, J. Macromol. Chem.Rev. Macromol. Chem. Phys., C39, 391 (1999)

[24] Garcia JM, Garcia FC, Serna F, de la Pena JL, Prog. Polym. Sci., 35, 623 (2010)

[25] Hamciuc C, Hamciuc E, Ipate AM, Okrasa L, Polymer, 49(3), 681 (2008)

[26] Vlad-Bubulac T, Hamciuc C, Polymer, 50(10), 2220 (2009)

[27] Chen BK, Chiu TM, Tsay SY, J. Appl. Polym. Sci., 94(1), 382 (2004)

[28] Chang YT, Shu CF, Leu CM, Wei KH, J. Polym. Sci. A: Polym. Chem., 41(23), 3726 (2003)

[29] Socrate G, Infrared and Raman Characteristic Group Frequencies: Tables and Charts, 3rd ed., John Wiley & Sons, New York, 177 (2004)

[30] ASTM Test method E698, Standard Test Method for Arrhenius Kinetic Constants for Thermally Unstable Materials, ASTM International, West Conshohocken, 56 (1984)

[31] Vyazovkin S, Wight CA, Thermochim. Acta, 340-341, 53 (1999)

[32] METTLER TOLEDO STARe, System Manual for Kinetic Analysis by TGA/DSC.

[33] ASTM Test method E1641, Standard Test Method for Decomposition Kinetics by Thermogravimetry, ASTM Book of Standards, American Society for Testing and Materials, West Conshohocken, Vol. 14.02, 1042 (1994)

[34] Diazcalleja R, Deabajo J, Delacampa JG, J. Polym. Sci. B: Polym. Phys., 35(6), 919 (1997)

[35] Lee HT, Chuang KR, Chen SA, Wei PK, Hsu JH, Fann WS, Macromolecules, 28(23), 7645 (1995)