Preparation and Characterization of Flexible, Transparent and Thermally Stable Aromatic Co-polyamides
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摘要
Two aromatic co-polyamides were synthesized combining two diacid monomers containing bulky pendant groups, 5-(9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximido)isophthalic acid(DEAIA) and 5-tert-butylisophthalic acid(TERT), with 4,4′-(hexafluoroisopropylidene)dianiline(HFA) or 2,3,5,6-tetramethyl-1,4-phenylenediamine(Durene) by direct polycondensation. The structures of the obtained aromatic co-polyamides were confirmed by FTIR, Raman and 1 H-NMR. The co-copolyamide films, DHTH and DDTD, exhibited rms-roughness values between 0.94 and 1.60 nm, respectively. Moreover, they presented good thermal stability up to300 °C. Young's moduli of the co-polyamide films were between 4.1 and 4.3 GPa. X-ray diffraction results showed that the co-polyamide films were amorphous due to the incorporation of both bulky pendant groups, tert-butyl and dibenzobarrelene. The combination of bulky pendant groups provided intrinsically transparent co-polyamide films with a transmittance higher than 88% in the range of 400-780 nm.Due to these outstanding film and optical properties, they are suggested to be flexible substrates in applications for solar cell and other portable electronic devices.
Two aromatic co-polyamides were synthesized combining two diacid monomers containing bulky pendant groups, 5-(9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximido)isophthalic acid(DEAIA) and 5-tert-butylisophthalic acid(TERT), with 4,4′-(hexafluoroisopropylidene)dianiline(HFA) or 2,3,5,6-tetramethyl-1,4-phenylenediamine(Durene) by direct polycondensation. The structures of the obtained aromatic co-polyamides were confirmed by FTIR, Raman and 1 H-NMR. The co-copolyamide films, DHTH and DDTD, exhibited rms-roughness values between 0.94 and 1.60 nm, respectively. Moreover, they presented good thermal stability up to300 °C. Young's moduli of the co-polyamide films were between 4.1 and 4.3 GPa. X-ray diffraction results showed that the co-polyamide films were amorphous due to the incorporation of both bulky pendant groups, tert-butyl and dibenzobarrelene. The combination of bulky pendant groups provided intrinsically transparent co-polyamide films with a transmittance higher than 88% in the range of 400-780 nm.Due to these outstanding film and optical properties, they are suggested to be flexible substrates in applications for solar cell and other portable electronic devices.
Two aromatic co-polyamides were synthesized combining two diacid monomers containing bulky pendant groups, 5-(9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximido)isophthalic acid(DEAIA) and 5-tert-butylisophthalic acid(TERT), with 4,4′-(hexafluoroisopropylidene)dianiline(HFA) or 2,3,5,6-tetramethyl-1,4-phenylenediamine(Durene) by direct polycondensation. The structures of the obtained aromatic co-polyamides were confirmed by FTIR, Raman and 1 H-NMR. The co-copolyamide films, DHTH and DDTD, exhibited rms-roughness values between 0.94 and 1.60 nm, respectively. Moreover, they presented good thermal stability up to300 °C. Young's moduli of the co-polyamide films were between 4.1 and 4.3 GPa. X-ray diffraction results showed that the co-polyamide films were amorphous due to the incorporation of both bulky pendant groups, tert-butyl and dibenzobarrelene. The combination of bulky pendant groups provided intrinsically transparent co-polyamide films with a transmittance higher than 88% in the range of 400-780 nm.Due to these outstanding film and optical properties, they are suggested to be flexible substrates in applications for solar cell and other portable electronic devices.
引文
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7 Meng, S.; Sun, N.; Su,K. Optically transparent polyamides bearing phenoxyl, diphenylamine and fluorene units with highcontrast of electrochromic and electrofluorescent behaviors.Polymer 2017,116, 89-98.
8 Garcia, J. M.; Garcia, F. C.; Serna, F.; de la Pena, J. L. Highperformance aromatic polyamides. Prog. Polym. Sci. 2010, 35,623-686.
9 Liaw,D. J.; Chen,W. H.; Hu,C. K.; Lee,K. R.; Lai,J. Y. High optical transparency, low dielectric constant and light color of novel organosoluble polyamides with bulky alicyclic pendent group. Polymer 2007, 48, 6571-6580.
10 Kim, Y.; Chang, J. Colorless and transparent polyimide nanocomposites:Thermo-optical properties, morphology, and gas permeation. Macromol. Res. 2013, 21, 228-233.
11 Huang, W.; Yin, J. Synthesis, photophysical properties, and electron paramagnetic resonance studies of new poly(bisben-zothiazole)s containing bulky pendant groups. Polym. Eng. Sci.2007, 47, 429-438.
12 De Abajo, J.; de la Campa, J. G. Processable aromatic polyimides.Adv. Polym. Sci. 1999, 140, 23-59.
13 Santiago-Garcia, J. L.; Perez-Francisco, J. M.; Loria-Bastarrachea, M. I.; Aguilar-Vega, M. Synthesis and characterization of novel polyamides containing dibenzobarrelene pendant groups. Des. Monomers Polym. 2015, 18, 350-359.
14 Yamazaki, N.; Higashi, F.; Matsumoto, M. 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.Chem. 1975, 13, 1373-1380.
15 Huerta, E.; Corona, J.; Oliva, A. I. Universal testing machine for mechanical properties of thin materials. Rev. Mex. Fis.2010, 56,317-322.
16 Bera,D.; Dasgupta,B.; Chatterjee,S.; Maji,S.; Banerjee,S.Synthesis, characterization, and properties of semifluorinated organo-soluble new aromatic polyamides. Polym. Adv. Technol.2012, 23, 77-84.
17 Mittal,V. in High performance polymers and engineering plastics, Scrivener Publishing LLC, Massachusetts, 2011, p. 1-20.
18 Johannes, K. F. in High performance polymers, William Andrew, New York, 2014, p. 321-341.
19 Ando, S.; Matsuura, T.; Sasaki, S. Coloration of aromatic polyimides and electronic properties of their source materials.Polym. J. 1997, 29, 69-76.
20 Yi, L.; Li, C.; Huang, W.; Yan, D. Soluble and transparent polyimides with high Tg from a new diamine containing tertbutyl and fluorene units. J. Polym. Sci. Part A:Polym. Chem:2016, 54, 976-984.
21 Ge, Z.; Yang, S.; Tao, Z.; Liu, J.; Fan, L. Synthesis and characterization of novel soluble fluorinated aromatic polyamides derived from fluorinated isophthaloyl dichlorides and aromatic diamines. Polymer 2004, 45, 3627-3635.
22 Javadi, A.; Shockravi, A.; Koohgard, M.; Malek, A.; Shourkaei,F. A.; Ando, S. Nitro-substituted polyamides:A new class of transparent and highly refractive materials. Eur. Polym. J.2015, 66, 328-341.
23 Liaw, D. J.; Huang, C. C.; Chen, W. H. Color lightness and highly organosoluble fluorinated polyamides, polyimides and poly(amide-imide)s based on noncoplanar 2,2'-dimethyl-4,4'-biphenylene units. Polymer 2006, 47, 2337-2348.
24 Bera, D.; Bandyopadhyay, P.; Ghosh, S.; Banerjee, S. Gas transport properties of aromatic polyamides containing adamantyl moiety.J. Membr. Sci. 2014, 453, 175-191.
25 Hsiao, S. H.; Yang, C. P.; Tsai, C. Y.; Liou, G. S. A novel class of organosoluble and light-colored fluorinated polyamides derived from 2,2'-bis(4-amino-2-trifluoromethylphenoxy)biphenyl or 2,2'-bis(4-amino-2-trifluoromethylphenoxy)-1,1'-binaphthyl. Eur. Polym. J. 2004, 40, 1081-1094.
26 Liaw, D. J.; Wang, K. L.; Huang, Y. C.; Lee, K. R.; Lai, J. Y.;Ha, C. S. Advanced polyimide materials:Syntheses, physical properties and applications. Prog. Polym. Sci. 2012,37,907-974.
2 Wang, Q.; Xie, Y.; Soltani-kordshuli, F.; Eslamian, M. Progress in emerging solution-processed thin film solar cells-Part I:Polymer solar cells. Renew. Sustain. Energy Rev. 2016, 56,347-361.
3 Krebs, F. C. in Polymeric solar cells:Materials, design, manufacture, DEStech Publications, Inc., Pennsylvania, 2010, p. 15.
4 Sibinski, M.; Znajdek, K. in Innovative elastic thin-film solar cell structures, InTech, Rijeka, 2011, p. 253-274.
5 Ni,H.; Liu, J.; Wang,Z.; Yang, S. A review on colorless and optically transparent polyimide films:Chemistry, process and engineering applications. J. Ind. Eng. Chem. 2015, 28, 16-27.
6 Santiago-Garcia, J. L.; Perez-Francisco J. M.; Zolotukhin, M.G.; Vazquez-Torres, H.; Aguilar-Vega, M.; Gonzalez-Diaz,M.O. Gas transport properties of novel aromatic poly-and copolyamides bearing bulky functional groups. J. Membr. Sci.2017, 522, 333-342.
7 Meng, S.; Sun, N.; Su,K. Optically transparent polyamides bearing phenoxyl, diphenylamine and fluorene units with highcontrast of electrochromic and electrofluorescent behaviors.Polymer 2017,116, 89-98.
8 Garcia, J. M.; Garcia, F. C.; Serna, F.; de la Pena, J. L. Highperformance aromatic polyamides. Prog. Polym. Sci. 2010, 35,623-686.
9 Liaw,D. J.; Chen,W. H.; Hu,C. K.; Lee,K. R.; Lai,J. Y. High optical transparency, low dielectric constant and light color of novel organosoluble polyamides with bulky alicyclic pendent group. Polymer 2007, 48, 6571-6580.
10 Kim, Y.; Chang, J. Colorless and transparent polyimide nanocomposites:Thermo-optical properties, morphology, and gas permeation. Macromol. Res. 2013, 21, 228-233.
11 Huang, W.; Yin, J. Synthesis, photophysical properties, and electron paramagnetic resonance studies of new poly(bisben-zothiazole)s containing bulky pendant groups. Polym. Eng. Sci.2007, 47, 429-438.
12 De Abajo, J.; de la Campa, J. G. Processable aromatic polyimides.Adv. Polym. Sci. 1999, 140, 23-59.
13 Santiago-Garcia, J. L.; Perez-Francisco, J. M.; Loria-Bastarrachea, M. I.; Aguilar-Vega, M. Synthesis and characterization of novel polyamides containing dibenzobarrelene pendant groups. Des. Monomers Polym. 2015, 18, 350-359.
14 Yamazaki, N.; Higashi, F.; Matsumoto, M. 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.Chem. 1975, 13, 1373-1380.
15 Huerta, E.; Corona, J.; Oliva, A. I. Universal testing machine for mechanical properties of thin materials. Rev. Mex. Fis.2010, 56,317-322.
16 Bera,D.; Dasgupta,B.; Chatterjee,S.; Maji,S.; Banerjee,S.Synthesis, characterization, and properties of semifluorinated organo-soluble new aromatic polyamides. Polym. Adv. Technol.2012, 23, 77-84.
17 Mittal,V. in High performance polymers and engineering plastics, Scrivener Publishing LLC, Massachusetts, 2011, p. 1-20.
18 Johannes, K. F. in High performance polymers, William Andrew, New York, 2014, p. 321-341.
19 Ando, S.; Matsuura, T.; Sasaki, S. Coloration of aromatic polyimides and electronic properties of their source materials.Polym. J. 1997, 29, 69-76.
20 Yi, L.; Li, C.; Huang, W.; Yan, D. Soluble and transparent polyimides with high Tg from a new diamine containing tertbutyl and fluorene units. J. Polym. Sci. Part A:Polym. Chem:2016, 54, 976-984.
21 Ge, Z.; Yang, S.; Tao, Z.; Liu, J.; Fan, L. Synthesis and characterization of novel soluble fluorinated aromatic polyamides derived from fluorinated isophthaloyl dichlorides and aromatic diamines. Polymer 2004, 45, 3627-3635.
22 Javadi, A.; Shockravi, A.; Koohgard, M.; Malek, A.; Shourkaei,F. A.; Ando, S. Nitro-substituted polyamides:A new class of transparent and highly refractive materials. Eur. Polym. J.2015, 66, 328-341.
23 Liaw, D. J.; Huang, C. C.; Chen, W. H. Color lightness and highly organosoluble fluorinated polyamides, polyimides and poly(amide-imide)s based on noncoplanar 2,2'-dimethyl-4,4'-biphenylene units. Polymer 2006, 47, 2337-2348.
24 Bera, D.; Bandyopadhyay, P.; Ghosh, S.; Banerjee, S. Gas transport properties of aromatic polyamides containing adamantyl moiety.J. Membr. Sci. 2014, 453, 175-191.
25 Hsiao, S. H.; Yang, C. P.; Tsai, C. Y.; Liou, G. S. A novel class of organosoluble and light-colored fluorinated polyamides derived from 2,2'-bis(4-amino-2-trifluoromethylphenoxy)biphenyl or 2,2'-bis(4-amino-2-trifluoromethylphenoxy)-1,1'-binaphthyl. Eur. Polym. J. 2004, 40, 1081-1094.
26 Liaw, D. J.; Wang, K. L.; Huang, Y. C.; Lee, K. R.; Lai, J. Y.;Ha, C. S. Advanced polyimide materials:Syntheses, physical properties and applications. Prog. Polym. Sci. 2012,37,907-974.