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Synthesis and Characterization of Easily Colored Meta-aramid Copolymer Containing Ether Bonds

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Abstract

This work described the preparation of easily colored meta-aramid (PMIA) copolymers from m-phenylenediamine (MPD), isophthaloyl dichloride (IPC), and 3,4′-oxydianiline (3,4′-ODA) via solution polycondensation in N,N-dimethylacetamide (DMAc). The novel co-PMIAs were obtained in relatively high inherent viscosities ranging from 1.32 dL/g to 2.53 dL/g, which could be easily cast into flexible films with high transparence or spun into fibers. All the newly synthesized copolymers possessed excellent thermal stabilities even better than that of commercial PMIA, with 5% weight loss temperatures higher than 430 °C in nitrogen measured by TGA and glass transition temperature of 267–277 °C measured by DSC. The cast films exhibited good mechanical properties with a tensile strength up to 107 MPa and a tensile modulus up to 2.2 GPa. The resultant PMIAs also showed good solubility and better dye ability for cationic dyes.

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References

  1. Trigo-López, M.; Miguel-Ortega, Á.; Vallejos, S.; Muñoz, A.; Izquierdo, D.; Colina, Á.; Garcia, F. C.; García, J. M. Intrinsically colored wholly aromatic polyamides (aramids). Dyes and Pigments 2015,122, 177–183.

    Article  CAS  Google Scholar 

  2. Horrocks, A. R. Flame retardant challenges for textiles and fibres: New chemistry versus innovatory solutions. Polym. Degrad. Stabil. 2011, 96, 377–392.

    Article  CAS  Google Scholar 

  3. Kim, E. M.; Choi, J. H. Dyeing properties and color fastness of 100%-aramid fiber. Fiber. Polym. 2011, 12, 484–490.

    Article  CAS  Google Scholar 

  4. Manyukov, E. A.; Sadova, S. F.; Kecek’Yan, A. S.; Puzikova, N. P.; Baeva, N. N. Heat-resistant para/meta-aramid fiber Arlana: Dyeing and the properties of the dyed materials. Theor. Found. Chem. Eng. 2007, 41, 698–702.

    Article  CAS  Google Scholar 

  5. Nimmanpipug, P.; Tashiro, K.; Maeda, Y.; Rangsiman, O. Factors governing the three-dimensional hydrogen bond network structure of poly(m-phenylene isophthalamide) and a series of its model compounds: (1) Systematic classification of structures analyzed by the X-ray diffraction method. J. Phys. Chem. B 2002, 106, 6842–6848.

    Article  CAS  Google Scholar 

  6. Kim, T.; Kim, G.; Park, J. Y.; Lim, J. S.; Yoo, K. P. Solubility measurement and dyeing performance evaluation of aramid NOMEX yarn by dispersed dyes in supercritical carbon dioxide. Ind. Eng. Chem. Res. 2005, 45, 3425–3433.

    Article  CAS  Google Scholar 

  7. Ouyang, S.; Wang, T.; Yu, Y.; Yang, B.; Yao, J.; Wang, S. From trans to cis conformation: Further understanding the surface properties of poly(m-phenylene isophthalamide). ACS Omega 2017, 2, 290–298.

    Article  CAS  Google Scholar 

  8. Islam, M. T.; Aimone, F.; Ferri, A.; Rovero, G. Use of Nmethylformanilide as swelling agent for meta-aramid fibers dyeing: Kinetics and equilibrium adsorption of Basic Blue 41. Dyes and Pigments 2015, 113, 554–561.

    Article  CAS  Google Scholar 

  9. Kim, E. M.; Jang, J. Surface modification of meta-aramid films by UV/ozone irradiation. Fiber. Polym. 2010, 11, 677–682.

    Google Scholar 

  10. Nicolai, M.; Nechwatal, A. The swelling effect of liquid ammonia in the dyeing of aramids. Color. Technol. 2010, 110, 228–230.

    Google Scholar 

  11. Peila, R.; Aimone, F.; Migliavacca, G.; Alongi, J.; Ferri, A.; Rovero, G. In Dyeing of aramids: a comparison between two industrial swelling agents, Autex2011-World Textile Conference, 2011.

    Google Scholar 

  12. Dong, Y.; Jang, J. The enhanced cationic dyeability of ultraviolet/ozone-treated meta-aramid fabrics. Color. Technol. 2011, 127, 173–178.

    Article  CAS  Google Scholar 

  13. Sheng, D.; Wang, Y.; Wang, X.; Lu, X.; Jiang, S.; Pan, H.; Cao, G.; Xu, W. Low-temperature dyeing of meta-aramid fabrics pretreated with 2-phenoxyethanol. Color. Technol. 2017, 133, 320–324.

    Article  CAS  Google Scholar 

  14. Kobayashi, S.; Wakida, T.; Niu, S.; Hazama, S.; Ito, T.; Sasaki, Y. The effect of sputter etching on the surface characteristics of dyed aramid fabrics. Color. Technol. 1995,111, 72–76.

    CAS  Google Scholar 

  15. Tansil, N. C.; Koh, L. D.; Han, M. Y. Functional silk: Colored and luminescent. Adv. Mater. 2012, 24, 1350–1350.

    Article  CAS  Google Scholar 

  16. Mallakpour, S.; Rafiemanzelat, F.; Faghihi, K. Synthesis and characterization of new self-colored thermally stable poly(amide-ether-urethane)s based on an azo dye and different diisocyanates. Dyes and Pigments 2007, 74, 713–722.

    Article  CAS  Google Scholar 

  17. Al-Muaikel, N. S. Synthesis and characterization of new unsaturated polyesters and copolyesters containing azo groups in the main chain. Eur. Polym. J. 2003, 39, 1025–1033.

    Article  CAS  Google Scholar 

  18. Patel, M. P.; Modi, B. J.; Patel, R. G.; Patel, V. S. Studies of novel water-soluble colored polyesters containing azo moiety. J. Appl. Polym. Sci. 2015, 68, 2041–2048.

    Article  Google Scholar 

  19. Bojinov, V.; Konstantinova, T. Synthesis of polymerizable 1,8-naphthalimide dyes containing hindered amine fragment. Dyes and Pigments 2002, 54, 239–245.

    Article  CAS  Google Scholar 

  20. Konstantinova, T.; Petrova, P. On the synthesis of some bifunctional reactive triazine dyes. Dyes and Pigments 2002, 52, 115–120.

    Article  CAS  Google Scholar 

  21. Hsiao, S. H.; Lin, K. H. Soluble aromatic polyamides bearing asymmetrical diaryl ether groups. Polymer 2004, 45, 7877–7885.

    Article  CAS  Google Scholar 

  22. Zhou, S.; Wang, X.; Zhang, W.; Zhang, M.; Zhang, X.; Zhao, N.; Liu, R.; Xu, J.; Shen, Z.; Fan, X. Facile preparation and characterization of soluble aramid. J. Appl. Polym. Sci. 2018, 135, 46341.

    Google Scholar 

  23. Liou, G. S.; Maruyama, M.; Kakimoto, M. A.; Imai, Y. Preparation and properties of aromatic polyamides from 2,2′-bis(paminophenoxy) biphenyl or 2,2′-bis(p-aminophenoxy)-1,1′-binaphthyl and aromatic dicarboxylic acids. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 2499–2506.

    Article  CAS  Google Scholar 

  24. Imai, Y. Synthesis of novel organic-soluble high-temperature aromatic polymers. High Perform. Polym. 1995, 7, 337–345.

    Article  CAS  Google Scholar 

  25. Liang, Q.; Liu, P.; Liu, C.; Jian, X.; Hong, D.; Li, Y. Synthesis and properties of lyotropic liquid crystalline copolyamides containing phthalazinone moiety and ether linkages. Polymer 2005, 46, 6258–6265.

    Article  CAS  Google Scholar 

  26. Krevelen, D. W. V.; Hoftyzer, P. in Properties of polymers, their estimation and correlation with chemical structure, Elsevier Science, Netherlands, 1976, p.119

    Google Scholar 

  27. Takatsuka, R.; Uno, K.; Toda, F.; Iwakura, Y. Study on wholly aromatic polyamides containing methyl-substituted phenylene linkage. J. Polym. Sci., Part A: Polym. Chem. 1977, 15, 1905–1915.

    CAS  Google Scholar 

  28. Varadaiah, V. V.; Rao, V. S. R. Relation between molecular weight and root-mean-square end-to-end distance of randomly coiled macromolecules. J. Appl. Polym. Sci. 1959, 36, 558–560.

    Article  CAS  Google Scholar 

  29. Zeng, K.; Guo, Q.; Gao, S.; Wu, D.; Fan, H.; Yang, G. Studies on organosoluble polyimides based on a series of new asymmetric and symmetric dianhydrides: Structure/solubility and thermal property relationships. Macromol. Res. 2012, 20, 10–20.

    Article  CAS  Google Scholar 

  30. Razafimahefa, L.; Chlebicki, S.; Vroman, I.; Devaux, E. Effect of nanoclay on the dyeing ability of PA6 nanocomposite fibers. Dyes and Pigments 2005, 66, 55–60.

    Article  CAS  Google Scholar 

  31. Trigo-López, M.; Barrio-Manso, J. L.; Serna, F.; Garcia, F. C.; Garcia, J. M. Crosslinked aromatic polyamides: A further step in high-performance materials. Macromol. Chem. Phys. 2013, 214, 2223–2231.

    Google Scholar 

  32. Sheng, S. R.; Pei, X. L.; Huang, Z. Z.; Liu, X. L.; Song, C. S. Novel soluble fluorinated aromatic polyamides derived from 2-(4-trifluoromethylphenoxy)terephthaloyl chloride with various aromatic diamines. Eur. Polym. J. 2009, 45, 230–236.

    Article  CAS  Google Scholar 

  33. Yuabc, G.; Liu, J.; Wu, S.; Tan, H.; Panab, C. Novel thermally stable and organosoluble aromatic polyamides with main chain phenyl-1,3,5-triazine moieties. Polym. Degrad. Stabil. 2012, 97, 1807–1814.

    Article  CAS  Google Scholar 

  34. Kim, E. M.; Choi, J. H. Synthesis of cationized anthraquinone dyes and their dyeing properties for meta-aramid fiber. Fiber. Polym. 2013,14, 2054–2060.

    Article  CAS  Google Scholar 

  35. Fu, C.; Gu, L. Structures and properties of easily dyeable co-polyesters and their fibers respectively modified by three kinds of diols. J. Appl. Polym. Sci. 2013, 128, 3964–3973.

    Article  CAS  Google Scholar 

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (No. 51473031) and the Shanghai International S&T Cooperation Fund (No. 16160731302).

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Correspondence to Jun-Rong Yu.

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Li, N., Zhang, XK., Yu, JR. et al. Synthesis and Characterization of Easily Colored Meta-aramid Copolymer Containing Ether Bonds. Chin J Polym Sci 37, 227–234 (2019). https://doi.org/10.1007/s10118-019-2200-9

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  • DOI: https://doi.org/10.1007/s10118-019-2200-9

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