Synthesis and Characterization of Easily Colored Meta-aramid Copolymer Containing Ether Bonds
- Corresponding author: Jun-Rong Yu, yjr@dhu.edu.cn
Citation:
Na Li, Xing-Ke Zhang, Jun-Rong Yu, Yan Wang, Jing Zhu, Zu-Ming Hu. Synthesis and Characterization of Easily Colored Meta-aramid Copolymer Containing Ether Bonds[J]. Chinese Journal of Polymer Science,
;2019, 37(3): 227-234.
doi:
10.1007/s10118-019-2200-9
Trigo-López, M.; Miguel-Ortega, Á.; Vallejos, S.; Muñoz, A.; Izquierdo, D.; Colina, Á.; García, F. C.; García, J. M. Intrinsically colored wholly aromatic polyamides (aramids). Dyes Pigments 2015, 122, 177-183.
doi: 10.1016/j.dyepig.2015.06.027
Horrocks, A. R. Flame retardant challenges for textiles and fibres: New chemistry versus innovatory solutions. Polym. Degrad. Stabil. 2011, 96, 377-392.
doi: 10.1016/j.polymdegradstab.2010.03.036
Kim, E. M.; Choi, J. H. Dyeing properties and color fastness of 100%-aramid fiber. Fibers Polym. 2011, 12, 484-490.
doi: 10.1007/s12221-011-0484-7
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.
doi: 10.1134/S0040579507050430
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.
doi: 10.1021/jp013982i
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.
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.
doi: 10.1021/acsomega.6b00527
Islam, M. T.; Aimone, F.; Ferri, A.; Rovero, G. Use of N-methylformanilide as swelling agent for meta-aramid fibers dyeing: Kinetics and equilibrium adsorption of Basic Blue 41. Dyes Pigments 2015, 113, 554-561.
doi: 10.1016/j.dyepig.2014.08.029
Kim, E. M.; Jang, J. Surface modification of meta-aramid films by UV/ozone irradiation. Fibers Polym. 2010, 11, 677-682.
doi: 10.1007/s12221-010-0677-5
Nicolai, M.; Nechwatal, A. The swelling effect of liquid ammonia in the dyeing of aramids. Color. Technol. 2010, 110, 228-230.
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.
Dong, Y.; Jang, J. The enhanced cationic dyeability of ultraviolet/ozone-treated meta-aramid fabrics. Color. Technol. 2011, 127, 173-178.
doi: 10.1111/cote.2011.127.issue-3
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.
doi: 10.1111/cote.2017.133.issue-4
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.
Tansil, N. C.; Koh, L. D.; Han, M. Y. Functional silk: colored and luminescent. Adv Mater. 2012, 24, 1350-1350.
doi: 10.1002/adma.201290064
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 Pigments 2007, 74, 713-722.
doi: 10.1016/j.dyepig.2006.05.007
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.
doi: 10.1016/S0014-3057(02)00304-X
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.
Bojinov, V.; Konstantinova, T. Synthesis of polymerizable 1,8-naphthalimide dyes containing hindered amine fragment. Dyes Pigments 2002, 54, 239-245.
doi: 10.1016/S0143-7208(02)00047-5
Konstantinova, T.; Petrova, P. On the synthesis of some bifunctional reactive triazine dyes. Dyes Pigments 2002, 52, 115-120.
doi: 10.1016/S0143-7208(01)00080-8
Hsiao, S. H.; Lin, K. H. Soluble aromatic polyamides bearing asymmetrical diaryl ether groups. Polymer 2004, 45, 7877-7885.
doi: 10.1016/j.polymer.2004.09.030
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, DOI: 10.1002/app.46341.
doi: 10.1002/app.46341
Liou, G. S.; Maruyama, M.; Kakimoto, M. A.; Imai, Y. Preparation and properties of aromatic polyamides from 2,2’-bis(p-aminophenoxy) 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.
doi: 10.1002/pola.1993.080311010
Imai, Y. Synthesis of novel organic-soluble high-temperature aromatic polymers. High Perform. Polym. 1995, 7, 337-345.
doi: 10.1088/0954-0083/7/3/010
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.
doi: 10.1016/j.polymer.2005.05.059
Krevelen, D. W. V.; Hoftyzer, P. in Properties of polymers, their estimation and correlation with chemical structure, Elsevier Science, Netherlands, 1976, p.119
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.
doi: 10.1002/pol.1977.170150812
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.
doi: 10.1002/pol.1959.1203613063
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.
doi: 10.1007/s13233-012-0007-4
Razafimahefa, L.; Chlebicki, S.; Vroman, I.; Devaux, E. Effect of nanoclay on the dyeing ability of PA6 nanocomposite fibers. Dyes Pigments 2005, 66, 55-60.
doi: 10.1016/j.dyepig.2004.08.012
Trigo-López, M.; Barrio-Manso, J. L.; Serna, F.; García, F. C.; García, J. M. Crosslinked aromatic polyamides: A further step in high-performance materials. Macromol. Chem. Phys. 2013, 214, 2223-2231.
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.
doi: 10.1016/j.eurpolymj.2008.10.023
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.
doi: 10.1016/j.polymdegradstab.2012.05.040
Kim, E. M.; Choi, J. H. Synthesis of cationized anthraquinone dyes and their dyeing properties for meta -aramid fiber. Fibers Polym. 2013, 14, 2054-2060.
doi: 10.1007/s12221-013-2054-7
Fu, C.; Gu, L. Structures and properties of easily dyeable copolyesters and their fibers respectively modified by three kinds of diols. J. Appl.Polym. Sci. 2013, 128, 3964-3973.
doi: 10.1002/app.v128.6
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Zheng Zhao , Ben Zhong Tang . An efficient strategy enabling solution processable thermally activated delayed fluorescence emitter with high horizontal dipole orientation. Chinese Journal of Structural Chemistry, 2024, 43(6): 100270-100270. doi: 10.1016/j.cjsc.2024.100270
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