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

Na Li; Xing-Ke Zhang; Jun-Rong Yu; Yan Wang; Jing Zhu; Zu-Ming Hu

doi:10.1007/s10118-019-2200-9

Your Location：

Home >

Browse articles >

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

ARTICLE | Updated：2021-02-18

- Synthesis and Characterization of Easily Colored Meta-aramid Copolymer Containing Ether Bonds
- Synthesis and Characterization of Easily Colored Meta-aramid Copolymer Containing Ether Bonds
- Chinese Journal of Polymer Science 2019年37卷第3期页码：227-234
- Affiliations：
  
  State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, China
- Author bio：
  
  yjr@dhu.edu.cn
- Funds：
  
  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).
- DOI：10.1007/s10118-019-2200-9
  中图分类号：
- 收稿：2018-09-03，
  
  修回：2018-10-18，
  
  录用：2018-11-3，
  
  网络首发：2018-12-14，
  
  纸质出版：2019-03
- Accepted：
Scan QR Code
Citation: Li, N.; Zhang, X. K.; Yu, J. R.; Wang, Y.; Zhu, J.; Hu, Z. M. Synthesis and characterization of easily colored meta-aramid copolymer containing ether bonds. Chinese J. Polym. Sci. 2019, 37, 227–234

Na Li, Xing-Ke Zhang, Jun-Rong Yu, et al. Synthesis and Characterization of Easily Colored Meta-aramid Copolymer Containing Ether Bonds[J]. Chinese Journal of Polymer Science, 2019, 37(3): 227-234.
Citation: Li, N.; Zhang, X. K.; Yu, J. R.; Wang, Y.; Zhu, J.; Hu, Z. M. Synthesis and characterization of easily colored meta-aramid copolymer containing ether bonds. Chinese J. Polym. Sci. 2019, 37, 227–234 DOI： 10.1007/s10118-019-2200-9.

Na Li, Xing-Ke Zhang, Jun-Rong Yu, et al. 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.

摘要

Abstract

This work described the preparation of easily colored meta-aramid (PMIA) copolymers from

-phenylenediamine (MPD)

isophthaloyl dichloride (IPC)

and 3

4′-oxydianiline (3

4′-ODA)

via

solution polycondensation in

-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.

关键词

Keywords

references

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 http://doi.org/10.1016/j.dyepig.2015.06.027 .

Horrocks, A. R . Flame retardant challenges for textiles and fibres: New chemistry versus innovatory solutions . Polym. Degrad. Stab. , 2011 . 96 377 - 392 . DOI: 10.1016/j.polymdegradstab.2010.03.036 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 . 135 ( 23 ): 46341 DOI: 10.1002/app.46341 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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. Stab. , 2012 . 97 1807 - 1814 . DOI: 10.1016/j.polymdegradstab.2012.05.040 http://doi.org/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 http://doi.org/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 http://doi.org/10.1002/app.v128.6 .

浏览量

859

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Multiple-Responsive Chiral Hydrogels from Helical Dendronized Poly(phenylacetylene)s

Energy Storage Performance of Supercapacitors with Polyelectrolyte Surface Coatings: Effects of Dielectric Contrast

Epoxy-functionalized Cyclohexane-based Ricinoleate Plasticizer: Synthesis, Performance Evaluation, and Plasticizing Mechanism

End-to-End Neuron-inspired Signal Transduction Using Organic Electrochemical Transistors

Preparation and Chiral Recognition Ability of Crystalline Cellulose Phenylcarbamate