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Aqueously soluble semi‐aromatic copolyamides with dual‐functional groups as sizing agent
Author(s) -
Qi X.,
Wang W.,
Zhang J.,
Yan C.,
Zhu Y.,
Zhang F.
Publication year - 2019
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.47132
Subject(s) - ethylenedioxy , polymer chemistry , terephthaloyl chloride , ethylene , materials science , copolymer , dimethylformamide , diethanolamine , epoxy , polymer , solvent , chemistry , organic chemistry , catalysis , alkyl
A series of novel aqueously soluble semi‐aromatic (co)polyamides, poly[(ethylenedioxy)bis(ethylene) terephthalamide]‐ ran ‐poly[(ethylenedioxy)bis(ethylene) (2,5‐dihydroxy‐3,6‐diallyl)terephthalamide] (CRPAOT‐x), were prepared via the solid‐state Claisen rearrangement reaction of poly[(ethylenedioxy)bis(ethylene) terephthalamide]‐ ran ‐poly[(ethylenedioxy)bis(ethylene) 2,5‐bis(allyloxy)terephthalamide] (APAOT‐x), where x (= 0, 13, 25, 50, 75, and 100) represents the molar fraction of allyloxy containing unit. APAOT‐x was obtained through the interfacial copolymerization of terephthaloyl chloride, 2,5‐bis(allyloxy)terephthaloyl chloride, and 2,2′‐(ethylenedioxy)bis(ethylamine). The reaction conditions including reactant concentration, temperature, and solvent were optimized. The chemical structures of the target (co)polyamides and their precursors were characterized by proton nuclear magnetic resonance ( 1 H NMR) and Fourier transform infrared spectroscopies. The incorporation of hydrophilic (ethylenedioxy)bis(ethylene) units greatly improved the polymer solubility. CRPAOT‐x dissolved not only in polar organic solvents such as dimethylformamide, dimethyl sulfoxide, and N‐methyl pyrrolidone but also in ammonia water. Due to the presence of hydroxyl groups and oxygen‐rich aliphatic units, CRPAOT‐x showed excellent affinity toward epoxy resins. The microbond test indicated that the aramid fibers sized by these dual‐functional polymers exhibited remarkably enhanced interfacial shear strength in epoxy matrices. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136 , 47132.