Abstract
The following work shows, for the first time, the synthesis and characterization of a new family of polyelectrolytes, along with their preliminary assessments in terms of desalin water treatment. These materials fall into the category of aromatic co-polyamides, which are obtained by the direct condensation of monomers 4,4′-oxydianiline (ODA), isophthaloyl chloride, and 3,5-diamino-N-(pyridin-4-ylmethyl)benzamide (PyMDA). Thereby, the charged nature exhibited by these materials was achieved through the quaternization of PyMDA moieties using linear iodoalkanes of different lengths (CnI with n = 1, 2, 4, and 6). After completing the quaternization process, polyelectrolytes were subjected to a one-step anion substitution process, where iodide counterions were replaced by bis(trifluoromethane)sulfonamide entities. For all the obtained materials, solubility tests were carried out, showing that those alkylated with methyl and ethyl chains exhibit high solubility in rutinary aprotic polar solvents, while those containing n-butyl and n-hexyl units resulted in the formation of insoluble gels. Due to the above, the latest were discarded from this study early on. The structural characterization of the initial neutral co-polyamide was carried out by means of infrared spectroscopy (FT-IR), nuclear magnetic resonance (1H, 13C-NMR), and size-exclusion chromatography (SEC), while the structure of methylated and ethylated polyelectrolytes was successfully confirmed through FT-IR, 1H, 13C, and 19F-NMR. Additionally, the thermal behavior of these materials was analyzed in terms of thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC), showing thermal degradation temperatures above 300 °C and glass transition temperatures (Tg) above 200 °C, resulting in polymers with outstanding thermal properties for water treatment applications. On the other hand, through the solvent-casting method, both neutral and charged polymers were found to be easily prepared into films, exhibiting a remarkably flexibility. The mechanical properties of the films were analyzed using the traction test, from which tensile strength values ranging between 83.5 and 87.9 Mpa, along with Young’s modulus values between 2.4 and 2.5 Gpa were obtained. Moreover, through contact angle measurements and absorption analysis by immersion, polyelectrolytes showed important changes in terms of affinity against polar and polar substances (water, n-heptane, and benzene), exhibiting a higher rejection regarding the neutral polymer. Finally, as a preliminary test against the seepage of saline waters, thin polymer films (from 11.4 to 17.1 µm) were deposited on top of commercial filter discs and tested as filters of saline solutions ([NaCl] = 1000 and 2000 ppm). These tests revealed a decrease of the salt concentration in the obtained filtrates, with retention values ranging between 6.2 and 20.3%, depending on the concentration of the former solution and the polymer used.
Highlights
In recent years, the rapid growth of the population and its constant demand for various resources such as energy, water, air, and food has generated a strong global concern [1,2,3,4].This has led to the search for new methods and materials that allow obtaining these resources in more efficient and environmentally friendly ways
Ethanol absolute 99.5%, n-hexane 99.5%, diethyl ether 99.5%, tetrahydrofuran 99.5% (THF), lithium bis(trifluoromethanesulfonyl)imide 98.0% (LiTFSI), and hydrazine (80% solution in water) were obtained from Merck
The use of PyMDA results is fundamental for the development of of this work, since it would allow obtaining polyelectrolytesbybythe thedirect directquaternization quaternization this work, since it would allow obtaining polyelectrolytes ofits itspyridinyl pyridinylpendant pendantgroup
Summary
The rapid growth of the population and its constant demand for various resources such as energy, water, air, and food has generated a strong global concern [1,2,3,4]. Within the many advantages of using aromatic polyamides in these processes, are their outstanding mechanical, thermal, and chemical resistance [17] which, together with their chemical and inner structure, allows a high flow of water through it, at the same time as it avoids the passage of the high content of salts that the feed waters present [18] This type of polymers has been shown to be efficient for this kind of application, they are not exempt from problems such as fouling [19] and membrane degradation. The attractive properties such as ionic conductivity, chemical stability, low toxicity, wide electrochemical window, and high mechanical stability that these materials present and the large number of possible applications such as desalination, membrane fouling control, pervaporation, lithium battery, fuel cells, and organic solvent nanofiltration [29,30] make them a focus of study to solve the problems that today afflict society. A preliminary test is carried out to know the permeability to the passage of water and if they are able to avoid the passage of salts
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