This work reports on the synthesis of a series of new sulfonated fluorine-containing aromatic polyamides with increasing degree of sulfonation (DS). The chemical structure of the resulting polymers was confirmed by Fourier transform infrared spectroscopy and proton nuclear magnetic resonance (1 H NMR) which evidenced the presence of amide and sulfonic groups in the proposed concentrations. Afterwards, we carried out a comparative study of heavy metal ion adsorption in membranes based on these aromatic polyamides. The main purpose was to determine the adsorption capacity of the prepared polymer membranes toward Pb 2þ and Hg 2þ in aqueous media at 30 C and pH neutral. The adsorption kinetics was evaluated with the pseudo-first-order and pseudo-second-order models. The adsorption kinetics in all the polyamide membranes followed the pseudo-second-order rate law for both heavy metal ions. It is observed that the adsorption capacities of all the polyamides toward Pb 2þ ions are higher than those of the Hg 2þ ions, and these capacities increase as the DS increases. The equilibrium adsorption amounts, q e , were 11.87 mg/g for Pb 2þ and 5.17 mg/g for Hg 2þ ions for the highest sulfonated polymer.
This work reports on the synthesis and ring-opening metathesis polymerization (ROMP) of new structural isomers based on norbornene dicarboximides bearing trifluoromethyl moieties, specifically, N-2-trifluoromethylphenyl- exo- endo-norbornene-5,6-dicarboximide (2a) and N-3-trifluoromethylphenyl- exo- endo-norbornene-5,6-dicarboximide (2b) using tricyclohexylphosphine [1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene] ruthenium dichloride (I), bis(tricyclohexylphosphine) benzylidene ruthenium (IV) dichloride (II), and bis(tricyclohexylphosphine) p-fluorophenylvinylidene ruthenium (II) dichloride (III). It is observed that the –CF3 moiety attached to the ortho position of the aromatic ring increases the thermal and mechanical properties of the polymer, whereas the meta substitution has the opposite effect. A comparative study of gas transport in membranes based on these fluorinated polynorbornenes showed that the –CF3 ortho substitution increases the permeability of the polymer membrane as a consequence of the increase of both the gas solubility and the gas diffusion. In contrast, the gas permeability coefficients of the meta-substituted polymer membrane are rather similar to those of the non-fluorinated one attributed to a lower fractional free volume. The meta-substituted polymer membrane besides showing the largest permselectivity coefficients of all the isomers studied here was also found to have one of the largest permselectivity coefficients reported to date for separating hydrogen/propylene in glassy polynorbornene dicarboximides.
The synthesis and further hydrogenation of fl uorinated polynorbornene dicarboximides is reported, using p -toluenesulfonyl hydrazide and Wilkinson's catalysts, respectively. Despite improving the resistance to thermo-oxidative degradation, it is observed that the hydrogenation of the backbone double bonds in the polymer also decreases the thermomechanical properties. Afterward, a comparative study of gas transport in membranes based on these hydrogenated polynorbornenes, as well as in their unsaturated analogues, is carried out. The gases studied are hydrogen, oxygen, nitrogen, carbon dioxide, methane, ethane, ethylene, and propylene. After hydrogenation, the gas permselectivity of the membranes is enhanced as a consequence of the decrease of both the gas solubility and the gas diffusion.
This study describes the synthesis of two new families of dendrimers based on the esterification of N-alkylated 3-amine-1-propanol with two different cores, adipic acid (1st and 2nd generations) and ethylenediamine (generation 1.5), both with carboxylic acid end groups, offering a wide variety of further modifications at the periphery. According to the cytotoxic evaluation of the dendrimers and their possible degradation products within cell lines, these materials could be considered as innocuous. In preliminary studies, the synthesized dendrimers proved to be potential enhancers of solubility of highly hydrophobic drugs, like methotrexate, widely used in chemotherapy.
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