Three diamine monomers (ethylenediamine, butylenediamine, and p-phenylenediamine) were selected for cross-linking graphene oxide (GO) to prepare composite graphene oxide-framework (GOF) membranes through filtration using a pressure-assisted self-assembly technique. The membranes were applied to separate an ethanol−water mixture by pervaporation. Unmodified GO comprised only hydrogen bonds and π−π interactions, but after cross-linking it with a diamine, attenuated total reflectance−Fourier transform infrared and X-ray photoelectron spectroscopy demonstrated that the diamine was chemically bonded both to GO and the membrane support. Moreover, GO hydrophilicity was substantially altered; water contact angle increased from 24.4°to 80.6°(from cross-linking with an aliphatic structure of diamine to cross-linking with an aromatic structure). Results of X-ray diffraction showed that d-spacing in GOF layers varied from 10.4 to 8.7 Å. For GOFs presoaked in 90 wt % ethanol−water, covalent bonds between the layer and diamine could effectively suppress stretching of d-spacing. Cross-linking with ethylenediamine produced a composite membrane that exhibited a short interlayer dspacing and delivered an excellent pervaporation performance at 80 °C: permeation flux = 2297 g/(m 2 h); water concentration in permeate = 99.8 wt %. The membrane showed stability during a long-term operation at 30 °C for 120 h.
Furan-containing benzoxazine monomers, 3-furfuryl-3,4-dihydro-2H-1,3benzoxazine (P-FBz) and bis(3-furfuryl-3,4-dihydro-2H-1,3-benzoxazinyl)isopropane (BPA-FBz), were prepared using furfurylamine as a raw material. The chemical structures of P-FBz and BPA-FBz were characterized with FTIR, 1 H NMR, elemental analysis, and mass spectrometry. Formation of furfurylamine Mannich bridge networks in the polymerizations of P-FBz and BPA-FBz increased the cross-linking densities and thermal stability of the resulting polybenzoxazines. P-FBz-and BPA-FBzbased polymers also exhibited high glass transition temperatures above 300 8C, high char yields, and low flammability with limited oxygen index values of 31. The dielectric (D k ¼ 3.21-3.39) and mechanical properties (high storage modulus of 3.0-3.9 GPa and low coefficient of thermal expansion of 37.7 -45.4 ppm) of the P-FBzand BPA-FBz-based polymers were superior or comparable to other polybenzoxazines.
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