New series of polyether-amides were prepared by polycondensation in solution of three diamines based on 1,4-3,6-dianhydrohexitols with two types of diacyl chlorides (sebacoyl and isophtaloyl). Unprecedented diamines based on isomannide and isoidide were elaborated. The corresponding polyether-amides (PeA) were obtained with high yields. They were characterized by different analytical techniques (NMR, MALDI-ToF MS, DSC). The combination of MALDI-ToF MS with NMR spectroscopy allowed us to confirm structure types. DSC measurements revealed an amorphous character for the isophtaloyl family with a high T g value. The sebacoyl series proved to be semi-crystalline with a high T m value. Isosorbide-based PeAs demonstrated interesting properties (T g above 210 8C and T m above 240 8C) and high viscosity (0.32).
International audienceNew biosourced alternated poly(ether)Ester-Amides PeEA were prepared by polycondensation in solution or in bulk of unprecedented aminoalcohols based on 1,4:3,6-dianhydrohexitols (DAH) with aromatic and aliphatic diacyl chlorides (sebacoyl, terephtaloyl and isophtaloyl). Optimization of the polymerization in solution has been investigated using MALDI ToF MS and NMR spectroscopy to ascertain the structures and end chain nature of the resulting polymers. The influence of the DAH stereochemistry and the polymerization mode on the structures and thermal properties was demonstrated by MALDI ToF and complementary analytical techniques (DSC and SEC). Isomannide based polymers revealed amorphous but showed higher Tg (around 80 °C for sebacoyl and 180 °C for isophtaloyl) whereas the isosorbide based polymers were semi crystalline. Best properties were obtained in bulk using isomannide based aminoalcohol and sebacoyl chloride (Tg of 82 °C and Mw of 32 kDa, PDI = 1.41)
New biosourced chiral cross-linkers were reported for the first time in the synthesis of methyltestosterone (MT) chiral molecularly imprinted polymers (cMIPs). Isosorbide and isomannide, known as 1,4:3,6-dianhydrohexitols, were selected as starting diols. The cMIPs were synthesized following a noncovalent approach via thermal radical polymerization and monitored by Raman spectroscopy. These cross-linkers were fully characterized by H and C nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry. The cross-polarization magic angle spinning C NMR, Fourier transform infrared spectroscopy, scanning electron microscopy, and specific surface areas following the Brunauer-Emmett-Teller (BET) method were used to characterize the cMIPs. The effect of stereochemistry of cross-linkers on the reactivity of polymerization, morphology, and adsorption-recognition properties of the MIP was evaluated. The results showed that the cMIP exhibited an obvious improvement in terms of rebinding capacity for MT as compared with the nonimprinted polymer (NIP). The highest binding capacity was observed for cMIP-Is (27.298 mg g ) for high concentrations (500 mg L ). However, the isomannide homologue cMIP-Im showed higher recovery-up to 65% and capacity for low concentrations (15 mg L ). The experimental data were properly fitted by the Freundlich adsorption isothermal model.
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