Cyclic and non cyclic aliphatic–aromatic polyesters derived from biomass: Study of structures by MALDI-ToF and NMR

Abderrazak, Hana Ben; Fildier, Aurélie; Marque, Sylvain R. A.; Prim, Damien; Romdhane, Hatem Ben; Kricheldorf, Hans R.; Chatti, Saber

doi:10.1016/j.eurpolymj.2011.07.009

Cited by 17 publications

(11 citation statements)

References 40 publications

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“…Dianhydrohexitols are considered as one of the promising building blocks. 23 They have been used in several polymer syntheses 24 such as polyesters, 25 polyethers, 26,27,28 polyurethanes, 29,30,31 and polyethersulfones. 32 Recently, we reported the synthesis of linear homo and coPEKs based on dianhydrohexitols.…”

Section: Introductionmentioning

confidence: 99%

Hyperbranched cyclic and multicyclic poly(etherketone)s by polycondensation of isosorbide and isomannide with 2,6,4′-trifluorobenzophenone and 1,3,5-tris(4-fluorobenzoyl) benzene

Bennour¹,

Medimagh²,

Fildier

et al. 2013

High Performance Polymers

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International audience1,3,5-Tris(4-fluorobenzoyl)benzene (TFBB) and 2,6,4′-trifluorobenzophenone (TFB) were polycondensed with isosorbide and isomanide. All polycondensations were performed in a mixture of dimethyl sulfoxide and toluene with potassium carbonate as promotor. Optimal concentration to avoid gelation was set at 0.06 mol L−1. The different cyclization tendencies on the basis of monomers conformations are discussed. In the TFB series, the feed ratio isosorbide/TFB was varied from 1.0:1.0 to 1.5:1.0. A majority of linear and hyperbranched species were identified as main reaction products by matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry regardless of the diol with slight cyclization tendency for isomannide. When TFBB was polycondensed with isosorbide, the cyclization tendency was significantly improved. The products obtained at a feed ratio of 1.41/1.0 and 1.51/1.0 were rich in cyclic and multicyclic species. More interesting results were obtained from the polycondensation of TFBB and isomannide, giving rise majoritarily to cyclic, bicyclic, and multicyclic species. Differential scanning calorimetric measurements indicated high glass transition temperature (around 200°C)

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Section: Introductionmentioning

confidence: 99%

Hyperbranched cyclic and multicyclic poly(etherketone)s by polycondensation of isosorbide and isomannide with 2,6,4′-trifluorobenzophenone and 1,3,5-tris(4-fluorobenzoyl) benzene

Bennour¹,

Medimagh²,

Fildier

et al. 2013

High Performance Polymers

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“…This result underlines the effect of the diol structure on the thermal behavior of these polyesters. Obviously, the cardonature of the former hinders the segmental motion more than isosorbide . As indicated by the DSC thermogram, the copolymer (curve C, Figure ) has only one glass transition temperature at 172 °C higher than the T g value of both homopolyesters.…”

Section: Resultsmentioning

confidence: 95%

Biosourced Cyclic and Multicyclic Polyesters Based on 1,4:3,6-Dianhydrohexitols: Application to Metal Ions Uptake in Aqueous Media

Bennour¹,

Fildier

Chatti

et al. 2015

Macromol. Chem. Phys.

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Authors want to thank all INRAP staff for analysis and helpful discussion. M. Mezni is acknowledged for NMR experiments, R. Jebali and N. Chaabane for ICP analysis.International audienceIsosorbide and isomannide are polycondensed in solution with trimesoyl chloride at a concentration of 0.06 mol L-1 for the synthesis of cyclic and multicyclic polyesters. The feed ratio diol/trimesoyl chloride is varied from 1.0/1.0 to 1.6/1.0. As all obtained polyesters prove insoluble, innovative solvent-free matrix assisted laser desorption ionization time-of-flight mass spectrometry (MALDI ToF MS) is performed for their characterization. The influence of the stereochemistry is shown to be of great importance for the cyclization trend. Both isosorbide and isomannide lead mainly to cyclic and multicyclic structures at a feed ratio of 1.0/1.0 and 1.1/1.0. Isomannide gives higher fractions of multicyclic structures. The products are characterized by complementary techniques such as C-13 cross polarization magic angle spinning nuclear magnetic resonance (C-13 CP-MAS NMR) and differential scanning calorimetry measurements. Application as a cryptands for the uptake of metal ions in aqueous media is followed by inductively coupled plasma atomic emission spectroscopy (ICP AES) analysis and reveal efficient toward large range of metals with tunable selectivity depending on the starting diol

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“…The importance of the DAHs has increased recently due to the chirality associated with their rigidity, which gave some enhanced properties of synthesized polycondensates . The use of biosourced diols as monomers was extensively reported for polymers, such as polyesters, poly(esteramide), poly(ethersulfones), poly(etherketones), polyamides, polyethers, and polyurethanes . The properties of dianhydrohexitol‐based polymers, as well as the biodegradability of several types of dianhydrohexitol‐based polymers, are emphasized in these papers.…”

Section: Introductionmentioning

confidence: 99%

New biosourced chiral molecularly imprinted polymer: Synthesis, characterization, and evaluation of the recognition capacity of methyltestosterone

Saadaoui

Sanglar

Medimagh³

et al. 2016

J of Molecular Recognition

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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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Cyclic and non cyclic aliphatic–aromatic polyesters derived from biomass: Study of structures by MALDI-ToF and NMR

Cited by 17 publications

References 40 publications

Hyperbranched cyclic and multicyclic poly(etherketone)s by polycondensation of isosorbide and isomannide with 2,6,4′-trifluorobenzophenone and 1,3,5-tris(4-fluorobenzoyl) benzene

Hyperbranched cyclic and multicyclic poly(etherketone)s by polycondensation of isosorbide and isomannide with 2,6,4′-trifluorobenzophenone and 1,3,5-tris(4-fluorobenzoyl) benzene

Biosourced Cyclic and Multicyclic Polyesters Based on 1,4:3,6-Dianhydrohexitols: Application to Metal Ions Uptake in Aqueous Media

New biosourced chiral molecularly imprinted polymer: Synthesis, characterization, and evaluation of the recognition capacity of methyltestosterone

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