Synthesis and characterization of isosorbide-based α,ω-dihydroxyethersulfone oligomers

Abstract

Functionalization of bio-based oligomers is a relevant approach in order to allow these materials to replace more conventional and nonbiodegradable polymers in a wider range of applications. This article will report on the hydroxylation of isosorbide-based ethersulfone oligomers. The hydroxy end-group was controlled by the variation of polycondensation parameters. Comparative study was conducted to assess the effect of isosorbide excess and the monomer concentration on structural composition and molecular weights of produced oligomers. Depending on reaction conditions, various products were synthesized, mainly α,ω-dihydroxyethersulfone oligomers. The characterization of the synthesized polyethersulfone was demonstrated by MALDI-TOF, NMR spectroscopy, differential scanning calorimetry, and size exclusion chromatography.

New biosourced AA and AB monomers from 1,4:3,6-dianhydrohexitols, Isosorbide, Isomannide, and Isoidide

“…The latter would allow selective modification on the alcohol side considering the nitrile function as an acid precursor. Based on our recent works regarding selective mono arylation on symmetrical Isomannide 2 ,[ 22 ] a similar strategy was considered. Lowering the temperature to 150 °C and using 0.5 eq of arylating agent afforded the desired compound 2c in only one step with 84% yield (Table 1 , entry 12).…”

“…1a or 2a [ 22 ] (4.23 mmol, 1 g), finely ground potassium hydroxide KOH (1.2 eq, 5 mmol, 0.28 mg), 18-crown-6 (10%, 0.112 g),and p -fluorobenzonitrile (1.1 eq, 4.65 mmol, 0.564 g) were placed in a cylindrical reactor equipped with a mechanical stirring. The reaction media was warmed gradually to 170 °C and stirring was maintained during 4 h. The mixture was then cooled to room temperature and the crude was diluted with dichloromethane and filtered through a glass filter with celite and the residue was rinsed with dichloromethane.…”

“…Among our recent efforts in this field we reported the synthesis of three diamines based on Isosorbide ( 1), Isomannide ( 2), and Isoidide ( 3) which were suitably used for the synthesis of polyamides,[ 20 ] and poly(ether)ureas. [ 21 ] Poly(ether)esteramides, as for them, were obtained directly from aminoalcohols [ 22 ] based on Isosorbide and Isomannide or from novel bis amide-diols building blocks. [ 23 ]…”

Copolyethersulfones of 1,4:3,6-dianhydrohexitols and bisphenol A

“…Recently, several studies described the use of dianhydrohexitol diols as building blocks for numerous oligomers, homopolymers, and copolymers. [8][9][10][11] Moreover, the synthesis of co-polyesters based on isosorbide and isomannide [12][13][14] and the polycondensation of co-polycarbonates of isosorbide have been reported. [15,16] However, to the best of our knowledge, no study has investigated the use of combinations of these diols to produce copolyethersulfones.…”

Synthesis and characterization of novel biosourced building blocks from isosorbide

“…[1] 1,4:3,6-dianhydrohexitols (DAH), [2] three isomers of high importance in this context, were widely used as monomers and building blocks in polymer chemistry. [3][4][5][6] More specifically, isosorbide (Is), the most produced monomer on industrial scale, was extensively investigated but suffered from a lack of reactivity on its hydroxyl functions [7] Therefore in order to be used in commercial polymers, more reactive 1,4:3,6-dianhydrohexitols derivatives were needed. In this field, several interesting works dealt with their transformation into amines, [8,9] acids, [10] or extended primary alcohols.…”