Characterization of cyclic and non-cyclic poly-(ether-urethane)s bio-based sugar diols by a combination of MALDI-TOF and NMR

Beldi, M.; Medimagh, Raouf; Chatti, Saber; Marque, Sylvain R. A.; Prim, Damien; Loupy, André; Delolme, Frédéric

doi:10.1016/j.eurpolymj.2007.06.003

Cited by 56 publications

(40 citation statements)

References 33 publications

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“…Isosorbide is a drug medicine used as osmotic diuretics and blood-pressure-lowering drugs. Also, isosorbide has attracted a great deal of attention because poly (ethylene terephthalate) (PET) containing isosorbide has higher glass transition temperatures than pure PET [13,[20][21][22], broadening the applications of polyesters. Consequently, the cellulose valorization can be realized by conversion of cellulose to isosorbide or anhydrosorbitol.…”

Section: Introductionmentioning

confidence: 99%

One-pot conversion of cellulose to isosorbide using supported metal catalysts and ion-exchange resin

Yamaguchi

Sato

Mimura

et al. 2015

Catalysis Communications

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Section: Introductionmentioning

confidence: 99%

One-pot conversion of cellulose to isosorbide using supported metal catalysts and ion-exchange resin

Yamaguchi

Sato

Mimura

et al. 2015

Catalysis Communications

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“…Isosorbide is regarded as a promising monomer for polycondensation due to its attractive rigidity, chirality and non‐toxicity 4, 5. Isosorbide has been widely used for the synthesis of polyesters,6–8 polyurethanes,9–11 poly(ester‐ co ‐carbonate)s12, 13 and polycarbonates 14–19. As far as the polycarbonates are concerned, isosorbide is an excellent candidate to replace bisphenol A (BPA), which is derived from petroleum and could induce chronic toxicity 20.…”

Section: Introductionmentioning

confidence: 99%

A non‐phosgene process to homopolycarbonate and copolycarbonates of isosorbide using dimethyl carbonate: Synthesis, characterization, and properties

Zhu

et al. 2012

J. Polym. Sci. A Polym. Chem.

116

156

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Poly(isosorbide carbonate) (PIC) was synthesized by melt polycondensation of dimethyl carbonate (DMC) and isosorbide using lithium acetylacetonate (LiAcac) as the catalyst. The reaction conditions were optimized to achieve PIC with relatively high number‐average molecular weight (Mn) of 28,800 g/mol and isosorbide conversion of 95.2%. A series of poly(aliphatic diol‐co‐isosorbide carbonate)s (PAICs) were also synthesized by melt polycondensation of DMC with isosorbide and equimolar amounts of aliphatic diols (1,4‐butanediol, 1,5‐pentanediol, 1,6‐hexanediol, and 1,4‐cyclohexane dimethanol) in the presence of LiAcac and the TiO2/SiO2‐based catalyst (TSP‐44). PAICs with Mn values ranging from 18,700 to 34,400 g/mol and polydispersities between 1.64 and 1.69 were obtained. The 13C NMR analysis revealed the random microstructure of PAICs. The differential scanning calorimetry results demonstrated that all the PAICs were amorphous with a unique Tg ranging from 46 to 88 °C. The dynamic analysis results showed that the incorporation of linear or cyclohexane structure changed the dynamic mechanical properties of PIC drastically. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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“…For example, 1,4:3,6‐dianhydro‐ D ‐glucitol or isosorbide (IS) is easily and stereoselectively obtained through a two‐step sequence including D ‐glucose hydrogenation (available on starch) followed by sorbitol dehydration. By a similar process,1,4:3,6‐dianhydro‐ D ‐mannitol or isomannide (IM) is conveniently prepared from D ‐mannose . 1,4:3,6‐dianhydro‐ D ‐iditol or isoidide (ID) can be obtained by the epimerization of the endo hydroxyl group at carbon 5 in isosorbide (Fig.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic syntheses of unsaturated polyesters based on isosorbide and isomannide

Naves

Fernandes

Immich

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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The search for materials produced from renewable sources aiming at the substitution of petroleum‐based derivates is an area of intense investigation. In this work, the enzymatic copolymerization of isosorbide or isomannide with diethyl adipate and fractions of different unsaturated diesters (diethyl itaconate, diethyl fumarate, diethyl glutaconate, and diethyl hydromuconate) were examined using CAL‐B as catalyst. The polyesters prepared using one‐step syntheses were characterized by SEC, NMR, and MALDI‐TOF MS. In addition, syntheses with linear diols were carried out in bulk to evaluate the reactivity of cyclic diols in producing unsaturated polyesters using enzymatic catalysis, as well as to evaluate the occurrence of addition side reactions on the double bonds. Isosorbide and isomannide yielded unsaturated polymers with Mtrue¯normalw values in the order of 4,000‐16,000 when fumarate or glutaconate esters were added in 5 mol % ratio against adipate. In all cases MALDI‐TOF confirmed the presence of unsaturated units. Although these polyesters have unreacted double bonds they are prone to crosslinking and ready to further functionalization, like anchoring bioactive molecules. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3881–3891

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Characterization of cyclic and non-cyclic poly-(ether-urethane)s bio-based sugar diols by a combination of MALDI-TOF and NMR

Cited by 56 publications

References 33 publications

One-pot conversion of cellulose to isosorbide using supported metal catalysts and ion-exchange resin

One-pot conversion of cellulose to isosorbide using supported metal catalysts and ion-exchange resin

A non‐phosgene process to homopolycarbonate and copolycarbonates of isosorbide using dimethyl carbonate: Synthesis, characterization, and properties

Enzymatic syntheses of unsaturated polyesters based on isosorbide and isomannide

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