Polymers from renewable 1,4:3,6-dianhydrohexitols (isosorbide, isomannide and isoidide): A review

Fenouillot, Françoise; Rousseau, Alain; Colomines, Gaël; Saint‐Loup, René; Pascault, Jean‐Pierre

doi:10.1016/j.progpolymsci.2009.10.001

Cited by 660 publications

(703 citation statements)

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“…Those gentle conditions were selected considering an efficient removal of the methanol formed during the prepolymerization step and to favor the formation of products but taking into account the high volatility of the isohexides and 1,3-PD. 15 All sugar-based polyesters were obtained as honey-like materials, except for entry g which resulted in a fine white powder. The recorded yields were ranging from 20 to 72% after purification by precipitating the crude product in cold methanol.…”

Section: Enzymatic Synthesis Of the Sorbitol-and Isohexide-based Polymentioning

confidence: 99%

“…It has already been reported that melt polycondensation provides some limitations regarding the incorporation of unmodified isohexides due to distillation occurring during reaction. 15 A successful attempt to enzymatically polymerize the two bulky monomers, viz. IM and IIDMC, to obtain fully isohexide-based polyesters was achieved.…”

Section: Enzymatic Synthesis Of the Sorbitol-and Isohexide-based Polymentioning

confidence: 99%

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Isohexide and Sorbitol-Derived, Enzymatically Synthesized Renewable Polyesters with Enhanced T_g

et al. 2016

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Sugar-based polyesters derived from sorbitol and isohexides were obtained via solvent-free enzymatic catalysis. Pendant hydroxyl groups, coming from the sorbitol units, were present along the polyester backbone, whereas the two isohexides, namely, isomannide and isoidide dimethyl ester monomers, were selected to introduce rigidity into the polyester chains. The feasibility of incorporating isomannide as a diol compared to the isoidide dimethyl ester as acyl-donor via lipase-catalyzed polycondensation was investigated. The presence of bicyclic units resulted in enhanced T g with respect to the parent sorbitol-containing polyester lacking isohexides. The different capability of the two isohexides to boost the thermal properties confirmed the more flexible character provided by the isoidide diester derivative. Solvent-borne coatings were prepared by cross-linking the sugar-based polyester polyols with polyisocyanates. The increased rigidity of the obtained sugar-based polyester polyols led to an enhancement in hardness of the resulting coatings.

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Section: Enzymatic Synthesis Of the Sorbitol-and Isohexide-based Polymentioning

confidence: 99%

Section: Enzymatic Synthesis Of the Sorbitol-and Isohexide-based Polymentioning

confidence: 99%

Isohexide and Sorbitol-Derived, Enzymatically Synthesized Renewable Polyesters with Enhanced T_g

et al. 2016

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“…6,7 Among the wide diversity of sugar-derived monomers that have been recently explored, 1,4:3,6-dianhydrohexitols have drawn particular attention for the synthesis of linear polycondensates. 8,9 In these hexitols, the four exceeding hydroxyl groups are blocked by intramolecular etherification leading to a bicyclic structure with the secondary 2-and 5-hydroxyl groups standing free for reaction. The interest for monomers having a cyclic structure arises from their capacity for adding stiffness to the polymer chain with the subsequent increasing in T g .…”

Section: ' Introductionmentioning

confidence: 99%

Carbohydrate-Based Polyesters Made from Bicyclic Acetalized Galactaric Acid

et al. 2011

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The dimethyl ester of 2,3:4,5-di-O-methylene-galactaric acid (Galx) was made to react in the melt with 1,n-alkanediols HO(CH 2 ) n OH containing even numbers of methylenes (n from 6 to 12) to produce linear polycyclic polyesters. Two sets of poly(alkylene 2,3:4,5-di-O-methylenegalactarate) polyesters (PE-nGalx) with weight-average molecular weights in the ∼5000À10000 and ∼35000À45000 ranges were obtained using TBT and DBTO catalysts, respectively. For comparative purposes a set of poly(alkylene adipate) polyesters (PE-nAd) was also synthesized with molecular weights in the higher range using a similar procedure. The thermal stability of PE-nGalx was greater than that of PE-nAd although it notably decayed as molecular weight decreased. The replacement of Ad by Galx in the polyesters caused increases in T g of up to 70 °C, and almost doubled the tensile mechanical parameters. All PE-nGalx were semicrystalline but only those made from 1,12-dodecanediol were able to crystallize from the melt with a crystallization rate that diminished as the molecular weight increased. In general, the galactarate containing polyesters displayed higher solubility and wettability than polyadipates, they hydrolyzed faster and exhibited comparable sensitivity to the action of lipases. ' NOTE ADDED AFTER ASAP PUBLICATIONThis article posted ASAP on May 25, 2011. It was discovered that the bicyclic acetal was not 2,4:3,5 as first formulated, but rather 2,3:4,5. This change affects the abstract, paragraph 3 in the Introduction, paragraphs 1, 3, 4, 5, 6, 7 in the Experimental Section, paragraphs 1, 5, 12 in the Results and Discussion, and the Conclusions paragraph. Other changes include the Table of Contents graphic, Figures 1, 2, 3, 11, 12, and the Supporting Information file. The corrected version posted on June 23, 2011.

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“…Those consisting of diols of middle carbon-chain length (C5 -C8) are used as soft segments having low Tg, while those consisting of alicyclic building blocks can be applied as hard segments. [5][6][7][8][9][10] The commercially available poly-(hexamethylene carbonate) (PHMC) diol and poly-(hexamethylene/ pentamethylene carbonate) (PHPC) diol, having low molecular weight and bis-hydroxyl terminals, are used as soft segments of polyurethane. [11][12][13] Recently their environmental friendliness is highlighted because they are synthesized from ethylene carbonate (EC) manufactured by the use of carbon dioxide as feedstock.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Chain-Extended Poly(hexamethylene/pentamethylene carbonate)s and Their Block Copolymerization with Poly-L-lactide into Partly Biobased Thermoplastic Elastomers

et al. 2015

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Polymers from renewable 1,4:3,6-dianhydrohexitols (isosorbide, isomannide and isoidide): A review

Cited by 660 publications

References 91 publications

Isohexide and Sorbitol-Derived, Enzymatically Synthesized Renewable Polyesters with Enhanced T_g

Isohexide and Sorbitol-Derived, Enzymatically Synthesized Renewable Polyesters with Enhanced T_g

Carbohydrate-Based Polyesters Made from Bicyclic Acetalized Galactaric Acid

Preparation of Chain-Extended Poly(hexamethylene/pentamethylene carbonate)s and Their Block Copolymerization with Poly-L-lactide into Partly Biobased Thermoplastic Elastomers

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Polymers from renewable 1,4:3,6-dianhydrohexitols (isosorbide, isomannide and isoidide): A review

Cited by 660 publications

References 91 publications

Isohexide and Sorbitol-Derived, Enzymatically Synthesized Renewable Polyesters with Enhanced Tg

Isohexide and Sorbitol-Derived, Enzymatically Synthesized Renewable Polyesters with Enhanced Tg

Carbohydrate-Based Polyesters Made from Bicyclic Acetalized Galactaric Acid

Preparation of Chain-Extended Poly(hexamethylene/pentamethylene carbonate)s and Their Block Copolymerization with Poly-L-lactide into Partly Biobased Thermoplastic Elastomers

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Product

Resources

About

Isohexide and Sorbitol-Derived, Enzymatically Synthesized Renewable Polyesters with Enhanced T_g

Isohexide and Sorbitol-Derived, Enzymatically Synthesized Renewable Polyesters with Enhanced T_g