Cyclic and Noncyclic Polycarbonates of Isosorbide (1,4:3,6-Dianhydro-<scp>d</scp>-glucitol)

Chatti, Saber; Schwarz, Gert; Kricheldorf, Hans R.

doi:10.1021/ma0606051

Cited by 111 publications

(94 citation statements)

References 16 publications

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“…1). In fact, isosorbide has been extensively employed for the preparation of polyesters, polyurethanes and polycarbonates [72–81]. Isosorbide is also considered as a possible candidate to replace petroleum-derived and toxic bisphenol A in polycarbonate preparation.…”

Section: Reviewmentioning

confidence: 99%

Isosorbide and dimethyl carbonate: a green match

Aricò

Tundo

2016

Beilstein J. Org. Chem.

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In this review the reactivity of the bio-based platform compounds D-sorbitol and isosorbide with green reagents and solvent dimethyl carbonate (DMC) is reported. Dehydration of D-sorbitol via DMC in the presence of catalytic amounts of base is an efficient and viable process for the preparation of the industrially relevant anhydro sugar isosorbide. This procedure is “chlorine-free”, one-pot, environmental friendly and high yielding. The reactivity of isosorbide with DMC is equally interesting as it can lead to the formation of dicarboxymethyl isosorbide, a potential monomer for isosorbide-based polycarbonate, and dimethyl isosorbide, a high boiling green solvent. The peculiar reactivity of isosorbide and the non-toxic properties of DMC represent indeed a green match leading to several industrial appealing potential applications.

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Section: Reviewmentioning

confidence: 99%

Isosorbide and dimethyl carbonate: a green match

Aricò

Tundo

2016

Beilstein J. Org. Chem.

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“…Radiation‐curable powder coating resins were prepared by ring‐opening polymerization of 2,2‐dimethyl‐1,3‐trimethylene carbonate, followed by end‐capping with methacrylate moieties 18. Different (co)polycarbonates based on the DAHs were also described in literature, but so far their functionalities and subsequent coating application were not elaborated upon 19–30…”

Section: Introductionmentioning

confidence: 99%

Chemistry, functionality, and coating performance of biobased copolycarbonates from 1,4:3,6‐dianhydrohexitols

Noordover

Haveman

Duchateau

et al. 2011

J of Applied Polymer Sci

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Biobased polycarbonates were synthesized from 1,4:3,6-dianhydro-D-glucitol, 1,4:3,6-dianhydro-L-iditol, and 1,4:3,6-dianhydro-D-mannitol as the principal diols, using different types of carbonyl sources. The (co)polycarbonates resulting from polycondensation reactions in solution using triphosgene consisted of several types of polymer chains with respect to chain topology (e.g., linear or cyclic chains) and end-group structure (e.g., hydroxyl, chloroformate or alkyl chloride end-groups). The introduction of flexible comonomers seemed to increase the amount of cyclic structures in the product mixtures. The melt polymerization of diphenyl carbonate with 1,4:3,6-dianhydrohexitols required high reaction temperatures and led to almost exclusively hydroxy-functional poly(1,4:3,6-dianhydrohexitol carbonate)s. Copolymerizing the 1,4:3,6-dianhydrohexitols with 1,3-propanediol and diphenyl carbonate at high temperature resulted in the partial loss of 1,3-propanediol. On the other hand, by melt polycondensation of 1,4:3,6-dianhydrohexitol-based bis(phenyl carbonate) monomers in combination with primary diols and/or triols, the insertion of the primary alcohols could be achieved in a more controlled way. OH-functional materials were prepared, having suitable molecular weights, T g values, thermal stability, and melt viscosity profiles for (powder) coating applications. These functional biobased (co)polycarbonates were cured with polyisocyanate curing agents, resulting in colorless to pale yellow transparent, glossy coatings with good mechanical performance and solvent resistance.

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“…Based on polystyrene calibration, the chromatogram shows traces of monomer. Such polydipersities were found for products composed of linear polycondensates and large fractions of cycles (58,59). Only 1,8-diamino-p-menthanediamine, 1l, failed to polymerize with bis-ketal diethyl galactarate.…”

Section: Diamine Structure Influenced the Formation Of Cyclic/linear mentioning

confidence: 88%

Synthesis and Characterization of Complex Mixtures Consisting of Cyclic and Linear Polyamides from EthylBis-Ketal Galactarates

Rosu

Cueto

Laine

et al. 2013

Journal of Macromolecular Science, Part A

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Bis-ketal-protected diethyl galactarate was condensed with different diamines to prepare sugar-based polyamides. Ketal-protected polyamides, which are soluble in organic solvents, were deprotected with 90% trifluoroacetic acid to yield water insoluble materials. FTIR, NMR, GPC, MALDI-TOF, ESI and TGA techniques were used to characterize the structure and the properties of these biodegradable materials.D-galactaric acid-based polyamides are complex mixtures of cyclic and linear structures. High molecular weight linear polymer formation was limited by competitive cyclization reactions. The percentage of cyclization was highly dependent on the nature of the diamine used. Polycondensation with linear aliphatic diamines favored the formation of macrocycles, identified by MALDI-TOF and ESI.

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Cyclic and Noncyclic Polycarbonates of Isosorbide (1,4:3,6-Dianhydro-d-glucitol)

Cited by 111 publications

References 16 publications

Isosorbide and dimethyl carbonate: a green match

Isosorbide and dimethyl carbonate: a green match

Chemistry, functionality, and coating performance of biobased copolycarbonates from 1,4:3,6‐dianhydrohexitols

Synthesis and Characterization of Complex Mixtures Consisting of Cyclic and Linear Polyamides from EthylBis-Ketal Galactarates

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