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

Noordover, Baj Bart; Haveman, D Daniël; Duchateau, Robbert; Benthem, Ratm Rolf van; Koning, CE Cor

doi:10.1002/app.33660

Cited by 54 publications

(65 citation statements)

References 67 publications

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“…PCaG 20 BPA 80 C shows the highest T g value of 151.2°C which is higher than a commercial BPA PC (150°C) while PBPAC in our experiment shows similar T g value to the PCaGCs. 32 Therefore, we suggest the same reason that cyclic ketal linked by rigid norbornane ring induce stiffness leading to high glass transition temperature rather than independently linked by single C−C bond. 23 …”

Section: ■ Results and Discussionmentioning

confidence: 93%

High Thermal Stability of Bio-Based Polycarbonates Containing Cyclic Ketal Moieties

2015

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Bio-based polycarbonates containing cyclic ketal moieties were designed, and the bio-based diol monomer was synthesized by CQ with glycerol to improve their thermal properties and replace BPA in polymer industry. The molecular structure of the novel bio-based diol monomer 2,2:3,3-bis(4′-hydroxymethylethylenedioxy)-1,7,7-trimethylbicyclo[2.2.1]heptane (abbreviated as CaG) was analyzed by 1 H, 13 C, and 2D-COSY NMR techniques. GPC results show that CaG was reacted successfully and led to the high molecular weights for homopolycarbonate (M w = 18 652) abbreviated as PCaGC and for copolycarbonate (M w = 78 482) as PCaG 20 BPA 80 C. The high thermal stability (T d value above 350°C) and glass transition temperature (T g value from 128 to 151°C) of PCaGCs and PCaG x BPA y Cs were studied by TGA and DSC, respectively. Given the sufficient reactivity and high thermal stability, CaG is a promising renewable building block for applicable polymers.

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Section: ■ Results and Discussionmentioning

confidence: 93%

High Thermal Stability of Bio-Based Polycarbonates Containing Cyclic Ketal Moieties

2015

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“…In this view, the main issue that limits the exploitation of this compound is its lower acidity. To overcome this problem, polycarbonates incorporating an isosorbide moiety have been synthesized via a chlorine-based approach, i.e., employing phosgene or its derivatives [82–83]. …”

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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“…Due to poor solubility of the polyesters and cross-linkers at room temperature in those solvents, a proper dissolution and mixing of the components as well as the wet coating application had to be carried out at 80-90°C, which is above the melting temperature of the polyesters. The resulting film was then simultaneously dried and cured at 180°C under N 2 flow for 30 min [23].…”

Section: Preparation Of Solvent-borne Coatingsmentioning

confidence: 99%

Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights

Gustini

Noordover

Gehrels

et al. 2015

European Polymer Journal

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(2015). Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights. European Polymer Journal, 67, 459-475. DOI: 10.1016/j.eurpolymj.2014 General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights.• Users may download and print one copy of any publication from the public portal for the purpose of private study or research.• You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal ? Take down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. By using a combination of bio-based monomers (sorbitol, 1,10-decanediol and a range of dicarboxylic acids), a series of novel sorbitol-based polyesters was prepared by solvent-free enzymatic polycondensation using an immobilized form of Candida antarctica lipase B (Novozyme 435). The aim was to prepare linear polyesters with pendant, curable hydroxyl groups along the polymer backbone. To achieve this, the polyester molecular weight was controlled by tuning the reaction time, enzyme loading and reaction stoichiometry. Extensive molecular and thermal characterization was performed, showing that the obtained polyesters were semi-crystalline materials with a low T g . The presence of sorbitol in the polyesters was confirmed through a qualitative investigation using MALDI-ToF-MS. The quantification of the sorbitol content in the polymers was achieved by inverse-gated decoupling 13 C NMR spectroscopy, while 31 P NMR provided information regarding the selectivity of CALB for the primary vs. the secondary hydroxyl groups. Moreover, 31 P NMR and potentiometric titration were utilized for the quantitative determination of the amount of carboxylic groups and hydroxyl functional groups present in the polyesters. The obtained hydroxyl-functional polyesters had suitable properties to be applied as solvent-borne coatings in terms of their molecular weight, functionality and thermal characteristics. Cross-linked coatings were prepared using different conventional curing agents, including two renewable diisocyanates (ethyl ester L-lysine diisocyanate and dimer fatty acid-based diisocyanate). The resulting poly(ester urethane) coatings were tested in terms of solvent resistance, hardness and resistance against rapid deformation, showing the beneficial effect of the implemented sorbitol on network formation.

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

Cited by 54 publications

References 67 publications

High Thermal Stability of Bio-Based Polycarbonates Containing Cyclic Ketal Moieties

High Thermal Stability of Bio-Based Polycarbonates Containing Cyclic Ketal Moieties

Isosorbide and dimethyl carbonate: a green match

Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights

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