Lipase-Catalyzed Polycondensations:  Effect of Substrates and Solvent on Chain Formation, Dispersity, and End-Group Structure

Mahapatro, Anil; Kalra, Bhanu; Kumar, and Ajay; Gross, Richard A.

doi:10.1021/bm0257208

Cited by 145 publications

(180 citation statements)

References 25 publications

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“…It should be noted that the molecular weight of entry c could not be improved further after 26 h of polymerization due to the high viscosity of the reaction mixture. The polymerizations performed with 1 wt% CALB [26] did not reach such a high molecular weight within the same reaction time. In addition, the measured PDI values are lower than for the reactions using 10 wt% of CALB, indicating that conversion was lower, as expected.…”

Section: Synthesis Of Poly(18-octanediol-co-sorbitol Adipate)mentioning

confidence: 90%

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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Section: Synthesis Of Poly(18-octanediol-co-sorbitol Adipate)mentioning

confidence: 90%

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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“…5,6,8 SCP of the activated x-hydroxyester with TCE in the presence of Novozyme 435 has not yet been extensively investigated, so its feasibility must be first validated. Our group selected 1 (Scheme 1) as a model system for enzyme-catalyzed condensation polymerization.…”

Section: Resultsmentioning

confidence: 99%

“…Biocatalytic approaches have been employed in the design and fabrication of various polyesters with different structures for increasing demands. 1,2 For example, Novozyme 435 (immobilized Candida antarctica lipase B) has been recognized widely as an effective and versatile biocatalyst in polyester synthesis via both ring-opening polymerization (ROP) of lactones (e.g., -caprolactone) 3,4 and polycondensation of either diacid (its derivatives)/diol combinations [5][6][7] or hydroxyacid (its derivatives); 4,8 furthermore, its scope has been further widened by the preparation of block copolymers 9,10 and hyperbranched copolymers. 11 However, the full exploitation of biocatalysis in polymer synthesis will require the development of mutually compatible chemo-and biocatalytic methods.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic synthesis of an AB‐type diblock copolymer combining enzymatic self‐condensation polymerization and atom transfer radical polymerization

Sha¹,

Li²,

Li³

et al. 2006

J. Polym. Sci. A Polym. Chem.

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“…The reaction temperature is usually up to 150°C [6,7]. For this condition many monomers are not suitable for the formation of linear polyesters, due to uncontrollable side reactions and formation of gel [8][9][10]. Typically linear unsaturated polyesters processed to a relatively low molecular weight then it is dissolved in a monomer such as styrene to form a viscous solution.…”

Section: Introductionmentioning

confidence: 99%

Fabrication and Characterization of Unsaturated Copolyesters Based on Diarylidenecyclohexanone

Abdelaty¹

2017

AJPST

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New series of unsaturated copolyesters based on diarylidenecyclohexanone, were synthesized by the interfacial polycondensation polymerization technique. Aldol condensation reaction in acid media was used for preparation of three kinds of monomers and investigated by FT IR and 1 H NMR. The copolymers have been synthetized by the polymerization of 2, 6-bis (4-hydrxybenzylidene) cyclohexanone I, 2, 6-bis (3-hydroxybezylidene) cyclohexanone II, or 2, 6-bis (4-hydroxy-3-methoxybenzylidene) cyclohexanone III with isophthaloyl, terphthaloyl, adipoyl, sebacoyl and azobenzene 4, 4-dicaroxyldichloride. The resulting copolyesters were characterized by FT-IR, 1 HNMR. The intrinsic viscosity of these copolyesters was used for the determination of the molecular weight. The thermal stabilities of the prepared copolyesters were evaluated thermogravimeteric analysis (TGA). Differential thermal analysis (DTA) was used for determination of glass temperatures. X-ray analysis showed that polymers have low degree of crystallinity. The morphological properties of some selected copolyesters were detected by SEM. The dielectric and electrical resistance, capacitance, inductance, demonstrating the insulator behaviour of copolymers.

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Lipase-Catalyzed Polycondensations: Effect of Substrates and Solvent on Chain Formation, Dispersity, and End-Group Structure

Cited by 145 publications

References 25 publications

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

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

Chemoenzymatic synthesis of an AB‐type diblock copolymer combining enzymatic self‐condensation polymerization and atom transfer radical polymerization

Fabrication and Characterization of Unsaturated Copolyesters Based on Diarylidenecyclohexanone

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