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Guanidine and Amidine Organocatalysts for Ring-Opening Polymerization of Cyclic Esters

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TLDR
In this article, the ring-opening polymerization (ROP) of cyclic esters such as lactide (LA), δ-valerolactone (VL), and e-caprolactone(CL) was achieved.
Abstract
1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD), N-methyl-TBD (MTBD), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are effective organocatalysts for the ring-opening polymerization (ROP) of cyclic esters such as lactide (LA), δ-valerolactone (VL), and e-caprolactone (CL). TBD is shown to polymerize LA, VL, and CL in a fast and controlled manner, whereas MTBD and DBU polymerized LA and addition of a thiourea cocatalyst led to the ROP of VL and CL being achieved. Each of the catalysts produced polymers displaying high end group fidelity, good correlation between theoretical and observed molecular weight, and linear relationships between conversion and molecular weight. The enhanced activity of TBD relative to MTBD and DBU is attributed to its bifunctionality, enabling the simultaneous activation of both the cyclic ester monomer and the alcohol group of the initiator/propagating species. Temperature-dependent NMR studies generated individual association constants for MTBD with benzyl alcohol and thiourea with VL. ...

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Citations
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Chemical recycling of poly(bisphenol A carbonate)

TL;DR: In this article, a review on the recycling of poly(bisphenol A carbonate) (polycarbonate or PC), a leading engineering plastic with high strength and transparent properties for application in electronics, containers, automobiles, safety, and optics, is presented.
Journal ArticleDOI

Concerning the ring-opening polymerization of lactide and cyclic esters by coordination metal catalysts

TL;DR: A summary of the reactions involved in the ring-opening polymerization (ROP) of lactide (LA) to give polylactides (PLAs) is presented along with competing reactions as mentioned in this paper.
Journal ArticleDOI

Polymerizing Base Sensitive Cyclic Carbonates Using Acid Catalysis

TL;DR: In this paper, a bifunctional activation pathway was calculated for cyclic carbonate polymerization and the use of acid catalysis was shown to be compatible with amide-containing monomers while promoting controlled polymerizations.
Journal ArticleDOI

Opportunities for organocatalysis in polymer synthesis via step-growth methods

TL;DR: In this paper, the authors highlight the recent advances in organocatalysis in step-growth polymerizations, including polyesters, polycarbonates, and polyurethanes.
Journal ArticleDOI

Polymers from sugars and CO2: synthesis and polymerization of a d-Mannose-based cyclic carbonate

TL;DR: In this paper, a six-membered cyclic carbonate derived from natural sugar d-mannose was prepared using CO2 as a C1 building block at room temperature and atmospheric pressure.
References
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Journal ArticleDOI

Controlled ring-opening polymerization of lactide and glycolide.

TL;DR: This work focuses on the characterization of the phytochemical components of Lactide ROP and their role in the regulation of cell reprograming.
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Polymerization of Lactide with Zinc and Magnesium β-Diiminate Complexes: Stereocontrol and Mechanism

TL;DR: The substituents on the beta-diiminate ligand exert a significant influence upon the course of the polymerizations, affecting both the degree of stereoselectivity and the rate of polymerization.
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A review of biodegradable polymers: uses, current developments in the synthesis and characterization of biodegradable polyesters, blends of biodegradable polymers and recent advances in biodegradation studies

TL;DR: A review of the uses of biodegradable polymers in terms of their relevance within current plastic waste management of packaging materials, biomedical applications and other uses is presented in this paper.
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Extension of the self-consistent spectrophotometric basicity scale in acetonitrile to a full span of 28 pKa units: unification of different basicity scales.

TL;DR: The earlier compiled self-consistent spectrophotometric basicity scale in acetonitrile (AN) was expanded to range from 3.8 to 32.0 pK(a) units, that is 28 orders of magnitude, and 54 new relative basicity measurements were carried out and 37 new compounds were introduced to the scale.
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Stereochemistry of Lactide Polymerization with Chiral Catalysts: New Opportunities for Stereocontrol Using Polymer Exchange Mechanisms

TL;DR: A polymer exchange mechanism is proposed to account for the PLA microstructures resulting from rac-4, which polymerizes meso-lactide to syndiotactic poly(lactic acid) (PLA) and heterotactic and isotactic stereoblock PLA, respectively.
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