Reinvestigation of the ring-opening polymerization of ε-caprolactone with 1,8-diazacyclo[5.4.0]undec-7-ene organocatalyst in bulk

Chen, Yang; Zhang, Jie; Xiao, Wenkai; Chen, Anfu; Dong, Zhixian; Xu, Jinbao; Xu, Wenhua; Lei, Caihong

doi:10.1016/j.eurpolymj.2021.110861

Cited by 11 publications

(5 citation statements)

References 67 publications

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“…However, extended reaction times with DBU can sometimes lead to transesterification reactions. Moreover, DBU requires a cocatalyst to polymerize CL monomers, and the monomer conversions are relatively low [ 54 , 55 ]. In contrast, TBD and phosphazene bases display exceptional catalytic performance towards ROP conditions.…”

Section: Synthesis Of Poly(ε-caprolactone)smentioning

confidence: 99%

Recent Advances in Polycaprolactones for Anticancer Drug Delivery

Bhadran,

Shah,

Babanyinah

et al. 2023

Pharmaceutics

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Poly(ε-Caprolactone)s are biodegradable and biocompatible polyesters that have gained considerable attention for drug delivery applications due to their slow degradation and ease of functionalization. One of the significant advantages of polycaprolactone is its ability to attach various functionalities to its backbone, which is commonly accomplished through ring-opening polymerization (ROP) of functionalized caprolactone monomer. In this review, we aim to summarize some of the most recent advances in polycaprolactones and their potential application in drug delivery. We will discuss different types of polycaprolactone-based drug delivery systems and their behavior in response to different stimuli, their ability to target specific locations, morphology, as well as their drug loading and release capabilities.

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Section: Synthesis Of Poly(ε-caprolactone)smentioning

confidence: 99%

Recent Advances in Polycaprolactones for Anticancer Drug Delivery

Bhadran,

Shah,

Babanyinah

et al. 2023

Pharmaceutics

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“…8 PLLA and polylactones are industrially produced at high temperatures, 9−11 and organic solvents are used occasionally, 1 although polymerization in bulk is preferred for its economy and sustainability. 11 There has been deep concern with regard to the use of organic solvents because of their toxicity and negative environmental effects as many of them are volatile. 1,12 Similarly, tin metal catalysts approved by the FDA are typically used in PLLA and polylactone polymerization at high temperatures (above 120 °C), 10 architectures.…”

Section: Introductionmentioning

confidence: 99%

“…In addition to controlling its molecular weight, the degradation of PLLA can be tuned by modifying the aggregate structure, crystallinity, and external factors in the media, such as the pH or the use of enzymes . PLLA and polylactones are industrially produced at high temperatures, − and organic solvents are used occasionally, although polymerization in bulk is preferred for its economy and sustainability . There has been deep concern with regard to the use of organic solvents because of their toxicity and negative environmental effects as many of them are volatile. , Similarly, tin metal catalysts approved by the FDA are typically used in PLLA and polylactone polymerization at high temperatures (above 120 °C), offering an excellent control in designing complex architectures.…”

Section: Introductionmentioning

confidence: 99%

Low-Temperature and Solventless Ring-Opening Polymerization of Eutectic Mixtures of l-Lactide and Lactones for Biodegradable Polyesters

Castillo-Santillán

Maniar

Gutiérrez

et al. 2023

ACS Appl. Polym. Mater.

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Biodegradability is one of the key features for reducing the negative environmental impact of plastic waste disposal; therefore, designing biocompatible polymeric biomaterials with programmable life cycles is urgently needed. Herein, deep eutectic solvent monomers (DESm) composed of l-lactide and various lactones of different molecular weights were formulated to obtain polyesters at low temperatures with the aid of organocatalysts and under solventless conditions. The introduced DESm expand the range of eutectic mixtures capable of undergoing ring-opening polymerization (ROP) to include mixtures of l-lactide with δ-valerolactone and δ-hexalactone. Extending the toolbox for DESm preparation will allow for the design of polyesters with tailored molecular weight and crystallinity, which are conducive to programmable degradability. ROP of DESm carried out at low temperatures and under solventless conditions holds promise for a sustainable framework for preparing biodegradable polymers for biomedical applications.

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“…In this respect, phosphazenes such as 2-tert-butylimino-2-diethylamino-1,3-dimethylpe rhydro-1,3,2-diazaphosphorine (BEMP) and N -tert-butyl-N,N,N ,N ,N",N"-hexamethylph osphorimide triamide (P1-t-Bu) represent an interesting class of organic catalysts capable of efficiently initiating the ROP polymerization of lactide and lactones [34,[41][42][43][44][45]. Considering that most of the basic organic catalysts reported today suffer from low thermal stability and cannot be used under industrially relevant temperatures (~180 • C) [46,47], the high thermal stability of phosphazenes make them promising catalysts for the bulk ROP of lactide and lactones [43,48]. Another important feature of phosphazenes is the possibility to prepare a supported catalyst using polystyrene beads [49] or a porous polymeric aromatic framework [50].…”

Section: Introductionmentioning

confidence: 99%

Phosphazene Functionalized Silsesquioxane-Based Porous Polymer as Thermally Stable and Reusable Catalyst for Bulk Ring-Opening Polymerization of ε-Caprolactone

et al. 2023

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The bulk ring-opening polymerization (ROP) of ε-caprolactone using phosphazene-containing porous polymeric material (HPCP) has been studied at high reaction temperatures (130–150 °C). HPCP in conjunction with benzyl alcohol as an initiator induced the living ROP of ε-caprolactone, affording polyesters with a controlled molecular weight up to 6000 g mol−1 and moderate polydispersity (Ð~1.5) under optimized conditions ([BnOH]/[CL] = 50; HPCP: 0.63 mM; 150 °C). Poly(ε-caprolactone)s with higher molecular weight (up to Mn = 14,000 g mol−1, Ð~1.9) were obtained at a lower temperature, at 130 °C. Due to its high thermal and chemical stability, HPCP can be reused for at least three consecutive cycles without a significant decrease in the catalyst efficiency. The tentative mechanism of the HPCP-catalyzed ROP of ε-caprolactone, the key stage of which consists of the activation of the initiator through the basic sites of the catalyst, was proposed.

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Reinvestigation of the ring-opening polymerization of ε-caprolactone with 1,8-diazacyclo[5.4.0]undec-7-ene organocatalyst in bulk

Cited by 11 publications

References 67 publications

Recent Advances in Polycaprolactones for Anticancer Drug Delivery

Recent Advances in Polycaprolactones for Anticancer Drug Delivery

Low-Temperature and Solventless Ring-Opening Polymerization of Eutectic Mixtures of l-Lactide and Lactones for Biodegradable Polyesters

Phosphazene Functionalized Silsesquioxane-Based Porous Polymer as Thermally Stable and Reusable Catalyst for Bulk Ring-Opening Polymerization of ε-Caprolactone

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