Low Molecular Weight Oligomers of Poly(alkylene succinate) Polyesters as Plasticizers in Poly(vinyl alcohol) Based Pharmaceutical Applications

Palamidi, Artemis; Kapourani, Afroditi; Christodoulou, Evi; Klonos, Panagiotis Α.; Kontogiannopoulos, Konstantinos N.; Kyritsis, Apostolos; Bikiaris, Dimitrios N.; Barmpalexis, Panagiotis

doi:10.3390/polym13010146

Cited by 13 publications

(14 citation statements)

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“…If k takes values above 1, then strong interactions between the blend components are taking place [ 38 , 39 ]. It is important to note (before proceeding with the analysis of the results) that the miscibility of the two components and the presence of a single T g for the two components (both are important prerequisites needed in order to use the Fox and GT models) were verified in a previous study [ 31 ]. Figure 5 shows the experimentally determined T g values along with the theoretical predictions derived from either the Fox or the GT approach for the neat PVA-PPSu matrices.…”

Section: Resultsmentioning

confidence: 99%

“…The preparation of the plasticizer (i.e., PPSu, Figure 1 ) was made via a two-stage melt polycondensation method (esterification and polycondensation) in a glass batch reactor based on a previously published methodology [ 31 ]. Briefly, accurately weighted amounts of succinic acid and diol (at a molar ratio of 1/1.1) were placed into a round bottom flask, along with the catalyst Sb 2 O 3 (400 ppm relative to succinic acid).…”

Section: Methodsmentioning

confidence: 99%

“…In these cases, i.e., when a plasticizer is added, a large reduction in frictional forces between the polymer chains is responsible for the lowering of the extrusion temperature, improving melt flow during processing (such as in the case of hot-melt extrusion) and improving the characteristics of the final resulting product (for example a filament) by reducing its brittleness [ 29 , 30 ]. Within the same concept, a recent publication has evaluated the use of poly(alkylene succinate)-based oligomers as PVA plasticizers suitable for fusion-based pharmaceutical applications [ 31 ]. Results in this study showed that the utilization of low molecular weight (MW) poly(propylene succinate) (PPSu) was able to reduce the processing temperature of PVA and improve its melt flow properties (estimated via melt flow index measurement) without affecting its thermal decomposition.…”

Section: Introductionmentioning

confidence: 99%

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Drug Amorphous Solid Dispersions Based on Poly(vinyl Alcohol): Evaluating the Effect of Poly(propylene Succinate) as Plasticizer

et al. 2021

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Although significant actions have been taken towards the utilization of poly(vinyl alcohol) (PVA) in the preparation of drug amorphous solid dispersions (ASDs) using fusion-based techniques (such as melt-quench cooling and hot-melt extrusion), several drawbacks regarding its rather high melting temperature and its thermal degradation profile make the use of the polymer extremely challenging. This is especially important when the active pharmaceutical ingredient (API) has a lower melting temperature (than PVA) or when it is thermally labile. In this vein, a previous study showed that newly synthesized polyester-based plasticizers may improve the processability and the thermal properties of PVA. However, the effects of such polyester-based plasticizers on the drug’s physicochemical and pharmaco-technical properties are yet unknown. Hence, the aim of the present study is to extend our previous findings and evaluate the use of poly(propylene succinate) (PPSu, i.e., the most promising plasticizer in regard to PVA) in the preparation of drug-loaded PVA-based ASDs. Dronedarone (DRN), a poorly water-soluble API, was selected as a model drug, and drug ASDs (using either neat PVA or PVA-PPSu) were prepared using the melt-mixing/quench cooling approach at low melting temperatures (i.e., 170 °C). DSC and pXRD analysis showed that a portion of the API remained crystalline in the ASDs prepared only with the use of neat PVA, while the samples having PPSu as a plasticizer were completely amorphous. Further evaluation with ATR-FTIR spectroscopy revealed the formation of significant intermolecular interactions between the API and the PVA-PPSu matrix, which could explain the system’s physical stability during storage. Finally, dissolution studies, conducted under nonsink conditions, revealed that the use of PVA-PPSu is able to maintain DRN’s sustained supersaturation for up to 8 h.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Drug Amorphous Solid Dispersions Based on Poly(vinyl Alcohol): Evaluating the Effect of Poly(propylene Succinate) as Plasticizer

et al. 2021

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“…In general the mentioned approaches are particularly useful for different biocompatible polymers as host materials for drug delivery systems [ 29 , 30 ], considering both compatibility of the polymer with drug molecules as well as influence of solvent on the mentioned colloidal systems stability. Recently, the mentioned parameters were used to study PES oligomers blends with PVA polymer in both room temperature (25 °C) and melt state (200 °C) by both modified Hoftyzer–van Krevelen and molecular modeling (estimation of total solubility parameter) approaches, respectively [ 31 ].…”

Section: Introductionmentioning

confidence: 99%

“…The study aims to prepare PES with molecular mass tailored solubility properties by catalyst-free direct condensation polymerization process to use it for potential biomedical applications, which may include, e.g., biocompatible plasticizers for high molecular weight polymers toward biomedical applications [ 30 ] as well as building blocks for self-assembled nanocarriers [ 31 ]. The successful polymerization was confirmed by FTIR, while the molecular mass of the polyester obtained was determined by 1 H NMR spectroscopy, gel permeation chromatography (GPC) and liquid chromatography–mass spectrometry (LC-MS) measurements.…”

Section: Introductionmentioning

confidence: 99%

The Effect of Molecular Weight on the Solubility Properties of Biocompatible Poly(ethylene succinate) Polyester

et al. 2021

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Poly(ethylene succinate) (PES) is one of the most promising biodegradable and biocompatible polyesters and is widely used in different biomedical applications. However, little information is available on its solubility and precipitation properties, despite that these solution behavior properties affect its applicability. In order to systematically study these effects, biodegradable and biocompatible poly(ethylene succinate) (PES) was synthesized using ethylene glycol and succinic acid monomers with an equimolar ratio. Despite the optimized reaction temperature (T = 185 °C) of the direct condensation polymerization, relatively low molecular mass values were achieved without using a catalyst, and the Mn was adjustable with the reaction time (40–100 min) in the range of ~850 and ~1300 Da. The obtained crude products were purified by precipitation from THF (“good” solvent) with excess of methanol (“bad” solvent). The solvents for PES oligomers purification were chosen according to the calculated values of solubility parameters by different approaches (Fedors, Hoy and Hoftyzer-van Krevelen). The theta-solvent composition of the PES solution was 0.3 v/v% water and 0.7 v/v% DMSO in this binary mixture. These measurements were also allowed to determine important parameters such as the coefficients A (=0.67) and B (=3.69 × 104) from the Schultz equation, or the Kη (=8.22 × 10−2) and α (=0.52) constants from the Kuhn–Mark–Houwink equation. Hopefully, the prepared PES with different molecular weights is a promising candidate for biomedical applications and the reported data and constants are useful for other researchers who work with this promising polyester.

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Coordinatively Stiffen and Toughen Hydrogels with Adaptable Crystal‐Domain Cross‐Linking

Qiao

Qiu

2023

Advanced Materials

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Conventional hydrogels usually suffer from the inherent conflict between stiffness and toughness, severely hampering their applications as load‐bearing materials. Herein, an adaptable crystal‐domain cross‐linking design is reported to overcome this inherent trade‐off for hydrogels by taking full advantage of both deformation‐resisting and energy‐dissipating capacities of cross‐linking points. Through solvent exchange to homogenize the polymer network, followed by salting out to foster crystallization, a class of sal‐exogels with high number densities of uniform crystalline domains embedded in homogeneous networks is constructed. During the deformation, those adaptive crystalline domains initially survive to arrest deformation, while later gradually disentangle to efficiently dissipate energy, crucial to the realization of the desirable compatibility between stiffness and toughness. The resultant sal‐exogel achieves coordinatively enhanced stiffness (52.3 ± 2.7 MPa) and toughness (120.7 ± 11.7 kJ m−2), reconciling the challenging trade‐off between them. This finding provides a practical and universal route to design stiff and tough hydrogels and has a profound impact on many applications requiring hydrogels with such combined mechanical properties.

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Low Molecular Weight Oligomers of Poly(alkylene succinate) Polyesters as Plasticizers in Poly(vinyl alcohol) Based Pharmaceutical Applications

Cited by 13 publications

References 52 publications

Drug Amorphous Solid Dispersions Based on Poly(vinyl Alcohol): Evaluating the Effect of Poly(propylene Succinate) as Plasticizer

Drug Amorphous Solid Dispersions Based on Poly(vinyl Alcohol): Evaluating the Effect of Poly(propylene Succinate) as Plasticizer

The Effect of Molecular Weight on the Solubility Properties of Biocompatible Poly(ethylene succinate) Polyester

Coordinatively Stiffen and Toughen Hydrogels with Adaptable Crystal‐Domain Cross‐Linking

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