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Keywords = caprolactam

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13 pages, 3976 KiB  
Article
Influence of Hexylene Glycol Terephthalate Chain Segments on the Crystallization and Thermal Properties of Polyamide 6
by Zeyang Li, Qiang Ren, Shan Mei, Wei Liu, Guangyi Zhou and Baoning Zong
Polymers 2025, 17(12), 1687; https://doi.org/10.3390/polym17121687 - 17 Jun 2025
Viewed by 272
Abstract
In this study, a poly [ε-caprolactam-co-bis(2-hydroxyethyl) terephthalate] copolymer (P (CL-co-BHET)) was synthesized from para-terephthalic acid (PTA), ethylene glycol (EG), and caprolactam (CL). The crystallization behavior and thermal stability of the copolymer were thoroughly investigated. With the aid of molecular [...] Read more.
In this study, a poly [ε-caprolactam-co-bis(2-hydroxyethyl) terephthalate] copolymer (P (CL-co-BHET)) was synthesized from para-terephthalic acid (PTA), ethylene glycol (EG), and caprolactam (CL). The crystallization behavior and thermal stability of the copolymer were thoroughly investigated. With the aid of molecular simulation, this study investigated the variation in interchain hydrogen bonding in the copolymer, focusing on the direction and the number of hydrogen bonds. The results revealed a close relationship between the copolymer chain structure, the variation in interchain hydrogen bonding, and the crystallization behavior and thermal stability of the copolymer. The introduction of BHET segments disrupted the regularity of the PA6 backbone and hydrogen bonding, leading to a decrease in the melting point, crystallization temperature, and crystallinity of the copolymer. The thermal stability of the copolymers also decreased, and the crystallization form gradually shifted from the α-crystalline to the γ-crystalline phase. The findings of this study are significant for evaluating the crystallization behavior of polyester amides and for predicting and regulating the properties of polyesteramide polymers. Full article
(This article belongs to the Section Polymer Physics and Theory)
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18 pages, 3188 KiB  
Article
The Migration and Pollution Risk of Microplastics in Water, Soil, Sediments, and Aquatic Organisms in the Caohai Watershed, Southwest China
by Xu Wang, Xianliang Wu, Xingfu Wang, Pinhua Xia, Lan Zhang, Xianfei Huang and Zhenming Zhang
Water 2025, 17(8), 1168; https://doi.org/10.3390/w17081168 - 14 Apr 2025
Viewed by 670
Abstract
The migration and driving factors of microplastics (MPs), as an emerging pollutant, have been reported in plateau lakes. However, whether MPs can accumulate to an extreme degree in the local aquatic organisms of plateau lakes remains unclear. Therefore, the present study mainly aims [...] Read more.
The migration and driving factors of microplastics (MPs), as an emerging pollutant, have been reported in plateau lakes. However, whether MPs can accumulate to an extreme degree in the local aquatic organisms of plateau lakes remains unclear. Therefore, the present study mainly aims to investigate the MPs accumulated in tissues of grass carp as well as reveal their migration processes and driving factors in the Caohai watershed, a typical plateau lake in southwest China. Density flotation (saturated NaCl solution) and laser direct infrared imaging spectrometry were used to analyze the relative abundance and morphological characteristics of MPs, respectively. The results showed that the MPs’ abundance in soil, water, and sediments ranged from 1.20 × 103 to 1.87 × 104 n/kg, from 9 to 223 n/L, and from 5.00 × 102 to 1.02 × 104 n/kg, respectively. The contents and composition of MPs in forestland soils were more plentiful in comparison with cultivated land soils and marshy grassland soils. Polyethylene (PE), polyvinylchloride (PVC), PA from caprolactam (PA6), and PA from hexamethylene diamine and adipic acid (PA66) were detected in grass carp, and PE was detected in all organs of grass carp. MP concentrations in the stomach, intestines, tissue, skin, and gills of grass carp ranged from 54.94 to 178.59 mg/kg. MP pollution probably mainly originated from anthropogenic factors (road traffic, farming activities, the habits of residents scattered around the study area, etc.) due to the Caohai watershed’s considerable proximity to Weining city. In addition, wind, land runoff, rivers, and atmospheric deposition in the locality directly and indirectly promoted MP migration. Our results suggested that although there is moderate MP pollution in soil, water, sediment, and grass carp in comparison with other areas, it is necessary to pay attention to PE and PVC migration via the various environmental media and the risks associated with consuming the local grass carp. The local government can make several policies to reuse and recycle agricultural film to alleviate local PE and PVC pollution. Full article
(This article belongs to the Special Issue Research on Microplastic Pollution in Water and Soil Environment)
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17 pages, 4732 KiB  
Article
Preparation of a Macromolecular Flame Retardant with a Phosphine Oxide Structure and Its Application in Polyamide 6
by Ke Liu, Bohan Liang, Shujuan Zhang, Ruyi Li, Junming Dai and Wangyang Lu
Polymers 2025, 17(4), 475; https://doi.org/10.3390/polym17040475 - 11 Feb 2025
Viewed by 882
Abstract
In this study, a novel macromolecular flame retardant (MFR) with a phosphine oxide structure is successfully synthesized to improve the flame retardancy of polyamide 6 (PA6). Following this, the flame-retardant polyamide 6 (FR–PA6) is prepared via melt blending the MFR with PA6. Results [...] Read more.
In this study, a novel macromolecular flame retardant (MFR) with a phosphine oxide structure is successfully synthesized to improve the flame retardancy of polyamide 6 (PA6). Following this, the flame-retardant polyamide 6 (FR–PA6) is prepared via melt blending the MFR with PA6. Results indicate that the introduction of MFR has little effect on the melting and crystallization temperature of FR–PA6. While it slightly reduces the thermal stability of PA6, MFR significantly enhances its flame retardancy. The limiting oxygen index of FR–PA6 increases from 21.8% to 28.2%, and it successfully passes the UL-94 V-0 rating when it contains 0.5 wt% of phosphorus. Compared with pure PA6, the av-EHC of FR–PA6 is reduced by 32.2% and the SEA is increased by 66.7%. The MFR showed a flame-retardant mechanism in both the gas phase and the condensed phase. In the gas phase, the decomposition of MFR releases phosphorus-containing free radicals to interrupt the combustion chain reaction and reduces the concentration of the combustible caprolactam. In the condensed phase, the MFR promotes faster formation of melt droplets during combustion, taking heat away from the burning PA6 timely. Full article
(This article belongs to the Special Issue Flame-Retardant Polymer Composites II)
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28 pages, 3061 KiB  
Review
Soluplus®-Based Pharmaceutical Formulations: Recent Advances in Drug Delivery and Biomedical Applications
by Nerea Guembe-Michel, Paul Nguewa and Gustavo González-Gaitano
Int. J. Mol. Sci. 2025, 26(4), 1499; https://doi.org/10.3390/ijms26041499 - 11 Feb 2025
Viewed by 3080
Abstract
Poor water solubility remains a significant challenge in the pharmaceutical industry that limits the therapeutic efficacy and bioavailability of many active pharmaceuticals. Soluplus® (SLP), an amphiphilic graft copolymer made of polyethylene glycol, polyvinyl caprolactam, and polyvinyl acetate, has been gaining interest in [...] Read more.
Poor water solubility remains a significant challenge in the pharmaceutical industry that limits the therapeutic efficacy and bioavailability of many active pharmaceuticals. Soluplus® (SLP), an amphiphilic graft copolymer made of polyethylene glycol, polyvinyl caprolactam, and polyvinyl acetate, has been gaining interest in recent years as it addresses these limitations by acting as a versatile carrier. Its ability to form stable amorphous dispersions and enhance drug solubility, as well as its physicochemical properties, support its role as a key excipient in advanced drug delivery systems. Recent investigations have demonstrated the adaptability of SLP in addressing drug delivery requirements, offering controlled release, improved targeting, and superior therapeutic outcomes. This review examines some key formulation methods that make use of SLP, including hot-melt extrusion, spray drying, electrospinning, drug–polymer layering, and capsule and tablet formulations, highlighting the capacity of SLP to overcome formulation challenges. Biomedical applications of SLP have also been explored, with a focus on its role in improving the delivery of antitumoral, anti-inflammatory, antimicrobial, and antiparasitic drugs. Full article
(This article belongs to the Section Macromolecules)
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12 pages, 1677 KiB  
Article
Enhanced Drug Skin Permeation by Azone-Mimicking Ionic Liquids: Effects of Fatty Acids Forming Ionic Liquids
by Takeshi Oshizaka, Shunsuke Kodera, Rika Kawakubo, Issei Takeuchi, Kenji Mori and Kenji Sugibayashi
Pharmaceutics 2025, 17(1), 41; https://doi.org/10.3390/pharmaceutics17010041 - 30 Dec 2024
Cited by 1 | Viewed by 1298
Abstract
Background/Objectives: Laurocapram (Azone) attracted attention 40 years ago as a compound with the highest skin-penetration-enhancing effect at that time; however, its development was shelved due to strong skin irritation. We had already prepared and tested an ante-enhancer (IL-Azone), an ionic liquid (IL) [...] Read more.
Background/Objectives: Laurocapram (Azone) attracted attention 40 years ago as a compound with the highest skin-penetration-enhancing effect at that time; however, its development was shelved due to strong skin irritation. We had already prepared and tested an ante-enhancer (IL-Azone), an ionic liquid (IL) with a similar structure to Azone, consisting of ε-caprolactam and myristic acid, as an enhancer candidate that maintains the high skin-penetration-enhancing effect of Azone with low skin irritation. In the present study, fatty acids with different carbon numbers (caprylic acid: C8, capric acid: C10, lauric acid: C12, myristic acid: C14, and oleic acid: C18:1) were selected and used with ε-caprolactam to prepare various IL-Azones in the search for a more effective IL-Azone. Methods: Excised porcine skin was pretreated with each IL-Azone to assess the in vitro skin permeability of antipyrine (ANP) as a model penetrant. In addition, 1,3-butanediol was selected for the skin permeation test to confirm whether the effect of IL-Azone was due to fatty acids and if this effect differed depending on the concentration of IL-Azone applied. Results: The results obtained showed that C12 IL-Azone exerted the highest skin-penetration-enhancing effect, which was higher than Azone. On the other hand, many of the IL-Azones tested had a lower skin-penetration-enhancing effect. Conclusions: These results suggest the potential of C12 IL-Azone as a strong and useful penetration enhancer. Full article
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24 pages, 19333 KiB  
Article
Development of Thermosensitive Hydrogels with Tailor-Made Geometries to Modulate Cell Harvesting of Non-Flat Cell Cultures
by Rubén García-Sobrino, Enrique Martínez-Campos, Daniel Marcos-Ríos, Zenen Zepeda-Rodríguez, Juan L. Valentín, Raúl Sanz-Horta, Marina León-Calero, Helmut Reinecke, Carlos Elvira, Alberto Gallardo and Juan Rodríguez-Hernández
Gels 2024, 10(12), 802; https://doi.org/10.3390/gels10120802 - 6 Dec 2024
Cited by 1 | Viewed by 1206
Abstract
Considering the complexity in terms of design that characterizes the different tissues of the human body, it is necessary to study and develop more precise therapies. In this sense, this article presents the possibility of fabricating photocurable thermosensitive hydrogels with free geometry and [...] Read more.
Considering the complexity in terms of design that characterizes the different tissues of the human body, it is necessary to study and develop more precise therapies. In this sense, this article presents the possibility of fabricating photocurable thermosensitive hydrogels with free geometry and based on N-Vinyl Caprolactam (VCL) with the aim of modulating the adhesion of non-planar cell cultures. The fabrication process is based on the use as a mold of two-layer thick water-soluble polyvinyl alcohol (PVA) previously printed by Extrusion Material (MatEx). From this technology it has been possible to obtain hydrogels with different 3D geometries and different crosslinking percentages (2, 4 and 6 mol%). Studies have shown that networks reduce their thermosensitivity not only when the percentage of crosslinking in the formulation increases, but also when the thickness of the hydrogel obtained increases. Based on this reduction in thermosensitivity, the less crosslinked (2 mol%) hydrogels have been evaluated to carry out a novel direct application in which hydrogels with curved geometry have allowed cell adhesion and proliferation at 37 °C with the endothelial cell line C166-GFP; likewise, non-aggressive cell detachment was observed when the hydrogel temperature was reduced to values of 20 °C. Therefore, the present manuscript shows a novel application for the synthesis of free-form thermosensitive hydrogels that allows modulation of non-planar cell cultures. Full article
(This article belongs to the Special Issue Advances in Hydrogels for 3D Printing)
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13 pages, 3785 KiB  
Article
Preparation of an Antibacterial Branched Polyamide 6 via Hydrolytic Ring-Opening Co-Polymerization of ε-Caprolactam and Lysine Derivative
by Xiaoyu Mao, Wei Liu, Zeyang Li, Shan Mei and Baoning Zong
Polymers 2024, 16(14), 1997; https://doi.org/10.3390/polym16141997 - 12 Jul 2024
Cited by 1 | Viewed by 1409
Abstract
In this study, we successfully realized the hydrolytic ring-opening co-polymerization of ε-caprolactam (CPL) and lysine derivative. A novel antibacterial modified polyamide 6 with a branched structure was obtained after the quaternization of the co-polymers. The co-polymers exhibited a significant increase in zero shear [...] Read more.
In this study, we successfully realized the hydrolytic ring-opening co-polymerization of ε-caprolactam (CPL) and lysine derivative. A novel antibacterial modified polyamide 6 with a branched structure was obtained after the quaternization of the co-polymers. The co-polymers exhibited a significant increase in zero shear viscosity, melt index and storage modulus at the low frequency region. The quaternized co-polymers displayed thermal properties different from pure PA6 and good mechanical (tensile) properties. The antibacterial activity of the quaternized co-polymers depends on the quaternary ammonium groups’ incorporated content. At 6.2 mol% incorporation of quaternary ammonium groups, the strong antibacterial activity has been introduced to the co-polymers. As the quaternary ammonium groups approached 10.1 mol%, the antibacterial polymers demonstrated nearly complete killing of Staphylococcus aureus (Gram positive) and Escherichia coli (Gram negative). The above research results provided a new approach for the study of high-performance nylon. Full article
(This article belongs to the Special Issue Application and Characterization of Polymer Composites)
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19 pages, 3619 KiB  
Article
Development, Characterization, and Evaluation of Potential Systemic Toxicity of a Novel Oral Melatonin Formulation
by Catalina N. Cheaburu-Yilmaz, Kemal Atmaca, Onur Yilmaz and Hilmi Orhan
Pharmaceutics 2024, 16(7), 871; https://doi.org/10.3390/pharmaceutics16070871 - 28 Jun 2024
Cited by 6 | Viewed by 1743
Abstract
The need to create safe materials for biomedical and pharmaceutical applications has become a significant driving force for the development of new systems. Therefore, a chitosan-coated copolymer of itaconic acid, acrylic acid, and N-vinyl caprolactam (IT-AA-NVC) was prepared by radical polymerization and subsequent [...] Read more.
The need to create safe materials for biomedical and pharmaceutical applications has become a significant driving force for the development of new systems. Therefore, a chitosan-coated copolymer of itaconic acid, acrylic acid, and N-vinyl caprolactam (IT-AA-NVC) was prepared by radical polymerization and subsequent coating via nanoprecipitation to give a system capable of sustained delivery of melatonin. Although melatonin brings undoubted benefits to the human body, aspects of the optimal dose, route, and time of administration for the obtaining of suitable treatment outcomes remain under discussion. The entrapment of melatonin in biocompatible polymeric systems can prevent its oxidation, decrease its toxicity, and provide an increased half-life, resulting in an enhanced pharmacokinetic profile with improved patient compliance. The structures of the biopolymer and conjugate were proven by FTIR, thermal properties were tested by DSC, and the morphologies were followed by SEM. The loading efficiency and in vitro release profile were studied by means of HPLC, and a delayed release profile with an initial burst was obtained. The potential systemic toxicity of the formulation was studied in vivo; a mild hepatotoxicity was observed following administration of the melatonin-loaded formulation to mice, both by histopathology and blood clinical biochemistry. Histopathology showed a mild nephrotoxicity as well; however, kidney clinical biochemistry did not support this. Full article
(This article belongs to the Special Issue Advances in Polymeric Drug Delivery Systems, 2nd Edition)
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13 pages, 3729 KiB  
Article
Preparation of a Novel Branched Polyamide 6 (PA6) via Co-Polymerization of ε-Caprolactam and α-Amino-ε-Caprolactam
by Xiaoyu Mao, Wei Liu, Zeyang Li, Shan Mei and Baoning Zong
Polymers 2024, 16(12), 1719; https://doi.org/10.3390/polym16121719 - 16 Jun 2024
Cited by 1 | Viewed by 2659
Abstract
In this study, a novel branched polyamide 6 has been synthesized via the hydrolytic ring-opening co-polymerization of ε-caprolactam (CPL) and α-Amino-ε-caprolactam (ACL). The NMR characterization proves the existence of a branched chain structure. The rheological test determines that there is a remarkable increase [...] Read more.
In this study, a novel branched polyamide 6 has been synthesized via the hydrolytic ring-opening co-polymerization of ε-caprolactam (CPL) and α-Amino-ε-caprolactam (ACL). The NMR characterization proves the existence of a branched chain structure. The rheological test determines that there is a remarkable increase in the melt index (MFR), zero shear rate viscosity, and storage modulus in the low-frequency region. The shear-thinning phenomenon becomes more obvious. The thermal properties tested by differential scanning calorimetry (DSC) show that the melting point and crystallinity of co-polymers decrease with the incorporation of ACL. However, the crystal structure of the samples only exhibits a slight change. When the ACL content in the feed is 1 wt%, the tensile strength and fracture elongation rate of the co-polymers show a significant enhancement. Full article
(This article belongs to the Section Polymer Chemistry)
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15 pages, 7401 KiB  
Article
Formation of Microporous Poly Acrylonitrile-Co-Methyl Acrylate Membrane via Thermally Induced Phase Separation for Immiscible Oil/Water Separation
by Linli Tan, Yuqi Wang and Mingpu Li
Molecules 2024, 29(10), 2302; https://doi.org/10.3390/molecules29102302 - 14 May 2024
Viewed by 3340
Abstract
An interconnected sponge structure and porous surface poly (acrylonitrile-co-methyl acrylate) (P(AN-MA)) microfiltration membranes (MF) were fabricated via thermally induced phase separation (TIPS) by using caprolactam (CPL), and acetamide (AC) as the mixed diluent. When the ternary system was composed of 15 wt.% P(AN-MA), [...] Read more.
An interconnected sponge structure and porous surface poly (acrylonitrile-co-methyl acrylate) (P(AN-MA)) microfiltration membranes (MF) were fabricated via thermally induced phase separation (TIPS) by using caprolactam (CPL), and acetamide (AC) as the mixed diluent. When the ternary system was composed of 15 wt.% P(AN-MA), 90 wt.% CPL, and 10 wt.% AC and formed in a 25 °C air bath, the membrane exhibited the highest water flux of 8107 L/m2·h. The P(AN-MA) membrane contained hydrophobic groups (-COOCH3) and hydrophilic groups (-CN), leading it to exhibit oleophobic properties underwater and hydrophobic properties in oil. The membrane demonstrates efficient separation of immiscible oil/water mixtures. The pure water flux of the petroleum ether/water mixture measured 870 L/m2·h, and the pure oil flux of the petroleum tetrachloride/water mixture measured 1230 L/m2·h under the influence of gravity. Additionally, the recovery efficiency of diluents through recrystallization was 85.3%, significantly reducing potential pollution and production costs. Full article
(This article belongs to the Special Issue Advances in Membrane Preparation and Applications in Green Chemistry)
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15 pages, 5661 KiB  
Article
Synergistic Effect of PBz/Epoxy/PCLA Composite Films with Improved Thermal Properties
by Thirukumaran Periyasamy, Shakila Parveen Asrafali, Seongcheol Kim and Jaewoong Lee
Sustainability 2024, 16(10), 3991; https://doi.org/10.3390/su16103991 - 10 May 2024
Cited by 1 | Viewed by 1458
Abstract
Polybenzoxazines (PBzs) are advanced forms of phenolic resins that possess many attractive properties, including thermally induced self-curing polymerization, which produces void-free polymer products without any by-product formation. They also possess a high Tg (glass transition temperature) and thermal stability, but the produced [...] Read more.
Polybenzoxazines (PBzs) are advanced forms of phenolic resins that possess many attractive properties, including thermally induced self-curing polymerization, which produces void-free polymer products without any by-product formation. They also possess a high Tg (glass transition temperature) and thermal stability, but the produced materials are brittle in nature, due to which the final form of their application is very difficult. Hence, in this paper, an attempt has been made to overcome the brittleness of PBz by blending it with epoxy and ε-caprolactam (CPLA) to produce free-standing PBz/Epoxy/PCLA (polycaprolactam) films. The curing process between the three components (i.e., Bzo, epoxy, and caprolactam) was monitored using differential scanning calorimetric (DSC) analysis. The results show that there is no appreciable shift in curing the exotherm observed, except a slight shift in the curing process. However, the heat liberated during the exotherm (ΔH) decreases drastically from 121 to 84 J/g, indicating that the content of benzoxazine is very important as it is involved in the polymerization process through oxazine ring-opening. The morphological studies analyzed using SEM and AFM analyses indicate that there was no observable phase separation up to 30 wt.% of CPLA loading, whereas a higher CPLA content of 50 wt.% causes agglomeration and leads to distinctive phase separation. Moreover, the thermal stability of the composite film, PBz/Epoxy/PCLA30, is also increased with a 10% degradation temperature, T10, of 438 °C, when compared with an PBz/Epoxy film. From the obtained results, it is evident that the formation of a composite film through the melt blending process could produce a tough and thermally stable film without sacrificing individual properties. Full article
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18 pages, 1036 KiB  
Article
Antimicrobial, Probiotic, and Immunomodulatory Potential of Cannabis sativa Extract and Delivery Systems
by Anna Stasiłowicz-Krzemień, Daria Szymanowska, Piotr Szulc and Judyta Cielecka-Piontek
Antibiotics 2024, 13(4), 369; https://doi.org/10.3390/antibiotics13040369 - 17 Apr 2024
Cited by 5 | Viewed by 3646
Abstract
The compounds present in hemp show multidirectional biological activity. It is related to the presence of secondary metabolites, mainly cannabinoids, terpenes, and flavonoids, and the synergy of their biological activity. The aim of this study was to assess the activity of the Henola [...] Read more.
The compounds present in hemp show multidirectional biological activity. It is related to the presence of secondary metabolites, mainly cannabinoids, terpenes, and flavonoids, and the synergy of their biological activity. The aim of this study was to assess the activity of the Henola Cannabis sativae extract and its combinations with selected carriers (polyvinyl caprolactam–polyvinyl acetate–polyethylene glycol graft copolymer, magnesium aluminometasilicate, and hydroxypropyl-β-cyclodextrin) in terms of antimicrobial, probiotic, and immunobiological effects. As a result of the conducted research, the antimicrobial activity of the extract was confirmed in relation to the following microorganisms: Clostridium difficile, Listeria monocytogenes, Enterococcus faecalis, Staphylococcus aureus, Staphylococcus pyrogenes, Escherichia coli, Klebsiella pneumoniae, Salmonella typhimurium, Pseudomonas aereuginosa, and Candida albicans (microorganism count was reduced from ~102 CFU mL−1 to <10 CFU mL−1 in most cases). Additionally, for the system with hydroxypropyl-β-cyclodextrin, a significant probiotic potential against bacterial strains was established for strains Lactobacillus acidophilus, Lactobacillus casei, Lactobacillus plantarum, Lactobacillus brevis, Lactobacillus rhamnosus, Lactobacillus reuteri, Pediococcus pentosaceus, Lactococcus lactis, Lactobacillus fermentum, and Streptococcus thermophilus (microorganism count was increased from ~102 to 104–107). In terms of immunomodulatory properties, it was determined that the tested extract and the systems caused changes in IL-6, IL-8, and TNF-α levels. Full article
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5 pages, 1296 KiB  
Short Note
2,3,5,6-Tetrafluoro-[N-(3-aminopropyl)-ε-caprolactam]-4-pyridine
by Chadron M. Friesen, Nathan J. Weeks and Scott T. Iacono
Molbank 2024, 2024(1), M1777; https://doi.org/10.3390/M1777 - 22 Feb 2024
Cited by 1 | Viewed by 1741
Abstract
The title compound was synthesized at a near-quantitative yield using the nucleophilic aromatic substitution of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with perfluoropyridine (PFP). The purity and structure were determined by NMR (1H, 13C, 19F), GC-EIMS, and single-crystal X-ray crystallography. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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11 pages, 2753 KiB  
Article
Poly Caprolactam Supported Hexaethylene Glycolic Imidazolium Ionic Liquid as a Heterogeneous Promoter for Nucleophilic Fluorination
by Mudumala Veeranarayana Reddy, Keun Heok Park and Dong Wook Kim
Molecules 2023, 28(18), 6747; https://doi.org/10.3390/molecules28186747 - 21 Sep 2023
Viewed by 1507
Abstract
Hexaethylene glycolic vinyl imidazolium (hexaEGVIM) was supported on N-vinyl caprolactam via covalent bonds through simple copolymerization to form poly caprolactam-supported hexaethylene glycol-substituted imidazolium salts (PCLS-hexaEGIM). The resulting heterogeneous PCLS-hexaEGIM promoter was active, selective, and stable for aliphatic nucleophilic substitution reactions using alkali [...] Read more.
Hexaethylene glycolic vinyl imidazolium (hexaEGVIM) was supported on N-vinyl caprolactam via covalent bonds through simple copolymerization to form poly caprolactam-supported hexaethylene glycol-substituted imidazolium salts (PCLS-hexaEGIM). The resulting heterogeneous PCLS-hexaEGIM promoter was active, selective, and stable for aliphatic nucleophilic substitution reactions using alkali metal salts. The alkali metal salts dramatically enhanced the reactivity of this heterogeneous catalyst with easily isolable higher product yields, reducing the formation of by-products. Therefore, nucleophilic fluorination and other substitution reactions can act as highly efficient catalysts in various sulfonyloxyalkanes and haloalkanes with regard to their corresponding fluorinated products. Full article
(This article belongs to the Special Issue Advances in Modern Fluorine Chemistry)
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24 pages, 2019 KiB  
Article
Co-Dispersion Delivery Systems with Solubilizing Carriers Improving the Solubility and Permeability of Cannabinoids (Cannabidiol, Cannabidiolic Acid, and Cannabichromene) from Cannabis sativa (Henola Variety) Inflorescences
by Anna Stasiłowicz-Krzemień, Piotr Szulc and Judyta Cielecka-Piontek
Pharmaceutics 2023, 15(9), 2280; https://doi.org/10.3390/pharmaceutics15092280 - 4 Sep 2023
Cited by 9 | Viewed by 3548
Abstract
Cannabinoids: cannabidiol (CBD), cannabidiolic acid (CBDA), and cannabichromene (CBC) are lipophilic compounds with limited water solubility, resulting in challenges related to their bioavailability and therapeutic efficacy upon oral administration. To overcome these limitations, we developed co-dispersion cannabinoid delivery systems with the biopolymer polyvinyl [...] Read more.
Cannabinoids: cannabidiol (CBD), cannabidiolic acid (CBDA), and cannabichromene (CBC) are lipophilic compounds with limited water solubility, resulting in challenges related to their bioavailability and therapeutic efficacy upon oral administration. To overcome these limitations, we developed co-dispersion cannabinoid delivery systems with the biopolymer polyvinyl caprolactam-polyvinyl acetate-polyethylene glycol (Soluplus) and magnesium aluminometasilicate (Neusilin US2) to improve solubility and permeability. Recognizing the potential therapeutic benefits arising from the entourage effect, we decided to work with an extract instead of isolated cannabinoids. Cannabis sativa inflorescences (Henola variety) with a confirming neuroprotective activity were subjected to dynamic supercritical CO2 (scCO2) extraction and next they were combined with carriers (1:1 mass ratio) to prepare the co-dispersion cannabinoid delivery systems (HiE). In vitro dissolution studies were conducted to evaluate the solubility of CBD, CBDA, and CBC in various media (pH 1.2, 6.8, fasted, and fed state simulated intestinal fluid). The HiE-Soluplus delivery systems consistently demonstrated the highest dissolution rate of cannabinoids. Additionally, HiE-Soluplus exhibited the highest permeability coefficients for cannabinoids in gastrointestinal tract conditions than it was during the permeability studies using model PAMPA GIT. All three cannabinoids exhibited promising blood-brain barrier (BBB) permeability (Papp higher than 4.0 × 10−6 cm/s), suggesting their potential to effectively cross into the central nervous system. The improved solubility and permeability of cannabinoids from the HiE-Soluplus delivery system hold promise for enhancement in their bioavailability. Full article
(This article belongs to the Special Issue Dosage Form Formulation Technologies for Improving Bioavailability)
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