An Eco-Friendly Ultrasound-Assisted Synthesis of Novel Fluorinated Pyridinium Salts-Based Hydrazones and Antimicrobial and Antitumor Screening

The present work reports an efficient synthesis of fluorinated pyridinium salts-based hydrazones under both conventional and eco-friendly ultrasound procedures. The synthetic approach first involves the preparation of halogenated pyridinium salts through the condensation of isonicotinic acid hydrazide (1) with p-fluorobenzaldehyde (2) followed by the nucleophilic alkylation of the resulting N-(4-fluorobenzylidene)isonicotinohydrazide (3) with a different alkyl iodide. The iodide counteranion of 5–10 was subjected to an anion exchange metathesis reaction in the presence of an excess of the appropriate metal salts to afford a new series of fluorinated pyridinium salts tethering a hydrazone linkage 11–40. Ultrasound irradiation led to higher yields in considerably less time than the conventional methods. The newly synthesized ILs were well-characterized with FT-IR, ¹H NMR, ¹³C NMR, ¹¹B, ¹⁹F, ³¹P and mass spectral analyses. The ILs were also screened for their antimicrobial and antitumor activities. Within the series, the salts tethering fluorinated counter anions 11–13, 21–23, 31–33 and 36–38 were found to be more potent against all bacterial and fungal strains at MIC 4–8 µg/mL. The in vitro antiproliferative activity was also investigated against four tumor cell lines (human ductal breast epithelial tumor T47D, human breast adenocarcinoma MCF-7, human epithelial carcinoma HeLa and human epithelial colorectal adenocarcinoma Caco-2) using the MTT assay, which revealed that promising antitumor activity was exhibited by compounds 5, 12 and 14.     

Investigation of the viscoelastic response of high temperature AS4‐12K/RP46 composites using a micromechanical approach

The viscoelastic behavior of a RP46 polyimide resin is characterized at high temperature and the results are used within a micromechanical model to predict the viscoelastic response of a RP46 based carbon fiber composite. The creep master curve of the neat resin is obtained using the time temperature superposition principle (TTSP) from creep tests at three different temperatures, namely 180, 220, and 270°C. The viscoelastic behavior of RP46 is modeled based on Schapery's single integral constitutive equation whose Prony Series coefficients are obtained from the master curve. The acquired properties are then incorporated into a Simplified Unit Cell Micromechanical model to study the creep response of a RP46 resin based composite system. The advantage of this particular micromechanical model lies in its ability to give closed form expressions for the effective viscoelastic response of unidirectional composites as well as each of their constituents. Two types of nonlinearities were observed, one due to stress and the other due to temperature. Both of these nonlinearities can be modeled through the use of proper coefficients in the constitutive equation of the matrix material. The model predictions are found to be in good agreement with experimental results obtained from tests conducted on the RP46 resin based composite system. POLYM. COMPOS., 37:1407–1414, 2016. © 2014 Society of Plastics Engineers     

An investigation of the damage mechanisms and fatigue life diagrams of flax fiber-reinforced polymer laminates

In this paper we investigated the fatigue damage of a unidirectional flax-reinforced epoxy composite using infrared (IR) thermography. Two configurations of flax/epoxy composites layup were studied namely, [0]₁₆ unidirectional ply orientation and [±45]₁₆. The high cycle fatigue strength was determined using a thermographic criterion developed in a previous study. The fatigue limit obtained by the thermographic criterion was confirmed by the results obtained through conventional experimental methods (i.e., Stress level versus Number of cycles to failure). Furthermore, a model for predicting the fatigue life using the IR thermography was evaluated. The model was found to have a good predictive value for the fatigue life. In order to investigate the mechanism of damage initiation in flax/epoxy composites and the damage evolution, during each fatigue test we monitored the crack propagation for a stress level and at different damage stages, a direct correlation between the percentage of cracks and the mean strain was observed.     

A micromechanical approach for the prediction of the time-dependent failure of high temperature polymer matrix composites

In the present study, a novel micromechanical approach is introduced to study the time-dependent failure of unidirectional polymer matrix composites. The main advantage of the present micromechanical model lies in its ability to give closed-form solutions for the effective nonlinear response of unidirectional composites and to predict the material response to any combination of shear and normal loading. The creep failure criterion is expressed in terms of the creep failure functions of the viscoelastic matrix material. The micromechanical model is also used to calculate these creep failure functions from the knowledge of the creep behavior of the composite material in only transverse and shear loadings, thus eliminating the need for any further experimentation. The composite material used in this study is T300/934, which is suitable for service at high temperatures in aerospace applications. The use of micromechanics can give a more accurate insight into the failure mechanisms of the composite materials in particular at high temperatures where the general behavior of the polymer matrix composite is governed by matrix viscoelasticity and the time-dependent failure of the matrix is a localized phenomenon. The obtained creep failure stresses are found to be in reasonable agreement with the experimental data.     

Novel Dipyridinium Lipophile-Based Ionic Liquids Tethering Hydrazone Linkage: Design,Synthesis and Antitumorigenic Study

Novel dicationic pyridinium ionic liquids tethering amphiphilic long alkyl side chains and fluorinated counter anions have been successfully synthesized by means of the quaternization of the dipyridinium hydrazone through its alkylation with different alkyl halides. The resulting halogenated di-ionic liquids underwent a metathesis reaction in order to incorporate some fluorinated counter anions in their structures. The structures of all the resulting di-ionic liquids were characterized by several spectroscopic experiments. The antitumorigenic activities of the investigated compounds were further studied against three different human lung cancer cell lines. Compared to the standard chemotherapeutic agent, cisplatin, the synthesized di-ionic liquids exerted equal, even more active, moderate, or weak anticancer activities against the various lung cancer cell lines under investigation. The observed anticancer activity appears to be enhanced by increasing the length of the aliphatic side chains. Moreover, dicationic pyridinium bearing a nine carbon chain as counter cation and hexafluoro phosphate and/or tetrafluoro bororate as counter anion were selected for further evaluation and demonstrated effective and significant antimetastatic effects and suppressed the colonization ability of the lung cancer cells, suggesting a therapeutic potential for the synthesized compounds in lung cancer treatment.     

Short vs. long column behavior of pultruded glass-fiber reinforced polymer composites

Analytical and experimental studies were conducted for the purpose of establishing a distinguishing criterion between short and long FRP composite column behaviors. The results of investigating 24 full-scale GFRP composite columns are presented. The experimental studies utilized specimens with commonly used ‘Universal’ and ‘Box’ cross-sections which were manufactured by the pultrusion process using E-glass fibers in various forms as reinforcement and polyester and vinylester as binding matrices. The effective slenderness ratios (L/r) of the investigated columns were 3.79, 32.7, 47.9, 63.1 and 75.4 for the ‘Universal’ section and 9.38, 53.9 and 78.9 for the ‘Box’ section. The specimen lengths were 18 inches (0.46 m), 8 foot (2.44 m), 12 foot (3.66 m), 16 foot (4.88 m) and 19.25 foot (5.87 m). All columns were tested in a vertical position and under compressive axial static loading and the fundamental pinned–pinned end-conditions. The columns’ compressive strains, buckling and crippling loads, lateral displacements, initial curvatures, and modes of failure were documented during the course of this investigation. Orthotropic mechanical properties of the composites were experimentally obtained utilizing 44 coupons cut from the column specimens. Analytically, Euler's formula was employed to obtain critical loads for the slender columns. For short columns, the classical plate theory was used to predict columns’ buckling loads. Based on experimental evaluations and analytical results, a slenderness ratio based criterion was established for distinguishing between short and long composite column behaviors. Further conclusions and design recommendations were made.     

Effect of protein hydrolysates from sardinelle (Sardinella aurita) on the oxidative status and blood lipid profile of cholesterol-fed rats

This study was designed to test the hypolipidemic properties and antioxidative activities of sardinelle (Sardinella aurita) protein hydrolysates (SPHs) obtained by treatment with crude enzyme preparations from Bacillus pumilus A1(SPHA1), Bacillus mojavensis A21(SPHA21) and crude enzyme extract from sardinelle viscera (SPHEE).Wistar rats were fed during 7 weeks a standard laboratory diet, a cholesterol-enriched diet (1%) or a cholesterol SPH-enriched diet. The hypercholesterolemic diet induced the elevation of total cholesterol (TC), triglycerides (TG), and low-density lipoprotein cholesterol (LDL-C). Supplementing cholesterol-enriched diet with SPHs or whole sardinelle protein (WSP) at a concentration of 5% (w/w) increased the serum level of high-density lipoprotein cholesterol (HDL-C) and HDL-C/TC ratio and decreased the serum levels of TC, TG, LDL-C and LDL-C/HDL-C ratio significantly.The thiobarbituric acid-reactive substances (TBARS) level, as an indicator of lipid peroxidation, and the activity of superoxide dismutase (SOD), glutathione peroxidase (GPx) and catalase (CAT) were examined. The hepatic antioxidant enzymes activities were significantly decreased and the malondialdehyde (MDA) level was increased in rats fed a cholesterol-enriched diet compared to those fed a standard diet. The treatment of hypercholesterolemic (HCD) diet rats with SPHs reduced the MDA concentration and increased the antioxidant enzyme activities.These results suggested that the hypolipidemic effect of SPHs might be due to their abilities to lower serum TC, TG, and LDL-C levels as well as to their antioxidant activities preventing the lipid peroxidation process.     

A mixed mode crack growth model taking account of fracture surface contact and friction

Fracture surface interactions, of whatever origin, can significantly affect the stress intensity factor, and consequently, can also be relevant to fatigue crack propagation. In the occurrence of interaction between fracture surfaces, the effective loading cycle experienced by material near the crack tip may be very different from that evaluated on the basis of the external loadings only. The purpose of the work described in this paper is to obtain the effective mode II stress intensity factor, k _IIeff, in a surface cracked elasto-plastic plate with a factory roof fracture surface subjected to an in-plane shear (mode II) loading. A new model estimating the magnitude of the frictional mode II stress intensity factor, k _f, arising from the mismatch of the fracture surface roughness during in-plane shear, is developed. Furthermore, the results of this study are employed in modeling the fatigue response of the surface cracked plates subjected to mixed mode loading.