Triazine Dye Research Articles

Synthesis and Application of New Homobifunctional Reactive Triazine Dyes Containing UV Absorber

Synthesis and Application of New Homobifunctional Reactive Triazine Dyes Containing UV Absorber

Enhancing Visible-Light Photodegradation of TC-HCl by Doping Phosphorus into Self-Sensitized Carbon Nitride Microspheres

SSCN is a new type of self-sensitive photocatalyst. It consists of oxygenated carbon nitride-containing microspheres inside and polymerized triazine dye (TBO) formed on its surface by in situ polymerization. The presence of TBO endows SSCN with a wide range of optical responses. However, the TBO would self-degrade under light, making SSCN extremely unstable in photocatalytic reactions and limiting the practical application of SSCN. The introduction of phosphorus into the structure of SSCN significantly improved the electron–hole separation efficiency and reduced the self-degradation of surface TBO. Phosphorus-doped self-sensitive carbon nitride microspheres (P-SSCN) are easily synthesized by a one-pot solvothermal method—the phosphorus source was added to the precursor solution of SSCN. This resulting material was used for the photodegradation of tetracycline hydrochloride (TC-HCl) for the first time, giving improved visible light sensitivity and high stability in the photocatalytic process. This provides a new method for modifying self-sensitive carbon nitride carbon.

Synthesis, Characterization, and Application of New Reactive Triazine Dye on Cotton and Paper

Synthesis, Characterization, and Application of New Reactive Triazine Dye on Cotton and Paper

Sustainable dyeing of cotton fabric with reactive dye in silicone oil emulsion for improving dye uptake and reducing wastewater

From sustainable chemistry and engineering perspectives, water and energy consumption are arguably the main issues in the textile industry. Thus, a silicone reverse emulsion dyeing system is developed to dye cellulosic textile with reactive dye. When the amount of dye is the same, the color depth of dyed cotton fiber is 13.82 and the fixation of dye is 87.76% in the silicone reverse emulsion dyeing system. In traditional water-based dyeing system, the color depth of dyed cotton fiber and the fixation of dye is only 9.31, 56.63% respectively. The silicone reverse emulsion dyeing technology does not consumes salts, but it can improve the dye fixation by 31.13%, and decreases the dye discharge by 72.41%. For the hydrolysis of bifunctional reactive dye, the main hydrolysis reaction is the individual hydrolysis of monochlorotriazine or vinyl sulfone at the prophase of hydrolysis. After 30 min, the additional β-hydroxyethyl sulfone and hydroxyl triazine dye are hydrolyzed to dihydroxyl dye. To confirm the hydrolytic reaction energy of dye in different dyeing system, the optimization of molecular structure, the hydrolysis reaction gap and the distribution of electron density on the dye were investigated using density functional theory. The hydrolytic reaction energy gap of bifunctional reactive dye is higher in silicone reverse emulsion dyeing system than that in traditional aqueous dyeing system, resulting the hydrolysis of dye is difficult in silicone oil emulsion dyeing system. The electron density is distributed almost entirely on the carbon–carbon double bond and triazine group in the HOMO of the dye, resulting in the LUMO of dyes can attacked by HOMO of hydroxyl anion. These successful investigations of the dyeing performance and the hydrolysis mechanism of dye explain that reactive dye can keep a long reactivity to fiber and effectively reduce the number of washing times, which greatly reduces the discharge of dyeing waste water.

Investigation of sorption capacity of dye-affinity sorbents in the process of purification of factor VIII coagulation

Background. Chromatographic methods, in particular affinity chromatography, are the most effective in obtaining highly purified preparations of plasma proteins. The active triazine and vinyl sulfone dyes are the special group of ligands for affinity chromatograph. We found that the dye-affinity sorbents bind non-target to factor VIII (FVIII) proteins in the previous stages of the study. The sorption capacity of the affinity sorbent is defined as the maximum amount of sample (protein) that can bind to the column under certain conditions. Determining the adsorption limit or limiting capacity of the sorbent makes it possible to identify the feasibility of its use to extract a certain type of protein.
 Objective. To study the sorption capacity of various dye-ligand affinity sorbents in the process of purification of FVIII.
 Materials and methods. We used next sorbents: Diasorb-Procion Blue HB, Diasorb-Procion Gelb M4R and Diasorb-Procion Blue MXR. The cryoprecipitate was initial material. The total protein concentration was determined by the Bradford method, the activity of factors VIII – one-stage clotting method.
 Results and discussion. Sorption of non-target proteins and FVIII activity were investigated after preparation of a number of dilutions of the initial solution of cryoprecipitate. Different concentrations of protein were applied per 1 cm3 of sorbent to select the optimal concentration and do not to oversaturate the column: I – 19.74±0.20 mg of protein/ml; II – 7.94±0.05 mg of protein/ml; III – 3.97±0.05 mg of protein/ml; IV – 1.96±0.04 mg of protein/ml. The maximum sorption capacity among the studied sorbents was 14.62±0.04 mg of protein / 1 cm3 for of sorbent Diasorb-Procion Blue HB. It was found that to achieve maximum purification of FVIII (highest specific activity), the optimal concentration of protein to 1 ml of sorbent should be in the range of 4-8 mg of protein / 1 cm3 of sorbent. The highest degree of purification for these sorbents was 19.65 times at an initial protein concentration of about 4 mg protein/ml (p≤0.01).
 Conclusions. The sorption capacity of sorbents was calculated. It was demonstrated that the maximum sorption capacity is approximately 15 (14.62±0.04) mg of protein / 1 cm3 of sorbent.

Synthesis and characterization of chitosan mini-spheres with immobilized dye as affinity ligand for the purification of lactoperoxidase and lactoferrin from dairy whey

Lactoperoxidase (LP) and lactoferrin (LF) are two interesting proteins present in dairy whey due to their antioxidant, anti-inflammatory, antibacterial, antiviral and antifungal properties. LP and LF are traditionally purified using cation-exchange chromatography, but since the concentration of these proteins in sweet whey are very low (0.03–0.06 g/L for LP and around 0.08–0.20 g/L for LF), clarification, diafiltration, concentration and/or depletion of others whey proteins prior to the ion-exchange chromatography is needed to obtain good adsorption yields. After their elution from the matrix, the overall process results in variable yields. Due to their similar physico-chemical properties, a high cross-contamination is usually present, especially for the LP fraction, where part of the LF is co-eluted.The development of novel supports with immobilized affinity and/or multimodal ligands aims to the direct adsorption of the target proteins even at low concentration and without the need of a pre-treatment of the source. Herein, a new, low-cost support material using chitosan mini-spheres with Orange R-HE triazine dye as immobilized ligand (CMS-Orange R-HE) was synthesized, physico-mechanically characterized and used for the purification of LP and LF by a one-step direct adsorption from dairy whey and a two-step elution process, with minor cross-contamination. CMS-Orange R-HE matrix showed a compression modulus of 47.6 ± 9.8 kPa, predominantly elastic deformation and an open-porous structure with mesopores around 5–20 nm and without ink-bottle pores, ideal for protein purification applications. The affinity between LP and LF for CMS-Orange R-HE matrix was characterized using the Langmuir isotherm model (Kd = 0.48 ± 0.07 mg/mL and 0.31 ± 0.09 mg/mL; qmax = 77.5 ± 4.0 mg/g and 56.0 ± 2.1 mg/g, respectively). Adsorption studies showed that LP interaction with CMS-Orange R-HE was partially influenced by the presence of ionic strength (p < 0.05), whereas LF adsorption was not. These differences of both electrostatic and hydrophobic interactions between LP and LF with the CMS-Orange R-HE matrix were used to develop a differential elution process using Response Surface Methodology (RSM). By one-step direct adsorption from dairy whey and two differential elution steps –by using the CMS-Orange R-HE matrix- LP and LF were obtained with good yields (≈70% for LP and ≈60% for LF), high purity and with minor cross-contamination between them. The strategy presented here, could be applied in other cases of cross-contamination between two proteins, being especially interesting for its application in multimodal chromatography.

Reactive Green 5-Decorated Polyacrylamide/Chitosan Cryogel: An Affinity Matrix for Catalase.

Acrylamide/chitosan-based cryogel was fabricated, and a triazine dye, Reactive Green 5, was attached to the cryogel by nucleophilic substitution to build a dye affinity support for adsorption of catalase enzyme. Characterization of cryogel was performed using FTIR, SEM, EDX, BET, and swelling test. Synthesized cryogel beared pores with ~ 200μm in size and the surface area of 11.8m2/g. Maximum catalase adsorption was (17.6 ± 0.29mg/g) measured at pH4.0 and 25°C. The adsorption sites on the cryogel were saturated at 0.75mg/mL enzyme concentration. Increased ionic strength caused a decrease in adsorption capacity. Desorption of catalase from cryogel was enabled using 0.5M NaSCN solution. Consecutive adsorption experiments were carried out fifteen times to evaluate the reusability of the cryogel. Thermal, storage, and operational stabilities of immobilized catalase were higher than the free one. The data produced implicate that catalase-adsorbed dye-affinity cryogel may be used for H2O2 detection or removal when necessary. Graphical Abstract.

Reduce, Reuse and Recycle in Protein Chromatography: Development of an Affinity Adsorbent from Waste Paper and Its Application for the Purification of Proteases from Fish By-Products.

In the present study, we report the development of a cellulose-based affinity adsorbent and its application for the purification of proteases from fish by-products. The affinity adsorbent was synthesized using cellulose microfibers as the matrix, isolated from recycled newspapers using the acid precipitation method. As an affinity ligand, the triazine dye Cibacron Blue 3GA (CB3GA) was used and immobilized directly onto the cellulose microfibers. Absorption equilibrium studies and frontal affinity chromatography were employed to evaluate the chromatographic performance of the adsorbent using as model proteins bovine serum albumin (BSA) and lysozyme (LYS). Absorption equilibrium studies suggest that the adsorption of both proteins obeys the Langmuir isotherm model. The kinetics of adsorption obey the pseudo-second-order model. The affinity adsorbent was applied for the development of a purification procedure for proteases from Sparus aurata by-products (stomach and pancreas). A single-step purification protocol for trypsin and chymotrypsin was developed and optimized. The protocol afforded enzymes with high yields suitable for technical and industrial purposes.

Application of electrochemical treatment for the removal of triazine dye using aluminium electrodes

AbstractTextile effluents contain triazine-substituted reactive dyes that cause health problems such as cancer, birth defects, and hormone damage. An electrochemical process was employed effectively to degrade azo reactive dye with the aim of reducing the production of carcinogenic chemicals during biodegradation. Textile dye C.I. Reactive Red 2 (RR2), a model pollutant that contains dichloro triazine ring, was subjected to the electrocoagulation process using aluminium (Al) electrodes. A maximum of 97% of colour and 72% of chemical oxygen demand (COD) removal efficiencies were achieved and 9.5 kWh/kg dye electrical energy and 0.8 kg Al/kg dye electrode consumption were observed. The dye removal mechanism was studied by analysing the results of UV-Vis spectra of RR2 and treated samples at various time intervals during electrocoagulation. Fourier transform infrared (FTIR) spectra and energy dispersive X-ray (EDX) spectral studies were used for analysing the electrocoagulated flocs. The results indicate that in this process the dye gets removed by adsorption and there is no significant carcinogenic by-product formation during the degradation of dye.

Community Synergism: Degradation of Triazine Dye Reactive Black 1 by Mixed Bacterial Cultures KND_PR under Microaerophilic and Aerobic Conditions

Mixed bacterial cultures KND_PR comprising five bacterial species, namely Lysinibacillus sp. BAB-4931, Raoultella sp. BAB-4932, Enterococcus sp. BAB-4933, Citrobacter sp. BAB-4934 and Lysinibacillus sp. BAB-4935, were originally developed from contaminated soil near Pirana, Ahmedabad, India. KND_PR have an astonishing ability to degrade Reactive Black 1 (RB1) under both microaerophilic and aerobic conditions within 8 and 12 h, respectively. Mixed bacterial cultures KND_PR showed azoaromatic degradation efficiency up to 1500 mg/L of dye concentration and were able to tolerate salt up to 25 g/L. KND_PR can degrade twenty-five structurally different complex dyes that indicate its catabolic versatility. During azoaromatic degradation, it was observed that under microaerophilic condition KND_PR first followed symmetric cleavage of the azo bond by azoreductase, whereas, under aerobic condition, asymmetric cleavage of RB1 took place via lignin peroxidase. Metabolic pathways for RB1 degradation by KND_PR has been postulated with enzymatic and bioanalytical techniques, which showed the significant conversion of parent dye into low molecular weight aliphatic compound. These results were further confirmed by observing significant results of phytotoxicity experiments with model plants under microaerophilic and aerobic conditions. The foregoing results indicate that the enriched mixed bacterial cultures can efficiently degrade dye under microaerophilic and aerobic conditions within a short time period, which exhibited the usefulness of mixed bacterial cultures KND_PR to tackle the problems associated with dye contaminated wastewater.

Lactoperoxidase purification from whey by using dye affinity chromatography

Bovine lactoperoxidase is a glycoprotein present in milk, whey and colostrum, which might be used in dairy, cosmetic, pharmaceutical, veterinary and agricultural applications due to its broad antimicrobial activity. Here, we describe a novel process for bovine lactoperoxidase purification by using dye affinity chromatography.Eighteen triazine dyes were immobilized on Sepharose 6B and screened for their performance as possible ligands. Five of the dye-Sepharose matrices showed over 90% adsorption of bovine lactoperoxidase directly from whey without any pretreatment using the batch mode, and were thus selected for further adsorption and elution studies. The highest elution degree was obtained using 20mM acetate buffer, pH 5.0, 2M NaCl, as the eluent for all the matrices. Whey processed using the Reactive Red 4-Sepharose matrix in batch mode showed the highest bovine lactoperoxidase purification yield (86.5±3.8%), purification factor (46.1±1.1), and a relative purity higher than 80% according to SDS-PAGE gel densitometry. Whey processed using packed-bed column mode showed lower yields and additional whey pretreatments were needed for dynamic processing.The interaction between bovine lactoperoxidase and Reactive Red 4-Sepharose matrix was characterized using Langmuir isotherm model. The Kd value was 0.21±0.03mg/mL and the Qmax was 32.21±1.24mg/g. The results presented here suggest the potential application of the Reactive Red 4-Sepharose matrix to one-step purification of bovine lactoperoxidase from whey.

Застосування барвник-лігандної хроматографії для очищення фактора VIII зсідання крові

The problem of processing of donor plasma for creating an effective medications is important. Nowadays a big number of methods for fractionation of plasma separation and purification components, especially coagulation factors and fibrinolysis were described. The methods of biospecifical chromatography are especially attractive. The chromatographic purification of factor VIII is a trouble due to potential risks of activation and instability in the presence of plasma proteases. The anion exchange, gel-filtration and affinity chromatography are widely used for purification of coagulation factor VIII. The synthetic active triazine dyes have a number of advantages as ligands. We explored the possibility of using dye-ligand affinity chromatography on silica carriers for the isolation and purification of clotting factor VIII. The results of studies of sorption this factor with different chromatographic sorbents and the method of its purification from cryoprecipitate by binding of additional proteins on Diasorb aminopropyl with immobilized triazine active dyes are described. As a result of this work, we have selected a group of sorbents are the best for purification of factor VIII of blood coagulation: Diasorb-Active scarlet damask 4GT, Diasorb-Procion gelb M4R, Diasorb-Procion blue HB, Diasorb-Procion blue MXR and Diasorb-Active bright blue K. The purification of factor VIII occured due to the phenomenon of negative affinity chromatography. The specific activity of factor increased approximately tenfold.

MoS2-coated microspheres of self-sensitized carbon nitride for efficient photocatalytic hydrogen generation under visible light irradiation

We have successfully coated the self-sensitized carbon nitride (SSCN) microspheres with a layer of MoS2 through a facile one-pot hydrothermal method by using (NH4)2MoS4 as the precursor. The resulted MoS2-coated SSCN photocatalyst appears as a core-shell structure and exhibits enhanced visible-light activities for photocatalytic H2 generation as compared to the un-coated SSCN and the standard g-C3N4 reference with MoS2 coating. The photocatalytic test results suggest that the oligomeric s-triazine dyes on the SSCN surface can provide additional light-harvesting capability and photogenerated charge carriers, and the coated MoS2 layer can serve as active sites for proton reduction towards H2 evolution. This synergistic effect of surface triazine dyes and MoS2 coating greatly promotes the activity of carbon nitride microspheres for vishible-light-driven H2 generation. This work provides a new way of future development of low-cost noble-metal-free photocatalysts for efficient solar-driven hydrogen production.

Self-Sensitized Carbon Nitride Microspheres for Long-Lasting Visible-Light-Driven Hydrogen Generation.

A new type of metal-free photocatalyst is reported having a microsphere core of oxygen-containing carbon nitride and self-sensitized surfaces by covalently linked polymeric triazine dyes. These self-sensitized carbon nitride microspheres exhibit high visible-light activities in photocatalytic H2 generation with excellent stability for more than 100 h reaction. Comparing to the traditional g-C3 N4 with activities terminated at 450 nm, the polymeric triazine dyes on the carbon nitride microsphere surface allow for effective wide-range visible-light harvesting and extend the H2 generation activities up to 600 nm. It is believed that this new type of highly stable self-sensitized metal-free structure opens a new direction of future development of low-cost photocatalysts for efficient and long-term solar fuels production.

Adsorption behavior of Reactive Blue 4, a tri-azine dye on dry cells of Rhizopus oryzae in a batch system

The adsorpion behavior of Reactive Blue 4, a tri-azine dye, on dry Rhizopus oryzae biomass (ROB) has been investigated in aqueous solution with special reference to physicochemical parameters associated with the adsorption process. Adsorption of dye on the biomass is found to be a function of solution pH (optimum 3.0), while temperature has no significant effect. Adsorption rate of biomass is very fast initially and attains equilibrium within 5 h for 50 and 100 mg L−1 and 6 h for 200 mg L−1 initial dye concentrations, respectively, following pseudo-second-order rate model (R2 = 0.99). The equilibrium adsorption isotherm can be best described by Redlich–Peterson model (R2 = 0.95). Scanning electron micrograph demonstrates a conspicuous change in surface morphology of ROB after dye adsorption. Fourier transform infrared spectroscopic data reflect the binding of Reactive Blue 4 on the biomass through complexation reaction involving amino and carboxyl groups. Reactive Blue 4 can be desorbed from the dye loaded biomass using 1(N) NaOH solution. Results establish that ROB has the potential to pollution control management involving Reactive Blue 4.

Antibody mediated rejection of renal transplantation – Clinicopathological correlation

Immobilized metal affinity membranes (IMAMs) were prepared by immobilizing copper ions on microporous regenerated cellulose membranes through different types of chelating agents (dentate and triazine dye). The resulting chelator utilization percentages were 95% for iminodiacetic acid, 56% for N,N,N-tris(carboxymethyl)ethylenediamine, 52% for Cibacron blue 3GA, and 140% for Cibacron red 3BA. On the other hand, triazine dyes were slightly superior to dentate chelators on metal ion utilization for protein adsorption. In batch single-protein adsorptions, the protein adsorption capacity decreased with increasing molecular size and number of accessible surface histidine residues [lysozyme>bovine serum albumin (BSA)>γ-globulin], while the binding strength order was the opposite (γ-globulin>BSA>lysozyme). Moreover, the proportions of specific and nonspecific bindings were evaluated by varying pH and salt concentration conditions. A large fraction of the adsorption capacity was found to come from the nonspecific interactions for the prepared IMAMs. Lastly, batch three-protein adsorptions were performed and weak adsorption competition was observed.

Synthesis, dyeing performance on polyester fiber and antimicrobial studies of some novel pyrazolotriazine and pyrazolyl pyrazolone azo dyes

5-Amino-4-heterylazo-3-phenyl-1H-pyrazoles (2a–d) were diazotized and coupled with malononitrile to give pyrazoloazo malononitrile which by heating in glacial acetic acid gave novel pyrazolo[5,1-c][1,2,4]triazine dyes (3a–d). Also, some diazopyrazolyl pyrazolone dyes (4a–h) were synthesized by diazotization of 2a–d and coupled with some pyrazolone derivatives. The structure of the synthesized dyes was determined by elemental analysis and spectral data. All the synthesized compounds were applied as disperse dyes and their dyeing performance on polyester fabric was studied. The fastness and colorimetric properties were measured. The results revealed that the monoazo dyes have good fastness and good to moderate affinity to polyester fabric than diazo dyes. In addition, the synthesized dyes were screened for their antimicrobial activities against Staphylococcus aureus, Pseudomonas aeruginosa (Gram positive), Bacillus subtitles, Escherichia coli (Gram negative) and Candida albicans, Aspergillus niger (Fungi). The results revealed that most of the prepared dyes have high antibacterial activity.

Acidity Constants Determination of Triazine Dye Derivative in the presence of some Surfactants by Multiwavelength Spectrophotometric and Spectrofluorimetric

Article history: Received March 28, 2013 Received in Revised form August 28, 2013 Accepted 27 November 2013 Available online 28 November 2013 In this work, acidity constants protonated form of 4.4'-bis astilbene-2,2'-disulfonic-disodium salts (TRIAZ) have been determined spectrophotometrically and spectrofluorimetrically at 25C and ionic strength of 0.1M KNO3. A program based on MCR-ALS applied for determination of acidity constants. The results show that the peak values of dye are influenced by the presence of anionic, cationic, and nonionic surfactants. The effects of sodium dodecyl sulfate (SDS), Triton X-100 (TX-100) and cetyl trimethyl ammonium bromide (CTAB) as a surface-active agent on the acidic and basic forms, and the spectral properties of dye were studied. Also, we determined the critical micelle concentration (CMC) for these surfactants by spectrophotometric and spectrofluorimetric triazine dye probes. In addition, by using of evolving factor analysis (EFA) and multivariate curve resolution alternative least squares (MCR-ALS) methods, acidity constants were acquired. © 2014 Growing Science Ltd. All rights reserved.

Design, synthesis and application of benzyl-sulfonate biomimetic affinity adsorbents for monoclonal antibody purification from transgenic corn

The human anti-human immunodeficiency virus (HIV) antibody 2G12 (mAb 2G12) is one of the most broadly neutralizing antibodies against HIV that recognizes a unique epitope on the surface glycoprotein gp120. In the present work, a limited affinity-ligand library was synthesized and evaluated for its ability to bind and purify recombinant mAb 2G12 expressed in transgenic corn. The affinity ligands were structural fragments of polysulfonate triazine dye Cibacron Blue 3GA (CB3GA) and represent novel lead scaffolds for designing synthetic affinity ligands. Solid phase chemistry was used to synthesize variants of CB3GA lead ligand. One immobilized ligand, bearing 4-aminobenzyl sulfonic acid (4ABS) linked on two chlorine atoms of the triazine ring (4ABS-Trz-4ABS), displayed high affinity for mAb 2G12. Absorption equilibrium, 3D molecular modelling and molecular dynamics simulation studies were carried out to provide a detailed picture of the 4ABS-Trz-4ABS interaction with mAb 2G12. This biomimetic affinity ligand was exploited for the development of a facile two-step purification protocol for mAb 2G12. In the first step of the procedure, mAb 2G12 was purified on an S-Sepharose FF cation exchanger, and in the second step, mAb 2G12 was purified using affinity chromatography on 4ABS-Trz-4ABS affinity adsorbent. Analysis of the antibody preparation by sodium dodecyl sulfate-polyacrylamide gel electrophoresis and enzyme-linked immunosorbent assay showed that the mAb 2G12 was fully active and of sufficient purity suitable for analytical applications.

The hidden potential of small synthetic molecules and peptides as affinity ligands for bioseparations

While extensively used as drugs, small synthetic molecules have not yet been widely applied in the industry as affinity ligands for the purification of biopharmaceuticals. Yet, a substantial amount of published research indicates that synthetic ligands, such as triazine scaffolds, amino acids, and peptides show a great deal of promise for becoming the next generation affinity ligands for bioseparations. In this review, we present a comprehensive account on small synthetic ligands, from triazine dyes to the most recent polycyclic peptide ligands, selected for targeting high-value biopharmaceuticals, such as immunoglobulins, blood factors and therapeutic enzymes. These ligands could play a significant role in improving downstream processing and helping the bioprocessing industry overcome the urgent issues of costs and availability posed by growing economies on the global pharmaceutical market.