Tetraacetylethylenediamine Research Articles

Analysis of Residual Tetraacetylethylenediamine Levels according to Rinsing Time of Denture Cleanser

Objective: Tetraacetylethylenediamine (TAED), a denture cleanser was reported to have a risk of acute side effects at high concentrations. This study evaluated residual TAED from denture cleansers after rinsing for different durations. Methods: The rinsing times of denture cleansers were investigated. Specimens made with the denture base-resin were immersed in a denture cleanser and rinsed with running water. The experimental groups were divided based on the rinsing time; G1 was rinsed for 10 s, G2 for 20 s, G3 for 30 s, and G4 for 60 s. No rinsing was performed in the control group. After the elution of TAED from the samples, quantification was performed using high-performance liquid chromatography and mass spectrometry. Results: Seven denture cleansers were investigated; however, the specific rinsing time was not confirmed. Conversely, the control group had a significantly higher amount of TAED (315.4±104.7 ㎍/L), whereas the other groups with > 10 s rinsing time showed significantly decreased residual TAED. Conclusions: To prevent the potential risks of TAED, users should rinse their dentures thoroughly for ≥ 10 s after using a denture cleanser.

Reactive complexes mediated singlet oxygen production by MnO2 catalyzed peracetic acid: Characterization and DFT study

Advanced oxidation technology based on peracetic acid (PAA) has been a hot issue in the remediation of refractory organic pollutants. Here, we investigated manganese dioxide (α-MnO2) effectively activate the in-situ generated PAA by rapid perhydrolysis of sodium percarbonate (SPC) and tetraacetylethylenediamine (TAED) to degrade sulfamethoxazole (SMX). This system followed non-radical pathway only dominated by singlet oxygen (1O2), which can exhibit excellent anti-interference capacity. The generation of metastable manganese intermediates (Mn-PAA*) is a key step in the formation of 1O2. The formation of Mn-PAA* is confirmed by electrochemical and in-situ Raman tests. With the help of density functional theory (DFT), we have probed the behavior of PAA activation on different crystal planes to produce 1O2, with OH cleavage to generate MnIV−O-OOCCH3 being the decisive step for the formation of 1O2. This study is the first to investigate the mechanism of non-radical mediated PAA activation by α-MnO2 and in-depth research the role of Mn-PAA* in the 1O2 generation. The proposed new insights into non-radical process of PAA activation by transition metal will further advance the application of PAA-based AOPs.

Novel bleach activator compounds derived from the reaction of isocyanic acid with selected nucleophiles

AbstractLaundry detergents commonly contain bleach activators that react with the perhydroxy anion produced from perborate or percarbonate anions to form activated peroxy compounds; these enhance bleaching and stain removal capacity especially at lower temperatures, hydrogen peroxide being an inefficient bleach below 60°C. The most commonly used activators are N, N, N′, N′‐tetraacetylethylenediamine (TAED) and sodium nonanoyloxybenzenesulphonate (SNOBS) the former being used across Europe whereas the latter is used widely in the United States and Japan. This research studies the preparation of novel activator compounds which are carbamylated derivatives of selected nucleophiles using either solid or aqueous reactions of nucleophilic carboxylate anions with the highly reactive isocyanic acid entity derived from the acidification of sodium cyanate. The novel activator compounds were then assessed as bleach activators by testing against tea and bilberry‐stained cotton reference fabrics at 40°C in the presence of hydrogen peroxide at pH values ranging from 4 to 10; bleaching efficiency was assessed visually and colorimetrically. Results showed that all of the synthesised compounds were more effective bleach activators across the pH range tested than the standard TAED system.

On Plasma Activated Acetyl Donors: Comparing the Antibacterial Efficacy of Tetraacetylethylenediamine and Pentaacetate Glucose

The study compares how acetyl donor molecules tetraacetylethylenediamine (TAED) and pentaacetate glucose (PAG) improve the antibacterial efficacy of solutions activated with a low-temperature atmospheric-pressure argon plasma jet. Plasma activation of solubilised TAED and PAG produce solutions with different chemical compositions and oxidative potentials. Both acetyl donor molecules enhance the hydrogen peroxide (H2O2) concentration in solution with TAED being more effective compared to PAG. However, PAG is more effective at forming peracetic acid (PAA) from reaction of its acetyl donor groups with plasma generated H2O2. The enhanced oxidative potential of plasma activated TAED and PAG solutions were shown to significantly improve bactericidal activity against common wound pathogens Gram-negative Pseudomonas aeruginosa and Gram-positive Staphylococcus aureus compared to plasma activated water produced without acetyl donors. Furthermore, the oxidative capacity of plasma activated PAG was least affected by the bacterial oxidative defence enzyme catalase, attributed to the high concentration of PAA produced in this formulation. Overall, the above data show that acetyl donors may help improve next generation of antimicrobial formulations produced by plasma, which might help combat increasing problems of antimicrobial resistance.

Energy-Saving One-Step Pre-Treatment Using an Activated Sodium Percarbonate System and Its Bleaching Mechanism for Cotton Fabric.

The traditional pre-treatment of cotton fabric hardly meets the requirement of low carbon emissions due to its large energy consumption and wastewater discharge. In this study, a low-temperature and near-neutral strategy was designed by establishing a tetraacetylethylenediamine (TAED)-activated sodium percarbonate (SPC) system. First, the effects of SPC concentration, temperature and duration on the whiteness index (WI) and capillary effect of cotton fabrics were investigated. Particularly, excess SPC’s ability to create an additional bleaching effect was studied. The optimized activated pre-treatment was compared with the traditional pre-treatment in terms of the bleaching effect and energy consumption. Further, the degradation of morin, which is one of the natural pigments in cotton, was carried out in a homogeneous TAED/SPC system to reveal the bleaching mechanism. Lastly, the application performance of the treated cotton was evaluated by characterizing the dyeability, mechanical properties, morphology, etc. The research results showed that temperature had a significant influence on both the WI and capillary effect, followed by the SPC concentration and duration. The WI was positively correlated with the SPC concentration, but excess SPC could not produce an obvious additional effect. The WI of the fabric increased by 67.6% after the optimized activated bleaching using 10 mmol/L SPC and 15 mmol/L TAED at 70 °C for 30 min. Compared with the traditional process performed at 95 °C for 45 min, the activated process produced approximately 39.3% energy savings. Research on the bleaching mechanism indicated that the reactive species that participated in degrading the morin were the hydroxyl radical and superoxide radical, and the contribution degree of the former was larger than that of the latter. Two degradation components with molecular weights of 180 and 154 were detected using mass spectroscopy. Based on this, the bleaching mechanism of the TAED/SPC system was proposed. Moreover, the fabric after the activated pre-treatment had a suitable dyeability and strength, a lower wax residual and a smoother and cleaner fiber surface. The encouraging results showed that TAED/SPC is a promising bleaching system that is conducive to the sustainable advance of the textile industry.

Acute Toxicity Evaluation of the Disinfectant Containing Percarbonate and Tetraacetylethylenediamine by Measuring Behavioral Responses of Small Fish Using Image Analysis.

Disinfectants containing percarbonate and tetraacetylethylenediamine (TAED) has been developed as an effective and relatively safe disinfectant to destroy viruses and bacteria in animals and humans, however it is known that most disinfectants can cause danger to living organisms including humans. In the current study, acute toxicity of the disinfectant composed of percarbonate and TAED was assessed by measuring behavioral responses as well as lethal concentrations of aquatic organisms such as medaka and zebrafish when they were exposed to it. First, the breeding water properties were determined by measuring dissolved oxygen (DO) and pH changes over time up to 96 h in acute toxicity tests using the medaka, and the lethal concentration 50% (LC50, 88.39 ppm) was calculated using the lethality rate of the fish. This experiment was conducted in compliance with traditional OECD guidelines. Second, the assessment of behavioral responses (locomotive activity and swimming speed) with the zebrafish were assessed by the image analysis to capture the images per second for three hours, and the collected data were processed using image analysis to calculate the locomotive activity and swimming speed. Finally, the LC50 (135.76 ppm) of the disinfectant to the fish was also measured after three hours. Overall, the data revealed that LC50 of the disinfectant may be affected by the pH of the water exposed to the disinfectant, not by the DO in the water. In addition, the results from the image analysis indicated that the behavioral responses of the fish can further assess the acute toxicity of the disinfectant at concentrations below the LC50 and there was a relationship (R2 = 0.85) between the behavioral responses and the survival rate of the fish.Electronic Supplementary Material (ESM)The online version of this article (doi: 10.1007/s12257-021-0419-0) contains supplementary material, which is available to authorized users.

Synthesis of novel of Mn(II), Co(II), and Cu(II) Schiff base complexes and their high catalytic effect on bleaching performance with H2O2

Oxidation catalysts are used in a wide range of industrial processes. For instance, stain bleaching in detergents, bleaching of raw cotton and wood pulp, and drying of alkyd-based paint can be given as examples of oxidation catalysts. In this study, methyl 2-(((3-hydroxynaphthalene -2-yl) methylene) amino) benzoate synthesized as the structure of a new Schiff base ligand by carrying out over 2-hydroxy-1-naphthaldehyde and methyl 2-aminobenzoate. By the reactions of the synthesized Schiff base ligand and Cu(II), Mn(II), and Co(II) acetate salts, their ML2 type complexes were obtained. The structural characterizations of obtained metal ion-Schiff base complexes were performed using FT-IR, 1H-NMR, 13C-NMR, UV-Vis, MALDI-TOF, elemental analysis and melting point methods. The bleaching performances of the prepared Schiff base complexes were examined by the degradation of morin as a hydrophilic dye that characterizes the wine stains. The bleaching processes of Schiff base complexes in the presence of catalyst and H2O2 in an aqueous solution buffered with Na2CO3/ NaHCO3 at pH: 10.5 were investigated using the online spectrophotometric method. It was found that the prepared catalysts exhibited better bleaching performance at 25 °C than that of tetraacetylethylenediamine (TAED) as a bleach activator commercially used in powder detergent formulations.

Oxidation of sulfamethazine by a novel CuS/calcium peroxide/tetraacetylethylenediamine process: High efficiency and contribution of oxygen-centered radicals

Calcium peroxide (CP)-based advanced oxidation processes for water decontamination have stimulated considerable attention due to their inherent merits. Herein, a novel tetraacetylethylenediamine (TAED) coupled CuS/CP (i.e., CuS/TAED/CP) process was tentatively employed for the degradation of sulfamethazine (SMT) in water. Experimental results suggested that peracetic acid (PAA) could be efficiently generated and then activated by CuS in alkaline media, achieving 92.1% removal of SMT in 30 min. Identification of reactive oxygen species (ROS) revealed that the available ROS including hydroxyl radical (•OH), singlet oxygen (1O2), and oxygen-centered radicals (R − O•) together accounted for SMT degradation. Based on quantitative analysis of the relative contribution of involved ROS, R − O• were validated to be the primary reactive species that contributed to 75.2% of SMT removal. Additionally, the role of superoxide radical (O2•−), sulfur species, and calcium hydroxide (Ca(OH)2) were investigated. It was concluded that the O2•− and reductive sulfur species enabled the promoted redox cycle of Cu species, and the Ca(OH)2 generated from CP favored the efficient generation and activation of PAA. Influencing factors like CP dosage, initial pH, and nontarget matrix constituents were also evaluated. Moreover, degradation pathways of SMT were proposed, and the ecotoxicity of these intermediates was predicted. The present work provides a promising and simple approach for the rapid decontamination of antibiotic-polluted water.

Performance Evaluation of the Percarbonate and Perborate Bleach Activators Synthesized by a Low-Cost, Two-Step Method from Phenol

Abstract Bleach activators decrease the energy consumption and fabrics damage in the process of laundry and industrial cotton bleaching. Herein, we demonstrate a low-cost, two-step method for the synthesis of sodium nonanoyloxybenzene sulfonate and sodium lauroyloxybenzene sulfonate from phenol as a simple precursor material for efficient bleach activators. Initially, phenol was sulfonated to sodium p-phenolsulfonate. In the second step, it was acylated with nonanoyl chloride and dodecanoyl chloride to synthesize sodium nonanoyloxybenzene sulfonate and sodium lauroyloxybenzene sulfonate, respectively. Sodium p-phenolsulfonate and the obtained bleach activators were characterized by thermogravimetric analysis, IR-, and 1H NMR spectroscopy. The investigation of their detergency efficiency on different stains and substrates revealed that the as-synthesized bleach activators outperform the commercial tetraacetylethylenediamine (TAED) at room temperature (25°C). The detergency efficiency of sodium lauroyloxybenzene sulfonate for hydrophobic stains at a rather low temperature of 40°C remarkably rises to about 90%.

Combined Scouring and Bleaching of Cotton/Linen Blends by a Near-Neutral Activated Peroxide System

The simultaneous scouring and bleaching of cotton/linen blends was performed in a near-neutral activated peroxide system (pH = 7.2). A response surface quadratic model (RSQM) based on the central composite design (CCD) was established to investigate and optimise the bleaching performance. Research results showed that hydrophobic impurities in the blends had little impact on the bleaching. Temperature was the most significant factor affecting the fabric’s whiteness index (WI), followed by the concentration and duration of the activator tetraacetylethylenediamine (TAED). The optimised process was performed at 70 °C for 40 min, incorporating 20 mmol/l of TAED and 42 mmol/l of H2O2. Compared with the conventional process carried out at 95 °C for 60 min and adding 80 mmol/l H2O2, the activation process provided the fabric with comparable WI and wettability, a smoother and cleaner microcosmic surface, as well as the advantages of saving energy and preserving fabric. This study confirmed the feasibility of an efficient one-step process for neutral scouring and bleaching.

An Overview on Personal Protective Equipment (PPE) Fabricated with Additive Manufacturing Technologies in the Era of COVID-19 Pandemic.

Different additive manufacturing technologies have proven effective and useful in remote medicine and emergency or disaster situations. The coronavirus disease 2019 (COVID-19) disease, caused by the Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2) virus, has had a huge impact on our society, including in relation to the continuous supply of personal protective equipment (PPE). The aim of the study is to give a detailed overview of 3D-printed PPE devices and provide practical information regarding the manufacturing and further design process, as well as describing the potential risks of using them. Open-source models of a half-face mask, safety goggles, and a face-protecting shield are evaluated, considering production time, material usage, and cost. Estimations have been performed with fused filament fabrication (FFF) and selective laser sintering (SLS) technology, highlighting the material characteristics of polylactic acid (PLA), polyamide, and a two-compound silicone. Spectrophotometry measurements of transparent PMMA samples were performed to determine their functionality as goggles or face mask parts. All the tests were carried out before and after the tetra-acetyl-ethylene-diamine (TAED)-based disinfection process. The results show that the disinfection has no significant effect on the mechanical and structural stability of the used polymers; therefore, 3D-printed PPE is reusable. For each device, recommendations and possible means of development are explained. The files of the modified models are provided. SLS and FFF additive manufacturing technology can be useful tools in PPE development and small-series production, but open-source models must be used with special care.

Changes in physicomechanical properties and structures of jute fibers after tetraacetylethylenediamine activated hydrogen peroxide treatment

Tetraacetylethylenediamine (TAED) activated hydrogen peroxide (H2O2) was tentatively used in the bleaching of scoured jute fibers, and the effects of this method on the physicomechanical properties, main chemical compositions, and structures during bleaching were evaluated and compared with conventional H2O2 bleaching. By comparing with H2O2 bleached jute fibers, the TAED-activated H2O2 bleached jute fibers were found to have a better storage stability of whiteness and yellowness, higher breaking tenacity, lower fineness value and breaking extension. The differences in morphological structure and thermogravimetric analysis showed that the TAED-activated H2O2 bleaching system had a stronger ability for the removal of noncellulosic materials than conventional H2O2 bleaching system. The changes in main chemical compositions and Fourier transform infrared spectra further indicated that the removal ability of TAED-activated bleaching for lignin was obviously stronger than that of conventional bleaching, but it had a similar removal ability for hemicellulose. Furthermore, when the whiteness and yellowness values were similar, the amount of H2O2, bleaching temperature, and time of TAED-activated H2O2 bleaching were obviously less than those of H2O2 bleaching.

Potential bleach activators with improved imide hydrolytic stability

The commercially available bleach activator, N,N,N′,N′-tetraacetylethylenediamine (TAED), has been widely used in laundry detergents to enable efficient low-temperature bleaching. However, the competitive hydrolysis of TAED limits its use in liquid detergents. Herein we report the synthesis of two TAED derivatives, N,N,N′,N′-tetracetylpropylene-1,2-diamine (TA(Me)ED) and N,N,N′-triacetylpropylene-1,2-diamine (TriA(Me)ED), through the acetylation of propylene-1,2-diamine. The hydrolytic and perhydrolytic activity of the imide molecules were studied by HPLC to elucidate the structure–function relationship. Due to the increased steric hindrance imparted by the α-methyl group close to the imide, TA(Me)ED and TriA(Me)ED exhibited higher hydrolytic stability than TAED, with the hydrolytic rate constants (kH) at pH 8.0 decreased by 58% and 84% for TA(Me)ED and TriA(Me)ED, respectively. On the other hand, TA(Me)ED and TriA(Me)ED showed comparable perhydrolytic activity with TAED in the presence of peroxide, enabling similar bleaching effect of a model food dye at room temperature. These results suggest these TAED derivatives may have potential being used as improved bleach activators.

Influence of Bleach Activators in Removing Different Soils from Cotton Fabric

The influence of adding Sodium Perborate Tetrahydrate (NaPB) and tetraacetylethylenediamine (TAED) on the efficiency of removing soils from cotton fabric was evaluated in the study. NaPB as inorganic peroxide and TAED as a bleach activator were added to a commercial washing powder agent. Four standard soils applied on cotton fabric (EMPA standard soiled fabrics) were used in the study, i.e. 101 – carbon black/olive oil, 114 – red wine, 116 – blood/ milk/ink and 160 – chocolate. The washing of fabrics was conducted in accordance with the SIST EN ISO 105-C06 standard at 40, 60 and 90 °C in Launder-Ometer apparatus. The washing efficiency was evaluated by determining the CIE L* colour coordinates of the unwashed and washed fabric samples, and the difference in ΔL* colour coordinates among them. The results showed that NaPB and TAED improve the efficiency of washing for two standard soils, have no effect on one, and deteriorate the washing results of one standard soil.

Comparison of four oxidants activated through tetraacetylethylenediamine for developing sustainable and rapid degradation of organic dye

AbstractFour common oxidants, including hydrogen peroxide (H2O2), sodium percarbonate (SPC), sodium perborate (SPB) and sodium persulphate (SPS), were activated with tetraacetylethylenediamine (TAED) to degrade an azo dye, CI Reactive Red 195, in water, for building a novel and rapid oxidative system comprising the merits of cost‐effectiveness and high sustainability. Elevated temperature and high pH level enhanced the activation effect of TAED for accelerating dye degradation. Peracetic acids were confirmed to be the main oxidative species for dye degradation in four TAED/oxidant systems. Hydroxyl radicals and sulphate radicals were also involved in dye degradation in the TAED/SPS system, which showed a stronger oxidative capacity than the other three systems over a wide pH range. More importantly, the addition of inorganic salts or surfactants also favoured the dye degradation in TAED/oxidant systems. Although a slow mineralisation process of the dye was found when the TAED/SPC or SPS system was used, low‐toxic intermediates were detected after the degradation.

Kraft pulp bleaching with a P-stage catalyzed by both bicarbonate and TAED

Peroxide bleaching of softwood and hardwood (eucalypt) kraft pulps was performed in solutions of sodium bicarbonate (NaHCO3), sodium carbonate (Na2CO3), and sodium hydroxide (NaOH). The conventional P stage (hydrogen peroxide + sodium hydroxide; H2O2 + NaOH) was the most effective brightening system without an additional activator. However, peroxide activation by bicarbonate anion (HCO3–) was obvious in all cases where NaHCO3 or Na2CO3 was used. When N,N,N’,N’-tetraacetylethylenediamine (TAED) was added to the bleaching system, Na2CO3 as the alkali source afforded equal or slightly higher bleached brightness compared to NaOH usage for both the softwood and hardwood pulps. This outcome is attributed to simultaneous peroxide activation by HCO3 and TAED. When applied to the eucalypt pulp, the H2O2/Na2CO3/TAED bleaching system also decreased the brightness loss due to thermal reversion.

Improving cellulose nanofibrillation of non-wood fiber using alkaline and bleaching pre-treatments

This study aimed to investigate the effect of alkaline and bleaching pre-treatments on nanofibrillation of jute fibers and on mechanical performance of the ensuing cellulose films. Fibers were submitted to mild or strong alkaline pre-treatments. Then, only after mild alkaline pre-treatment, the fibers were pre-treated with two different bleaching pathways. Succeeding, cellulose nanofibrils were produced by mechanical defibrillation of the pre-treated fibers, while cellulose films were obtained by dewatering (suction) of the cellulose suspensions. Commercial bleached wood (Eucalyptus and Pinus) pulps were used as reference sources of cellulose fibers. Transmission electron microscopy (TEM) was used to investigate the morphology of the obtained cellulose nanofibrils. Cellulose films were compared by their Tensile properties. Defibrillation process was highly influenced by chemical pre-treatments. By the morphological analyses, the most effective nanofibrillation was observed for fibers pre-treated with tetraacetylethylenediamine (TAED), leading to nanofibrils with average diameter of around 20 nm. The crystalline index (CI) was higher for nanofibrils from pre-treated fibers (CI > 80%) when compared to the raw fibers (CI = 61%). Jute fibers pre-treated with TAED bleaching led to higher nanofibrillation, resulting on films with higher Tensile strength and Young's modulus, which were similar to mechanical properties of those from commercial wood pulp.

Enzymatic desizing, bioscouring and enzymatic bleaching of cotton fabric with glucose oxidase

The sized cotton fabric was enzymatically desized, scoured and bleached with an enzyme mixture of starch degrading enzymes, pectinases and glucose oxidases (GOxs) was added to generate hydrogen peroxide (HP). In this study, enzyme selection and process optimisation was made in order to increase the glucose content of the desizing liquor of a starch-sized cotton fabric. The highest glucose concentration of 4175 mg/L was measured in one-bath containing mixture of α-amylase, amyloglucosidase and pectinase and GOx produced 758 mg/L peroxide. This combination was used in further bleaching processes. For bleaching, hydrogen peroxide was converted into peracetic acid (PAA) by incorporating the bleach activator tetraacetylethylenediamine (TAED). Whiteness values, water absorbency, polymerization degree and tenacity at maximum load were measured on pre-treated samples. The total organic carbon (TOC), chemical oxygen demand (COD), biological oxygen demand (BOD5), the biological degradability (BOD5/COD) and the final pH values were measured on residual pre-treatment baths.

Experimental evaluation of the effect of particle properties on the segregation of ternary powder mixtures

Segregation of components, especially the low content level of a highly active substance, has serious deleterious effects on powder formulation. This study investigates the effect of particle properties, particularly size, shape, density and cohesion, on the segregation of laundry detergent powders. Tetraacetylethylenediamine (TAED) particles, spray-dried synthetic detergent powder referred to as Blown Powder (BP) and Enzyme Placebo Granules (EP granules) are used as a model formulation. The segregation of components is evaluated using image processing of the photographic records taken from the front face of a two-dimensional heap of powders. Coefficient of variation concept is considered as segregation index. It is shown that EP granules, the component used as low-level ingredient (< 2 wt%) in the ternary mixture, are prone to extensive segregation due to their higher density as compared to BP and TAED particles. Desired properties for segregation minimisation of EP granules have been further investigated. It is found that the segregation of EP granules can be reduced noticeably by applying a thin layer of a sticky liquid on them before mixing with the rest of powders with full particle size distribution of the components. Polyethylene glycol has been used for this purpose. Addition of 2.5 wt% gives an optimum level to reduce the segregation of EP granules without compromising the flowability of the mixture as well as EP granules themselves.

Application of TAED/H2O2 system for low temperature bleaching of crude cellulose extracted from jute fiber

Tetraacetylethylenediamine (TAED) activated hydrogen peroxide system had been applied for bleaching of crude cellulose extracted from jute fiber. Comparing with conventional hydrogen peroxide bleaching system, those results showed that bleaching temperature and time could be effectively reduced, and a preferable whiteness could be produced under faint alkaline condition. And the optimum conditions for activated bleaching system could be summarized as molar ratio of H2O2/TAED 1:0.7, pH 8, pure hydrogen peroxide 0.09 mol/L, temperature 70 °C and time 60min.