Novel Disperse Dyes Based on Enaminones: Synthesis, Dyeing Performance on Polyester Fabrics, and Potential Biological Activities.

1-(3-aryl)-3-(dimethylamino)prop-2-en-1-one (enaminones) derivatives and the diazonium salt of para-chloroaniline were used to synthesize several novel disperse azo dyes with high yield and the use of an environmentally friendly approach. At 100 and 130 °C, we dyed polyester fabrics using the new synthesized disperse dyes. At various temperatures, the dyed fabrics' color intensity was assessed. The results we obtained showed that dyeing utilizing a high temperature method at 130 °C was enhanced than dyeing utilizing a low temperature method at 100 °C. Reusing dye baths once or twice was a way to achieve two goals at the same time. The first was obtaining a dyed product at no cost, and the second was a way to treat the wastewater of dyeing bath effluents and reuse it again. Good results were obtained for the fastness characteristics of polyester dyed with disperse dyes. When the disperse dyes were tested against certain types of microbes and cancer cells, they demonstrated good and encouraging findings for the potential to be used as antioxidants and antimicrobial agents.

A Holistic Review of 3-Dimethylamino-1-Arylpropenones Based Disperse Dyes for Dyeing Polyester Fabrics: Synthesis, Characterization, and Antimicrobial Activities.

The enaminone compounds 3-Dimethylamino-1-arylpropenones produced in this review was synthesized by reacting para-methylacetophenone and para-nitroacetophenone with dimethylformamide dimethyl acetal. In this review article, we discuss how to create novel disperse colors by reacting enaminone derivatives 3a and 3b with phenyldiazonium salt. The highly productive procedure of creating new disperse dyes was followed by the process of dyeing polyester fabrics at temperatures between 70 and 130 °C. As a result, the colours' resistance to light, rubbing, perspiration, and washing fastness was assessed. In an effort to show the additional value of these dyes, the expected biological activity of the synthetic dyes against fungus, yeast, and Gram-positive and Gram-negative bacteria was also assessed. We have applied zinc oxide nanoparticles for polyester fabrics treatment to impact them a self-cleaning quality, increase their light fastness, enhance their antibacterial efficacy, and enhance UV protection as part of our ongoing strategy to obtain polyester fabrics with newly acquired specifications.

Can Novel Synthetic Disperse Dyes for Polyester Fabric Dyeing Provide Added Value?

In this review, we present preparation methods for a series of new disperse dyes that we have synthesized over the past thirteen years in an environmentally safe and economical way using innovative methods, conventional methods, or using microwave technology as a safe and uniform method of heating. The results showed that in many of the synthetic reactions we carried out, the use of the microwave strategy provides us with the product in minutes and with higher productivity compared to the conventional methods. This strategy provides or may dispense with the use of harmful organic solvents. As an environmentally friendly approach, we used microwave technology in dyeing polyester fabrics at 130 degrees Celsius, and then, we also introduced ultrasound technology in dyeing polyester fabrics at 80 degrees Celsius as an alternative to dyeing methods at the boiling point of water. Here, the goal was not only to save energy, but also to obtain a color depth higher than the color depth that can be obtained by traditional dyeing methods. It is worth noting that obtaining a higher color depth and using less energy means that the amount of dye remaining in the dyeing bath is less, which facilitates the processing of dyeing baths and therefore does not cause harm to the environment. It is necessary after obtaining dyed polyester fabrics to show their fastness properties, so we explained that these dyes have high fastness properties. The next thought was to use nano-metal oxides to treat polyester fabrics in order to provide these fabrics with important properties. Therefore, we present the strategy for treating polyester fabrics with titanium dioxide nano-particles (TiO2 NPs) or zinc oxide nano-particles (ZnO NPs) in order to enhance their anti-microbial properties, increase their UV protection, increase their light fastness, and enhance their self-cleaning properties. We reviewed the biological activity of all of the newly prepared dyes and showed that most of these dyes possess strong biological activity.

Facile Synthesis of Novel Disperse Dyes for Dyeing Polyester Fabrics: Demonstrating Their Potential Biological Activities.

Original work showed the composition of the dyes and the antimicrobial/UV protective properties of a series of dyes obtained in our laboratories over the past twelve years in an easy way using microwave technology and their comparisons with conventional methods. The results we obtained clearly indicated that by using the microwave strategy, we were able to synthesize the new disperse dyes in minutes and with a much higher productivity when compared to the traditional methods, which took a much longer time, sometimes up to hours. We also introduced ultrasonic technology in dyeing polyester fabrics at 80 °C for an environmentally friendly approach, which was an alternative to traditional dyeing methods at 100 °C; we obtained a much higher color depth than traditional dyeing methods reaching 102.9%. We presented both the biological activity of the prepared new dyes and the fastness properties and clearly indicated that these dyes possess biological activity and high fastness properties.We presented through the results that when dyeing polyester fabrics with some selected disperse dyes, the color strength of polyester fabrics dyed at high temperatures was greater than the color strength of polyester fabrics dyed at low temperatures by 144%, 186%, 265% and 309%. Finally, we presented that a ZnO or TiO2 NPs post-dyeing treatment of polyester fabrics is promising strategy for producing polyester fabrics possess multifunction like self-cleaning property, high light fastness, antimicrobial and anti-ultraviolet properties.

Microwave-Assisted Synthesis of Azo Disperse Dyes for Dyeing Polyester Fabrics: Our Contributions over the Past Decade.

Organic reactions utilizing the microwave strategy have become able to conduct in shorter times, with higher yields, and are compatible with green chemistry protocols. In recent years, microwave technologies as an effective agent in organic synthesis have been successful utilized in textile industries and for the synthesis of dyes, especially disperse dyes. Herein, we present our contributions over the past decade through the use of microwave technology not only in the synthesis of new biologically active organic compounds and disperse dyes, but also the use of this effective, environmentally friendly technology in dyeing polyester fabrics as an alternative to conventional heating methods. We also demonstrate both the fastness properties and biological activities of the newly prepared compounds. In addition, we present the treatment of dyeing baths by reusing them again in the dyeing process, using microwave energy to achieve this goal, and this has environmentally friendly dimensions. Some of the possible utilizations of microwave irradiation have been presented in many different fields of chemistry. We recommend relying on this effective and environmentally safe technology instead of relying on conventional methods that take a lot of time, give low yields, and may have a negative impact on the environment.

A Comprehensive Review on the Synthesis and Versatile Applications of Biologically Active Pyridone-Based Disperse Dyes.

This review summarizes our contributions during last decade on the synthesis of arylazopyridones that may be used as disperse dyes for hydrophobic fabrics utilizing an environmentally benign high temperature dyeing method. The review also discusses the advantages of select disperse dyes based on pyridone moieties as antioxidant, antimicrobial and anticancer agents.

Nano TiO2 Imparting Multifunctional Performance on Dyed Polyester Fabrics with some Disperse Dyes Using High Temperature Dyeing as an Environmentally Benign Method.

Polyester fabrics were dyed with prepared disperse dyes using the high temperature dyeing method. The dye exhaustion of the dye baths were compared to the low-temperature dyeing method in an attempt to study the proportion of the dye effluent solution that affects the environment. The dye uptake of the high temperature dyeing method (HT) of polyester fabric was compared with low temperature dyeing, hence (HT) increased the color strength of the investigated dyes by 309 and 265%. This means that the amount of dye present in the dye effluents by using the high-temperature dyeing method is almost non-existent, and this is reflected positively on the environment as these wastes pollute the environment. Post-treated polyester fabric was prepared through a two-step hot process after being immersed in a solution of Titanium (IV) oxide nanoparticle sizeTiO2 NPs (21 nm primary particle size) at 80 °C followed by curing at 140 °C. The treated fabric realized an optimum UV protection factor of 34.9 and 283.6 degrees. These fabrics also demonstrated a strong ability to improve the light fastness properties. Finally, the potential applications of such value-added fabrics as self-cleaning and antifungal activities were investigated. The results indicated that the treated dyed fabrics with TiO2 NPs endowed fabrics with the excellent self-cleaning of methylene blue dye. From the above, the treated fabrics with nano-titanium dioxide can be used in some promising fields, for example, medical ones.

Dyeing Performance of Disperse Dyes on Polyester Fabrics Using Eco-Friendly Carrier and Their Antioxidant and Anticancer Activities.

Both non eco- and eco-friendly carriers were utilized for accelerating the dyeing rate of polyethylene terephthalate fabrics (PET) dyed with disperse dyes at 100 °C. Fastness properties of the dyed fabrics showed good and excellent results. Finally, the prepared disperse dyes 1 and 2 showed potent anti-tumor cytotoxic activity in vitro using MCF-7 cells (human breast cancer cell line), HepG-2 cells (human Hepatocellular carcinoma), HCT-116 (colon carcinoma), A-549 cells (Lung carcinoma cell line), and anti-oxidant activities.

Dyeing of Polyester with Disperse Dyes: Part 2. Synthesis and Dyeing Characteristics of Some Azo Disperse Dyes for Polyester Fabrics.

The goal of this study was to utilize carrier for accelerating the rate of dyeing not only to enhance dyeing of polyester fabrics dyed with disperse dyes 3a,b, but also to save energy. Both the color strength expressed as dye uptake and the fastness properties of the dyed fabrics were evaluated.

Microwave assisted dyeing of polyester fabrics with disperse dyes.

Dyeing of polyester fabrics with thienobenzochromene disperse dyes under conventional and microwave heating conditions was studied in order to determine whether microwave heating could be used to enhance the dyeability of polyester fabrics. Fastness properties of the dyed samples were measured. All samples dyed with or without microwave heating displayed excellent washing and perspiration fastness. The biological activities of the synthesized dyes against Gram positive bacteria, Gram negative bacteria, yeast and fungus were also evaluated.

Synthesis of some monoazo disperse dyes derived from aminothienochromene.

A series of azo disperse dyes based on aminothienochromene were synthesized. The fastness properties of the dyed samples were measured. Most of the dyed fabrics tested displayed excellent washing and perspiration fastness and moderate light fastness.

Disperse dyes based on aminothiophenes: their dyeing applications on polyester fabrics and their antimicrobial activity.

A series of monoazo disperse dyes derived from arylazothienopyridazines were synthesized. Fastness properties of dyed polyester samples were measured. Most of the dyed fabrics tested displayed excellent washing and perspiration fastness and moderate light fastness. Finally, the biological activity of the synthesized dyes against Gram positive bacteria, Gram negative bacteria and yeast were evaluated.

Azolyacetones as precursors to indoles and naphthofurans facilitated by microwave irradiation with simultaneous cooling.

Phthalimide reacted with phenacyl bromide under microwave irradiation to yield phenacyl isoindolidene-1,3-dione (3b), while 3a reacted with phenylhydrazine to yield the phenylhydrazone 4 that was readily converted into indoylphthalimide 8. Similarly N-benzotriazolylacetone (6a) reacted with phenyl hydrazine to yield the phenylhydrazone 7a that was converted into indoylbenzotriazole 9. Treatment of 8 with hydrazine hydrate afforded a mixture of phthalhydrazide 10 and 3-amino-2-methylindole (11). Reacting enaminone 13 with naphthoquinone (14) afforded the aryl naphthofuran 17. The possibility of the formation of the aldehyde 18 was excluded based on HMQC, which revealed that the carbonyl carbon is not linked to any hydrogen.

Enaminones in heterocyclic synthesis: a novel route to tetrahydropyrimidines, dihydropyridines, triacylbenzenes and naphthofurans under microwave irradiation.

Condensation of phthalimidoacetone (1) with DMFDMA (N,N-Dimethylformamide dimethyl acetal) has afforded enaminone 2. Refluxing 2 with equimolecular amounts of benzaldehyde and urea in acetic acid afforded a mixture of tetrahydropyrimidine 5 and the dihydropyridine 6. Compound 2 undergoes self-condensation on heating in acetic acid or under microwave irradiation in presence of acidic zeolite to give 1,3,5-triacylbenzene 9. Reacting enaminone 11a with naphthoquinone 15 afforded the naphthofuran 18. The possible formation of the aldehyde 19 was excluded based on an HMQC experiment, which revealed that the carbonyl carbon is not linked to any hydrogen.