One-pot synthesis of 1,3-dimethyl-2-[4-N(N,N-disubstitutedamino)phenylazo]imidazolium cationic dyes

Deligeorgiev, Todor; Zaneva, D.; Simeonova, Nina A.; Simov, D.

doi:10.1016/0143-7208(95)00107-7

Cited by 5 publications

(4 citation statements)

References 4 publications

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“…Azoimidazolium dyes with aminobenzene substituents are of special interest for industrial applications 11. They are typically prepared by reaction of fluoro‐ or chlorobenzene derivatives such as 4 or 5 with amines (through nucleophilic substitution) 13a,b,e. Our direct methodology thus allows to circumvent an additional reaction step.…”

Section: Methodssupporting

confidence: 75%

Synthesis of Azoimidazolium Dyes with Nitrous Oxide

et al. 2014

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A new method for the synthesis of industrially important azoimidazolium dyes is presented. The procedure is based on a reagent which is rarely used in the context of synthetic organic chemistry: nitrous oxide (“laughing gas”). N2O is first coupled to N‐heterocyclic carbenes. Subsequent reaction with aromatic compounds through an AlCl3‐induced CH activation process provides azoimidazolium dyes in good yields.

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Section: Methodssupporting

confidence: 75%

Synthesis of Azoimidazolium Dyes with Nitrous Oxide

et al. 2014

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“… 3 Deligeorgiev et al prepared 2-(4-chlorophenylazo) imidazole-based cationic dyes. 4 Deligeorgiev and Simov prepared a cationic dye from N , N -disubstituted anilines and 2-amino-6-(2-chloroethoxy)benzothiazol. 5 A fluorescent dye having cationic nature was prepared using coumarin as a reactant, and acrylic fibers’ coloration was targeted using this dye.…”

Section: Introductionmentioning

confidence: 99%

“…Alkyl quaternary ammonium salt-based antimicrobial azo dye was prepared by Liu et al A quaternary group-based cationic disperse reactive dye was prepared by Xie and Hou; the dye was applied to wool under acidic conditions to form a covalent linkage with the wool . Deligeorgiev et al prepared 2-(4-chlorophenylazo) imidazole-based cationic dyes . Deligeorgiev and Simov prepared a cationic dye from N , N -disubstituted anilines and 2-amino-6-(2-chloroethoxy)benzothiazol .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Novel Cationic Dye to Impart Mosquito-Repellent and UV Protection to an Acrylic Fabric

Singh

Sheikh

2023

ACS Omega

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The growing demand for innovative routes to develop functional textiles initiated the necessity of new efficient functional molecules. Dyes can provide durable functional protection to textiles due to their ability to generate strong dye–fiber interaction. New dyes to improve a dyed substrate’s quality and aesthetic appearance are in huge demand. This research aims to prepare a mosquito-repellent and UV-protective acrylic fabric using a novel cationic (basic) dye. The cationic dye was synthesized and thoroughly characterized with the help of FTIR, 1H NMR, 13C NMR, and CHN analysis. The dye was further used for the dyeing of the acrylic fabric by using an infrared dyeing machine. To analyze the suitability of dyed fabrics for daily use, washing, rubbing, and light fastness of dyed fabrics were determined. The amount of dye (%) taken up by the acrylic fabric (exhaustion %) was determined, and more than 72% of exhaustion was obtained. The fixation (%) of the dye on acrylic fabrics was also quantified, and more than 80% fixation was obtained. The coloration properties of the dyed fabrics (L*, a*, b*, and K/S) were examined. The dyed fabrics showed a K/S of more than 3. The mosquito-repellent action provided by the dyed fabrics was also analyzed, and 100% repellency was obtained. The dyed fabrics provided an excellent UV-protective property. The multifunctional properties of dyed fabrics were retained significantly even after laundering treatments. The dyed fabrics were characterized using X-ray diffraction and thermogravimetric analysis. A reduction in crystalline peak intensity after dyeing was obtained. The dyed and undyed fabrics were also tested for their tensile strength.

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“…Aryldiazonium salts [ArN 2 ][X] are potent nitrogen‐based Lewis acids that react as electrophiles in a plethora of transformations, of which the formation of azo dyes is one of the key applications . For example, the commercially available Basic Red 51 ( A , Figure ) that is used for the dying of synthetic and natural fibres is produced by the coupling of the corresponding diazonium salt with an imidazole, followed by alkylation . Alternatively, N‐coordination of diazonium salts to Lewis basic N‐heterocyclic carbenes (NHCs) directly affords the strongly coloured azoimidazolium salts [RN 2 (NHC)][X], such as B , …”

Section: Introductionmentioning

confidence: 99%