Synthesis, spectral properties, biological activity and application of new 4-(benzyloxy)phenol derived azo dyes for polyester fiber dyeing

Yousefi, Hessamoddin; Yahyazadeh, Asieh; Rufchahi, E.O. Moradi; Rassa, Mehdi

doi:10.1016/j.molliq.2012.12.030

Cited by 37 publications

(23 citation statements)

References 36 publications

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“…The MSDS from the manufacturer informed that the dyes used in this study are a mixture of pigments from the azo/stilbene groups, without specifying the chemical structure of the dye components. However, information about the common chemical properties of azo/stilbene derivatives (Kierman 1990;Yousefi et al 2013), as well as our experimental and computational data, allowed the inference of some probable mechanisms in which these commercial dyes could selectively stain plant tissues. For instance, the best solubility experimentally found for the dyes mixed with 50% hydroalcoholic solution might be attributed to the chemical structural groups usually found in these compounds.…”

Section: Discussionmentioning

confidence: 99%

An inexpensive and environmentally friendly staining method for semi-permanent slides from plant material probed using anatomical and computational chemistry analyses

et al. 2020

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One of the main methods for plant anatomy study is the analysis of thin, transparent, and stained tissue sections. Synthetic dyes traditionally used in anatomical studies might be expensive and produced by specific companies. In contrast, the use of alternative industrial dyes can both represent an inexpensive substitute as well as an environmentally friendly option for conducting plant anatomy studies. In this study, a set of 22 textile dyes was evaluated. Transversal-, longitudinal, and paradermal sections of plant organs obtained using the freehand cutting technique were stained using hydroalcoholic solution (0 to 100%) of textile dyes purchased from a local market. Dyes mixed with 50% hydroalcoholic solution showed higher efficiency in tissue contrast, allowing greater solubility of dye powder and better solution interaction with the plant tissues. Most of the tested dyes showed satisfactory staining results. Cell wall, especially lignified one, showed higher staining efficiency. Computational docking analysis and molecular models of cellulose and lignin showed the probable association mechanisms and dye selectivity to cell wall constituents. Our findings suggest that the developed method can be useful in mixed practical classes of plant anatomy, chemistry, and/or biochemistry, both at high school as well as undergraduate levels.

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Section: Discussionmentioning

confidence: 99%

An inexpensive and environmentally friendly staining method for semi-permanent slides from plant material probed using anatomical and computational chemistry analyses

et al. 2020

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“…Pirazol türevi disazo boyarmaddelerin sentezi ve absorpsiyon spektrumları üzerine çözücü etkisi incelenmiş ve bazik çözücülerde daha canlı renkler elde edildiği gözlenmiştir [14], [15]. Ayrıca son dönem çalışmalarda monoazo ve özellikle disazo boyarmaddelerin antimikrobiyal özellikleri üzerine çalışmalar da oldukça yaygınlaşmış ve büyük değer kazanmıştır [16]- [18].…”

Section: Introductionunclassified

Synthesis of 5-(3'-Amino-4'-Arylazo-1H-Pyrazol-5'-yl Azo) Barbituric Acid Dyes and Investigation of Spectroscopic Properties

Demirçalı¹

2018

Pamukkale J Eng Sci

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Bu çalışmada öncelikle anilin türevleri diazolanmış ve daha sonra diazolanan bu bileşikler, aril-azo-malononitril (1a-1m) bileşiklerini sentezlemek için malononitril ile reaksiyona sokulmuştur. İkinci olarak 4-arilazo-3,5-diamino-1H-pirazol (2a-2m) türevleri, aril-azomalononitril (1a-1m) bileşikleri ile hidrazin monohidrat etkileştirilerek sentezlenmiştir. Son olarak bu bileşiklerin diazonyum tuzları barbitürik asit ile reaksiyona sokulmuş ve hedef bileşikler olan 5-(3'-amino-4'arilazo-1H-pirazol-5'-il-azo) barbitürik asit (3a-3m) bileşikleri elde edilmiştir. 3a-3m bileşiklerinin yapıları AT-IR, 1H-NMR ve Ultraviyolegörünür bölge spektroskopisi gibi spektral yöntemlerle karakterize edilmiştir. Sonuç olarak azo boyarmadde ve tekstil literatürüne 13 adet yeni pirazol türevi dispers disazo boyarmaddeleri kazandırılmıştır. In this study, firstly aniline derivatives were diazotized and then these diazotized compounds were reacted with malononitrile for synthesizing the aril-azo malononitrile compounds (1a-1m). Secondly, 4-arylazo-3,5diamino-1H-pyrazole (2a-2m) derivatives were synthesized by effecting hydrazine monohydrate with aril-azo malononitrile compounds (1a-1m). Finally, the diazonium salts of these compounds were reacted with barbituric acid and 5-(3'-amino-4'-arylazo-1H-pyrazole-5'-yl-azo) barbituric acid compounds (3a-3m) which target compounds were obtained. The structures of (3a-3m) compounds were characterized with AT-IR, 1H-NMR and UV-visible spectroscopy. As a result, it was gained 13 novel disperse disazo dyes to azo dye and textile literature.

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“…9 There have been a few reports about the synthesis of dyes with good dyeing and antimicrobial properties, simultaneously. [10][11][12][13] A series of antimicrobial monoazo disperse dyes have been prepared using 4-amino-N-ethyl glycinate-1,8naphthalimide as the diazo component and salicylic or thiosalicylic acid as coupling agents. 9 The authors claimed that Correspondence concerning this article should be addressed to K. Gharanjig at gharanjig@icrc.ac.ir.…”

Section: Introductionmentioning

confidence: 99%

“…10 A variety of antimicrobial azo dyes has been synthesized by coupling 4-benzyloxyphenol with various heterocyclic amines. 12 The prepared dyes were applied onto polyester fabrics and resulted in orange to red shades with good wash fastness properties. The newly synthesized dyes displayed significant resistance against the tested microorganisms.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and investigation of antimicrobial activity and spectrophotometric and dyeing properties of some novel azo disperse dyes based on naphthalimides

Shaki

Gharanjig

Khosravi

2015

Biotechnology Progress

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A series of novel disperse dyes containing azo group were synthesized through a diazotization and coupling process. The 4-amino-N-2-aminomethylpyridine-1,8-naphthalimide was diazotized by nitrosylsulphuric acid and coupled with various aromatic amines such as N,N-diethylaniline, N,N-dihydroxyethylaniline, 8-hydroxyquinoline, and 2-methylindole. Chemical structures of the synthesized dyes were characterized by Fourier transform infrared (FTIR), differential scanning calorimetry (DSC), proton nuclear magnetic resonance ((1) H NMR), carbon nuclear magnetic resonance ((13) C NMR), elemental analysis, and ultraviolet-visible (UV-visible) spectroscopy. The spectrophotometric data of all dyes were evaluated in various solvents with different polarity. Eventually, the dyes were applied on polyamide fabrics in order to investigate their dyeing properties. The fastness properties of the dyed fabrics such as wash, light, and rubbing fastness degrees were measured by standard methods. Moreover, the color gamut of the synthesized dyes was measured on polyamide fabrics. Results indicated that some of the synthesized dyes were able to dye polyamide fabrics with deep shades. They had very good wash and rubbing fastness degrees and moderate-to-good light fastness on polyamide fabrics. The antibacterial and antifungal activities of the synthesized dyes were evaluated in soluble state and on the dyed fabrics. The results indicated that dye 2 containing N,N-dihydroxyethylaniline as coupler had the highest activity against all the bacteria and fungi used.

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Synthesis, spectral properties, biological activity and application of new 4-(benzyloxy)phenol derived azo dyes for polyester fiber dyeing

Cited by 37 publications

References 36 publications

An inexpensive and environmentally friendly staining method for semi-permanent slides from plant material probed using anatomical and computational chemistry analyses

An inexpensive and environmentally friendly staining method for semi-permanent slides from plant material probed using anatomical and computational chemistry analyses

Synthesis of 5-(3'-Amino-4'-Arylazo-1H-Pyrazol-5'-yl Azo) Barbituric Acid Dyes and Investigation of Spectroscopic Properties

Synthesis and investigation of antimicrobial activity and spectrophotometric and dyeing properties of some novel azo disperse dyes based on naphthalimides

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