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基于3-氨基-2-硫代-4-噻唑烷酮核的新型酸性染料在羊毛和丝绸织物上的合成、应用及抗菌活性

Synthesis, Application and Antimicrobial Activity of New Acid Dyes Based on 3-Amino-2-thioxo-4-thiazolidinone Nucleus on Wool and Silk Fabrics.

作者信息

Mohamed Fatma A, Elkhabiry Shaban, Ismail Ismail A, Attia Attia O

机构信息

Textile Research Division, National Research Centre, Dokki, Giza 12622.

Textile Research Division, National Research Centre, Dokki, Giza 12622, Egypt.

出版信息

Curr Org Synth. 2022;19(1):166-176. doi: 10.2174/1570179418666210713145959.

DOI:10.2174/1570179418666210713145959
PMID:35139784
Abstract

UNLABELLED

The dyes are synthesized by 3-Amino-2-thioxo-4thiazolidinone (N-Amino rhodanine) with glutaraldehyde or terephthalaldehyde by 2:1 mole to form a and b then coupled with diazonium salts p- Amino benzenesulfonic acid and 4-Amino 3,4-disulfoazobenzeneazobenzene by 2:1 to form new different bis-mono-azo a1 and b1 and diazo a2 and b2 acid dyes. Therefore, the synthesized dyes were applied to both silk and wool fabric materials. We also evaluated the antimicrobial susceptivity of these dyed fabrics to two model gram-negative and gram-positive bacteria. Further, the chemical composition of these dyes is emphasized by an elemental analysis.

AIMS

This paper aims to synthesize and apply dye and antimicrobial to four new acid dyes based on derivatives of N-Amino rhodanine as a chromophoric group. Then, these dyes are used in dyeing silk and wool which have good lightfastness, and are also excellent for washing, rubbing and sweating fastness. Also, we measure antimicrobial susceptivity of silk and wool fabrics to Gram-negative and Gram-positive bacteria.

BACKGROUND

The new synthetic acid dyes, which have antimicrobial susceptivity to gram-negative and gram-positive bacteria, are mostly used on silk and wool fabrics which are excellent for lightfastness, washing, rubbing and sweating fastness.

OBJECTIVES

The present studies aimed at synthesis, characterization and antimicrobial susceptivity to gramnegative and gram-positive bacteria.

METHODS

The infra-red spectrum was recorded using an Infra-red spectrometer, Perkin Elmer/1650 FTIR. The 1H-NMR spectra were recorded using a Varian 400MHz spectrometer. The absorbance of the dyes was measured in the ultraviolet-visible region between 300 and 700 nm by a UNICAM UV spectrophotometer. The dye uptake by wool and silk fabrics was measured using a Shimadzu UV-2401PC (UV/V is spectrophotometer at λmax) before and after dyeing. The produced dyes were found to have a good antimicrobial susceptivity to a variety of bacteria.

RESULTS AND DISCUSSION

The compounds a1, b1, a2 &b2 show good antimicrobial activity toward gramnegative (E. coli), gram-positive (S. aurous) bacteria. The data showed that exhaustion and fastness activities of silk and wool dyed fabrics were both very high.

CONCLUSION

In this work, we prepared newly synthesized acid dyes based on 3-Amino-2-thioxo-4- thiazolidinone derivatives and used them for dyeing wool and silk fabrics. Both synthetic dyes have shown good lightfastness and fastness properties. Also, all dyes have shown a good antimicrobial effect.

摘要

未标记

这些染料由3-氨基-2-硫代-4-噻唑烷酮(N-氨基若丹宁)与戊二醛或对苯二甲醛按2:1摩尔比合成,形成a和b,然后与重氮盐对氨基苯磺酸和4-氨基-3,4-二磺酸偶氮苯按2:1偶联,形成新的不同双单偶氮a1和b1以及双偶氮a2和b2酸性染料。因此,合成的染料被应用于丝绸和羊毛织物材料。我们还评估了这些染色织物对两种革兰氏阴性和革兰氏阳性模型细菌的抗菌敏感性。此外,通过元素分析强调了这些染料的化学成分。

目的

本文旨在合成并应用基于N-氨基若丹宁衍生物作为发色团的四种新型酸性染料及其抗菌剂。然后,将这些染料用于丝绸和羊毛染色,它们具有良好的耐光性,并且在耐洗、耐摩擦和耐汗渍方面也表现出色。此外,我们测量了丝绸和羊毛织物对革兰氏阴性和革兰氏阳性细菌的抗菌敏感性。

背景

对革兰氏阴性和革兰氏阳性细菌具有抗菌敏感性的新型合成酸性染料,大多用于丝绸和羊毛织物,这些织物在耐光性、耐洗、耐摩擦和耐汗渍方面表现出色。

目标

本研究旨在合成、表征以及评估对革兰氏阴性和革兰氏阳性细菌的抗菌敏感性。

方法

使用珀金埃尔默/1650傅里叶变换红外光谱仪记录红外光谱。使用瓦里安400MHz光谱仪记录1H-NMR光谱。用UNICAM紫外可见分光光度计在300至700nm的紫外可见区域测量染料的吸光度。在染色前后,使用岛津UV-2401PC(紫外/可见分光光度计,在λmax处)测量羊毛和丝绸织物对染料的吸收。发现所制备的染料对多种细菌具有良好的抗菌敏感性。

结果与讨论

化合物a1、b1、a2和b2对革兰氏阴性(大肠杆菌)、革兰氏阳性(金黄色葡萄球菌)细菌表现出良好的抗菌活性。数据表明,丝绸和羊毛染色织物的上染率和色牢度都非常高。

结论

在这项工作中,我们制备了基于3-氨基-2-硫代-4-噻唑烷酮衍生物的新合成酸性染料,并将其用于羊毛和丝绸织物的染色。两种合成染料均表现出良好的耐光性和色牢度性能。此外,所有染料均表现出良好的抗菌效果。

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