m-Substituted Monoazo Dyes: Synthesis, Characterization and Absorption Properties

Abstract

Azo dyes, which are important members of organic compounds; the fact that they have high dyeing power, can be easily synthesized from cheap starting materials, have a very common color scale and have various unique properties makes these materials superior to other organic compounds. Azo dyes synthesized with aromatic amines have strong dyeing strength, have a very bright and more bathochromic effect, show unique properties such as high light and bleaching, especially in the orange-yellow dyeing range. In our study, it was aimed to obtain monoazo dyes with m-substituted carboxylic acid and dioxane core and to synthesize more red shifting dyes. For this purpose, azo coupling reaction of some m-substituted aromatic amines diazotized with 2,4-dihydroxy benzoic acid and 2,2-dimethyl 1,3-dioxane-4,6-dione was performed. The structures of the compounds were characterized by spectrophotometric methods such as FT-IR (Fourier Transform Infrared Spectroscopy), UV-Vis (Ultraviolet Visible Spectroscopy), 1H-NMR (Proton Nuclear Magnetic Resonance). In addition, absorption properties in 5 different solvents were investigated in order to examine the effect of solvent on the absorption spectra of the synthesized compounds. It is thought that these synthesized dyes will contribute to the literature and dyestuff industry.

Keywords

• Azo Dye
• Coupling Reaction
• Azo-Hydrazone Tautomerism

m-Sübstitüeli Monoazo Boyarmaddeler: Sentez, Karakterizasyon ve Absorpsiyon Özellikleri

Abstract

Azo boyarmaddelerin; boyama güçlerinin yüksek, ucuz başlangıç maddelerinden sentezlenebilmeleri, oldukça geniş bir renk skalasına sahip olmaları ve çeşitli özelliklerinin olması, bu maddeleri diğer organik bileşiklerden üstün kılmaktadır. Aromatik aminlerle sentezlenen azo boyarmaddeler, güçlü boyama kuvvetine sahip olmakta, çok parlak ve daha batokromik etkiye sahip, özellikle turuncu-sarı boyama aralığında fazla yüksek ışık ve ağarma gibi kendine has özellikler göstermektedir. Çalışmamızda bu amaçla m-sübstitüeli karboksilik asit ve dioksan iskeletli monoazo boyarmaddelerin elde edilmesi ve daha batokromik renklerin sentezlenmesi hedeflenmiştir. Bunun için diazolanan bazı m-sübstitüeli aromatik aminlerin, 2,4-dihidroksi benzoik asit ve 2,2-dimetil 1,3-dioksan-4,6-dion ile azo kenetlenme reaksiyonu gerçekleştirilmiştir. Bileşiklerin yapıları, FT-IR, UV-Vis ve 1H-NMR gibi spektroskopik metotlar ile karakterize edilmiştir. Ayrıca sentezlenen bileşiklerin absorpsiyon spektrumları üzerinde çözücünün etkisi incelemek amacıyla 5 farklı çözücü içerisinde absorpsiyon özellikleri incelenmiştir. Bu çalışma ile literatüre yeni moleküller kazandırılarak, boyarmadde endüstrisine önemli katkılar sağlayacağı düşünülmektedir.

Keywords

• Azo Boyarmadde
• Kenetlenme Reaksiyonu
• Azo-Hidrazon Tautomerisi

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