The Synthesis, Application and Investigation Properties of Two New Acid Dyes Based on Naphthalimide

Hossein Nezhad, M.; Khosravi, A.; Gharanjig, K.; Moradian, S.

The Synthesis, Application and Investigation Properties of Two New Acid Dyes Based on Naphthalimide

Authors

¹ Department of Organic Colorants, Institute for Color Science and Technology

² Department of Polymer Engineering and Color Technology, Amirkabir University of technology

³ Department of Organic Colorants;Center of Excellence for Color science and Technology, Institute for Color Science and Technology

⁴ Center of Excellence for Color Science and Technology, Institute for Color Science and Technology

Abstract

Two novel monoazo acid dyes based on naphthalimide have been synthesized utilizing 4-amino-N-methyl(butyl)-1,8-naphthalimide as the diazo components and J-acid as the coupling component. The 4-amino-N-alkyl(methyl/butyl)-1,8- naphthalimides were diazotized with nitrosylsulphuric acid and afterwards they were coupled with J-acid. All obtained monoazo acid dyes were characterized using DSC, FTIR, 1HNMR and elemental analysis. In order to study and compare their dyeing properties and UV-visible spectroscopy, two monoazo acid dyes based on azobenzene have also been synthesized utilizing aniline and p-nitroaniline as the diazo components and J-acid as the coupling component. Spectrophtometric properties of the synthesized dyes were investigated in different solvents and their halochromic behaviors were considered. Finally, the polyamide and wool fibers were dyed by two monoazo acid dyes and then fastness properties were investigated. The data showed that all monoazo acid dyes have dyed fibers with good dyeing properties and all synthesized acid dyes have excellent wash fastness, good milling and perspiration fastness and poor light fastness.

Keywords