Imparting insect repellency to nylon 6 fibers by means of a novel MCT reactive dye

Insect repellency of fiber is a property which makes the fiber to be of interest in the field of military and health. The insect‐repellent substrate could be prepared using either functional finishing or applying an insect‐repellent dye. In this article, insect‐repellent nylon 6 is obtained using a novel insect‐repellent reactive dye containing N,N‐diethyl‐m‐toluamide. To do this, N,N‐diethyl‐m‐toluamide (DEET) was first nitrated at the p‐position relative to amide functionality. The nitrated product was reduced in the presence of C₂H₅OH, SnCl₂, and HCl. The produced amine was then condensed with 2,4,6‐trichloro‐1,3,5‐triazine (cyanuric chloride) as a reactive group in below 5°C. The resultant adduct was finally reacted with an amino group present in 6‐amino‐1‐hydroxy naphthalene‐3‐sulfonic acid (J‐acid) to produce 7‐(4‐chloro‐6‐(4‐(diethylcarbamoyl)‐2‐methylphenylamino)‐1,3,5‐triazin‐2‐ylamino)‐4‐hydroxynaphthalene‐2‐sulfonic acid. To synthesis azo dye, sulfanilic acid was diazotized using HCl and NaNO₂ and then coupled to the above prepared component to produce insect‐repellent reactive dye. An analog dye was prepared via the same route without insect‐repellent group making stage. The chemical structures of the novel dyes were characterized using FTIR and ¹H‐NMR spectroscopy. The spectroscopic properties of the dyes were determined in terms of λ_max and ε_max in aqueous solution. The novel dyes were then reacted with nylon 6 and bonded to it covalently to provide permanent insect‐repellent substrate. The insect‐repellent efficacy of the reacted nylon 6 was studied using standard methods for Anophele mosquito repellent. The insect‐repellent dye reacted nylon 6 showed insect‐repellent activity. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012