Synthesis of azo pyridone dyes

Abstract

Over 50% of all colorants which are used nowdays are azo dyes and pigments, and among them arylazo pyridone dyes (and pigments) have became of interest in last several decades due to the high molar extinction coefficient, and the medium to high light and wet fastness properties. They find application generally as disperse dyes. The importance of disperse dyes increased in the 1970s and 1980s due to the use of polyester and nylon as the main synthetic fibers. Also, disperse dyes were used rapidly since 1970 in inks for the heat-transfer printing of polyester. The main synthetic route for the preparation of azo dyes is coupling reaction between an aromatic diazo compound and a coupling component. Of all dyes manufactured, about 60% are produced by this reaction. Arylazo pyridone dyes can be prepared from pyridone moiety as a coupling component, where substituent can be on nitrogen, and diazonim salts which can be derived from different substituted anilines or other heterocyclic derivatives. In addition, arylazo dyes containing pyridone ring can be prepared from arylazo diketones or arylazo ketoesters (obtained by coupling 2-diketones or 2-ketoesters with diazonim salts) by condensation with cyanoacetamide. Disazo dyes can be prepared by tetrazotizing a dianiline and coupling it with a pyridone or by diazotizing aniline and coupling it with a dipyridone. Trisazo dyes can be also prepared by diazotizing of aniline and coupling it with a tripyridone or by hexazotizing a trianiline and coupling it with a pyridone. the main goal of this paper is to give a brief review on the synthesis of arylazo pyridone dyes due to the lack of such reviews. In addition, some properties of arylazo pyridone dyes as light fastness and azo-hydrazon tautomerism are disccused.

Preko 50% svih obojenih supstanci koje se danas koriste su azo boje i pigmenti. U ova jedinjenja spadaju i arilazo piridonske boje (i pigmenti), koje se koriste kao disperzne boje, a takođe nalaze primenu i kao komponente u inkdžet grafičkim bojama i LCD ekranima. Kada se koriste kao disperzne boje uglavnom daju žute nijanse i poseduju dobru do odličnu postojanost na mokre obrade i svetlost. U ovom radu je dat kratak prikaz sinteze arilazo piridonskih boja pri čemu je na izabranim primerima ilustrovana sinteza monoazo, disazo i trisazo boja na bazi piridona. Osnovni način dobijanja azo boja pa i arilazo piridonskih boja je reakcija diazokuplovanja, koja se kombinuje sa drugim reakcijama da bi se dobile boje željene strukture. U rada su takođe razmatrana svojstva arilazo pirodonskih boja, kao što su postojanost na svetlost i azo-hidrazon tautomerija.