Eastman-kodak Company

Ronald J Maner

Max Allen Weaver

Jean Carroll Fleischer

Gary T Clark

Joseph S Bowers, Jr

Dah-Chieh O Cheng

Disclosed are monoazo dyes derived from diazotized 5-amino-4-halo-3-methylisothiazoles and m-acylaminoaniline couplers. These dyes impart scarlet and red shades on nylon and polyester fibers and exhibit good fastness properties. The dyes are represented by the general formula: ##STR1## wherein R.sub.1 and R.sub.2 are each selected from lower alkyl, cycloalkyl, substituted cycloalkyl, or lower alkyl substituted with phenyl, cyano, sulfonamido, carboxamido, alkoxy, hydroxy, or an imide radical; R.sub.3 is lower alkyl, lower alkyl substituted as above, phenyl, or trifluoromethyl; and X is chlorine or bromine.

Disperse dyes from 5-amino-4-halo-3-methylisothiazoles

Process for the preparation of Compound I by treating Compound II with X.sub.2 or SO.sub.2 X.sub.2 in the presence of a free radical initiator and an anhydride having the formula (RCO).sub.2 O while eliminating the acid halide formed having the formula RCOX from the reaction mixture, wherein Compounds I and II have the formulas ##STR1## and R is C.sub.1 -C.sub.3 alkyl, X is Cl or Br and n is 1, 2 or 3.

Process for the preparation of .alpha.-halogenated cresol esters

Disclosed are novel azo dyes containing an isothiazole diazo moiety which may be substituted, and a tetrahydroquinoline coupler which also may be substituted. The dyes produce red to violet shades on, for example, hydrophobic textile fiber including polyesters, polyamides, and cellulose esters and have excellent properties including lightfastness, washfastness and resistance to sublimation, and dye at unusually low energy levels. The dyes have the general formula ##STR1## wherein the various substituents, R.sup.1 through R.sup.9, are selected from a wide variety of groups such as alkyl, --CN, halogen, alkoxy, and the like.

Disubstituted isothiazole azo dyes containing tetrahydroquinoline type

Azo compounds, having the formula ##STR1## in which R.sup.1 and R.sup.2 are hydrogen, alkyl, alkoxy or halogen and A is a 2-position substituted tetrahydroquinoline type coupler which may be further substituted, or a benzomorpholine type coupler for disperse azo dyes, produce bright, level reddish-blue to blue shades on synthetic polyamide fiber and exhibit good to excellent fastness to light, sublimation, ozone and gas.

Benzoisothiazoleazobenzmorpholine of tetrahydroquinone compounds

Monoazo compounds produce fast blue to green shades on polyester, nylon and cellulose acetate fibers and consist of a 2,1-benzisothiazole-3-yl diazo component and an .alpha.-naphthylamine coupling component, the nitrogen atom of which is monosubstituted with a cycloalkyl, aryl or substituted alkyl group.

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Kingsport, TN, United States of America

Ronald J Maner