US 4,374,769 AGranted

Water-soluble tris phenyl bisazo dyes for polyamide fibers

AssigneeEastman Kodak Company

InventorsRalph R. Giles, Max A. Weaver

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Abstract

Disclosed are tris phenyl bisazo dyes bearing one or two sulfated alkoxycarbonyl or sulfated alkylcarbamyl groups. These dyes impart yellow to red shades to fibers, particularly polyamides, and are especially useful for dyeing polyamide (nylon) carpets, generally giving good fastness to light, ozone, oxides of nitrogen, washing, sublimation, crocking, and the like, and having good leveling, exhaustion, build properties, and stability to variations in dyeing condition such as pH and temperature. The present dyes have the general formula: ##STR1## wherein X is --O--, --NH--, --N(alkyl)--, or --N(aryl)--; Z is selected from straight or branched-chain alkylene, and such alkylene containing one or two internal linkages independently selected from ether, amine and amide; M is H, Na, K, or NH.sub.4 ; n is 1 or 2; R.sub.3 is --OH, alkoxy or --NR.sub.8 R.sub.9, wherein R.sub.8 and R.sub.9 are independently selected from H and alkyl and when either R.sub.4 or R.sub.5 is hydroxy or alkoxy ortho to the azo radical, R.sub.3 is further selected from hydrogen, halogen, alkyl, aryl and acylamido; and R, R.sub.1, R.sub.2, R.sub.4, and R.sub.5 are independently selected from hydrogen, halogen, hydroxyl, alkyl, aryl, alkoxy, and acylamido, with the proviso that when R.sub.3 is neither --OH, alkoxy, nor --NR.sub.8 R.sub.9, one of R.sub.4 and R.sub.5 is either hydroxy or alkoxy ortho to the azo radical. These alkyl, alkylene, alkoxy and aryl moieties may be substituted with a wide variety of substituents known to the art.

Claims6

Dependent claims

A dye of the formula:

##STR5## wherein X is --O--, --NH--, --N(alkyl)--, or --N(aryl)--;
Z is selected from straight or branched-chain alkylene, --C.sub.2 H.sub.4 --O--C.sub.2 H.sub.4 --, --C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 --, and --C.sub.2 H.sub.4 NHC.sub.2 H.sub.4 --;
M is H, Na, K or NH.sub.4 ;
n is 1 or 2;
R.sub.3 is --OH, alkoxy or --NR.sub.8 R.sub.9 wherein R.sub.8 and R.sub.9 are independently selected from H and alkyl and when either R.sub.4 or R.sub.5 is hydroxy or alkoxy ortho to the azo radical, R.sub.3 is further selected from hydrogen, halogen, alkyl, and aryl;
R, R.sub.1, R.sub.2, R.sub.4, and R.sub.5 are the same or different groups selected from hydrogen, halogen, hydroxyl, alkyl, aryl, alkoxy and alkanoylamino;
with the proviso that when R.sub.3 is neither --OH, alkoxy, nor --NR.sub.8 R.sub.9, one of R.sub.4 and R.sub.5 is either hydroxy or alkoxy ortho to the azo radical;
and wherein these alkyl, alkylene, alkoxy and aryl moieties are unsubstituted or substituted with one to three substituents selected from hydroxy, halogen, cyano, succinimido, cyclohexyl, alkyl-sulfonyl, alkylthio, alkanoyl, alkanoyloxy, amino, alkylamino, dialkylamino, arylamino, furyl, alkoxy, phenoxy, alkanoylamino, sulfamoyl, alkylsulfamoyl, dialkylsulfamoyl, phenyl and phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl, --COOR.sup.6 wherein R.sup.6 is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy or alkoxy, and OCOR.sup.7 wherein R.sup.7 is alkyl.

5 more elements

Dependencies are inferred from the claim text.