E.i. Dupont De Nemours and Company

Daniel Shaw James

Vincent G Witterholt

Azo dyes free of water solubilizing groups having the formula ##STR1## WHEREIN R.sub.1 is C.sub.1-4 alkyl, --CH.sub.2 --CH.dbd.CH.sub.2, ##STR2## --(CH.sub.2).sub.n R.sub.8, C.sub.1-4 alkyleneCN, C.sub.2 H.sub.4 OR.sub.7, --CH.sub.2 --CH.dbd.CH--R.sub.8, --C.sub.2 H.sub.4 CONH.sub.2, --C.sub.2 H.sub.4 CONHC.sub.1-4 alkyl, --C.sub.2 H.sub.4 CON(C.sub.1-4 alkyl).sub.2 and --C.sub.2 H.sub.4 CO.sub.2 C.sub.1-4 alkyl; A is a coupling component selected from: a 5- or 6-membered heterocycle consisting of 5-aminopyrazole, 5-pyrazolone, barbituric acid, 6-hydroxypyrid-2-one, 4-hydroxycoumarin and 1,2-dialkylindole; a 1- or 2-naphthol group and an aromatic amine of the formula ##STR3## W is 1,4-naphthylene or ##STR4## R.sub.2 is H, F, Cl, C.sub.1-4 alkyl, OC.sub.1-4 alkyl; R.sub.3 is cyclohexyl or C.sub.1-14 alkylene-R.sub.9 ; R.sub.2 and R.sub.3 together with the nitrogen atom optionally form a 6-membered ring optionally substituted with --OH, OC.sub.2 H.sub.4 CN or OCOC.sub.1-5 alkyl; R.sub.4 is H, ##STR5## R.sub.3 and R.sub.4 together optionally form a 6-membered heterocyclic ring containing the nitrogen atom; R.sub.5 is H; R.sub.6 is H, F, Cl, Br, C.sub.1-4 alkyl, OC.sub.1-4 alkyl, OH, C.sub.1-4 hydroxyalkyl, NHCOCH.dbd.CH.sub.2, NHCOC.sub.1-4 alkyl, NHCOR.sub.8, NHCO.sub.2 C.sub.1-4 alkyl, NHCONHC.sub.1-4 alkyl, NHSO.sub.2 C.sub.1-4 alkyl, NHSO.sub.2 R.sub.8, NHCO.sub.2 R.sub.8, NHCONHR.sub.8, NHCOC.sub.1-4 alkylene-R.sub.10, NHCOC.sub.1-4 alkylene-OC.sub.1-4 alkylene-R.sub.10, NHCO.sub.2 C.sub.11-4 alkyleneOC.sub.1-4 alkyl; R.sub.5 and R.sub.6 together optionally form --CH.dbd.CH--CH.dbd.CH--; R.sub.7 is H or C.sub.1-4 acyl; R.sub.8 is phenyl or phenyl optionally substituted with 1-2 groups selected from Cl, Br, CN, CF.sub.3, NO.sub.2, C.sub.1-4 alkyl, OC.sub.1-4 alkyl, N(C.sub.1-4 alkyl).sub.2 and NHCOC.sub.1-4 alkyl; R.sub.9 is H, OH, CN, COC.sub.1-4 alkyl, OCOCH.dbd.CH.sub.2, OCOC.sub.1-4 alkylene-R.sub.11, OCOR.sub.8, CO.sub.2 R.sub.8, CO.sub.2 C.sub.1-4 alkylene-R.sub.12, ##STR6## OC.sub.1-4 alkylene-R.sub.10, CONHC.sub.1-4 alkylene-R.sub.11, SO.sub.2 R.sub.8, OCONHC.sub.1-4 alkylene-R.sub.10, NHCOC.sub.1-4 alkylene-R.sub.10, NHCONHR.sub.8, NHCOR.sub.8 or R.sub.8 ; R.sub.10 is CN, OH, Cl, Br or R.sub.7 ; R.sub.11 is H, Cl, Br, OC.sub.1-4 alkyl or phenyl; R.sub.12 is H, OH, OC.sub.1-4 alkyl, OCOC.sub.1-4 alkylene-R.sub.11 or OCOR.sub.8 ; R.sub.13 and R.sub.14 are independently H, C.sub.1-4 alkyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or Cl; m is 0 or 1; and n is 1 to 3.

Disperse mono- and bisazo dyes derived from 2-amino-4,5-dicyanoimidazole

The novel copper phthalocyanine-based compound ##STR1## WHERE N IS AN AVERAGE NUMBER OF 3 TO 4, A IS 0 TO 3 BUT LESS THAN N, AND CPC is copper phthalocyanine, and its acid solutions are blue dyes particularly for paper and have excellent bleedfastness. The compound is prepared by reacting copper phthalocyanine sulfonyl chloride with the cyanoamino compounds formed from the reaction between acrylonitrile and ethylenediamine.

Bleedfast phthalocyanine dyes for paper

Biscationic disazo dyes having good exhaust and buildup on acid-modified BCF nylon fibers as well as good lightfastness and wetfastness on such fibers; and a process for dyeing nylon therewith at a pH of about 4 to 7. The dyes have the formula: ##SPC1## Wherein

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Hockessin, DE, United States of America

Daniel Shaw James