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

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

1974-04-03

1978-06-27

Wyman, Daniel E.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260154, 260156, 260160, 260162, 260163, C09B 2936, C09B 2938, C09B 3104

Patent

active

040974758

ABSTRACT:
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.

REFERENCES:
patent: 3133910 (1964-05-01), Baumann et al.
patent: 3213080 (1965-10-01), Bloom et al.
patent: 3336285 (1967-08-01), Towne et al.
patent: 3468871 (1969-09-01), Leverenz et al.
patent: 3515715 (1970-06-01), Straley et al.
patent: 3649162 (1972-03-01), James
patent: 3763140 (1973-10-01), Entschel et al.

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