Process for preparing azo dyestuffs with ortho-azo cyano groups by cyano exchange of metal cyanides and halo dyestuffs

Claim 2

Process for the production of azo dyestuffs containing at least one cyano group in the diazo component ortho to the azo group, which comprises reacting at a temperature from about room temperature to less than 100°C an azo dyestuff of the formula X--A--N=N--K wherein A stands for an aromatic carbocyclic radical linked to the azo group by a nuclear carbon atom, X stands for Cl or Br linked by a nuclear carbon atom to A in the ortho position to the azo group, and K stands for the radical of a coupling component linked by a nuclear carbon atom to the azo group, with a metal cyanide in a polar aprotic organic solvent with the exchange of the substituent X for cyano wherein the metal cyanide is copper (I) cyanide or copper (I) cyanide formed in situ by the reaction of alkali metal cyanide with a suitable copper (II) salt.

Claim 3

Process of claim 1 wherein A is a radical of the formula ##SPC21## Y is NO 2 , CN, CF 3 , R 1 , OR 1 , SO 2 R 1 , ##EQU13## F, Cl, Br, COR 4 , or ##EQU14## R 1 is CH 3 , C 2 H 5 , or phenyl R 1 is CH 3 , C 2 H 5 , C 2 H 4 OH, C 2 H 4 OCOCH 3 , C 2 H 4 OCH 3 or CH 2 COOCH 3 R 2 and R 3 are H or CH 3 R 4 is H, OH, R 1 , OR 1 , or ##EQU15## R 9 is selected from the group consisting of formyl, substituted or unsubstituted alkyl carbonyl with 1-4 carbons in the alkyl group wherein the substituents are selected from the group consisting of OH, Cl, CN, NH 2 , OCOCH 3 and OCOC 2 H 5 ; phenyl carbonyl, wherein the phenyl radical is unsubstituted or substituted with a member selected from the group consisting of CH 3 , Cl, NO 2 and OCH 3 ; benzyl carbonyl; methyl sulfonyl; phenyl sulfonyl, tolyl sulfonyl, amino carbonyl which is unsubstituted or contains N-substituents selected from the group consisting of CH 3 and C 2 H 5 ; alkoxy carbonyl wherein the alkyl member contains 1 to 2 atoms; benzyloxy carbonyl; phenylsulfonyl; methylsulfonyl and phenyloxycarbonyl; wherein R 10 is selected from the group consisting of alkyl with 1-4 carbon atoms, H, and cyclohexyl; and wherein R 9 and R 10 may together be selected from the group of divalent cyclic radicals consisting of ##SPC22## and wherein Z and Z 1 stands for H or a member of the group CN, NO 2 , CF 3 , OR 1 , SO 2 R 1 , ##EQU16## F, Cl, Br, COR 4 or R 1 .

Claim 4

Process of claim 2 wherein the azo dyestuff reactant has the formula: ##SPC23## wherein Z 1 is H, CN, NO 2 , Cl, Br, SO 2 CH 3 or SO 2 C 2 H 5 ; R 6 is H, OCH 3 or OC 2 H 5 R 7 and R 8 are alkyl or C 1 -4 alkyl with a substituent of the class OH, CN, OCH 3 , Cl, COOCH 3 , COOC 2 H 5 , OCOCH 3 , OCOOCH 3 , and OC 2 H 4 OH; Acyl is CO--R 12 where R 12 is NH 2 , OCH 3 , OC 2 H 5 , CH 3 , C 2 H 5 , CH 2 OH, CH 2 Cl, C 2 H 4 Cl, or CH 2 OCOCH 3

Claim 5

Process of claim 3 wherein Z 1 is CN.

Claim 6

Process of claim 2 wherein the azo dyestuff reactant has the formula ##SPC24## where Z 1 ' is H, CN, NO 2 , Cl, or Br, R 6 is H, OCH 3 or OC 2 H 5 , R 7 and R 8 are C 1-4 alkyl or C 1-4 alkyl with a substituent of the class OH, CN, COOCH 3 , OCOCH 3 , OCOOCH 3 or OC 2 H 4 OH, Acyl is COR 12 where R 12 is CH 3 , CH 2 OH, CH 2 OCOCH 3 , CH 2 --CL, C 2 H 4 Cl or OCH 3 .

Claim 7

The process of claim 1 wherein the reaction occurs at from 25°C to 150°C.

Claim 8

The process of claim 1 wherein the reaction occurs below 100°C.

Claim 9

The process of claim 3 wherein Z' 1 is CN, NO 2 , Cl, Br, SO 2 CH 3 or SO 2 C 2 H 5 .

Claim 10

The process of claim 5 wherein Z' is CN, NO 2 , Cl, or Br.